New Phenylethanoids from Buddleja cordata subsp. cordata

Abstract

Bioassay-guided fractionation of a crude extract of the stem bark of Buddleja cordata subsp. cordata with significant antimycobacterial activity led to the isolation of a mixture composed by ten new long-chain esters of 2[4′-hydroxyphenyl]-ethanol (1 - 10), along with the lichen metabolites methyl β-orcinolcarboxylate (11) and β-orcinolcarboxylate (12). Extensive HPLC allowed the separation of the major components of the mixture, which were characterized by spectral means as 2[4′-hydroxyphenyl]-ethyl stearate (3), 2[4′-hydroxyphenyl]-ethyl behenate (6), and 2[4′-hydroxyphenyl]-ethyl lignocerate (8). The minor esters were identified as 2[4′-hydroxyphenyl]-ethyl palmitate (1), 2[4′-hydroxyphenyl]-ethyl heptadecanoate (2), 2[4′-hydroxyphenyl]-ethyl nonadecanoate (4), 2[4′-hydroxyphenyl]-ethyl arachidate (5), 2[4′-hydroxyphenyl]-ethyl tricosanoate (7), 2[4′-hydroxyphenyl]-ethyl pentacosanoate (9), and 2[4′-hydroxyphenyl]-ethyl hexacosanoate (10) by GC-MS analysis of the methyl esters derivatives of the fatty acids obtained by alkaline hydrolysis of the mixture. Compound 8 exhibited moderate antibacterial activity against Mycobacterium tuberculosis (MIC = 64 μg/ml).

Key words

Buddleja cordata subsp. cordata - Loganiaceae - phenylethanoids - Mycobacterium tuberculosis - antimycobacterial activity - methyl β-orcinolcarboxylate - β-orcinolcarboxylate

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