Miquelianin

Miquelianin
Chemical structure of miquelianin
Chemical structure of 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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
UNII
  • InChI=1S/C21H18O13/c22-7-4-10(25)12-11(5-7)32-17(6-1-2-8(23)9(24)3-6)18(13(12)26)33-21-16(29)14(27)15(28)19(34-21)20(30)31/h1-5,14-16,19,21-25,27-29H,(H,30,31)/t14-,15-,16+,19-,21+/m0/s1
    Key: DUBCCGAQYVUYEU-ZUGPOPFOSA-N
  • 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
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).

Miquelianin (quercetin 3-O-glucuronide) is a flavonol glucuronide, a type of phenolic compound present in wine, in species of St John's wort, like Hypericum hirsutum, in Nelumbo nucifera (Indian lotus) or in green beans.

It is also a rat plasma quercetin metabolite. It shows an antioxidant effect in human plasma. In vitro studies indicate that miquelianin is able to reach the central nervous system from the small intestine.

Formation

The enzyme glucuronosyltransferase converts quercetin to its glucuronide by adding a sugar acid at one of the hydroxy groups, with uridine diphosphate (UDP) as byproduct:

2D representation of the chemical structure of quercetin .
quercetin
+ UDP-glucuronate
 
 
 
Rightward reaction arrow with minor product(s) to top right
 
 
 
2D representation of the chemical structure of miquelianin .
miquelianin

See also

References

  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. Bibcode:1998JAFC...46..361G. 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 (1): 119–120. Bibcode:1988CNatC..24..119K. 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. Bibcode:2003PlMed..69.1013.. doi:10.1055/s-2003-45148. PMID 14735439.
  9. ↑ Wang, Zhenyu; Yang, Jinjin; Liu, Xiaozheng; Yu, Hongming; Dai, Xianjun (2026). "Dietary Quercetin 3- O -Glucuronide: Current Research on Its Extraction, Biosynthesis, Pharmacokinetics, Health Benefits, and Potential Food Applications". Journal of Agricultural and Food Chemistry. 74 (11): 9027–9043. doi:10.1021/acs.jafc.5c14773. PMID 41808541.