Antitumor assays
The in vitro cytotoxic activities of LOBs were evaluated against four tumor cell lines, SF-268 (human glioma cell line), HepG2 (human liver carcinoma cell line), MCF-7 (human breast adenocarcinoma cell line) and A549 (human lung adenocarcinoma cell) by the SRB method.[29] The assays were performed as the same way previously described.[13]
Supporting Information
The supporting information for this article is available on the WWW under https://doi.org/10.1002/cjoc.2021xxxxx.
Acknowledgement
This work is supported in part by the National Natural Science Foundation of China (22193072, 32100045, 31770062, and 42176127); Key Science and Technology Project of Hainan Province (ZDKJ202018); MOST (2018YFA0901903); K.C. Wong Education Foundation (GJTD-2020-12); the Guangdong Provincial Special Fund for Marine Economic Development Project (GDNRC[2021]48); and the Science and Technology Planning Project of Guangzhou (202102020471). Bin Tan acknowledges the support of the Special Research Assistant Project of CAS. We thank Prof. Shengying Li (Shandong University) for the gift of plasmids pET28b-fdx-1499 and pET28b-fdR-0978. We are grateful to Dr. Z. H. Xiao, X. H. Zheng, A. J. Sun, Y. Zhang and X. Ma in the equipment public service center at SCSIO for recording spectroscopic data. We also thank the data archive support from the National Earth System Data Center, National Science & Technology Infrastructure of China (http://www.geodata.cn)
References
[1] Lacoske, M. H.; Theodorakis, E. A., Spirotetronate polyketides as leads in drug discovery. J. Nat. Prod. 2015,78 , 562-575.
[2] Jiang, Z. D.; Jensen, P. R.; Fenical, W., Lobophorins A and B, new antiinflammatory macrolides produced by a tropical marine bacterium.Bioorg. Med. Chem. Lett. 1999, 9, 2003-2006. [3] Wei, R. B.; Xi, T.; Li, J.; Wang, P.; Li, F. C.; Lin, Y. C.; Qin, S., Lobophorin C and D, new kijanimicin derivatives from a marine sponge-associated Actinomycetal strain AZS17. Mar. Drugs2011, 9, 359-368. [4] Niu, S.; Li, S.; Chen, Y.; Tian, X.; Zhang, H.; Zhang, G.; Zhang, W.; Yang, X.; Zhang, S.; Ju, J.; Zhang, C., Lobophorins E and F, new spirotetronate antibiotics from a South China Sea-derivedStreptomyces sp. SCSIO 01127. J. Antibiot. 2011,64, 711-716. [5] Chen, C. X.; Wang, J.; Guo, H.; Hou, W. Y.; Yang, N.; Ren, B.; Liu, M.; Dai, H. Q.; Liu, X. T.; Song, F. H.; Zhang, L. X., Three antimycobacterial metabolites identified from a marine-derivedStreptomyces sp MS100061. Appl. Microbiol. Biot.2013, 97, 3885-3892. [6] Pan, H. Q.; Zhang, S. Y.; Wang, N.; Li, Z. L.; Hua, H. M.; Hu, J. C.; Wang, S. J., New Spirotetronate Antibiotics, Lobophorins H and I, from a South China Sea-Derived Streptomyces sp 12A35. Mar. Drugs 2013, 11, 3891-3901. [7] Cruz, P. G.; Fribley, A. M.; Miller, J. R.; Larsen, M. J.; Schultz, P. J.; Jacob, R. T.; Tamayo-Castillo, G.; Kaufman, R. J.; Sherman, D. H., Novel lobophorins inhibit oral cancer cell growth and induce Atf4- and chop-dependent cell death in murine fibroblasts.ACS Med. Chem. Lett. 2015, 6, 877-881. [8] Xiao, J.; Zhang, Q.; Zhu, Y.; Li, S.; Zhang, G.; Zhang, H.; Saurav, K.; Zhang, C., Characterization of the sugar-O-methyltransferase LobS1 in lobophorin biosynthesis. Appl. Microbiol. Biotechnol.2013, 97, 9043-9053. [9] Li, S. M.; Xiao, J.; Zhu, Y. G.; Zhang, G. T.; Yang, C. F.; Zhang, H. B.; Ma, L.; Zhang, C. S., Dissecting glycosylation steps in lobophorin biosynthesis implies an iterative glycosyltransferase.Org. Lett. 2013, 15, 1374-1377.
[10] Lin, Z.; Koch, M.; Pond, C. D.; Mabeza, G.; Seronay, R. A.; Concepcion, G. P.; Barrows, L. R.; Olivera, B. M.; Schmidt, E. W., Structure and activity of lobophorins from a turrid mollusk-associatedStreptomyces sp. J. Antibiot. 2014, 67 , 121-126.
[11] Song, C. P., H.; Hu, J., Isolation and identification of a new antibiotic, lobophorin J, from a deep sea-derived Streptomycessp. 12A35. Chin. J. Antibiot. 2015, 40 , 721-727.
[12] Brana, A. F.; Sarmiento-Vizcaino, A.; Osset, M.; Perez-Victoria, I.; Martin, J.; de Pedro, N.; de la Cruz, M.; Diaz, C.; Vicente, F.; Reyes, F.; Garcia, L. A.; Blanco, G., Lobophorin K, a new natural product with cytotoxic activity produced by Streptomycessp M-207 associated with the Deep-Sea coral lophelia pertusa. Mar. Drugs 2017, 15, 144.
