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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

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

Sources: DOI: 10.1271/bbb1924.19.104

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Inhibition of HIV infection by flavanoids.
1993 Oct
Inhibitory effects of Egyptian folk medicines on human immunodeficiency virus (HIV) reverse transcriptase.
1995 Apr
The anti-HIV activity and mechanisms of action of pure compounds isolated from Rosa damascena.
1996 Dec 4
Evaluation of the antiviral activity of kaempferol and its glycosides against human cytomegalovirus.
2000 May
Proposed active constituents of Dipladenia martiana.
2001 Dec
Simultaneous determination of seven compounds in snow lotus herb using high-performance liquid chromatography.
2003 May-Jun
Glycosides from Grewia damine and Filicium decipiens.
2004 Dec
[The preliminary studies on antioxidation of three kinds of flavoniods from Litsea coreana].
2004 Feb
[Applications of two-dimensional liquid chromatography coupled to mass spectrometry for the separation and identification of compounds in ginkgo biloba extracts].
2005 Jan
[Studies on chemical constituents from flowers of Apocynum venetum].
2005 Sep
Chemical constituents from Mahkota dewa.
2006 Jan-Mar
[Studies on chemical constituents of cytotoxic fraction from leaves of Elaeagnus pungens].
2006 Mar
A new amide from Thyrocarpus glochidiatus.
2006 Oct
Constituents from the leaves of Phellodendron amurense and their antioxidant activity.
2006 Sep
Hepatoprotective activity of Schouwia thebica webb.
2006 Sep 1
[Chemical study on aerial parts of Ligusticum chuanxiong].
2007 Jul
[Studies on chemical constituents from leaves of Sapium sebiferum].
2007 Jun
Anti-stress constituents of Evolvulus alsinoides: an ayurvedic crude drug.
2007 May
The anti-thrombotic active constituents from Centella asiatica.
2007 May
[Study on antioxidant activity of constituents from mulberry leaf].
2008 Apr
Soil quality effects on Chenopodium album flavonoid content and antioxidant potential.
2008 Jul 9
[Studies on chemical constituents of Arachniodes rhomboidea].
2008 Mar
Pharmacological basis for use of Pistacia integerrima leaves in hyperuricemia and gout.
2008 May 22
A new fungicidal lactone from Xylocarpus granatum (Meliaceae).
2009
Biological activity of a phloroglucinol glucoside derivative from Conyza aegyptiaca.
2009 Jul-Aug
[HPLC fingerprint of chemical constituents of Flos Farfarae].
2009 May
[Chemical constituents of Viola tianshanica].
2009 Nov
[Chemical constituents of flowers from Polygonum orientale].
2009 Oct
[Chemical constituents of Laggera pterodonta].
2010 Mar
Preparative isolation and purification of four flavonoids from the petals of Nelumbo nucifera by high-speed counter-current chromatography.
2010 May-Jun
Inhibitory effect of astragalin on expression of lipopolysaccharide-induced inflammatory mediators through NF-κB in macrophages.
2011 Dec
Patents

Sample Use Guides

Rat: 5 mg/kg and 15 mg/kg
Route of Administration: Intraperitoneal
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 Thu Jul 06 01:16:23 UTC 2023
Edited
by admin
on Thu Jul 06 01:16:23 UTC 2023
Record UNII
APM8UQ3Z9O
Record Status Validated (UNII)
Record Version
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Name Type Language
ASTRAGALIN
Common 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
(2S,3S)-DIHYROKAEMPFEROL 3-O-.BETA.-D-GLUCOSIDE
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 Thu Jul 06 01:16:23 UTC 2023 , Edited by admin on Thu Jul 06 01:16:23 UTC 2023
PRIMARY
PUBCHEM
5282102
Created by admin on Thu Jul 06 01:16:23 UTC 2023 , Edited by admin on Thu Jul 06 01:16:23 UTC 2023
PRIMARY
WIKIPEDIA
Astragalin
Created by admin on Thu Jul 06 01:16:23 UTC 2023 , Edited by admin on Thu Jul 06 01:16:23 UTC 2023
PRIMARY
EPA CompTox
DTXSID801017739
Created by admin on Thu Jul 06 01:16:23 UTC 2023 , Edited by admin on Thu Jul 06 01:16:23 UTC 2023
PRIMARY
CAS
480-10-4
Created by admin on Thu Jul 06 01:16:23 UTC 2023 , Edited by admin on Thu Jul 06 01:16:23 UTC 2023
PRIMARY
CHEBI
30200
Created by admin on Thu Jul 06 01:16:23 UTC 2023 , Edited by admin on Thu Jul 06 01:16:23 UTC 2023
PRIMARY
Related Record Type Details
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.
CONSTITUENT ALWAYS PRESENT -> PARENT
Repeated chromatography of the n-BuOH soluble fraction yielded this flavonoid glucoside. Other studies have shown this compound to be antihypertensive.
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT