6-Methyl-1,2,4-benzenetriol, a new intermediate in penicillic acid biosynthesis in Penicillium cyclopium

  title={6-Methyl-1,2,4-benzenetriol, a new intermediate in penicillic acid biosynthesis in Penicillium cyclopium},
  author={Junichi Sekiguchi and S Katayama and Y. Yamada},
  journal={Applied and Environmental Microbiology},
  pages={1531 - 1535}
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… Expand
Brominated Azaphilones from the Sponge-Associated Fungus Penicillium canescens Strain 4.14.6a.
The fungus Penicillium canescens was isolated from the inner tissue of the Mediterranian sponge Agelas oroides and yielded one new chlorinated diphenyl ether and 13 known compounds, which are the first example of azaphilones with the connection of a benzene moiety and the pyranoquinone core through a methylene group. Expand
The gene PatG involved in the biosynthesis pathway of patulin, a food-borne mycotoxin, encodes a 6-methylsalicylic acid decarboxylase.
Four genes involved in the four first steps of patulin biosynthesis pathway (acetate→gentisyl alcohol) are now identified and bioconversion assays showed that PATG catalyzed the decarboxylation of 6-methylsalicylic acid into m-cresol, the first stable patulin precursor. Expand
Ligerin, an antiproliferative chlorinated sesquiterpenoid from a marine-derived Penicillium strain.
A new chlorinated sesquiterpenoid analogue of fumagillin, ligerin (1), was isolated from a marine-derived strain of Penicillium, belonging to the subgenus Penicillium, along with the known compoundsExpand
Toxins of Microorganisms
Since contamination by two major mycotoxin groups, aflatoxins and trichothecenes, in food and feed is a worldwide problem, studies on their biosynthesis, regulatory mechanism for their production, and inhibitors of their production are described in detail. Expand
Production of Bioactive Compounds Based on Phylogeny in the Genus Penicillium Preserved at NBRC
Penicillium strains preserved at NBRC were compared as to groupings (11 species-clusters) based on phylogeny and the production of bioactive compounds and showed higher rates of positive strains with multi-biological activities. Expand
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Experiments with cell suspensions and cell extracts indicate that orcinol is metabolized by hydroxylation of the benzene ring followed successively by ring cleavage and hydrolyses to give 2 mol of acetate and 1 mol of pyruvate per mol of Orcinol. Expand
Effect of inhibitors of protein synthesis on the formation of phenols derived from acetate and shikimic acid in Aspergillus fumigatus.
Trihydroxytoluene is the principal phenol secreted into the medium by submerged cultures of Aspergillus fumigatus (approximately 100 mg/l medium). Smaller amounts of tetrahydroxytoluene and itsExpand
Isoepoxydon, a new metabolite of the patulin pathway in Penicillium urticae.
A patulin-negative mutant of Penicillium urticae was known to accumulate about 100mg per litre quantities of the 5,6-epoxygentisyl quinone, (-)-phyllostine and another metabolite (UIII) and was found to be a diastereoisomer of the known phytotoxin, (+)-epoxydon, hence its designation as (+)-iso- or epi-epoxYDon. Expand
Patulin biosynthesis: the metabolism of phyllostine and isoepoxydon by cell-free preparations from Pencillium urticae.
Cell-free extracts of Penicillium urticae (NRRL 2159A), and its Pat- mutants, J2, J1, and S11, were found to contain significant NADP-dependent isoepoxydon dehydrogenase activity. This reversibleExpand
Identification of phyllostine as an intermediate of the patulin pathway in Penicillium urticae.
A patulin negative mutant of Penicillium urticae was found to accumulate large quantities of a reactive, photosensitive compound, which was isolated and identified as (-)-phyllostine (5,6-epoxygentisylquinone), which possessed an antibiotic activity against Bacillus subtilis which was approximately 80% of that exhibited by patulin. Expand
Degradation of orcinol by Aspergillus niger.
Aspergillus niger could utilize orcinol (5-methyl-resorcinol or 3,5-dihydroxytoluene) as the sole source of carbon and energy as well as oxidized form, which was also formed in the culture medium during growth of this organism. Expand
Intermediates in the penicillic acid biosynthesis in Penicillium cyclopium.
  • K. Axberg, S. Catenbeck
  • Chemistry, Medicine
  • Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry
  • 1975
Feeding experiments using 14C-labelled precurosrs demonstrate the following sequence of the biological formation of penicillic acid in Penicillium cyclopium: orsellinic acid leads toExpand
Mycotoxins - Their Biosynthesis in Fungi: Patulin and Related Carcinogenic Lactones.
The current status of the patulin biosynthetic pathway is described with special emphasis on recent findings which have altered the late or post-gentisaldehyde portion of the pathway, which is related to the co-occurrence of some of these lactones in cultures of the same fungus. Expand
Conidiogenesis and secondary metabolism in Penicillium urticae
Results indicate that patulin and the other related secondary metabolites noted above are not a prerequisite to conidiogenesis in P. urticae, and environmental and developmental factors such as calcium levels and conidiogenic do, however, indirectly affect the production of patulin pathway metabolites. Expand
Patulin biosynthesis: enzymatic and nonenzymatic transformations of the mycotoxin (E)-ascladiol
A mycotoxin was established as a direct precursor of patulin in cell-free preparations of Penicillium urticae patulin-minus mutants J1 and S11, but not S15, and isomerization to a side product was nonenzymatically catalyzed by sulfhydryl compounds. Expand