3-O-METHYLGALANGIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12O5
Molecular Weight	284.2635
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(OC2=CC(O)=CC(O)=C2C1=O)C3=CC=CC=C3

InChI

InChIKey=LYISDADPVOHJBJ-UHFFFAOYSA-N

InChI=1S/C16H12O5/c1-20-16-14(19)13-11(18)7-10(17)8-12(13)21-15(16)9-5-3-2-4-6-9/h2-8,17-18H,1H3

HIDE SMILES / InChI

Molecular Formula	C16H12O5
Molecular Weight	284.2635
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17516329 | https://www.ncbi.nlm.nih.gov/pubmed/19512999 | https://www.ncbi.nlm.nih.gov/pubmed/28394271 | https://www.ncbi.nlm.nih.gov/pubmed/12808299

3-O-methylgalangin is a naturally-occurring flavonoid. It is isolated and purified from the rhizomes of Alpinia officinarum and flowers of Helichrysum kraussii and H. odoratissimum. 3-O-methylgalangin exhibited significant anti-platelet aggregation activity in vitro. It has antioxidant activity. The higher antioxidant activity 3-O-methylgalangin can be attributed to the presence of C-2-C-3 unsaturation allowing the resonance stabilization of the formed radical. Flavonoids are known for their antimicrobial properties and 3-O-methylgalangin possess antibacterial activity against Gram-positive and Gram-negative bacteria also. 3-O-methylgalangin is an inhibitor of pancreatic lipase and it was reported that it lowered serum triglyceride level on corn oil-induced hyperlipidemic mice.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Pancreatic triacylglycerol lipase 12 Target ID: Q6P8U6 Gene ID: 69060.0 Gene Symbol: Pnlip Target Organism: Mus musculus (Mouse) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12808299	Inhibitor 8297
Oxidative Stress 160 Target ID: WP408 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24354185 \| https://www.ncbi.nlm.nih.gov/pubmed/19512999	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hyperlipidemia 80 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12808299	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Determination of the effect of 8-O-(2-methyl-2-butenoyl)-5,7-dihydroxy-3-methoxyflavone from Gnaphalium robustum on growth of Escherichia coli K-12 by optical density and electrical conductance measurements.	1994 Dec	7809218
Heliotropium huascoense resin exudate: chemical constituents and defensive properties.	2001 Sep	11575941
3-Methylethergalangin isolated from Alpinia officinarum inhibits pancreatic lipase.	2003 Jun	12808299
New dihydrochalcones and anti-platelet aggregation constituents from the leaves of Muntingia calabura.	2007 Jun	17516329
Chemical analysis of the resinous exudate isolated from Heliotropium taltalense and evaluation of the antioxidant activity of the phenolics components and the resin in homogeneous and heterogeneous systems.	2009 Jun 2	19512999
Antiinflammatory and antioxidant flavonoids from Helichrysum kraussii and H. odoratissimum flowers.	2013 Oct	24354185
Structure-Activity and Lipophilicity Relationships of Selected Antibacterial Natural Flavones and Flavanones of Chilean Flora.	2017 Apr 10	28394271

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 10 and 20 mg/kg for 3 days

Route of Administration: Oral

In Vitro Use Guide

To determine the effect of 3-O-methylgalangin on the growth curve of E. coli and B. subtilis, it was added to exponentially-growing cultures. 3-O-methylgalangin decreased the culture turbidity and cell viability of the Gram-positive bacteria Bacillus subtilis with the concentration 0.01 ug/ul. 3-O-methylgalangin showed a MICs that ranged from 0.25 to 1 ug/ml for tested Gram-negative bacteria (Enterobacter cloacae, Escherichia coli, Klebsiella pneumoniae, and Proteus mirabilis) and Gram-positive bacteria (Bacillus cereus, B. subtilis, B. coagulans, and Staphylococcus aureus).

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:50:58 GMT 2023` Edited by `admin` on `Fri Dec 15 18:50:58 GMT 2023`
Record UNII	02887TX99X
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

3-O-METHYLGALANGIN

Common Name

English

5,7-DIHYDROXY-3-METHOXYFLAVONE

Systematic Name

English

FLAVONE, 5,7-DIHYDROXY-3-METHOXY-

Systematic Name

English

GALANGIN 3-METHYL ETHER

Common Name

English

GALANGIN 3-O-METHYL ETHER

Common Name

English

3-METHYLGALANGIN

Common Name

English

4H-1-BENZOPYRAN-4-ONE, 5,7-DIHYDROXY-3-METHOXY-2-PHENYL-

Systematic Name

English

5,7-DIHYDROXY-3-METHOXY-2-PHENYL-4H-1-BENZOPYRAN-4-ONE

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID20216823