Chemistry of Natural Compounds

, Volume 54, Issue 2, pp 253–256 | Cite as

Four Verrucosidin Derivatives Isolated from the Hydrothermal Vent Sulfur-Derived Fungus Penicillium sp. Y-50-10

  • Chengqian Pan
  • Yutong Shi
  • Bibi Nazia Auckloo
  • Chen-Tung Arthur Chen
  • Xuegang Chen
  • Xiaodan Wu
  • Bin Wu
Article
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Four verrucosidin derivatives, penicyrone (1), norpenicyrone (2), methyl norpenicyrone (3), and methyl penicyrone (4) were isolated from the hydrothermal vent sulfur-derived fungus Penicillium sp. Y-50-10. Compounds 1–4 were obtained as a mixture of two epimers. Compounds 2–4 have been proved to be new secondary metabolites. The chemical structures were determined by comparing with literature data and HR-MS and 2D NMR spectroscopic analysis. The migration of the double bond from C8=C9 to C7=C8 in compounds 1–4 allowed the assignment of a rearranged verrucosidin skeleton. Compounds 1–4 showed activity against B. subtilis, with MIC values of 32 μg/mL.

Keywords

marine fungus Penicillium sp. penicyrone 

Notes

Acknowledgment

This work was supported by NSFC (Nos. 81273386 and 81573306).

References

  1. 1.
    J. W. Blunt, B. R. Copp, R. A. Keyzers, M. H. Munro, and M. R. Prinsep, Nat. Prod. Rep., 32, 116 (2015).CrossRefPubMedGoogle Scholar
  2. 2.
    M. Saleem, M. S. Ali, S. Hussain, A. Jabbar, M. Ashraf, and Y. S. Lee, Nat. Prod. Rep., 24, 1142 (2007).CrossRefPubMedGoogle Scholar
  3. 3.
    D. Skropeta and L. Wei, Nat. Prod. Rep., 31, 999 (2014).CrossRefPubMedGoogle Scholar
  4. 4.
    R. K. Pettit, Mar. Biotech., 13, 1 (2011).CrossRefGoogle Scholar
  5. 5.
    F. Song, H. Dai, Y. Tong, B. Ren, C. Chen, N. Sun, X. Liu, J. Bian, M. Liu, H. Gao, H. Liu, X. Chen, and L. Zhang, J. Nat. Prod., 73, 806 (2010).CrossRefPubMedGoogle Scholar
  6. 6.
    L. Zhang, R. An, J. Wang, N. Sun, S. Zhang, J. Hu, and J. Kuai, Curr. Opin. Microbiol., 8, 276 (2005).CrossRefPubMedGoogle Scholar
  7. 7.
    M. Ganguli, L.T. Burka, and T. M. Harris, J. Org. Chem., 49, 3762 (1984).CrossRefGoogle Scholar
  8. 8.
    K. Whang, R. J. Cooke, G. Okay, and J. K. Cha, J. Am. Chem. Soc., 112, 8989 (1990).CrossRefGoogle Scholar
  9. 9.
    B. J. Wilson, C. S. Byerly, and L. T. Burka, J. Am. Vet. Med. Assoc., 179, 480 (1981).PubMedGoogle Scholar
  10. 10.
    R. P. Hodge, C. M. Harris, and T. M. Harris, J. Nat. Prod., 51, 66 (1988).CrossRefPubMedGoogle Scholar
  11. 11.
    S.-J. Choo, H.-R. Park, I.-J. Ryoo, J.-P. Kim, B.-S. Yun, Ch.-J. Kim, K. Shin-ya, and I.-D. Yoo, J. Antibiot., 58, 210 (2005).CrossRefPubMedGoogle Scholar
  12. 12.
    C. Pan, Y. Shi, B. N. Auckloo, X. Chen, C. T. A. Chen, X. Tao, and B. Wu, Mar. Drugs, 14, 156 (2016).CrossRefPubMedCentralGoogle Scholar
  13. 13.
    Y. Y. Bu, H. Yamazaki, O. Takahashi, R. Kirikoshi, K. Ukai, and M. Namikoshi, J. Antibiot., 69, 57 (2016).CrossRefPubMedGoogle Scholar
  14. 14.
    G. Appendino, S. Gibbons, A. Giana, A. Pagani, G. Grassi, M. Stavri, E. Smith, and M. M. Rahman, J. Nat. Prod., 71, 1427 (2008).CrossRefPubMedGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Chengqian Pan
    • 1
  • Yutong Shi
    • 1
  • Bibi Nazia Auckloo
    • 1
  • Chen-Tung Arthur Chen
    • 2
  • Xuegang Chen
    • 1
  • Xiaodan Wu
    • 3
  • Bin Wu
    • 1
  1. 1.Ocean CollegeZhejiang UniversityHangzhouP. R. China
  2. 2.Department of OceanographyNational Sun Yat-sen UniversityKaohsiungP. R. China
  3. 3.Center of Analysis and MeasurementZhejiang UniversityHangzhouP. R. China

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