Galangin

Galangin
Names
	IUPAC name 3,5,7-Trihydroxyflavone
	Systematic IUPAC name 3,5,7-Trihydroxy-2-phenyl-4H-1-benzopyran-4-one
	Other names Norizalpinin; 3,5,7-triOH-Flavone
Identifiers
CAS Number	548-83-4;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:5262;
ChEMBL	ChEMBL309490;
ChemSpider	4444935;
ECHA InfoCard	100.008.147
IUPHAR/BPS	410;
KEGG	C10044;
PubChemCID	5281616;
UNII	142FWE6ECS;
CompTox Dashboard(EPA)	DTXSID70203288;
	InChI 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 Key: VCCRNZQBSJXYJD-UHFFFAOYSA-N; InChI=1/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 Key: VCCRNZQBSJXYJD-UHFFFAOYAC;
	SMILES O=C1c3c(O/C(=C1/O)c2ccccc2)cc(O)cc3O;
Properties
Chemical formula	C15H10O5
Molar mass	270.240g·mol−1
Density	1.579 g/mL
Melting point	214 to 215 °C (417 to 419 °F; 487 to 488 K)
	Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa). verify(what is?) Infobox references

Galanginis aflavonol,a type offlavonoid.

Occurrence[edit]

Galangin is found in high concentrations in plants likeAlpinia officinarum(lesser galangal)^[1]andHelichrysum aureonitens.^[2]It is also found in therhizomeofAlpinia galanga^[3]and inpropolis.^[4]

Biological activities[edit]

Galangin has been shown to havein vitroantibacterial^[5]^[6]andantiviralactivity.^[7]It also inhibits the growth ofbreast tumorcellsin vitro.^[8]^[9]

References[edit]

^Ciolino, H. P.; Yeh, G. C. (1999)."The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor".British Journal of Cancer.79(9/10): 1340–1346.doi:10.1038/sj.bjc.6690216.PMC2362711.PMID 10188874.
^Afolayan AJ, Meyer JJ (1997). "The antimicrobial activity of 3,5,7-trihydroxyflavone isolated from the shoots of Helichrysum aureonitens".Journal of Ethnopharmacology.57(3): 177–181.doi:10.1016/s0378-8741(97)00065-2.PMID 9292410.
^Kaur, A.; Singh, R.; Dey, C. S.; Sharma, S. S.; Bhutani, K. K.; Singh, I. P. (2010)."Antileishmanial phenylpropanoids fromAlpinia galanga(Linn.) Willd "(PDF).Indian Journal of Experimental Biology.48(3): 314–317.PMID 21046987.
^Tosi, E; Re, E; Ortega, M; Cazzoli, A (2007). "Food preservative based on propolis: Bacteriostatic activity of propolis polyphenols and flavonoids upon Escherichia coli".Food Chemistry.104(3): 1025–1029.doi:10.1016/j.foodchem.2007.01.011.
^Cushnie TP, Lamb AJ (2006). "Assessment of the antibacterial activity of galangin against 4-quinolone resistant strains of Staphylococcus aureus".Phytomedicine.13(3): 187–191.doi:10.1016/j.phymed.2004.07.003.PMID 16428027.
^Cushnie TP, Lamb AJ (2005). "Detection of galangin-induced cytoplasmic membrane damage in Staphylococcus aureus by measuring potassium loss".Journal of Ethnopharmacology.101(1–3): 243–248.doi:10.1016/j.jep.2005.04.014.PMID 15985350.
^Afolayan AJ, Meyer JJ, Taylor MB, Erasmus D (1997). "Antiviral activity of galangin isolated from the aerial parts of Helichrysum aureonitens".Journal of Ethnopharmacology.56(2): 165–169.doi:10.1016/s0378-8741(97)01514-6.PMID 917497.
^So, F. V.; Guthrie, N.; Chambers, A. F.; Moussa, M.; Carroll, K. K. (1996). "Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices".Nutrition and Cancer.26(2): 167–181.doi:10.1080/01635589609514473.PMID 8875554.
^So, F.; Guthrie, N.; Chambers, A. F.; Carroll, K. K. (1997). "Inhibition of proliferation of estrogen receptor-positive MCF-7 human breast cancer cells by flavonoids in the presence and absence of excess estrogen".Cancer Letters.112(2): 127–133.doi:10.1016/S0304-3835(96)04557-0.PMID 9066718.

External links[edit]

Galangin on Chemblink.com

[ciolino&yeh-1] Ciolino, H. P.; Yeh, G. C. (1999)."The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor".British Journal of Cancer.79(9/10): 1340–1346.doi:10.1038/sj.bjc.6690216.PMC2362711.PMID 10188874.

[pmid9292410-2] Afolayan AJ, Meyer JJ (1997). "The antimicrobial activity of 3,5,7-trihydroxyflavone isolated from the shoots of Helichrysum aureonitens".Journal of Ethnopharmacology.57(3): 177–181.doi:10.1016/s0378-8741(97)00065-2.PMID 9292410.

[3] Kaur, A.; Singh, R.; Dey, C. S.; Sharma, S. S.; Bhutani, K. K.; Singh, I. P. (2010)."Antileishmanial phenylpropanoids fromAlpinia galanga(Linn.) Willd "(PDF).Indian Journal of Experimental Biology.48(3): 314–317.PMID 21046987.

[4] Tosi, E; Re, E; Ortega, M; Cazzoli, A (2007). "Food preservative based on propolis: Bacteriostatic activity of propolis polyphenols and flavonoids upon Escherichia coli".Food Chemistry.104(3): 1025–1029.doi:10.1016/j.foodchem.2007.01.011.

[pmid16428027-5] Cushnie TP, Lamb AJ (2006). "Assessment of the antibacterial activity of galangin against 4-quinolone resistant strains of Staphylococcus aureus".Phytomedicine.13(3): 187–191.doi:10.1016/j.phymed.2004.07.003.PMID 16428027.

[pmid15985350-6] Cushnie TP, Lamb AJ (2005). "Detection of galangin-induced cytoplasmic membrane damage in Staphylococcus aureus by measuring potassium loss".Journal of Ethnopharmacology.101(1–3): 243–248.doi:10.1016/j.jep.2005.04.014.PMID 15985350.

[pmid9174978-7] Afolayan AJ, Meyer JJ, Taylor MB, Erasmus D (1997). "Antiviral activity of galangin isolated from the aerial parts of Helichrysum aureonitens".Journal of Ethnopharmacology.56(2): 165–169.doi:10.1016/s0378-8741(97)01514-6.PMID 917497.

[8] So, F. V.; Guthrie, N.; Chambers, A. F.; Moussa, M.; Carroll, K. K. (1996). "Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices".Nutrition and Cancer.26(2): 167–181.doi:10.1080/01635589609514473.PMID 8875554.

[9] So, F.; Guthrie, N.; Chambers, A. F.; Carroll, K. K. (1997). "Inhibition of proliferation of estrogen receptor-positive MCF-7 human breast cancer cells by flavonoids in the presence and absence of excess estrogen".Cancer Letters.112(2): 127–133.doi:10.1016/S0304-3835(96)04557-0.PMID 9066718.

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