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The C-Glycosylation of Flavonoids in Cereals

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The C-Glycosylation of Flavonoids in Cereals. / Brazier-Hicks, Melissa; Evans, Kathryn M.; Gershater, Markus C.; Puschmann, Horst; Steel, Patrick G.; Edwards, Robert.

In: Journal of Biological Chemistry, Vol. 284, No. 27, 03.07.2009, p. 17926-17934.

Research output: Contribution to journalArticlepeer-review

Harvard

Brazier-Hicks, M, Evans, KM, Gershater, MC, Puschmann, H, Steel, PG & Edwards, R 2009, 'The C-Glycosylation of Flavonoids in Cereals', Journal of Biological Chemistry, vol. 284, no. 27, pp. 17926-17934. https://doi.org/10.1074/jbc.M109.009258

APA

Brazier-Hicks, M., Evans, K. M., Gershater, M. C., Puschmann, H., Steel, P. G., & Edwards, R. (2009). The C-Glycosylation of Flavonoids in Cereals. Journal of Biological Chemistry, 284(27), 17926-17934. https://doi.org/10.1074/jbc.M109.009258

Vancouver

Brazier-Hicks M, Evans KM, Gershater MC, Puschmann H, Steel PG, Edwards R. The C-Glycosylation of Flavonoids in Cereals. Journal of Biological Chemistry. 2009 Jul 3;284(27):17926-17934. https://doi.org/10.1074/jbc.M109.009258

Author

Brazier-Hicks, Melissa ; Evans, Kathryn M. ; Gershater, Markus C. ; Puschmann, Horst ; Steel, Patrick G. ; Edwards, Robert. / The C-Glycosylation of Flavonoids in Cereals. In: Journal of Biological Chemistry. 2009 ; Vol. 284, No. 27. pp. 17926-17934.

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@article{e0a76edce88c4a25b86a1e5ee34a7e82,
title = "The C-Glycosylation of Flavonoids in Cereals",
abstract = "Flavonoids normally accumulate in plants as O-glycosylated derivatives, but several species, including major cereal crops, predominantly synthesize flavone-C-glycosides, which are stable to hydrolysis and are biologically active both in planta and as dietary components. An enzyme (OsCGT) catalyzing the UDP-glucosedependent C-glucosylation of 2-hydroxyflavanone precursors of flavonoids has been identified and cloned from rice (Oryza sativa ssp. indica), with a similar protein characterized in wheat (Triticum aestivum L.). OsCGT is a 49-kDa family 1 glycosyltransferase related to known O-glucosyltransferases. The recombinant enzyme C-glucosylated 2-hydroxyflavanones but had negligible O-glucosyltransferase activity with flavonoid acceptors. Enzyme chemistry studies suggested that OsCGT preferentially C-glucosylated the dibenzoylmethane tautomers formed in equilibrium with 2-hydroxyflavanones. The resulting 2-hydroxyflavanone-C-glucosides were unstable and spontaneously dehydrated in vitro to yield a mixture of 6C-and 8C-glucosyl derivatives of the respective flavones. In contrast, in planta, only the respective 6C-glucosides accumulated. Consistent with this selectivity in glycosylation product, a dehydratase activity that preferentially converted 2-hydroxyflavanone-C-glucosides to the corresponding flavone-6C-glucosides was identified in both rice and wheat. Our results demonstrate that cereal crops synthesize C-glucosylated flavones through the concerted action of a CGT and dehydratase acting on activated 2-hydroxyflavanones, as an alternative means of generating flavonoid metabolites.",
keywords = "ANTIBIOTIC URDAMYCIN, SECONDARY METABOLISM, ARABIDOPSIS-THALIANA, IN-VITRO, BIOSYNTHESIS, IDENTIFICATION, GLYCOSYLTRANSFERASE, RICE, GLUCOSYLTRANSFERASE, GLYCOSIDES",
author = "Melissa Brazier-Hicks and Evans, {Kathryn M.} and Gershater, {Markus C.} and Horst Puschmann and Steel, {Patrick G.} and Robert Edwards",
year = "2009",
month = jul,
day = "3",
doi = "10.1074/jbc.M109.009258",
language = "English",
volume = "284",
pages = "17926--17934",
journal = "The Journal of biological chemistry",
issn = "0021-9258",
publisher = "American Society for Biochemistry and Molecular Biology Inc.",
number = "27",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - The C-Glycosylation of Flavonoids in Cereals

AU - Brazier-Hicks, Melissa

AU - Evans, Kathryn M.

