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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20O10
Molecular Weight 432.3783
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APIGETRIN

SMILES

c1cc(ccc1-c2cc(=O)c3c(cc(cc3o2)O[C@@]4([H])[C@@]([H])([C@]([H])([C@@]([H])([C@@]([H])(CO)O4)O)O)O)O)O

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 432.3783
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

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

Sources: DOI: 10.1039/CT9140501829

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
[Studies on the chemical constituents from Chrysanthemum morifolium Ramat].
2001 Aug
Phenolic glycosides from Phagnalon rupestre.
2002 Apr
Absorption and metabolism of flavonoids in the caco-2 cell culture model and a perused rat intestinal model.
2002 Apr
A novel cytotoxic C-methylated biflavone, taiwanhomoflavone-B from the twigs of Cephalotaxus wilsoniana.
2002 Dec
Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils.
2002 Feb
Simultaneous determination of seven compounds in snow lotus herb using high-performance liquid chromatography.
2003 May-Jun
Protective effect of flavonoids against aging- and lipopolysaccharide-induced cognitive impairment in mice.
2003 Oct
Phenolic compounds from the leaf extract of artichoke (Cynara scolymus L.) and their antimicrobial activities.
2004 Dec 1
Antioxidants and inhibitor of matrix metalloproteinase-1 expression from leaves of Zostera marina L.
2004 Feb
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
[Studies on the flavonoids in herb from Scutellaria barbata].
2004 Oct
Additional antiprotozoal constituents from Cuphea pinetorum, a plant used in Mayan traditional medicine to treat diarrhoea.
2005 Aug
Effects of compounds in leaves of Salix matsudana on arachidonic acid metabolism.
2005 Dec
Mechanisms of apigenin-7-glucoside as a hepatoprotective agent.
2005 Feb
Development of an HPLC-PAD-MS assay for the identification and quantification of major phenolic edelweiss (Leontopodium alpium Cass.) constituents.
2006 Sep-Oct
Two new phenolic constituents of Humulus japonicus and their cytotoxicity test in vitro.
2007 Nov
Antiproliferative and apoptotic effects of chamomile extract in various human cancer cells.
2007 Nov 14
Constituents of Ocimum sanctum with antistress activity.
2007 Sep
Achillea millefolium L. s.l. -- is the anti-inflammatory activity mediated by protease inhibition?
2007 Sep 5
Antioxidative activity of the flower of Torenia fournieri.
2008 Apr
[Studies on chemical constituents from Pteris multifida].
2008 Aug
Solid-liquid transfer of biophenols from olive leaves for the enrichment of edible oils by a dynamic ultrasound-assisted approach.
2008 Aug 27
Chemical constituents from the seeds of Trifolium alexandrinum.
2008 Dec
Simultaneous determination of nine major active compounds in Dracocephalum rupestre by HPLC.
2008 Dec 15
Chemical constituents from the leaves of Broussonetia papyrifera.
2008 Feb
[Studies on chemical constituents in Huangjuhua (flowers of Chrysanthemum morifolium)].
2008 Mar
[Flavones from flowers of Paulownia fortunei].
2008 Nov
A new acylated quercetin glycoside from the leaves of Stevia rebaudiana Bertoni.
2009
[Chemical constituents in Buddleja albiflora].
2009 Dec
[Studies on chemical components of Lobelia chinensis].
2009 Feb
[Studies on antibacterial constituents of Discocleidion rufescens (2)].
2009 Jun
Mesophyll distribution of 'antioxidant' flavonoid glycosides in Ligustrum vulgare leaves under contrasting sunlight irradiance.
2009 Oct
[Chemical constituents from Lagotis brevituba].
2010 Apr
[Study on the flavonoids constituents of Trachelospermum jasminoides].
2010 Jan
[Chemical constituents of Discocleidion rufescens].
2010 Jun
Secondary metabolites of Hypericum confertum and their possible chemotaxonomic significance.
2010 Jun
Phenolic compounds from Achillea millefolium L. and their bioactivity.
2011
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.
2011 Dec 15
Analysis of the erythroid differentiation effect of flavonoid apigenin on K562 human chronic leukemia cells.
2014 Sep 5
Patents

Sample Use Guides

Mice: 10, 50 or 200 mg/kg bw 30 min prior to bright light exposure
Route of Administration: Intraperitoneal
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 Sat Jun 26 09:36:09 UTC 2021
Edited
by admin
on Sat Jun 26 09:36:09 UTC 2021
Record UNII
7OF2S66PCH
Record Status Validated (UNII)
Record Version
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Name Type Language
APIGETRIN
MI  
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
Created by admin on Sat Jun 26 09:36:09 UTC 2021 , Edited by admin on Sat Jun 26 09:36:09 UTC 2021
PRIMARY
FDA UNII
7OF2S66PCH
Created by admin on Sat Jun 26 09:36:09 UTC 2021 , Edited by admin on Sat Jun 26 09:36:09 UTC 2021
PRIMARY
MERCK INDEX
M1988
Created by admin on Sat Jun 26 09:36:09 UTC 2021 , Edited by admin on Sat Jun 26 09:36:09 UTC 2021
PRIMARY Merck Index
USP_CATALOG
1040708
Created by admin on Sat Jun 26 09:36:09 UTC 2021 , Edited by admin on Sat Jun 26 09:36:09 UTC 2021
PRIMARY USP-RS
WIKIPEDIA
APIGETRIN
Created by admin on Sat Jun 26 09:36:09 UTC 2021 , Edited by admin on Sat Jun 26 09:36:09 UTC 2021
PRIMARY
PUBCHEM
5280704
Created by admin on Sat Jun 26 09:36:09 UTC 2021 , Edited by admin on Sat Jun 26 09:36:09 UTC 2021
PRIMARY
CAS
578-74-5
Created by admin on Sat Jun 26 09:36:09 UTC 2021 , Edited by admin on Sat Jun 26 09:36:09 UTC 2021
PRIMARY
Related Record Type Details
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