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Myricitrin

From Wikipedia, the free encyclopedia
Myricitrin
Myricitrin structure
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 InfoCard100.038.036Edit this at Wikidata
EC Number
  • 241-856-7
KEGG
UNII
  • InChI=1S/C21H20O12/c1-6-14(26)17(29)18(30)21(31-6)33-20-16(28)13-9(23)4-8(22)5-12(13)32-19(20)7-2-10(24)15(27)11(25)3-7/h2-6,14,17-18,21-27,29-30H,1H3/t6-,14-,17+,18+,21-/m0/s1
    Key: DCYOADKBABEMIQ-OWMUPTOHSA-N
  • 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 mass464.37 g/mol
Density1.882 g/mL
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
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Chemical compound

Myricitrin is a plant compound, the 3-O-α-L-rhamnopyranoside ofmyricetin.[1]

Occurrences

[edit]

It can be isolated from the root bark ofMyrica cerifera (bayberry, a small tree native to North America), inMyrica esculenta, inNymphaea lotus[2] andN. odorata, inChrysobalanus icaco[3] and inPolygonum aviculare.[4]

Myricitrin is used by several beetle species in their communication system.[5] These includePlagioderma versicolora,Agelastica coerulea,Atrachya menetrisi,Altica nipponica,Altica oleracea,Gastrolina depressa.

Pharmacology

[edit]

Myricitrin is anitric oxide andprotein kinase C inhibitor and exhibitsantipsychotic-like andanxiolytic-like effects inanimal models of psychosis and anxiety respectively.[6]

References

[edit]
  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.Bibcode:2003PChem..63..727E.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.
Flavonols and their conjugates
Backbone
Aglycones
Flavonols
Aglycones
Conjugates
Glycosides ofherbacetin
Glycosides ofkaempferol
Glycosides ofmyricetin
Conjugates ofquercetin
Sulfates
Glycosides
O-Methylated flavonols
Aglycones
Glycosides
of isorhamnetin
other
Derivative flavonols
Aglycones
Glycosides
Pyranoflavonols
Aglycones
Furanoflavonols
Aglycones
Glycosides
Semisynthetic
Glycosides
Retrieved from "https://en.wikipedia.org/w/index.php?title=Myricitrin&oldid=1311101990"
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