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Emericellopsic acid, a helvolic acid derivative with a 6/5/7/5 tetracyclic skeleton from sponge-derived Emericellopsis maritima

The Journal of Antibiotics volume 78, pages 580–585 (2025)Cite this article

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Abstract

Emericellopsic acid (1), the first B/C ring-rearranged fusidane-type antibiotic possessing a 6/5/7/5-fused ring framework, together with seven known helvolic acid derivatives, was isolated from the sponge-associated fungus Emericellopsis maritima IMB18-123 cultivated with autoclaved Pseudomonas aeruginosa. The structure of 1 was determined by extensive spectroscopic data analysis combined with ECD calculation. Compound 1 exhibited moderate antimicrobial activities against Staphylococcus aureus and S. epidermidis with the minimum inhibition concentration of 4−8 μg ml−1.

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References

  1. Godtfredsen WO, Jahnsen S, Lorck H, Roholt K, Tybring L. Fusidic acid: a new antibiotic. Nature. 1962;193:987.

    Article  PubMed  CAS  Google Scholar 

  2. Chain E, Florey HW, Jennings MA, Williams TI. Helvolic acid, an antibiotic produced by Aspergillus fumigatus, mut. helvola Yuill. Br J Exp Pathol. 1943;24:108–19.

    PubMed Central  CAS  Google Scholar 

  3. Burton HS, Abraham EP. Isolation of antibiotics from a species of Cephalosporium. cephalosporins P1, P2, P3, P4, and P5. Biochem J. 1951;50:168–74.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  4. von Daehne W, Godtfredsen WO, Rasmussen PR. Structure-activity relationships in fusidic acid-type antibiotics. Adv Appl Microbiol. 1979;25:95–146.

    Article  Google Scholar 

  5. Fernandes P. Fusidic acid: a bacterial elongation factor inhibitor for the oral treatment of acute and chronic staphylococcal infections. Cold Spring Harb Perspect Med. 2016;6:a025437.

    Article  PubMed  PubMed Central  Google Scholar 

  6. Williamson DA, Carter GP, Howden BP. Current and emerging topical antibacterials and antiseptics: agents, action, and resistance patterns. Clin Microbiol Rev. 2017;30:827–60.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  7. Marian E, Tita B, Duteanu N, Vicas L, Ciocan S, Jurca T, et al. Antimicrobial activity of fusidic acid inclusion complexes. Int J Infect Dis. 2020;101:65–73.

    Article  PubMed  CAS  Google Scholar 

  8. Zhao M, Gödecke T, Gunn J, Duan JA, Che CT. Protostane and fusidane triterpenes: a mini-review. Molecules. 2013;18:4054–80.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  9. Cao Z-Q, Lv J-M, Liu Q, Qin S-Y, Chen G-D, Dai P, et al. Biosynthetic study of cephalosporin P1 reveals a multifunctional P450 enzyme and a site-selective acetyltransferase. ACS Chem Biol. 2020;15:44–51.

    Article  PubMed  CAS  Google Scholar 

  10. The compound name given in the reference with 29-nordammarane as the parent structure should be corrected by 29-norprotostane, Kong FD, Huang XL, Ma QY, Xie QY, Wang P, Chen PW, et al. Helvolic acid derivatives with antibacterial activities against Streptococcus agalactiae from the marine-derived fungus Aspergillus fumigatus HNMF0047. J Nat Prod. 2018;81:1869–76.

    Article  Google Scholar 

  11. Afiyatullov S, Zhuravleva OI, Antonov AS, Kalinovsky AI, Pivkin MV, Menchinskaya ES, et al. New metabolites from the marine-derived fungus Aspergillus fumigatus. Nat Prod Commun. 2012;7:497–500.

    PubMed  CAS  Google Scholar 

  12. Tian C, Gao H, Peng XP, Li G, Lou HX. Fusidic acid derivatives from the endophytic fungus Acremonium pilosum F47. J Asian Nat Prod Res. 2021;23:1148–55.

    Article  PubMed  CAS  Google Scholar 

  13. Zhang ZB, Du SY, Ji B, Ji CJ, Xiao YW, Yan RM, et al. New helvolic acid derivatives with antibacterial activities from Sarocladium oryzae DX-THL3, an endophytic fFungus from Dongxiang Wild rice (Oryza rufipogon Griff.). Molecules. 2021;26:1828.

    Article  PubMed  PubMed Central  CAS  Google Scholar 

  14. Zhang B, Zhang T, Xu J, Lu J, Qiu P, Wang T, et al. Marine sponge-associated fungi as potential novel bioactive natural product sources for drug discovery: a review. Mini Rev Med Chem. 2020;20:1966–2010.

