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Structure type: oligomer
Trivial name: f2
Compound class: glycoside, flavonoid glycoside, flavonol glycoside, flavone glycoside
Contained glycoepitopes: IEDB_136105,IEDB_142488,IEDB_146664,IEDB_225177,IEDB_885823,IEDB_983931,SB_192

• Article ID: 10734
  Pietta P, Mauri P, Bruno A, Zini L "High-performance liquid chromatography and micellar electrokinetic chromatography of flavonol glycosides from Tilia" - Journal of Chromatography A 638 (1993) 357-361
  

  The determination of nine different flavonol glycosides from Tilia using reversed-phase high-performance liquid chromatography (HPLC) and micellar electrokinetic chromatography (MEKC) is described. The analytes were monitored by on-line diode-array UV detection to identify peaks as quercetin or kaempferol derivatives. MEKC is confirmed as a useful complementary technique to HPLC.

  Publication DOI: 10.1016/0021-9673(93)83449-3
  Journal NLM ID: 9318488
  Publisher: Amsterdam; New York: Elsevier
  Institutions: Università degli Studi di Milano, Milan, Italy, ITBA-CNR, Milan, Italy
  Methods: HPLC, UV, hydrolysis, MEKC
  
   
  
  Tilia cordata, Tilia platyphyllos
  CSDB ID 139113 (all data & tools)
• Article ID: 10934
  Mulinacci N, Vincieri FF, Baldi A, Bambagiottialberti M, Sendl A, Wagner H "Flavonol glycosides from Sedum telephium subspecies maximum leaves" - Phytochemistry 38 (1995) 531-533
  

  Two new flavonol glycosides, kaempferol 3-O-β-neohesperidoside-7-O-α-rhamnoside and quercetin 3-O-β-neohesperidoside-7-O-α-rhamnoside were identified in the fresh leaves of Sedum telephium ssp. maximum. The known compounds, quercetin, kaempferol and their 3-glucosides, 7-rhamnosides and 3,7-dirhamnosides were also identified. All compounds were characterized by means of chemical and spectroscopic methods. NOE experiments were performed to detect the glycosidic bond at the 7-hydroxyl of the aglycone molecules.

  NOE, Crassulaceae, Sedum telephium ssp. maximum, flavonols, kaempferol 3-neohesperidoside-7-rhamnoside, quercetin 3-neohesperidoside-7-rhamnoside

  Publication DOI: 10.1016/0031-9422(94)00554-7
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Institute of Pharmaceutical Biology, University of Munich, Munich, Germany, Department of Pharmaceutical Science, University of Florence, Florence, Italy
  Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, HPLC, UV, HPTLC, CC
  
   
  
  Sedum telephium ssp. maximum
  CSDB ID 146627 (all data & tools)
• Article ID: 11236
  Yonekura-Sakakibara K, Tohge T, Niida R, Saito K "Identification of a flavonol 7-O-rhamnosyltransferase gene determining flavonoid pattern in Arabidopsis by transcriptome coexpression analysis and reverse genetics" - Journal of Biological Chemistry 282 (2007) 14932-14941
  

  Glycosylation plays a major role in the remarkable chemical diversity of flavonoids in plants including Arabidopsis thaliana. The wide diversity encoded by the large family-1 glycosyltransferase (UGT) gene family makes it difficult to determine the biochemical function of each gene solely from its primary sequence. Here we used transcriptome coexpression analysis combined with a reverse genetics approach to identify a gene that is prominent in determining the flavonoid composition of Arabidopsis. Using transcriptome coexpression analysis accessible on the ATTED-II public data base, the expression pattern of a UGT gene, UGT89C1, was found to be highly correlated with known flavonoid biosynthetic genes. No C-7 rhamnosylated flavonols were detected in either of two T-DNA ugt89c1 mutants. This specific metabolite deficiency in the mutants was complemented by stable transformation with the genomic fragment containing intact UGT89C1. Glutathione S-transferasefused recombinant UGT89C1 protein converted kaempferol 3-O-glucoside to kaempferol 3-O-glucoside-7-O-rhamnoside and recognized 3-O-glycosylated flavonols and UDP-rhamnose as substrates, but not flavonol aglycones, 3-O-glycosylated anthocyanins or other UDP-sugars. These results show that UGT89C1 is a flavonol 7-O-rhamnosyltransferase. The abundance of UGT89C1 transcripts in floral buds was consistent with the flavonoid accumulation of C-7 rhamnosylated flavonols in Arabidopsis organs. Our present study demonstrates that the integration of transcriptome coexpression analysis with a reverse genetic approach is a versatile tool for understanding a multigene family of a metabolic pathway in Arabidopsis.

