Three Bianthraquinone Derivatives from the Mangrove Endophytic Fungus Alternaria sp ZJ9-6B from the South China Sea

被引:69
作者
Huang, Cai-Huan [1 ,2 ]
Pan, Jia-Hui [1 ]
Chen, Bin [1 ]
Yu, Miao [2 ]
Huang, Hong-Bo [1 ]
Zhu, Xun [3 ]
Lu, Yong-Jun [4 ]
She, Zhi-Gang [1 ,3 ]
Lin, Yong-Cheng [1 ,3 ]
机构
[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China
[2] Jinan Univ, Sch Sci & Engn, Guangzhou 510632, Guangdong, Peoples R China
[3] Sun Yat Sen Univ, Bur Educ Guangdong, Guangdong Prov Key Lab Funct Mol Ocean Microorgan, Guangzhou 510080, Guangdong, Peoples R China
[4] Sun Yat Sen Univ, Sch Life Sci, Guangzhou 510275, Guangdong, Peoples R China
基金
美国国家科学基金会; 中国国家自然科学基金;
关键词
endophytic fungus; Alternaria sp; bianthraquinone; alterporriol; cytotoxicity; METABOLIC PRODUCTS; PORRI; ELUCIDATION; KNIPHOLONE;
D O I
10.3390/md9050832
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Three new bianthraquinone derivatives, alterporriol K (1), L (2) and M (3), along with six known compounds were obtained from extracts of the endophytic fungus Alternaria sp. ZJ9-6B, isolated from the mangrove Aegiceras corniculatum collected in the South China Sea. Their structures were elucidated by one- and two-dimensional NMR spectroscopy, MS data analysis and circular dichroism measurements. Compounds 1, 2 and 3 were first isolated alterporriols with a C-2-C-2' linkage. The crystallographic data of tetrahydroaltersolanol B (7) was reported for the first time. In the primary bioassays, alterporriol K and L exhibited moderate cytotoxic activity towards MDA-MB-435 and MCF-7 cells with IC50 values ranging from 13.1 to 29.1 mu M.
引用
收藏
页码:832 / 843
页数:12
相关论文
共 24 条
[1]   BIANTHRAQUINONES AND A SPERMIDINE ALKALOID FROM CASSIA-FLORIBUNDA [J].
ALEMAYEHU, G ;
ABEGAZ, B ;
SNATZKE, G ;
DUDDECK, H .
PHYTOCHEMISTRY, 1988, 27 (10) :3255-3258
[2]   Bianthraquinones from the seeds of Senna muiltiglandulosa [J].
Alemayehu, G ;
Abegaz, BM .
PHYTOCHEMISTRY, 1996, 41 (03) :919-921
[3]   ISOLATION, IDENTIFICATION, AND MUTAGENICITY OF ALTERNARIOL MONOMETHYL ETHER [J].
AN, YH ;
ZHAO, TZ ;
MIAO, J ;
LIU, GT ;
ZHENG, YZ ;
XU, YM ;
VANETTEN, RL .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1989, 37 (05) :1341-1343
[4]   Stereochemistry of isoplagiochin C, a macrocyclic bisbibenzyl from liverworts [J].
Bringmann, G ;
Mühlbacher, J ;
Reichert, M ;
Dreyer, M ;
Kolz, J ;
Speicher, A .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (30) :9283-9290
[5]   Novel concepts in directed biaryl synthesis, part 100 -: Atropo-enantioselective total synthesis of knipholone and related antiplasmodial phenylanthraquinones [J].
Bringmann, G ;
Menche, D ;
Kraus, J ;
Mühlbacher, J ;
Peters, K ;
Peters, EM ;
Brun, R ;
Bezabih, M ;
Abegaz, BM .
JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) :5595-5610
[6]   Elucidation of the absolute configuration of knipholone and knipholone anthrone by quantum chemical CD calculations [J].
Bringmann, G ;
Kraus, J ;
Menche, D ;
Messer, K .
TETRAHEDRON, 1999, 55 (24) :7563-7572
[7]   Atroposelective synthesis of axially chiral biaryl compounds [J].
Bringmann, G ;
Mortimer, AJP ;
Keller, PA ;
Gresser, MJ ;
Garner, J ;
Breuning, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (34) :5384-5427
[8]   Anthraquinones from Gladiolus gandavensis [J].
Chen, B ;
Wang, DY ;
Ye, Q ;
Li, BG ;
Zhang, GL .
JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2005, 7 (03) :197-204
[9]   Inhibition of human tumor cell proliferation by novel anthraquinones from daylilies [J].
Cichewicz, RH ;
Zhang, YJ ;
Seeram, NP ;
Nair, MG .
LIFE SCIENCES, 2004, 74 (14) :1791-1799
[10]   Bioactive Metabolites from the Endophytic Fungus Stemphylium globuliferum Isolated from Mentha pulegium [J].
Debbab, Abdessamad ;
Aly, Amal H. ;
Edrada-Ebel, RuAngelie ;
Wray, Victor ;
Mueller, Werner E. G. ;
Totzke, Frank ;
Zirrgiebel, Ute ;
Schaechtele, Christoph ;
Kubbutat, Michael H. G. ;
Lin, Wen Han ;
Mosaddak, Mahjouba ;
Hakiki, Abdelhak ;
Proksch, Peter ;
Ebel, Rainer .
JOURNAL OF NATURAL PRODUCTS, 2009, 72 (04) :626-631