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

2000 ◽  
Vol 66 (12) ◽  
pp. 5322-5328 ◽  
Author(s):  
Sylvie van Beek ◽  
Fergus G. Priest
Keyword(s):  
Ferulic Acid ◽  
Lactobacillus Brevis ◽  
Hydroxycinnamic Acid ◽  
Final Concentration ◽  
Acid Decarboxylase ◽  
Yeast Fermentation ◽  
Coumaric Acid ◽  
Cinnamic Acids ◽  
Pure Cultures ◽  
Malt Whisky

ABSTRACT Seven strains of Lactobacillus isolated from malt whisky fermentations and representing Lactobacillus brevis,L. crispatus, L. fermentum, L. hilgardii, L. paracasei, L. pentosus, andL. plantarum contained genes for hydroxycinnamic acid (p-coumaric acid) decarboxylase. With the exception ofL. hilgardii, these bacteria decarboxylatedp-coumaric acid and/or ferulic acid, with the production of 4-vinylphenol and/or 4-vinylguaiacol, respectively, although the relative activities on the two substrates varied between strains. The addition of p-coumaric acid or ferulic acid to cultures ofL. pentosus in MRS broth induced hydroxycinnamic acid decarboxylase mRNA within 5 min, and the gene was also induced by the indigenous components of malt wort. In a simulated distillery fermentation, a mixed culture of L. crispatus and L. pentosus in the presence of Saccharomyces cerevisiae decarboxylated added p-coumaric acid more rapidly than the yeast alone but had little activity on added ferulic acid. Moreover, we were able to demonstrate the induction of hydroxycinnamic acid decarboxylase mRNA under these conditions. However, in fermentations with no additional hydroxycinnamic acid, the bacteria lowered the final concentration of 4-vinylphenol in the fermented wort compared to the level seen in a pure-yeast fermentation. It seems likely that the combined activities of bacteria and yeast decarboxylate p-coumaric acid and then reduce 4-vinylphenol to 4-ethylphenol more effectively than either microorganism alone in pure cultures. Although we have shown that lactobacilli participate in the metabolism of phenolic compounds during malt whisky fermentations, the net result is a reduction in the concentrations of 4-vinylphenol and 4-vinylguaiacol prior to distillation.

Elaboration of the 6,7,8 Oxygenation Pattern in Simple Coumarins: Biosynthesis of Puberulin in Agathosma puberula Fourc

1984 ◽  
Vol 39 (1-2) ◽  
pp. 31-37 ◽  
Author(s):  
Stewart A. Brown ◽  
D. E. A. Rivett ◽  
H. Joan Thompson
Keyword(s):  
Ferulic Acid ◽  
Hydroxycinnamic Acid ◽  
Coumaric Acid ◽  
Major Pathway

Abstract Umbelliferone and scopoletin are well utilized as precursors of puberulin, a 7-O-prenyl ether of isofraxidin elaborated by Agathosm a puberula Fourc. (Rutaceae). As ferulic, sinapic, and caffeic acids were all more poorly utilized than 4′-hydroxycinnamic (p-coumaric) acid, the partial biosynthetic route: 4′-hydroxycinnamic acid →→ um belliferone → aesculetin → scopoletin →→ puberulin is suggested as the major pathway. Prenylether formation apparently occurs at or beyond the scopoletin stage. The implication that ferulic acid does not participate in the formation of scopoletin from 4′-hydroxycinnamic acid is at variance with the known role of ferulic acid as a scopoletin precursor in tobacco.

STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: XI. REACTIONS RELATING TO LIGNIFICATION IN YOUNG WHEAT PLANTS

1963 ◽  
Vol 41 (1) ◽  
pp. 65-76 ◽  
Author(s):  
Takayoshi Higuchi ◽  
Stewart A. Brown
Keyword(s):  
Cell Wall ◽  
Ferulic Acid ◽  
Sinapic Acid ◽  
Cumulative Effect ◽  
Lignin Biosynthesis ◽  
Hydroxycinnamic Acid ◽  
Cinnamic Acids ◽  
Labelled Compound ◽  
The Difference ◽  
Ferulic Acids

