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 ;
PubChem CID	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	270.240 g·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 their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Galangin is a flavonol, a type of flavonoid.

Occurrence

Galangin is found in high concentrations in plants like Alpinia officinarum (lesser galangal)^[1] and Helichrysum aureonitens.^[2] It is also found in the rhizome of Alpinia galanga^[3] and in propolis.^[4]

Biological activities

Galangin has been shown to have in vitro antibacterial^[5]^[6]^[7] and antiviral activity.^[8] It also inhibits the growth of breast tumor cells in vitro.^[9]^[10]

References

^ 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. PMC 2362711. 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 from Alpinia 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.
^ Liu, Yang Sylvia; Zhang, Chengqian; Khoo, Bee Luan; Hao, Piliang; Chua, Song Lin (2024-09-02). "Dual-species proteomics and targeted intervention of animal-pathogen interactions". Journal of Advanced Research. doi:10.1016/j.jare.2024.08.038. ISSN 2090-1232.
^ 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

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. PMC 2362711. 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 from Alpinia 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.

[7] Liu, Yang Sylvia; Zhang, Chengqian; Khoo, Bee Luan; Hao, Piliang; Chua, Song Lin (2024-09-02). "Dual-species proteomics and targeted intervention of animal-pathogen interactions". Journal of Advanced Research. doi:10.1016/j.jare.2024.08.038. ISSN 2090-1232.

[pmid9174978-8] 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.

[9] 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.

[10] 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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