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Citrinadin C, a new cytotoxic pentacyclic alkaloid from marine-derived fungus Penicillium citrinum

Abstract

A new cytotoxic pentacyclic alkaloid, citrinadin C (1), together with four known compounds (25), were isolated from deep-sea-derived fungus Penicillium citrinum. The structure of new compound 1 was elucidated by extensive 1D and 2D NMR and Mass spectroscopic data, and its absolute configuration was determined by CD spectrum. All the compounds were evaluated for their cytotoxic and antibacterial activities. Compound 1 showed cytotoxic activities against human liver cancer cell line MHCC97H, with IC50 value of 16.7 μM. Compound 4 displayed significant antibacterial activity against phytopathogen Xanthomonas campestris, with MIC value of 25 μM.

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References

  1. Schueffler A, Anke T. Fungal natural products in research and development. Nat Prod Rep. 2014;31:1425–48.

    Article  CAS  Google Scholar 

  2. Moghaddam JA, Jautzus T, Alanjary M, Beemelmanns C. Recent highlights of biosynthetic studies on marine natural products. Org Biomol Chem. 2021;19:123–40.

    Article  Google Scholar 

  3. Tsuda M, Kasai Y, Komatsu K, Sone T, Tanaka M, Mikami Y, Kobayashi J. Citrinadin A, a novel pentacyclic alkaloid from marine-derived fungus Penicillium citrinum. Org Lett. 2004;6:3087–9.

    Article  CAS  Google Scholar 

  4. Mugishima T, Tsuda M, Kasai Y, Ishiyama H, Fukushi E, Kawabata J, Watanabe M, Akao K, Kobayashi J. Absolute stereochemistry of Citrinadins A and B from marine-derived fungus. J Org Chem. 2005;70:9430–5.

    Article  CAS  Google Scholar 

  5. Bian Z, Marvin CC, Martin SF. Enantioselective total synthesis of (−)-Citrinadin A and revision of its stereochemical structure. J Am Chem Soc. 2013;135:10886–9.

    Article  CAS  Google Scholar 

  6. Guerrero CA, Sorensen EJ. Concise. Stereocontrolled synthesis of the Citrinadin B core architecture. Org Lett. 2011;13:5164–7.

    Article  CAS  Google Scholar 

  7. Kong K, Enquist JA, McCallum ME, Smith GM, Matsumaru T, Menhaji-Klotz E, Wood JL. An enantioselective total synthesis and stereochemical revision of (+)-Citrinadin B. J Am Chem Soc. 2013;135:10890–3.

    Article  CAS  Google Scholar 

  8. Liu Z, Zhao F, Zhao BY, Yang J, Ferrara J, Sankaran B, Venkataram PBV, Kundu BB, Phillips GN, Gao Y, Hu L, Zhu T, Gao X. Structural basis of the stereoselective formation of the spirooxindole ring in the biosynthesis of citrinadins. Nat Commun. 2021;12:4158.

    Article  CAS  Google Scholar 

  9. Chen MB, Liu CT, Tang Y. Discovery and biocatalytic application of a PLP-dependent amino acid γ-substitution enzyme that catalyzes C-C bond formation. J Am Chem Soc. 2020;42:10506–15.

    Article  Google Scholar 

  10. Wu YH, Zhang ZH, Huang JJ, Zhong Y, Li XX, Deng YY, Zhang LH, He F. Sumalactones A-D, four new curvularin-type macrolides from a marine deep sea fungus Penicillium Sumatrense. RSC Adv. 2017;7:40015–9.

    Article  CAS  Google Scholar 

  11. Zhang ZH, Min XT, Huang JJ, Zhong Y, Wu YH, Li XX, Deng YY, Jiang ZD, Shao ZZ, Zhang LH, He F. Cytoglobosins H and I, new antiproliferative cytochalasans from deep-sea-derived fungus Chaetomium globosum. Mar Drugs. 2016;14:233.

    Article  Google Scholar 

  12. He F, Bao J, Zhang XY, Tu ZT, Shi YM, Qi SH. Asperterrestide A, a cytotoxic cyclic tetrapeptide from the marine-derived fungus Aspergillus terreus SCSGAF0162. J Nat Prod. 2013;76:1182–6.

    Article  CAS  Google Scholar 

  13. He F, Sun YL, Liu KS, Zhang XY, Qian PY, Wang YF, Qi SH. Indole alkaloids from marine-derived fungi Aspergillus sp. SCSIO 00305. J Antibiot. 2012;65:109–11.

    Article  CAS  Google Scholar 

  14. Shen J, Zou J, Xie D, Ge H, Cao X, Dai J. Butyrolactone and cycloheptanetrione from mangrove-associated fungus Aspergillus terreus. Chem Pharm Bull. 2012;60:1437–41.

    Article  CAS  Google Scholar 

  15. Clark BR, Capon RJ, Lacey E, Tennantb S, Gillb JH. Citrinin revisited: from monomers to dimers and beyond. Org Biomol Chem. 2006;4:1520–8.

    Article  CAS  Google Scholar 

  16. Daigo W, Tomoo H, Takeshi I, Kaoru O, Galba M, Takashi Y, Kazutaka F, Ken-ichi K. New citrinin derivatives isolated from Penicillium citrinum. J Nat Med. 2006;60:279–84.

    Article  Google Scholar 

  17. Hu Y, Zhang J, Liu D, Guo J, Liu T, Xin Z. Pencitrin and pencitrinol, two new citrinin derivatives from an endophytic fungus Penicillium citrinum salicorn 46. Phytochem Lett. 2017;22:229–34.

    Article  CAS  Google Scholar 

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Acknowledgements

The authors are grateful to the National Natural Science Foundation of China (41206130) for financial support.

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Correspondence to Fei He.

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Jiang, J., Jiang, H., Shen, D. et al. Citrinadin C, a new cytotoxic pentacyclic alkaloid from marine-derived fungus Penicillium citrinum. J Antibiot 75, 301–303 (2022). https://doi.org/10.1038/s41429-022-00516-8

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  • DOI: https://doi.org/10.1038/s41429-022-00516-8

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