ガランギン

ガランギン
	IUPAC名 3,5,7-trihydroxy-2-phenylchromen-4-one
	別称 Norizalpinin; 3,5,7-Trihydroxyflavone; 3,5,7-triOH-Flavone
識別情報
CAS登録番号	548-83-4
PubChem	5281616
ChemSpider	4444935
UNII	142FWE6ECS
日化辞番号	J1.607A
KEGG	C10044
ChEBI	CHEBI:5262;
ChEMBL	CHEMBL309490
IUPHAR/BPS	410
	SMILES O=C1c3c(O/C(=C1/O)c2ccccc2)cc(O)cc3O;
	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 Key: VCCRNZQBSJXYJD-UHFFFAOYSA-N; 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;
特性
化学式	C15H10O5
モル質量	270.24 g mol−1
精密質量	270.052823 u
密度	1.579 g/mL
融点	214-215 °C, 487-488 K, 417-419 °F
	特記なき場合、データは常温 (25 °C)・常圧 (100 kPa) におけるものである。

ガランギン（galangin）はフラボノールの一つ。コウリョウキョウ (Alpinia officinarum) [1]やHelichrysum aureonitens に高濃度に含まれるほか[2]、ナンキョウ (Alpinia galanga) の地下茎[3]やプロポリス[4]にも含まれている。in vitro 実験においては、抗細菌[5][6]・抗ウイルス作用[7]のほか、乳癌細胞の増殖を遅くすることも示されている[8][9]。

脚注

Ciolino HP, Yeh GC (1999). “The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor”. Br. J. 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 CS, Sharma SS, Bhutani KK, Singh IP (2010). “Antileishmanial phenylpropanoids from Alpinia galanga (Linn.) Willd.”. Indian J. Exp. Biol. 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: 1025. doi:10.1016/j.foodchem.2007.01.011.
Cushnie TPT, 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 TPT, 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.

外部リンク

Galangin on Chemblink.com

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[1] Ciolino HP, Yeh GC (1999). “The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor”. Br. J. Cancer 79 (9-10): 1340-1346. doi:10.1038/sj.bjc.6690216. PMC 2362711. PMID 10188874.

[pmid9292410-2] 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 CS, Sharma SS, Bhutani KK, Singh IP (2010). “Antileishmanial phenylpropanoids from Alpinia galanga (Linn.) Willd.”. Indian J. Exp. Biol. 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: 1025. doi:10.1016/j.foodchem.2007.01.011.

[pmid16428027-5] Cushnie TPT, 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.

[pmid15985350-6] Cushnie TPT, 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.

[pmid9174978-7] 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.