![]() | |
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 | |
3D model (JSmol) | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.222.924 |
KEGG | |
PubChem CID | |
UNII | |
CompTox Dashboard (EPA) | |
| |
| |
Properties | |
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). |
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 rhizome 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] It is also present in certain wines. [9]
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]
3'-O-Methylastilbin shows an immunosuppressive activity against contact dermatitis. [7]