Chemistry:Miquelianin

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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]

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:[9]

  1. REDIRECT Template:Chemical reaction

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. doi:10.1021/jf970486b. PMID 10554247. Bibcode: 1998JAFC...46..361G. 
  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. PMID 19150073. 
  3. ↑ Kitanov, G. M. (1988). "Miquelianin and other polyphenols from Hypericum hirsutum". Chemistry of Natural Compounds 24 (1): 119–120. doi:10.1007/BF00597593. Bibcode: 1988CNatC..24..119K. 
  4. ↑ Kashiwada, Y.; Aoshima, A.; Ikeshiro, Y.; Chen, Y. P.; Furukawa, H.; Itoigawa, M.; Fujioka, T.; Mihashi, K. et al. (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. et al. (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. 
  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. Bibcode: 2003PlMed..69.1013.. 
  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. 



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