Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H10O5 |
Molecular Weight | 270.2369 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=CC(O)=C2C(=O)C(O)=C(OC2=C1)C3=CC=CC=C3
InChI
InChIKey=VCCRNZQBSJXYJD-UHFFFAOYSA-N
InChI=1S/C15H10O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,16-17,19H
Molecular Formula | C15H10O5 |
Molecular Weight | 270.2369 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Galangin is a flavanol that is found in high concentrations in Alpinia officinarum and Helichrysum aureonitens. It can also be found in the rhizome of Alpinia galanga and in propolis. Galangin has been shown to have antibacterial, antiviral, anticancer and neuroprotective properties in vitro and in animal models.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23143152
Curator's Comment: the referenced study was conducted on rat
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: P11387|||Q9UJN0 Gene ID: 7150.0 Gene Symbol: TOP1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26032076 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Antimicrobial constituents of Gomphrena martiana and Gomphrena boliviana. | 1992 Apr |
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Flavonoids induce apoptosis in human leukemia U937 cells through caspase- and caspase-calpain-dependent pathways. | 2004 |
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Antioxidant properties of complexes of flavonoids with metal ions. | 2004 |
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Validated methods for the quantification of biologically active constituents of poplar-type propolis. | 2004 Jul-Aug |
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Galangin expresses bactericidal activity against multiple-resistant bacteria: MRSA, Enterococcus spp. and Pseudomonas aeruginosa. | 2004 Nov 1 |
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Inhibitory effect of flavonoids on N-acetylation of 5-aminosalicylic acid in cultured rat hepatocytes. | 2004 Sep |
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Multiple-signaling pathways are involved in the inhibitory effects of galangin on urinary bladder contractility. | 2005 |
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Chemical compositions and antimicrobial activities of four different Anatolian propolis samples. | 2005 |
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The interaction of flavonoids with mitochondria: effects on energetic processes. | 2005 Apr 15 |
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The effect of quercetin and galangin on glutathione reductase. | 2005 Dec |
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Galangin protects pig detrusor nerves from repetitive field stimulation and anoxia/glucopenia injury. | 2005 Dec |
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Human cytomegalovirus-inhibitory flavonoids: studies on antiviral activity and mechanism of action. | 2005 Dec |
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Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2. | 2005 Feb 15 |
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Synthesis, spectral and electrochemical properties of Al(III) and Zn(II) complexes with flavonoids. | 2005 Jul |
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[Xanthine oxidase inhibitory activity and hypouricemia effect of propolis in rats]. | 2005 Mar |
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Flavonoids and tyrosine nitration: structure-activity relationship correlation with enthalpy of formation. | 2005 Mar |
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Production of cytokine and NO by RAW 264.7 macrophages and PBMC in vitro incubation with flavonoids. | 2005 May |
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Flavonoid galangin prevents smooth muscle fatigue of pig urinary bladder. | 2005 May |
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Antiherpetic activities of flavonoids against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in vitro. | 2005 Nov |
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The inhibitory effect of the flavonoid galangin on urinary bladder smooth muscle contractility is mediated in part by modulation of Ca2+ release from intracellular stores. | 2005 Oct |
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Detection of galangin-induced cytoplasmic membrane damage in Staphylococcus aureus by measuring potassium loss. | 2005 Oct 3 |
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Molecular targets of dietary polyphenols with anti-inflammatory properties. | 2005 Oct 31 |
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Growth of a human mammary tumor cell line is blocked by galangin, a naturally occurring bioflavonoid, and is accompanied by down-regulation of cyclins D3, E, and A. | 2006 |
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Dietary flavonoids attenuate tumor necrosis factor alpha-induced adhesion molecule expression in human aortic endothelial cells. Structure-function relationships and activity after first pass metabolism. | 2006 Dec 1 |
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Assessment of the antibacterial activity of galangin against 4-quinolone resistant strains of Staphylococcus aureus. | 2006 Feb |
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Use of the pig caecum model to mimic the human intestinal metabolism of hispidulin and related compounds. | 2006 Jan |
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Inhibitors from the rhizomes of Alpinia officinarum on production of nitric oxide in lipopolysaccharide-activated macrophages and the structural requirements of diarylheptanoids for the activity. | 2006 Jan 1 |
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Vasorelaxant effect of the flavonoid galangin on isolated rat thoracic aorta. | 2006 Jan 18 |
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Propolis from the northwest of Argentina as a source of antifungal principles. | 2006 Jul |
