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\begin{document}

\title{Sorghum Oleoresins: Effect of Extraction on Compositional and Structural
Characteristics}



\author[1]{Eda Kaya}%
\author[1]{Umut Yucel}%
\author[2]{Shanta Peiris}%
\author[2]{Fadi Aramouni}%
\affil[1]{Kansas State University}%
\affil[2]{USDA-ARS}%


\vspace{-1em}



  
  \date{May 25, 2024}


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\selectlanguage{english}
\begin{abstract}
Oleoresins are resin-like viscous materials obtained from plants,
oilseed, or spices with functional properties. The extraction process
determines their stability, composition, and physicochemical properties.
Oleoresins were obtained from ground waxy burgundy whole grain sorghum
with and without ball milling by using the following solvents: two types
of novel ionic liquids (IL1: 1-n-Hexyl-3-methylimidazoliumchloride, IL2:
1-Ethyl-3-methylimidazoliumchloride), ethanol and dichloromethane. The
effects of processing were evaluated for the extraction yield, protein,
fat and total phenolic content, fatty acid composition, particle size
and zeta potential, and FTIR spectra. The use of ILs and ball mill
process significantly (P \textless{} 0.05) affected the extraction yield
and physicochemical properties. The highest extraction yields increased
(31.35\% \selectlanguage{ngerman}± 0.58) when ball milling used with IL2 in comparison to the
lowest (18.37\% ± 0.77) obtained by traditional ethanol extraction. In a
similar way, protein concentration and phenolic content were the highest
(1.37\% ± 0.05 and 0.57\% ± 0.01, respectively) with ball milling
extraction and IL1. The FTIR spectra indicated higher phospholipids (at
1200 cm-1) and protein-phospholipid bonding (at 1700 cm-1) by ILs, and
ball milling as compared to traditional extraction. Overall, wet
milling-assisted extraction by using ball mill and ILs can provide
control for the composition of the oleoresins important for their
functional properties with higher extraction efficiencies as compared to
traditional techniques.%
\end{abstract}\selectlanguage{ngerman}%



\sloppy


\textbf{Introduction}

Oleoresins are phytocomplexes extracted from plant sources, herbs and
oilseeds as oil-rich viscous materials. These resinous extracts include
terpenoids, fatty acids, phospholipids, essential oils, proteins, and
phenolic compounds (Napoli et al., 2019). Oleoresins offer great
potential for value-added food applications (e.g., beverages, sauces and
meat products, baked products, and confectionaries) related to their
chemical stability, uniformity, complex composition of biopolymers,
lipids, polar lipids, and health beneficial phytochemicals. Oleoresins
carry surface active molecules, such as phospholipids and proteins. The
interactions between these proteins, triacylglycerols and phospholipids
are responsible for the integrity and stability of their dispersions and
emulsions.

The extraction method plays an important role in the stability,
composition, yield and structural characteristics of oleoresins.
Conventional solvent extraction involves the use of organic solvents,
such as ethanol, hexane or ethyl acetate, to simultaneously obtain
volatile and non-volatile phytochemicals with functional properties
(Khasanah et al., 2017). Ultrasound- and microwave-assisted extraction
systems were used to increase the extraction yield (Ayub et al., 2023).
Wet milling strategies, such as ball milling, can be used to improve the
extraction efficiency by breaking solid enclosures where the oleoresins
are trapped. For example, ball milling was used to extract sesame paste
from seeds with improved viscosity and reduced particle size (Jin et
al., 2022). A similar strategy was used for the improving the functional
properties of the proteins, such as surface activity, solubility, and
hydrophobicity of proteins extracted from hempseed (Julakanti et al.,
2023).

In addition to the extraction method, the type of solvent determines the
extraction efficiency and physicochemical properties of the oleoresins.
The poly-ionic liquids (ILs) are molten organic salts below
100\textsuperscript{o}C, which combine the characteristics of different
ionic chemicals, received considerable attention as substitutes of
volatile organic solvents due to their versatility, less toxicity,
remarkable solubilization for organic and inorganic compounds (Tolesa et
al., 2017). ILs offer great potential to enhance the extraction
efficiencies for complex material, such as oleoresins containing
biopolymers, surface active molecules and small phytochemicals and to
provide control over their composition. Among the four general groups
(imidazolium, phosphonium, pyridinium, and ammonium), imidazolium based
ILs were widely used for their low viscosity and stability in oxidative
and reductive conditions. In addition, they can also provide high
affinity for lipids and phenolic molecules as compared to conventional
organic solvents, such as ethyl acetate, methanol, and hexane. The
objectives of this study are to investigate the combined effects of wet
milling (i.e., ball milling) and novel ILs
(1-n-Hexyl-3-methylimidazolium chloride, 98\% and
1-Ethyl-3-methylimidazolium chloride, 97\%) on the on the extraction
efficiency of oleoresins from waxy sorghum rich in phenolics and
evaluate their yield, composition (protein, lipid, fatty acid, phenolic
contents) and structural properties of their dispersions (particle size,
zeta potential and FT-IR spectrum) in comparison to conventional solvent
extraction (i.e., ethanol and dichloromethane).

\textbf{2. Experimental Procedures}

\textbf{2.1. Materials}

The extraction solvents ethanol (99.5\%, ACS reagent), dichloromethane
(99.5\%, ACS reagent), and ionic liquids (ILs) (IL\textsubscript{1}:
1-n-Hexyl-3-methylimidazolium chloride, 98\% and IL\textsubscript{2}:
1-Ethyl-3-methylimidazolium chloride, 97\%) were purchased from Fisher
Scientific (Fisher Scientific, Waltham, MA, USA). The selection of ionic
liquids was based on previous literature for higher affinity for polar
lipids and phenolic molecules. The solutions of ILs (40 mL) were
prepared by mixing two ionic liquids with ethanol (99\%) as co-solvent
at 1:2 (w/v) ratio. The waxy burgundy whole grain sorghum was kindly
donated by Nu Life Market LLC (Nu Life Market LLC, Scott City, KS, USA).

\textbf{2.2. Preparation of Oleoresin}

Oleoresin were extracted from ground waxy burgundy whole sorghum grain
with or without wet milling using traditional (ethanol, dichloromethane)
and novel solvents (IL\textsubscript{1} and IL\textsubscript{2}). The
traditional extraction without ball milling was done following the
method of Khasanah et. al (2017) with some modifications. A batch of
whole grain sorghum (50 g) was soaked in NaHCO\textsubscript{3} (0.1 M)
at 1:1 (w/v) ratio 12 h at 21 \selectlanguage{ngerman}± 2 \textsuperscript{o}C. The soaked
sorghum grains were ground using a high-shear blender (Waring
Commercial, Model 7011BU, McConnellsburg, PA, USA) at the highest speed
(22000 rpm) with three-time intervals of 5 minutes. The ground sorghum
(10 g) and the solvent (40 mL) were mixed using a magnetic stirrer for
30 minutes. The slurry was filtered through a cheese cloth to remove the
undissolved solids. The filtrate was centrifuged at 3000 x \emph{g} for
15 min at 20 ± 2 \textsuperscript{o}C to separate oleoresin-rich organic
top layer, which was collected in hermetically sealed glass tubes. The
extraction from the filtrate repeated three times until no sediment was
visible. The weight of sediment and organic phase was recorded in each
dilution step for calculation of the extraction yield. The oleoresins
were concentrated by removing the solvent using a refrigerated vapor
trap (Savant\selectlanguage{english} SpeedVac\selectlanguage{english}, RVT5105, Model SPD300DDA, Thermo Fisher
Scientific, Marietta, OH, USA). The wet milling extraction was done
using the same sorghum and solvent mixture by using a ball mill (Retsch,
PM 100 type, Retsch GmbH, Germany) equipped with a milling bowl (250 mL)
and ceramic balls (diameter:10 mm; quantity: 100 pieces) and operated at
500 rpm with 2 cycles of 15 minutes. The filtrate containing the
oleoresin was separated and concentrated similar to traditional
extraction.

