A New Epi-neoverrucosane-type Diterpenoid from the Liverwort Pleurozia subinflata in Borneo

doi:10.1007/s13659-020-00232-6

应用天然产物 ›› 2020, Vol. 10 ›› Issue (1): 51-56.DOI: 10.1007/s13659-020-00232-6

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A New Epi-neoverrucosane-type Diterpenoid from the Liverwort Pleurozia subinflata in Borneo

Takashi Kamada^1,2, Mary Lyn Johanis², Shean-Yeaw Ng², Chin-Soon Phan², Monica Suleiman², Charles S. Vairappan²

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

收稿日期:2020-01-09 修回日期:2020-02-06 出版日期:2020-02-24 发布日期:2020-02-29
通讯作者: Takashi Kamada
基金资助:
This research was financially supported by SaBC Grant [No. GL0070] and UMS Grant [SBK0258-SG-2016].

A New Epi-neoverrucosane-type Diterpenoid from the Liverwort Pleurozia subinflata in Borneo

Takashi Kamada^1,2, Mary Lyn Johanis², Shean-Yeaw Ng², Chin-Soon Phan², Monica Suleiman², Charles S. Vairappan²

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

Received:2020-01-09 Revised:2020-02-06 Online:2020-02-24 Published:2020-02-29
Contact: Takashi Kamada
Supported by:
This research was financially supported by SaBC Grant [No. GL0070] and UMS Grant [SBK0258-SG-2016].

摘要/Abstract

摘要： New bioactive 13-epi-neoverrucosane diterpenoid, 5β-acetoxy-13-epi-neoverrucosanic acid (1) along with three known secondary metabolites, 13-epi-neoverrucosan-5β-ol (2), chelodane (3) and (E)-β-farnesene (4) were isolated from the MeOH extract of east Malaysia's liverwort Pleurozia subinfl ata. The chemical structure of new compound was elucidated by the analyses of its spectroscopic data (FTIR, NMR and HR-ESI-MS). These epi-neoverrucosane-type compounds seem to be notable chemosystematic markers for P. subinflata in Borneo. Compound 3 was widespread in marine sponges however this is the first record for 3 to be found in liverwort. These metabolites were tested for their antifungal potentials against selected fungi from the marine environment. Compound 1 exhibited effective antifungal activity against Lagenidium thermophilum.

关键词: Epi-neoverrucosane, Diterpenoid, Pleurozia subinfl ata, Liverwort, Borneo

Abstract: New bioactive 13-epi-neoverrucosane diterpenoid, 5β-acetoxy-13-epi-neoverrucosanic acid (1) along with three known secondary metabolites, 13-epi-neoverrucosan-5β-ol (2), chelodane (3) and (E)-β-farnesene (4) were isolated from the MeOH extract of east Malaysia's liverwort Pleurozia subinfl ata. The chemical structure of new compound was elucidated by the analyses of its spectroscopic data (FTIR, NMR and HR-ESI-MS). These epi-neoverrucosane-type compounds seem to be notable chemosystematic markers for P. subinflata in Borneo. Compound 3 was widespread in marine sponges however this is the first record for 3 to be found in liverwort. These metabolites were tested for their antifungal potentials against selected fungi from the marine environment. Compound 1 exhibited effective antifungal activity against Lagenidium thermophilum.

Key words: Epi-neoverrucosane, Diterpenoid, Pleurozia subinfl ata, Liverwort, Borneo

Takashi Kamada, Mary Lyn Johanis, Shean-Yeaw Ng, Chin-Soon Phan, Monica Suleiman, Charles S. Vairappan. A New Epi-neoverrucosane-type Diterpenoid from the Liverwort Pleurozia subinflata in Borneo[J]. 应用天然产物, 2020, 10(1): 51-56.

