From Wikipedia, the free encyclopedia
Myricitrin
Names
IUPAC name
3′,4′,5,5′,7-Pentahydroxy-3-(α-L -rhamnopyranosyloxy)flavone
Systematic IUPAC name
5,7-Dihydroxy-3-{[(2S ,3R ,4R ,5R ,6S )-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-4H -1-benzopyran-4-one
Other names
Myricitroside Myricitrine Myricetrin Myricetol 3-rhamnoside Myricetin 3-O-rhamnoside Myricetin 3-rhamnoside
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.038.036
KEGG
UNII
CC1C(C(C(C(O1)OC2=C(OC3=CC(=CC(=C3C2=O)O)O)C4=CC(=C(C(=C4)O)O)O)O)O)O
Properties
C21 H20 O12
Molar mass
464.37 g/mol
Density
1.882 g/mL
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Myricitrin is a plant compound, the 3-O-α-L-rhamnopyranoside of
myricetin .
[1]
Occurrences
It can be isolated from the root bark of
Myrica cerifera (Bayberry, a small tree native to North America), in
Myrica esculenta , in
Nymphaea lotus
[2] and
N. odorata , in
Chrysobalanus icaco
[3] and in
Polygonum aviculare .
[4]
Myricitrin is used by several beetle species in their communication system.
[5] These include
Plagioderma versicolora ,
Agelastica coerulea ,
Atrachya menetrisi ,
Altica nipponica ,
Altica oleracea ,
Gastrolina depressa .
Health effect
Myricitrin is a
nitric oxide and
protein kinase C inhibitor and exhibits antipsychotic-like and anxiolytic-like effects in animal models of psychosis and anxiety respectively.
[6]
References
^
"Myricetin 3-rhamnoside" .
^ Elegami, AA; Bates, C; Gray, AI; MacKay, SP; Skellern, GG; Waigh, RD (2003). "Two very unusual macrocyclic flavonoids from the water lily Nymphaea lotus". Phytochemistry . 63 (6): 727–31.
doi :
10.1016/S0031-9422(03)00238-3 .
PMID
12842147 .
^ Barbosa, Wagner Luiz R.; Peres, Amiraldo; Gallori, Sandra; Vincieri, Franco F. (2006).
"Determination of myricetin derivatives in Chrysobalanus icaco L. (Chrysobalanaceae)" . Revista Brasileira de Farmacognosia . 16 (3): 333.
doi :
10.1590/S0102-695X2006000300009 .
^ LC Method for Analysis of Three Flavonols in Rat Plasma and Urine after Oral Administration of Polygonum aviculare Extract. Fuquan Xu, Huashi Guan, Guoqiang Li and Hongbing Liu, Chromatographia, June 2009, Volume 69, Issue 11-12, pages 1251-1258,
doi :
10.1365/s10337-009-1088-x
^
Myricitrin on pherobase.com
^ Pereira, M; Siba, IP; Chioca, LR; Correia, D; Vital, MA; Pizzolatti, MG; Santos, AR; Andreatini, R (August 2011).
"Myricitrin, a nitric oxide and protein kinase C inhibitor, exerts antipsychotic-like effects in animal models" . Progress in Neuro-Psychopharmacology & Biological Psychiatry . 35 (7): 1636–44.
doi :
10.1016/j.pnpbp.2011.06.002 .
PMID
21689712 .
Flavonols and their conjugates
Backbone
Flavonols
O -Methylated flavonols
Derivative flavonols
Pyranoflavonols
Furanoflavonols
Semisynthetic