Quercetin 3-O-sulfate

Quercetin 3-O-sulfate
Chemical structure of
Names
IUPAC name
3′,4′,5,7-Tetrahydroxy-4-oxoflav-2-en-3-yl hydrogen sulfate
Systematic IUPAC name
2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4H-1-benzopyran-3-yl hydrogen sulfate
Other names
Quercetin 3-sulfate
Identifiers
CAS Number
  • 60889-05-6 checkY
  • 121241-74-5 (Potassium salt) checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:17730 checkY
ChemSpider
  • 4444061
PubChem CID
  • 5280362
UNII
  • XSS6HSA3AJ checkY
CompTox Dashboard (EPA)
  • DTXSID10209729 Edit this at Wikidata
InChI
  • InChI=1S/C15H10O10S/c16-7-4-10(19)12-11(5-7)24-14(6-1-2-8(17)9(18)3-6)15(13(12)20)25-26(21,22)23/h1-5,16-19H,(H,21,22,23)
    Key: DNAYVNOVGHZZLH-UHFFFAOYSA-N
  • InChI=1/C15H10O10S/c16-7-4-10(19)12-11(5-7)24-14(6-1-2-8(17)9(18)3-6)15(13(12)20)25-26(21,22)23/h1-5,16-19H,(H,21,22,23)
    Key: DNAYVNOVGHZZLH-UHFFFAOYAR
  • C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OS(=O)(=O)O)O)O
Properties
Chemical formula
 C15H10O10S
Molar mass 382.30 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references
Chemical compound

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 chlorifolia.[4] Quercetin-3,3'-bissulfate 7-sulfotransferase is an enzyme that uses 3'-phosphoadenylyl sulfate and quercetin 3,3'-bissulfate to produce adenosine 3',5'-bisphosphate and quercetin 3,7,3'-trissulfate. The enzyme can be found in Flaveria sp.

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. PMC 1061831. PMID 16666908.
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Flavonols and their conjugates
Backbone
Aglycones
Flavonols
Aglycones
Conjugates
Glycosides of herbacetin
Glycosides of kaempferol
  • Afzelin (Kaempferol 3-rhamnoside)
  • Astragalin (kaempferol 3-O-glucoside)
  • Kaempferitrin (kaempferol 3,7-dirhamnoside)
  • Juglanin (Kaempferol 3-O-arabinoside)
  • Kaempferol 3-alpha-L-arabinopyranoside
  • Kaempferol 3-alpha-D-arabinopyranoside
  • Kaempferol 7-alpha-L-arabinoside
  • 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 (kaempferol-3-O-robinoside-7-O-rhamnoside)
  • Kaempferol 3-O-rutinoside
  • Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
  • Trifolin (Kaempferol 3-O-beta-D-galactoside)
Glycosides of myricetin
Conjugates of quercetin
Sulfates
  • Quercetin 3-O-sulfate
  • Quercetin 3,3'-bissulfate
  • Quercetin 3,4'-bissulfate
Glycosides
O-Methylated flavonols
Aglycones
Glycosides
of isorhamnetin
  • Narcissin (Isorhamnetin 3-O-rutinoside)
  • Isorhamnetin 3-O-glucoside
  • Tamarixetin 7-rutinoside
other
  • Azalein (Azaleatin 3-O-α-L-rhamnoside)
  • Centaurein (Centaureidin 7-O-glucoside)
  • Eupalin (Eupalitin 3-0-rhamnoside)
  • Eupatolin (Eupatolitin 3-O-rhamnoside)
  • Jacein (Jaceidin 7-O-glucoside)
  • Patulitrin (Patuletin 7-O-glucoside
  • Xanthorhamnin (Rhamnetin glycoside)
Derivative flavonols
Aglycones
  • Noricaritin
  • Dihydronoricaritin
Glycosides
  • Amurensin
  • Icariin
  • Phelloside
  • Dihydrophelloside
  • Rutin S
Pyranoflavonols
Aglycones
Furanoflavonols
Aglycones
Glycosides
  • Pongamoside A, B and C
Semisynthetic
Glycosides


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