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Wikipedia

Galangin

April 12, 2024

Galangin is a flavonol, a type of flavonoid.

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
  • 548-83-4 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:5262 Y
ChEMBL
  • ChEMBL309490 Y
ChemSpider
  • 4444935 Y
ECHA InfoCard 100.008.147
  • 410
KEGG
  • C10044 Y
  • 5281616
UNII
  • 142FWE6ECS Y
  • DTXSID70203288
  • 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
  • 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).
Y verify (what is YN ?)

Occurrence edit

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 edit

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

References edit

  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. ^ 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.
  8. ^ 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.
  9. ^ 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 edit

  • Galangin on Chemblink.com

April 12, 2024
galangin, flavonol, type, flavonoid, namesiupac, name, trihydroxyflavonesystematic, iupac, name, trihydroxy, phenyl, benzopyran, oneother, names, norizalpinin3, trioh, flavoneidentifierscas, number, model, jsmol, interactive, imagechebi, chebi, 5262, ychembl, . Galangin is a flavonol a type of flavonoid Galangin NamesIUPAC name 3 5 7 TrihydroxyflavoneSystematic IUPAC name 3 5 7 Trihydroxy 2 phenyl 4H 1 benzopyran 4 oneOther names Norizalpinin3 5 7 triOH FlavoneIdentifiersCAS Number 548 83 4 Y3D model JSmol Interactive imageChEBI CHEBI 5262 YChEMBL ChEMBL309490 YChemSpider 4444935 YECHA InfoCard 100 008 147IUPHAR BPS 410KEGG C10044 YPubChem CID 5281616UNII 142FWE6ECS YCompTox Dashboard EPA DTXSID70203288InChI 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 YKey VCCRNZQBSJXYJD UHFFFAOYSA N YInChI 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 19HKey VCCRNZQBSJXYJD UHFFFAOYACSMILES O C1c3c O C C1 O c2ccccc2 cc O cc3OPropertiesChemical formula C 15H 10O 5Molar mass 270 240 g mol 1Density 1 579 g mLMelting 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 Y N Infobox references Contents 1 Occurrence 2 Biological activities 3 References 4 External linksOccurrence editGalangin 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 editGalangin has been shown to have in vitro antibacterial 5 6 and antiviral activity 7 It also inhibits the growth of breast tumor cells in vitro 8 9 References edit 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 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 editGalangin on Chemblink com Retrieved from https en wikipedia org w index php title Galangin amp oldid 1162495597, wikipedia, wiki, book, books, library,

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