Transformation of 3,5-dimethoxy,4-hydroxy cinnamic acid by polyphenol oxidase from the fungus Trametes versicolor: product elucidation studies.

@article{Lacki1998TransformationO3,
  title={Transformation of 3,5-dimethoxy,4-hydroxy cinnamic acid by polyphenol oxidase from the fungus Trametes versicolor: product elucidation studies.},
  author={Karol M. Lacki and Zdravko Duvnjak},
  journal={Biotechnology and bioengineering},
  year={1998},
  volume={57 6},
  pages={
          694-703
        }
}
  • K. Lacki, Z. Duvnjak
  • Published 20 March 1998
  • Chemistry, Medicine
  • Biotechnology and bioengineering
Sinapic acid (SA), 3,5-dimethoxy,4-hydroxy cinnamic acid, was incubated with a crude polyphenol oxidase from the fungus Trametes versicolor. Some products of this transformation were isolated and their structures identified using mass spectrometry, nuclear magnetic resonance and Fourier transform infrared spectroscopy, and X-ray crystallography. It was found that the enzymatic oxidation of SA includes two distinct phases. In the initial phase SA is enzymatically transformed to r-1H-2c,6c-bis-(4… Expand
Transformation of N ′,N ′-dimethyl-N -(hydroxyphenyl)ureas by laccase from the white rot fungus Trametes versicolor
Abstract Transformation of N′,N′-dimethyl-N-(hydroxyphenyl)ureas was assayed in the presence of purified laccase produced by the fungus Trametes versicolor. The para- and ortho-hydroxyphenylExpand
Biotransformation of 3-hydroxydibenzo-α-pyrone into 3,8 dihydroxydibenzo-α-pyrone and aminoacyl conjugates by Aspergillus niger isolated from native“shilajit”
"Shilajit" is a panacea in Ayurveda, the Indian traditional system of medicine. The major bioactives of "shilajit" have been identified as dibenzo-α-pyrones (DBPs), its oligomers and aminoacylExpand
P-hydroxycinnamic acids as natural mediators for laccase oxidation of recalcitrant compounds.
TLDR
Investigation of TBARS (thiobarbituric acid-reactive-substances) from unsaturated fatty acids revealed that laccase can also initiate lipid peroxidation reactions in the presence of p-hydroxycinnamic acids enabling oxidation of the most recalcitrant PAH. Expand
Formation of thomasidioic acid from dehydrosinapinic acid dilactone under neutral conditions, and a remaining inhibitory activity against peroxynitrite-mediated protein nitration.
TLDR
Dehydrosinapinic acid dilactone was converted to thomasidioic acid and (E,E)-2,3-bis(3,5-dimethoxy-4-hydroxybenzylidene)succinic acid via an alpha,beta-unsaturated gamma-lactone type dimer in phosphate buffer to prevent peroxynitrite-mediated protein nitration. Expand
Identification and formation pathway of laccase-mediated oxidation products formed from hydroxyphenylureas.
TLDR
It is demonstrated that fungal laccases could assist the transformation of hydroxyphenylureas by establishing that the pH of the reaction has a strong influence on both the kinetics of the Reaction and the nature of the transformation products. Expand
Structural insight into the oxidation of sinapic acid by CotA laccase.
TLDR
This work establishes structure-function relationships for laccase-natural mediator system by analyzing interactions between CotA and SA and indicated that the presence of methoxy groups in the ortho-position of the phenolic structure is crucial for the substrate recognition by CotA laccases. Expand
Inhibitory mechanism of sinapinic acid against peroxynitrite‐mediated tyrosine nitration of protein in vitro
TLDR
It is proposed that the ML of sinapinic acid is generated via one‐electron oxidation by peroxynitrite treatment by nuclear magnetic resonance (NMR) and liquid chromatography‐mass spectrometry (LC‐MS). Expand
Cloning and characterization of a new laccase from Bacillus licheniformis catalyzing dimerization of phenolic acids
TLDR
A new laccase gene (cotA) was cloned from Bacillus licheniformis and expressed in Escherichia coli and showed spectroscopic properties, typical for blue multi-copper oxidases, and highest activity of CotA was found towards sinapic acid. Expand
Biodegradation of cinnamates by white-rot fungus, Phlebia radiata
th day of the cultivation. The evolution of carbon dioxide from aliphatic chain cleavage cinnamate showed very similar trend which demonstrated simultaneous process with the decarboxylation ones onExpand
Comparative characterization of four laccases from Trametes versicolor concerning phenolic C-C coupling and oxidation of PAHs.
TLDR
Investigation of the structural basis of the different activities of the laccases demonstrated the impact of positions 164 and 265 in the substrate binding site on oxidation of PAHs. Expand
...
1
2
3
...

