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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:70082^N
ChEMBL	ChEMBL454576^N
ChemSpider	4444992^N
ECHA InfoCard	100.038.036
KEGG	C10108^Y
PubChem CID	5281673
UNII	5Z0ZO61WPJ^Y
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). N verify (what is ^YN ?) Infobox references

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

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin
Rhodiosin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Betmidin (Myricetin 3-O-arabinoside)
Myricetin 3-O-rutinoside
Myricetin-3-O-neohesperidoside
Myricitrin (Myricetin 3-O-rhamnoside)

Conjugates of quercetin

Sulfates

Quercetin 3-O-sulfate
Quercetin 3,3'-bissulfate
Quercetin 3,4'-bissulfate

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)