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Sinulaflexiolide P, A Cembrane-Type Diterpenoid from Bornean Soft Coral Sinularia flexibilis

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Chemistry of Natural Compounds Aims and scope

A new cembrane-type diterpenoid, sinulaflexiolide P (1), along with three known derivatives: sinulaflexiolide H (2), 11-epi-sinulariolide acetate (3), and (1S*,3S*,4S*,7E,11E)-3,4-epoxy-13-oxo-3,7,11,15-cembratriene (4), was isolated from a population of Bornean soft coral Sinularia flexibilis. The structures of these metabolites were elucidated based on spectroscopic data including NMR and HR-ESI-MS. In addition, these compounds were tested against six strains of marine fungi.

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References

  1. J. W. Blunt, B. R. Copp, R. A. Keyzers, M. H. G. Munro, and M. R. Prinsep, Nat. Prod. Rep., 34, 235 (2017).

    Article  CAS  PubMed  Google Scholar 

  2. J. A. V. Lopez, J. G. Petitbois, C. S. Vairappan, T. Umezawa, F. Matsuda, and T. Okino, Org. Lett., 19, 4231 (2017).

    Article  CAS  PubMed  Google Scholar 

  3. C. Y. Duh, S. C. Chien, P. Y. Song, S. K. Wang, A. A. El-Gamal, and C. F. Dai, J. Nat. Prod., 65, 1853 (2002).

    Article  CAS  PubMed  Google Scholar 

  4. C. S. Phan and C. S. Vairappan, Nat. Prod. Res., 31, 742 (2017).

    Article  CAS  PubMed  Google Scholar 

  5. M. Zhao, J. Yin, W. Jiang, M. Ma, X. Lei, Z. Xiang, J. Dong, K. Huang, and P. Yan, Mar. Drugs, 11, 1162 (2013).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  6. L. F. Liang, L. X. Gao, J. Li, O. Taglialatela-Scafati, and Y. W. Guo, Bioorg. Med. Chem., 21, 5076 (2013).

    Article  CAS  PubMed  Google Scholar 

  7. T. Kamada, C. S. Phan, H. S. Tin, C. S. Vairappan, and T. S. T. Muhammad, Nat. Prod. Commun., 11, 1077 (2016).

    PubMed  Google Scholar 

  8. P. Yan, Z. Deng, L. van Ofwegen, P. Proksch, and W. Lin, Chem. Pharm. Bull., 58, 1591 (2010).

    Article  CAS  PubMed  Google Scholar 

  9. P. Sun, Q. Yu, J. Li, R. Riccio, G. Lauro, G. Bifulco, T. Kurtan, A. Mandi, H. Tang, T. J. Li, C. L. Zhuang, W. H. Gerwick, and W. Zhang, J. Nat. Prod., 79, 2552 (2016).

    Article  CAS  PubMed  Google Scholar 

  10. B. F. Bowden, B. J. Cusack, and A. Dangel, Mar. Drugs, 1, 18 (2003).

    Article  CAS  PubMed Central  Google Scholar 

  11. N. E. Awad, M. A. Selim, H. M. Metawe, and A. A. Matloub, Phytother. Res., 22, 1610 (2008).

    Article  CAS  PubMed  Google Scholar 

  12. R. W. Dunlop and R. J. Wells, Aust. J. Chem., 32, 1345 (1979).

    Article  CAS  Google Scholar 

  13. L. Li, L. Sheng, C. Y. Wang, Y. B. Zhou, H. Huang, X. B. Li, J. Li, E. Mollo, M. Gavagnin, and Y. W. Guo, J. Nat. Prod., 74, 2089 (2011).

    Article  CAS  PubMed  Google Scholar 

  14. Y. N. Lee, C. J. Tai, T. L. Hwang, and J. H. Sheu, Mar. Drugs, 11, 2741 (2013).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  15. C. H. Cheng, Y. S. Lin, Z. H. Wen, and J. H. Su, Molecules, 17, 10072 (2012).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. Y. Li, M. Carbone, R. M. Vitale, P. Amodeo, F. Castelluccio, G. Sicilia, E. Mollo, M. Nappo, G. Cimino, Y. W. Guo, and M. Gavagnin, J. Nat. Prod., 73, 133 (2010).