  Publication DOI: 10.1074/jbc.M611498200
  Journal NLM ID: 2985121R
  Publisher: Baltimore, MD: American Society for Biochemistry and Molecular Biology
  Correspondence: ksaito@faculty.chiba-u.jp
  Institutions: RIKEN Plant Science Center, Suehiro-cho 1-7-22, Tsurumi-ku, Yokohama 230-0045, Japan, Graduate School of Pharmaceutical Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan
  Methods: biological assays, enzymatic assay, genetic manipulations, UPLC/PDA/ESI-Q-TOF/MS
  
   
  
  Arabidopsis thaliana
  CSDB ID 60953 (all data & tools)
• Article ID: 11654
  Li C, Gou Z, Yang Y, Zhang C "Chemical constituents of Cynanchum chinense R. Br." - Zhongguo Zhong Yao Za Zhi = Zhongguo Zhongyao Zazhi = China Journal of Chinese Materia Medica [Chinese] 24(6) (1999) 353-355
  

  Objective: To investigate the chemical constituents in the aerial part of Cynanchum chinense. Method: The chemical constituents were extracted with solvent and separated by column chromatography. The structures were identified by spectral methods. Result: The structures- were identified as 7-O-α-L-rhamnopyranosyl-kaermpferol-3-O-α-L-rhamnopyranoside, 7-O-α-L-rhamnopyranosyl-kaempferol-3-O-β-D-glucopyranoside and 7-O-α-L-rhamnopyranosyl-kaempferol-3-O-β-D-glucopyranosyl(1→2)-β-D-glucopyranoside. Conclusion: All the three compounds were separated from C. chinense for the first time.

  kaempferol, flavone, flavonoid glycoside, Cynanchum chinense

  NCBI PubMed ID: 12212028
  Journal NLM ID: 8913656
  WWW link: http://en.cnki.com.cn/Article_en/CJFDTOTAL-ZGZY906.016.htm
  Publisher: Zhongguo yao xue hui : Zhongguo Zhong yi yan jiu yuan Zhong yao yan jiu suo
  Institutions: Department of Pharmacy, Lanzhou Medical College, Lonzhou 730000, China
  
   
  
  Cynanchum chinense
  CSDB ID 62404 (all data & tools)
• Article ID: 11877
  Veit M, Pauli GF "Major flavonoids from Arabidopsis thaliana leaves" - Journal of Natural Products 62(9) (1999) 1301-1303
  

  The three major flavonoids isolated from Arabidopsis thaliana plants grown in the greenhouse were identified by means of spectroscopic analysis (UV, NMR, MS) and chiral capillary zone electrophoresis as the novel kaempferol 3-O-β-[β-D-glucopyranosyl(1→6)D-glucopyranoside]-7-O-α-L-rhamnopyranoside (1), kaempferol 3-O-β-D-glucopyranoside-7-O-α-L-rhamnopyranoside (2), and kaempferol 3-O-α-L-rhamnopyranoside-7-O-α-L-rhamnopyranoside (3). Comprehensive NMR studies including selective 1D and gradient-enhanced 2D techniques were applied in order to achieve full signal assignment and definitive proof of linkage for compound 1.

  flavonoid, Arabidopsis thaliana, flavone glycoside

  NCBI PubMed ID: 10514319
  Publication DOI: 10.1021/np990080o
  Journal NLM ID: 7906882
  Publisher: American Society of Pharmacognosy
  Correspondence: Pauli GF
  Institutions: Department of Pharmaceutical Biology, University of Würzburg, Würzburg, Germany, Institute of Pharmaceutical Biology and Phytochemistry, Westfälische Wilhelms-University, Hittorfstrasse 56, D-48149 Münster, Germany
  Methods: 13C NMR, 1H NMR, IR, TLC, MALDI-TOF MS, HPLC, UV, capillary electrophoresis (CE), TOCSY, HMBC, COSY, HSQC, HRMS, TFA hydrolysis, reduction with NaCNBH3, API-MS
  
   
  
  Arabidopsis thaliana
  CSDB ID 63334 (all data & tools)
• Article ID: 12199
  Gohar AA, Maatooq GT, Niwa M "Two flavonoid glycosides from Chenopodium murale" - Phytochemistry 53(2) (2000) 299-303
  

  Two new triglycosides, kaempferol-3-O-{(4-β-D-apiofuranosyl)-α-L-rhamnopyranoside}-7-O-α-L-rhamnopyranoside and kaempferol-3-O-{(4-β-D-xylopyranosyl)-α-L-rhamnopyranoside}-7-O-α-L-rhamnopyranoside were isolated from the methanol extract of Chenopodium murale, together with a known diglycoside, kaempferol-3-O-β-D-glucopyranoside-7-O-α-L-rhamnopyranoside. The characterization of the three compounds was achieved by various spectroscopic methods.

