Studies in relation to biosynthesis. VII. 2-Hydroxy-6-methylbenzoic acid in Penicillium griseofulvum Dierckx

Birch, A. J.; Massy-Westropp, RA; Moye, C. J.

doi:10.1071/ch9550539

Cited by 125 publications

(63 citation statements)

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“…3-Methylphenol (Tschinkel 1969;Attygalle et al 1991;Villaverde et al 2007;Geiselhardt et al 2009;), 3-ethylphenol (Tschinkel 1969;Geiselhardt et al 2009), 2-methylhydroquinone (Happ 1968;Wahrendorf and Wink 2006;Villaverde et al 2007;Geiselhardt et al 2009), and 2-ethylhydroquinone (Happ 1968;Hodges et al 1996;Wahrendorf and Wink 2006;Geiselhardt et al 2009) have all been detected in the defensive secretions of other tenebrionid beetles, although quinones are more ubiquitous 3-Methylphenol, 2-methylhydroquinone, and methyl-pbenzoquinone are thought to be sequential members of a biosynthetic pathway that originates with 6-methylsalicylic acid (Gnanasunderam et al 1984), itself formed from acetate (or malonate) units (Birch et al 1955). Similarly, 3-ethylphenol, 2-ethylhydroquinone, and ethyl-p-benzoquinone are likely derived from 6-ethylsalicylic acid (Gnanasunderam et al 1984), which differs in its synthesis by the use of a propionate unit in place of an acetate (or malonate) unit, as evidenced by isotope tracing experiments on ethyl-pbenzoquinone (Meinwald et al 1966).…”

Section: Discussionmentioning

confidence: 99%

Differences in Defensive Volatiles of the Forked Fungus Beetle, Bolitotherus cornutus, Living on Two Species of Fungus

et al. 2009

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Forked fungus beetles, Bolitotherus cornutus, feed, mate, and live on the brackets of several species of shelf fungus that grow on decaying logs. In response to the specific threat stimulus of mammalian breath, B. cornutus beetles produce a volatile defensive secretion. We tested beetles collected from different host fungi to determine whether defensive secretion blends varied with host type. Using solid phase microextraction and gas chromatographymass spectrometry, we detected large amounts of the alkylated benzoquinones, methyl-p-benzoquinone (toluquinone) and ethyl-p-benzoquinone, and smaller quantities of p-benzoquinone, 3-methylphenol (m-cresol), 3-ethylphenol, 2-methylhydroquinone, and 2-ethylhydroquinone in secretions. Volatile composition did not differ between male and female beetles. Secretions did differ between beetles collected from two species of fungus, Ganoderma applanatum and Fomes fomentarius, with the relative amount of pbenzoquinone secreted being the most important factor. Other relationships among the volatile components are discussed.

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Section: Discussionmentioning

confidence: 99%

Differences in Defensive Volatiles of the Forked Fungus Beetle, Bolitotherus cornutus, Living on Two Species of Fungus

et al. 2009

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“…[9] Little is known about the biosynthesis of these phytotoxic compounds (Scheme 1), except that they are derived from seven units of acetyl CoA like other salicylaldehyde-type congeners. [10,11] tatrienylsalicyl alcohol (7) is an important biosynthetic intermediate of salicylaldehyde-type polyketide synthesis, [8,12] because the fungus could oxidize (Z)-and (E)-1-phenylpropenes to racemic erythro-diol and optically active threo-diol, respectively. [13] We also assumed that heptatrienylsalicylaldehyde (8) could be an intermediate, because Iwasaki et al reported that aldehyde 2 was converted to alcohol 1 by the fungus.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Biotransformation of Plausible Biosynthetic Intermediates of Salicylaldehyde‐Type Phytotoxins of Rice Blast Fungus, Magnaporthe grisea

et al. 2011

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Rice blast fungus, Magnaporthe grisea, produces a series of salicylaldehyde‐type phytotoxins such as pyriculol, pyricuol, and pyriculariol. Plausible biosynthetic intermediates of these phytotoxins were synthesized in deuterium labeled forms using the Stille coupling reaction as the key step, and subjected to biotransformation by the fungus. Heptatrienylsalicylaldehyde was converted into dihydropyriculol by the fungus by a shaking culture. A new biosynthetic pathway comprising both oxidation and reduction is proposed.

