Synthesis and antifungal activity of the proposed structure of a volatile compound isolated from the edible mushroom <i>Hypsizygus marmoreus</i>

Abstract

We synthesized the proposed structure of an antifungal compound detected in the culture broth of the edible mushroom Hypsizygus marmoreus. Using the Evans aldol and Abiko-Masamune aldol reactions as the key steps, we synthesized all of the stereoisomers of the compound with high stereoselectivity. The GC retention times and the fragmentation patterns in the mass spectra of the synthesized isomers did not match those of the natural product. Therefore, this result may imply that it is necessary to reisolate the natural product and reconsider its structure. All of the synthesized isomers were found to exhibit antifungal activity against the phytopathogenic fungus Alternaria brassicicola. Due to their simple structures, the obtained isomers could be lead compounds for new pesticides.

Identification of two phthalide derivatives and an oxindole compound isolated from the edible mushroom <i>Pleurotus ostreatus</i> and their inhibitory activities against plant pathogenic microorganisms

“… 12 ) Moreover, volatile compounds detected in edible mushrooms have antimicrobial activities against plant pathogenic bacteria and fungi. 13 , 14 ) Given these studies, mushrooms represent excellent candidates for screening structurally diverse bioactive secondary metabolites that can be used for agricultural applications. Among the overall mushroom taxa recorded worldwide, approximately 20% (∼3,284 species) are considered edible.…”