从贝壳松醇半合成环氧松烷二萜及其对 FXa 的抑制活性。
Semisynthesis of epoxy-pimarane diterpenoids from kirenol and their FXa inhibition activities.
机构信息
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Science, Peking University, Beijing 100191, China; Guangdong-Macau Traditional Chinese Medicine Technology Industrial Park Development Co., Ltd., Zhuhai 519000, China; Research Center for Traditional Chinese Medicine of Lingnan (Southern China), College of Pharmacy, Jian University, Guangzhou 510632, China.
Research Center for Traditional Chinese Medicine of Lingnan (Southern China), College of Pharmacy, Jian University, Guangzhou 510632, China.
出版信息
Bioorg Med Chem. 2019 Apr 1;27(7):1320-1326. doi: 10.1016/j.bmc.2019.02.032. Epub 2019 Feb 16.
Kirenol is one of the biologically active diterpenoids from Siegesbeckia pubescens. In terms of the high content and typical structure, many ent-diterpenoids separated from S. pubescens were presumed to be biologically related to kirenol. Among them, epoxy-pimarane diterpenoids are belonging to a special family of naturally occurring compounds that attracted our attentions on their putative biosynthesis pathway and biological activities. Here, we designed and synthesized two known 14,16-epoxy-pimarane diterpenoids (2 and 3) and five 8,15-epoxy-pimarane diterpenoids (4-8) from kirenol. Their absolute structures were determined by 1D and 2D NMR data and the absolute configurations of 4 were confirmed by X-ray crystallographic data. Their inhibition effects on factor Xa (FXa) were evaluated to assess the potentiality of epoxy-pimarane diterpenoids as FXa inhibitor agents.
基里醇是苍耳草中的一种具有生物活性的二萜类化合物。鉴于其含量高和典型结构，许多从苍耳草中分离得到的对映二萜类化合物被认为与基里醇具有生物学相关性。其中，环氧-松烷二萜类化合物属于一类特殊的天然存在的化合物，它们的假定生物合成途径和生物活性引起了我们的关注。在这里，我们设计并合成了两种已知的 14,16-环氧-松烷二萜类化合物（2 和 3）和五种 8,15-环氧-松烷二萜类化合物（4-8），它们均来源于基里醇。通过 1D 和 2D NMR 数据确定了它们的绝对结构，通过 X 射线晶体学数据确定了 4 的绝对构型。评估了它们对因子 Xa（FXa）的抑制作用，以评估环氧-松烷二萜类化合物作为 FXa 抑制剂的潜力。
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