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6-Methyl-1,2,4-benzenetriol, a New Intermediate in Penicillic Acid Biosynthesis in Penicillium Cyclopium

J Sekiguchi, S Katayama, Y Yamada

Appl Environ Microbiol. 1987 Jul;53(7):1531-5.

PMID: 3662504

Abstract:

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.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP5980972 2,4,6-Trimethylphenylboronic acid 2,4,6-Trimethylphenylboronic acid 5980-97-2 Price
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