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Antioxidative effects of quercetin-glycosides isolated from the flower buds of Tussilago farfara L.
Food Chem Toxicol. 2006 Aug; 44(8):1299-307.FC

Abstract

A bioassay-guided fractionation of the ethylacetate soluble fraction from the flower buds of Tussilago farfara L. (Compositae) yielded two flavonoids, quercetin 3-O-beta-L-arabinopyranoside and quercetin 3-O-beta-D-glucopyranoside. These two sugar conjugates of quercetin exhibited higher antioxidative activity than their aglycone, quercetin by NBT superoxide scavenging assay. Moreover, treatment with quercetin 3-O-beta-L-arabinopyranoside significantly increased the total glutathione (GSH) contents and the protein level of gamma-glutamylcysteine ligase (gamma-GCL), a key enzyme required for glutathione (GSH) synthesis in a rat hepatocyte cell line. Subcellular fractionation and reporter gene analysis using antioxidant response element (ARE) construct revealed that quercetin 3-O-beta-L-arabinopyranoside increased the level of nuclear Nrf2 and reporter activity, and that these were associated with the induction of the gamma-GCL gene. After 24 h incubation of cells with quercetin 3-O-beta-L-arabinopyranoside, 23% of the glycoside was converted to its aglycone, quercetin, but gamma-GCL was not induced by 7 microM (23%) quercetin. These results suggest that the two quercetin-glycosides isolated from T. farfara L. have direct antioxidative properties, and that quercetin 3-O-beta-L-arabinopyranoside increases the cellular GSH level by inducing the gamma-GCL gene. These novel effects of quercetin-glycosides are suggestive to underlie the potential putative chemopreventive effects of T. farfara L.

Authors+Show Affiliations

Kim MR
Research Center for Proteineous Materials, Chosun University, Gwangju 501-759, South Korea.
Lee JY
No affiliation info available
Lee HH
No affiliation info available
Aryal DK
No affiliation info available
Kim YG
No affiliation info available
Kim SK
No affiliation info available
Woo ER
No affiliation info available
Kang KW
No affiliation info available

MeSH

AnimalsCell LineEnzyme InductionFlavonoidsFlowersFree Radical ScavengersGene Expression Regulation, EnzymologicGlutamate-Cysteine LigaseGlutathioneGlutathione TransferaseGlycosidesHepatocytesMolecular ConformationNF-E2-Related Factor 2Nitroblue TetrazoliumNuclear Magnetic Resonance, BiomolecularRatsSuperoxidesTranscriptional ActivationTussilago

Pub Type(s)

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

Language

eng

PubMed ID

16574296

Citation

Kim, Mi-Ran, et al. "Antioxidative Effects of Quercetin-glycosides Isolated From the Flower Buds of Tussilago Farfara L." Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association, vol. 44, no. 8, 2006, pp. 1299-307.
Kim MR, Lee JY, Lee HH, et al. Antioxidative effects of quercetin-glycosides isolated from the flower buds of Tussilago farfara L. Food Chem Toxicol. 2006;44(8):1299-307.
Kim, M. R., Lee, J. Y., Lee, H. H., Aryal, D. K., Kim, Y. G., Kim, S. K., Woo, E. R., & Kang, K. W. (2006). Antioxidative effects of quercetin-glycosides isolated from the flower buds of Tussilago farfara L. Food and Chemical Toxicology : an International Journal Published for the British Industrial Biological Research Association, 44(8), 1299-307.
Kim MR, et al. Antioxidative Effects of Quercetin-glycosides Isolated From the Flower Buds of Tussilago Farfara L. Food Chem Toxicol. 2006;44(8):1299-307. PubMed PMID: 16574296.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Antioxidative effects of quercetin-glycosides isolated from the flower buds of Tussilago farfara L. AU - Kim,Mi-Ran, AU - Lee,Jeong Yong, AU - Lee,Hyang-Hee, AU - Aryal,Dipendra Kuma, AU - Kim,Yoon Gyoon, AU - Kim,Sang Kyum, AU - Woo,Eun-Rhan, AU - Kang,Keon Wook, Y1 - 2006/03/06/ PY - 2005/03/17/received PY - 2006/01/05/revised PY - 2006/02/17/accepted PY - 2006/4/1/pubmed PY - 2006/9/20/medline PY - 2006/4/1/entrez SP - 1299 EP - 307 JF - Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association JO - Food Chem Toxicol VL - 44 IS - 8 N2 - A bioassay-guided fractionation of the ethylacetate soluble fraction from the flower buds of Tussilago farfara L. (Compositae) yielded two flavonoids, quercetin 3-O-beta-L-arabinopyranoside and quercetin 3-O-beta-D-glucopyranoside. These two sugar conjugates of quercetin exhibited higher antioxidative activity than their aglycone, quercetin by NBT superoxide scavenging assay. Moreover, treatment with quercetin 3-O-beta-L-arabinopyranoside significantly increased the total glutathione (GSH) contents and the protein level of gamma-glutamylcysteine ligase (gamma-GCL), a key enzyme required for glutathione (GSH) synthesis in a rat hepatocyte cell line. Subcellular fractionation and reporter gene analysis using antioxidant response element (ARE) construct revealed that quercetin 3-O-beta-L-arabinopyranoside increased the level of nuclear Nrf2 and reporter activity, and that these were associated with the induction of the gamma-GCL gene. After 24 h incubation of cells with quercetin 3-O-beta-L-arabinopyranoside, 23% of the glycoside was converted to its aglycone, quercetin, but gamma-GCL was not induced by 7 microM (23%) quercetin. These results suggest that the two quercetin-glycosides isolated from T. farfara L. have direct antioxidative properties, and that quercetin 3-O-beta-L-arabinopyranoside increases the cellular GSH level by inducing the gamma-GCL gene. These novel effects of quercetin-glycosides are suggestive to underlie the potential putative chemopreventive effects of T. farfara L. SN - 0278-6915 UR - https://www.unboundmedicine.com/medline/citation/16574296/Antioxidative_effects_of_quercetin_glycosides_isolated_from_the_flower_buds_of_Tussilago_farfara_L_ DB - PRIME DP - Unbound Medicine ER -