\textbf{2.4. Oleoresin Characterization}

\textbf{2.4.1. Extraction Percentage Yield}

The extraction yield was calculated following the Equation 1:

Extraction yield (\%) =\(\frac{wt[?]\ }{\text{wt}[?]}\ \ x\ 100\) (1)

where wt\textsubscript{e} is the total weight of the extracted oleoresin
and wt\textsubscript{a} is the weight of the whole grain sorghum.

\textbf{2.4.2. Total Protein Content}

The total protein content was analyzed with the Dumas technique at the
Soil Testing Laboratory, Kansas State University. The oleoresins (0.15
+-0.01 g) were combusted, and the nitrogen content was measured on weight
percent basis by using a LECO TruSpec CN Combustion Analyzer (TrueSpec
Micro, LECO, St. Joseph, MI, USA). EDTA was used as the calibration
protein, and the total protein content of samples was calculated by
multiplying the total combustion nitrogen with a factor of 6.25.

\textbf{2.4.3. Total Lipid Analysis}

Total lipid content was determined following a gravimetric method. An
aliquot of oleoresins (1 g) added in a dry glass tube (15 mL) with
chloroform (2 mL) and methanol (4 mL) and sealed with Teflon-lined screw
caps. The tube was shaken well for 10 minutes at 325 rpm. Then,
additional chloroform (2 mL) and water (2 mL) were added, and the tube
was shaken for another 10 minutes. Then, the tube was centrifuged at
2300 rpm for 10 min to separate the organic phase containing the lipid
from the aqueous phase. The organic top layer was collected using a
Fisherbrand\selectlanguage{english} borosilicate glass Pasteur pipet (Fisher Scientific,
Waltham, MA, USA). Additional chloroform (4 mL) was added to the tube,
centrifuged at 2300 rpm, and the top layer with lipid collected. The
solvent was evaporated at 60 degC, and the total lipid in oleoresin sample
was calculated using Equation 2:

Total lipid content (wt\%) =\(\frac{\left(W2-W1\right)x\ V[?]\ x\ 100}{(V[?]\ x\ S[?])}\)(2)

where W\textsubscript{2} is the total weight of the glass tube and the
extract (g), W\textsubscript{1} total weight of empty dried glass tube
(g), V\textsubscript{l} is the total volume of chloroform layer (mL),
V\textsubscript{a} is the volume of the extract (mL) and
S\textsubscript{x} is the weight of the oleoresin (g).

\textbf{2.4.4. Fatty Acid Composition}

The fatty acid composition was measured using the fatty acid methyl
esters (FAME) method described by Taghvaei et al. (2021). In brief, an
aliquot of oleoresin (1 mL) was transferred into glass test tube (15 mL)
with boron trifluoride (14\%) in methanol (3 mL) and heated at
100\textsuperscript{o}C for 40 minutes. Saturated NaCl solution (15 mL)
and hexane (3 mL) was added, and the tube was inverted 3 times. The
mixture was allowed to settle for a few minutes for the separation of
organic and aqueous phases. The organic top layer was collected using a
Pasteur pipette into a clean test tube, where a small amount (1 g) of
anhydrous sodium sulfate was added to remove any residual moisture. The
methylated organic layer (1 \selectlanguage{greek}µ\selectlanguage{english}L) was injected into a GC-MS system (HP
5890--5973 MS, Agilent) equipped with an HP-23 FAME capillary column (30
m length x 0.25 mm i.d. x 0.25 \selectlanguage{greek}μ\selectlanguage{english}m film thickness) (Agilent Technologies,
Santa Clara, CA, USA). Helium (1 mL/min) was used as the carrier gas.
The initial oven temperature was 60 \textsuperscript{o}C ld for 0.5
min), then brought to 150 \textsuperscript{o}C at a rate of
5\textsuperscript{o}C / min, followed by an increase of
15\textsuperscript{o}C / min to a final temperature of
230\textsuperscript{o}C. The program was finalized with a hold at
230\textsuperscript{o}C for 4 min. In addition to the National Institute
of Standards and Technology (NIST) 2014 database, a FAME standard
(\textgreater{} 95 \%, FAME Standard Mixture, St, Louis, MO, USA) over a
concentration range of 1.25 -10 mg/mL was used for identification and
quantification. The quantification was performed by using the peak
areas.

\textbf{2.4.5. Phenolic Content and Composition}

The total phenolic content was determined using Folin Ciocalteu method
(Lamuela-Ravent\selectlanguage{ngerman}ós, 2017). The calibration curve was plotted by mixing
aliquots (1 mL) of Gallic acid solutions over a range of concentrations
(800, 400, 200, 100, 50, 25, 12.5 and 6.25 \selectlanguage{greek}μ\selectlanguage{english}g/mL) with Folin Ciocalteu
reagent (5 mL) and anhydrous sodium carbonate solution (4 mL). The
phenolic content of the oleoresin was measured by mixing the sample (2.5
mL) and Folin Ciocalteu- anhydrous sodium carbonate reagents at the 1:1
(v/v) ratio. The solution was kept for 1 h at 25\textsuperscript{o}C.
The absorbance was measured at 725 nm using a spectrophotometer. Total
phenolic content was expressed as mg of gallic acid equivalents (GAE)
per gram of oleoresin (mg GAE/g oleoresin) using Equation 3:

C = C\textsubscript{1} x \(\frac{V}{m}\) (3)

where C is the total phenolic content (mg/g) in GAE,
C\textsubscript{1}is the concentration of gallic acid established from
the calibration curve in mg/mL, V and m are the volume and weight of
oleoresin, respectively.

