Antimycobacterial cycloartanes from Borrichia frutescens
Antimycobacterial cycloartanes from Borrichia frutescens
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DOI：
10.1021/np960551w
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发表时间：
1996-12-01
影响因子：
5.1
通讯作者：
Franzblau, SG
中科院分区：
文献类型：
--
作者：
Cantrell, CL;Lu, TS;Franzblau, SG
在以生物测定为指导的美国东南部高等植物中寻找抗分枝杆菌化合物的过程中，我们对来自路易斯安那州沿海沼泽的海雏菊（Borrichia frutescens）的活性成分进行了化学研究。生物活性色谱馏分提供了两种新的三萜，(24R)-24,25-epoxycycloartan-3-one (1) 和 (23R)-3-oxolanosta-8,24-dien-23-ol (4) 和 (3 alpha H,24R)-24,25-epoxycycloartan-3-ol (3a)。化合物 3a 先前已分离为 C-24 差向异构体的混合物。通过光谱方法和化学转化确定了1、3a和4的结构，并通过单晶X射线衍射确定了1和4的分子结构。在针对结核分枝杆菌的放射呼吸生物测定中，环氧环阿烷1和3a表现出8μg/mL的最低抑制浓度。相反，羊毛甾二烯型三萜4在128μg/mL时没有表现出明显的抑制作用，乙酸酯3b也是如此。 Vero 细胞的细胞毒性对三萜 1、3a 和 4 的 IC50 值分别为 71.8、39.8 和 103.6 μg/mL。
In a bioassay-guided search for antimycobacterial compounds from higher plants of the southeastern United States, we have chemically investigated the sea daisy (Borrichia frutescens) from coastal marshes of Louisiana for their active constituents. Bioactive chromatographic fractions provided two new triterpenes, (24R)-24,25-epoxycycloartan-3-one (1) and (23R)-3-oxolanosta-8,24-dien-23-ol (4), and (3 alpha H,24R)-24,25-epoxycycloartan-3-ol (3a). Compound 3a had been previously isolated as a mixture of C-24 epimers. The structures of 1, 3a, and 4 were established by spectroscopic methods and chemical transformations, and the molecular structures of 1 and 4 were determined by single-crystal X-ray diffraction. In a radiorespirometric bioassay against Mycobacterium tuberculosis, the epoxycycloartanes 1 and 3a exhibited minimum inhibitory concentrations of 8 mu g/mL. In contrast, the lanostadiene-type triterpene 4 showed no significant inhibition at 128 mu g/mL, as did the acetate 3b. Cytotoxicity for Vero cells gave IC50 values of 71.8, 39.8, and 103.6 mu g/mL for triterpenes 1, 3a, and 4, respectively.