C(13)-Norisoprenoid glucoconjugates from lulo (Solanum quitoense L.) leaves.
With the aid of multilayer coil countercurrent chromatography, subsequent acetylation, and liquid chromatographic purification of a glycosidic mixture obtained from lulo (Solanum quitoense L.) leaves, three C(13)-norisoprenoid glucoconjugates were isolated in pure form. Their structures were elucidated by NMR, MS, and CD analyses to be the novel (6R,9R)-13-hydroxy-3-oxo-alpha-ionol 9-O-beta-D-glucopyranoside (4a), the uncommon (3S,5R,8R)-3, 5-dihydroxy-6,7-megastigmadien-9-one 5-O-beta-D-glucopyranoside (citroside A) (5a), and the known (6S,9R)-vomifoliol 9-O-beta-D-glucopyranoside (6a). Enzymatic treatment of compound 5a showed the formation of 3-hydroxy-7,8-didehydro-beta-ionone (7), an important lulo peeling volatile, which in its turn after chemical reduction and heated acid catalyzed rearrangement generates beta-damascenone (9) and 3-hydroxy-beta-damascone (10).
Osorio
C
C
Departamento de Química, Universidad Nacional de Colombia, Bogotá.
Duque
C
C
Fujimoto
Y
Y
D005638:Fruit; D005960:Glucosides / Q000737:chemistry* / Q000302:isolation & purification; D006001:Glycoconjugates / Q000737:chemistry* / Q000302:isolation & purification; D008968:Molecular Conformation; D045792:Norisoprenoids; D018515:Plant Leaves / Q000737:chemistry; D019657:Solanaceae / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry* / Q000302:isolation & purification
D005960:Glucosides; D006001:Glycoconjugates; D045792:Norisoprenoids; D013729:Terpenes; C008157:beta-ionone