The phenolic compounds were determined using the protocol described by
(Tohma et al., 2017). The samples were prepared by mixing oleoresin (20
mg) with a mixture (2mL) of methanol:ethanol (90:10 v/v) in a glass tube
with screw top (15 mL) and shaken in a wrist shaker for 1 h. Then, the
solution was filtered with a PTFE filter (0.45 \selectlanguage{greek}μ\selectlanguage{english}m) and transferred to a
1 mL polypropylene vial (12 mm x 32 mm). The analysis was conducted
using an HPLC system (Agilent Technologies, 1100 series, Santa Clara,
CA, USA) equipped with a C18 column (TOSOH Bioscience LC, TSKgel ods-80,
4.6 mm ID\selectlanguage{ngerman}×25 cm, 5\selectlanguage{greek}μ\selectlanguage{english}m Millipore Sigma, MA, USA) and a diode-array
detector (DAD) (Hewlett-Packard, Palo Alto, CA, USA) operated at 260-430
nm. The mobile phase (elution rate of 1.0 ml/min) was composed of
acetonitrile (solvent A), methanol (solvent B) and water with acetic
acid (solvent C) with a gradient system as follows: 0-5 min 5-8\% A,
5-8\% B and 90-84\% C; 5-15 min 8-10\% A, 8-10\% B and 84-80\% C; 15-25
min 10-25\% A, 10-0\% B and 80-75\% C; 25-35 min 25-30\% A, 75-70\% C;
35-45 min 30-60\% A and 70-40\% C. The injection volume was 20 \selectlanguage{greek}μ\selectlanguage{english}L and
the column temperature was 30\textsuperscript{o}C. Each phenolic
compound was identified by their retention time in comparison with
standard compounds. The peak areas were quantified using Chem Station
software as areas under the curve and calibration curve prepared by
their analytical standards. The concentration of each phenolic compound
in oleoresin samples was determined using Equation 4:

Concentration of compound =\(\frac{\text{Area\ of\ sample}}{\text{Area\ of\ standard}}\) x Concentration of
standard (4)

\textbf{2.4.6. Fourier Transform Infrared (FTIR) Analysis}

The FTIR analysis was conducted at the Center for Grain and Animal
Health Research (USDA-ARS, Manhattan, KS, USA). Attenuated total
reflectance (ATR)-FTIR spectra collected at 400--4000
cm\textsuperscript{-1} range with a resolution of 4
cm\textsuperscript{-1}, data spacing of 0.482 cm\textsuperscript{-1},
and 32 scans using a Thermo Nicolet iS50 FTIR (Thermo Fisher Scientific
Co., Waltham, MA) spectrometer equipped with a single-bounce diamond
crystal and a deuterated triglycine sulfate detector. Measurements were
repeated twice for each sample at ambient temperature. The quantitative
analysis was done by ``peak fitting'' procedure and individual component
bands according to a Gaussian curve fit (GRAMS/AI Spectroscopy Software
Suite, Thermo Scientific, Waltham, MA, USA).

\textbf{2.4.7. Particle Size and Zeta Potential of Oleoresin}

Particle size and zeta potential were analyzed using a dynamic light
scattering (DLS) particle size analyzer (Delsa Max Pro, Beckman Coulter,
Kraemer Blvd. Brea, CA, USA) at 25 \selectlanguage{ngerman}°C. Prior to analysis, oleoresins
were diluted in ultra-pure water at the 1:100 (w/v) ratio and dispersed
using an ultrasound bath for 10 minutes and high-shear homogenizer (Omni
THModel TH-115, Omni International, Kennesaw GA, USA) for 10 min with
inner and outer probe diameters of 7 mm x 125 mm (de Aguiar et al.,
2021; Nikiforidis \& Kiosseoglou, 2009). The measurements were repeated
twice for each replication and their average was used.

\textbf{2.5. Statistical Analysis}

All samples were prepared in triplicate. The experimental data were
analyzed using Minitab (version 17.1, LLC, State College, PA, USA) and
the values were expressed as mean ± standard deviation. A one-way
analysis of variance (ANOVA) and Tukey's multiple comparison test were
used to analyze significant differences among samples at \selectlanguage{greek}α \selectlanguage{english}= 0.05.

\textbf{3. Results and Discussion}

\textbf{3.1. Effect of extraction conditions on yield}

The solvent type had a significant (\emph{P} \textless{} 0.05) effect on
the extraction yield of oleoresins (Fig. 1). Overall, ILs increased
(\emph{P \textless{} 0.05} ) the extraction yield (25.11 \selectlanguage{ngerman}± 0.84 wt\% for
IL\textsubscript{1} as compared to 18.37 ± 1.34 wt\% for ethanol) via
traditional extraction (i.e., without ball milling) (Fig.1). The higher
extraction efficiencies with the imidazolium based ILs were as expected
due to the combined extractive power of the composite systems. In a
similar way, other researchers showed that imidazolium based ILs can
increase the extraction yield of bioactive phytochemicals, such as
flavonoids, alkaloids, caffein, etc., from plant tissue (Bogdanov \&
Svinyarov, 2013; Claudio et. al, 2013). The increase in the extraction
efficiencies can be explained by the combination of dipole, ionic, and
hydrophobic interactions of the IL components. In parallel to the
extraction efficiency, lipid, protein, and phenolic compositions were
also significantly (P \textless{} 0.05) affected by the extraction
conditions as discussed in the following sections (Table 1). The
efficiency of traditional solvent extraction with ethanol and
dichloromethane was the same (P \textgreater{} 0.05); however, the
compositions of their oleoresin extracts were different. There was no
significant difference (\emph{P \textgreater{} 0.05} ) in the extraction
yield of two ILs as well (Fig. 1). Thus, the difference between the type
of charged groups in ILs was not responsible for breaking the solid
enclosure required for extraction. In a recent study, Cheng et. al
(2020) used different ILs with 11 anions and 8 imidazolium-based cations
including the ILs in our study for extraction of isoflavone compounds
from \emph{Puerariae lobatae.} They showed that the extraction
efficiencies of the ethyl and hexyl substituted imidazolium ILs were the
same, yet changed with ion concentration in their solution. Therefore,
we can conclude that imidazolium ILs regardless of the cation and anion
composition were more effective than traditional solvents due to their
ability to disrupt cellular structure that determine extraction
capacity. On the other hand, the chemical difference between the two ILs
affected the oleoresin composition (Table 1) as discussed later.

The wet milling process with a ball mill significantly (\emph{P}
\textless{} 0.05) increased the extraction yield as compared to
traditional solvent extraction. For example, the extraction yield
increased more than 50\% when IL\textsubscript{2} was used with ball
mill (31.36 ± 1.01 wt\%) as compared to traditional batch extraction
(18.92 ± 0.68 wt\%) (Fig. 1). This can be explained by the ability of
ball mill to break down the integrity of the hard enclosure trapping the
oleoresins via omnidirectional impact of the beads and associated high
shear.

\textbf{3.2. Oleoresin Composition}

In parallel with the extraction efficiency results, it was not
surprising to observe that the solvent type had significant
(\emph{P}\textless{} 0.05) effect on the total lipid, protein and
phenolic content of oleoresins. Following the traditional solvent
extraction approach, the highest protein (0.67 ± 0.03 wt\%), lipid
(69.22 ± 0.04 wt\%) and phenolic contents (48 ± 0.01 mg GAE/g) were
obtained with IL\textsubscript{1} (Table 1). The lowest extraction for
protein (0.36 ± 0.02 wt\%) was obtained using dichloromethane, while the
lowest lipid (53.12 ± 0.08 wt\%) and phenolic contents (21 ± 0.02 mg
GAE/g) were observed using ethanol. Wet milling extraction with a ball
mill increased (\emph{P} \textless{} 0.05) the total lipid (82.19±0.07
wt\%), protein (1.37 ± 0.05 wt\%), and phenolic content (57 ± 0.01 mg
GAE/g) of oleoresin when IL\textsubscript{1} used as compared to total
lipid ( 69.22 ±0.04 wt\%), protein 0.67 ± 0.03 wt\%), and phenolic
content (48 ± 0.01 mg GAE/g) with traditional extraction (Table 1). In a
similar way to traditional extraction, IL\textsubscript{1} and
IL\textsubscript{2} were same (\emph{P}\textgreater{} 0.05) for lipid,
protein, phenolic content. Jin et. al (2022) also found that using ball
mill increased the overall content of protein, fat, and volatile
compounds in the sesame seed extracts as compared to colloid and stone
mills. The increase was higher for protein (51.1\%) than lipid (15.8 \%)
at the conditions for the highest extraction yield when IL is used
(Table 1).

