Biotransformation of Sinapic Acid Catalyzed by <i>Momordica charantia</i> Peroxidase

Liu, Haili; Wan, Xiang; Huang, Xuefeng; Kong, Ling‐Yi

doi:10.1021/jf0628072

Cited by 28 publications

(21 citation statements)

References 23 publications

(45 reference statements)

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“…The coupling products of the free acids significantly differ from the products obtained from using esters as starting materials (Ward et al 2001). As hydroxycinnamic acids tend to decarboxylate under these conditions (Ward et al 2001;Liu et al 2005Liu et al , 2007a) the coupling products do not represent possible products in the plant cell wall where ferulic acid is ester-linked to cell wall polysaccharides. Esterification, however, protects ferulic acid from being decarboxylated during oxidative coupling.…”

Section: Dehydrodiferulatesmentioning

confidence: 95%

“…As already described for ferulate dehydrodimers, model reactions using the free acids as starting materials are only of limited value to describe processes in the plant cell wall, but might be of interest for other purposes such as demonstrating the detoxification of ferulic acid by fungi. In model reactions using the free acids, ferulic acid (1, R = H), p-coumaric acid (2, R = H), sinapic acid (3, R = H) and caffeic acid 15 were coupled by using different peroxidases and coupling conditions (Ward et al 2001;Liu et al 2005Liu et al , 2007a; Monien et al 2006). Kong's group used peroxidase from Momordica charantia and H 2 O 2 in a buffer (pH 5.0)/acetone mixture to oligomerize p-coumaric, caffeic, ferulic, and sinapic acid and described this in four publications (Liu et al 2005(Liu et al , 2007aWan et al 2008 (Ward et al 2001;Liu et al 2005).…”

Section: Ferulate Trimers and Tetramers From Model Reactionsmentioning

confidence: 99%

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Chemistry and occurrence of hydroxycinnamate oligomers

2009

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Hydroxycinnamates such as ferulic acid, sinapic acid and p-coumaric acid ester-linked to plant cell wall polymers may act as cross-links between polysaccharides to each other, but also to proteins and lignin. Although sinapates and p-coumarates also form cell wall cross-links by the formation of radically or photochemically formed dimers, ferulate derivatives are the quantitatively most important cross-links in the plant cell wall. While the first radically generated ferulate dimer was already identified almost 40 years ago, the spectrum of known ferulate dimers was considerably broadened within the last 15 years. Higher ferulate oligomers were generated in model systems, but also isolated from plant materials. Different model systems using either free hydroxycinnamic acids or their esters are reviewed, highlighting a discussion of the relevance of these models for the plant cell wall. The first ferulate trimer from plant material was discovered in 2003 and seven dehydrotrimers of ferulic acid were isolated from maize bran since. Some of these trimers were also identified in other plant materials such as wheat and rye grains, corn stover, sugar beet and asparagus. Formation mechanisms of ferulate trimers and implications for the plant cell wall are discussed. Ferulate tetramers are the highest oligomers isolated from plant materials so far. These compounds can theoretically cross-link up to four polysaccharide chains, assuming all cross-links are formed intermolecularly. Formation of intramolecular versus intermolecular polysaccharide crosslinks is a key question to be answered in the future if we want to judge properly the importance of hydroxycinnamate cross-links in the plant cell wall.

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Section: Dehydrodiferulatesmentioning

confidence: 95%

Section: Ferulate Trimers and Tetramers From Model Reactionsmentioning

confidence: 99%

Chemistry and occurrence of hydroxycinnamate oligomers

2009

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“…Similar products were also generated after oxidizing mixtures of CA, ferulic acid (FA), p-coumaric acid (CouA) and sinapic acid (SA) with potato and horseradish peroxidase (Arrieta-Baez and Stark 2006) and mixtures of FA and resveratrol with M. charantia peroxidase (Yu et al 2007). The latter enzyme source was used to produce SA tetramers as well (Liu et al 2007). In the same fashion, the first step in the cascade of reactions that could lead to a CA tetramer is the formation of CA radicals, as claimed for peroxidase-catalyzed oxidation of ferulic acid (Oudgenoeg et al 2001;Derat and Shaik 2006), (Fig.…”

Section: Oxidation Mechanismmentioning

confidence: 99%

Biocatalytic properties of a peroxidase-active cell-free extract from onion solid wastes: caffeic acid oxidation

et al. 2008

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The exploitation of food residual sources consists of a major factor in reducing the polluting load of food industry wastes and developing novel added-value products. Plant food residues including trimmings and peels might contain a range of enzymes capable of transforming bio-organic molecules with potential phytotoxicity, including hydrolases, peroxidases and polyphenoloxidases. Although the use of bacterial and fungal enzymes has gained interest in studies pertaining to bioremediation applications, plant enzymes have been given less attention or even disregarded. In this view, this study aimed at the investigating the use of a crude peroxidase preparation from onion solid by-products for oxidising caffeic acid, a widespread o-diphenol, whose various derivatives may occur in food industry wastes, such as olive mill waste waters. Increased enzyme activity was observed at a pH value of 5, but considerable activity was also retained for pH up to 7. Favourable temperatures for increased activity varied between 20 degrees C and 40 degrees C, 30 degrees C being the optimal. Liquid chromatography-mass spectrometry analysis of a homogenate/H(2)O(2)-treated caffeic acid solution revealed the existence of a tetramer as major oxidation product. Based on the data generated, a putative pathway for the formation of the peroxidase-mediated caffeic acid tetramer was proposed.

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“…Momordica charantia peroxidase (MCP) is an easily obtainable peroxidase from the fruits of M. charantia. MCP has several advantages including economical source, enzyme pH stability, and thermostability, compared to the widely used horseradish peroxidase [2]. MCP has been a useful tool to facilitate oxidative coupling of substrates for new compounds with possible pharmacological activities [3 -5].…”

mentioning

confidence: 99%

Biocatalytic Production of Acyclic Bis[bibenzyls] from Dihydroresveratrol by Crude Momordica charantia Peroxidase

Xie¹,

Yuan²,

Qu³

et al. 2009

Chemistry & Biodiversity

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Biotransformation of dihydroresveratrol by crude Momordica charantia peroxidase provided six new acyclic bis[bibenzyls] 1-6. Their structures were established on the basis of NMR and MS analyses as C-C, C-O-C, and C-CH(2)-C dimers of dihydroresveratrol. Compounds 1-6 were tested for antiproliferative activity against human prostate cancer PC3 cell line in vitro, and 2 and 6 were found to be more potent than the parent compound.

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Biotransformation of Sinapic Acid Catalyzed by Momordica charantia Peroxidase

Cited by 28 publications

References 23 publications

Chemistry and occurrence of hydroxycinnamate oligomers

Chemistry and occurrence of hydroxycinnamate oligomers

Biocatalytic properties of a peroxidase-active cell-free extract from onion solid wastes: caffeic acid oxidation

Biocatalytic Production of Acyclic Bis[bibenzyls] from Dihydroresveratrol by Crude Momordica charantia Peroxidase

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