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
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.222.924 Edit this at Wikidata
KEGG
UNII
  • 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 checkY
    Key: ZROGCCBNZBKLEL-MPRHSVQHSA-N checkY
  • 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
  • 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
C21H22O11
Molar mass 450.39 g/mol
Appearance brown powder
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X markN verify (what is checkYX markN ?)

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.

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 (Fava d'anta, Fabaceae), in the leaves of Harungana madagascariensis (Hypericaceae), in the rhizome of Astilbe thunbergii, in the root of Astilbe odontophylla (Saxifragaceae), in the rhizome of Smilax glabra (Chinaroot, Smilacaceae) and in the bark of Hymenaea martiana.

In food

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

Uses

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


3'-O-Methylastilbin shows an immunosuppressive activity against contact dermatitis.


References

  1. 1 2 http://anwabio.com/asti.htm[permanent dead link]
  2. 1 2 Astilbin on PubChem
  3. 1 2 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[link removed]
  4. 1 2 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[link removed],
  5. 1 2 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[link removed]
  6. 1 2 First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine, Ken Ohmori, Hiroki Ohrui and Keisuke Suzuki, 2000[link removed]
  7. 1 2 "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.
  8. ↑ 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
  9. ↑ 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