The fatty acid composition of the oleoresins was analyzed by using gas
chromatography and shown in Table 2. Oleic acid, palmitic acid,
palmitoleic acid and myristic acid were the most abundant fatty acids in
all the oleoresins. Octadecanoic acid was present only in trace amounts
for all extracts with a concentration range between 0.292 to 1.792\%.
This aligned with the fatty acid content of raw sorghum varieties of
reported in previous studies (Espitia-Hernández et al., 2022). The
solvent type had a significant (\emph{P} \textless{} 0.05) effect on the
fatty acid composition. The unsaturated fatty acids (oleic and
palmitoleic acids) increased more than saturated ones (myristic and
palmitic acids) when ILs were used instead of dichloromethane and
ethanol. This was probably related to the double bonds of unsaturated
fatty acids that provided lower free energy for temporal ionization and
to interact with cations and anions of ionic liquids. In another study,
Li et al. (2009) showed that higher polyunsaturated fatty acid extracts
from cod liver oil were obtained with ILs in comparison to organic
solvents, such as acetone, methanol, acetonitrile, and chloroform. The
percentages of oleic, palmitic and myristic acids were not significantly
(\emph{P \textgreater{} 0.05} ) different when IL\textsubscript{1} and
IL\textsubscript{2} were used with traditional extraction process while
it was significantly (\emph{P \textless{} 0.05} ) different for
palmitoleic acid. In contrast, the percentage of these fatty acids were
significantly (\emph{P \textless{} 0.05} ) different when
dichloromethane or ethanol was used. The concentrations of both oleic
and palmitic acids were significantly (\emph{P \textless{} 0.05} ) lower
with both traditional solvents than ILs when traditional extraction was
conducted.

The extraction method also had a significant (\emph{P \textless{} 0.05}
) effect on the fatty acid composition (Table 2). The percentage of
oleic and palmitoleic acids significantly (\emph{P \textless{} 0.05} )
increased while myristic and palmitic acids significantly (\emph{P
\textgreater{} 0.05} ) decreased when ball milling process was conducted
instead of traditional process. The highest concentration of oleic acid,
the most abundant unsaturated fatty acid in the oleoresins was 23.663\%
± 0.003 with the combined action of ball milling and
IL\textsubscript{1}. In addition to this, the increase in oleic acid was
45.89\% and 29.15\% when ball milling was used with
IL\textsubscript{2}and ethanol respectively, as compared to traditional
solvent extraction with the same solvents. On the other hand, the
decrease in myristic acid was 24.57\% and 34.44\% when ball milling was
used with IL\textsubscript{2} and ethanol respectively, as compared to
traditional extraction using IL\textsubscript{2} and ethanol. Similar
changes in unsaturated (palmitoleic and oleic acids) and saturated
(myristic and palmitic acids) fatty acid concentrations were observed by
Korber et. al (2022) where ball mill extraction was applied for lettuce
plants (\emph{Lactuca sativa L.)} to extract galactolipids and
sulfolipids. Furthermore, the percentages of oleic, palmitoleic,
myristic and palmitic acids were not significantly (\emph{P
\textgreater{} 0.05} ) different when IL\textsubscript{1} and
IL\textsubscript{2} were used with ball milling extraction. Similar to
the traditional extraction, the percentage of these fatty acids changed
when dichloromethane and ethanol were selected. The use of ILs increased
(\emph{P \textless{} 0.05} ) the total phenolic content of the
oleoresins. Oleoresins were rich in eight phenolic compounds: caffeic
acids, coumaric acid, ferulic acids, apigenidin, luteolidin, 7-methoxy
apigeninidin, eriodictyol and narencenin (Table 3). The HPLC
chromatogram was given in Supplementary Materials (Fig. S1). Caffeic
acid, coumaric acid and luteolidin were the major phenolic compounds
present in all oleosome samples. Among these, caffeic acid followed by
coumaric acid were the most abundant and they remained so with all types
of solvents. The solvent type significantly (\emph{P} \textless{} 0.05)
affected the total phenolic content and composition (Table 3). The
percent increase in caffeic acid was 74.84\% when IL\textsubscript{1}
was used instead of dichloromethane with the traditional extraction
process. In addition to this, there was no significant (\emph{P}
\textgreater{} 0.05) difference between IL\textsubscript{1} and
IL\textsubscript{2} while ethanol and dichloromethane showed significant
(\emph{P} \textless{} 0.05) difference using the same extraction method.

The extraction method also had a significant (\emph{P \textless{} 0.05}
) effect on the phenolic composition (Table 3). The increase in caffeic
acid was 28.93\% and 50.16\% when ball milling was combined with
IL\textsubscript{1} and dichloromethane respectively, as compared with
the traditional extraction process using the same solvents. Similar
effects were observed in luteolinidin when ball milling and traditional
extraction processes were compared: the increase in luteolinidin was
21.78\% and 57.68\% when ball milling extraction was performed with
IL\textsubscript{2} and ethanol respectively, as compared with
traditional extraction. Furthermore, the percentages of caffeic acid
were not significantly (\emph{P \textgreater{} 0.05} ) different when
IL\textsubscript{1} and IL\textsubscript{2} with the combined action of
ball milling process, but there was a slight significant difference when
ethanol and dichloromethane were used. Similarly, in another study,
Talekar et al. (2019) showed that total phenolics and antioxidant
``punicalagin'' increased when ball-mill pre-treatment was used for
pomegranate peel waste, and it was more efficient than
ultrasound-assisted and Soxhlet extraction.

