Caldwell C G, Franzblau S G, Suarez E, Timmermann B N
Department of Pharmaceutical Sciences and Department of Pharmacology and Toxicology, Division of Medicinal Chemistry, College of Pharmacy, The University of Arizona, Tucson, Arizona 85721, USA.
J Nat Prod. 2000 Dec;63(12):1611-4. doi: 10.1021/np0002233.
Three novel triterpenes, 3,4-seco-olean-12-ene-3,28-dioic acid (4), 3alpha-hydroxyolean-11-en-28,13beta-olide (5), and 3alpha-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 1D 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.
从阿根廷灌木三齿朱奈莉亚（Junellia tridens）的地上部分分离出三种新型三萜化合物，即3,4-裂环齐墩果-12-烯-3,28-二酸（4）、3α-羟基齐墩果-11-烯-28,13β-内酯（5）和3α-羟基齐墩果-11:13(18)-二烯-28-酸（6）。还分离出另外五种化合物——齐墩果酸（1）、齐墩酮酸（2）和表齐墩果酸（3），这三种化合物在生物合成上均与三种新的齐墩果烷相关，以及桦木酸（7）和甾醇（8）。结构主要通过一维和二维核磁共振及质谱进行解析，三种新型化合物的所有质子和碳均通过核磁共振完全归属。我们报告了这些化合物对结核分枝杆菌的最低抑菌浓度，并得出结论，它们是粗植物提取物中最初观察到的抗结核活性的原因。提供了液相色谱-质谱数据，表明三萜化合物1-6在其他六种朱奈莉亚属植物中的存在情况。
