P-65 Trichoderma sp. USF-2690株の産生する生理活性物質sorbicillinoid類の生合成研究(ポスター発表の部)

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The "sorbicillinoids" and "bisorbicillinoids", defined as the term used to designate groups composed of monomeric and dimeric sorbicillin-related natural products, have been attractive in their diverse frameworks and interesting biological activities. In the course of our screening program for antioxidants from microorganisms, we isolated 12 sorbicillinoids and bisorbicillinoids from the fermentation broth of a Trichoderma sp. USF-2690 strain. In our previous study, we established that a functional quinol, sorbicillinol (2), was an important starting point for bisorbicillinoids biosynthesis. However, the biosynthetic mechanism of sorbicillinoids formed via the polyketides pathway and the biosynthetic relationship among sorbicillinoids had been remained obscure. Our experiments for incorporation of [1-^<13>C]-labeled sodium acetate ([1-^<13>C]-SA) gave [1-^<13>C]SA-sorbicillin ([1-^<13>C]-SA-1), [1-^<13>C]-SA-2, [1-^<13>C]-SA-oxosorbicillinol ([1-^<13>C]-SA-3), and [1-^<13>C]-SA-bisvertinolone ([1-^<13>C]-SA-4). Each [1-^<13>C]-SA labeled compound was utilized as a precursor for production of sorbicillinoids (1, 2, and 3) and a bisorbicillinoid (4). The results of incorporation study of partially labeled sorbicillinoids satisfied the proof that one-way biosynthetic routes from 2 to 1 and from 2 to 3 existed. Further investigation making use of HPLC analysis with DAD gave a new sorbicillinoids member 5-epihydroxyvertinolide (5), a postulated end product from the biogenesis. The incorporation patterns of [1-^<13>C]- and [1,2-^<13>C2]-SA demonstrated a biosynthetic route for 5 involving a breakage reaction of carbon-carbon bond. The observation hit on a renewed idea for the sorbicillinoid biosynthesis via an "intermediate B".
天然有機化合物討論会の論文
2007-08-24

P-65 Trichoderma sp. USF-2690株の産生する生理活性物質sorbicillinoid類の生合成研究(ポスター発表の部)

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