Sorbicillinol, a key intermediate of bisorbicillinoid biosynthesis in Trichoderma sp. USF-2690.
In the course of our screening program for free radical scavengers from Trichoderma sp. USF-2690, we found an unidentified metabolite (1) that appeared by the method used for HPLC analysis. Metabolite 1 gradually decreased with the production of bisorbicillinoids and was easily missed during the general isolation procedure. The LC-ESI-MS (negative) analysis for 1 gave m/z 247 as the (M-1)- ion peak. The hydrolysis of synthetic 6-O-acetylsorbicillinol (+/- -2) by 0.05 M KOH and acetylation of product 1 in an aqueous solution indicated that the structure of 1 was (6S)-4-(2,4-hexadienoyl)-3,6-dihydroxy-2,6-dimethyl-2,4-cyclohexadien-1-one, designated sorbicillinol, a quinol that has been postulated to be important in bisorbicillinoid biosynthesis.
Abe
N
N
School of Food and Nutritional Sciences, University of Shizuoka, Japan. abe@fns1.u-shizuoka-ken.ac.jp
Sugimoto
O
O
Arakawa
T
T
Tanji
K
K
Hirota
A
A
D015764:Bepridil / Q000031:analogs & derivatives* / Q000737:chemistry; D001713:Biphenyl Compounds; D002851:Chromatography, High Pressure Liquid; D003512:Cyclohexanones / Q000737:chemistry / Q000378:metabolism*; D005285:Fermentation; D016166:Free Radical Scavengers / Q000737:chemistry / Q000378:metabolism; D008401:Gas Chromatography-Mass Spectrometry; D007700:Kinetics; D010851:Picrates; D014242:Trichoderma / Q000378:metabolism*
D001713:Biphenyl Compounds; D003512:Cyclohexanones; D016166:Free Radical Scavengers; D010851:Picrates; C453419:sorbicillinol; D015764:Bepridil; C004931:1,1-diphenyl-2-picrylhydrazyl