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Flavonoids protect human retinal pigment epithelial cells from oxidative-stress-induced death. | 2006 Jul |
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Antiparasitic activity of flavonoids and isoflavones against Cryptosporidium parvum and Encephalitozoon intestinalis. | 2006 Jun |
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Combinatorial biosynthesis of flavones and flavonols in Escherichia coli. | 2006 Jun |
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Inhibition of rat vas deferens contractions by flavonoids in-vitro. | 2006 Mar |
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Dietary flavonoids: effects on xenobiotic and carcinogen metabolism. | 2006 Mar |
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Chemical structure of flavonols in relation to modulation of angiogenesis and immune-endothelial cell adhesion. | 2006 Mar |
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Methylation protects dietary flavonoids from rapid hepatic metabolism. | 2006 May |
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TCDD-induced CYP1A1 expression, an index of dioxin toxicity, is suppressed by flavonoids permeating the human intestinal Caco-2 cell monolayers. | 2006 Nov 15 |
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Influence of galangin on HL-60 cell proliferation and survival. | 2006 Nov 8 |
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Mechanism and inhibitory effect of galangin and its flavonoid mixture from Alpinia officinarum on mushroom tyrosinase and B16 murine melanoma cells. | 2007 Aug |
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Mechanism of inhibition of human secretory phospholipase A2 by flavonoids: rationale for lead design. | 2007 Aug |
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Inhibition of horseradish peroxidase catalytic activity by new 3-phenylcoumarin derivatives: synthesis and structure-activity relationships. | 2007 Feb 1 |
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Esterase inhibition by grapefruit juice flavonoids leading to a new drug interaction. | 2007 Jul |
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Neutrophil effector functions triggered by Fc-gamma and/or complement receptors are dependent on B-ring hydroxylation pattern and physicochemical properties of flavonols. | 2007 Jul 4 |
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In vitro antimicrobial activity of propolis samples from different geographical origins against certain oral pathogens. | 2007 Jun-Aug |
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Flavonoids possess neuroprotective effects on cultured pheochromocytoma PC12 cells: a comparison of different flavonoids in activating estrogenic effect and in preventing beta-amyloid-induced cell death. | 2007 Mar 21 |
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[Quantitative analysis of galangin from propolis in different areas by HPLC]. | 2007 May |
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Elastase release by stimulated neutrophils inhibited by flavonoids: importance of the catechol group. | 2007 May-Jun |
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Studies on the interactions between some flavonols and cyclodextrins. | 2007 Nov 1 |
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Determination of flavonoid aglycones in several food samples by mixed micellar electrokinetic chromatography. | 2007 Oct |
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Optimisation of an extraction procedure and chemical characterisation of Croatian propolis tinctures. | 2007 Sep-Oct |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26156213
Curator's Comment: the referenced study was conducted on mice | the authors do not specify the route of administration
Specific-pathogen-free BALB/c mice aged 6-8 weeks were sensitized on days 0, 7 and 14 by intraperitoneal injection of 20 micro-g ovalbumin (OVA) emulsified in 2 mg of aluminum hydroxide gel in a total volume of 200 micro-L. Sensitised mice were exposed to aerosolized 5% OVA in sterile saline for 8 weeks beginning on day 16 for 30 min three times a week. Galangin at a dose of 0.1 or 0.5 mg/kg was administered 30 min before nebulized OVA.
Route of Administration:
Unknown
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10188874
Human MCF-7 cells were grown in RPMI-1640 media supplemented with 2 mM glutamine and 10% fetal bovine serum. Cells were sub-cultured weekly using 0.25% trypsin and 0.05% EDTA. All cultures were incubated at 37 deg-C under a 5% CO2 atmosphere. MCF-& cells in 175 cm^2 flasks were incubated in 12 mL of growth medium containing 0.1 micro-g/mL [3H]DMBA in the presence of DMSO, 1 micro-M galangin, or 10 micro-M galangin. After 24 hours, 1 mL of the medium was removed and extracted with 1 mL of ethyl acetate. [3H]DMBA was separated from metabolites and counted by scintilation.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:39:54 GMT 2023
by
admin
on
Fri Dec 15 16:39:54 GMT 2023
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Record UNII |
142FWE6ECS
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Record Status |
Validated (UNII)
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Record Version |
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548-83-4
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GALANGIN
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m5639
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208-960-4
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407229
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5281616
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DTXSID70203288
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142FWE6ECS
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C037032
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5262
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