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

Molecular Formula	C21H20O10
Molecular Weight	432.3775
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Phenolic glycosides from Phagnalon rupestre.	2002 Apr	11937166
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
Superheated liquid extraction of oleuropein and related biophenols from olive leaves.	2006 Dec 15	17045596
[Determination of main flavone glycosides in Flos Chrysanthemi and observation of factors influenced contents].	2006 Nov	17260789
Development of an HPLC-PAD-MS assay for the identification and quantification of major phenolic edelweiss (Leontopodium alpium Cass.) constituents.	2006 Sep-Oct	17019930
In vitro estrogenic activity of Achillea millefolium L.	2007 Feb	16860978
[Studies on flavones in of Lavandula augustifolia].	2007 May	17639984
Achillea millefolium L. s.l. -- is the anti-inflammatory activity mediated by protease inhibition?	2007 Sep 5	17689902
Chemical constituents from the seeds of Trifolium alexandrinum.	2008 Dec	19085418
[Studies on chemical constituents in Huangjuhua (flowers of Chrysanthemum morifolium)].	2008 Mar	18536375
A new acylated quercetin glycoside from the leaves of Stevia rebaudiana Bertoni.	2009	19809909
[Chemical constituents in Buddleja albiflora].	2009 Dec	20222420
[Chemical constituents of Discocleidion rufescens].	2010 Jun	20822016
Secondary metabolites of Hypericum confertum and their possible chemotaxonomic significance.	2010 Jun	20614818
Analysis of the erythroid differentiation effect of flavonoid apigenin on K562 human chronic leukemia cells.	2014 Sep 5	25058688

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:08:19 GMT 2023` Edited by `admin` on `Fri Dec 15 18:08:19 GMT 2023`
Record UNII	7OF2S66PCH
Record Status	`Validated (UNII)`
Record Version

Download

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