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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H20O11
Molecular Weight 448.3769
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASTRAGALIN

SMILES

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

InChI

InChIKey=JPUKWEQWGBDDQB-QSOFNFLRSA-N
InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15-,17+,18-,21+/m1/s1

HIDE SMILES / InChI
Molecular Formula C21H20O11
Molecular Weight 448.3769
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Astragalin (kaempferol-3-O-glucoside) is extracted from many traditional herbs and medicinal plants. Astragalin extracted from persimmon and Rosa agrestis leaves has anti-atopic dermatitis and antioxidant activity. Several biological functions of astragalin have been studied, including inhibition of prostaglandin E2 production and angiotensin converting enzyme activity. It has been reported that astragalin has the inhibitory effect on NO and tumor necrosis factor (TNF)-α production in Raw 264.7 cells. Astragalin is a flavonoid with anti-inflammatory activity. It may be a promising cancer therapeutic drug and it has the potential of preventing atherosclerosis formation.

Originator

Nakabayashi, T.
1
Sources: DOI: 10.1271/bbb1924.19.104

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Activator
1447
Prostaglandin E2 production
1
Target ID: Prostaglandin E2 production
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Basic research
Unknown

Approved Use

Unknown
Preventing
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibitory effect of astragalin on expression of lipopolysaccharide-induced inflammatory mediators through NF-κB in macrophages.
2011-12
[Chemical constituents from aerial parts of Fallopia convolvulus].
2010-12
Cucullamide, a new putrescine bisamide from Amoora cucullata.
2010-08
[Flavonoids of Lysimachia paridiformis var. stenophylla].
2010-07
[Chemical constituents from Excoecaria acerifclia and their bioactivites].
2010-05
[Chemical constituents of Laggera pterodonta].
2010-03
Preparative isolation and purification of four flavonoids from the petals of Nelumbo nucifera by high-speed counter-current chromatography.
2009-12-19
[Chemical constituents of Viola tianshanica].
2009-11
Biological activity of a phloroglucinol glucoside derivative from Conyza aegyptiaca.
2009-10-02
Antiproliferative activity on human cancer cell lines after treatment with polyphenolic compounds isolated from Iris pseudopumila flowers and rhizomes.
2009-10-02
[Chemical constituents of flowers from Polygonum orientale].
2009-10
[HPLC fingerprint of chemical constituents of Flos Farfarae].
2009-05
[Studies on chemical constituents from leaves of Cassia alata].
2009-04
A new fungicidal lactone from Xylocarpus granatum (Meliaceae).
2009
Effects of compounds isolated from the fruits of Rumex japonicus on the protein glycation.
2008-12
[Flavones from flowers of Paulownia fortunei].
2008-11
Deep supercooling xylem parenchyma cells of katsura tree (Cercidiphyllum japonicum) contain flavonol glycosides exhibiting high anti-ice nucleation activity.
2008-09
Soil quality effects on Chenopodium album flavonoid content and antioxidant potential.
2008-07-09
Isolation of 5-hydroxypyrrolidin-2-one and other constituents from the young fronds of Pteridium aquilinum.
2008-07
Pharmacological basis for use of Pistacia integerrima leaves in hyperuricemia and gout.
2008-05-22
[Study on antioxidant activity of constituents from mulberry leaf].
2008-04
[Studies on chemical constituents of Arachniodes rhomboidea].
2008-03
[Chemical study on aerial parts of Ligusticum chuanxiong].
2007-07
[Studies on chemical constituents from leaves of Sapium sebiferum].
2007-06
Anti-stress constituents of Evolvulus alsinoides: an ayurvedic crude drug.
2007-05
The anti-thrombotic active constituents from Centella asiatica.
2007-05
A new amide from Thyrocarpus glochidiatus.
2006-10
Hepatoprotective activity of Schouwia thebica webb.
2006-09-01
Constituents from the leaves of Phellodendron amurense and their antioxidant activity.
2006-09
Chemical constituents from Mahkota dewa.
2006-06-07
Separation and determination of the effective components in the alabastrum of Edgeworthia chrysantha Lindl. by micellar electrokinetic capillary chromatography.
2006-03-18
[Studies on chemical constituents of cytotoxic fraction from leaves of Elaeagnus pungens].
2006-03
[Studies on chemical constituents from flowers of Apocynum venetum].
2005-09
[Applications of two-dimensional liquid chromatography coupled to mass spectrometry for the separation and identification of compounds in ginkgo biloba extracts].
2005-01
Glycosides from Grewia damine and Filicium decipiens.
2004-12
Depsides from the petals of Papaver rhoeas.
2004-04
[The preliminary studies on antioxidation of three kinds of flavoniods from Litsea coreana].
2004-02
[HPLC investigation of antioxidant components in Solidago herba].
2004
Simultaneous determination of seven compounds in snow lotus herb using high-performance liquid chromatography.
2003-07-05
Proposed active constituents of Dipladenia martiana.
2001-12
Evaluation of the antiviral activity of kaempferol and its glycosides against human cytomegalovirus.
2000-05
The anti-HIV activity and mechanisms of action of pure compounds isolated from Rosa damascena.
1996-12-04
Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase.
1995-04
Inhibition of HIV infection by flavanoids.
1993-10
Patents

