Myricetin

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Myricetin
Myricetin.png
Identifiers
CAS number 529-44-2 YesY
PubChem 5281672
ChemSpider 4444991 YesY
DrugBank DB02375
ChEBI CHEBI:18152 N
ChEMBL CHEMBL164 YesY
Jmol-3D images Image 1
Properties
Molecular formula C15H10O8
Molar mass 318.24 g mol−1
Density 1.912 g/mL
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Myricetin is a naturally occurring flavonol, a flavonoid found in many grapes, berries, fruits, vegetables, herbs, as well as other plants. Walnuts are a rich dietary source. Trace amounts can be found as glycosides.[1] It is one of the phenolic compounds present in red wine.[2]

Pharmacological study[edit]

Myricetin has antioxidant properties.[citation needed] A Finnish study correlated high myricetin consumption with lowered rates of prostate cancer.[3] Another 8-year study found that intake of three flavonols (kaempferol, quercetin, and myricetin) were associated with a reduced incidence of pancreatic cancer in people who smoke.[4] Myricetin also reduces nocturnal levels of melatonin through the inhibition of serotonin N-acetyltransferase, potentially affecting circadian rhythm.[5] In vitro research suggests that myricetin in high concentrations can modify LDL cholesterol such that uptake by white blood cells is increased.[citation needed]

Metabolism[edit]

Glycosides[edit]

O-methylations[edit]

Combretol is the 3,7,3',4',5'-O-methylation of myricetin.

Laricitrin is formed from myricetin by the action of the enzyme myricetin O-methyltransferase.[6]

References[edit]

  1. ^ Miean, Koo Hui; Mohamed, Suhaila (2001). "Flavonoid (Myricetin, Quercetin, Kaempferol, Luteolin, and Apigenin) Content of Edible Tropical Plants". Journal of Agricultural and Food Chemistry 49 (6): 3106–12. doi:10.1021/jf000892m. PMID 11410016. 
  2. ^ Maggiolini, M; Recchia, AG; Bonofiglio, D; Catalano, S; Vivacqua, A; Carpino, A; Rago, V; Rossi, R; Andò, S (2005). "The red wine phenolics piceatannol and myricetin act as agonists for estrogen receptor in human breast cancer cells". Journal of Molecular Endocrinology 35 (2): 269–81. doi:10.1677/jme.1.01783. PMID 16216908. 
  3. ^ Knekt P, Kumpulainen J, Järvinen R, et al. (September 2002). "Flavonoid intake and risk of chronic diseases". Am. J. Clin. Nutr. 76 (3): 560–8. PMID 12198000. 
  4. ^ Nöthlings U, Murphy SP, Wilkens LR, Henderson BE, Kolonel LN (October 2007). "Flavonols and pancreatic cancer risk: the multiethnic cohort study". Am. J. Epidemiol. 166 (8): 924–31. doi:10.1093/aje/kwm172. PMID 17690219. 
  5. ^ Shin JC, Jung HY, Harikishore A, Kwon OD, Yoon HS, Kim KT, Choi BH (October 2013). "The flavonoid myricetin reduces nocturnal melatonin levels in the blood through the inhibition of serotonin N-acetyltransferase". Biochem Biophys Res Commun. 440 (2): 312–6. doi:10.1016/j.bbrc.2013.09.076. PMID 24076393. 
  6. ^ Syringetin biosynthetis pathway on metacyc.org