L-Phenylalanine-G-C14, p-hydroxycinnamic acid-2-C14, ferulic acid-2-C14, and sinapic acid-2-C14 were administered to wheat plants aged both 30 and 73 days. Radioactive vanilloyl- and syringoyl-methyl ketones were then recovered after ethanolysis of the cell wall residues. When corrected for differences in endogenous lignin, the C14 dilution values calculated for the younger plants were generally greater, indicating, as expected, a slower rate of lignification. The difference between the younger and older plants was less for sinapic and ferulic acids than for p-hydroxycinnamic acid or phenylalanine. This suggested that slower lignification in young plants may be due not to relative inactivity of an enzyme system at any one stage of the biosynthetic pathway but to the cumulative effect of slower reactions at several stages. Sinapic acid is converted in the younger plants to lignin yielding vanilloyl-, as well as syringoyl-, methyl ketone, suggesting a demethoxylation. Glucose esters of the radioactive phenolic cinnamic acids corresponding to the labelled compound administered were recovered from the plant extracts. A small percentage of the activity in the cell wall residue was in the form of ferulic acid joined by ester linkages.

scholarly journals Monitoring Hydroxycinnamic Acid Decarboxylation by Lactic Acid Bacteria Using High-Throughput UV-Vis Spectroscopy

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3142 ◽  
Author(s):  
Gonzalo Miyagusuku-Cruzado ◽  
Israel García-Cano ◽  
Diana Rocha-Mendoza ◽  
Rafael Jiménez-Flores ◽  
M. Monica Giusti
Keyword(s):  
Lactic Acid ◽  
Lactic Acid Bacteria ◽  
Caffeic Acid ◽  
High Throughput ◽  
Hydroxycinnamic Acid ◽  
Acid Decarboxylase ◽  
State University ◽  
Coumaric Acid ◽  
Vis Spectroscopy ◽  
The Ohio State University

Hydroxycinnamic acid (HCA) decarboxylation by lactic acid bacteria (LAB) results in the production of 4-vinylplenols with great impact on the sensorial characteristics of foods. The determination of LAB decarboxylating capabilities is key for optimal strain selection for food production. The activity of LAB strains from the Ohio State University—Parker Endowed Chair (OSU-PECh) collection potentially capable of synthesizing phenolic acid decarboxylase was evaluated after incubation with HCAs for 36 h at 32 °C. A high-throughput method for monitoring HCAs decarboxylation was developed based on hypsochromic shifts at pH 1.0. Out of 22 strains evaluated, only Enterococcus mundtii, Lactobacillus plantarum and Pediococcus pentosaceus were capable of decarboxylating all p-coumaric, caffeic and ferulic acids. Other strains only decarboxylated p-coumaric and caffeic acid (6), only p-coumaric acid (2) or only caffeic acid (1), while 10 strains did not decarboxylate any HCA. p-Coumaric acid had the highest conversion efficiency, followed by caffeic acid and lastly ferulic acid. Results were confirmed by HPLC-DAD-ESI-MS analyses, showing the conversion of HCAs into their 4-vinylphenol derivatives. This work can help improve the sensory characteristics of HCA-rich foods where fermentation with LAB was used during processing.

STUDIES OF LIGNIN BIOSYNTHESIS USING ISOTOPIC CARBON: XI. REACTIONS RELATING TO LIGNIFICATION IN YOUNG WHEAT PLANTS

1963 ◽  
Vol 41 (1) ◽  
pp. 65-76 ◽  
Author(s):  
Takayoshi Higuchi ◽  
Stewart A. Brown
Keyword(s):  
Cell Wall ◽  
Ferulic Acid ◽  
Sinapic Acid ◽  
Cumulative Effect ◽  
Lignin Biosynthesis ◽  
Hydroxycinnamic Acid ◽  
Cinnamic Acids ◽  
Labelled Compound ◽  
The Difference ◽  
Ferulic Acids

