Decarboxylation of Substituted Cinnamic Acids by Lactic Acid Bacteria Isolated during Malt Whisky Fermentation

Beek, Sylvie van; Priest, Fergus G.

doi:10.1128/aem.66.12.5322-5328.2000

Cited by 131 publications

(98 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Goodey and Tubb (12) examined the generation of phenolic off-flavors by yeasts in beer and demonstrated ferulic acid decarboxylation to 4-vinylguaiacol mediated by the PAD1 gene (then named the POF1 gene) with lesser action on coumaric and cinnamic acids. However, the decarboxylation of ferulic and coumaric acids by S. cerevisiae in laboratory cultures has been reported by other authors (7,13,48) to be slow and with low activity, a suggestion that we confirm with a lack of activity detected by Pad1p on coumaric acid over 10 h.…”

Section: Discussionsupporting

confidence: 78%

“…The phenolic acid decarboxylase gene from B. subtilis was overexpressed in S. cerevisiae (38), and the recombinant strain had high activity against coumaric acid. Lactobacillus plantarum has also been shown to contain decarboxylases with specificity towards coumaric acid and ferulic acid (2,5,6,38,48). No aliphatic acids such as sorbic acid appear to have been tested on any bacterial phenolic acid decarboxylases.…”

Section: Discussionmentioning

confidence: 99%

See 1 more Smart Citation

Decarboxylation of Sorbic Acid by Spoilage Yeasts Is Associated with the PAD1 Gene

Stratford

Plumridge

Archer

2007

Appl Environ Microbiol

View full text Add to dashboard Cite

The spoilage yeast Saccharomyces cerevisiae degraded the food preservative sorbic acid (2,4-hexadienoic acid) to a volatile hydrocarbon, identified by gas chromatography mass spectrometry as 1,3-pentadiene. The gene responsible was identified as PAD1, previously associated with the decarboxylation of the aromatic carboxylic acids cinnamic acid, ferulic acid, and coumaric acid to styrene, 4-vinylguaiacol, and 4-vinylphenol, respectively. The loss of PAD1 resulted in the simultaneous loss of decarboxylation activity against both sorbic and cinnamic acids. Pad1p is therefore an unusual decarboxylase capable of accepting both aromatic and aliphatic carboxylic acids as substrates. All members of the Saccharomyces genus (sensu stricto) were found to decarboxylate both sorbic and cinnamic acids. PAD1 homologues and decarboxylation activity were found also in Candida albicans, Candida dubliniensis, Debaryomyces hansenii, and Pichia anomala. The decarboxylation of sorbic acid was assessed as a possible mechanism of resistance in spoilage yeasts. The decarboxylation of either sorbic or cinnamic acid was not detected for Zygosaccharomyces, Kazachstania (Saccharomyces sensu lato), Zygotorulaspora, or Torulaspora, the genera containing the most notorious spoilage yeasts. Scatter plots showed no correlation between the extent of sorbic acid decarboxylation and resistance to sorbic acid in spoilage yeasts. Inhibitory concentrations of sorbic acid were almost identical for S. cerevisiae wild-type and ⌬pad1 strains. We concluded that Pad1p-mediated sorbic acid decarboxylation did not constitute a significant mechanism of resistance to weak-acid preservatives by spoilage yeasts, even if the decarboxylation contributed to spoilage through the generation of unpleasant odors.

show abstract

Section: Discussionsupporting

confidence: 78%

Section: Discussionmentioning

confidence: 99%

Decarboxylation of Sorbic Acid by Spoilage Yeasts Is Associated with the PAD1 Gene

Stratford

Plumridge

Archer

2007

Appl Environ Microbiol

View full text Add to dashboard Cite

show abstract

“…In TIM 1, 41.0% Ϯ 5.8% (n ϭ 3) of the ingested trans-cinnamic acid was converted into p-coumaric acid after 240 min of digestion. In TIM 2, the CA4H activity was detected until 4 h after the introduction of the yeasts but could not be quantified, owing to the degradation of both the substrate and the product by colonic microflora (26). A more suitable bioconversion model is consequently being studied for the colon.…”

Section: Discussionmentioning

confidence: 99%

RecombinantSaccharomyces cerevisiaeExpressing P450 in Artificial Digestive Systems: a Model for Biodetoxication in the Human Digestive Environment

Blanquet

Meunier

Minekus

et al. 2003

Appl Environ Microbiol

View full text Add to dashboard Cite

The use of genetically engineered microorganisms such as bacteria or yeasts as live vehicles to carry out bioconversion directly in the digestive environment is an important challenge for the development of innovative biodrugs. A system that mimics the human gastrointestinal tract was combined with a computer simulation to evaluate the survival rate and cinnamate 4-hydroxylase activity of a recombinant model of Saccharomyces cerevisiae expressing the plant P450 73A1. The yeasts showed a high level of resistance to gastric and small intestinal secretions (survival rate after 4 h of digestion, 95.6% ؎ 10.1% [n ‫؍‬ 4]) but were more sensitive to the colonic conditions (survival rate after 4 h of incubation, 35.9% ؎ 2.7% [n ‫؍‬ 3]). For the first time, the ability of recombinant S. cerevisiae to carry out a bioconversion reaction has been demonstrated throughout the gastrointestinal tract. In the gastric-small intestinal system, 41.0% ؎ 5.8% (n ‫؍‬ 3) of the ingested transcinnamic acid was converted into p-coumaric acid after 4 h of digestion, as well as 8.9% ؎ 1.6% (n ‫؍‬ 3) in the stomach, 13.8% ؎ 3.3% (n ‫؍‬ 3) in the duodenum, 11.8% ؎ 3.4% (n ‫؍‬ 3) in the jejunum, and 6.5% ؎ 1.0% (n ‫؍‬ 3) in the ileum. In the large intestinal system, cinnamate 4-hydroxylase activity was detected but was too weak to be quantified. These results suggest that S. cerevisiae may afford a useful host for the development of biodrugs and may provide an innovative system for the prevention or treatment of diseases that escape classical drug action. In particular, yeasts may provide a suitable vector for biodetoxication in the digestive environment.