\textbf{3.3. Oleosome Structure}

The organic moieties containing O-H and bonds, such as phospholipid
bilayer, glycosidic bond and protein-phospholipid complexes, were
analyzed by FTIR spectroscopy (Fig. 3). The stretching band of C=O at
1100 cm\textsuperscript{-1} and 1600 cm\textsuperscript{-1} was assigned
to the polysaccharides and phospholipid bilayers, respectively (Li et
al., 2022). The H-OH stretching around 2800-2900 cm\textsuperscript{-1}
was assigned to glycosidic bond between glycoprotein units, and the O-H
stretching between 3000-3500 cm\textsuperscript{-1} to the presence of
protein-phospholipid complexes (Qi et al., 2017). The FTIR spectra was
not affected (\emph{P \textgreater{} 0.05} ) by the solvent type but
affected (\emph{P \textless{} 0.05} ) by the extraction process. The
intensity of the peak at around 1600 cm\textsuperscript{-1} was lower
with ball milling as compared to traditional extraction. This was
probably related to the amount of phospholipid compounds extracted and
potentially improve the stability of oil bodies. The intensity of the
peak around 2800-2900 cm\textsuperscript{-1} decreased with ball mill
treatment. This can be explained by protein-polysaccharide interaction.
Ball mill treatment increased the amount of released compounds into the
solvent matrix. Among these, soluble polysaccharides became more
available for intermolecular interactions with proteins. These
interactions were seen as reduced intensity of spectra around 2800-2900
cm\textsuperscript{-1}representing glycosidic bond between amino group
of protein and carboxylic group of polysaccharides. This may prove the
formation of protein-polysaccharide complex (Guerrero et al., 2014).

Particle size and zeta potential are important factors that relate to
their dispersibility and stability. When oleoresins dispersed in an
aqueous environment without additional surfactants, they showed
remarkable homogeneity and stability. The particle size of oleoresins
ranged between 323-1760 nm (Figure 4A). Both solvent type and ball mill
treatment significantly (\emph{P \textless{} 0.05} ) affected the
particle size. With traditional extraction, the particle size decreased
from a max of 1760 nm to 575 nm when dichloromethane and
IL\textsubscript{2} used, respectively (Fig. 4). This showed that
charged groups in ionic liquids were anchored on the interface of oil
bodies that resulted in increased electrostatic repulsion and reduced
the average particle size (Liu et al., 2020). The ball mill process
reduced the average particle size of oleoresins. For instance, the
average particle size was reduced by nearly 50\% when ball mill
treatment was applied using ethanol compared to conventional method. It
was observed that the friction and shear forces during ball milling
treatment reduced the particle size. This can be explained in
consideration of the FTIR analysis. For oleoresin dispersions of lower
particle size, the intensity of the FTIR band at 1100
cm\textsuperscript{-1}, 1600 cm\textsuperscript{-1} and 2800-2900
cm\textsuperscript{-1} increased. In addition, the zeta potential was
measured as an indicator of the stability and extent of charged
polymers, mainly protein fraction of oleosome structure. The results
ranged from -8 mV to -35 mV (Fig 4B). In parallel to the particle size
data, small particles from ball mill extracts showed higher zeta
potential values, which demonstrate greater physical stability. The low
molecular weight oleosins as major protein fraction plays critical role
in the stability of the oleoresin dispersions. due to their hydrophobic
nature, oleosins can penetrate deep into the triacylglycerol core of
their emulsions with large detachment energies that reinforce their
integrity and stability (Wijesundera \& Shen, 2014). Another protein
fraction, caleosins have shorter hydrophobic sequence and longer
hydrophilic unit as compared to oleosin with special N-terminal segments
bearing single Ca\textsuperscript{2+} ions responsible for the change in
the polarity (Hanano et al., 2023). The difference in the smaller
caleosin content of the oleoresins were probably responsible for the
formation of smaller particle size as expected with higher diffusion
rate of smaller polymers, and the higher zeta potential observed for
them.

\textbf{Conclusions}

Our results are original to demonstrate the potential of oleoresins
obtained from sorghum grain for value-added food applications. The
oleoresins are rich in polyphenols with strong antioxidant potential as
expected related to characteristics of the sorghum grain. The
composition and structural properties of the oleoresins can be modulated
by using novel ILs with composite anions and cations. Therefore, ILs can
offer great potential for clean and controlled extraction of oleoresins
as compared to traditional solvent extraction. Moreover, the wet milling
process via the use of ball mill can help to break solid enclosure to
improve extraction yield, and at the same time improve protein
functionality for higher emulsification power.

\textbf{Acknowledgements}

This research was partially supported by the Kansas Agricultural
Experiment Station (KAES) and by the U.S. Department of Agriculture
(award number 2020-67013-30897).

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\textbf{Tables}

\textbf{Table 1.} Total protein (wt\%), total lipid (wt\%) and phenolic
(mg GAE/g) contents of oleoresins extracted from sorghum grain using
different methods. The results are expressed as the mean ± standard
deviation. The lower and upper superscripts indicate the significant
differences between the solvent type for conventional solvent or ball
mill-assisted extraction processes, respectively. The Roman numerals
show the differences between the type of extraction for each solvent.\selectlanguage{english}
\begin{longtable}[]{@{}llllllllllllllllll@{}}
\toprule
\begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\textbf{Conventional extraction}\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\textbf{Conventional extraction}\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\textbf{Conventional extraction}\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\textbf{Conventional extraction}\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\textbf{Conventional extraction}\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\textbf{Ball milling}\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\textbf{Ball milling}\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\textbf{Ball milling}\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\textbf{Ball milling}\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\textbf{Ball milling}\strut
\end{minipage} & \begin{minipage}[b]{0.03\columnwidth}\raggedright\strut
\textbf{Ball milling}\strut
\end{minipage}\tabularnewline
\midrule
\endhead
\begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
