Galangin

Last updated
Galangin
Galangin.svg
Galangin-3D-balls.png
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 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
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 Yes check.svgY
    Key: VCCRNZQBSJXYJD-UHFFFAOYSA-N Yes check.svgY
  • 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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

Contents

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

  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. PMID   39233003.
  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.
This page is based on this Wikipedia article
Text is available under the CC BY-SA 4.0 license; additional terms may apply.
Images, videos and audio are available under their respective licenses.