Spermidine Derivatives in Lulo (Solanum quitoense Lam.) Fruit: Sensory (Taste) versus Biofunctional (ACE-Inhibition) Properties.
The bitterness in lulo (Solanum quitoense Lam.) fruit is increased during processing (juicing or drying). To identify the bitter-active compounds, the ethanolic fruit pulp extract was subjected to RP-18 solid-phase extraction, and then sensory-guided fractionated by HPLC. Two spermidine derivatives, N(1),N(4),N(8)-tris(dihydrocaffeoyl)spermidine and N(1),N(8)-bis(dihydrocaffeoyl)spermidine, were isolated and their structures confirmed by analysis of their HPLC-ESI/MS and (1)H and (13)C NMR data. The N(1),N(4),N(8)-tris(dihydrocaffeoyl)spermidine was synthesized and used as an authentic sample to unequivocally confirm the structure of this compound and to quantitate it in both fresh and dried fruit. In silico analyses demonstrated that spermidine derivatives identified in lulo pulp exhibited a strong ACE-I (angiotensin I-converting enzyme) inhibitory activity. Subsequently, these results were confirmed by in vitro analyses and showed the potential use of lulo fruit pulp as an ingredient of functional foods related to the prevention of blood hypertension.
Departamento de Química, Universidad Nacional de Colombia , AA 14490, Bogotá, Colombia.
Diana Paola
DP
Forero
Department of Chemistry and Materials Science, Tokyo Institute of Technology , Meguro, Tokyo 152-8551, Japan.
Chieko
C
Masatani
Department of Chemistry and Materials Science, Tokyo Institute of Technology , Meguro, Tokyo 152-8551, Japan.
Yoshinori
Y
Fujimoto
Laboratorio de Química Bioorgánica, Departamento de Química, Facultad de Ciencias Básicas y Aplicadas, Universidad Militar Nueva Granada , AA 49300, Bogotá, Colombia.
Ericsson
E
Coy-Barrera
Department of Food Science and Nutrition, 145 Food Science and Nutrition Building, 1334 Eckles Avenue, University of Minnesota , St. Paul, Minnesota 55108, United States.
Devin G
DG
Peterson
Departamento de Química, Universidad Nacional de Colombia , AA 14490, Bogotá, Colombia.
Coralia
C
Osorio
D000328:Adult; D000806:Angiotensin-Converting Enzyme Inhibitors / Q000737:chemistry*; D005260:Female; D005421:Flavoring Agents / Q000737:chemistry*; D005638:Fruit / Q000737:chemistry; D006801:Humans; D008297:Male; D008875:Middle Aged; D015394:Molecular Structure; D007703:Peptidyl-Dipeptidase A / Q000737:chemistry; D032322:Solanum / Q000737:chemistry*; D013095:Spermidine / Q000737:chemistry*; D013649:Taste; D055815:Young Adult
D000806:Angiotensin-Converting Enzyme Inhibitors; D005421:Flavoring Agents; D007703:Peptidyl-Dipeptidase A; D013095:Spermidine
ACE-inhibitory activity; Solanaceae; antihypertensive activity; bitterness; molecular docking