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Antifungal Garcinia Acid Esters from the Fruits of Garcinia atroviridis

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Antifungal Garcinia Acid Esters from the Fruits of Garcinia atroviridis

Mukram M. Mackeen

a,‡

, Abdul Manaf Ali

a

, Nordin Hj. Lajis

b,

*, Kazuyoshi Kawazu

c

, Hiroe Kikuzaki

d

, and Nobuji Nakatani

d

a Department of Biotechnology, Faculty of Food Science & Biotechnology, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia

b Institute of Bioscience, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia.

Fax: +6-03-89423087. E-mail: nhlajis@ibs.upm.edu.my

c Department of Bioresources Chemistry, Okayama University, Okayama 700, Japan

d Department of Food and Nutrition, Osaka City University, 3Ð3Ð138, Sugimoto, Sumiyoshi-ku, Osaka, Japan

Present address: Glycobiology Institute, University of Oxford, Oxford OX1 3QU, United Kingdom

* Author for correspondence and reprint requests

Z. Naturforsch.57 c,291Ð295 (2002); received November 5/November 11, 2001 Garcinia atroviridis, Fruits,β-Lactone

Two new garcinia acid derivatives, 2-(butoxycarbonylmethyl)-3-butoxycarbonyl-2-hydroxy- 3-propanolide and 1⬘,1⬙-dibutyl methyl hydroxycitrate, were isolated from the fruits ofGar- cinia atroviridisguided by TLC bioautography against the fungusCladosporium herbarum.

The structures of these compounds were established by spectral analysis. The former com- pound represents a unique β-lactone structure and the latter compound is most likely an artefact of garcinia acid (= hydroxycitric acid). Both compounds showed selective antifungal activity comparable to that of cycloheximide (MID: 0.5µg/spot) only againstC. herbarumat the MIDs of 0.4 and 0.8µg/spot but were inactive against bacteria (Bacillus subtilis,methicil- lin-resistant Staphylococcus aureus, Pseudomonas aeruginosa and Escherichia coli), other fungi (Alternariasp.,Fusarium moniliformeandAspergillus ochraceous) including the yeast Candida albicans.

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a Department of Chemical Science, Faculty of Science, Universiti Tunku Abdul Rahman, 31900 Kampar, Malaysia.. b Center for Agriculture and Food Research,