L-Phenylalanine-G-C14, p-hydroxycinnamic acid-2-C14, ferulic acid-2-C14, and sinapic acid-2-C14 were administered to wheat plants aged both 30 and 73 days. Radioactive vanilloyl- and syringoyl-methyl ketones were then recovered after ethanolysis of the cell wall residues. When corrected for differences in endogenous lignin, the C14 dilution values calculated for the younger plants were generally greater, indicating, as expected, a slower rate of lignification. The difference between the younger and older plants was less for sinapic and ferulic acids than for p-hydroxycinnamic acid or phenylalanine. This suggested that slower lignification in young plants may be due not to relative inactivity of an enzyme system at any one stage of the biosynthetic pathway but to the cumulative effect of slower reactions at several stages. Sinapic acid is converted in the younger plants to lignin yielding vanilloyl-, as well as syringoyl-, methyl ketone, suggesting a demethoxylation. Glucose esters of the radioactive phenolic cinnamic acids corresponding to the labelled compound administered were recovered from the plant extracts. A small percentage of the activity in the cell wall residue was in the form of ferulic acid joined by ester linkages.

scholarly journals Improving the catalytic characteristics of phenolic acid decarboxylase from Bacillus amyloliquefaciens by the engineering of N-terminus and C-terminus

2021 ◽  
Vol 21 (1) ◽  
Author(s):  
Qin Li ◽  
Ying Xia ◽  
Ting Zhao ◽  
Yuanyuan Gong ◽  
Shangling Fang ◽  
...  
Keyword(s):  
Ferulic Acid ◽  
Phenolic Acid ◽  
Bacillus Amyloliquefaciens ◽  
Sinapic Acid ◽  
Alkali Resistance ◽  
Acid Decarboxylase ◽  
Coumaric Acid ◽  
C Terminus ◽  
N Terminus ◽  
Phenolic Acid Decarboxylase

Abstract Background 4-vinylphenols produced by phenolic acid degradation catalyzed by phenolic acid decarboxylase can be used in food additives as well as flavor and fragrance industry. Improving the catalytic characters of phenolic acid decarboxylase is of great significance to enhance its practical application. Results A phenolic acid decarboxylase (P-WT) was created from Bacillus amyloliquefaciens ZJH-01. Mutants such as P-C, P-N, P-m1, P-m2, P-Nm1, and P-Nm2 were constructed by site-directed mutagenesis of P-WT. P-C showed better substrate affinities and higher turnover rates than P-WT for p-coumaric acid, ferulic acid, and sinapic acid; however, P-N had reduced affinity toward p-coumaric acid. The extension of the C-terminus increased its acid resistance, whereas the extension of the N-terminus contributed to the alkali resistance and heat resistance. The affinity of P-m1 to four substrates and that of P-m2 to p-coumaric acid and ferulic acid were greatly improved. However, the affinity of P-Nm2 to four phenolic acids was greatly reduced. The residual enzyme activities of P-Nm1 and P-Nm2 considerably improved compared with those of P-m1 and P-m2 after incubation at 50 °C for 60 min. Conclusions The extension of the N-terminus may be more conducive to the combination of the binding cavity with the substrate in an alkaline environment and may make its structure more stable.

scholarly journals Chitosan Films Functionalized with Different Hydroxycinnamic Acids: Preparation, Characterization and Application for Pork Preservation

Foods ◽  
2021 ◽  
Vol 10 (3) ◽  
pp. 536
Author(s):  
Huimin Yong ◽  
Yunpeng Liu ◽  
Dawei Yun ◽  
Shuai Zong ◽  
Changhai Jin ◽  
...  
Keyword(s):  
Ferulic Acid ◽  
Caffeic Acid ◽  
Food Packaging ◽  
Uv Light ◽  
Antimicrobial Properties ◽  
Antimicrobial Activities ◽  
Hydroxycinnamic Acid ◽  
Hydroxycinnamic Acids ◽  
Coumaric Acid ◽  
Active Food Packaging