参考文献

1. L. Hui, R.X. Xu, X.S. Zhang, T.T. Zhu, H.X. Lou, A.X. Cheng, Phytochemistry 159, 190-198 (2019)
2. Y. Asakawa, A. Ludwiczuk, J. Nat. Prod. 81, 641-660 (2018)
3. S.Y. Ng, T. Kamada, C.S. Vairappan, Rec. Nat. Prod. 11, 508-513 (2017)
4. S.Y. Ng, T. Kamada, M. Suleiman, C.S. Vairappan, Nat. Prod. Res. 32, 1832-1837 (2018)
5. S.Y. Ng, T. Kamada, C.S. Phan, M. Suleiman, C.S. Vairappan, Heterocycles 96, 1958-1965 (2018)
6. Y. Asakawa, A. Ludwiczuk, F. Nagashima, in Chemical Constituents of Bryophytes, ed. by A.D. Kinghorn. Progress in the Chemistry of Organic Natural Products, vol 95 (Springer, Vienna, 2013), p. 796
7. J. Wei, Y. Cheng, W.H. Guo, D.C. Wang, Q. Zhang, D. Li, J. Rong, J.M. Gao, Sci. Rep. 7, 8883-8896 (2017)
8. J. Wei, W.H. Guo, C.Y. Cao, R.W. Kou, Y.Z. Xu, M. Górecki, L.D. Bari, G. Pescitelli, J.M. Gao, Sci. Rep. 8, 2175-2189 (2018)
9. P.M. Dewick, Nat. Prod. Rep. 19, 181-222 (2002)
10. A. Matsuo, H. Nozaki, M. Nakayama, S. Hayashi, J. Chem. Soc. Chem. Commun. 5, 198-200 (1978)
11. C. Grammes, G. Burkhardt, M. Veith, V. Hugh, H. Becker, Phytochemistry 44, 1495-1502 (1997)
12. H.J. Liu, C.L. Wu, H. Becker, J. Zapp, Phytochemistry 53, 845-849 (2000)
13. H. Shimogawa, T. Teruya, K. Suenaga, H. Kigoshi, Bull. Chem. Soc. Jpn. 78, 1345-1347 (2005)
14. A.J. Singh, J.D. Dattelbaum, J.J. Field, Z. Smart, E.F. Woolly, J.M. Barber, R. Heathcott, J.H. Miller, P.T. Northcote, Org. Biomol. Chem. 11, 8041-8051 (2013)
15. A. Spyere, D.C. Rowley, P.R. Jensen, W. Fenical, J. Nat. Prod. 66, 818-822 (2003)
16. A. Banerjee, B. Hamberger, Phytochem. Rev. 17, 81-111 (2018)
17. A. Rudi, Y. Kashman, J. Nat. Prod. 55, 1408-1414 (1992)
18. Y. Asakawa, M. Toyota, H. Tanaka, T. Hashimoto, D. Joulain, J. Hattori Bot. Lab. 78, 183-188 (1995)
19. T. Yosief, A. Rudi, Z. Stein, I. Goldberg, G.M.D. Gravalos, M. Schleyer, Y. Kashman, Tetrahedron Lett. 39, 3323-3326 (1998)
20. J.M. Ryan, Ph.D Dissertation, Victoria University of Wellington, 2007
21. T. Kamada, C.S. Phan, T. Hamada, K. Hatai, C.S. Vairappan, Nat. Prod. Commun. 13, 17-19 (2018)
22. T. Kamada, J. Kulip, K. Tani, C.S. Phan, K. Hatai, C.S. Vairappan, Rec. Nat. Prod. 12, 317-322 (2018)
23. K.J. Shamsudin, C.S. Phan, J. Kulip, K. Hatai, C.S. Vairappan, T. Kamada, J. Asian Nat. Prod. Res. 21, 435-441 (2019)

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A New Epi-neoverrucosane-type Diterpenoid from the Liverwort Pleurozia subinflata in Borneo

A New Epi-neoverrucosane-type Diterpenoid from the Liverwort Pleurozia subinflata in Borneo

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