The Biosynthesis of Patulin

Tanenbaum, Stuart W.; Bassett, Emmett W.

doi:10.1016/s0021-9258(18)69939-9

Cited by 57 publications

(13 citation statements)

References 20 publications

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“…Other metabolites were eluted with greater concentrations of ether-light petroleum and appeared to be identical with gentisyl alcohol, gentisic acid and patulin. These substances have all been found previously in P. urticae (Birkinshaw, Bracken & Raistrick, 1943;Tanenbaum & Bassett, 1959) and are probably derived from 6-methylsalicylic acid in this organism (Tanenbaum & Bassett, 1959;Gatenbeck & Lonnroth, 1962).…”

Section: 0~~~~csupporting

confidence: 71%

“…It seems likely that 6-methylsalicylic acid is first oxidized and decarboxylated to a gentisic acid-type compound before conversion into the aromatic precursor of ubiquinone in A. fumigatuB. This latter acid (2,5-dihydroxybenzoic acid) is probably derived from 6-methylsalicylic acid in P. urticae (Tanenbaum & Bassett, 1959;Gatenbeck & L6nnroth, 1962).…”

Section: Discussionmentioning

confidence: 99%

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Studies on the biosynthesis of quinones in fungi. Incorporation of 6-methylsalicylic acid into fumigatin and related compounds in Aspergillus fumigatus I.M.I. 89353

Packter

1965

Biochemical Journal

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1. Orsellinic acid has been detected as a metabolite of Aspergillus fumigatus. 2. The other principal aromatic components of the medium are fumigatin and the quinol, fumigatol. Fumigatol has been shown to be dihydrofumigatin after oxidation to the quinone followed by acetylation. 3. (14)C-labelled 6-methylsalicylic acid can be hydroxylated in A. fumigatus to form orsellinic acid and decarboxylated to give m-cresol. 4. (14)C-labelled 6-methylsalicylic acid is incorporated into fumigatin and fumigatol (1.0-1.5%), but the conversion does not occur until about 2-3 days after supplementation of the medium. At this stage of growth, the organism has already synthesized approx. 20 times as much fumigatol as fumigatin and this ratio is reflected in the much lower specific activity of the quinol. 5. Supplementation of the medium with either orsellinic acid or orcinol, in addition to (14)C-labelled 6-methylsalicylic acid, greatly decreases the latter's incorporation into fumigatin. At the same time, the cultures containing these substances are stimulated to produce another quinone with relatively high specific activity. 6. 6-Methylsalicylic acid has not been detected in the medium of normal cultures. The results indicate that 6-methylsalicylic acid itself is not a direct precursor of fumigatin and fumigatol but that it is converted into a true intermediate, probably after hydroxylation to orsellinic acid. 7. Supplementation of the medium with 6-methylsalicylic acid (15-25mg./200ml.) greatly affects the metabolism of A. fumigatus. Growth is inhibited and the synthesis of fumigatol is markedly depressed in these cultures. The inhibitory effects may possibly be related in some way to the production of m-cresol.

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Section: 0~~~~csupporting

confidence: 71%

Section: Discussionmentioning

confidence: 99%

Studies on the biosynthesis of quinones in fungi. Incorporation of 6-methylsalicylic acid into fumigatin and related compounds in Aspergillus fumigatus I.M.I. 89353

Packter

1965

Biochemical Journal

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“…Birkinshaw (1953) postulated an analogous mode of formation of the heterocycic mould product patulin, through oxidative ring fission of gentisic aldehyde. It was subsequently shown that patulin can arise from 6-methylsalicylic acid, both of which occur together with gentisyl alcohol in Penicillium patulum (Bu'Lock & Ryan, 1958;Tanenbaum & Bassett, 1959). Similarly, orsellinic acid (XII) was converted by ring fission into penicillic acid (XIV) (Mosbach, 1960) (see Fig.…”

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confidence: 98%

Studies in the biosynthesis of fungal metabolites. 4. Alternariol monomethyl ether and its relation to other phenolic metabolites of Alternaria tenuis

Thomas¹

1961

Biochemical Journal

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“…In the case of the fungus Penicillium patulum, enzymatic modifications of 6-MSA lead to a family of phenolic substances including gentisaldehyde (XVI) shown here, and patulin (XVII), which under cer- Figure 8. Synthetic processes in polyketide formation illustrated with the 6-methylsalicylic acid family tain conditions can be the major metabolic product (Tanenbaum and Bassett, 1959).…”

Section: Enzymatic Studiesmentioning

confidence: 99%

Enzymic studies on the polyketide hypothesis

Light¹

1970

J. Agric. Food Chem.

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The polyketide hypothesis proposes that many natural products are derived biosynthetically by cyclization of poly-,8-carbonyl (polyketo) acids. Recent versions of this hypothesis propose that the polyketo acid chains can be formed by condensation of one acetyl and several malonyl thiol esters in a manner similar to the condensation reaction of fatty acid biosynthesis. Properties of three crude synthases which support this hypothesis are reviewed: 6-methylsalicylic acid (6-MSA) synthase, alternariol

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The Biosynthesis of Patulin

Cited by 57 publications

References 20 publications

Studies on the biosynthesis of quinones in fungi. Incorporation of 6-methylsalicylic acid into fumigatin and related compounds in Aspergillus fumigatus I.M.I. 89353

Studies on the biosynthesis of quinones in fungi. Incorporation of 6-methylsalicylic acid into fumigatin and related compounds in Aspergillus fumigatus I.M.I. 89353

Studies in the biosynthesis of fungal metabolites. 4. Alternariol monomethyl ether and its relation to other phenolic metabolites of Alternaria tenuis

Enzymic studies on the polyketide hypothesis

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