TY - JOUR
T1 - Spermidine derivatives in lulo (Solanum quitoense Lam.) fruit
T2 - Sensory (taste) versus biofunctional (ACE-inhibition) properties
AU - Forero, Diana Paola
AU - Masatani, Chieko
AU - Fujimoto, Yoshinori
AU - Coy-Barrera, Ericsson
AU - Peterson, Devin G.
AU - Osorio, Coralia
PY - 2016/7/6
Y1 - 2016/7/6
N2 - 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, N1,N4,N8-tris(dihydrocaffeoyl)spermidine and N1,N8-bis(dihydrocaffeoyl)spermidine, were isolated and their structures confirmed by analysis of their HPLC-ESI/MS and 1H and 13C NMR data. The N1,N4,N8-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.
AB - 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, N1,N4,N8-tris(dihydrocaffeoyl)spermidine and N1,N8-bis(dihydrocaffeoyl)spermidine, were isolated and their structures confirmed by analysis of their HPLC-ESI/MS and 1H and 13C NMR data. The N1,N4,N8-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.
KW - ACE-inhibitory activity
KW - Solanaceae
KW - antihypertensive activity
KW - bitterness
KW - molecular docking
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U2 - 10.1021/acs.jafc.6b01631
DO - 10.1021/acs.jafc.6b01631
M3 - Article
C2 - 27292771
AN - SCOPUS:84978120362
SN - 0021-8561
VL - 64
SP - 5375
EP - 5383
JO - Journal of Agricultural and Food Chemistry
JF - Journal of Agricultural and Food Chemistry
IS - 26
ER -