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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
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Activator
1430
Prostaglandin E2 production
1
Target ID: Prostaglandin E2 production
Inhibitor
8297
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
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
Simultaneous determination of seven compounds in snow lotus herb using high-performance liquid chromatography.
2003 May-Jun
[Studies on chemical constituents of cytotoxic fraction from leaves of Elaeagnus pungens].
2006 Mar
[Studies on chemical constituents from leaves of Sapium sebiferum].
2007 Jun
Anti-stress constituents of Evolvulus alsinoides: an ayurvedic crude drug.
2007 May
Effects of compounds isolated from the fruits of Rumex japonicus on the protein glycation.
2008 Dec
[Studies on chemical constituents of Arachniodes rhomboidea].
2008 Mar
[Flavonoids of Lysimachia paridiformis var. stenophylla].
2010 Jul
Preparative isolation and purification of four flavonoids from the petals of Nelumbo nucifera by high-speed counter-current chromatography.
2010 May-Jun
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 Fri Dec 15 17:59:19 GMT 2023
Edited
by admin
on Fri Dec 15 17:59:19 GMT 2023
Record UNII
APM8UQ3Z9O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
(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 Fri Dec 15 17:59:19 GMT 2023 , Edited by admin on Fri Dec 15 17:59:19 GMT 2023
PRIMARY
PUBCHEM
5282102
Created by admin on Fri Dec 15 17:59:19 GMT 2023 , Edited by admin on Fri Dec 15 17:59:19 GMT 2023
PRIMARY
WIKIPEDIA
Astragalin
Created by admin on Fri Dec 15 17:59:19 GMT 2023 , Edited by admin on Fri Dec 15 17:59:19 GMT 2023
PRIMARY
EPA CompTox
DTXSID801017739
Created by admin on Fri Dec 15 17:59:19 GMT 2023 , Edited by admin on Fri Dec 15 17:59:19 GMT 2023
PRIMARY
CAS
480-10-4
Created by admin on Fri Dec 15 17:59:19 GMT 2023 , Edited by admin on Fri Dec 15 17:59:19 GMT 2023
PRIMARY
CHEBI
30200
Created by admin on Fri Dec 15 17:59:19 GMT 2023 , Edited by admin on Fri Dec 15 17:59:19 GMT 2023
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
Repeated chromatography of the n-BuOH soluble fraction yielded this flavonoid glucoside. Other studies have shown this compound to be antihypertensive.
EUPATORIUM PERFOLIATUM WHOLE
PARENT -> CONSTITUENT ALWAYS PRESENT
GINKGO
PARENT -> CONSTITUENT ALWAYS PRESENT
NIH
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