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The thiodiketopiperazine derivatives shovelmycin A–B and ansamycin derivative divergolide X from the cold-seep-derived Streptomyces olivaceus HDN22-001

The Journal of Antibiotics volume 78, pages 275–280 (2025)Cite this article

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Abstract

Three new compounds including two thiodiketopiperazine derivatives shovelmycins A–B (1–2), and one ansamycin derivative divergolide X (3) were isolated and identified from the culture extract of Streptomyces olivaceus HDN22-001, a marine actinomycete obtained from the deep-sea cold seep sediment sample collected from the South China Sea. Their structures and absolute configurations were determined by spectroscopic analyses and ECD calculations. Compound 1 exhibited the strongest DPPH radical scavenging activity with an IC50 value of 10.83 μM, which was better than that of the positive control vitamin C. And compound 2 was modestly cytotoxic against NCl-H446 cell with the IC50 value of 26.6 μM.

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References

  1. Cong M, Pang X, Zhao K, Song Y, Liu Y, Wang J. Deep-sea natural products from extreme environments: cold seeps and hydrothermal vents. Mar Drugs. 2022;20:404.

    CAS  PubMed  PubMed Central  Google Scholar 

  2. Rampelotto PH. Extremophiles and extreme environments. Life. 2013;3:482–5.

    PubMed  PubMed Central  Google Scholar 

  3. Brown PD, Lawrence AL. The importance of asking “how and why?” in natural product structure elucidation. Nat Prod Rep. 2017;34:1193–202.

    CAS  PubMed  Google Scholar 

  4. Dubilier N, Bergin C, Lott C. Symbiotic diversity in marine animals: the art of harnessing chemosynthesis. Nat Rev Microbiol. 2008;6:725–40.

    CAS  PubMed  Google Scholar 

  5. Levin LA. Ecology of cold seep sediments: interactions of fauna with flow, chemistry and microbes. Oceanogr Mar Biol. 2005;43:1–46.

    Google Scholar 

  6. Chi LP, Li XM, Wan YP, Li X, Wang BG. Ophiobolin sesterterpenoids and farnesylated phthalide derivatives from the deep sea cold-seep-derived fungus Aspergillus insuetus SD-512. J Nat Prod. 2020;83:3652–60.

    CAS  PubMed  Google Scholar 

  7. Choi BK, Trinh PTH, Lee HS, Choi BW, Kang JS, Ngoc NTD, et al. New ophiobolin derivatives from the marine fungus Aspergillus flocculosus and their cytotoxicities against cancer cells. Mar Drugs. 2019;17:346.

    CAS  PubMed  PubMed Central  Google Scholar 

  8. Li X, Li L, Li XM, Li HL, Konuklugil B, Wang BG. Ustusaustin A: a new neuraminidase inhibitory meroterpene from the ascidian-derived endophytic fungus Aspergillus ustus TK-5. Nat Prod Res. 2021;35:4939–44.

    CAS  PubMed  Google Scholar 

  9. Che YH, Wang JF, Ding WP, Xiao ZH, Shi XF, Wu JM, et al. New diketopiperazine alkaloids from the Haima cold seep-derived fungus Toxicocladosporium sp. CYH-18. Phytochem Lett. 2024;60:96–100.

    CAS  Google Scholar 

  10. Hu XY, Wang CY, Li XM, Yang SQ, Li X, Wang BG, et al. Cytochalasin derivatives from the endozoic Curvularia verruculosa CS-129, a fungus isolated from the deep-sea squat lobster Shinkaia crosnieri living in the cold seep environment. J Nat Prod. 2021;84:3122–30.

    CAS  PubMed  Google Scholar 

  11. Ying Z, Li XM, Yang SQ, Li HL, Li X, Wang BG, et al. Pseudallenes A and B, new sulfur-containing ovalicin sesquiterpenoid derivatives with antimicrobial activity from the deep-sea cold seep sediment-derived fungus Pseudallescheria boydii CS-793. Beilstein J Org Chem. 2024;20:470–8.

