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A novel aureothin diepoxide derivative from Streptomyces sp. NIIST-D31 strain

The Journal of Antibiotics volume 75, pages 491–497 (2022)Cite this article

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Abstract

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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References

  1. 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.

    Article  CAS  Google Scholar 

  2. 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.

    Article  CAS  Google Scholar 

  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.

    Article  CAS  Google Scholar 

  4. 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.

    Article  CAS  Google Scholar 

  5. 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.

    Article  Google Scholar 

  6. 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.

    Article  Google Scholar 

  7. Yasuzawa T, Saitoh Y, Sano H. Structures of the novel anthraquinone antitumor antibiotics, DC92-B and DC92-D. J Antibiotics. 1990;43:485–91.

    Article  CAS  Google Scholar 

  8. 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.

    Article  CAS  Google Scholar 

  9. Kawai Y, Furihata K, Seto H, Otake N. The structure of a new antibiotic, chromoxymycin. Tetrahedron Lett. 1985;26:3273–6.

    Article  CAS  Google Scholar 

  10. Becke AD. Density‐functional thermochemistry. III. The role of exact exchange. J Chem Phys. 1993;98:5648–52.

    Article  CAS  Google Scholar 

  11. Runge E, Gross EKU. Density-functional theory for time-dependent systems. Phys Rev Lett. 1984;52:997–1000.

    Article  CAS  Google Scholar 

  12. 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.

    Article  Google Scholar 

  13. 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.

    Article  CAS  Google Scholar 

  14. 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.

    Article  CAS  Google Scholar 

  15. Yang P-C, Mahmood T. Western blot: Technique, theory, and trouble shooting. North Am J Med Sci. 2012;4:429.

    Article  Google Scholar 

  16. 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.

    Article  CAS  Google Scholar 

  17. Padula D, Pescitelli G. How and how much molecular conformation affects electronic circular dichroism: the case of 1,1-Diarylcarbinols. Molecules. 2018;23:128.

    Article  Google Scholar 

  18. 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.

    Article  CAS  Google Scholar 

  19. 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.

    Article  CAS  Google Scholar 

  20. 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.

    Article  CAS  Google Scholar 

  21. 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.

    Article  CAS  Google Scholar 

  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.

  23. 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.

    Article  CAS  Google Scholar 

  24. König G, Wright A. Two new naturally occurring pyrrole derivatives from the tropical marine sponge Agelas Oroides. Nat Prod Lett. 1994;5:141–6.

    Article  Google Scholar 

  25. 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.

    Article  CAS  Google Scholar 

  26. 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.

    Article  CAS  Google Scholar 

  27. 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.

    Article  CAS  Google Scholar 

  28. 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.

    Article  CAS  Google Scholar 

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Acknowledgements

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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Authors and Affiliations

  1. Agro-Processing and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram, 695019, Kerala, India

    Thankappan Drissya, M. S. Poornima, A. R. S. Jesmina, K. G. Raghu & B. S. Dileep Kumar

  2. Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, 201002, India

    Thankappan Drissya, D. K. Induja, M. S. Poornima, A. R. S. Jesmina, Mathew Saumini, Cherumuttathu H. Suresh, K. G. Raghu, B. S. Dileep Kumar & Ravi S. Lankalapalli

  3. Chemical Sciences and Technology Division, CSIR-National Institute for Interdisciplinary Science and Technology, Thiruvananthapuram, 695019, Kerala, India

    D. K. Induja, Bernard Prabha, Mathew Saumini, Cherumuttathu H. Suresh & Ravi S. Lankalapalli

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  1. Thankappan Drissya
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Correspondence to Ravi S. Lankalapalli.

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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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