Patents

JP2001190241A
1
JP2010239993A
1

Sample Use Guides

In Vivo Use Guide
Rat: 5 mg/kg and 15 mg/kg
Route of Administration: Intraperitoneal
In Vitro Use Guide
Peritoneal macrophages (3×10^4 cells/well) were pretreated with astragalin (100 ug/mL) for 1 h following stimulation of LPS (30 ng/mL) for 24 h. Astragalin completely inhibited NO synthesis by cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:59:44 GMT 2025
Edited
by admin
on Mon Mar 31 18:59:44 GMT 2025
Record UNII
APM8UQ3Z9O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(2S,3S)-DIHYROKAEMPFEROL 3-O-.BETA.-D-GLUCOSIDE
Preferred Name English
ASTRAGALIN
INCI  
Official Name English
3-GLUCOSYLKAEMPFEROL
Common Name English
KAEMPFEROL 3-O-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
4',5,7-TRIHYDROXYFLAVONE 3-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
KAEMPFEROL 3-O-.BETA.-GLUCOSIDE
Common Name English
ASTRAGALINE
Common Name English
KAEMPFEROL 3-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
KAEMPFEROL 3-O-GLUCOPYRANOSIDE
Common Name English
4H-1-BENZOPYRAN-4-ONE, 3-(.BETA.-D-GLUCOPYRANOSYLOXY)-5,7-DIHYDROXY-2-(4-HYDROXYPHENYL)-
Common Name English
KAEMPFEROL 3-O-GLUCOSIDE
Common Name English
KAEMPFEROL 3-O-.BETA.-D-GLUCOSIDE
Common Name English
KAEMPFEROL 3-O-GLUCOSIDE (CONSTITUENT OF GINKGO) [DSC]
Common Name English
KAEMPFEROL 3-.BETA.-D-GLUCOSIDE
Common Name English
Code System Code Type Description
FDA UNII
APM8UQ3Z9O
Created by admin on Mon Mar 31 18:59:44 GMT 2025 , Edited by admin on Mon Mar 31 18:59:44 GMT 2025
PRIMARY
PUBCHEM
5282102
Created by admin on Mon Mar 31 18:59:44 GMT 2025 , Edited by admin on Mon Mar 31 18:59:44 GMT 2025
PRIMARY
WIKIPEDIA
Astragalin
Created by admin on Mon Mar 31 18:59:44 GMT 2025 , Edited by admin on Mon Mar 31 18:59:44 GMT 2025
PRIMARY
EPA CompTox
DTXSID801017739
Created by admin on Mon Mar 31 18:59:44 GMT 2025 , Edited by admin on Mon Mar 31 18:59:44 GMT 2025
PRIMARY
CAS
480-10-4
Created by admin on Mon Mar 31 18:59:44 GMT 2025 , Edited by admin on Mon Mar 31 18:59:44 GMT 2025
PRIMARY
CHEBI
30200
Created by admin on Mon Mar 31 18:59:44 GMT 2025 , Edited by admin on Mon Mar 31 18:59:44 GMT 2025
PRIMARY
Related Record Type Details
ACAI
PARENT -> CONSTITUENT ALWAYS PRESENT
ORAC value expressed as umol TE/g for this compound is 15198.9 +- 502.6. ORAC is a chemical antioxidant assay that is based on the inhibition of the peroxyl-radical induced oxidation initiated by thermal decomposition of AAPH.
MORINGA OLEIFERA LEAF
CONSTITUENT ALWAYS PRESENT -> PARENT
EUPATORIUM PERFOLIATUM WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
GINKGO
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
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