6-Methyl-1,2,4-benzenetriol, a new intermediate in penicillic acid biosynthesis in Penicillium cyclopium.
Penicillic acid-negative mutants were obtained from a color mutant derived from Penicillium cyclopium NRRL 1888 through N-methyl-N'-nitro-N-nitrosoguanidine treatment. One mutant (SK2N6) accumulated 6-methyl-1,2,4-benzenetriol, which was not previously known to be a metabolite of P. cyclopium, in addition to orsellinic acid and orcinol. The radioactivity of [1-14C]acetic acid was rapidly incorporated into 6-methyl-1,2,4-benzenetriol in a culture of P. cyclopium SK2N6. Moreover, the radioactivity of [14C]6-methyl-1,2,4-benzenetriol was efficiently incorporated into penicillic acid in a culture of P. cyclopium NRRL 1888. These data indicate that 6-methyl-1,2,4-benzenetriol is a precursor for penicillic acid biosynthesis. The results on the addition of 1,4-dihydroxy-6-methoxy-2-methylbenzene, 6-methoxy-2-methylbenzoquinone(1,4), and 1-O-methylorcinol to a culture of P. cyclopium SK2N6 indicated that only the former two compounds are converted to penicillic acid. Thus, a new portion of the penicillic acid biosynthetic pathway is proposed.
Sekiguchi
J
J
Department of Applied Biology, Faculty of Textile Science and Technology, Shinshu University, Nagano, Japan.
Katayama
S
S
Yamada
Y
Y
D002208:Caproates / Q000096:biosynthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D006873:Hydroquinones; D009682:Magnetic Resonance Spectroscopy; D009154:Mutation; D010398:Penicillic Acid / Q000096:biosynthesis*; D010407:Penicillium / Q000235:genetics / Q000378:metabolism*; D014050:Toluene / Q000031:analogs & derivatives* / Q000378:metabolism
D002208:Caproates; D006873:Hydroquinones; D014050:Toluene; C053700:6-methyl-1,2,4-benzenetriol; D010398:Penicillic Acid