Quercetin 3-O-sulfate

Quercetin 3-O-sulfate
Names
	IUPAC name [2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl] hydrogen sulfate
	Other names Quercetin 3-sulfate
Identifiers
CAS Number	60889-05-6 ; 121241-74-5 (Potassium salt) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17730 ;
ChemSpider	4444061;
PubChem CID	5280362;
CompTox Dashboard (EPA)	DTXSID10209729 ;
	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;
	SMILES 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

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

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
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
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
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.

This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.