Myricitrin: Difference between revisions

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 401011564

| Name = Myricitrin

| ImageFile = Myricitrin.svg

| ImageSize = 250px

| ImageName = Myricitrin structure

| IUPACName = 3′,4′,5,5′,7-Pentahydroxy-3-(α-<small>L</small>-rhamnopyranosyloxy)flavone

| SystematicName = 5,7-Dihydroxy-3-{[(2''S'',3''R'',4''R'',5''R'',6''S'')-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)-4''H''-1-benzopyran-4-one

| OtherNames= Myricitroside<br>Myricitrine<br>Myricetrin<br>Myricetol 3-rhamnoside<br>Myricetin 3-O-rhamnoside<br>Myricetin 3-rhamnoside

|Section1={{Chembox Identifiers

| CASNo_Ref = {{cascite|correct|??}}

| CASNo = 17912-87-7

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 5Z0ZO61WPJ

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = C10108

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 4444992

| PubChem = 5281673

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 70082

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 454576

| 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

|Section2={{Chembox Properties

| Formula = C₂₁H₂₀O₁₂

| MolarMass = 464.37 g/mol

| Density = 1.882 g/mL

| MeltingPt =

| BoilingPt =

'''Myricitrin''' is a plant compound, the 3-O-α-L-rhamnopyranoside of [[myricetin]].<ref>{{Cite web|url=https://pubchem.ncbi.nlm.nih.gov/compound/5352000#section=Synonyms|title=Myricetin 3-rhamnoside}}</ref>

== 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]]''<ref>{{Cite journal|pmid=12842147|year=2003|last1=Elegami|first1=AA|last2=Bates|first2=C|last3=Gray|first3=AI|last4=MacKay|first4=SP|last5=Skellern|first5=GG|last6=Waigh|first6=RD|title=Two very unusual macrocyclic flavonoids from the water lily Nymphaea lotus|volume=63|issue=6|pages=727–31|journal=Phytochemistry|doi=10.1016/S0031-9422(03)00238-3}}</ref> and ''[[Nymphaea odorata|N. odorata]]'', in ''[[Chrysobalanus icaco]]''<ref>{{Cite journal|doi=10.1590/S0102-695X2006000300009|title=Determination of myricetin derivatives in Chrysobalanus icaco L. (Chrysobalanaceae)|year=2006|last1=Barbosa|first1=Wagner Luiz R.|last2=Peres|first2=Amiraldo|last3=Gallori|first3=Sandra|last4=Vincieri|first4=Franco F.|journal=Revista Brasileira de Farmacognosia|volume=16|issue=3|pages=333|doi-access=free}}</ref> and in ''[[Polygonum aviculare]]''.<ref>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}}</ref>

Myricitrin is used by several beetle species in their communication system.<ref>[http://www.pherobase.com/database/compound/compounds-detail-myricitrin.php Myricitrin on pherobase.com]</ref> 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.<ref>{{Cite journal|pmid=21689712|date=August 2011|last1=Pereira|first1=M|last2=Siba|first2=IP|last3=Chioca|first3=LR|last4=Correia|first4=D|last5=Vital|first5=MA|last6=Pizzolatti|first6=MG|last7=Santos|first7=AR|last8=Andreatini|first8=R|title=Myricitrin, a nitric oxide and protein kinase C inhibitor, exerts antipsychotic-like effects in animal models|volume=35|issue=7|pages=1636–44|doi=10.1016/j.pnpbp.2011.06.002|journal=Progress in Neuro-Psychopharmacology & Biological Psychiatry|doi-access=free}}</ref>

== References ==

[[Category:Flavonol rhamnosides]]