Myricitrin
Myricitrin structure
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.038.036 Edit this at Wikidata
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
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).
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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

  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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