MYRICITRIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H20O12
Molecular Weight	464.3763
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@H]1O[C@@H](OC2=C(OC3=C(C(O)=CC(O)=C3)C2=O)C4=CC(O)=C(O)C(O)=C4)[C@H](O)[C@H](O)[C@H]1O

InChI

InChIKey=DCYOADKBABEMIQ-OWMUPTOHSA-N

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

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28751937 | https://www.ncbi.nlm.nih.gov/pubmed/21689712 | https://www.ncbi.nlm.nih.gov/pubmed/17070780

Myricitrin is a naturally occurring polyphenol hydroxy flavonoid. Myricitrin has a variety of beneficial properties, such as antiviral, antimicrobial, antinociceptive, and anticarcinogenic activities. In particular, myricitrin possesses stronger oxidative resistance and free radical scavenging activity than other flavonol rhamnosides or quercetin. Myricitrin showed antipsychotic-like effects in animal models at doses that did not induce catalepsy or alter locomotor activity, suggesting that myricitrin may be a potential drug treatment for the positive symptoms of schizophrenia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Catechol O-methyltransferase 21 Target ID: CHEMBL2023 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24716406	Inhibitor 8504	0.5 µM [Ki]
Oxidative Stress 162 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12972054	Inhibitor 8504
Protein kinase C alpha 21 Target ID: CHEMBL2567 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16260583 \| https://www.ncbi.nlm.nih.gov/pubmed/21689712	Inhibitor 8504
Protein kinase C epsilon 5 Target ID: CHEMBL4366 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21689712 \| https://www.ncbi.nlm.nih.gov/pubmed/16260583	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17467689 https://www.ncbi.nlm.nih.gov/pubmed/17070780	Primary	Preclinical	Unknown Approved Use Unknown
Schizophrenia 305 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21689712	Palliative	Preclinical	Unknown Approved Use Unknown
Anxiety 275 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19387830	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Myricitrin exhibits antioxidant, anti-inflammatory and antifibrotic activity in carbon tetrachloride-intoxicated mice.	2015-03-25	25656916
Protective effects of myricitrin against osteoporosis via reducing reactive oxygen species and bone-resorbing cytokines.	2014-11-01	25130202
Inhibitory effects of myricitrin on oxidative stress-induced endothelial damage and early atherosclerosis in ApoE-/- mice.	2013-08-15	23639522
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.	2011-12-15	21872416
[Studies on the chemical constituents of the root tube from Pteroxygonum giraldii].	2010-11	21434433
Assessment of DNA damage induced by extracts, fractions and isolated compounds of Davilla nitida and Davilla elliptica (Dilleniaceae).	2010-09-30	20692361
Gmelinoside I, a new flavonol glycoside from Limonium gmelinii.	2010-07	20734940
[Chemical constituents from Parthenocissus quinquefolia].	2010-06	20815210
Hexaoxygenated flavonoids from Pteroxygonum giraldii.	2010-02	20334131
Isolated flavonoids against mammary tumour cells LM2.	2009-03-28	19323263
[A new flavonol glycoside from Baeckea Frutescens L].	2008-10	19127867
An unusual C6-C6" linked flavonoid from Miconia cabucu (Melastomataceae).	2007-07	17540417
Constituents and antiulcer effect of Alchornea glandulosa: activation of cell proliferation in gastric mucosa during the healing process.	2007-03	17329837
Anti-human immunodeficiency virus-type 1 activity of constituents from Juglans mandshurica.	2002-08	12214852
Inhibitory activity of flavonoids and tannins against HIV-1 protease.	2000-09	10993207
Application of the electrotopological state index to QSAR analysis of flavone derivatives as HIV-1 integrase inhibitors.	1996-12	8987091
Inhibition of HIV-1 integrase by flavones, caffeic acid phenethyl ester (CAPE) and related compounds.	1994-08-03	7520698
Inhibition of HIV infection by flavanoids.	1993-10	8279812

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 5, 10, and 30 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

RAW264.7 cells were pretreated with 400 ug/ml myricitrin for 2 h or not and then were incubated with LPS (100 ng/ml) for 15 min. Noncytotoxic level of myricitrin inhibited p47phox which was transferred to the membrane and suppressed the interaction between p47phox and gp91phox.

Name

Type

Language

MYRICITRIN

Official Name

English

FEMA NO. 4491

Preferred Name

English

MYRICETIN 3-O-RHAMNOSIDE

Common Name

English

MYRICETIN 3-O-.ALPHA.-L-RHAMNOPYRANOSIDE

Common Name

English

3,3',4',5,5',7-HEXAHYDROXYFLAVONE, 3-RHAMNOSIDE

Common Name

English

MYRICITROSIDE

Common Name

English

MYRICETIN 3-O-.ALPHA.-L-RHAMNPYRONOSIDE

Common Name

English

MYRICITRINE

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-5,7-DIHYDROXY-2-(3,4,5-TRIHYDROXYPHENYL)-

Common Name

English

NSC-19803

Code

English

MYRICETIN 3-O-RHAMNOPYRANOSIDE

Common Name

English

Code System Code Type Description

CAS

17912-87-7