\textbf{Solvent type}\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total protein (wt \%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total protein (wt \%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total protein (wt \%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total lipid content (wt \%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total lipid content (wt \%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total lipid content (wt \%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total lipid content (wt \%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total phenolic content (mg GAE/g)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total phenolic content (mg GAE/g)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total protein (wt\%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total protein (wt\%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total protein (wt\%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total lipid content (wt\%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total lipid content (wt\%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total lipid content (wt\%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total lipid content (wt\%)\strut
\end{minipage} & \begin{minipage}[t]{0.05\columnwidth}\raggedright\strut
Total phenolic content (mg GAE/g)\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
IL\textsubscript{1}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
IL\textsubscript{1}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
0.67 \selectlanguage{ngerman}± 0.03\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
0.67 \selectlanguage{ngerman}± 0.03\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
0.67 \selectlanguage{ngerman}± 0.03\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
69.22 \selectlanguage{ngerman}± 0.04\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
69.22 \selectlanguage{ngerman}± 0.04\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
69.22 \selectlanguage{ngerman}± 0.04\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
69.22 \selectlanguage{ngerman}± 0.04\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
48 \selectlanguage{ngerman}± 0.01\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
48 \selectlanguage{ngerman}± 0.01\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
1.37 \selectlanguage{ngerman}±0.05\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
1.37 \selectlanguage{ngerman}±0.05\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
1.37 \selectlanguage{ngerman}±0.05\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
82.19\selectlanguage{ngerman}±0.07\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
57 \selectlanguage{ngerman}± 0.01\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
57 \selectlanguage{ngerman}± 0.01\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
57 \selectlanguage{ngerman}± 0.01\textsuperscript{A,II}\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
IL\textsubscript{2}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
IL\textsubscript{2}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
0.58 \selectlanguage{ngerman}± 0.01\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
0.58 \selectlanguage{ngerman}± 0.01\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
0.58 \selectlanguage{ngerman}± 0.01\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
66.33\selectlanguage{ngerman}± 0.06\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
66.33\selectlanguage{ngerman}± 0.06\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
66.33\selectlanguage{ngerman}± 0.06\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
66.33\selectlanguage{ngerman}± 0.06\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
42 \selectlanguage{ngerman}± 0.01\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
42 \selectlanguage{ngerman}± 0.01\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
1.32 \selectlanguage{ngerman}±0.06\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
1.32 \selectlanguage{ngerman}±0.06\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
1.32 \selectlanguage{ngerman}±0.06\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
80.26\selectlanguage{ngerman}±0.08\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
52 \selectlanguage{ngerman}± 0.02\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
52 \selectlanguage{ngerman}± 0.02\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
52 \selectlanguage{ngerman}± 0.02\textsuperscript{A,II}\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
dichloromethane (GC grade, 99\%)\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
dichloromethane (GC grade, 99\%)\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
0.36 \selectlanguage{ngerman}± 0.02\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
0.36 \selectlanguage{ngerman}± 0.02\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
0.36 \selectlanguage{ngerman}± 0.02\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
57.26 \selectlanguage{ngerman}± 0.02\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
57.26 \selectlanguage{ngerman}± 0.02\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
57.26 \selectlanguage{ngerman}± 0.02\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
57.26 \selectlanguage{ngerman}± 0.02\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
29 \selectlanguage{ngerman}± 0.02\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
29 \selectlanguage{ngerman}± 0.02\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
1.06 \selectlanguage{ngerman}±0.01\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
1.06 \selectlanguage{ngerman}±0.01\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
1.06 \selectlanguage{ngerman}±0.01\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
76.32 \selectlanguage{ngerman}±0.04\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
76.32 \selectlanguage{ngerman}±0.04\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
32 \selectlanguage{ngerman}± 0.01\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
32 \selectlanguage{ngerman}± 0.01\textsuperscript{B,II}\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
ethanol (GC grade, 99\%)\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
ethanol (GC grade, 99\%)\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
0.43 \selectlanguage{ngerman}± 0.01\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
0.43 \selectlanguage{ngerman}± 0.01\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
0.43 \selectlanguage{ngerman}± 0.01\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
53.12 \selectlanguage{ngerman}± 0.08\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
53.12 \selectlanguage{ngerman}± 0.08\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
53.12 \selectlanguage{ngerman}± 0.08\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
53.12 \selectlanguage{ngerman}± 0.08\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
21 \selectlanguage{ngerman}± 0.02\textsuperscript{d,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
21 \selectlanguage{ngerman}± 0.02\textsuperscript{d,I}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
1.15 \selectlanguage{ngerman}± 0.11\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
1.15 \selectlanguage{ngerman}± 0.11\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
1.15 \selectlanguage{ngerman}± 0.11\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
70.41 \selectlanguage{ngerman}± 0.09\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
70.41 \selectlanguage{ngerman}± 0.09\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
28 \selectlanguage{ngerman}± 0.02\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.03\columnwidth}\raggedright\strut
28 \selectlanguage{ngerman}± 0.02\textsuperscript{C,II}\strut
\end{minipage}\tabularnewline
\bottomrule
\end{longtable}\selectlanguage{ngerman}

