2β-Acetoxyferruginol—A new antibacterial abietane diterpene from the bark of Prumnopitys andina

Eileen C. J. Smith, Neale Wareham, Mire Zloh, Simon Gibbons

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Abstract

As part of an on-going project to isolate antibacterial compounds from rare conifer species, a new abietane diterpene, 2β-acetoxyferruginol was isolated from the stem bark of Prumnopitys andina. Molecular modelling studies were conducted to explain some of the NOEs observed in the A-ring of this compound and to support assignment of relative stereochemistry. This new compound had antibacterial activity at 8 μg/ml against two effluxing strains of Staphylococcus aureus, but interestingly was inactive at 128 μg/ml against a wild-type strain and against a methicillin-resistant (MRSA) clinical isolate. We have previously demonstrated that ferruginol is active against these four S. aureus stains and therefore the results indicate that the presence of the acetoxy group has a detrimental effect on antibacterial activity against certain strains. 2β-Acetoxyferruginol was also assayed against Propionibacterium acnes and was active at 4 μg/ml.
Original languageEnglish
Pages (from-to)49-53
Number of pages5
JournalPhytochemistry Letters
Volume1
Issue number1
Early online date21 Feb 2008
DOIs
Publication statusPublished - 15 Apr 2008

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