Antimicrobial Prenylated Acetophenones from Berries of Harrisonia abyssinica

Abstract

The ripe berries of Harrisonia abyssinica yielded two new prenylated acetophenones, namely 5-(ethan-1′′′-one)-4,6-dihydroxy-7-(3′′,3′′-dimethylallyl)-2S-(1′S-hydroxy-1′,5′-dimethylhex-4′-enyl)-2,3-dihydrobenzofuran (1) and 5-(2′′′-hydroxyethan-1′′′-one)-4,6-dihydroxy-7-(3′′,3′′-dimethylallyl)-2S-(1′S-hydroxy-1′,5′-dimethylhex-4′-enyl)-2,3-dihydrobenzofuran (2), herein named harronin I and harronin II, respectively. The compounds were isolated following activity guided fractionation and the structures were determined using 1D, 2D NMR spectroscopic, CD and MS spectrometric techniques. The methanol-dichloromethane mixture (1 : 1 v/v) crude extract exhibited strong antimicrobial activity against Candida albicans, Bacillus cereus, Escherichia coli, Salmonella typhimurium, Staphylococcus aureus, and Lactobacillus casei. Harronin I (1) showed a MIC of 5 µg/mL against C. albicans, 6 µg/mL against B. cereus, and more than 20 µg/mL against other tested microorganisms. Harronin II (2) showed much weaker MIC values (> 100 µg/mL) against all the tested microorganisms.

Harrisonia abyssinica - Simaroubaceae - harronin I - harrorin II - prenylated acetophenones - antimicrobial activity

References

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