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 ; 121241-74-5 (Potassium salt) ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:17730 ;
ChemSpider	4444061;
PubChem CID	5280362;
UNII	XSS6HSA3AJ ;
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.

Biosynthesis and metabolism

Quercetin 3-O-sulfate is produced directly in the perennial herb Flaveria chlorifolia from the flavonol, quercetin, by the enzyme flavonol 3-sulfotransferase. This uses the cofactor 3'-phosphoadenosine-5'-phosphosulfate (PAPS) and gives adenosine 3',5'-bisphosphate as a byproduct.^[4]

quercetin

+ PAPS

quercetin 3-O-sulfate

+ adenosine 3',5'-
bisphosphate

In this plant, quercetin-3-sulfate 3'-sulfotransferase converts quercetin 3-O-sulfate to the 3,3' isomer of the bissulfate and quercetin-3-sulfate 4'-sulfotransferase gives the 3,4' isomer. Further reactions lead to compounds including quercetin 3,3',7-trissulfate.^[4]^[5]

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
1 2 Varin L, Ibrahim RK (July 1989). "Partial Purification and Characterization of Three Flavonol-Specific Sulfotransferases from Flaveria chlorifolia". Plant Physiology. 90 (3): 977–81. doi:10.1104/pp.90.3.977. PMC 1061831. PMID 16666908.
↑ Marsolais, Frédéric; Varin, Luc (1998). "Recent developments in the study of the structure-function relationship of flavonol sulfotransferases". Chemico-Biological Interactions. 109 (1–3): 117–122. doi:10.1016/s0009-2797(97)00125-7. PMID 9566738.

[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

[Varin-4] 1 2 Varin L, Ibrahim RK (July 1989). "Partial Purification and Characterization of Three Flavonol-Specific Sulfotransferases from Flaveria chlorifolia". Plant Physiology. 90 (3): 977–81. doi:10.1104/pp.90.3.977. PMC 1061831. PMID 16666908.

[5] Marsolais, Frédéric; Varin, Luc (1998). "Recent developments in the study of the structure-function relationship of flavonol sulfotransferases". Chemico-Biological Interactions. 109 (1–3): 117–122. doi:10.1016/s0009-2797(97)00125-7. PMID 9566738.

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