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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.