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 

机构地区：[1]Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation,School of Pharmacy,Tongji Medical College,Huazhong University of Science and Technology,Wuhan 430030,China [2]State Key Laboratory of Phytochemistry and Plant Resources in West China,Kunming Institute of Botany,Chinese Academy of Sciences,Kunming 650201,China

出　　处：《Chinese Chemical Letters》2023年第4期183-187,共5页中国化学快报（英文版）

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)。

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[11.2.1.0^(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.

关 键 词：Rhododendron dauricum L.(Ericaceae) Diterpenoids Single-crystal X-ray diffraction Biosynthetic pathways ANALGESICS 

分 类 号：TQ460.1[化学工程—制药化工]