References

SHOWING 1-10 OF 22 REFERENCES
Transformation of 3,5‐dimethoxy‐4‐hydroxy cinnamic acid and its derivatives using enzyme from white‐rot fungus Trametes versicolor: Enzyme characteristics and its application
Transformation of 3,5-dimethoxy-4-hydroxy cinnamic acid (sinapic acid), sinapaldehyde, sinapine and sinapoyl in the model system containing an enzyme secreted by the fungus Trametes versicolor wasExpand
Enzymatic oligomerization of vanillic acid
Abstract When vanillic acid was incubated with an extracellular laccase from the fungus Rhizoctonia praticola , the formation of various oligomeric products was observed ranging from dimers toExpand
Modeling the enzymatic transformation of 3,5‐dimethoxy,4‐hydroxy cinnamic acid by polyphenoloxidase from the white‐rot fungus Trametes versicolor
TLDR
It is shown that, in the open system, the observed change in the enzyme activity at higher temperatures was caused by two opposing phenomena: an Arrhenius effect which increased the rate, and a solubility effect which reduced the rate due to a lower oxygen concentration. Expand
Degradation of Trimeric Lignin Model Compounds, Arylglycerol-β-syringaresinol Ethers, by Fusarium solani M-13-1
Trimeric lignin model compounds, arylglycerol-β-syringaresinol ethers, were incubated with Fusarium solani M-13-1 in basal salts medium with shaking. From the culture filtrates, degradation productsExpand
Transformation Of : Its Significance In Humification trans : Its Significance In Humification-4-hydroxycinnamic Acid By A Laccase Of The Fungus : Its Significance In Humification trametes Versicolor : Its Significance In Humification
A lignin precursor, trans-4-hydroxycinnamic acid, was incubated with an extracellular laccase from the fungus Trametes versicolor. Oxidative coupling of the substrate occurred, and dimers wereExpand
Cooperation between fungal laccase and glucose oxidase in the degradation of lignin derivatives
Abstract In the presence of Trametes versicolor laccase, generation of quinonoid intermediates formed from a high-molecular-weight fraction of lignosulphonates (Peritan Na) was observed. The additionExpand
Purpling reaction of sinapic acid model systems containing L-DOPA and mushroom tyrosinase
To explain the formation of purple lesions in washed mushrooms during postharvest storage, the reactions of phenolic acids with quinones formed in the oxidation of catechol and L-DOPA by mushroomExpand
Significance of glucose oxidase in lignin degradation
TLDR
Spectrophotometric studies reported here on the interaction of glucose oxidase with transitory quinone and free-radical lignol oxidation products demonstrate that these intermediates are capable of serving as co-substrates of the reduced flavoenzyme at low oxygen tensions. Expand
Comparative Studies of Extracellular Fungal Laccases
TLDR
All laccases oxidized the methoxyphenolic acids under investigation, but there existed quantitative differences in oxidation efficiencies which depended on pH and on the nature (noninduced or induced) of the enzyme. Expand
Exhaustive laccase-catalysed oxidation of a lignin model compound (vanillyl glycol) produces methanol and polymeric quinoid products.
TLDR
The participation of quinone formation in the polymerization process and the possible role of such intermediates in lignin biodegradation is discussed. Expand
...
1
2
3
...