Secondary Metabolites from Xylaria Endophytes: The isolation and structure elucidation of secondary metabolites from Xylaria endophytes by chemical and spectroscopic methods

Abstract

This thesis describes the isolation and structure elucidation of secondary metabolites from a number of endophytic Xylaria fungi. Six Xylaria endophytes were surface cultured on an aqueous malt extract-glucose medium. The fungus A311R, from a palm tree in Thailand, produced nonane-1,2,3-tricarboxylic acid, which was isolated for the first time as a natural product. Also isolated from the same fungus was spiculisporic acid; the first instance of isolation from a Xylaria fungus. The fungus 6RD12 produced cycloepoxydon, which was isolated for the first time from a Xylaria fungus, and 4,5,6-trihydroxy-3-propyl-3,4,6,7-tetrahydro-l//-isochromen- 8(5//)-one, which is a novel compound. The fungi A217R and A517R produced cytochalasin D, (S)-mellein and (3S,4S)-4-hydroxymellein as main secondary metabolites suggesting that the two fungi are the same species. The fungus X04 (Xylaria cf. juruensis) produced 2-Hydroxy-5-ethoxy-3-methylcyclohexa-2,5-dien- 1,4-dione as a novel compound, coriloxin as the main secondary metabolite in addition to (R)-mellein and a mixture of two stereoisomers of the 4-Hydroxymellein. The fungus 6RD8 produced (S)-Omethylmellein as the main secondary metabolite. l