    Article  CAS  PubMed  Google Scholar 

  17. S. V. Govindam, Y. Yoshioka, A. Kanamoto, T. Fujiwara, T. Okamoto, and M. Ojika, Bioorg. Med. Chem., 20, 687 (2012).

    Article  CAS  PubMed  Google Scholar 

  18. J. H. Sheu, J. H. Su, P. J. Sung, G. H. Wang, and C. F. Dai, J. Nat. Prod., 67, 2048 (2004).

    Article  CAS  PubMed  Google Scholar 

  19. W. T. Chen, Y. Li, and Y. W. Guo, Acta Pharm. Sin. B., 2, 227 (2012).

    Article  CAS  Google Scholar 

  20. T. Kamada, C. S. Phan, T. Hamada, K. Hatai, and C. S. Vairappan, Nat. Prod. Commun., 13, 17 (2018).

    Google Scholar 

  21. C. S. Phan, S. Y. Ng, T. Kamada, and C. S. Vairappan, Nat. Prod. Commun., 11, 899 (2016).

    PubMed  Google Scholar 

  22. A. D. Wright, J. L. Nielson, D. M. Tapiolas, C. H. Liptrot, and C. A. Motti, Mar. Drugs, 10, 1619 (2012).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. C. S. Vairappan, I. I. Zanil, T. Kamada, and M. Palaniappan, J. Trop. Biol. Conserv., 9, 200 (2012).

    Google Scholar 

  24. T. Wen, Y. Ding, Z. Deng, L. van Ofwegen, P. Proksch, and W. Lin, J. Nat. Prod., 71, 1133 (2008).

    Article  CAS  PubMed  Google Scholar 

  25. W. T. Chen, J. Li, J. R. Wang, X. W. Li, and Y. W. Guo, RSC Adv., 5, 23973 (2015).

    Article  CAS  Google Scholar 

  26. T. C. Tsai, H. Y. Chen, J. H. Sheu, M. Y. Chiang, Z. H. Wen, C. F. Dai, and J. H. Su, J. Agric. Food Chem., 63, 7211 (2015).

    Article  CAS  PubMed  Google Scholar 

  27. L. C. Hu, W. H. Yen, J. H. Su, M. Y. N. Chiang, Z. H. Wen, W. F. Chen, T. J. Lu, Y. W. Chang, Y. H. Chen, W. H. Wang, Y. C. Wu, and P. J. Sung, Mar. Drugs, 11, 2154 (2013).

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  28. W. T. Chen, H. L. Liu, and Y. W. Guo, Steroids, 92, 56 (2014).

    Article  CAS  PubMed  Google Scholar 

  29. D. A. Putri, O. K. Radjasa, and D. Pringgenies, Procedia Environ. Sci., 23, 351 (2015).

    Article  CAS  Google Scholar 

  30. P. W. Hsieh, F. R. Chang, A. T. McPhail, K. Lee, and Y. C. Wu, Nat. Prod. Res., 17, 409 (2013).

    Article  CAS  Google Scholar 

  31. B. N. Ravi and D. J. Faulkner, J. Org. Chem., 43, 2127 (1978).

    Article  CAS  Google Scholar 

  32. C. Munchan, K. Hatai, S. Takagi, and A. Yamashita, Aquacult. Sci., 57, 399 (2009).

    CAS  Google Scholar 

Download references

Acknowledgment

This work was supported by the Sabah Biodiversity Centre (GL0070), the Fujiwara Natural History Foundation, Universiti Malaysia Sabah (GUG0089-SG-2/2016) and the Ministry of Higher Education, Malaysia (FRG0464-2017). The authors would like to thank Prof. Dr. Tatsufumi Okino and Ms. Liang Wei (Hokkaido University) for SciFinder Search as well as Prof. Dr. Hatai (Universiti Malaysia Sabah) for guidance and providing the fungal strains.

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Authors and Affiliations

  1. Institute for Tropical Biology and Conservation, Universiti Malaysia Sabah, 88400, Kota Kinabalu, Sabah, Malaysia

    Chin-Soon Phan, Chun-Sieng Yee & Charles Santhanaraju Vairappan

  2. Department of Bioscience and Biotechnology, Faculty of Agriculture, University of the Ryukyus, 1 Senbaru, Okinawa, Nishihara, 903-0213, Japan

    Takahiro Ishii

  3. Department of Materials and Life Science, Faculty of Science and Technology, Shizuoka Institute of Science and Technology, 2200-2 Toyosawa, Fukuroi, Shizuoka, 437-8555, Japan

    Takashi Kamada

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  1. Chin-Soon Phan
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  2. Chun-Sieng Yee
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  3. Charles Santhanaraju Vairappan
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  4. Takahiro Ishii
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  5. Takashi Kamada
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Correspondence to Takashi Kamada.

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Published in Khimiya Prirodnykh Soedinenii, No. 2, March–April, 2019, pp. 246–248.

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Phan, CS., Yee, CS., Vairappan, C.S. et al. Sinulaflexiolide P, A Cembrane-Type Diterpenoid from Bornean Soft Coral Sinularia flexibilis. Chem Nat Compd 55, 285–288 (2019). https://doi.org/10.1007/s10600-019-02668-w

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  • DOI: https://doi.org/10.1007/s10600-019-02668-w

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