AU - Gershater, Markus C.

AU - Puschmann, Horst

AU - Steel, Patrick G.

AU - Edwards, Robert

PY - 2009/7/3

Y1 - 2009/7/3

N2 - Flavonoids normally accumulate in plants as O-glycosylated derivatives, but several species, including major cereal crops, predominantly synthesize flavone-C-glycosides, which are stable to hydrolysis and are biologically active both in planta and as dietary components. An enzyme (OsCGT) catalyzing the UDP-glucosedependent C-glucosylation of 2-hydroxyflavanone precursors of flavonoids has been identified and cloned from rice (Oryza sativa ssp. indica), with a similar protein characterized in wheat (Triticum aestivum L.). OsCGT is a 49-kDa family 1 glycosyltransferase related to known O-glucosyltransferases. The recombinant enzyme C-glucosylated 2-hydroxyflavanones but had negligible O-glucosyltransferase activity with flavonoid acceptors. Enzyme chemistry studies suggested that OsCGT preferentially C-glucosylated the dibenzoylmethane tautomers formed in equilibrium with 2-hydroxyflavanones. The resulting 2-hydroxyflavanone-C-glucosides were unstable and spontaneously dehydrated in vitro to yield a mixture of 6C-and 8C-glucosyl derivatives of the respective flavones. In contrast, in planta, only the respective 6C-glucosides accumulated. Consistent with this selectivity in glycosylation product, a dehydratase activity that preferentially converted 2-hydroxyflavanone-C-glucosides to the corresponding flavone-6C-glucosides was identified in both rice and wheat. Our results demonstrate that cereal crops synthesize C-glucosylated flavones through the concerted action of a CGT and dehydratase acting on activated 2-hydroxyflavanones, as an alternative means of generating flavonoid metabolites.

AB - Flavonoids normally accumulate in plants as O-glycosylated derivatives, but several species, including major cereal crops, predominantly synthesize flavone-C-glycosides, which are stable to hydrolysis and are biologically active both in planta and as dietary components. An enzyme (OsCGT) catalyzing the UDP-glucosedependent C-glucosylation of 2-hydroxyflavanone precursors of flavonoids has been identified and cloned from rice (Oryza sativa ssp. indica), with a similar protein characterized in wheat (Triticum aestivum L.). OsCGT is a 49-kDa family 1 glycosyltransferase related to known O-glucosyltransferases. The recombinant enzyme C-glucosylated 2-hydroxyflavanones but had negligible O-glucosyltransferase activity with flavonoid acceptors. Enzyme chemistry studies suggested that OsCGT preferentially C-glucosylated the dibenzoylmethane tautomers formed in equilibrium with 2-hydroxyflavanones. The resulting 2-hydroxyflavanone-C-glucosides were unstable and spontaneously dehydrated in vitro to yield a mixture of 6C-and 8C-glucosyl derivatives of the respective flavones. In contrast, in planta, only the respective 6C-glucosides accumulated. Consistent with this selectivity in glycosylation product, a dehydratase activity that preferentially converted 2-hydroxyflavanone-C-glucosides to the corresponding flavone-6C-glucosides was identified in both rice and wheat. Our results demonstrate that cereal crops synthesize C-glucosylated flavones through the concerted action of a CGT and dehydratase acting on activated 2-hydroxyflavanones, as an alternative means of generating flavonoid metabolites.

KW - ANTIBIOTIC URDAMYCIN

KW - SECONDARY METABOLISM

KW - ARABIDOPSIS-THALIANA

KW - IN-VITRO

KW - BIOSYNTHESIS

KW - IDENTIFICATION

KW - GLYCOSYLTRANSFERASE

KW - RICE

KW - GLUCOSYLTRANSFERASE

KW - GLYCOSIDES

UR - http://www.scopus.com/inward/record.url?scp=67650563940&partnerID=8YFLogxK

U2 - 10.1074/jbc.M109.009258

DO - 10.1074/jbc.M109.009258

M3 - Article

VL - 284

SP - 17926

EP - 17934

JO - The Journal of biological chemistry

JF - The Journal of biological chemistry

SN - 0021-9258

IS - 27

ER -