New Limonoids from the Seeds of a Krishna Mangrove, Xylocarpus granatum
Hongliang Chen
College of Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, P. R. China, (phone: +86-431-84533087-8011; fax: +86-431-84533086)
Search for more papers by this authorCorresponding Author
Jing Zhang
College of Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, P. R. China, (phone: +86-431-84533087-8011; fax: +86-431-84533086)
Jing Zhang, College of Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, P. R. China, (phone: +86-431-84533087-8011; fax: +86-431-84533086)
Jun Wu, Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, P. R. China, (phone: +86-20-84458442; fax: +86-20-84451672)
Search for more papers by this authorMin-Yi Li
Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, P. R. China, (phone: +86-20-84458442; fax: +86-20-84451672)
Search for more papers by this authorTirumani Satyanandamurty
Government Degree College at Amadala valasa, Srikakulam District, Andhra Pradesh, 532185, India
Search for more papers by this authorCorresponding Author
Jun Wu
Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, P. R. China, (phone: +86-20-84458442; fax: +86-20-84451672)
Jing Zhang, College of Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, P. R. China, (phone: +86-431-84533087-8011; fax: +86-431-84533086)
Jun Wu, Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, P. R. China, (phone: +86-20-84458442; fax: +86-20-84451672)
Search for more papers by this authorHongliang Chen
College of Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, P. R. China, (phone: +86-431-84533087-8011; fax: +86-431-84533086)
Search for more papers by this authorCorresponding Author
Jing Zhang
College of Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, P. R. China, (phone: +86-431-84533087-8011; fax: +86-431-84533086)
Jing Zhang, College of Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, P. R. China, (phone: +86-431-84533087-8011; fax: +86-431-84533086)
Jun Wu, Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, P. R. China, (phone: +86-20-84458442; fax: +86-20-84451672)
Search for more papers by this authorMin-Yi Li
Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, P. R. China, (phone: +86-20-84458442; fax: +86-20-84451672)
Search for more papers by this authorTirumani Satyanandamurty
Government Degree College at Amadala valasa, Srikakulam District, Andhra Pradesh, 532185, India
Search for more papers by this authorCorresponding Author
Jun Wu
Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, P. R. China, (phone: +86-20-84458442; fax: +86-20-84451672)
Jing Zhang, College of Chinese Medicinal Materials, Jilin Agricultural University, Changchun 130118, P. R. China, (phone: +86-431-84533087-8011; fax: +86-431-84533086)
Jun Wu, Key Laboratory of Marine Bio-resources Sustainable Utilization, South China Sea Institute of Oceanology, Chinese Academy of Sciences, 164 West Xingang Road, Guangzhou 510301, P. R. China, (phone: +86-20-84458442; fax: +86-20-84451672)
Search for more papers by this authorAbstract
Two new mexicanolides, named granatumins H and I (1 and 2, resp.), and two phragmalins, named granatumins J and K (3 and 4, resp.), were isolated from the seeds of an Indian mangrove, Xylocarpus moluccensis, collected from the swamps of Krishna estuary, Andhra Pradesh. The structures of these limonoids were established on the basis of spectroscopic data. Granatumin J (3) is a highly oxidized phragmalin with five AcO groups, whereas granatumin K (4) is the first phragmalin found in nature with conjugated C(8)C(30) and C(14)C(15) bonds.
Graphical Abstract
References
- 1 J. Wu, Q. Xiao, J. Xu, M. Y. Li, J. Y. Pan, M. H. Yang, Nat. Prod. Rep. 2008, 25, 955.
- 2 W. M. Hu, J. Wu, Open Nat. Prod. J. 2010, 3, 1.
- 3 J. X. Cui, Z. W. Deng, M. J. Xu, P. Proksch, Q. Li, W. H. Lin, Helv. Chim. Acta 2009, 92, 139.
- 4 K. Pudhom, D. Sommit, P. Nuclear, N. Ngamrojanavanich, A. Petsom, J. Nat. Prod. 2009, 72, 2188.
