Bacterial antimutagenesis by hydroxycinnamic acids from plant cell walls

Ferguson, Lynnette R.; Lim, Isabel Fong; Pearson, Amira; Ralph, John; Harris, Philip J.

doi:10.1016/j.mrgentox.2003.08.005

Cited by 78 publications

(43 citation statements)

References 26 publications

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“…This study was based on the Salmonella reversion assay, which is widely used for the detection of antimutagenic agents, especially those present in plant extracts. [8][9][10][11] …”

Section: (Afl) Benzo[a]pyrene (B[a]p) and Hydrogenmentioning

confidence: 99%

Modulatory Effect of Byrsonima basiloba Extracts on the Mutagenicity of Certain Direct and Indirect-Acting Mutagens in Salmonella typhimurium Assays

Lira

Santos

Sannomiya

et al. 2008

Journal of Medicinal Food

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Byrsonima basiloba A. Juss. species is a native arboreal type from the Brazilian "cerrado" (tropical American savanna), and the local population uses it to treat diseases, such as diarrhea and gastric ulcer. It belongs to the Malpighiaceae family, and it is commonly known as "murici." Considering the popular use of B. basiloba derivatives and the lack of pharmacological potential studies regarding this vegetal species, the mutagenic and antimutagenic effect of methanol (MeOH) and chloroform extracts were evaluated by the Ames test, using strains TA97a, TA98, TA100, and TA102 of Salmonella typhimurium. No mutagenic activity was observed in any of the extracts. To evaluate the antimutagenic potential, direct and indirect mutagenic agents were used: 4 nitro-o-phenylenediamine, sodium azide, mitomycin C, aflatoxin B 1 , benzo[a]pyrene, and hydrogen peroxide. Both the extracts evaluated showed antimutagenic activity, but the highest value of inhibition level (89%) was obtained with the MeOH extract and strain TA100 in the presence of aflatoxin B 1 . Phytochemical analysis of the extracts revealed the presence of n-alkanes, lupeol, ursolic and oleanolic acid, (ϩ)-catechin, quercetin-3-O-␣-L-arabinopyranoside, gallic acid, methyl gallate, amentoflavone, quercetin, quercetin-3-O-(2Љ-O-galloyl)-␤-D-galactopyranoside, and quercetin-3-O-(2Љ-O-galloyl)-␣-L-arabinopyranoside.

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“…This study was based on the Salmonella reversion assay, which is widely used for the detection of antimutagenic agents, especially those present in plant extracts. [8][9][10][11] …”

Section: (Afl) Benzo[a]pyrene (B[a]p) and Hydrogenmentioning

confidence: 99%

Modulatory Effect of Byrsonima basiloba Extracts on the Mutagenicity of Certain Direct and Indirect-Acting Mutagens in Salmonella typhimurium Assays

Lira

Santos

Sannomiya

et al. 2008

Journal of Medicinal Food

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“…From a food science and nutrition prospective, hydroxycinnamate cross-links are involved in explaining dough and baked good properties (Hartmann et al 2005;Piber and Koehler 2005;Flander et al 2008), formation of gels (Oosterveld et al 2000;CarvajalMillan et al 2005aCarvajalMillan et al , b, c, 2006Robertson et al 2008), crispness and softening of fruits and vegetables Ng et al 1998;Parker et al 2003;Waldron et al 2003), post-harvest changes of asparagus accompanied by sensory toughness (Rodriguez-Arcos et al 2004;Rodriguez et al 2005;Jaramillo et al 2007) and physico-chemical properties of dietary fibers (Bunzel et al 2001). Finally, some the hydroxycinnamates and their derivatives are discussed as bioactive phytochemicals in-vitro (Graf 1992;GarciaConesa et al 1997;Ferguson et al 2003;Neudörffer et al 2006;Russell et al 2008) possibly promoting health benefits in the human body as described in more detail in other review articles in this special issue of Phytochemistry Reviews.…”

Section: Introductionmentioning

confidence: 99%

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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“…Ferulate and diferulate cross-links contribute to cell wall stiVening, anchoring of lignin in cell walls, cessation of plant growth, enhanced plant pest resistance, and reduced enzymatic hydrolysis of cell walls (Schopfer 1996;Bergvinson et al 1997;Grabber et al 1998;Casler and Jung 1999;MacAdam and Grabber 2002;Bily et al 2003). Ferulate and diferulates may also act as nucleation sites for lignin formation (Ralph et al 1995;Grabber et al 2002) and they play a role in the physical and antioxidant properties of foods Schooneveld-Bergmans et al 1999;Ferguson et al 2003).…”

Section: Introductionmentioning

confidence: 99%

Formation of syringyl-rich lignins in maize as influenced by feruloylated xylans and p-coumaroylated monolignols

Grabber

2007

Planta

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Grass cell walls are atypical because their xylans are acylated with ferulate and lignins are acylated with p-coumarate. To probe the role and interactions of these p-hydroxycinnamates during lignification, feruloylated primary cell walls isolated from maize cell suspensions were lignified with coniferyl and sinapyl alcohols and with varying levels of p-coumarate esters. Ferulate xylan esters enhanced the formation of wall-bound syringyl lignin more than methyl p-coumarate, however, maximal concentrations of syringyl lignin were only one-third that of guaiacyl lignin. Including sinapyl p-coumarate, the presumed precursor of p-coumaroylated lignins, with monolignols unexpectedly accelerated peroxidase inactivation, interfered with ferulate copolymerization into lignin, and had minimal or adverse effects on cell wall lignification. Free phenolic groups of p-coumarate esters in isolated maize lignin and pith cell walls did not undergo oxidative coupling with each other or with added monolignols. Thus, the extensive formation of syringyl-rich lignins and the functional role of extensive lignin acylation by p-coumarate in grasses remains a mystery.

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Bacterial antimutagenesis by hydroxycinnamic acids from plant cell walls

Cited by 78 publications

References 26 publications

Modulatory Effect of Byrsonima basiloba Extracts on the Mutagenicity of Certain Direct and Indirect-Acting Mutagens in Salmonella typhimurium Assays

Modulatory Effect of Byrsonima basiloba Extracts on the Mutagenicity of Certain Direct and Indirect-Acting Mutagens in Salmonella typhimurium Assays

Chemistry and occurrence of hydroxycinnamate oligomers

Formation of syringyl-rich lignins in maize as influenced by feruloylated xylans and p-coumaroylated monolignols

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