Biocatalytic oxidation of 4-vinylphenol by <i>Nocardia</i>

Lee, Kyung-Seon; Rosazza, John P. N.

doi:10.1139/v02-034

Cited by 9 publications

(7 citation statements)

References 23 publications

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“…A soluble form of nitric oxide synthase (NOS NOC ), 13 carboxylic acid reductase, 14 aryl aldehyde oxidoreductase, 15 aldehyde reductase, 16 guanylate cyclase, 17 and ornithine transcarbamoylase 18 have all been characterized in this organism. Activities for Nocardia cyclohydrolase I, sepiapterin reductase, vinylphenol hydratase, 19 hydroxyethylphenol oxidoreductase, 19 and vanillate decarboxylase are all under investigation in our laboratory.…”

Section: Resultsmentioning

confidence: 99%

Oxidation, Reduction, and Methylation of Carnosic Acid by Nocardia

et al. 2002

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Preparative-scale incubations with Nocardia sp. NRRL 5646 were conducted to produce new derivatives of the abietane diterpene chemoprotectant and antioxidant carnosic acid (1). Reductive biotransformation of the C-20 carboxylic acid functional group followed by biological methylation at the C-11 phenol afforded 4. Oxidative cyclization of 1 to carnosol 5 followed by dihydroxylation at the isopropyl moiety afforded 6. Metabolites 4 and 6 are new carnosic acid derivatives whose structures were confirmed by mass spectrometry and NMR spectroscopic analysis. The radical quenching properties of 4-6 using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) free-radical-scavenging assay showed activities similar to that of mixed tocopherols and carnosic acid.

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Section: Resultsmentioning

confidence: 99%

Oxidation, Reduction, and Methylation of Carnosic Acid by Nocardia

et al. 2002

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“…In this study it has been shown that Nocardia is capable of producing 1-(4-hydroxyphenyl)ethanol and 4-hydroxyacetophenone when incubated with 4-vinylphenol. The authors hypothesised that in this conversion a quinone methide intermediate might be involved (Lee & Rosazza, 2002). 07.154,07.164,07.243 and 07.234] No data have been submitted for any of these five candidate flavouring substances.…”

Section: Vinyl-and Alkoxy-substituted Phenolmentioning

confidence: 99%

“…The authors hypothesised that in this conversion a quinone methide intermediate might be involved (Lee & Rosazza, 2002).…”

Section: Phenols With Alkoxy- Alkenyl-or Ketonic Ring Substituentsmentioning

confidence: 99%

Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring‐substituted phenolic substances from chemical groups 21 and 25

Flavourings¹

2011

EFS2

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The Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids of the European Food Safety Authority was requested to evaluate 28 flavouring substances in the Flavouring Group Evaluation 22, Revision 1, using the Procedure in Commission Regulation (EC) No 1565/2000. The substance 3,4-methylenedioxyphenol [FL-no: 04.080] was reported to have a genotoxic potential in vitro, while in vivo studies were not available. Therefore, the Panel concluded that the Procedure could not be applied to this substance until adequate genotoxicity data become available. The remaining 27 substances were evaluated through a stepwise approach (the Procedure) that integrates information on structure-activity relationships, intake from current uses, toxicological threshold of concern, and available data on metabolism and toxicity. The Panel concluded that these 27 candidate substances do not give rise to safety concerns at their levels of dietary intake, estimated on the basis of the MSDI approach. Adequate specifications for the materials of commerce are available for all 27 flavouring substances evaluated through the Procedure.

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“…In this study it has been shown that Nocardia is capable of producing 1-(4-hydroxyphenyl)-ethanol and 4-hydroxyacetophenone when incubated with 4-vinylphenol. The authors hypothesised that in this conversion a quinone methide intermediate might be involved (Lee & Rosazza, 2002).…”

Section: Ester Hydrolysismentioning

confidence: 99%

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 22 (FGE.22): Ring‐substituted phenolic substances from chemical groups 21 and 25 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)

2007

EFS2

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The Scientific Panel on Food Additives, Flavourings, Processing Aids and Materials in Contact with Food is asked to advise the Commission on the implications for human health of chemically defined flavouring substances used in or on foodstuffs in the Member States. In particular, the Scientific Panel is asked to evaluate 23 flavouring substances in the Flavouring Group Evaluation FGE.22, using the procedure as referred to in the Commission Regulation EC No 1565/2000. These 23 flavouring substances belong to chemical groups 21 and 25, Annex I of the Commission Regulation EC No 1565/2000. The present Flavouring Group Evaluation deals with 23 ring-substituted phenolic substances. None of the 23 flavouring substances can exist as geometrical or optical isomers. Twenty of the flavouring substances are classified into structural class I and three are classified into structural class II.

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Biocatalytic oxidation of 4-vinylphenol by Nocardia

Cited by 9 publications

References 23 publications

Oxidation, Reduction, and Methylation of Carnosic Acid by Nocardia

Oxidation, Reduction, and Methylation of Carnosic Acid by Nocardia

Scientific Opinion on Flavouring Group Evaluation 22, Revision 1 (FGE.22Rev1): Ring‐substituted phenolic substances from chemical groups 21 and 25

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 22 (FGE.22): Ring‐substituted phenolic substances from chemical groups 21 and 25 (Commission Regulation (EC) No 1565/2000 of 18 July 2000)

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