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

doi:10.1021/np060076u

	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
刊名	JOURNAL OF NATURAL PRODUCTS
	2006-09-22
卷号	69 期号:9 页码:1261-1266
关键词	Germacrane-type Sesquiterpene Rhodomela-confervoides Marine Plants Constituents Zonarioides Hydrocarbons
ISSN号	0163-3864
DOI	10.1021/np060076u
文献子类	Article
英文摘要	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.
学科主题	Plant Sciences ; Chemistry, Medicinal ; Pharmacology & Pharmacy
URL标识	查看原文
语种	英语
WOS记录号	WOS:000240677700002
公开日期	2010-11-18
内容类型	期刊论文
源URL	[http://ir.qdio.ac.cn/handle/337002/1877]
专题	海洋研究所_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.