Quercetin 3-O-sulfate

Quercetin 3-O-sulfate
IUPAC name

[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] hydrogen sulfate
Other names

Quercetin 3-sulfate
Identifiers
CAS number 6089-05-6 Y, 121241-74-5 (Potassium salt) Y
PubChem 5280362
Jmol-3D images Image 1
Properties
Molecular formula C15H10O10S
Molar mass 382.3 g mol−1
Exact mass 381.999467 u
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Quercetin 3-sulfate is a plasma human metabolite of quercetin.[1][2][3] It is the sulfate conjugate of quercetin.

Quercetin-3-sulfate 3'-sulfotransferase is an enzyme that uses 3'-phosphoadenylyl sulfate and quercetin 3-sulfate to produce adenosine 3',5'-bisphosphate and quercetin 3,3'-bissulfate. Quercetin-3-sulfate 4'-sulfotransferase is an enzyme that uses 3'-phosphoadenylyl sulfate and quercetin 3-sulfate to produce adenosine 3',5'-bisphosphate and quercetin 3,4'-bissulfate. Both enzymes can be found in Flaveria chloraefolia.[4]

References

  1. ^ Human metabolism of dietary flavonoids: Identification of plasma metabolites of quercetin. Andrea J. Day, Fred Mellon, Denis Barron, Géraldine Sarrazin, Michael R.A. Morgan and Gary Williamson, Free Radical Research, 2001, Vol. 35, No. 6, pages 941-952, doi:10.1080/10715760100301441
  2. ^ Effect of quercetin conjugates on vascular permeability and expression of adhesion molecules. Mika Mochizuki, Katsuko Kajiya, Junji Terao, Kazuhiko Kaji, Shigenori Kumazawa, Tsutomu Nakayama and Kayoko Shimoi, BioFactors, Volume 22, Issue 1-4, pages 201–204, 2004, doi:10.1002/biof.5520220142
  3. ^ Metabolism of quercetin-7- and quercetin-3-glucuronides by an in vitro hepatic model: the role of human β-glucuronidase, sulfotransferase, catechol-O-methyltransferase and multi-resistant protein 2 (MRP2) in flavonoid metabolism. Karen A O’Leary, Andrea J Day, Paul W Needs, Fred A Mellon, Nora M O’Brien and Gary Williamson, Biochemical Pharmacology, Volume 65, Issue 3, 1 February 2003, pages 479-491,doi:10.1016/S0006-2952(02)01510-1
  4. ^ Varin L and Ibrahim RK (1989). "Partial purification and characterization of 3 flavonol-specific sulfotransferases from Flaveria chloraefolia". Plant Physiol. 90 (3): 977–981. doi:10.1104/pp.90.3.977. 
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