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(-)-Fustin

Fustin
Fustin.svg
Names
IUPAC name
(2R,3R)-3,3′,4′,7-Tetrahydroxyflavan-4-one
Preferred IUPAC name
(2R,3R)-2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
Other names
2,3-Dihydrofisetin
3,7,3',4'-Tetrahydroxyflavanone
2,3-Dihydrofisetin
3′,4′,7-Trihydroxyflavanol
Identifiers
  • 20725-03-5 checkY
3D model (JSmol)
ECHA InfoCard 100.039.975 Edit this at Wikidata
UNII
  • C1=CC(=C(C=C1[C@@H]2[C@H](C(=O)C3=C(O2)C=C(C=C3)O)O)O)O
Properties
C15H12O6
Molar mass 288.255 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Fustin, sometimes called "dihydrofisetin", is a flavanonol, a type of flavonoid. It can be found in young fustic (Cotinus coggygria)[1] and in the lacquer tree (Toxicodendron vernicifluum).[2]

Fustin shows protective effects on 6-hydroxydopamine-induced neuronal cell death.[2]

Unlike fisetin, fustin has no double bond in the C-ring. This makes fustin a flavan, with two stereocenters and four stereoisomers.

References[]

  1. ^ Valianou, Lemonia; Stathopoulou, Konstantina; Karapanagiotis, Ioannis; Magiatis, Prokopios; Pavlidou, Eleni; Skaltsounis, Alexios-Leandros; Chryssoulakis, Yannis (2009). "Phytochemical analysis of young fustic (Cotinus coggygria heartwood) and identification of isolated colourants in historical textiles". Analytical and Bioanalytical Chemistry. 394 (3): 871. doi:10.1007/s00216-009-2767-z. PMID 19352635.
  2. ^ a b Park, Byung Chul; Lee, Yong Soo; Park, Hee-Juhn; Kwak, Mi-Kyoung; Yoo, Bong Kyu; Kim, Joo Young; Kim, Jung-Ae (2007). "Protective effects of fustin, a flavonoid from Rhus verniciflua Stokes, on 6-hydroxydopamine-induced neuronal cell death". Experimental & Molecular Medicine. 39 (3): 316. doi:10.1038/emm.2007.35. PMID 17603285.