Norsesquiterpenes from the brown alga Dictyopteris divaricata

doi:10.1021/np040227y

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	Norsesquiterpenes from the brown alga Dictyopteris divaricata
	Song, FH ; Xu, XL ; Li, SA ; Wang, SJ; Zhao, JL; Cao, P ; Yang, YC ; Fan, X ; Shi, JG ; He, L ; Lu, Y; Fan, X, Chinese Acad Sci, Inst Oceanol, Qingdao 266071, Peoples R China
	2005-09-01
发表期刊	JOURNAL OF NATURAL PRODUCTS
ISSN	0163-3864
卷号	68 期号:9 页码:1309-1313
文章类型	Article
摘要	Three bisnorsesquiterpenes (1-3) with novel carbon skeletons and a norsesquiterpene (4) have been isolated from the brown alga Dictyopteris divaricata. By means of spectroscopic data including IR, HRMS, 1D and 2D NMR techniques, single-crystal X-ray diffraction, and CD, their structures including absolute configurations were proposed as (+)-1R,6S,9R)-1-hydroxyl-6-isopropyl-9-methylbicyclo[4.3.0]non-4-en3-one (1), (-)-(1S,6S,9R)-1-hydroxyl-6-isopropyl-9-methylbicyclo[4.3.0] non-4-en-3-one (2), (+)-(5S,6R,9S)5-hydroxyl-6-isopropyl-9-methylbicyclo [4.3.01 non-1-en-3-one (3), and (-)-(1R,7S,10R)-1-hydroxy-1lnorcadinan-5-en-4-one (4). Biogenetically, the carbon skeleton of 1-3 may be derived from the co-occurring cadinane skeleton by ring contraction and loss of two carbon units, and compound 4 from the oxidation of cadinane derivatives. Compounds 1-4 were inactive (IC50 > 10 mu g/mL) against several human cancer cell lines including lung adenocarcinoma (A549), stomach cancer (BGC-823), breast cancer (MCF-7), hepatoma (Bel7402), and colon cancer (HCT-8) cell lines.; Three bisnorsesquiterpenes (1-3) with novel carbon skeletons and a norsesquiterpene (4) have been isolated from the brown alga Dictyopteris divaricata. By means of spectroscopic data including IR, HRMS, 1D and 2D NMR techniques, single-crystal X-ray diffraction, and CD, their structures including absolute configurations were proposed as (+)-1R,6S,9R)-1-hydroxyl-6-isopropyl-9-methylbicyclo[4.3.0]non-4-en3-one (1), (-)-(1S,6S,9R)-1-hydroxyl-6-isopropyl-9-methylbicyclo[4.3.0] non-4-en-3-one (2), (+)-(5S,6R,9S)5-hydroxyl-6-isopropyl-9-methylbicyclo [4.3.01 non-1-en-3-one (3), and (-)-(1R,7S,10R)-1-hydroxy-1lnorcadinan-5-en-4-one (4). Biogenetically, the carbon skeleton of 1-3 may be derived from the co-occurring cadinane skeleton by ring contraction and loss of two carbon units, and compound 4 from the oxidation of cadinane derivatives. Compounds 1-4 were inactive (IC50 > 10 mu g/mL) against several human cancer cell lines including lung adenocarcinoma (A549), stomach cancer (BGC-823), breast cancer (MCF-7), hepatoma (Bel7402), and colon cancer (HCT-8) cell lines.
关键词	Germacrane-type Sesquiterpene Rhodomela-confervoides Marine Plants Constituents Zonarioides Hydrocarbons Acid
学科领域	Plant Sciences ; Chemistry, Medicinal ; Pharmacology & Pharmacy
DOI	10.1021/np040227y
URL	查看原文
收录类别	SCI ; IC
语种	英语
WOS记录号	WOS:000232169900001
引用统计	被引频次：27[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	http://ir.qdio.ac.cn/handle/337002/1878
专题	海洋生物技术研发中心
通讯作者	Fan, X, Chinese Acad Sci, Inst Oceanol, Qingdao 266071, Peoples R China
作者单位	1.Chinese Acad Sci, Inst Oceanol, Qingdao 266071, Peoples R China 2.Chinese Acad Med Sci, Inst Mat Med, Beijing 100050, Peoples R China 3.Peking Union Med Coll, Beijing 100050, Peoples R China 4.Beijing Normal Univ, Dept Chem, Beijing 100875, Peoples R China
推荐引用方式 GB/T 7714	Song, FH,Xu, XL,Li, SA,et al. Norsesquiterpenes from the brown alga Dictyopteris divaricata[J]. JOURNAL OF NATURAL PRODUCTS,2005,68(9):1309-1313.
APA	Song, FH.,Xu, XL.,Li, SA.,Wang, SJ.,Zhao, JL.,...&Fan, X, Chinese Acad Sci, Inst Oceanol, Qingdao 266071, Peoples R China.(2005).Norsesquiterpenes from the brown alga Dictyopteris divaricata.JOURNAL OF NATURAL PRODUCTS,68(9),1309-1313.
MLA	Song, FH,et al."Norsesquiterpenes from the brown alga Dictyopteris divaricata".JOURNAL OF NATURAL PRODUCTS 68.9(2005):1309-1313.

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