Polyphenols have proven beneficial to human health, acting on risk factors for cancer, cardiovascular and neurodegenerative diseases, as well as on diabetes and osteoporosis. Information at the molecular level on the mechanistic and structural aspects of the interaction of bioactive polyphenols with possible target proteins is limited. Monomeric polyphenols – including stilbenoids - are particularly prone to oxidative coupling. The complex dimers and oligomers formed in these processes may be responsible for the beneficial effects of stilbene derivatives. Notably, most of the natural oligomers also present stereogenic centers, that could play a pivotal role in the interaction of this class of molecules with biological targets. In this study, individual stilbene derivatives were synthesized and used for the biological evaluation of the binding determinants and their effects as for: - inhibition of enzymes relevant to glucose metabolism (such as brush-border glucosidase and pancreatic α-amylase) - regulation of glucose uptake in a brush-border cell model - control of inflammatory response in a Caco-2 cell model - affecting the activity of digestive enzymes (pepsin, trypsin, and chymotrypsin) on various substrate proteins. Altogether, the results highlight the requirement for peculiar structural features of the various phenolics for specifically eliciting individual effects. Specific effects were indeed dependent on the polymerization state of the stilbenoids, their three-dimensional structure, and on the presence/absence of specific moieties in each individual species. In several cases, a combination of the aforementioned features was found to be required to elicit specific effects.
Molecular basis of the bioactivities of dietary polyphenols: a multi-pronged investigation on stilbene derivates / M. DI NUNZIO, G.C. Heinzl, S.M. Borgonovi, A. Pinto, S.M.D. Dallavalle, F. Bonomi, A. Scarafoni, S. Iametti. ((Intervento presentato al convegno Annual Meeting ‘Nutrition and Environment’ and ‘Membrane’ groups tenutosi a Ancona nel 2022.
Molecular basis of the bioactivities of dietary polyphenols: a multi-pronged investigation on stilbene derivates
M. DI NUNZIO
;G.C. Heinzl;S.M. Borgonovi;A. Pinto;S.M.D. Dallavalle;F. Bonomi;A. Scarafoni;S. Iametti
2022
Abstract
Polyphenols have proven beneficial to human health, acting on risk factors for cancer, cardiovascular and neurodegenerative diseases, as well as on diabetes and osteoporosis. Information at the molecular level on the mechanistic and structural aspects of the interaction of bioactive polyphenols with possible target proteins is limited. Monomeric polyphenols – including stilbenoids - are particularly prone to oxidative coupling. The complex dimers and oligomers formed in these processes may be responsible for the beneficial effects of stilbene derivatives. Notably, most of the natural oligomers also present stereogenic centers, that could play a pivotal role in the interaction of this class of molecules with biological targets. In this study, individual stilbene derivatives were synthesized and used for the biological evaluation of the binding determinants and their effects as for: - inhibition of enzymes relevant to glucose metabolism (such as brush-border glucosidase and pancreatic α-amylase) - regulation of glucose uptake in a brush-border cell model - control of inflammatory response in a Caco-2 cell model - affecting the activity of digestive enzymes (pepsin, trypsin, and chymotrypsin) on various substrate proteins. Altogether, the results highlight the requirement for peculiar structural features of the various phenolics for specifically eliciting individual effects. Specific effects were indeed dependent on the polymerization state of the stilbenoids, their three-dimensional structure, and on the presence/absence of specific moieties in each individual species. In several cases, a combination of the aforementioned features was found to be required to elicit specific effects.Pubblicazioni consigliate
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