アスチルビン

アスチルビン
	IUPAC名 (2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-2,3-dihydrochromen-4-one
	別称 Isoastilbin; Neoastilbin; Neoisoastilbin; Taxifolin 3-O-rhamnoside; Taxifolin 3-rhamnoside; (2R-trans)-3-((6-Deoxy-alpha-L-mannopyranosyl)oxy)-2-(3,4- dihydroxyphenyl)-2,3-dihydro-5,7-dihydroxy-4H-1-benzopyran-4-one
識別情報
CAS登録番号	54141-72-9
PubChem	119258
ChemSpider	106533
KEGG	C17449
ChEBI	CHEBI:38200 ;
ChEMBL	CHEMBL486017
	SMILES O=C3c4c(O)cc(O)cc4O[C@H](c1ccc(O)c(O)c1)[C@H]3O[C@@H]2O[C@H]([C@H](O)[C@@H](O)[C@H]2O)C;
	InChI InChI=1S/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1 Key: ZROGCCBNZBKLEL-MPRHSVQHSA-N ; InChI=1/C21H22O11/c1-7-15(26)17(28)18(29)21(30-7)32-20-16(27)14-12(25)5-9(22)6-13(14)31-19(20)8-2-3-10(23)11(24)4-8/h2-7,15,17-26,28-29H,1H3/t7-,15-,17+,18+,19+,20-,21-/m0/s1 Key: ZROGCCBNZBKLEL-MPRHSVQHBV;
特性
化学式	C21H22O11
モル質量	450.39 g/mol
外観	茶色粉末
	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。

アスチルビン(Astilbin)は、フラバノノールの一つである。アスチルビンは(2R-trans)型異性体、ネオイソアスチルビンは(2S-cis)型異性体、イソアスチルビンは(2R-cis)型異性体である^[2]。

天然の存在

アスチルビンは、セイヨウオトギリ、Dimorphandra mollis^[3]、Harungana madagascariensisの葉^[4]、Astilbe thunbergiiの根茎、Astilbe odontophyllaの根^[5]、ドブクリョウの根茎^[6]、Hymenaea martianaの樹皮^[7] で見られる。

食品

Engelhardia roxburghianaから作られる黄杞茶から単離される^[2]。特定の種類のワインにも含まれる^[8]。

利用

ヤガ科のAnticarsia gemmatalisとSpodoptera frugiperdaに対する殺虫剤として作用する^[3]。また、in vitroでの抗菌活性^[4]及び火傷治癒の活性^[5]を示す。中国医学で用いられる^[6]。

出典

^ ^a ^b http://anwabio.com/asti.htm^{[リンク切れ]}
^ ^a ^b Astilbin on PubChem
^ ^a ^b Biological activity of astilbin from Dimorphandra mollis against Anticarsia gemmatalis and Spodoptera frugiperda, Luciane G Batista Pereira, Fernando Petacci, Joao B Fernandes, Arlene G Correa, Paulo C Vieira 1, M Fatima G F da Silva, Osmar Malaspina, 2002
^ ^a ^b Isolation and in vitro antibacterial activity of astilbin, the bioactive flavanone from the leaves of Harungana madagascariensis Lam. ex Poir. (Hypericaceae), B. Moulari, Y. Pellequer, H. Lboutounne, C. Girard, J.-P. Chaumont, J. Millet and F. Muyard,
^ ^a ^b Effects of Astilbe thunbergii rhizomes on wound healing: Part 1. Isolation of promotional effectors from Astilbe thunbergii rhizomes on burn wound healing, Yoshiyuki Kimura, Maho Sumiyoshi and Masahiro Sakanaka, 2006
^ ^a ^b First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine, Ken Ohmori, Hiroki Ohrui and Keisuke Suzuki, 2000
^ Isolation, Chemical Identification and Pharmacological Evaluation of Eucryphin, Astilbin and Engelitin Obtained from the Bark of Hymenaea martiana. Eliane Carneiro, Joao B. Calixto, Franco Delle Monacheand Rosendo A. Yunes, Pharmaceutical Biology, 1993, Vol. 31, No. 1, Pages 38-46
^ Levels of Stilbene Oligomers and Astilbin in French Varietal Wines and in Grapes during Noble Rot Development, Nicolas Landrault, Fabienne Larronde, Jean-Claude Delaunay, Chantal Castagnino, Joseph Vercauteren, Jean-Michel Merillon, Francis Gasc, Gerard Cros and Pierre-Louis Teissedre, J. Agric. Food Chem., 2002, 50 (7), pages 2046-2052, doi:10.1021/jf010794g
^ Identification of a New Metabolite of Astilbin, 3'-O-Methylastilbin, and Its Immunosuppressive Activity against Contact Dermatitis, Jianming Guo, Feng Qian, Jianxin Li, Qiang Xu, Ting Chen, 2006

[anwabio-1] ttp://anwabio.com/asti.htm^{[リンク切れ]}

[PubChem-2] Astilbin on PubChem

[Batista-3] Biological activity of astilbin from Dimorphandra mollis against Anticarsia gemmatalis and Spodoptera frugiperda, Luciane G Batista Pereira, Fernando Petacci, Joao B Fernandes, Arlene G Correa, Paulo C Vieira 1, M Fatima G F da Silva, Osmar Malaspina, 2002

[Moulari-4] Isolation and in vitro antibacterial activity of astilbin, the bioactive flavanone from the leaves of Harungana madagascariensis Lam. ex Poir. (Hypericaceae), B. Moulari, Y. Pellequer, H. Lboutounne, C. Girard, J.-P. Chaumont, J. Millet and F. Muyard,

[Yoshiyuki-5] Effects of Astilbe thunbergii rhizomes on wound healing: Part 1. Isolation of promotional effectors from Astilbe thunbergii rhizomes on burn wound healing, Yoshiyuki Kimura, Maho Sumiyoshi and Masahiro Sakanaka, 2006

[Ohmori-6] First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine, Ken Ohmori, Hiroki Ohrui and Keisuke Suzuki, 2000

[7] Isolation, Chemical Identification and Pharmacological Evaluation of Eucryphin, Astilbin and Engelitin Obtained from the Bark of Hymenaea martiana. Eliane Carneiro, Joao B. Calixto, Franco Delle Monacheand Rosendo A. Yunes, Pharmaceutical Biology, 1993, Vol. 31, No. 1, Pages 38-46

[8] Levels of Stilbene Oligomers and Astilbin in French Varietal Wines and in Grapes during Noble Rot Development, Nicolas Landrault, Fabienne Larronde, Jean-Claude Delaunay, Chantal Castagnino, Joseph Vercauteren, Jean-Michel Merillon, Francis Gasc, Gerard Cros and Pierre-Louis Teissedre, J. Agric. Food Chem., 2002, 50 (7), pages 2046-2052, doi:10.1021/jf010794g

[Jianming-9] Identification of a New Metabolite of Astilbin, 3'-O-Methylastilbin, and Its Immunosuppressive Activity against Contact Dermatitis, Jianming Guo, Feng Qian, Jianxin Li, Qiang Xu, Ting Chen, 2006

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天然の存在

食品

利用

関連化合物

出典