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Galangin

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(Redirected from 3,5,7-Trihydroxyflavone)
Galangin
Skeletal formula of galangin
Ball-and-stick model of the galangin molecule
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
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.147 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: VCCRNZQBSJXYJD-UHFFFAOYSA-N checkY
  • 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
  • O=C1c3c(O/C(=C1/O)c2ccccc2)cc(O)cc3O
Properties
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).
checkY verify (what is checkY☒N ?)

Galangin is a flavonol, a type of flavonoid.

Occurrence

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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

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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

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  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.
  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.
  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.
  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.
  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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