\textbf{Table 2.} Fatty acid composition (wt\%) in oleoresins extracted
from sorghum grain using different methods. The results are expressed as
the mean ± standard deviation. The lower and upper superscripts indicate
the significant differences between the solvent type for conventional
solvent or ball mill-assisted extraction processes, respectively. The
Roman numerals show the differences between the type of extraction for
each solvent.\selectlanguage{english}
\begin{longtable}[]{@{}llllllllllllllll@{}}
\toprule
\begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
\textbf{Solvent type}\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Myristic acid (C14)\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Myristic acid (C14)\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Myristic acid (C14)\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Myristic acid (C14)\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Palmitic acid (C16)\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Palmitic acid (C16)\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Palmitoleic acid (C16:1 ([?]9))\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Palmitoleic acid (C16:1 ([?]9))\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Octadecanoic acid (C18:0)\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Octadecanoic acid (C18:0)\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Octadecanoic acid (C18:0)\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Oleic acid (C18:1 \selectlanguage{greek}ω\selectlanguage{english}9-cis)\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Elaidic acid (C18:1 \selectlanguage{greek}ω\selectlanguage{english}9-trans)\strut
\end{minipage} & \begin{minipage}[b]{0.06\columnwidth}\raggedright\strut
Linoleic acid (C18:2)\strut
\end{minipage}\tabularnewline
\midrule
\endhead
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
Conventional extraction\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
IL\textsubscript{1}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
32.946 \selectlanguage{ngerman}±0.003\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
32.946 \selectlanguage{ngerman}±0.003\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
16.819\selectlanguage{ngerman}±0.675\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
16.819\selectlanguage{ngerman}±0.675\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
16.819\selectlanguage{ngerman}±0.675\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
16.819\selectlanguage{ngerman}±0.675\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
16.819\selectlanguage{ngerman}±0.675\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
16.188 \selectlanguage{ngerman}± 0.292\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
16.188 \selectlanguage{ngerman}± 0.292\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
1.646 \selectlanguage{ngerman}±0.172\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
1.646 \selectlanguage{ngerman}±0.172\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
17.249 \selectlanguage{ngerman}± 0.329\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
1.553 \selectlanguage{ngerman}± 0.115\textsuperscript{d,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.599 \selectlanguage{ngerman}± 1.202\textsuperscript{a,I}\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
IL\textsubscript{2}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
32.888 \selectlanguage{ngerman}±0.006\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
32.888 \selectlanguage{ngerman}±0.006\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
17.240 \selectlanguage{ngerman}±0.723\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
17.240 \selectlanguage{ngerman}±0.723\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
17.240 \selectlanguage{ngerman}±0.723\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
17.240 \selectlanguage{ngerman}±0.723\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
17.240 \selectlanguage{ngerman}±0.723\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.855 \selectlanguage{ngerman}±0.265\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.855 \selectlanguage{ngerman}±0.265\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
1.577 \selectlanguage{ngerman}± 0.126\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
1.577 \selectlanguage{ngerman}± 0.126\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
15.619 \selectlanguage{ngerman}± 0.215\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
6.465 \selectlanguage{ngerman}±0.137\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.356 \selectlanguage{ngerman}± 1.047\textsuperscript{a,I}\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
dichloromethane (99\%)\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
30.959 \selectlanguage{ngerman}±0.018\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
30.959 \selectlanguage{ngerman}±0.018\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
15.758\selectlanguage{ngerman}±0.231\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
15.758\selectlanguage{ngerman}±0.231\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
15.758\selectlanguage{ngerman}±0.231\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
15.758\selectlanguage{ngerman}±0.231\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
15.758\selectlanguage{ngerman}±0.231\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
10.411 \selectlanguage{ngerman}±0.261\textsuperscript{ab,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
10.411 \selectlanguage{ngerman}±0.261\textsuperscript{ab,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
7.482 \selectlanguage{ngerman}± 0.212\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
7.482 \selectlanguage{ngerman}± 0.212\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.141 \selectlanguage{ngerman}± 0.243\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
10.439 \selectlanguage{ngerman}± 0.317\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
11.81 \selectlanguage{ngerman}± 1.082\textsuperscript{c,I}\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
ethanol (99\%)\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
31.582\selectlanguage{ngerman}±0.004\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
31.582\selectlanguage{ngerman}±0.004\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.983 \selectlanguage{ngerman}±0.277\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.983 \selectlanguage{ngerman}±0.277\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.983 \selectlanguage{ngerman}±0.277\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.983 \selectlanguage{ngerman}±0.277\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.983 \selectlanguage{ngerman}±0.277\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
8.130 \selectlanguage{ngerman}± 0.266\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
8.130 \selectlanguage{ngerman}± 0.266\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
8.130 \selectlanguage{ngerman}± 0.266\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
9.993 \selectlanguage{ngerman}±0.173\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
14.704 \selectlanguage{ngerman}± 0.211\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
9.586 \selectlanguage{ngerman}±0.122\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.022 \selectlanguage{ngerman}±0.937\textsuperscript{b,I}\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
Ball mill\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
IL\textsubscript{1}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
26.064\selectlanguage{ngerman}±0.006\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
26.064\selectlanguage{ngerman}±0.006\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.058\selectlanguage{ngerman}±0.007\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.058\selectlanguage{ngerman}±0.007\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.058\selectlanguage{ngerman}±0.007\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.058\selectlanguage{ngerman}±0.007\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.058\selectlanguage{ngerman}±0.007\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
19.275 \selectlanguage{ngerman}± 0.477\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
19.275 \selectlanguage{ngerman}± 0.477\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
19.275 \selectlanguage{ngerman}± 0.477\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
1.792\selectlanguage{ngerman}±0.002\textsuperscript{C,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
23.663 \selectlanguage{ngerman}± 0.003\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.499 \selectlanguage{ngerman}± 0.017\textsuperscript{D,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.649 \selectlanguage{ngerman}±0.025\textsuperscript{A,I}\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
IL\textsubscript{2}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
26.402\selectlanguage{ngerman}±0.041\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
26.402\selectlanguage{ngerman}±0.041\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
26.402\selectlanguage{ngerman}±0.041\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
11.478 \selectlanguage{ngerman}± 0.69\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
11.478 \selectlanguage{ngerman}± 0.69\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
11.478 \selectlanguage{ngerman}± 0.69\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
11.478 \selectlanguage{ngerman}± 0.69\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
19.717 \selectlanguage{ngerman}± 0.291\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
19.717 \selectlanguage{ngerman}± 0.291\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
19.717 \selectlanguage{ngerman}± 0.291\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
1.723\selectlanguage{ngerman}±0.233\textsuperscript{C,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
22.787 \selectlanguage{ngerman}± 0.891\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.338 \selectlanguage{ngerman}± 1.711\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.555 \selectlanguage{ngerman}± 1.7\textsuperscript{A,I}\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
dichloromethane (99\%)\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
21.868\selectlanguage{ngerman}±0.043\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
21.868\selectlanguage{ngerman}±0.043\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
21.868\selectlanguage{ngerman}±0.043\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
9.836\selectlanguage{ngerman}±0.674\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
9.836\selectlanguage{ngerman}±0.674\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
9.836\selectlanguage{ngerman}±0.674\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
9.836\selectlanguage{ngerman}±0.674\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
18.290 \selectlanguage{ngerman}± 0.281\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
18.290 \selectlanguage{ngerman}± 0.281\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
18.290 \selectlanguage{ngerman}± 0.281\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
8.637\selectlanguage{ngerman}±0.347\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
20.427 \selectlanguage{ngerman}± 0.876\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
8.654 \selectlanguage{ngerman}± 1.887\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.288 \selectlanguage{ngerman}±1.336\textsuperscript{B,I}\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
ethanol (99\%)\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
23.491\selectlanguage{ngerman}±0.005\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
23.491\selectlanguage{ngerman}±0.005\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
23.491\selectlanguage{ngerman}±0.005\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
8.203\selectlanguage{ngerman}±0.007\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
8.203\selectlanguage{ngerman}±0.007\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
8.203\selectlanguage{ngerman}±0.007\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
8.203\selectlanguage{ngerman}±0.007\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
17.633 \selectlanguage{ngerman}± 0.456\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
17.633 \selectlanguage{ngerman}± 0.456\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
17.633 \selectlanguage{ngerman}± 0.456\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
10.638\selectlanguage{ngerman}±0.188\textsuperscript{A,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
18.990\selectlanguage{ngerman}±0.371\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
7.432 \selectlanguage{ngerman}± 1.112\textsuperscript{B, II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.613 \selectlanguage{ngerman}± 1.13\textsuperscript{A, I}\strut
\end{minipage}\tabularnewline
\bottomrule
\end{longtable}\selectlanguage{ngerman}

