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Journal of Chemical Ecology, Vol. 23, No. 7, 1997
ANTIFUNGAL XANTHONES FROM Calophyllum
brasiliensis HEARTWOOD 1
RICARDO REYES-CHILPA,*- MANUEL JIMENEZ-ESTRADA ,
and ELIZABETH ESTRADA-MUNIZ
Instituto de Quimica, Universidad National Autonoma de Mexico
Ciudad Universilaria
Coyoacan. 04510 Mexico, DF
(Received October 14, 1996; accepted March 17, 1997)
Abstract—The heartwood of the tropical tree Calophyllum brasiliensis is
known to be highly resistant to fung i and termites . To determine whether
resistance to wood-rotting fung i could be caused by bioactive secondary
metabolites , a chemical and biological study was carried out . Hexane , ace-
tone, methanol , and water extract s were prepared . The yiel d of the extract s
ranged from 0.04% (hexane) to 4.81 % (acetone) . Methanol , acetone, and
water extracts ( 5 mg/m l = 0.5%) inhibite d the mycelia l growth of the brown
rot fungu s Postia placenta by 83% , 59% , and 2 1 % , respectively . Chroma-
tographic separation of the acetone and methanol extract s afforded five
prenylated xanthones : 6-desoxyjacareubin (I) , 1,5-dihydroxy-2-(3,3-dimethyl -
allyl)-3-methoxy-xanthone (II) , jacareubin ( I I I ) an d l,3,5-trihydroxy-2-(3,3 -
dimethylallylj-xanthone (IV
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