Biosynthesis of bisorbicillinoid in Trichoderma sp. USF-2690; evidence for the biosynthetic pathway, via sorbicillinol, of sorbicillin, bisorbicillinol, bisorbibutenolide, and bisorbicillinolide.
An incorporation study of [1-(13)C] and [1,2-(13)C2] labeled sodium acetates into sorbicillinol 1 established a ring closure system between C-1 and C-6 and the positions that were oxidized and/or methylated on a hexaketide chain. Subsequent investigations, using 13C-labeled 1 prepared from [1-(13)C] labeled sodium acetate, clearly demonstrated that both bisorbicillinol 2 and sorbicillin 6 incorporated 13C-labeled 1 into their carbon skeletons. 13C-labeled bisorbicillinols 2 derived from [1-(13)C]- and [2-(13)C]-labeled sodium acetates clearly indicate that these were on the biosynthetic route from 1 to bisorbibutenolide (bislongiquinolide) 3 and bisorbicillinolide 4 via 2 as a branching point in the fungus.
Abe
Naoki
N
School of Food and Nutritional Sciences, University of Shizuoka, 52-1 Yada, Shizuoka 422-8526, Japan. abe@nodai.ac.jp
Arakawa
Tadaharu
T
Yamamoto
Kazunobu
K
Hirota
Akira
A
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000096:biosynthesis / Q000737:chemistry*; D000107:Acetylation; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D001952:Bridged-Ring Compounds / Q000737:chemistry* / Q000378:metabolism; D003512:Cyclohexanones / Q000737:chemistry; D005285:Fermentation; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D012118:Resorcinols / Q000737:chemistry* / Q000378:metabolism; D014242:Trichoderma / Q000378:metabolism*
D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D003512:Cyclohexanones; D012118:Resorcinols; C473618:bisorbibutenolide; C473617:bisorbicillinol; C473619:bisorbicillinolide; C453419:sorbicillinol; C473616:sorbicillin; D015107:4-Butyrolactone