[13] Tan, B.; Chen, S.; Zhang, Q.; Chen, Y.; Zhu, Y.; Khan, I.; Zhang, W.; Zhang, C., Heterologous expression leads to discovery of diversified lobophorin analogues and a flexible glycosyltransferase.Org. Lett. 2020, 22 , 1062-1066.
[14] Luo, M.; Tang, L.; Dong, Y.; Huang, H.; Deng, Z.; Sun, Y., Antibacterial natural products lobophorin L and M from the marine-derived Streptomyces sp. 4506. Nat. Prod. Res.2021 , 35 , 5581-5587.
[15] Xing, L.; Chang, Y.; Han, Y.; Peng, J.; Li, D.; Zhang, G.; Che, Q., Isolation and structure elucidation of lobophorin N from the South China Sea-derived Streptomyces sp. HDN1844000. Chin. J. Mar. drugs 2021, 40 , 9-15.
[16] Zhang, C.; Ding, W.; Qin, X.; Ju, J., Genome sequencing ofStreptomyces olivaceus SCSIO T05 and activated production of lobophorin CR4 via metabolic engineering and genome mining. Mar. Drugs 2019, 17 .
[17] Jia, X. Y.; Tian, Z. H.; Shao, L.; Qu, X. D.; Zhao, Q. F.; Tang, J.; Tang, G. L.; Liu, W., Genetic characterization of the chlorothricin gene cluster as a model for spirotetronate antibiotic biosynthesis. Chem. Biol. 2006, 13 , 575-85.
[18] Zhang, H.; White-Phillip, J. A.; Melancon, C. E.; Kwon, H. J.; Yu, W. L.; Liu, H. W., Elucidation of the kijanimicin gene cluster: Insights into the biosynthesis of spirotetronate antibiotics and nitrosugars. J. Am. Chem. Soc. 2007, 129 , 14670-14683.
[19] Fang, J.; Zhang, Y.; Huang, L.; Jia, X.; Zhang, Q.; Zhang, X.; Tang, G.; Liu, W., Cloning and characterization of the tetrocarcin A gene cluster from Micromonospora chalcea NRRL 11289 reveals a highly conserved strategy for tetronate biosynthesis in spirotetronate antibiotics. J. Bacteriol. 2008, 190 , 6014-25.
[20] Sun, Y.; Hong, H.; Gillies, F.; Spencer, J. B.; Leadlay, P. F., Glyceryl-S-acyl carrier protein as an intermediate in the biosynthesis of tetronate antibiotics. ChemBioChem 2008, 9 , 150-156.
[21] Wu, Q. Q.; Wu, Z. H.; Qu, X. D.; Liu, W., Insights into pyrroindomycin biosynthesis reveal a uniform paradigm for tetramate/tetronate formation. J. Am. Chem. Soc. 2012,134 , 17342-17345.
[22] Kanchanabanca, C.; Tao, W.; Hong, H.; Liu, Y.; Hahn, F.; Samborskyy, M.; Deng, Z.; Sun, Y.; Leadlay, P. F., Unusual acetylation-elimination in the formation of tetronate antibiotics.Angew. Chem. Int. Ed. 2013, 52 , 5785-5788.
[23] Hashimoto, T.; Hashimoto, J.; Teruya, K.; Hirano, T.; Shin-ya, K.; Ikeda, H.; Liu, H. W.; Nishiyama, M.; Kuzuyama, T., Biosynthesis of versipelostatin: identification of an enzyme-catalyzed [4+2]-cycloaddition required for macrocyclization of spirotetronate-containing polyketides. J. Am. Chem. Soc.2015, 137 , 572-575.
[24] Sun, Y.; Ma, L.; Han, D.; Du, L.; Qi, F.; Zhang, W.; Sun, J.; Huang, S.; Kim, E. S.; Li, S., In vitro reconstitution of the cyclosporine specific P450 hydroxylases using heterologous redox partner proteins. J. Ind. Microbiol. Biotechnol. 2017,44 , 161-166.
[25] Li, S.; Du, L.; Bernhardt, R., Redox partners: function modulators of bacterial P450 enzymes.Trends Microbiol. 2020, 28 , 445-454.
[26] Flett, F.; Mersinias, V.; Smith, C. P., High efficiency intergeneric conjugal transfer of plasmid DNA from Escherichia coli to methyl DNA-restricting streptomycetes. FEMS Microbiol. Lett. 1997, 155 , 223-229.
[27] Datsenko, K. A.; Wanner, B. L., One-step inactivation of chromosomal genes in Escherichia coli K-12 using PCR products.Proc. Natl. Acad. Sci. USA. 2000, 97 , 6640-6645.
[28] Gust, B.; Challis, G. L.; Fowler, K.; Kieser, T.; Chater, K. F., PCR-targeted Streptomyces gene replacement identifies a protein domain needed for biosynthesis of the sesquiterpene soil odor geosmin. Proc. Natl. Acad. Sci. USA. 2003, 100 , 1541-1546.
[29] Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney, S.; Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst.1990, 82 , 1107-1112.