Secoscabronine M, a novel diterpenoid from the Chinese bitter mushroom Sarcodon scabrosus

Secoscabronine M (1) is a hemiacetal cyathane diterpenoid that was isolated from the fruiting bodies of the basidiomycete Sarcodon scabrosus (Fr.) Karst. Compound 1 possesses a novel structure with a bond cleavage between C‐3 and C‐4. The structure of the new compound was elucidated by means of spec...

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Bibliographic Details
Published in:Chirality (New York, N.Y.) N.Y.), 2012-05, Vol.24 (5), p.386-390
Main Authors: Shi, Xin-Wei, Zhang, An-Ling, Pescitelli, Gennaro, Gao, Jin-Ming
Format: Article
Language:English
Subjects:
3,4‐secocyathane
4-secocyathane
absolute configuration
Animals
basidiomycetes
Basidiomycota - chemistry
Circular Dichroism
Diterpenes - chemistry
Diterpenes - isolation & purification
Diterpenes - pharmacology
Drug Evaluation, Preclinical
electronic circular dichroism
fungal metabolites
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Structure
Neurites - drug effects
PC12 Cells
Rats
Sarcodon scabrosus
structure elucidation
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Summary:Secoscabronine M (1) is a hemiacetal cyathane diterpenoid that was isolated from the fruiting bodies of the basidiomycete Sarcodon scabrosus (Fr.) Karst. Compound 1 possesses a novel structure with a bond cleavage between C‐3 and C‐4. The structure of the new compound was elucidated by means of spectroscopic methods, including two‐dimensional nuclear magnetic resonance experiments. The absolute configuration of 1 was established by analysis of circular dichroism spectroscopy and also by employing time‐dependent density functional theory calculations. In addition, compound 1 was confirmed to be an equilibrium mixture of two epimers (15S and 15R) at position C‐15 in polar solvents by one‐dimensional nuclear magnetic resonance analysis. Chirality 4:386–390, 2012. © 2012 Wiley Periodicals, Inc.
ISSN:0899-0042
1520-636X
DOI:10.1002/chir.22031