Pinelloside, an antimicrobial cerebroside from Pinellia ternata

• Published in: Phytochemistry (Oxford) 2003-10, Vol.64 (4), p.903-906
• Main Authors: Chen, J H, Cui, G Y, Liu, J Y, Tan, R X
• Format: Article
• Language: English
• Subjects: Anti-Infective Agents - chemistry; Anti-Infective Agents - isolation & purification; Anti-Infective Agents - pharmacology; Bacillus subtilis - drug effects; Candida albicans - drug effects; Cerebrosides - chemistry; Cerebrosides - isolation & purification; Cerebrosides - pharmacology; Microbial Sensitivity Tests; Molecular Structure; Pinellia - chemistry; Spectrum Analysis - methods; Staphylococcus aureus - drug effects
• ISSN: 0031-9422
• DOI: 10.1016/S0031-9422(03)00421-7

An antimicrobial cerebroside, pinelloside, was isolated from the air-dried tubers of Pinellia ternata (Thunb.) Breit. Its structure was determined as 1-O-beta-D-glucopyranosyl-(2S,3R,4E,11E)-2-(2'R-hydroxyhexadecenoylamino)-4,11-octadecadiene-1,3-diol by chemical transformation and extensive spectroscopic analyses (IR, MS, 1H and 13C NMR, DEPT as well as 2D NMR techniques HMBC, HMQC, 1H-1H COSY and NOESY). The antimicrobial assay showed that this compound was inhibitory to the growth of Bacillus subtilis, Staphylococcus aureus, Aspergillus niger and Candida albicans, with minimum inhibitory concentrations (MICs) of 20, 50, 30 and 10 microg/ml, respectively. The MICs of penicillin G against bacteria B. subtilis, S. aureus, E. coli, P. fluorescens and H. pylori were 0.80, 0.34, 0.56, 1.34 and 0.92, and those of ketoconazole against fungi A. niger, C. albicans and T. rubrum 0.90, 0.65 and 1.0 microg/ml, respectively.