Astilbin

Astilbin
Names

IUPAC name (2R,3R)-3′,4′,5,7-Tetrahydroxy-3-(α-L-rhamnopyranosyloxy)flavan-4-one
Systematic IUPAC name (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-dihydro-4H-1-benzopyran-4-one
Other names 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^[1]
Identifiers
CAS Number	54141-72-9^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:38200^Y
ChEMBL	ChEMBL486017^Y
ChemSpider	106533^Y
ECHA InfoCard	100.222.924
KEGG	C17449
PubChem CID	119258
UNII	KA92CW3M68^Y
CompTox Dashboard (EPA)	DTXSID501019948
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^Y Key: ZROGCCBNZBKLEL-MPRHSVQHSA-N^Y 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
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
Properties
Chemical formula	C₂₁H₂₂O₁₁
Molar mass	450.39 g/mol
Appearance	brown powder^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Chemical compound

Astilbin is a flavanonol, a type of flavonoid. Astilbin is the (2R-trans)-isomer; neoisoastilbin is the (2S-cis)-isomer and isoastilbin is the (2R-cis)-isomer.^[2]

Natural occurrences

Astilbin can be found in St John's wort (Hypericum perforatum, Clusiaceae, subfamily Hypericoideae, formerly often considered a full family Hypericaceae), in Dimorphandra mollis^[3] (Fava d'anta, Fabaceae), in the leaves of Harungana madagascariensis (Hypericaceae),^[4] in the rhizome of Astilbe thunbergii,^[5] in the root of Astilbe odontophylla^[6](Saxifragaceae), in the rhizome of Smilax glabra^[7] (Chinaroot, Smilacaceae) and in the bark of Hymenaea martiana.^[8]

In food

It can be isolated from Kohki tea processed from Engelhardtia chrysolepis (huang-qui).^[2] It is also present in certain wines.^[9]

Uses

Astilbin can act as an insecticide against Anticarsia gemmatalis and Spodoptera frugiperda.^[3] It shows in vitro antibacterial activity^[4] and activity on burn wound healing.^[5] Astilbin is used in traditional Chinese medicine.^[6]

Related compounds

3'-O-Methylastilbin shows an immunosuppressive activity against contact dermatitis.^[7]

References

^ ^a ^b http://anwabio.com/asti.htm^{[permanent dead link]}
^ ^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, João B Fernandes, Arlene G Corrêa, Paulo C Vieira 1, M Fátima 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
^ ^a ^b "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". Archived from the original on 2011-06-07. Retrieved 2009-08-30.
^ Isolation, Chemical Identification and Pharmacological Evaluation of Eucryphin, Astilbin and Engelitin Obtained from the Bark of Hymenaea martiana. Eliane Carneiro, João 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, Gérard Cros and Pierre-Louis Teissedre, J. Agric. Food Chem., 2002, 50 (7), pages 2046–2052, doi:10.1021/jf010794g