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Structural characterization of the major flavonoid glycosides from Arabidopsis thaliana seeds.
J Agric Food Chem. 2006 Sep 06; 54(18):6603-12.JA

Abstract

Information gains from the seed of the model plant Arabidopsis thaliana (Brassicaceae) have greatly contributed to a better understanding of flavonoid synthesis and may be used for crop improvement. However, exhaustive identification of the flavonoid accumulated in Arabidopsis seed was still lacking. Complementary investigations of seed flavonoids by LC-ESI-MS, LC-ESI-MS-MS, and NMR spectroscopy in Arabidopsis led to full characterization of monoglycosides, namely, quercetin 3-O-alpha-rhamnopyranoside and kaempferol 3-O-alpha-rhamnopyranoside, and diglycosides, namely, quercetin and kaempferol 3-O-beta-glucopyranoside-7-O-alpha-rhamnopyranoside and quercetin and kaempferol 3,7-di-O-alpha-rhamnopyranoside. Interestingly, the tt7 mutant that lacks flavonoid-3'-hydroxylase and consequently accumulates only kaempferol derivatives was shown to contain three additional products, kaempferol 3-O-beta-glucopyranoside, kaempferol 3-O-alpha-rhamnopyranoside-7-O-beta-glucopyranoside, and the triglycoside kaempferol 3-O-beta-[alpha-rhamnopyranosyl(1-->2)-glucopyranoside]-7-O-alpha-rhamnopyranoside. Taken together these results allow a scheme for flavonol glycosylation to be proposed.

Authors+Show Affiliations

Kerhoas L
Unité de Phytopharmacie et Médiateurs Chimiques and Laboratoire de Biologie des Semences, INRA, route de St Cyr, 78026 Versailles cedex, France.
Aouak D
No affiliation info available
Cingöz A
No affiliation info available
Routaboul JM
No affiliation info available
Lepiniec L
No affiliation info available
Einhorn J
No affiliation info available
Birlirakis N
No affiliation info available

MeSH

ArabidopsisCarbohydrate ConformationChromatography, LiquidFlavonoidsGlycosidesMagnetic Resonance SpectroscopyMolecular StructureSeedsSpectrometry, Mass, Electrospray Ionization

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

16939316

Citation

Kerhoas, Lucien, et al. "Structural Characterization of the Major Flavonoid Glycosides From Arabidopsis Thaliana Seeds." Journal of Agricultural and Food Chemistry, vol. 54, no. 18, 2006, pp. 6603-12.
Kerhoas L, Aouak D, Cingöz A, et al. Structural characterization of the major flavonoid glycosides from Arabidopsis thaliana seeds. J Agric Food Chem. 2006;54(18):6603-12.
Kerhoas, L., Aouak, D., Cingöz, A., Routaboul, J. M., Lepiniec, L., Einhorn, J., & Birlirakis, N. (2006). Structural characterization of the major flavonoid glycosides from Arabidopsis thaliana seeds. Journal of Agricultural and Food Chemistry, 54(18), 6603-12.
Kerhoas L, et al. Structural Characterization of the Major Flavonoid Glycosides From Arabidopsis Thaliana Seeds. J Agric Food Chem. 2006 Sep 6;54(18):6603-12. PubMed PMID: 16939316.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Structural characterization of the major flavonoid glycosides from Arabidopsis thaliana seeds. AU - Kerhoas,Lucien, AU - Aouak,Denya, AU - Cingöz,Annabelle, AU - Routaboul,Jean-Marc, AU - Lepiniec,Loïc, AU - Einhorn,Jacques, AU - Birlirakis,Nicolas, PY - 2006/8/31/pubmed PY - 2006/10/21/medline PY - 2006/8/31/entrez SP - 6603 EP - 12 JF - Journal of agricultural and food chemistry JO - J Agric Food Chem VL - 54 IS - 18 N2 - Information gains from the seed of the model plant Arabidopsis thaliana (Brassicaceae) have greatly contributed to a better understanding of flavonoid synthesis and may be used for crop improvement. However, exhaustive identification of the flavonoid accumulated in Arabidopsis seed was still lacking. Complementary investigations of seed flavonoids by LC-ESI-MS, LC-ESI-MS-MS, and NMR spectroscopy in Arabidopsis led to full characterization of monoglycosides, namely, quercetin 3-O-alpha-rhamnopyranoside and kaempferol 3-O-alpha-rhamnopyranoside, and diglycosides, namely, quercetin and kaempferol 3-O-beta-glucopyranoside-7-O-alpha-rhamnopyranoside and quercetin and kaempferol 3,7-di-O-alpha-rhamnopyranoside. Interestingly, the tt7 mutant that lacks flavonoid-3'-hydroxylase and consequently accumulates only kaempferol derivatives was shown to contain three additional products, kaempferol 3-O-beta-glucopyranoside, kaempferol 3-O-alpha-rhamnopyranoside-7-O-beta-glucopyranoside, and the triglycoside kaempferol 3-O-beta-[alpha-rhamnopyranosyl(1-->2)-glucopyranoside]-7-O-alpha-rhamnopyranoside. Taken together these results allow a scheme for flavonol glycosylation to be proposed. SN - 0021-8561 UR - https://www.unboundmedicine.com/medline/citation/16939316/Structural_characterization_of_the_major_flavonoid_glycosides_from_Arabidopsis_thaliana_seeds_ L2 - https://doi.org/10.1021/jf061043n DB - PRIME DP - Unbound Medicine ER -