Oleanane triterpenes from Junellia tridens
Oleanane triterpenes from Junellia tridens
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DOI：
10.1021/np0002233
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发表时间：
2000-12-01
影响因子：
5.1
通讯作者：
Timmermann, BN
中科院分区：
文献类型：
--
作者：
Caldwell, CG;Franzblau, SG;Timmermann, BN
从阿根廷灌木Junellia tridens的地上部分分离得到三种新的三萜类化合物，3，4-断-降-12-烯-3，28-二酸（4），3 α-羟基降-11-烯-28，13 β-降（5）和3 α-羟基齐墩果烷-11：13（18）-二烯-28-酸（6）。另外还分离出了5个化合物，分别是齐墩果酸（1）、齐墩果酸（2）和表齐墩果酸（3），它们都与3个新的齐墩果烷类化合物生物合成有关，另外还分离出表桦木酸（7）和谷甾醇（8）。通过1D、2D NMR和质谱初步鉴定了化合物的结构，并对三个新化合物的质子和碳原子进行了完全归属。我们报告了这些化合物对结核分枝杆菌的最低抑制浓度，并得出结论，它们是负责最初在粗植物提取物中观察到的抗结核活性。LC-MS数据提供了其他六种Junellia中三萜1-6的存在情况。
Three novel triterpenes, 3,4-seco-olean-12-ene-3,28-dioic acid (4), 3 alpha -hydroxyolean-11-en-28,13 beta -olide (5), and 3 alpha -hydroxyoleane-11:13(18)-dien-28-oic acid (6), were isolated from the aerial parts of the Argentinean shrub, Junellia tridens. Another five compounds-oleanolic (1), oleanonic (2), and epioleanolic acids (3), all biosynthetically related to the three new oleananes, and epibetulinic acid (7) and sitosterol (8)-were also isolated. Structures were elucidated primarily by ID and 2D NMR and mass spectrometry, and all protons and carbons of the three novel compounds were fully assigned by NMR. We report the minimum inhibitory concentrations of these compounds against Mycobacterium tuberculosis and conclude that they are responsible for antitubercular activity originally observed in the crude plant extract. LC-MS data is provided on the occurrence of triterpenes 1-6 in six other species of Junellia.