New bisabolane sesquiterpenoids from a marine-derived fungus Aspergillus sp isolated from the sponge Xestospongia testudinaria

被引:55
作者
Sun, Ling-Ling [1 ]
Shao, Chang-Lun [1 ]
Chen, Jian-Feng [3 ]
Guo, Zhi-Yong [3 ]
Fu, Xiu-Mei [1 ]
Chen, Min [1 ]
Chen, Yi-Yan [1 ]
Li, Rui [1 ]
de Voogd, Nicole J. [4 ]
She, Zhi-Gang [2 ]
Lin, Yong-Cheng [2 ]
Wang, Chang-Yun [1 ]
机构
[1] Ocean Univ China, Minist Educ China, Sch Med & Pharm, Key Lab Marine Drugs, Qingdao 266003, Peoples R China
[2] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China
[3] China Three Gorges Univ, Coll Chem & Life Sci, Yichang 443002, Peoples R China
[4] Netherlands Ctr Biodivers Naturalis, NL-2300 RA Leiden, Netherlands
基金
中国国家自然科学基金;
关键词
Phenolic bisabolane sesquiterpenoid; Marine-derived fungus; Aspergillus sp; Sponge; Cytotoxic activity; SYDONIC ACID; (+)-CURCUPHENOL; METABOLITES;
D O I
10.1016/j.bmcl.2011.12.083
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Three new phenolic bisabolane sesquiterpenoid dimers, disydonols A-C (1-3), and one known compound (S)-(+)-sydonol (4) were isolated from the fermentation broth of a marine-derived fungus Aspergillus sp., which was isolated from the sponge Xestospongia testudinaria collected from the South China Sea. Their structures were elucidated on the basis of comprehensive spectral analysis including 1D and 2D NMR spectra and HR-ESI-MS. These compounds were evaluated for cytotoxic activity against HepG-2 and Caski human tumour cell lines. Among them, compounds 1 and 3 exhibited cytotoxicity against the two cell lines. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1326 / 1329
页数:4
相关论文
共 19 条
[1]   AROMATIC BISABOLENES FROM AN AUSTRALIAN MARINE SPONGE, ARENOCHALINA SP [J].
BUTLER, MS ;
CAPON, RJ ;
NADESON, R ;
BEVERIDGE, AA .
JOURNAL OF NATURAL PRODUCTS, 1991, 54 (02) :619-623
[2]   Stereochemical determination and bioactivity assessment of (S)-(+)-curcuphenol dimers isolated from the marine sponge Didiscus aceratus and synthesized through laccase biocatalysis [J].
Cichewicz, RH ;
Clifford, LJ ;
Lassen, PR ;
Cao, XL ;
Freedman, TB ;
Nafie, LA ;
Deschamps, JD ;
Kenyon, VA ;
Flanary, JR ;
Holman, TR ;
Crews, P .
BIOORGANIC & MEDICINAL CHEMISTRY, 2005, 13 (19) :5600-5612
[3]   (+)-CURCUPHENOL AND DEHYDROCURCUPHENOL, NOVEL SESQUITERPENES WHICH INHIBIT H,K-ATPASE, FROM A MARINE SPONGE EPIPOLASIS SP [J].
FUSETANI, N ;
SUGANO, M ;
MATSUNAGA, S ;
HASHIMOTO, K .
EXPERIENTIA, 1987, 43 (11-12) :1234-1235
[4]   2 NEW METABOLITES, SYDONIC ACID AND HYDROXYSYDONIC ACID, FROM ASPERGILLUS-SYDOWI [J].
HAMASAKI, T ;
NAGAYAMA, K ;
HATSUDA, Y .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1978, 42 (01) :37-40
[5]   The structure and probable biogenesis of helianane, a heterocyclic sesquiterpene, from the Indo-Pacific sponge Haliclona ?fascigera [J].
Harrison, B ;
Crews, P .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (08) :2646-2648
[6]  
HENNE P, 1993, LIEBIGS ANN CHEM, P565
[7]   Asymmetric total synthesis of (+)-curcutetraol and (+)-sydonol [J].
Ito, Suguru ;
Zhang, Chenxia ;
Hosoda, Naoya ;
Asami, Masatoshi .
TETRAHEDRON, 2008, 64 (42) :9879-9884
[8]   Isolation and Absolute Stereochemistry of Optically Active Sydonic Acid from Glonium sp (Hysteriales, Ascomycota) [J].
Kudo, Shinji ;
Murakami, Takanori ;
Miyanishi, Junsuke ;
Tanaka, Kazuaki ;
Takada, Noboru ;
Hashimoto, Masaru .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2009, 73 (01) :203-204
[9]   Stereoselectivity in drug metabolism [J].
Lu, Hong .
EXPERT OPINION ON DRUG METABOLISM & TOXICOLOGY, 2007, 3 (02) :149-158
[10]   Cytotoxic Polyphenols from the Marine-Derived Fungus Penicillium expansum [J].
Lu, Zhenyu ;
Zhu, Huajie ;
Fu, Peng ;
Wang, Yi ;
Zhang, Zhihua ;
Lin, Haipeng ;
Liu, Peipei ;
Zhuang, Yibin ;
Hong, Kui ;
Zhu, Weiming .
JOURNAL OF NATURAL PRODUCTS, 2010, 73 (05) :911-914