Micranthanone A, a New Diterpene with an Unprecedented Carbon Skeleton from Rhododendron micranthum

A new diterpene with an unprecedented carbon skeleton, micranthanone A (1), two new grayanane diterpenoids bearing an unusual 5,6-(3,4-dihydroxylbenzylidene acetal) motif, rhodomicranols A (2) and B (3), and three known grayanane diterpenoids (4–6) were isolated from Rhododendron micranthum. Their s...

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Bibliographic Details
Published in:Organic letters 2013-06, Vol.15 (12), p.3094-3097
Main Authors: Zhang, Mengke, Zhu, Yan, Zhan, Guanqun, Shu, Penghua, Sa, Rongjian, Lei, Liang, Xiang, Ming, Xue, Yongbo, Luo, Zengwei, Wan, Qian, Yao, Guangmin, Zhang, Yonghui
Format: Article
Language:English
Subjects:
Carbon - chemistry
Crystallography, X-Ray
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
Immunologic Factors - analysis
Immunologic Factors - chemistry
Models, Molecular
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Rhododendron - chemistry
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Summary:A new diterpene with an unprecedented carbon skeleton, micranthanone A (1), two new grayanane diterpenoids bearing an unusual 5,6-(3,4-dihydroxylbenzylidene acetal) motif, rhodomicranols A (2) and B (3), and three known grayanane diterpenoids (4–6) were isolated from Rhododendron micranthum. Their structures were elucidated by spectroscopic analyses, calculated ECD, and single-crystal X-ray diffraction. The in vitro immunomodulatory activities of 1–6 were evaluated, and a plausible biogenetic pathway for 1 is proposed.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol401292y