Jaeger Rolf, Cuny Eckehard
Nat Prod Commun. 2016 Sep;11(9):1373-1390.
Terpenoids are a very prominent class of natural compounds produced in diverse genera of plants, fungi, algae and sponges. They gained significant -pharmaceutical value since prehistoric times, due to their broad spectrum of medical applications. The fragrant leaves of Eucalyptus trees are a rich source of terpenoids. Therefore this review starts by summarizing the main terpenoid compounds present in Eucalyptus globulus, E. citriodora, E. radiata.and E. resinifera and describing their biosynthetic pathways. Of the enormous number of pharmaceutically important terpenoids, this paper also reviews some well established and recently discovered examples and discusses their medical applications. In this context, the synthetic processes for (-)-menthol, (-)-cis-carveol, (+)-artemisinine, (+)-merrilactone A and (-)-sclareol are presented. The tricyclic sesquiterpene (-)-englerin A isolated from the stem bark of the Phyllanthus engleri plant (Euphorbiaceae) is highly active against certain renal cancer cell lines. In addition, recent studies showed that englerin A is also a potent and selective activator of TRPC4 and TRPC5 calcium channels. These important findings were the motivation for several renowned research labs to achieve a total synthesis of (-)-englerin A. Two prominent examples - Christmann and Metz - are compared and discussed in detail.
萜类化合物是一类非常重要的天然化合物,在植物、真菌、藻类和海绵的不同属中都有产生。自史前时代以来,由于其广泛的医学应用,它们就具有了重要的药用价值。桉树叶富含萜类化合物。因此,本综述首先总结了蓝桉、柠檬桉、辐射桉和树脂桉中存在的主要萜类化合物,并描述了它们的生物合成途径。在众多具有重要药用价值的萜类化合物中,本文还综述了一些已被充分证实和最近发现的例子,并讨论了它们的医学应用。在此背景下,介绍了(-)-薄荷醇、(-)-顺式香芹醇、(+)-青蒿素、(+)-美林内酯A和(-)-香紫苏醇的合成过程。从叶下珠属植物(大戟科)茎皮中分离出的三环倍半萜(-)-恩格勒灵A对某些肾癌细胞系具有高度活性。此外,最近的研究表明,恩格勒灵A也是TRPC4和TRPC5钙通道的有效和选择性激活剂。这些重要发现促使几个著名的研究实验室实现了(-)-恩格勒灵A的全合成。详细比较和讨论了两个突出的例子——克里斯曼和梅茨的合成方法。