\textbf{Table 3.} Concentration of phenolic compounds as gallic acid
equivalents (mg GAE/g oleoresin) in oleoresins extracted from sorghum
grain using different methods. The results are expressed as the mean ±
standard deviation. The lower and upper superscripts indicate the
significant differences between the solvent type for conventional
solvent or ball mill-assisted extraction processes, respectively. The
Roman numerals show the differences between the type of extraction for
each solvent.\selectlanguage{english}
\begin{longtable}[]{@{}lllllllllllllllll@{}}
\toprule
\begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
\textbf{Solvent type}\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
Caffeic acid\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
Coumaric acid\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
Ferulic acid\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
Ferulic acid\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
Apigenidin\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
Apigenidin\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
Luteolinidin\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
Luteolinidin\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
7-methoxy apicidinin\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
7-methoxy apicidinin\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
7-methoxy apicidinin\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
Eriodictyol\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
Eriodictyol\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
Narencenin\strut
\end{minipage} & \begin{minipage}[b]{0.04\columnwidth}\raggedright\strut
Narencenin\strut
\end{minipage}\tabularnewline
\midrule
\endhead
\begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
Conventional extraction\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
IL\textsubscript{1}\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.06\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
20.280 \selectlanguage{ngerman}± 0.007\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
18.409 \selectlanguage{ngerman}± 0.003\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
10.456 \selectlanguage{ngerman}± 0.058\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
10.456 \selectlanguage{ngerman}± 0.058\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
9.556 \selectlanguage{ngerman}± 0.003\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
9.556 \selectlanguage{ngerman}± 0.003\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.673 \selectlanguage{ngerman}± 0.017\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.673 \selectlanguage{ngerman}± 0.017\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.673 \selectlanguage{ngerman}± 0.017\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
8.360 \selectlanguage{ngerman}± 0.08\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
8.360 \selectlanguage{ngerman}± 0.08\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.032 \selectlanguage{ngerman}± 0.005\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
5.061 \selectlanguage{ngerman}± 0.008\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
5.061 \selectlanguage{ngerman}± 0.008\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
IL\textsubscript{2}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
19.208 \selectlanguage{ngerman}± 0.051\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.602 \selectlanguage{ngerman}± 0.321\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
10.446 \selectlanguage{ngerman}± 0.291\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
10.446 \selectlanguage{ngerman}± 0.291\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
6.319 \selectlanguage{ngerman}± 1.112\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
6.319 \selectlanguage{ngerman}± 1.112\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
10.380 \selectlanguage{ngerman}± 2.67\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
10.380 \selectlanguage{ngerman}± 2.67\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
10.380 \selectlanguage{ngerman}± 2.67\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
6.470 \selectlanguage{ngerman}± 1.342\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
6.470 \selectlanguage{ngerman}± 1.342\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.158 \selectlanguage{ngerman}± 0.375\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.658 \selectlanguage{ngerman}± 0.551\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.658 \selectlanguage{ngerman}± 0.551\textsuperscript{a,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
dichloromethane\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
11.599 \selectlanguage{ngerman}± 0.053\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
10.651 \selectlanguage{ngerman}± 0.331\textsuperscript{d,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.113 \selectlanguage{ngerman}± 0.281\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.113 \selectlanguage{ngerman}± 0.281\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.096 \selectlanguage{ngerman}± 1.171\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.096 \selectlanguage{ngerman}± 1.171\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.251 \selectlanguage{ngerman}± 0.015\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.251 \selectlanguage{ngerman}± 0.015\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.251 \selectlanguage{ngerman}± 0.015\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.405 \selectlanguage{ngerman}± 0.371\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.405 \selectlanguage{ngerman}± 0.371\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.085 \selectlanguage{ngerman}± 0.241\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.549 \selectlanguage{ngerman}± 0.623\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.549 \selectlanguage{ngerman}± 0.623\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
ethanol (99\%)\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
14.296 \selectlanguage{ngerman}± 0.007\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
11.385 \selectlanguage{ngerman}± 0.038\textsuperscript{c,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.315 \selectlanguage{ngerman}± 0.456\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.315 \selectlanguage{ngerman}± 0.456\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.374 \selectlanguage{ngerman}± 0.562\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.374 \selectlanguage{ngerman}± 0.562\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
6.023 \selectlanguage{ngerman}±2.131\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
6.023 \selectlanguage{ngerman}±2.131\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
6.023 \selectlanguage{ngerman}±2.131\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.486 \selectlanguage{ngerman}± 0.461\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.486 \selectlanguage{ngerman}± 0.461\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.177 \selectlanguage{ngerman}±0.563\textsuperscript{ab,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.685 \selectlanguage{ngerman}± 0.082\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.685 \selectlanguage{ngerman}± 0.082\textsuperscript{b,I}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
Ball mill\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
IL\textsubscript{1}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
26.147 \selectlanguage{ngerman}± 0.005\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
22.965 \selectlanguage{ngerman}± 0.075\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
6.082 \selectlanguage{ngerman}± 0.292\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
6.082 \selectlanguage{ngerman}± 0.292\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.360 \selectlanguage{ngerman}± 0.081\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
12.360 \selectlanguage{ngerman}± 0.081\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.111 \selectlanguage{ngerman}± 1.332\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.111 \selectlanguage{ngerman}± 1.332\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.111 \selectlanguage{ngerman}± 1.332\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.486 \selectlanguage{ngerman}±0.713\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.486 \selectlanguage{ngerman}±0.713\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.575 \selectlanguage{ngerman}±0.211\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.272 \selectlanguage{ngerman}± 0.836\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.272 \selectlanguage{ngerman}± 0.836\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
IL\textsubscript{2}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
26.075 \selectlanguage{ngerman}± 0.005\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
20.159 \selectlanguage{ngerman}± 0.492\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
6.072 \selectlanguage{ngerman}± 0.265\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
6.072 \selectlanguage{ngerman}± 0.265\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
11.927 \selectlanguage{ngerman}± 0.064\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
11.927 \selectlanguage{ngerman}± 0.064\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.271 \selectlanguage{ngerman}± 2.671\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.271 \selectlanguage{ngerman}± 2.671\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.271 \selectlanguage{ngerman}± 2.671\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.606 \selectlanguage{ngerman}±0.136\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.606 \selectlanguage{ngerman}±0.136\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.312 \selectlanguage{ngerman}±0.429\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
2.885 \selectlanguage{ngerman}± 0.621\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
2.885 \selectlanguage{ngerman}± 0.621\textsuperscript{A,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
dichloromethane\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
17.417 \selectlanguage{ngerman}±0.004\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
13.135 \selectlanguage{ngerman}± 0.881\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
2.175 \selectlanguage{ngerman}± 0.261\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
2.175 \selectlanguage{ngerman}± 0.261\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
9.278 \selectlanguage{ngerman}± 1.112\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
9.278 \selectlanguage{ngerman}± 1.112\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.907 \selectlanguage{ngerman}± 0.148\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.907 \selectlanguage{ngerman}± 0.148\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
4.907 \selectlanguage{ngerman}± 0.148\textsuperscript{C,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
2.458 \selectlanguage{ngerman}±0.722\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
2.458 \selectlanguage{ngerman}±0.722\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.145 \selectlanguage{ngerman}±0.255\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
1.638 \selectlanguage{ngerman}± 1.92\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
1.638 \selectlanguage{ngerman}± 1.92\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
ethanol (99\%)\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
19.720 \selectlanguage{ngerman}±0.002\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
18.869 \selectlanguage{ngerman}± 0.320\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.376 \selectlanguage{ngerman}± 0.266\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.376 \selectlanguage{ngerman}± 0.266\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
11.321 \selectlanguage{ngerman}± 0.562\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
11.321 \selectlanguage{ngerman}± 0.562\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
11.321 \selectlanguage{ngerman}± 0.562\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
9.497 \selectlanguage{ngerman}±0.156\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
9.497 \selectlanguage{ngerman}±0.156\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
2.540 \selectlanguage{ngerman}±0.211\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
2.540 \selectlanguage{ngerman}±0.211\textsuperscript{B,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
3.237\selectlanguage{ngerman}±0.471\textsuperscript{AB,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
1.773 \selectlanguage{ngerman}± 0.825\textsuperscript{AB,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
1.773 \selectlanguage{ngerman}± 0.825\textsuperscript{AB,II}\strut
\end{minipage} & \begin{minipage}[t]{0.04\columnwidth}\raggedright\strut
\strut
\end{minipage}\tabularnewline
\bottomrule
\end{longtable}

\textbf{Legends to the Figures}

\textbf{Figure 1.} Oleoresin extraction yield (\%) from sorghum grain as
a function of extraction condition. The results are expressed as the
mean of 3 replicates and standard deviation (bars). The lower and upper
superscripts indicate the significant differences between the solvent
type for conventional solvent or ball mill-assisted extraction
processes, respectively. The Roman numerals show the differences between
the type of extraction for each solvent.

\textbf{Figure 2.} FTIR spectra of oleoresins obtained from sorghum
grain with different extraction conditions. The arrows indicate bond
stretching of interest.

\textbf{Figure 3.} Particle size (A) and zeta potential (B) of oleoresin
dispersions from sorghum grain as a function of extraction condition.
The results are expressed as the mean of 3 replicates and standard
deviation (bars). The lower and upper superscripts indicate the
significant differences between the solvent type for conventional
solvent or ball mill-assisted extraction processes, respectively. The
Roman numerals show the differences between the type of extraction for
each solvent.

\selectlanguage{english}
\FloatBarrier
\end{document}

