Rhodauricanol A, an analgesic diterpenoid with an unprecedented 5/6/5/7 tetracyclic system featuring a unique 16-oxa-tetracyclo[11.2.1.01,5.07,13]hexadecane core from Rhododendron dauricum

doi:10.1016/j.cclet.2022.107742

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	Rhodauricanol A, an analgesic diterpenoid with an unprecedented 5/6/5/7 tetracyclic system featuring a unique 16-oxa-tetracyclo[11.2.1.01,5.07,13]hexadecane core from Rhododendron dauricum
	Feng,Yuanyuan; Zha,Suqin; Zhang,Hanqi; Gao,Biao; Zheng,Guijuan; Jin,Pengfei; Chen,Yingyi; Yao,Guangmin
	2023
发表期刊	CHINESE CHEMICAL LETTERS
ISSN	1878-5964
卷号	34 期号:4 页码:107742
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[11.2.1.01,5.07,13]hexadecane core. Dauricanols A -C (2 -4) are the first 1,3-dioxolane conjugates of grayanane diterpenoids and 5-hydroxymethylfurfural and vanillin, respec-tively, and dauricanols D (5) and E (6) represent the first examples of 6-deoxy-1,5-seco-grayanane diter-penoids. Their structures were determined by spectroscopic methods, quantum chemical calculation in-cluding 13C NMR-DP4 + analysis and ECD calculation, and single-crystal X-ray diffraction analysis. Plausi-ble 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, mor-phine.(c) 2022 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
关键词	Rhododendron dauricum L (Ericaceae) Diterpenoids Single-crystal X-ray diffraction Biosynthetic pathways Analgesics
学科领域	Chemistry
DOI	10.1016/j.cclet.2022.107742
收录类别	SCI
WOS记录号	WOS:000920209400001
引用统计
文献类型	期刊论文
条目标识符	http://ir.kib.ac.cn/handle/151853/75455
专题	中国科学院昆明植物研究所
推荐引用方式 GB/T 7714	Feng,Yuanyuan,Zha,Suqin,Zhang,Hanqi,et al. Rhodauricanol A, an analgesic diterpenoid with an unprecedented 5/6/5/7 tetracyclic system featuring a unique 16-oxa-tetracyclo[11.2.1.01,5.07,13]hexadecane core from Rhododendron dauricum[J]. CHINESE CHEMICAL LETTERS,2023,34(4):107742.
APA	Feng,Yuanyuan.,Zha,Suqin.,Zhang,Hanqi.,Gao,Biao.,Zheng,Guijuan.,...&Yao,Guangmin.(2023).Rhodauricanol A, an analgesic diterpenoid with an unprecedented 5/6/5/7 tetracyclic system featuring a unique 16-oxa-tetracyclo[11.2.1.01,5.07,13]hexadecane core from Rhododendron dauricum.CHINESE CHEMICAL LETTERS,34(4),107742.
MLA	Feng,Yuanyuan,et al."Rhodauricanol A, an analgesic diterpenoid with an unprecedented 5/6/5/7 tetracyclic system featuring a unique 16-oxa-tetracyclo[11.2.1.01,5.07,13]hexadecane core from Rhododendron dauricum".CHINESE CHEMICAL LETTERS 34.4(2023):107742.

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