Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia
Cytotoxic and antimicrobial constituents of the bark of Diospyros maritima collected in two geographical locations in Indonesia
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DOI：
10.1021/np040027m
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发表时间：
2004-07-01
影响因子：
5.1
通讯作者：
Oberlies, NH
中科院分区：
文献类型：
--
作者：
Gu, JQ;Graf, TN;Oberlies, NH
从印度尼西亚，一个收集在海平面的海滩森林在爪哇和其他收集在一个轻微的海拔远离海海岸的龙目岛的两个柿树皮样品的提取物的生物活性导向分馏，产生了一组不同的次生代谢产物。萘醌白花丹素（1），虽然发现在两个标本的提取物，构成了一个更大的百分比前一个样品，这也产生了一系列的白花丹素二聚体，maritinone（2），chitranone（3），和zeylanone（4）。后一个样品产生了一种新的萘醌衍生物，（4S）-shinanolone（5），和一种新的天然产物香豆素，7，8-二甲氧基-6-羟基香豆素（6），沿着产生了另外三种白花丹素类似物，2-甲氧基-7-甲基胡桃醌（7），3-甲氧基-7-甲基胡桃醌（8）和7-甲基胡桃醌（9）。化合物5和6的结构通过物理、光谱和化学方法进行了表征。所有的菌株进行了评价，在细胞毒性和抗菌试验，并提出这些萘醌的构效关系。还在中空纤维测定中评价了白花丹素（1）和maritinone（2）的体内抗肿瘤活性，但发现两者均无活性。
Bioactivity-directed fractionation of extracts of two Diospyros maritima bark samples from Indonesia, one collected at sea level in a beach forest in Java and the other collected at a slight elevation away from the sea shore on the island of Lombok, yielded a diverse set of secondary metabolites. The naphthoquinone plumbagin (1), although found in extracts of both specimens, constituted a much larger percentage of the former sample, which also yielded a series of plumbagin dimers, maritinone (2), chitranone (3), and zeylanone (4). The latter sample yielded a new naphthoquinone derivative, (4S)-shinanolone (5), and a new natural product coumarin, 7,8-dimethoxy-6-hydroxycoumarin (6), along with three other analogues of plumbagin, 2-methoxy-7-methyljuglone (7), 3-methoxy-7-methyljuglone (8), and 7-methyljuglone (9). The structures of compounds 5 and 6 were elaborated by physical, spectral, and chemical methods. All of the isolates were evaluated in both cytotoxicity and antimicrobial assays, and structure-activity relationships of these naphthoquinones are proposed. Plumbagin (1) and maritinone (2) were evaluated also for in vivo antitumor activity in the hollow fiber assay, but both were found to be inactive.