Myricitrin

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
CAS Number	17912-87-7 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:70082 ;
ChEMBL	ChEMBL454576 ;
ChemSpider	4444992 ;
ECHA InfoCard	100.038.036
KEGG	C10108 ;
PubChem CID	5281673;
UNII	5Z0ZO61WPJ ;
CompTox Dashboard (EPA)	DTXSID40170771 ;
	SMILES 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
Chemical formula	C21H20O12
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). verify (what is ?) Infobox references

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.

[1] "Myricetin 3-rhamnoside".

[2] 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.

[3] 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.

[4] 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

[5] Myricitrin on pherobase.com

[6] 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.

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