Jaspiferin G, a new isomalabaricane-type triterpenoid from the sponge Jaspis stellifera
-
Wei-Guo Xu
and
Sheng-An Tang
Abstract
A new isomalabaricane-type triterpenoid, jaspiferin G (1), together with four known isomalabaricane-type triterpenoids, isogeoditin A (2), 13-(E)-isogeoditin A (3), jaspolide E (4), and 22,23-dihydrostellettin D (5), was isolated from the marine sponge Jaspis stellifera. The structures were elucidated on the basis of spectroscopic data (1H and 13C NMR, 1H-1H COSY, HSQC, HMBC, and ROESY) and mass spectrometry.
Funding source: National Natural Science Foundation of China
Award Identifier / Grant number: 81102371
Funding source: Natural Science Foundation of Tianjin
Award Identifier / Grant number: 10JCYBJC15000
Funding statement: This work was supported in part by the National Natural Science Foundation of China (Grant No. 81102371) and the Natural Science Foundation of Tianjin, China (Grant No. 10JCYBJC15000).
Acknowledgments
This work was supported in part by the National Natural Science Foundation of China (Grant No. 81102371) and the Natural Science Foundation of Tianjin, China (Grant No. 10JCYBJC15000).
References
1. Tasdemir D, Manqalindan GC, Concepcion GP, Verbitski SM, Rabindran S, Miranda M, et al. Bioactive isomalabaricane triterpenes from the marine sponge Rhabdastrella globostellata. J Nat Prod 2002;65:210–4.10.1021/np0104020Search in Google Scholar PubMed
2. Jin DJ, Tang SA, Xing GS, Zhao WJ, Zhao C, Duan HQ, et al. Jaspiferins C-F, four new isomalabaricane-type triterpenoids from the South China Sea sponge Jaspis stellifera. J Asian Nat Prod Res 2014;16:427–33.10.1080/10286020.2014.911288Search in Google Scholar PubMed
3. Tang SA, Pei YH, Fu HZ, Deng ZW, Li J, Proksch P, et al. Jaspolides A-F, six new isomalabaricane-type terpenoids from the sponge Jaspis sp. Chem Pharm Bull 2006;54:4–8.10.1248/cpb.54.4Search in Google Scholar PubMed
4. Tang SA, Deng ZW, Proksch P, Lin WH. Jaspolides G and H, unique bisisomalabaricanes from the Chinese marine Sponge Jaspis sp. Tetrahedron Lett 2007;48:5443–7.10.1016/j.tetlet.2007.06.003Search in Google Scholar
5. Tang SA, Deng ZW, Li J, Fu HZ, Pei YH, Zhang S, et al. A new isomalabaricane triterpenoid from sponge Jaspis sp. Chin Chem Lett 2005;16:353–5.Search in Google Scholar
6. Hirashima M, Tsuda K, Hamada T, Okamura H, Furukawa T, Akiyama S, et al. Cytotoxic isomalabaricane derivatives and a monocyclic triterpene glycoside from the sponge Rhabdastrella globostellata. J Nat Prod 2010;73:1512–8.10.1021/np100302aSearch in Google Scholar PubMed
7. Li J, Xu B, Cui JR, Deng ZW, De Voogd NJ, Proksch P, et al. Globostelletins A-I, cytotoxic isomalabaricane derivatives from the marine sponge Rhabdastrella globostellata. Bioorg Med Chem 2010;18:4639–47.10.1016/j.bmc.2010.05.029Search in Google Scholar PubMed
8. Lin HW, Wang ZL, Wu JH, Shi N, Zhang HJ, Chen WS, et al. Stellettins L and M, cytotoxic isomalabaricane-type triterpenes, and sterols from the marine sponge Stelletta tenuis. J Nat Prod 2007;70:1114–7.10.1021/np070069lSearch in Google Scholar PubMed
9. Zhang WH, Che CT. Isomalabaricane-type nortriterpenoids and other constituents of the marine sponge Geodia japonica. J Nat Prod 2001;64:1489–92.10.1021/np0100789Search in Google Scholar PubMed
10. Tang SA, Zhou Q, Guo WZ, Qiu Y, Wang R, Jin M, et al. In vitro antitumor activity of stellettin B, a triterpene from marine sponge Jaspis stellifera, on human glioblastoma cancer SF295 cells, Mar Drugs 2014;12:4200–13.10.3390/md12074200Search in Google Scholar PubMed PubMed Central
11. Wei SY, Li M, Tang SA, Sun W, Xu B, Cui JR, et al. Induction of apoptosis accompanying with G(1) phase arrest and microtubule disassembly in human hepatoma cells by jaspolide B, a new isomalabaricane-type triterpene, Cancer Lett 2008;262:114–22.10.1016/j.canlet.2007.11.039Search in Google Scholar PubMed
12. Lin J, Zhu HJ, Ren JW, Deng ZW, De Voogd NJ, Proksch P, et al. Globostelletins J-S, isomalabaricanes with unusual cyclopentane sidechains from the marine sponge Rhabdastrella globostellata. Tetrahedron 2012;68:559–65.10.1016/j.tet.2011.11.001Search in Google Scholar
13. Tanaka N, Momose R, Shibazaki A, Gonoi T, Fromont J, Kobayashi J. Stelliferins J-N, isomalabaricane-type triterpenoids from Okinawan marine sponge Rhabdastrella cf. globostellata. Tetrahedron 2011;67:6689–96.10.1016/j.tet.2011.04.095Search in Google Scholar
14. Lv F, Deng ZW, Li J, Fu HZ, Van Soest RW, Proksch P, et al. Isomalabaricane-type compounds from the marine sponge Rhabdastrella aff. distincta. J Nat Prod 2004;67:2033–6.10.1021/np040145+Search in Google Scholar PubMed
15. Zhang W, Yao Z, Zhang YW, Zhang XX, Takaishi Y, Duan HQ. Immunosuppressive sesquiterpenes from Buddleja davidii. Planta Med 2010;76:1882–7.10.1055/s-0030-1249974Search in Google Scholar PubMed
Supplemental Material:
The online version of this article (DOI: 10.1515/znc-2016-0054) offers supplementary material, available to authorized users.
©2016 by De Gruyter
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- Design, synthesis and evaluation of antitumor activity of new rotundic acid acylhydrazone derivatives
- Synthesis and in vitro anti-HIV-1 activity of a series of N-arylsulfonyl-3-propionylindoles
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