:Galangin
{{chembox
| Watchedfields = changed
| verifiedrevid = 443831073
| Name = Galangin
| ImageFile = Galangin.svg
| ImageSize = 220px
| ImageAlt = Skeletal formula of galangin
| ImageFile1 = Galangin-3D-balls.png
| ImageAlt1 = Ball-and-stick model of the galangin molecule
| IUPACName = 3,5,7-Trihydroxyflavone
| SystematicName = 3,5,7-Trihydroxy-2-phenyl-4H-1-benzopyran-4-one
| OtherNames = Norizalpinin
3,5,7-triOH-Flavone
|Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4444935
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = C10044
| 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
| InChIKey = VCCRNZQBSJXYJD-UHFFFAOYAC
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 309490
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = VCCRNZQBSJXYJD-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 548-83-4
| PubChem = 5281616
| IUPHAR_ligand = 410
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 142FWE6ECS
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 5262
| SMILES = O=C1c3c(O/C(=C1/O)c2ccccc2)cc(O)cc3O
}}
|Section2={{Chembox Properties
| C=15
| H=10
| O=5
| Density = 1.579 g/mL
| MeltingPtC = 214 to 215
| MeltingPt_notes =
| BoilingPt =
}}
}}
Occurrence
Galangin is found in high concentrations in plants like Alpinia officinarum (lesser galangal){{Cite journal | last1 = Ciolino | first1 = H. P. | last2 = Yeh | first2 = G. C. | doi = 10.1038/sj.bjc.6690216 | title = The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor | journal = British Journal of Cancer | volume = 79 | issue = 9/10 | pages = 1340–1346 | year = 1999 | pmid = 10188874| pmc = 2362711}} and Helichrysum aureonitens.{{cite journal|vauthors=Afolayan AJ, Meyer JJ | title=The antimicrobial activity of 3,5,7-trihydroxyflavone isolated from the shoots of Helichrysum aureonitens | journal=Journal of Ethnopharmacology | year= 1997 | volume= 57 | issue= 3 | pages= 177–181 | pmid=9292410 | doi=10.1016/s0378-8741(97)00065-2}} It is also found in the rhizome of Alpinia galanga{{Cite journal
| last1 = Kaur | first1 = A.
| last2 = Singh | first2 = R.
| last3 = Dey | first3 = C. S.
| last4 = Sharma | first4 = S. S.
| last5 = Bhutani | first5 = K. K.
| last6 = Singh | first6 = I. P.
| title = Antileishmanial phenylpropanoids from Alpinia galanga (Linn.) Willd
| journal = Indian Journal of Experimental Biology
| volume = 48
| issue = 3
| pages = 314–317
| year = 2010
| pmid = 21046987
| url = http://nopr.niscair.res.in/bitstream/123456789/7407/1/IJEB%2048(3)%20314-317.pdf
}} and in propolis.{{Cite journal | last1 = Tosi | first1 = E | last2 = Re | first2 = E | last3 = Ortega | first3 = M | last4 = Cazzoli | first4 = A | title = Food preservative based on propolis: Bacteriostatic activity of propolis polyphenols and flavonoids upon Escherichia coli | doi = 10.1016/j.foodchem.2007.01.011 | journal = Food Chemistry | volume = 104 | pages = 1025–1029 | year = 2007 | issue = 3 }}
Biological activities
Galangin has been shown to have in vitro antibacterial{{cite journal|vauthors=Cushnie TP, Lamb AJ | title=Assessment of the antibacterial activity of galangin against 4-quinolone resistant strains of Staphylococcus aureus| journal=Phytomedicine | year= 2006 | volume= 13 | issue= 3 | pages= 187–191 | pmid=16428027 | doi=10.1016/j.phymed.2004.07.003| url=https://hal.science/hal-04842337}}{{cite journal|vauthors=Cushnie TP, Lamb AJ | title=Detection of galangin-induced cytoplasmic membrane damage in Staphylococcus aureus by measuring potassium loss| journal=Journal of Ethnopharmacology | year= 2005 | volume= 101 | issue= 1–3 | pages= 243–248 | pmid=15985350 | doi=10.1016/j.jep.2005.04.014| url=https://hal.science/hal-04842111}}{{Cite journal |last1=Liu |first1=Yang Sylvia |last2=Zhang |first2=Chengqian |last3=Khoo |first3=Bee Luan |last4=Hao |first4=Piliang |last5=Chua |first5=Song Lin |date=2024-09-02 |title=Dual-species proteomics and targeted intervention of animal-pathogen interactions |url=https://www.sciencedirect.com/science/article/pii/S2090123224003837 |journal=Journal of Advanced Research |doi=10.1016/j.jare.2024.08.038 |issn=2090-1232|doi-access=free |pmid=39233003 }} and antiviral activity.{{cite journal|vauthors=Afolayan AJ, Meyer JJ, Taylor MB, Erasmus D | title=Antiviral activity of galangin isolated from the aerial parts of Helichrysum aureonitens | journal=Journal of Ethnopharmacology | year= 1997 | volume= 56 | issue= 2 | pages= 165–169 | pmid=917497 | doi=10.1016/s0378-8741(97)01514-6}} It also inhibits the growth of breast tumor cells in vitro.{{Cite journal
| last1 = So | first1 = F. V.
| last2 = Guthrie | first2 = N.
| last3 = Chambers | first3 = A. F.
| last4 = Moussa | first4 = M.
| last5 = Carroll | first5 = K. K.
| title = Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices
| doi = 10.1080/01635589609514473
| journal = Nutrition and Cancer
| volume = 26
| issue = 2
| pages = 167–181
| year = 1996
| pmid = 8875554
References
{{Reflist}}
External links
- [http://www.chemblink.com/products/548-83-4.htm Galangin on Chemblink.com]
{{flavonol}}