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First 2-hydroxy-3-methylbut-3-enyl substituted xanthones isolated from plants: structure elucidation, synthesis and
Jean-Michel Oger1, Cécile Morel, Jean-Jacques Helesbeux
1SONAS, UFR des Sciences Pharmaceutiques et Ingénierie de la Santé, 16 Bd Daviers, F-49100 Angers, France. jean-michel.oger@univ-angers.fr
Abstract:
Two new 2-hydroxy-3-methylbut-3-enyl substituted xanthones, (+/-)-caledol 1 and (+/-)-dicaledol 2 were isolated from a dichloromethane extract of the leaves of Calophyllum caledonicum (Clusiaceae). Compounds 1 and 2 are the first 2-hydroxy-3-methylbut-3-enyl substituted xanthones isolated from natural source. Their structures were elucidated by means of combined analytical methods including HRFABMS, 1D and 2D NMR spectroscopies and also confirmed by total synthesis using biomimetic ortho-prenylphenols photooxygenation (1O2) as a key step. The antifungal activity against Aspergillus fumigatus is reported.