Cinnamoyl glucosides of catechin and dimeric procyanidins from young leaves of Inga umbellifera (Fabaceae)

• DOI: 10.1016/j.phytochem.2003.11.012
• Publication Date: 2004-01-25T08:27:43Z
• Authors: John Lokvam; Phyllis D Coley; Thomas A Kursar
• Keywords: Molecular Structure; Fabaceae; 01 natural sciences; Catechin; 0104 chemical sciences; 3. Good health; Plant Leaves; Glucosides; Cinnamates; Biflavonoids; Proanthocyanidins; Dimerization; Nuclear Magnetic Resonance, Biomolecular

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.