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“…Diese Erkenntnisse haben Birch zur Aufstellung der ,,Polyacetat-Regel" veranlal3t [I], die sich bei Strukturermittlungen auf dem Naturstoffgebiet als ungemein fruchtbar erwiesen hat und deren Giiltigkeit durch die klassischen Isotopenexperimente von Birch [2] und Ehrensviird [3] erstmals bewiesen wurde. Man nahm zunachst an, daJ3 die als Zwischenprodukte vermuteten Polyketomethylen-Strukturen durch Kondensation mehrerer Molekule Acetyl-CoA entstehen.…”

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Biosynthese von 6‐Methylsalicylsäure

Dimroth

Walter

Lynen

1970

European Journal of Biochemistry

193

124

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An extract was prepared from Penicillium ptulum grown in submerged culture, which converted acetyl-CoA and malonyl-CoA into 6-methylsalicylic acid in the presence of NADPH. The enzyme wa.s very labile in the crude extract, but appeared stable after acetone precipitation. A 100-fold purification was achieved by ammonium sulfate fractionation, sedimentation in the ultracentrifuge, and sucrose-density gradient centrifugation. The enzyme was a single particle with a molecular weight of 1.1 -1.5 x lo6 as determined by gradient centrifugation with catalase and fatty acid synthetase as standards. I n the first steps of purification, fatty acid synthetase from Penicillium patulum migrated with the methylsalicylic acid synthetase complex. A separation of the two enzyme systems was accomplished by sucrose-density gradient centrifugation. The purified enzyme represents a new multienzyme complex which shares several common properties with fatty acid synthetase. Methylsalicylic acid synthetase is inhibited by iodoacetamide and N-ethylmaleinimide. The incubation of enzyme with acetyl-CoA and malonyl-CoA in the absence of NADPH led to triacetic acid lacton. This indicates that in 6-methylsalicylic acid synthesis reduction occurs a t the triacetic acid level before the final condensation with malonylCoA. Triacetic acid lacton was produced by the enzyme a t loo/, of the rate of 6-methylsalicylic acid synthesis in the complete system. This rate of lacton synthesis, however, is an order of magnitude greater than that catalysed by fatty acid synthetase. A possible explanation for this difference in behavior is given. Covalent linkage of substrates and intermediates to SH-groups of the protein during the synthesis of 6-methylsalicyslic acid is suggested. A reaction scheme leading to 6-methylsalicylic acid is proposed and the partial reactions of this synthesis are dkcussed with respect to similar reactions of fatty acid biosynthesis.Beim Vergleich der chemischen Strukturen natiirlich vorkommender Kohlenstoffverbindungen hat man erkannt, daJ3 die Synthese zahlreicher Naturstoffe uber Polyketomethylen-Verbindungen erfolgen konnte, die durch Kondensation mehrerer Essigsauremolekiile ,,Kopf an Xchwanz" gebildet werden. Diese Erkenntnisse haben Birch zur Aufstellung der ,,

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Studies in relation to biosynthesis. VII. 2-Hydroxy-6-methylbenzoic acid in Penicillium griseofulvum Dierckx

Cited by 125 publications

References 0 publications

Differences in Defensive Volatiles of the Forked Fungus Beetle, Bolitotherus cornutus, Living on Two Species of Fungus

Differences in Defensive Volatiles of the Forked Fungus Beetle, Bolitotherus cornutus, Living on Two Species of Fungus

Synthesis and Biotransformation of Plausible Biosynthetic Intermediates of Salicylaldehyde‐Type Phytotoxins of Rice Blast Fungus, Magnaporthe grisea

Biosynthese von 6‐Methylsalicylsäure

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