Miquelianin

Miquelianin
Names
	IUPAC name 3′,4′,5,7-Tetrahydroxy-4-oxoflav-2-en-3-yl β-D-glucopyranosiduronic acid
	Systematic IUPAC name (2S,3S,4S,5R,6S)-6-{[2-(3,4-Dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-1-benzopyran-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 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:66395 ;
ChEMBL	ChEMBL520546;
ChemSpider	4438874;
PubChem CID	5274585;
UNII	RY36PD0CQ2 ;
CompTox Dashboard (EPA)	DTXSID70945358 ;
	SMILES C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)C(=O)O)O)O)O)O)O;
Properties
Chemical formula	C21H18O13
Molar mass	478.362 g·mol−1
Density	1.961 g/mL
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 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]

References

^ Ghiselli, A.; Nardini, M.; Baldi, A.; Scaccini, C. (1998). "Antioxidant Activity of Different Phenolic Fractions Separated from an Italian Red Wine". Journal of Agricultural and Food Chemistry. 46 (2): 361–367. doi:10.1021/jf970486b. PMID 10554247.
^ Wei, Y.; Xie, Q.; Dong, W.; Ito, Y. (2009). "Separation of epigallocatechin and flavonoids from Hypericum perforatum L. By high-speed counter-current chromatography and preparative high-performance liquid chromatography". Journal of Chromatography A. 1216 (19): 4313–4318. doi:10.1016/j.chroma.2008.12.056. PMC 2777726. PMID 19150073.
^ Kitanov, G. M. (1988). "Miquelianin and other polyphenols from Hypericum hirsutum". Chemistry of Natural Compounds. 24: 119–120. doi:10.1007/BF00597593. S2CID 37846890.
^ Kashiwada, Y.; Aoshima, A.; Ikeshiro, Y.; Chen, Y. P.; Furukawa, H.; Itoigawa, M.; Fujioka, T.; Mihashi, K.; Cosentino, L. M.; Morris-Natschke, S. L.; Lee, K. H. (2005). "Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure–activity correlations with related alkaloids". Bioorganic & Medicinal Chemistry. 13 (2): 443–448. doi:10.1016/j.bmc.2004.10.020. PMID 15598565.
^ Plumb, G. W.; Price, K. R.; Williamson, G. (1999). "Antioxidant properties of flavonol glycosides from green beans". Redox Report. 4 (3): 123–127. doi:10.1179/135100099101534800. PMID 10496415.
^ Moon, J. H.; Tsushida, T.; Nakahara, K.; Terao, J. (2001). "Identification of quercetin 3-O-β-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin". Free Radical Biology and Medicine. 30 (11): 1274–1285. doi:10.1016/S0891-5849(01)00522-6. PMID 11368925.
^ Terao, J.; Yamaguchi, S.; Shirai, M.; Miyoshi, M.; Moon, J. H.; Oshima, S.; Inakuma, T.; Tsushida, T.; Kato, Y. (2001). "Protection by quercetin and quercetin 3-O-β-D-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein". Free Radical Research. 35 (6): 925–931. doi:10.1080/10715760100301421. PMID 11811543. S2CID 22095635.
^ Juergenliemk, G.; Boje, K.; Huewel, S.; Lohmann, C.; Galla, H. J.; Nahrstedt, A. (2003). "In Vitro Studies Indicate that Miquelianin (Quercetin 3-O-β-D-Glucuronopyranoside) is Able to Reach the CNS from the Small Intestine". Planta Medica. 69 (11): 1013–1017. doi:10.1055/s-2003-45148. PMID 14735439.

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[1] Ghiselli, A.; Nardini, M.; Baldi, A.; Scaccini, C. (1998). "Antioxidant Activity of Different Phenolic Fractions Separated from an Italian Red Wine". Journal of Agricultural and Food Chemistry. 46 (2): 361–367. doi:10.1021/jf970486b. PMID 10554247.

[2] Wei, Y.; Xie, Q.; Dong, W.; Ito, Y. (2009). "Separation of epigallocatechin and flavonoids from Hypericum perforatum L. By high-speed counter-current chromatography and preparative high-performance liquid chromatography". Journal of Chromatography A. 1216 (19): 4313–4318. doi:10.1016/j.chroma.2008.12.056. PMC 2777726. PMID 19150073.

[3] Kitanov, G. M. (1988). "Miquelianin and other polyphenols from Hypericum hirsutum". Chemistry of Natural Compounds. 24: 119–120. doi:10.1007/BF00597593. S2CID 37846890.

[4] Kashiwada, Y.; Aoshima, A.; Ikeshiro, Y.; Chen, Y. P.; Furukawa, H.; Itoigawa, M.; Fujioka, T.; Mihashi, K.; Cosentino, L. M.; Morris-Natschke, S. L.; Lee, K. H. (2005). "Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure–activity correlations with related alkaloids". Bioorganic & Medicinal Chemistry. 13 (2): 443–448. doi:10.1016/j.bmc.2004.10.020. PMID 15598565.

[5] Plumb, G. W.; Price, K. R.; Williamson, G. (1999). "Antioxidant properties of flavonol glycosides from green beans". Redox Report. 4 (3): 123–127. doi:10.1179/135100099101534800. PMID 10496415.

[6] Moon, J. H.; Tsushida, T.; Nakahara, K.; Terao, J. (2001). "Identification of quercetin 3-O-β-D-glucuronide as an antioxidative metabolite in rat plasma after oral administration of quercetin". Free Radical Biology and Medicine. 30 (11): 1274–1285. doi:10.1016/S0891-5849(01)00522-6. PMID 11368925.

[7] Terao, J.; Yamaguchi, S.; Shirai, M.; Miyoshi, M.; Moon, J. H.; Oshima, S.; Inakuma, T.; Tsushida, T.; Kato, Y. (2001). "Protection by quercetin and quercetin 3-O-β-D-glucuronide of peroxynitrite-induced antioxidant consumption in human plasma low-density lipoprotein". Free Radical Research. 35 (6): 925–931. doi:10.1080/10715760100301421. PMID 11811543. S2CID 22095635.

[8] Juergenliemk, G.; Boje, K.; Huewel, S.; Lohmann, C.; Galla, H. J.; Nahrstedt, A. (2003). "In Vitro Studies Indicate that Miquelianin (Quercetin 3-O-β-D-Glucuronopyranoside) is Able to Reach the CNS from the Small Intestine". Planta Medica. 69 (11): 1013–1017. doi:10.1055/s-2003-45148. PMID 14735439.

[1]

See also

References