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

Shi XinWei | Zendy; Zhang AnLing | Zendy; Pescitelli Gennaro | Zendy; Gao JinMing | Zendy

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

Author(s) -

Shi XinWei,

Zhang AnLing,

Pescitelli Gennaro,

Gao JinMing

Publication year - 2012

Publication title -

chirality

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.43

H-Index - 77

eISSN - 1520-636X

pISSN - 0899-0042

DOI - 10.1002/chir.22031

Subject(s) - chemistry , hemiacetal , terpenoid , stereochemistry , epimer , vibrational circular dichroism , absolute configuration , circular dichroism , nuclear magnetic resonance spectroscopy , two dimensional nuclear magnetic resonance spectroscopy

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 (15 S and 15 R ) at position C‐15 in polar solvents by one‐dimensional nuclear magnetic resonance analysis. Chirality 4:386–390, 2012 . © 2012 Wiley Periodicals, Inc.

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