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Iseolides A–C, antifungal macrolides from a coral-derived actinomycete of the genus Streptomyces

Abstract

Iseolides A–C (13), three new glycosylated macrolides, were identified from the culture extract of Streptomyces sp. DC4-5 isolated from a stony coral Dendrophyllia. Extensive analysis of one- and two-dimensional NMR data, coupled with MS/MS analytical data, revealed that iseolides are new congeners of 36-membered macrolides, PM100117 and PM100118, previously reported from a marine-derived Streptomyces. Iseolides showed potent antifungal activity against a plant pathogen Glomerella cingulata and human pathogens Candida albicans and Trichophyton rubrum with MIC in the range of 0.19–6.25 μg/mL.

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References

  1. Cannon PF, Damm U, Johnston PR, Weir BS. Colletotrichum—current status and future directions. Stud Mycol. 2012;73:181–213.

    Article  CAS  Google Scholar 

  2. Freeman S, Katan T, Shabi E. Characterization of Colletotrichum species responsible for anthracnose diseases of various fruits. Plant Dis. 1998;8:596–605.

    Article  Google Scholar 

  3. Than PP, Prihastuti H, Phoulivong S, Taylor PWJ, Hyde KD. Chili anthracnose disease caused by Colletotrichum species. J Zhejiang Univ Sci B. 2008;10:764–78.

    Article  Google Scholar 

  4. Ridzuan R, Rafii MY, Ismail SI, Mohammad Yusoff M, Miah G, Usman M. Breeding for anthracnose disease resistance in chili: progress and prospects. Int J Mol Sci. 2018;19:E3122.

    Article  Google Scholar 

  5. Oo MM, Lim GT, Jang HA, Oh SK. Characterization and pathogenicity of new record of anthracnose on various chili varieties caused by Colletotrichum scovillei in Korea. Mycobiology. 2017;45:184–91.

    Article  Google Scholar 

  6. Higuera JJ, et al. The strawberry FaWRKY1 transcription factor negatively regulates resistance to Colletotrichum acutatum in fruit upon infection. Front Plant Sci. 2019;10:480.

    Article  Google Scholar 

  7. Elias LM, et al. The potential of compounds isolated from Xylaria spp. as antifungal agents against anthracnose. Braz J Microbiol. 2018;49:840–7.

    Article  CAS  Google Scholar 

  8. Materatski P, et al. Effect of long-term fungicide applications on virulence and diversity of Colletotrichum spp. associated to olive anthracnose. Plants. 2019:E311:1–20.

    Google Scholar 

  9. Slusarenko AJ, Patel A, Portz D. Control of plant diseases by natural products: allicin from garlic as a case study. Eur J Plant Pathol. 2008;121:313–22.

    Article  Google Scholar 

  10. Schinke C, Martins T, Queiroz SCN, Melo IS, Reyes FGR. Antibacterial compounds from marine bacteria, 2010−2015. J Nat Prod. 2017;80:1215–28.

    Article  CAS  Google Scholar 

  11. Valliappan K, Sun W, Li ZY. Marine actinobacteria associated with marine organisms and their potentials in producing pharmaceutical natural products. Appl Microbiol Biotechnol. 2014;98:7365–77.

    Article  CAS  Google Scholar 

  12. Subramani R, Sipkema D. Marine rare actinomycetes: a promising source of structurally diverse and unique novel natural products. Mar Drugs. 2019;17:249.

    Article  CAS  Google Scholar 

  13. Mehbub MF, Tanner JE, Barnett SJ, Franco CM, Zhang W. The role of sponge-bacteria interactions: the sponge Aplysilla rosea challenged by its associated bacterium Streptomyces ACT-52A in a controlled aquarium system. Appl Microbiol Biotechnol. 2016;100:10609–26.

    Article  CAS  Google Scholar 

  14. Frias-Lopez J, Zerkle AL, Bonheyo GT, Fouke BW. Partitioning of bacterial communities between seawater and healthy, black band diseased, and dead coral surface. Appl Environ Microbiol. 2002;68:2214–28.

    Article  CAS  Google Scholar 

  15. Castro AP, et al. Bacterial community associated with healthy and diseased reef coral Mussismilia hispida from eastern Brazil. Microb Ecol. 2010;59:658–67.

    Article  Google Scholar 

  16. Sharma AR, Zhou T, Harunari E, Oku N, Trianto A, Igarashi Y. Labrenzbactin from a coral-associated bacterium Labrenzia sp. J Antibiot. 2019;72:634–9.

    Article  Google Scholar 

  17. Sharma AR, Harunari E, Zhou T, Trianto A, Igarashi Y. Isolation and biosynthesis of an unsaturated fatty acid with unusual methylation pattern from a coral-associated bacterium Microbulbifer sp. Beilstein J Org Chem. 2019;15:2327–32.

    Article  CAS  Google Scholar 

  18. Pérez M, et al. PM100117 and PM100118, new antitumor macrolides produced by a marine Streptomyces caniferus GUA-06-05-006A. J Antibiot. 2016;69:388–94.

    Article  Google Scholar 

  19. Alferova VA, et al. Astolides A and B, antifungal and cytotoxic naphthoquinone-derived polyol macrolactones from Streptomyces hygroscopicus. Tetrahedron. 2018;74:7442–9.

    Article  CAS  Google Scholar 

  20. Pérez-Victoria I, et al. Structure elucidation and biosynthetic gene cluster analysis of caniferolides A-D, new bioactive glycosylated 36-membered polyol macrolides from the marine-derived Streptomyces caniferus CA-271066. Org Biomol Chem. 2019;17:2954–71.

    Article  Google Scholar 

  21. Takahashi I, Nishiie Y, Uosaki Y, Ochiai K. New substance GT35 and its production. Jpn Kokai Tokkyo Koho. 1995:JPH09100290A.

  22. Takeuchi T, et al. ATP depletion assay led to the isolation of new 36-membered polyol macrolides deplelides A and B from Streptomyces sp. MM581-NF15. Org Lett. 2017;19:4207–10.

    Article  CAS  Google Scholar 

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Acknowledgements

Authors are in debt to Prof. Yasufumi Hikichi and Dr Ayami Kanda at Kochi University for providing R. solanacearum SUPP1541. P388 cells were obtained from JCRB Cell Bank under an accession code JCRB0017 (Lot. 06252002).

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Correspondence to Yasuhiro Igarashi.

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Dedicated to Professor William Fenical in recognition of his pioneering and outstanding contributions to marine natural products.

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Zhang, Z., Zhou, T., Harunari, E. et al. Iseolides A–C, antifungal macrolides from a coral-derived actinomycete of the genus Streptomyces. J Antibiot 73, 534–541 (2020). https://doi.org/10.1038/s41429-020-0304-7

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