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Galangin - Wikipedia

From Wikipedia, the free encyclopedia

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^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:5262^Y
ChEMBL	ChEMBL309490^Y
ChemSpider	4444935^Y
ECHA InfoCard	100.008.147
IUPHAR/BPS	410
KEGG	C10044^Y
PubChem CID	5281616
UNII	142FWE6ECS^Y
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^Y Key: VCCRNZQBSJXYJD-UHFFFAOYSA-N^Y 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). Y verify (what is ^YN ?) 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

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Flavonols

Aglycones

Conjugates

Glycosides of herbacetin

Glycosides of kaempferol

Afzelin (Kaempferol 3-rhamnoside)
Astragalin (kaempferol 3-O-glucoside)
Kaempferitrin (kaempferol 3,7-dirhamnoside)
Juglanin (Kaempferol 3-O-arabinoside)
Kaempferol 3-alpha-L-arabinopyranoside
Kaempferol 3-alpha-D-arabinopyranoside
Kaempferol 7-alpha-L-arabinoside
Kaempferol 7-O-glucoside
Kaempferol 3-lathyroside
Kaempferol 4'-rhamnoside
Kaempferol 5-rhamnoside
Kaempferol 7-rhamnoside
Kaempferol 7-O-alpha-L-rhamnofuranoside
Kaempferol 3-xyloside
Kaempferol 7-xyloside
Robinin (kaempferol-3-O-robinoside-7-O-rhamnoside)
Kaempferol 3-O-rutinoside
Sophoraflavonoloside (Kaempferol 3-O-sophoroside)
Trifolin (Kaempferol 3-O-beta-D-galactoside)

Glycosides of myricetin

Conjugates of quercetin

Sulfates

Glycosides

Avicularin (quercetin-3-O-α-L-arabinofuranoside)
CTN-986
Guaijaverin (quercetin 3-O-arabinoside)
Heliosin (quercetin 3-digalactoside)
Hyperoside (quercetin 3-O-galactoside)
Isoquercetin (quercetin 3-O-glucoside)
Miquelianin (quercetin 3-O-glucuronide)
Quercetin 3,4'-diglucoside
Quercetin-3-sophorodide
Quercitrin (quercetin 3-O-rhamnoside)
Rutin (quercetin rutinoside)
Reinutrin (quercetin-3-D-xyloside)
Spiraeoside (quercetin 4'-O-glucoside)
Taxillusin (galloylated 3-O-glucoside of quercetin°

O-Methylated flavonols

Aglycones

Glycosides

of isorhamnetin	Narcissin (Isorhamnetin 3-O-rutinoside) Isorhamnetin 3-O-glucoside Tamarixetin 7-rutinoside
other	Azalein (Azaleatin 3-O-α-L-rhamnoside) Centaurein (Centaureidin 7-O-glucoside) Eupalin (Eupalitin 3-0-rhamnoside) Eupatolin (Eupatolitin 3-O-rhamnoside) Jacein (Jaceidin 7-O-glucoside) Patulitrin (Patuletin 7-O-glucoside Xanthorhamnin (Rhamnetin glycoside)

Derivative flavonols

Aglycones	Noricaritin Dihydronoricaritin
Glycosides	Amurensin Icariin Phelloside Dihydrophelloside Rutin S

Pyranoflavonols

Aglycones	Karanjachromene

Furanoflavonols

Aglycones	Karanjin
Glycosides	Pongamoside A, B and C

Semisynthetic

Glycosides	Hydroxyethylrutosides Monoxerutin Troxerutin

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