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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 of APIGETRIN

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

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

Power, F.B.|Browning, H.
1
Sources: DOI: 10.1039/CT9140501829

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Activator
1447
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Analysis of the erythroid differentiation effect of flavonoid apigenin on K562 human chronic leukemia cells.
2014-09-05
Screening medicinal plants for the detection of novel antimalarial products applying the inhibition of β-hematin formation.
2011-12-15
Phenolic compounds from Achillea millefolium L. and their bioactivity.
2011
[Chemical constituents of Discocleidion rufescens].
2010-06
Secondary metabolites of Hypericum confertum and their possible chemotaxonomic significance.
2010-06
[Chemical constituents from Lagotis brevituba].
2010-04
[Study on the flavonoids constituents of Trachelospermum jasminoides].
2010-01
[Chemical constituents in Buddleja albiflora].
2009-12
Mesophyll distribution of 'antioxidant' flavonoid glycosides in Ligustrum vulgare leaves under contrasting sunlight irradiance.
2009-10
[Studies on antibacterial constituents of Discocleidion rufescens (2)].
2009-06
[Studies on chemical components of Lobelia chinensis].
2009-02
A new acylated quercetin glycoside from the leaves of Stevia rebaudiana Bertoni.
2009
Simultaneous determination of nine major active compounds in Dracocephalum rupestre by HPLC.
2008-12-15
Chemical constituents from the seeds of Trifolium alexandrinum.
2008-12
[Flavones from flowers of Paulownia fortunei].
2008-11
Solid-liquid transfer of biophenols from olive leaves for the enrichment of edible oils by a dynamic ultrasound-assisted approach.
2008-08-27
[Studies on chemical constituents from Pteris multifida].
2008-08
Antioxidative activity of the flower of Torenia fournieri.
2008-04
[Studies on chemical constituents in Huangjuhua (flowers of Chrysanthemum morifolium)].
2008-03
Chemical constituents from the leaves of Broussonetia papyrifera.
2008-02
Antiproliferative and apoptotic effects of chamomile extract in various human cancer cells.
2007-11-14
Two new phenolic constituents of Humulus japonicus and their cytotoxicity test in vitro.
2007-11
Achillea millefolium L. s.l. -- is the anti-inflammatory activity mediated by protease inhibition?
2007-09-05
Constituents of Ocimum sanctum with antistress activity.
2007-09
[Studies on flavones in of Lavandula augustifolia].
2007-05
In vitro estrogenic activity of Achillea millefolium L.
2007-02
Superheated liquid extraction of oleuropein and related biophenols from olive leaves.
2006-12-15
[Studies on chemical constituents of Acroptilon repens].
2006-11
[Determination of main flavone glycosides in Flos Chrysanthemi and observation of factors influenced contents].
2006-11
Development of an HPLC-PAD-MS assay for the identification and quantification of major phenolic edelweiss (Leontopodium alpium Cass.) constituents.
2006-10-06
Effects of compounds in leaves of Salix matsudana on arachidonic acid metabolism.
2005-12
Additional antiprotozoal constituents from Cuphea pinetorum, a plant used in Mayan traditional medicine to treat diarrhoea.
2005-08
Mechanisms of apigenin-7-glucoside as a hepatoprotective agent.
2005-02
Phenolic compounds from the leaf extract of artichoke (Cynara scolymus L.) and their antimicrobial activities.
2004-12-01
[Studies on the flavonoids in herb from Scutellaria barbata].
2004-10
Supercritical carbon dioxide extraction of chamomile flowers: extraction efficiency, stability, and in-line inclusion of chamomile-carbon dioxide extract in beta-cyclodextrin.
2004-08-18
Antioxidants and inhibitor of matrix metalloproteinase-1 expression from leaves of Zostera marina L.
2004-02
Protective effect of flavonoids against aging- and lipopolysaccharide-induced cognitive impairment in mice.
2003-10
Simultaneous determination of seven compounds in snow lotus herb using high-performance liquid chromatography.
2003-07-05
Calmodulin inhibitors from Leucophyllum ambiguum.
2003-02
A novel cytotoxic C-methylated biflavone, taiwanhomoflavone-B from the twigs of Cephalotaxus wilsoniana.
2002-12
Phenolic glycosides from Phagnalon rupestre.
2002-04
Absorption and metabolism of flavonoids in the caco-2 cell culture model and a perused rat intestinal model.
2002-04
Effect of six flavonoid compounds from Ixeris sonchifolia on stimulus-induced superoxide generation and tyrosyl phosphorylation in human neutrophils.
2002-02
[Studies on the chemical constituents from Chrysanthemum morifolium Ramat].
2001-08
Patents

Patents

20010047032
25
20040081681
1

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 Mon Mar 31 19:04:21 GMT 2025
Edited
by admin
on Mon Mar 31 19:04:21 GMT 2025
Record UNII
7OF2S66PCH
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APIGETRIN
MI  
Common Name English
NSC-407303
Preferred 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
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 Mon Mar 31 19:04:21 GMT 2025 , Edited by admin on Mon Mar 31 19:04:21 GMT 2025
PRIMARY
NSC
407303
Created by admin on Mon Mar 31 19:04:21 GMT 2025 , Edited by admin on Mon Mar 31 19:04:21 GMT 2025
PRIMARY
FDA UNII
7OF2S66PCH
Created by admin on Mon Mar 31 19:04:21 GMT 2025 , Edited by admin on Mon Mar 31 19:04:21 GMT 2025
PRIMARY
CHEBI
16778
Created by admin on Mon Mar 31 19:04:21 GMT 2025 , Edited by admin on Mon Mar 31 19:04:21 GMT 2025
PRIMARY
MERCK INDEX
m1988
Created by admin on Mon Mar 31 19:04:21 GMT 2025 , Edited by admin on Mon Mar 31 19:04:21 GMT 2025
PRIMARY Merck Index
EPA CompTox
DTXSID401028774
Created by admin on Mon Mar 31 19:04:21 GMT 2025 , Edited by admin on Mon Mar 31 19:04:21 GMT 2025
PRIMARY
WIKIPEDIA
APIGETRIN
Created by admin on Mon Mar 31 19:04:21 GMT 2025 , Edited by admin on Mon Mar 31 19:04:21 GMT 2025
PRIMARY
RS_ITEM_NUM
1040708
Created by admin on Mon Mar 31 19:04:21 GMT 2025 , Edited by admin on Mon Mar 31 19:04:21 GMT 2025
PRIMARY
PUBCHEM
5280704
Created by admin on Mon Mar 31 19:04:21 GMT 2025 , Edited by admin on Mon Mar 31 19:04:21 GMT 2025
PRIMARY
CAS
578-74-5
Created by admin on Mon Mar 31 19:04:21 GMT 2025 , Edited by admin on Mon Mar 31 19:04:21 GMT 2025
PRIMARY
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