    CAS  PubMed  PubMed Central  Google Scholar 

  12. Dong Y, Wang JingE, Bao R, Li Y. H. New Olimycins from a Cold‐Seep‐Derived Streptomyces olivaceus. Chem Biodivers. 2023;20:e202300689.

    CAS  PubMed  Google Scholar 

  13. Jin E, Li H, Liu Z, Xiao F. Antibiotic Dixiamycins from a Cold-Seep-Derived Streptomyces olivaceus. J Nat Prod. 2021;84:2606–11.

    CAS  PubMed  Google Scholar 

  14. Chen CL, Hu SJ, Zhu LL, Yao LM, Wang XX, Zhang AN, et al. Isolation and identification of chemical constituents of Rubi Fructus, screening novel cannabinoid CB2 receptor agonist and evaluation of its anti-osteoporosis effect. Chin Tradit Herbal Drugs. 2024;55:386–401.

    Google Scholar 

  15. Furukawa T, Akutagawa T, Funatani H, Uchida T, Hotta Y, Niwa M, et al. Cyclic dipeptides exhibit potency for scavenging radicals. Bioorg Med Chem. 2012;20:2002–9.

    CAS  PubMed  Google Scholar 

  16. Zhao G, Li S, Guo Z, Sun M, Lu C. Overexpression of div 8 increases the production and diversity of divergolides in Streptomyces sp. W112. RSC adv. 2015;5:98209–14.

    CAS  Google Scholar 

  17. Tu L, Shen S, Yan Z, Li X, Liu K, Xu J, et al. Discovery of olimycin E from Streptomyces sp. 11695. Nat Prod Res. 2024;4:1–6.

    Google Scholar 

  18. Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, et al. Gaussian 09, Revision A.1, Gaussian Inc. Wallingford CT;USA;2009.

  19. Bruhn T, Schaumlöffel A, Hemberger Y, Bringmann G SpecDis, Version 1.53. University of Wuerzburg;Germany;2011.

  20. Sharma OP, Tej KB. DPPH antioxidant assay revisited. Food Chem. 2009;113:1202–5.

    CAS  Google Scholar 

  21. Andrews JM. Determination of minimum inhibitory concentrations. J Antimicrob Chemother. 2001;48:5–16.

    CAS  PubMed  Google Scholar 

  22. Mosmann T. Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods. 1983;65:55–63.

    CAS  PubMed  Google Scholar 

  23. Skehan P, Storeng R, Scudiero D, Monks A, McMahon J, Vistica D, et al. New colorimetric cytotoxicity assay for anticancer-drug screening. J Natl Cancer Inst. 1990;82:1107–12.

    CAS  PubMed  Google Scholar 

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Acknowledgements

This work was supported by the Fundamental Research Funds for the Central Universities (202362008, 202172002), the Shandong Provincial Natural Science Foundation (ZR2021MH257), the National Key Research and Development Program of China (2022YFC2804400).

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Authors and Affiliations

  1. School of Medicine and Pharmacy, Key Laboratory of Marine Drugs Ministry of Education, Frontiers Science Center for Deep Ocean Multispheres and Earth System, Ocean University of China, Qingdao, People’s Republic of China

    Chen Li, Jiangli Cheng, Ruojin Liu, Xiaofei Huang, Luning Zhou, Guojian Zhang, Tianjiao Zhu, Dehai Li & Qian Che

  2. Laboratory for Marine Drugs and Bioproducts, Laoshan Laboratory, Qingdao, People’s Republic of China

    Guojian Zhang, Tianjiao Zhu, Dehai Li & Qian Che

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  1. Chen Li
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  2. Jiangli Cheng
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Correspondence to Qian Che.

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Li, C., Cheng, J., Liu, R. et al. The thiodiketopiperazine derivatives shovelmycin A–B and ansamycin derivative divergolide X from the cold-seep-derived Streptomyces olivaceus HDN22-001. J Antibiot 78, 275–280 (2025). https://doi.org/10.1038/s41429-025-00812-z

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