Minor sesquiterpenes with new carbon skeletons from the brown alga Dictyopteris divaricata
Minor sesquiterpenes with new carbon skeletons from the brown alga Dictyopteris divaricata
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DOI：
10.1021/np060076u
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发表时间：
2006-09-22
影响因子：
5.1
通讯作者：
He, Lan
中科院分区：
文献类型：
--
作者：
Song, Fuhang;Xu, Xiuli;He, Lan
从棕色的叉叶网翅蕨（Dictyopterisdivaricata）中分离得到5个具有两个新碳骨架的次要倍半萜（1-5）和一个次要的新奥普罗烷型倍半萜（6）。通过IR、HRMS、1D和2D NMR、CD等波谱数据，确定了它们的结构（包括绝对构型）均为（+）-（1 R，5S，6S，9 R）3-乙酰基-1-羟基-6-异丙基-9-甲基双环[4.3.0]壬-3-烯（1），（+）-（1 R，3S，4S，5 R，6S，9 R）-3-乙酰基-1，4-二羟基-6-异丙基-9-甲基双环[4.3.0]壬烷（2），（+）-（1 R，3R，4 R，5 R，6S，9 R）-3-乙酰基-1，4-二羟基-6-异丙基-9-甲基双环[ ; 4.3.0]壬烷（3），（+）-（1 S，2 R，6S，9 R）-1-羟基-2-（1-羟乙基）-6-异丙基-9-甲基二环[4.3.0]壬-4-烯-3-酮（4），（-）-（5S，6 R，9 S）-2-乙酰基-5-羟基-6-异丙基-9-甲基二环[4.3.0]壬-1-烯-3-酮（5），和（-）-（1 S，6S，9 R）-4-乙酰基-1-羟基-6-异丙基-9-甲基双环[ 4.3.0]壬-4-烯-3-酮（6）。在生物遗传学上，1-6的碳骨架可能是通过不同的环收缩重排从共存的杜松烷骨架衍生而来的。化合物1-6对几种人癌细胞系无活性（IC 50> 10 μ g/mL）。
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.