In the course of our screening to find 1, 1-diphenyl-2-picrylhydrazyl (DPPH) radical scavengers, we isolated eleven sorbicillin-related compounds, including seven novel compounds, from the fermentation broth of
Trichoderma sp. USF-2690. The “bisorbicillinoids” was recently defined by Nicolaou as the term used to designate a group composed of dimeric sorbicillin-related natural products, on which their diverse structures and interesting biological activities were reported by several groups. A few research groups had described biogenesis of bisorbicillinoids, and consequently some distinguishable biosynthetic routes had been presented. Herein we report (1) finding of a functional quinol, sorbicillinol (12), postulated as a key compound in bisorbicillinoids biosynthesis for a long time, (2) evidence for the biosynthetic pathway,
via sorbicillinol (12), of sorbicillin (11), bisorbicillinol (1), bisorbibetanone (9), bisorbicillinolide (3), and bisvertinolone (8), and (3) study on a radical scavenging mechanism of bisorbicillinol (1).
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