Sorbicillinoids from the alga-epiphytic fungus Trichoderma reesei Z56-8

A new highly transformed sorbicillinoid derivative, trichoreesin A (1), and four known monomeric sorbicillinoids, sorbicillin (2), 2',3'-dihydrosorbicillin (3), 3-demethylsorbicillin (4), and sohirnone A (5), were discovered from Trichoderma reesei Z56-8, an epiphyte from the marine brown alga Sargassum sp. The structure and relative configuration of 1 were determined by interpretation of UV, IR, NMR, and MS signals, and its absolute configuration was assigned by analysis of ECD data aided by quantum chemical calculations. This is the first survey of metabolites from marine algicolous T. reesei. Compound 1 represents the first bicyclic vertinolide derivative, and it possesses inhibition of several marine phytoplankton species.

Automated summary

A new highly transformed sorbicillinoid derivative, trichoreesin A (1), along with four known monomeric sorbicillinoids, were discovered from an epiphyte of marine brown alga Sargassum sp. The structure and relative configuration of 1 were determined by interpreting various spectroscopic signals, and its absolute configuration was assigned using quantum chemical calculations. This study provides the first survey of metabolites from marine algicolous Trichoderma reesei and highlights the potential inhibition of marine phytoplankton species by compound 1.