Astilbin

Astilbin
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-dihydrochromen-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
PubChem	119258
ChemSpider	106533 Y
Jmol-3D images	Image 1
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 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
Properties
Molecular formula	C21H22O11
Molar mass	450.39 g/mol
Exact mass	450.116212 u
Appearance	brown powder[1]
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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]

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 rhizone of Smilax glabra^[7] (Chinaroot, Smilacaceae) and in the bark of Hymenaea martiana.^[8] It can be isolated from Kohki tea processed from Engelhardtia chrysolepis (huang-qui).^[2]

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

1. ^ ^{a b} http://anwabio.com/asti.htm
2. ^ ^{a b} Astilbin on PubChem
3. ^ ^{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
4. ^ ^{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,
5. ^ ^{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
6. ^ ^{a b} First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine, Ken Ohmori, Hiroki Ohrui and Keisuke Suzuki, 2000
7. ^ ^{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
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