Miquelianin

Miquelianin
IUPAC name

(2S,3S,4S,5R,6S)-6-[2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
Other names

Quercetin 3-O-glucuronide
Quercetol glucuronide
Quercetin 3-glucuronide
Quercetol 3-O-glucuronide
quercetin 3-O-β-D-glucuronopyranoside
Querciturone
Identifiers
CAS number 22688-79-5
PubChem 5274585
ChemSpider 4438874
ChEMBL CHEMBL520546
Jmol-3D images Image 1
Properties
Molecular formula C21H18O13
Molar mass 478.36 g mol−1
Exact mass 478.074741 u
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Miquelianin (quercetin 3-O-glucuronide) is a flavonol glucuronide, a type of phenolic compound present in wine[1], in species of St John's wort[2], like Hypericum hirsutum[3], in Nelumbo nucifera (Indian lotus)[4] or in green beans.[5]

It is also a rat plasma quercetin metabolite.[6] It shows an antioxidant effect in human plasma.[7] In vitro studies indicate that miquelianin is able to reach the central nervous system from the small intestine.[8]

See also

References

  1. ^ Antioxidant Activity of Different Phenolic Fractions Separated from an Italian Red Wine. Andrea Ghiselli, Mirella Nardini, Alessandro Baldi and Cristina Scaccini, J. Agric. Food Chem., 1998, 46 (2), pages 361–367, doi:10.1021/jf970486b
  2. ^ Separation of epigallocatechin and flavonoids from Hypericum perforatum L. by high-speed counter-current chromatography and preparative high-performance liquid chromatography. Yun Wei, Qianqian Xie,Wanting Dong and Yoichiro Ito, Journal of Chromatography A, 1216 (2009), pages 4313–4318, doi:10.1016/j.chroma.2008.12.056
  3. ^ Miquelianin and other polyphenols from Hypericum hirsutum. G. M. Kitanov, Chemistry of Natural Compounds, Volume 24, Number 1, pages 119-120, doi:10.1007/BF00597593
  4. ^ Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure-activity correlations with related alkaloids. Kashiwada Y, Aoshima A, Ikeshiro Y, Chen YP, Furukawa H, Itoigawa M, Fujioka T, Mihashi K, Cosentino LM, Morris-Natschke SL and Lee KH, Bioorg Med Chem., 2005 Jan 17, 13(2), pages 443-448, PubMed, doi:10.1016/j.bmc.2004.10.020
  5. ^ Antioxidant properties of flavonol glycosides from green beans. Plumb G.W., Price K.R. and Williamson G., Redox Report, Volume 4, Number 3, June 1999 , pages 123-127, doi:10.1179/135100099101534800
  6. ^ Identification of quercetin 3-O-beta-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin. Moon JH, Tsushida T, Nakahara K and Terao J, Free Radic Biol Med., 2001 Jun 1, volume 30 (11), pages 1274-1285, PubMed, doi:10.1016/S0891-5849(01)00522-6
  7. ^ Protection by quercetin and quercetin 3-O-beta-D-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein. Terao J, Yamaguchi S, Shirai M, Miyoshi M, Moon JH, Oshima S, Inakuma T, Tsushida T and Kato Y, Free Radic Res. 2001 Dec, 35(6), pages 925-931, PubMed, doi:10.1080/10715760100301421
  8. ^ In vitro studies indicate that miquelianin (quercetin 3-O-beta-D-glucuronopyranoside) is able to reach the CNS from the small intestine. Juergenliemk G, Boje K, Huewel S, Lohmann C, Galla HJ and Nahrstedt A, Planta Med. 2003 Nov, 69(11), pages 1013-1017, PubMed, doi:10.1055/s-2003-45148
Flavonols and their conjugates
Backbone
Aglycones
3-Hydroxyflavone (synthetic) and derivatives
Flavonols
Aglycones
Conjugates
Glycosides of herbacetin
Rhodionin | Rhodiosin
Glycosides of kaempferol
Afzelin (Kaempferol 3-rhamnoside) | Astragalin | Kaempferitrin | Juglanin (Kaempferol 3-O-arabinoside) | Kaempferol 3-alpha-L-arabinopyranoside | Kaempferol 3-alpha-D-arabinopyranoside | Kaempferol 7-alpha-L-arabinoside | Kaempferol 3-O-beta-D-galactoside | Kaempferol 7-O-glucoside | Kaempferol 3-lathyroside | Kaempferol 4'-rhamnoside | Kaempferol 5-rhamnoside | Kaempferol 7-rhamnoside | Kaempferol 7-O-alpha-L-rhamnofuranoside | Kaempferol 3-xyloside | Kaempferol 7-xyloside | Robinin | Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Glycosides of myricetin
Myricetin 3-O-rutinoside | Myricetin-3-O-neohesperidoside | Myricitrin
Conjugates of quercetin
Sulfates
Quercetin 3-O-sulfate | Quercetin 3,3'-bissulfate | Quercetin 3,4'-bissulfate
Glycosides
CTN-986 | Guaijaverin (quercetin 3-O-arabinoside) | Heliosin (Quercetin 3-digalactoside) | Hyperoside | Isoquercitin | Miquelianin | Quercetin-3-sophorodide | Quercitrin | Rutin | Spiraeoside
O-Methylated flavonols
Aglycones
Glycosides
Azalein | Centaurein | Eupalin | Eupatolin | Jacein | Patulitrin | Tamarixetin 7-rutinoside | Xanthorhamnin
Derivative flavonols
Aglycones
Noricaritin | Dihydronoricaritin
Glycosides
Amurensin | Icariin | Phelloside | Dihydrophelloside | Rutin S
Pyranoflavonols
Aglycones
Furanoflavonols
Aglycones
Glycosides
Pongamoside A, B and C
Semisynthetic
Glycosides