Minor sesquiterpenes with new carbon skeletons from the brown alga Dictyopteris divaricata

doi:10.1021/np060076u

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	Minor sesquiterpenes with new carbon skeletons from the brown alga Dictyopteris divaricata
	Song, Fuhang ; Xu, Xiuli ; Li, Shuai ; Wang, Sujuan ; Zhao, Jielu ; Yang, Yongchun ; Fan, Xiao ; Shi, Jiangong ; He, Lan ; Shi, JG, Chinese Acad Sci, Inst Oceanol, Qingdao 266071, Peoples R China
	2006-09-22
发表期刊	JOURNAL OF NATURAL PRODUCTS
ISSN	0163-3864
卷号	69 期号:9 页码:1261-1266
文章类型	Article
摘要	Five minor sesquiterpenes (1-5) with two novel carbon skeletons, together with a minor new oplopane sesquiterpene ( 6), have been isolated from the brown alga Dictyopteris divaricata. By means of spectroscopic data including IR, HRMS, 1D and 2D NMR, and CD, their structures including absolute configurations were assigned as (+)-(1R, 5S, 6S, 9R)3- acetyl-1-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0] non-3-ene ( 1), (+)-(1R, 3S, 4S, 5R, 6S, 9R)-3-acetyl-1,4-dihydroxy-6- isopropyl-9-methylbicyclo[4.3.0] nonane (2), (+)-(1R, 3R, 4R, 5R, 6S, 9R)-3-acetyl-1,4-dihydroxy-6-isopropyl-9-methylbicyclo[ ;4.3.0] nonane ( 3), (+)-(1S, 2R, 6S, 9R)-1-hydroxy-2-(1-hydroxyethyl)-6-isopropyl-9-methylbicyclo[4.3.0] non-4-en-3-one (4), (-)-( 5S, 6R, 9S)-2-acetyl-5-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0] non-1-en-3-one ( 5), and (-)-( 1S, 6S, 9R)- 4-acetyl- 1-hydroxy-6-isopropyl-9-methylbicyclo[ 4.3.0] non-4-en-3-one ( 6). Biogenetically, the carbon skeletons of 1-6 may be derived from the co-occurring cadinane skeleton by different ring contraction rearrangements. Compounds 1-6 were inactive (IC50 > 10 mu g/mL) against several human cancer cell lines.; Five minor sesquiterpenes (1-5) with two novel carbon skeletons, together with a minor new oplopane sesquiterpene ( 6), have been isolated from the brown alga Dictyopteris divaricata. By means of spectroscopic data including IR, HRMS, 1D and 2D NMR, and CD, their structures including absolute configurations were assigned as (+)-(1R, 5S, 6S, 9R)3- acetyl-1-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0] non-3-ene ( 1), (+)-(1R, 3S, 4S, 5R, 6S, 9R)-3-acetyl-1,4-dihydroxy-6- isopropyl-9-methylbicyclo[4.3.0] nonane (2), (+)-(1R, 3R, 4R, 5R, 6S, 9R)-3-acetyl-1,4-dihydroxy-6-isopropyl-9-methylbicyclo[ ;4.3.0] nonane ( 3), (+)-(1S, 2R, 6S, 9R)-1-hydroxy-2-(1-hydroxyethyl)-6-isopropyl-9-methylbicyclo[4.3.0] non-4-en-3-one (4), (-)-( 5S, 6R, 9S)-2-acetyl-5-hydroxy-6-isopropyl-9-methylbicyclo[4.3.0] non-1-en-3-one ( 5), and (-)-( 1S, 6S, 9R)- 4-acetyl- 1-hydroxy-6-isopropyl-9-methylbicyclo[ 4.3.0] non-4-en-3-one ( 6). Biogenetically, the carbon skeletons of 1-6 may be derived from the co-occurring cadinane skeleton by different ring contraction rearrangements. Compounds 1-6 were inactive (IC50 > 10 mu g/mL) against several human cancer cell lines.
关键词	Germacrane-type Sesquiterpene Rhodomela-confervoides Marine Plants Constituents Zonarioides Hydrocarbons
学科领域	Plant Sciences ; Chemistry, Medicinal ; Pharmacology & Pharmacy
DOI	10.1021/np060076u
URL	查看原文
收录类别	SCI ; IC
语种	英语
WOS记录号	WOS:000240677700002
引用统计	被引频次：20[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/337002/1876
专题	海洋生物技术研发中心
通讯作者	Shi, JG, 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, Minist Educ, Key Lab Bioact Subst & Resources Utilizat Chinese, 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, Fuhang,Xu, Xiuli,Li, Shuai,et al. Minor sesquiterpenes with new carbon skeletons from the brown alga Dictyopteris divaricata[J]. JOURNAL OF NATURAL PRODUCTS,2006,69(9):1261-1266.
APA	Song, Fuhang.,Xu, Xiuli.,Li, Shuai.,Wang, Sujuan.,Zhao, Jielu.,...&Shi, JG, Chinese Acad Sci, Inst Oceanol, Qingdao 266071, Peoples R China.(2006).Minor sesquiterpenes with new carbon skeletons from the brown alga Dictyopteris divaricata.JOURNAL OF NATURAL PRODUCTS,69(9),1261-1266.
MLA	Song, Fuhang,et al."Minor sesquiterpenes with new carbon skeletons from the brown alga Dictyopteris divaricata".JOURNAL OF NATURAL PRODUCTS 69.9(2006):1261-1266.

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