Cinnamoyl glucosides of catechin and dimeric procyanidins from young leaves of Inga umbellifera (Fabaceae).
The rapidly growing, nearly achlorophyllous, young leaves of Inga umbellifera express high concentrations of mono and dimeric 3-O-gluco-cinnamoyl catechin/epicatechin, rare forms of substituted flavan-3-ols. Here we present structures for five novel compounds in this class: three monomers [catechin-3-O-beta-D-gluco(2-cinnamoyl)pyranoside, catechin-3-O-beta-D-gluco(6-cinnamoyl) pyranoside, catechin-3-O-beta-D-gluco(2,6-biscinnamoyl)pyranoside] and two dimeric procyanidins [catechin-3-O-beta-D-glucopyrano-(4alpha-->8)-catechin-3-O-beta-D-gluco(2-cinnamoyl)pyranoside and catechin-3-O-beta-D-glucopyrano-(4alpha-->8)-epicatechin-3-O-beta-D-gluco(6-cinnamoyl)pyranoside]. The young leaves of Inga umbellifera express high concentrations of 3-O-(cinnamoyl)glucosides of catechin and epicatechin.
Lokvam
John
J
Department of Biology, University of Utah, 257 S 1400 E, Salt Lake City, UT 84112-0840, USA. lokvam@biology.utah.edu
Coley
Phyllis D
PD
Kursar
Thomas A
TA
D044946:Biflavonoids; D002392:Catechin / Q000737:chemistry*; D002934:Cinnamates / Q000737:chemistry*; D019281:Dimerization; D007887:Fabaceae / Q000737:chemistry*; D005960:Glucosides / Q000737:chemistry*; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D018515:Plant Leaves / Q000737:chemistry; D044945:Proanthocyanidins
D044946:Biflavonoids; D002934:Cinnamates; D005960:Glucosides; D044945:Proanthocyanidins; C017674:procyanidin; D002392:Catechin