Subscribe to RSS
DOI: 10.1055/s-2007-990240
© Georg Thieme Verlag KG Stuttgart · New York
Cytotoxic Mycoepoxydiene Derivatives from an Endophytic Fungus Phomopsis sp. Isolated from Hydnocarpus anthelminthicus
Publication History
Received: June 27, 2007
Revised: September 10, 2007
Accepted: September 12, 2007
Publication Date:
10 October 2007 (online)
Abstract
Mycoepoxydiene (1) and derivatives, deacetylmycoepoxydiene (2) and 2,3-dihydromycoepoxydiene (3), were isolated from a broth extract of the endophytic fungus, Phomopsis sp., which was isolated from a Thai medicinal plant, Hydnocarpus anthelminthicus. Compounds 1 and 2 exhibited potent cytotoxic activity, while a dihydro derivative 3 was inactive. The present work suggests that the α,β-unsaturated lactone moiety in mycoepoxydienes might be responsible for the cytotoxicity.
- Supporting Information for this article is available online at
- Supporting Information .
References
- 1 Shrestha K, Strobel G A, Shrivastava S P, Gewali M B. Evidence for paclitaxel from three new endophytic fungi of Himalayan yew of Nepal. Planta Med. 2001; 67 374-6.
- 2 Ma H Y, Song Y C, Mao Y Y, Jiang J H, Tan R X, Luo L. Endophytic fungal metabolite fumigaclavine C causes relaxation of isolated rat aortic rings. Planta Med. 2006; 72 87-92.
- 3 Shiono Y. Anthracobic acids A and B, two polyketides, produced by an endophytic fungus Anthracobia sp. Chem Biodivers. 2006; 3 217-23.
- 4 Wei G H, Yang X Y, Zhang J W, Gao J M, Ma Y Q, Fu Y Y. et al . Rhizobialide: a new stearolactone produced by Mesorhizobium sp. CCNWGX022, a rhizobial endophyte from Glycyrrhiza uralensis . Chem Biodivers. 2007; 4 893-8.
- 5 Eyberger A L, Dondapati R, Porter J R. Endophyte fungal isolates from Podophyllum peltatum produce podophyllotoxin. J Nat Prod. 2006; 69 1121-4.
- 6 Cai P, McPhail A T, Krainer E, Katz B, Pearce C, Boros C. et al . Mycoepoxydiene represents a novel class of fungal metabolites. Tetrahedron Lett. 1999; 40 1479-82.
- 7 Shen Y, Yang L, Huang Y, Zheng Z, Song S, Su W. Method for preparing deacetyl mycoepoxydiene from metabolite of Phomosis A-1 - 2-3 and its application in antitumor drugs and other bioactive precursor. Chinese Patent CN 1 903 858 A 20 070 131. Faming Zhuanli Shenqing Gongkai Shuomingshu 2007.
- 8 Liu J -S, Li L. Kadsulignans L-N, three dibenzocyclooctadiene lignans from Kadsura coccinea . Phytochemistry. 1995; 38 241-5.
- 9 Spencer G F, Flippen-Anderson J L. Isolation and X-ray structure determination of a neolignan from Clerodendron inerme seeds. Phytochemistry. 1981; 20 2757-9.
- 10 Takao K, Watanabe G, Yasui H, Tadano K. Total synthesis of (+/-)-mycoepoxydiene, a novel fungal metabolite having an oxygen-bridged cyclooctadiene skeleton. Org Lett. 2002; 4 2941-3.
- 11 Takao K, Yasui H, Yamamoto S, Sasaki D, Kawasaki S, Watanabe G. et al . Asymmetric total syntheses of (+)-mycoepoxydiene and related natural product (-)-1893A: application of one-pot ring-opening/cross/ring-closing metathesis to construct their 9-oxabicyclo[4.2.1]nona-2,4-diene skeleton. J Org Chem. 2004; 69 8789-95.
- 12 Lin X, Huang Y, Fang M, Wang J, Zheng Z, Su W. Cytotoxic and antimicrobial metabolites from marine lignicolous fungi, Diaporthe sp. FEMS Microbiol Lett. 2005; 251 53-8.
- 13 Tengchaisri T, Chawengkirttikul R, Rachaphaew N, Reutrakul V, Sangsuwan R, Sirisinha S. Antitumor activity of triptolide against cholangiocarcinoma growth in vitro and in hamsters. Cancer Lett. 1998; 33 169-75.
Dr. Prasat Kittakoop
Chulabhorn Research Institute
Vipavadee-Rangsit Highway
Bangkok 10210
Thailand
Phone: +66-86-975-5777
Fax: +662-574-0622 ext. 1513
Email: prasatkittakoop@yahoo.com
- www.thieme-connect.de/ejournals/toc/plantamedica