Hydroxycinnamic acids are one category of bioactive phenolic acids that are widely distributed in plants. In this study, chitosan (CS) was functionalized with three kinds of hydroxycinnamic acids (p-coumaric acid, caffeic acid and ferulic acid) through the carbodiimide-mediated grafting method. The obtained hydroxycinnamic-acid-grafted CSs (hydroxycinnamic acid-g-CSs) were further fabricated into food packaging films through solvent casting. For the first time, the functionalities of the different hydroxycinnamic acid-g-CS films were compared. Results showed the grafting ratio of p-coumaric acid-g-CS, caffeic acid-g-CS and ferulic acid-g-CS was 73.68, 129.42 and 91.75 mg/g, respectively. Instrumental analyses confirmed hydroxycinnamic acids conjugated with CS through amide and ester bonds. The functionalization of CS film with hydroxycinnamic acids produced a more compact microstructure and higher UV light barrier ability, mechanical strength, water vapor barrier ability, thermal stability and antioxidant and antimicrobial activities. Among the different hydroxycinnamic acid-g-CS films, caffeic acid-g-CS film presented the strongest barrier, mechanical, antioxidant and antimicrobial properties. Moreover, caffeic acid-g-CS film packaging effectively extended the shelf life of pork to 10 days at 4 °C. Our results suggest caffeic acid-g-CS film can be used in the active food packaging field.

scholarly journals Coordinated Regulation of Species-Specific Hydroxycinnamic Acid Degradation and Siderophore Biosynthesis Pathways in Agrobacterium fabrum

2016 ◽  
Vol 82 (12) ◽  
pp. 3515-3524 ◽  
Author(s):  
Jessica Baude ◽  
Ludovic Vial ◽  
Camille Villard ◽  
Tony Campillo ◽  
Céline Lavire ◽  
...  
Keyword(s):  
Ferulic Acid ◽  
Iron Acquisition ◽  
Carbon Sources ◽  
Degradation Pathway ◽  
Hydroxycinnamic Acid ◽  
Plant Roots ◽  
Coumaric Acid ◽  
Content Type ◽  
Acid Degradation ◽  
Coordinated Expression

ABSTRACTThe rhizosphere-inhabiting speciesAgrobacterium fabrum(genomospecies G8 of theAgrobacterium tumefaciensspecies complex) is known to degrade hydroxycinnamic acids (HCAs), especially ferulic acid andp-coumaric acid, via the novelA. fabrumHCA degradation pathway. Gene expression profiles ofA. fabrumstrain C58 were investigated in the presence of HCAs, using a C58 whole-genome oligoarray. Both ferulic acid andp-coumaric acid caused variations in the expression of more than 10% of the C58 genes. Genes of theA. fabrumHCA degradation pathway, together with the genes involved in iron acquisition, were among the most highly induced in the presence of HCAs. Two operons coding for the biosynthesis of a particular siderophore, as well as genes of theA. fabrumHCA degradation pathway, have been described as being specific to the species. We demonstrate here their coordinated expression, emphasizing the interdependence between the iron concentration in the growth medium and the rate at which ferulic acid is degraded by cells. The coordinated expression of these functions may be advantageous in HCA-rich but iron-starved environments in which microorganisms have to compete for both iron and carbon sources, such as in plant roots. The present results confirm that there is cooperation between theA. fabrum-specific genes, defining a particular ecological niche.IMPORTANCEWe previously identified seven genomic regions inAgrobacterium fabrumthat were specifically present in all of the members of this species only. Here we demonstrated that two of these regions, encoding the hydroxycinnamic acid degradation pathway and the iron acquisition pathway, were regulated in a coordinated manner. The coexpression of these functions may be advantageous in hydroxycinnamic acid-rich but iron-starved environments in which microorganisms have to compete for both iron and carbon sources, such as in plant roots. These data support the view that bacterial genomic species emerged from a bacterial population by acquiring specific functions that allowed them to outcompete their closest relatives. In conclusion, bacterial species could be defined not only as genomic species but also as ecological species.

scholarly journals Improving the catalytic characteristics of phenolic acid decarboxylase from Bacillus amyloliquefaciens by the engineering of N-terminus and C-terminus

2020 ◽  
Author(s):  
Qin Li ◽  
Ying Xia ◽  
Ting Zhao ◽  
Yuanyuan Gong ◽  
Shangling Fang ◽  
...  
Keyword(s):  
Ferulic Acid ◽  
Phenolic Acid ◽  
Food Additives ◽  
Sinapic Acid ◽  
Alkali Resistance ◽  
Acid Decarboxylase ◽  
Coumaric Acid ◽  
C Terminus ◽  
N Terminus ◽  
Phenolic Acid Decarboxylase