show abstract

“…Moreover, p-ethylphenol can also be plant derived; e.g., native olive oils contain up to 52 mg p-ethylphenol per kg, and the content can reach 470 mg kg Ϫ1 during storage (5). p-Ethylphenol can also be formed from p-coumaric acid, a major component of cereal cell walls, by several yeast and Lactobacillus species (11,50). Due to their cytotoxicity and relatively high water solubility (www.epa.gov/safewater/mcl .html), alkylphenols are of environmental concern.…”

mentioning

confidence: 99%

Anaerobic Degradation of p -Ethylphenol by “ Aromatoleum aromaticum ” Strain EbN1: Pathway, Regulation, and Involved Proteins

Wöhlbrand

Wilkes

Halder³

et al. 2008

J Bacteriol

View full text Add to dashboard Cite

The denitrifying "Aromatoleum aromaticum" strain EbN1 was demonstrated to utilize p-ethylphenol under anoxic conditions and was suggested to employ a degradation pathway which is reminiscent of known anaerobic ethylbenzene degradation in the same bacterium: initial hydroxylation of p-ethylphenol to 1-(4-hydroxyphenyl)-ethanol followed by dehydrogenation to p-hydroxyacetophenone. Possibly, subsequent carboxylation and thiolytic cleavage yield p-hydroxybenzoyl-coenzyme A (CoA), which is channeled into the central benzoyl-CoA pathway. Substrate-specific formation of three of the four proposed intermediates was confirmed by gas chromatographic-mass spectrometric analysis and also by applying deuterated p-ethylphenol. Proteins suggested to be involved in this degradation pathway are encoded in a single large operon-like structure (ϳ15 kb). Among them are a p-cresol methylhydroxylase-like protein (PchCF), two predicted alcohol dehydrogenases (ChnA and EbA309), a biotin-dependent carboxylase (XccABC), and a thiolase (TioL). Proteomic analysis (two-dimensional difference gel electrophoresis) revealed their specific and coordinated upregulation in cells adapted to anaerobic growth with p-ethylphenol and p-hydroxyacetophenone (e.g., PchF up to 29-fold). Coregulated proteins of currently unknown function (e.g., EbA329) are possibly involved in p-ethylphenol-and p-hydroxyacetophenone-specific solvent stress responses and related to other aromatic solvent-induced proteins of strain EbN1.Alkylphenols, such as p-ethylphenol, are present in coal tars and crude oils (2, 45). Besides the accidental release of fuelderived alkylphenols to the environment, phenolic compounds are also prominent constituents of petrochemical wastewaters arising from spent caustic and coal gasification. Alkylphenol concentrations in these effluents (mainly phenol, cresols, and ethylphenols) range from 100 to 68,000 mg liter Ϫ1 , depending on the source (2). Moreover, p-ethylphenol can also be plant derived; e.g., native olive oils contain up to 52 mg p-ethylphenol per kg, and the content can reach 470 mg kg Ϫ1 during storage (5). p-Ethylphenol can also be formed from p-coumaric acid, a major component of cereal cell walls, by several yeast and Lactobacillus species (11,50). Due to their cytotoxicity and relatively high water solubility (www.epa.gov/safewater/mcl .html), alkylphenols are of environmental concern.Anaerobic degradation of aromatic compounds requires reactions independent of molecular oxygen. They are fundamentally different from the oxygenase-catalyzed reactions employed under oxic conditions (for an overview, see references 14, 17, and 18). A variety of anaerobic aromatic compounddegrading bacteria were newly isolated during the last decades (for an overview, see references 46 and 51). Most of them are denitrifiers belonging to the "Aromatoleum"/Azoarcus/Thauera cluster within Betaproteobacteria (R. Rabus et al., unpublished data). "Aromatoleum aromaticum" strain EbN1, a metabolically versatile representative of this group, was originall...

show abstract

Decarboxylation of Substituted Cinnamic Acids by Lactic Acid Bacteria Isolated during Malt Whisky Fermentation

Cited by 131 publications

References 17 publications

Decarboxylation of Sorbic Acid by Spoilage Yeasts Is Associated with the PAD1 Gene

Decarboxylation of Sorbic Acid by Spoilage Yeasts Is Associated with the PAD1 Gene

RecombinantSaccharomyces cerevisiaeExpressing P450 in Artificial Digestive Systems: a Model for Biodetoxication in the Human Digestive Environment

Anaerobic Degradation of p -Ethylphenol by “ Aromatoleum aromaticum ” Strain EbN1: Pathway, Regulation, and Involved Proteins

Contact Info

Product

Resources

About