A novel vicinal diepoxide of alloaureothin was isolated from Streptomyces sp. NIIST-D31 strain along with three carboxamides, p-aminobenzoic acid and 1,6-dimethoxyphenazine. Exhaustive 2D NMR analysis and analysis of experimental, theoretical CD spectra aided in establishing the structure of compound 1. Compound 1 inhibits adipogenesis and accumulation of lipid droplets during the differentiation of 3T3-L1 cells.
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Fullas F, Brown DM, Wani MC, Wall MR, Chagwedera TE, Farnsworth NR, et al. Gummiferol, a cytotoxic polyacetylene from the leaves of Adenia gummifera. J Nat Products. 1995;58:1625–8.
Gerwick WH, Fenical W, van Engen D, Clardy J. Isolation and structure of spatol, a potent inhibitor of cell replication from the brown seaweed Spatoglossum schmittii. J Am Chem Soc. 1980;102:7991–3.
Chen J, Chen J, Sun Y, Yan Y, Kong L, Li Y, et al. Cytotoxic Triterpenoids from Azadirachta indica. Planta Med. 2011;77:1844–7.
Chianese G, Yu H-B, Yang F, Sirignano C, Luciano P, Han B-N, et al. PPAR modulating polyketides from a Chinese Plakortis simplex and clues on the origin of their chemodiversity. J Org Chem. 2016;81:5135–43.
Díaz-Marrero AR, Cueto M, D’Croz L, Darias J. Validating an endoperoxide as a key intermediate in the biosynthesis of Elysiapyrones. Org Lett. 2008;10:3057–60.
Murray V, Moore AG, Matias C, Wickham G. The interaction of hedamycin and DC92-B in a sequence selective manner with DNA in intact human cells. Biochimica et Biophysica Acta (BBA) - Gene Struct Expr. 1995;1261:195–200.
Yasuzawa T, Saitoh Y, Sano H. Structures of the novel anthraquinone antitumor antibiotics, DC92-B and DC92-D. J Antibiotics. 1990;43:485–91.
Sato Y, Watabe H-O, Nakazawa T, Shomura T, Yamamoto H, Sezaki M, et al. Ankinomycin, a potent antitumor antibiotic. J Antibiotics. 1989;42:149–52.
Kawai Y, Furihata K, Seto H, Otake N. The structure of a new antibiotic, chromoxymycin. Tetrahedron Lett. 1985;26:3273–6.
Becke AD. Density‐functional thermochemistry. III. The role of exact exchange. J Chem Phys. 1993;98:5648–52.
Runge E, Gross EKU. Density-functional theory for time-dependent systems. Phys Rev Lett. 1984;52:997–1000.
Miertuš S, Scrocco E, Tomasi J. Electrostatic interaction of a solute with a continuum. A direct utilizaion of AB initio molecular potentials for the prevision of solvent effects. Chem Phys. 1981;55:117–29.
Kim H, Kim JH, Zuo G, Lim SS. Anti‐obesity effect of Melandrium firmum Rohrbach extract in 3T3‐L1 cells and high‐fat diet‐induced obese C57BL/6N mice. Food Sci Nutr. 2020;8:2251–61.
Poornima MS, Sindhu G, Billu A, Sruthi CR, Nisha P, Gogoi P, et al. Pretreatment of hydroethanolic extract of Dillenia indica L. attenuates oleic acid induced NAFLD in HepG2 cells via modulating SIRT-1/p-LKB-1/AMPK, HMGCR & PPAR-α signaling pathways. J Ethnopharmacol. 2022;292:115237.
Yang P-C, Mahmood T. Western blot: Technique, theory, and trouble shooting. North Am J Med Sci. 2012;4:429.
Ueda J, Hashimoto J, Nagai A, Nakashima T, Komaki H, Anzai K, et al. New aureothin derivative, alloaureothin, from streptomyces sp. MM23. J Antibiotics. 2007;60:321–4.
Padula D, Pescitelli G. How and how much molecular conformation affects electronic circular dichroism: the case of 1,1-Diarylcarbinols. Molecules. 2018;23:128.
Chen G, Gao H, Tang J, Huang Y, Chen Y, Wang Y, et al. Benzamides and quinazolines from a mangrove actinomycetes streptomyces sp. (No. 061316) and their inhibiting Caspase-3 catalytic activity in vitro. Chem Pharm Bull. 2011;59:447–51.
Yang X, Peng T, Yang Y, Li W, Xiong J, Zhao L, et al. Antimicrobial and antioxidant activities of a new benzamide from endophytic Streptomyces sp. YIM 67086. Nat Prod Res. 2015;29:331–5.
Zhang X, Shu C, Li Q, Lian XY, Zhang Z. Novel cyclohexene and benzamide derivatives from marine-associated Streptomyces sp. ZZ502. Nat Prod Res. 2019;33:2151–9.
Shaaban KA, Shepherd MD, Ahmed TA, Nybo SE, Leggas M, Rohr J. Pyramidamycins A-D and 3-hydroxyquinoline-2-carboxamide; Cytotoxic benzamides from Streptomyces sp. DGC1. J Antibiotics. 2012;65:615–22.
Chu MJ, Tang XL, Qin GF, Sun YT, Li L, de Voogd NJ, et al. Pyrrole derivatives and diterpene alkaloids from the South China Sea Sponge Agelas nakamurai. Chem Biodivers. 2017; 14. https://doi.org/10.1002/cbdv.201600446.
Shaaban KA, Saunders MA, Zhang Y, Tran T, Elshahawi SI, Ponomareva L. et al. Spoxazomicin D and Oxachelin C, potent neuroprotective carboxamides from the appalachian coal fire-associated isolate Streptomyces sp. RM-14-6 J Nat Prod. 2017;80:2–11.
König G, Wright A. Two new naturally occurring pyrrole derivatives from the tropical marine sponge Agelas Oroides. Nat Prod Lett. 1994;5:141–6.
Hamm JK, el Jack AK, Pilch PF, Farmer SR. Role of PPARgamma in regulating adipocyte differentiation and insulin-responsive glucose uptake. Ann N. Y Acad Sci. 1999;892:134–45.
Li KK, Liu CL, Shiu HT, Wong HL, Siu WS, Zhang C, et al. Cocoa tea (Camellia ptilophylla) water extract inhibits adipocyte differentiation in mouse 3T3-L1 preadipocytes. Sci Rep. 2016;6:20172.
Choi R-Y, Lee H-I, Ham JR, Yee S-T, Kang K-Y, Lee M-K. Heshouwu (Polygonum multiflorum Thunb.) ethanol extract suppresses pre-adipocytes differentiation in 3T3-L1 cells and adiposity in obese mice. Biomed Pharmacother. 2018;106:355–62.
Shyni GL, Sajin KF, Mangalam SN, Raghu KG. An in vitro study reveals the anti-obesity effects of 7- methoxy-3-methyl-5-((E)-prop-1-enyl)-2-(3,4,5-trimethoxyphenyl)-2,3-dihydrobenzofuran from Myristica fragrans. Eur J Pharmacol. 2021;891:173686.
Financial support from DST, Science, and Engineering Research Board, India (Grant number: CRG/2020/004993) is gratefully acknowledged. TD, DKI, MSP, and ARSJ are grateful to UGC and CSIR for senior research fellowship.
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Drissya, T., Induja, D.K., Poornima, M.S. et al. A novel aureothin diepoxide derivative from Streptomyces sp. NIIST-D31 strain. J Antibiot 75, 491–497 (2022). https://doi.org/10.1038/s41429-022-00547-1
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