超双氧杂蒽 A，贯叶连翘中二苯并-1,4-二氧杂环己烷与倍半萜的轭合物。

Hyperdioxane A, a Conjugate of Dibenzo-1,4-dioxane and Sesquiterpene from Hypericum ascyron.

机构信息

Graduate School of Pharmaceutical Sciences , Tokushima University , Tokushima 770-8505 , Japan.

Graduate School of Technology, Industrial and Social Sciences , Tokushima University , Tokushima 770-8513 , Japan.

出版信息

Org Lett. 2018 Sep 21;20(18):5977-5980. doi: 10.1021/acs.orglett.8b02739. Epub 2018 Sep 12.

DOI:10.1021/acs.orglett.8b02739

PMID:30207481

Abstract

Two new dibenzo-1,4-dioxane derivatives, hyperdioxanes A (1) and B (2), were isolated from the roots of a Hypericaceous plant, Hypericum ascyron. Hyperdioxane A (1) is a conjugate of dibenzo-1,4-dioxane and sesquiterpene with an unprecedented heptacyclic ring system. The structures of 1 and 2 were assigned by detailed spectroscopic analyses, including application of a modified Mosher's method. A possible biogenetic pathway of hyperdioxane A (1) from hyperdioxane B (2) and a sesquiterpene, eremophil-9,11(13)-dien-8β,12-olide (3), is presented.

摘要

从藤黄科植物贯叶金丝桃的根部分离得到了两个新的二苯并-1,4-二氧六环衍生物，即 hyperdioxanes A（1）和 B（2）。化合物 1 是二苯并-1,4-二氧六环与倍半萜的共轭物，具有前所未有的七环体系。通过详细的光谱分析，包括应用改良的 Mosher 法，确定了 1 和 2 的结构。提出了 hyperdioxane A（1）可能的生物合成途径，即由 hyperdioxane B（2）和倍半萜 eremophil-9,11(13)-dien-8β,12-olide（3）生成。