Abstract Background: 4-vinylphenols produced by phenolic acid degradation catalyzed by phenolic acid decarboxylase can be used in food additives as well as flavor and fragrance industry. Improving the catalytic characters of phenolic acid decarboxylase is of great significance to enhance its practical application. Results: Mutants such as P-C, P-N, P-m1, P-m2, P-Nm1, and P-Nm2 were constructed by site-directed mutagenesis of P-WT. P-C showed better substrate affinities and higher turnover rates than P-WT for p-coumaric acid, ferulic acid, and sinapic acid; however, P-N had reduced affinity toward p-coumaric acid. The extension of the C-terminus increased its acid resistance, whereas the extension of the N-terminus contributed to the alkali resistance and heat resistance. The affinity of P-m1 to four substrates and that of P-m2 to p-coumaric acid and ferulic acid were greatly improved. However, the affinity of P-Nm2 to four phenolic acids was greatly reduced. The residual enzyme activities of P-Nm1 and P-Nm2 considerably improved compared with those of P-m1 and P-m2 after incubation at 50°C for 60 min.Conclusions: The extension of the N-terminus may be more conducive to the combination of the binding cavity with the substrate in an alkaline environment and may make its structure more stable.

scholarly journals Knockout of the p-Coumarate Decarboxylase Gene from Lactobacillus plantarum Reveals the Existence of Two Other Inducible Enzymatic Activities Involved in Phenolic Acid Metabolism

2000 ◽  
Vol 66 (8) ◽  
pp. 3368-3375 ◽  
Author(s):  
Lise Barthelmebs ◽  
Charles Divies ◽  
Jean-François Cavin
Keyword(s):  
Ferulic Acid ◽  
Lactobacillus Plantarum ◽  
Specific Activity ◽  
Reductase Activity ◽  
Enzymatic Activities ◽  
Gene Copy ◽  
Acid Decarboxylase ◽  
Decarboxylase Activity ◽  
Coumaric Acid

ABSTRACT Lactobacillus plantarum NC8 contains a pdcgene coding for p-coumaric acid decarboxylase activity (PDC). A food grade mutant, designated LPD1, in which the chromosomalpdc gene was replaced with the deleted pdc gene copy, was obtained by a two-step homologous recombination process using an unstable replicative vector. The LPD1 mutant strain remained able to weakly metabolize p-coumaric and ferulic acids into vinyl derivatives or into substituted phenyl propionic acids. We have shown that L. plantarum has a second acid phenol decarboxylase enzyme, better induced with ferulic acid than withp-coumaric acid, which also displays inducible acid phenol reductase activity that is mostly active when glucose is added. Those two enzymatic activities are in competition for p-coumaric and ferulic acid degradation, and the ratio of the corresponding derivatives depends on induction conditions. Moreover, PDC appeared to decarboxylate ferulic acid in vitro with a specific activity of about 10 nmol · min−1 · mg−1 in the presence of ammonium sulfate. Finally, PDC activity was shown to confer a selective advantage on LPNC8 grown in acidic media supplemented withp-coumaric acid, compared to the LPD1 mutant devoid of PDC activity.

Chemoenzymatic cascade for stilbene production from cinnamic acid catalyzed by ferulic acid decarboxylase and an artificial metathease

2019 ◽  
Vol 9 (20) ◽  
pp. 5572-5576 ◽  
Author(s):  
M. A. Stephanie Mertens ◽  
Daniel F. Sauer ◽  
Ulrich Markel ◽  
Johannes Schiffels ◽  
Jun Okuda ◽  
...  
Keyword(s):  
Ferulic Acid ◽  
Cinnamic Acid ◽  
Olefin Metathesis ◽  
Metal Contamination ◽  
Cascade Reaction ◽  
Acid Decarboxylase ◽  
Efficient Removal ◽  
Ferulic Acid Decarboxylase ◽  
Acid Catalyzed ◽  
Removal Of Metal

We report a chemoenzymatic cascade reaction for stilbene production combining decarboxylation and olefin metathesis with efficient removal of metal contamination.

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