APIGETRIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C21H20O10
Molecular Weight	432.3775
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@@H](OC2=CC3=C(C(=O)C=C(O3)C4=CC=C(O)C=C4)C(O)=C2)[C@H](O)[C@@H](O)[C@@H]1O

InChI

InChIKey=KMOUJOKENFFTPU-QNDFHXLGSA-N

InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28336272 | https://www.ncbi.nlm.nih.gov/pubmed/28712867 | https://www.ncbi.nlm.nih.gov/pubmed/21480518

Apigetrin, a flavonoid glycoside, is present in a variety of medicinal plants with anti-inflammatory and ant-oxidant properties. It is isolated from various herbal medicines, including Matricaria chamomilla, Scutellaria baicalensis Georgi, Teucrium gnaphalodes and Stachys tibetica Vatke. Apigetrin may induce cancer cell differentiation – it could be one of the possible explanations of its antitumor effects. Inhibition of bright light-induced retinal oxidative stress and retinal inflammatory responses was associated with the retinal protection conferred by Apigetrin.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Oxidative Stress 160 Target ID: WP412 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28336272	Inhibitor 8297
cell differentiation 3 Target ID: GO:0030154 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21480518 \| https://www.ncbi.nlm.nih.gov/pubmed/22113421	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Retinal degenerative disorders 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28336272	Primary	Preclinical	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21480518 https://www.ncbi.nlm.nih.gov/pubmed/22113421	Primary	Basic research	Unknown Approved Use Unknown
Skin inflammation 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7683883	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Studies on the chemical constituents from Chrysanthemum morifolium Ramat].	2001 Aug	12776368
Simultaneous determination of seven compounds in snow lotus herb using high-performance liquid chromatography.	2003 May-Jun	12841951
Protective effect of flavonoids against aging- and lipopolysaccharide-induced cognitive impairment in mice.	2003 Oct	12928578
Phenolic compounds from the leaf extract of artichoke (Cynara scolymus L.) and their antimicrobial activities.	2004 Dec 1	15563206
Antioxidants and inhibitor of matrix metalloproteinase-1 expression from leaves of Zostera marina L.	2004 Feb	15022719
Supercritical carbon dioxide extraction of chamomile flowers: extraction efficiency, stability, and in-line inclusion of chamomile-carbon dioxide extract in beta-cyclodextrin.	2004 Jul-Aug	15311845
[Studies on the flavonoids in herb from Scutellaria barbata].	2004 Oct	15631081
Additional antiprotozoal constituents from Cuphea pinetorum, a plant used in Mayan traditional medicine to treat diarrhoea.	2005 Aug	16177979
Effects of compounds in leaves of Salix matsudana on arachidonic acid metabolism.	2005 Dec	16327246
Mechanisms of apigenin-7-glucoside as a hepatoprotective agent.	2005 Feb	15861781
[Studies on chemical constituents of Acroptilon repens].	2006 Nov	17285986
[Studies on flavones in of Lavandula augustifolia].	2007 May	17639984
Chemical constituents from the seeds of Trifolium alexandrinum.	2008 Dec	19085418
Simultaneous determination of nine major active compounds in Dracocephalum rupestre by HPLC.	2008 Dec 15	18930620
[Studies on chemical components of Lobelia chinensis].	2009 Feb	19445152
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.	2011 Dec 15	21872416

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 10, 50 or 200 mg/kg bw 30 min prior to bright light exposure

Route of Administration: Intraperitoneal

In Vitro Use Guide

RAW264.7 and THP1 cells were pre-treated with 50 or 100 uM Apigetrin for 1h, followed by LPS (100 ng/ml) treatment for another 24 h. Pro-inflammatory cytokines of TNF-α, IL-1β, COX2 and iNOS were dramatically induced by LPS, which were reversed by Apigetrin pre-treatment.

Name

Type

Language

APIGETRIN

Common Name

English

COSMOSIINE

Common Name

English

COSMOSIIN

Common Name

English

APIGENIN 7-GLUCOSIDE

Common Name

English

APIGENIN 7-O-GLUCOSIDE (CONSTITUENT OF CHAMOMILE) [DSC]

Common Name

English

COSMOSIDE

Common Name

English

7-(.BETA.-D-GLUCOPYRANOSYLOXY)-5-HYDROXY-2-(4-HYDROXYPHENYL)-4H-1-BENZOPYRAN-4-ONE

Common Name

English

NSC-407303

Code

English

COSMOSIOSIDE

Common Name

English

COSEMETIN

Common Name

English

4',5,7-TRIHYDROXYFLAVONE 7-GLUCOSIDE

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-5-HYDROXY-2-(4-HYDROXYPHENYL)-

Common Name

English

APIGENIN 7-O-.BETA.-D-GLUCOSIDE

Common Name

English

APIGETRIN [MI]

Common Name

English

7-O-(.BETA.-D-GLUCOSYL)APIGENIN

Common Name

English

APIGENIN-7-GLUCOSIDE [USP-RS]

Common Name

English

APIGENIN 7-O-.BETA.-D-GLUCOPYRANOSIDE

Common Name

English

Code System Code Type Description

ECHA (EC/EINECS)

209-430-5