Structure elucidation of two new xanthone derivatives from the marine fungus Penicillium sp (ZZF 32#) from the South China Sea

被引:50
作者
Shao, Changlun [1 ,2 ]
Wang, Changyun [2 ]
Wei, Meiyan [3 ]
Gu, Yucheng [4 ]
Xia, Xuekui [1 ]
She, Zhigang [1 ]
Lin, Yongcheng [1 ]
机构
[1] Sun Yat Sen Zhongshan Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China
[2] Ocean Univ China, Sch Med & Pharm, Qingdao 266003, Peoples R China
[3] Guangdong Med Coll, Sch Pharm, Dongguan 523808, Peoples R China
[4] Syngenta Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England
基金
中国国家自然科学基金;
关键词
NMR; H-1; C-13; 2D NMR; xanthone; mangrove fungus; structure elucidation;
D O I
10.1002/mrc.2293
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Two new xanthones, 8-(methoxycarbonyl)-1-hydroxy-9-oxo-9H-xanthene-3-carboxylic acid (1) and dimethyl 8-methoxy-9-oxo-9H-xanthene-1, 6-dicarboxylate (2) and one known xanthone methyl 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (3) were isolated from the culture broth of the mangrove fungus Penicillium sp. (ZZF 32#) collected from the South China Sea. Their structures were established by comprehensive analysis of one-dimensional (1D) and two-dimensional (2D) NMR data. The structure of compound 3 was confirmed by X-ray crystallography, which led to the suggestion that janthinone (4) might have the same structure as 3. Compounds 1-3 were inactive against KB or KBv200 cells during cytotoxicity evaluations. Copyright (C) 2008 John Wiley & Sons, Ltd.
引用
收藏
页码:1066 / 1069
页数:4
相关论文
共 17 条
[1]   Two new xanthone derivatives from the algicolous marine fungus Wardomyces anomalus [J].
Abdel-Lateff, A ;
Klemke, C ;
König, GM ;
Wright, AD .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (05) :706-708
[2]   Marine natural products [J].
Blunt, JW ;
Copp, BR ;
Munro, MHG ;
Northcote, PT ;
Prinsep, MR .
NATURAL PRODUCT REPORTS, 2006, 23 (01) :26-78
[3]   Marine-derived fungi: a chemically and biologically diverse group of microorganisms [J].
Bugni, TS ;
Ireland, CM .
NATURAL PRODUCT REPORTS, 2004, 21 (01) :143-163
[4]   Two new metabolites of a marine endophytic fungus (No. 1893) from an estuarine mangrove on the South China Sea coast [J].
Chen, GY ;
Lin, YC ;
Wen, L ;
Vrijmoed, LLP ;
Jones, EBG .
TETRAHEDRON, 2003, 59 (26) :4907-4909
[5]   1H and 13C NMR assignments for two new xanthones from the endophytic fungus Xylaria sp FRR 5657 [J].
Davis, Rohan A. ;
Pierens, Gregory K. .
MAGNETIC RESONANCE IN CHEMISTRY, 2006, 44 (10) :966-968
[6]   Xanthones from a microfungus of the genus Xylaria [J].
Healy, PC ;
Hocking, A ;
Tran-Dinh, N ;
Pitt, JI ;
Shivas, RG ;
Mitchell, JK ;
Kotiw, M ;
Davis, RA .
PHYTOCHEMISTRY, 2004, 65 (16) :2373-2378
[7]   Phomoxanthones A and B, novel xanthone dimers from the endophytic fungus Phomopsis species [J].
Isaka, M ;
Jaturapat, A ;
Rukseree, K ;
Danwisetkanjana, K ;
Tanticharoen, M ;
Thebtaranonth, Y .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (08) :1015-1018
[8]   Chemical constituents of Garcinia fusca:: Structure elucidation of eight new xanthones and their cancer chemopreventive activity [J].
Ito, C ;
Itoigawa, M ;
Takakura, T ;
Ruangrungsi, N ;
Enjo, F ;
Tokuda, H ;
Nishino, H ;
Furukawa, H .
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (02) :200-205
[9]   ISOLATION OF MONILIPHENONE, A KEY INTERMEDIATE IN XANTHONE BIOSYNTHESIS FROM MONILINIA-FRUCTICOLA [J].
KACHI, H ;
SASSA, T .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1986, 50 (06) :1669-1671
[10]   The metabolites of the mangrove fungus Verruculina enalia No. 2606 from a salt lake in the Bahamas [J].
Lin, YC ;
Wu, XY ;
Deng, ZJ ;
Wang, J ;
Zhou, SN ;
Vrijmoed, LLP ;
Jones, EBG .
PHYTOCHEMISTRY, 2002, 59 (04) :469-471