    Article  PubMed  CAS  Google Scholar 

  15. Hao X, Li S, Ni J, Wang G, Li F, Li Q, et al. Acremopeptaibols A–F, 16-residue peptaibols from the sponge-derived Acremonium sp. IMB18-086 cultivated with heat-killed Pseudomonas aeruginosa. J Nat Prod. 2021;84:2990–3000.

    Article  PubMed  CAS  Google Scholar 

  16. Li J, Chen M, Hao X, Li S, Li F, Yu L, et al. Structural revision and absolute configuration of burnettramic acid A. Org Lett. 2020;22:98–101.

    Article  PubMed  CAS  Google Scholar 

  17. Li S, Li Y, Yu T, Wei X, Zhang Y, Chen B, et al. Discovery of potent antiosteoporotic cyclic depsipeptides with an unusual nitrile hydroxy acid from Microascus croci. Bioorg Chem. 2025;155:108133.

    Article  PubMed  CAS  Google Scholar 

  18. Zaman KAU, Hu Z, Wu X, Hou S, Saito J, Kondratyuk TP, et al. NF-κB inhibitory and antibacterial helvolic and fumagillin derivatives from Aspergillus terreus. J Nat Prod. 2020;83:730–7.

    Article  PubMed  Google Scholar 

  19. Godtfredsen WO, Rastrup-Andersen N, Vangedal S, Ollis WD. Metabolites of fusidium coccineum. Tetrahedron. 1979;35:2419–31.

    Article  CAS  Google Scholar 

  20. Ratnaweera PB, Williams DE, de Silva ED, Wijesundera RL, Dalisay DS, Andersen RJ. Helvolic acid, an antibacterial nortriterpenoid from a fungal endophyte, Xylaria sp. of orchid Anoectochilus setaceus endemic to Sri Lanka. Mycology. 2014;5:23–8.

    Article  PubMed  Google Scholar 

  21. Song X, Lv J, Cao Z, Huang H, Chen G, Awakawa T, et al. Extensive expansion of the chemical diversity of fusidane-type antibiotics using a stochastic combinational strategy. Acta Pharm Sin B. 2021;11:1676–85.

    Article  PubMed  CAS  Google Scholar 

  22. Lv J-M, Hu D, Gao H, Kushiro T, Awakawa T, Chen G-D, et al. Biosynthesis of helvolic acid and identification of an unusual C-4-demethylation process distinct from sterol biosynthesis. Nat Commun. 2017;8:1644.

    Article  PubMed  PubMed Central  Google Scholar 

  23. Mitsuguchi H, Seshime Y, Fujii I, Shibuya M, Ebizuka Y, Kushiro T. Biosynthesis of steroidal antibiotic fusidanes: functional analysis of oxidosqualene cyclase and subsequent tailoring enzymes from Aspergillus fumigatus. J Am Chem Soc. 2009;131:6402–11.

    Article  PubMed  CAS  Google Scholar 

  24. Fujimoto H, Negishi E, Yamaguchi K, Nishi N, Yamazaki M. Isolation of new tremorgenic metabolites from an ascomycete, Corynascus setosus. Chem Pharm Bull. 1996;44:1843–8.

    Article  CAS  Google Scholar 

  25. Lee SY, Kinoshita H, Ihara F, Igarashi Y, Nihira T. Identification of novel derivative of helvolic acid from Metarhizium anisopliae grown in medium with insect component. J Biosci Bioeng. 2008;105:476–80.

    Article  PubMed  CAS  Google Scholar 

  26. Molecular operating environment (moe), 2019.01. Chemical Computing Group Inc. 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada, H3A 2R7, 2019.

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

  28. Bruhn T, Schaumlöffel A, Hemberger Y, Bringmann G. SpecDis: Quantifying the Comparison of Calculated and Experimental Electronic Circular Dichroism Spectra. Chirality. 2013;25:243–9.

    Article  PubMed  CAS  Google Scholar 

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Acknowledgements

This work was financially supported by the National Natural Science Foundation of China (Grant no. 82273830), CAMS Innovation Fund for Medical Sciences (CIFMS, 2021-I2M-1-055 and 2024-I2M-TS-016), and National Key R&D Program of China (Grant no. 2024YFC2309604).

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  1. Institute of Medicinal Biotechnology, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing, P. R. China

    Shasha Li, Xiaomeng Hao, Yan Li & Maoluo Gan

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  1. Shasha Li
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  2. Xiaomeng Hao
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Correspondence to Maoluo Gan.

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Li, S., Hao, X., Li, Y. et al. Emericellopsic acid, a helvolic acid derivative with a 6/5/7/5 tetracyclic skeleton from sponge-derived Emericellopsis maritima. J Antibiot 78, 580–585 (2025). https://doi.org/10.1038/s41429-025-00852-5

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