Citation: Yuanyuan Feng, Suqin Zha, Hanqi Zhang, Biao Gao, Guijuan Zheng, Pengfei Jin, Yingyi Chen, Guangmin Yao. Rhodauricanol A, an analgesic diterpenoid with an unprecedented 5/6/5/7 tetracyclic system featuring a unique 16-oxa-tetracyclo[11.2.1.0^1,5.0^7,13]hexadecane core from Rhododendron dauricum[J]. Chinese Chemical Letters, ;2023, 34(4): 107742. doi: 10.1016/j.cclet.2022.107742 shu

Rhodauricanol A, an analgesic diterpenoid with an unprecedented 5/6/5/7 tetracyclic system featuring a unique 16-oxa-tetracyclo[11.2.1.0^1,5.0^7,13]hexadecane core from Rhododendron dauricum

Yuanyuan Feng ^a ,
Suqin Zha ^a ,
Hanqi Zhang ^a ,
Biao Gao ^a ,
Guijuan Zheng ^a ,
Pengfei Jin ^a ,
Yingyi Chen ^a ,
Guangmin Yao ^{a, b, *,}

a.
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
b.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China

gyap@mail.hust.edu.cn

Received Date: 8 May 2022
Revised Date: 7 August 2022
Accepted Date: 10 August 2022
Available Online: 14 August 2022

Figures(9)

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 first 1,3-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 ¹³C 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.
- Rhododendron dauricum L. (Ericaceae),
- Diterpenoids,
- Single-crystal X-ray diffraction,
- Biosynthetic pathways,
- Analgesics
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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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

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通讯作者: 陈斌, bchen63@163.com

Rhodauricanol A, an analgesic diterpenoid with an unprecedented 5/6/5/7 tetracyclic system featuring a unique 16-oxa-tetracyclo[11.2.1.0^1,5.0^7,13]hexadecane core from Rhododendron dauricum