- 5 J. Y. Pan, S. L. Chen, M. Y. Li, J. Li., M. H. Yang, J. Wu, J. Nat. Prod. 2010, 73, 1672.
- 6 L.-R. Shen, M. Dong, D. Guo, B.-W. Yin, M.-L. Zhang, Q.-W. Shi, C.-H. Huo, H. Kiyota, N. Suzuki, B. Cong, Z. Naturforsch., C: Biosci. 2009, 64, 37.
- 7 B. W. Yin, C. H. Huo, L. R. Shen, C. Wang, L. Zhao, Y. L. Wang, Q. W. Shi, Biochem. Syst. Ecol. 2009, 37, 218.
- 8 R. V. Hoffman, J. Am. Chem. Soc. 1976, 98, 6704.
- 9 S. Yin, X.-N. Wang, C.-Q. Fan, L.-P. Lin, J. Ding, J.-M. Yue, J. Nat. Prod. 2007, 70, 682.
- 10 J. X. Cui, J. Wu, Z. W. Deng, P. Proksch, W. H. Lin, J. Nat. Prod. 2007, 70, 772.
- 11 X. Fang, Y. T. Di, X. J. Hao, Curr. Org. Chem. 2011, 15, 1363.
- 12 A. S. Ng, A. G. Fallis, Can. J. Chem. 1979, 57, 3088.
- 13 K. A. Alvi, P. Crews, B. Aalbersberg, R. Prasad, J. Simpson, R. T. Weavers, Tetrahedron 1991, 47, 8943.
- 14 U. Kokpol, W. Chavasiri, S. Tip-pyang, G. Veerachato, F. L. Zhao, Phytochemistry 1995, 41, 903.
- 15 D. A. Mulholland, B. Parel, P. H. Coombes, Curr. Org. Chem. 2000, 4, 1011.
- 16 J. Wu, Q. Xiao, J. S. Huang, Z. H. Xiao, S. H. Qi, Q. X. Li, S. Zhang, Org. Lett. 2004, 6, 1841.
- 17 J. Wu, Q. Xiao, S. Zhang, X. Li, Z. H. Xiao, H. X. Ding, Q. X. Li, Tetrahedron 2005, 61, 8382.
- 18 J. Wu, S. Zhang, T. Bruhn, Q. Xiao, H. X. Ding, G. Bringmann, Chem. – Eur. J. 2008, 14, 1129.
- 19 M. Y. Li, S. X. Yang, J. Y. Pan, Q. Xiao, T. Satyanandamurty, J. Wu, J. Nat. Prod. 2009, 72, 1657.
- 20 M. Y. Li, X. B. Yang, J. Y. Pan, G. Feng, Q. Xiao, J. Sinkkonen, T. Satyanandamurty, J. Wu, J. Nat. Prod. 2009, 72, 2110.
- 21 J. Wu, X. B. Yang, M. Y. Li, G. Feng, J. Y. Pan, Q. Xiao, J. Sinkkonen, T. Satyanandamurty, J. Nat. Prod. 2010, 73, 644.
- 22
J. Zhang, S. X. Yang, X. B. Yang, M. Y. Li, G. Feng, J. Y. Pan, T. Satyanandamurty, J. Wu, Chem. Pharm. Bull. 2010, 54, 552.
10.1248/cpb.58.552 Google Scholar
- 23 J. Li, M. Y. Li, G. Feng, Q. Xiao, J. Sinkkonen, T. Satyanandamurty, J. Wu, Phytochemistry 2010, 71, 117.
- 24 G. Feng, J. Zhang, J. Li, T. Satyanandamurty, J. Wu, Acta Crystallogr., Sect. E: Struct. Rep. Online 2010, E66, o2111.
- 25 J. Li, M. Y. Li, T. Satyanandamurty, J. Wu, Helv. Chim. Acta 2011, 94, 1651.
- 26 M. M. Rao, E. M. S. Krishna, P. S. Gupta, Indian J. Chem. B 1978, 16, 823.
- 27 Y. Zhou, F. Cheng, J. Wu, K. Zou, J. Nat. Prod. 2006, 69, 1083.
