Rhodauricanol A, an analgesic diterpenoid with an unprecedented5/6/5/7 tetracyclic system featuring a unique16-oxa-tetracyclo[11.2.1.0^(1,5).0^(7,13)]hexadecane core from Rhododendron dauricum

作     者：Yuanyuan Feng Suqin Zha Hanqi Zhang Biao Gao Guijuan Zheng Pengfei Jin Yingyi Chen Guangmin Yao Yuanyuan Feng;Suqin Zha;Hanqi Zhang;Biao Gao;Guijuan Zheng;Pengfei Jin;Yingyi Chen;Guangmin Yao

作者机构：Hubei Key Laboratory of Natural Medicinal Chemistry and Resource EvaluationSchool of PharmacyTongji Medical CollegeHuazhong University of Science and TechnologyWuhan 430030China State Key Laboratory of Phytochemistry and Plant Resources in West ChinaKunming Institute of BotanyChinese Academy of SciencesKunming 650201China 

出 版 物：《Chinese Chemical Letters》 (中国化学快报（英文版）)

年 卷 期：2023年第34卷第4期

页      面：183-187页

核心收录：

学科分类：1007[医学-药学(可授医学、理学学位)] 10[医学] 

基　　金：supported by the Fund of State Key Laboratory of Phytochemistry and Plant Resources in West China (NoP2022-KF08) National Natural Science Foundation of China (Nos.22107033 and U1703109) the Scientific Research Project of Traditional Chinese Medicine of Hubei Provincial Health Commission (No. ZY2021M056) 

主　　题：Rhododendron dauricum L.(Ericaceae) Diterpenoids Single-crystal X-ray diffraction Biosynthetic pathways Analgesics 

摘      要：A novel diterpenoid with an unprecedented 5/6/5/7 tetracyclic system, rhodauricanol A(1), five new grayanane-derived diterpenoids, dauricanols A-E(2-6), and five known ones(7-11) were isolated from the flowers of Rhododendron dauricum. Rhodauricanol A(1) possesses a unique 5/6/5/7 tetracyclic ring system featuring a 16-oxa-tetracyclo[11.***.1.0^(1,5).0^(7,13)]hexadecane core. Dauricanols A-C(2-4) are the first1,3-dioxolane conjugates of grayanane diterpenoids and 5-hydroxymethylfurfural and vanillin, respectively, and dauricanols D(5) and E(6) represent the first examples of 6-deoxy-1,5-seco-grayanane diterpenoids. Their structures were determined by spectroscopic methods, quantum chemical calculation including ^(13)C NMR-DP4+ analysis and ECD calculation, and single-crystal X-ray diffraction analysis. Plausible biosynthetic pathways for 1-4 were proposed. All the isolates showed significant analgesic activities,and dauricanols B(3) and C(4) showed more potent analgesic activities than the positive control, morphine.