  glycosides, Chenopodiaceae, kaempferol, flavonoids, flavonols, Chenopodium murale

  NCBI PubMed ID: 10680187
  Publication DOI: 10.1016/s0031-9422(99)00525-7
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, Egypt, Department of Medicinal Resources Chemistry, Faculty of Pharmacy, Meijo University, Nagoya, Japan
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, acid hydrolysis, GLC, paper chromatography, HPLC, UV, extraction, optical rotation measurement, CC, melting point determination, precipitation, derivatization
  
   
  
  Chenopodium murale
  CSDB ID 65592 (all data & tools)
• Article ID: 12621
  Romani A, Pinelli P, Mulinacci N, Vincieri FF, Gravano E, Tattini M "HPLC analysis of flavonoids and secoiridoids in leaves of Ligustrum vulgare L. (Oleaceae)" - Journal of Agricultural and Food Chemistry 48(9) (2000) 4091-4096
  

  Identification and quantification of flavonol glycosides and secoiridoids was carried out on leaves of Ligustrum vulgare L. (Oleaceae) by means of HPLC-DAD and HPLC-MS analysis. In addition to previously reported secoiridoids (oleuropein, ligustaloside A, ligustaloside B, and ligstroside) four kaempferol glycosides (kaempferol 3-O-glucoside 7-O-rhamnoside, kaempferol 3, 7-O-dirhamnoside, kaempferol 3-O-rhamnoside, and kaempferol 3-O-glucoside) and two quercetin glycosides (quercetin 3-O-glucoside 7-O-rhamnoside and quercetin 3,7-O-dirhamnoside) were present in leaves of L. vulgare L. Although secoiridoids accounted for nearly the 76% of the total leaf polyphenols content (with ligustaloside A as the main component), kaempferol glycosides were also accumulated in the leaves of L. vulgare L. to a relatively high extent (23%). Contribution of quercetin derivatives was minor under our experimental conditions. Our findings suggest that flavonol glycosides may have a central role in both the ecology and the biology of L. vulgare L.

  HPLC-DAD; HPLC-MS; kaempferol glycosides; privet; quercetin glycosides; oleuropein; flavonoids

  NCBI PubMed ID: 10995320
  Publication DOI: 10.1021/jf9913256
  Journal NLM ID: 0374755
  Publisher: American Chemical Society
  Correspondence: tattini@ipsl.fi.cnr.it
  Institutions: Dipartimento di Scienze Farmaceutiche, Università di Firenze, Florence, Italy, Istituto sulla Propagazione delle SpeciesLegnose, Consiglio Nazionale delle Ricerche, Florence, Italy
  Methods: HPLC, extraction, HPLC-MS
  
   
  
  Ligustrum vulgare
  CSDB ID 67464 (all data & tools)
• Article ID: 12654
  Santos DYAC, Salatino MLF "Foliar flavonoids of Annonaceae from Brazil: taxonomic significance" - Phytochemistry 55(6) (2000) 567-573
  

  Foliar flavonoids of 31 species of the Annonaceae native to Brazil, amounting to 76 compounds, were isolated and identified. All phenols found were glycosides of either flavones (apigenin, scutellarein, hispidulin and luteolin) or flavonols (kaempferol, rhamnocitrin, 6-hydroxyrhamnocitrin, quercetin, isorhamnetin and rhamnetin), with the latter predominating. Some members of the tribe Bocageeae are distinctive for accumulating 6-oxygenated flavones and flavonols, in addition to 7-O-methylated flavonols, a feature possibly linked to the assumed advanced condition of the tribe within the family. Members of Duguetia stand out for the apparent absence of quercetin glycosides. Anaxagorea dolichocharpa seemingly lacks flavones and flavonols entirely. A UPGMA analysis based on the distribution of flavonoids does not group the analyzed species according to the available tribal division of the Annonaceae. However, several taxonomically meaningful groupings emerged through the multivariate analysis.

  Annonaceae; flavonoids; flavones; flavonols; UPGMA; chemotaxonomy

  NCBI PubMed ID: 11130666
  Publication DOI: 10.1016/s0031-9422(00)00227-2
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Correspondence: dyacsan@ib.usp.br
  Institutions: Institute of Biosciences, University of São Paulo, São Paulo, Brazil
  
   
  
  Annonaceae
  CSDB ID 67711 (all data & tools)