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

• Published in: Chirality (New York, N.Y.) Vol. 24; no. 5; pp. 386 - 390
• Main Authors: Shi, Xin-Wei, Zhang, An-Ling, Pescitelli, Gennaro, Gao, Jin-Ming
• Format: Journal Article
• Language: English
• Published: Chichester, UK John Wiley & Sons, Ltd 01.05.2012
• 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
• ISSN: 0899-0042; 1520-636X
• DOI: 10.1002/chir.22031

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.