New colchicinoids from a native Jordanian meadow saffron, Colchicum brachyphyllum:: Isolation of the first naturally occurring dextrorotatory colchicinoid
New colchicinoids from a native Jordanian meadow saffron, Colchicum brachyphyllum:: Isolation of the first naturally occurring dextrorotatory colchicinoid
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DOI：
10.1021/np0496587
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发表时间：
2005-02-01
影响因子：
5.1
通讯作者：
Oberlies, NH
中科院分区：
文献类型：
--
作者：
Alali, FQ;El-Elimat, T;Oberlies, NH
作为我们对约旦秋水仙属物种的持续调查的一部分，对秋水仙属短叶秋水仙的生物活性成分进行了研究。利用生物活性导向分级分离，九个秋水仙素的分离和表征。其中一种具有新颖的环系统，我们将其命名为（+）-去美秋水仙酮（9），它代表了第一种天然存在的右旋秋水仙素。另一种分离的化合物是一种新的秋水仙素类似物，（-）-2，3-dimethyldemecolcine（8），而其余7种已知的秋水仙素是新的物种：（-）-秋水仙碱（1），（-）-3-去甲基秋水仙碱（2），（-）-山茱萸碱（3），β-光秋水仙碱（4），（-）-雄联苯碱（5），（-）-地美秋水仙碱（6），和（-）-3-去甲基地美可辛（7）。利用卤虫致死试验指导秋水仙素类化合物的分离。此外，评价所有纯化合物对人癌细胞组的细胞毒性，在一系列细菌和真菌（包括酵母）中的抗微生物活性，以及它们作为γ-氨基丁酸A型受体的变构调节剂的潜力。
As part of our continuing investigation of Jordanian Colchicum species, the biologically active components of Colchicum brachyphyllum were pursued. Using bioactivity-directed fractionation, nine colchicinoids were isolated and characterized. One of these has a novel ring system, to which we have ascribed the trivial name (+)-demecolcinone (9), and it represents the first naturally occurring dextrorotatory colchicinoid. Another isolated compound was a new colchicinoid analogue, (-)-2,3-didemethyldemecolcine (8), while the remaining seven known colchicinoids were new to the species: (-)-colchicine (1), (-)-3-demethylcolchicine (2), (-)-cornigerine (3), beta-lumicolchicine (4), (-)-androbiphenyline (5), (-)-demecolcine (6), and (-)-3-demethyldemecolcine (7). The brine shrimp lethality test was used to direct the isolation of these colchicinoids. Moreover, all pure compounds were evaluated for cytotoxicity against a human cancer cell panel, for antimicrobial activity in an array of bacteria and fungi (including yeast), and for their potential to be allosteric modulators of the gamma-aminobutyric acid type A receptor.