抗病毒螺环三菇素 A 和 B：来自两面针 Toddalia asiatica 的两对具有螺环二烯酮-倍半萜骨架的寡聚香豆素对映体。

Antiviral Spirotriscoumarins A and B: Two Pairs of Oligomeric Coumarin Enantiomers with a Spirodienone-Sesquiterpene Skeleton from Toddalia asiatica.

机构信息

State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College , Beijing 100050, China.

出版信息

Org Lett. 2016 Oct 7;18(19):5146-5149. doi: 10.1021/acs.orglett.6b02572. Epub 2016 Sep 27.

DOI:10.1021/acs.orglett.6b02572

PMID:27673343

Abstract

Two pairs of oligomeric coumarin enantiomers, spirotriscoumarin A [(+)-1 and (-)-1] and spirotriscoumarin B [(+)-2 and (-)-2], with a spirodienone-sesquiterpene fused skeleton were isolated from Toddalia asiatica. Their structures were unambiguously established using spectroscopic data, X-ray diffraction analysis, and the electronic circular dichroism (ECD) method. The racemic mixtures (±)-1 and (±)-2 exhibit 3-to-6-fold stronger antiviral activity against influenza virus A (H3N2) (IC: 3.13 and 2.87 μM, respectively) than their corresponding optically pure enantiomers.

摘要

从苦茄中分离得到两对具有螺二氢呋喃-倍半萜骨架的寡聚香豆素对映体，螺三香豆素 A [(+)-1 和 (-)-1]和螺三香豆素 B [(+)-2 和 (-)-2]。利用光谱数据、X 射线衍射分析和电子圆二色性 (ECD) 方法，明确了它们的结构。外消旋混合物 (±)-1 和 (±)-2 对流感病毒 A (H3N2) 的抗病毒活性比其相应的光学纯对映体强 3 至 6 倍 (IC：分别为 3.13 和 2.87 μM)。