Proanthocyanidins with a Low Degree of Polymerization are Good Inhibitors of Digestive Enzymes Because of their Ability to form Specific Interactions: A Hypothesis

Abstract

Inhibition of target digestive enzymes is an accepted strategy to prevent diseases such as obesity and diabetes. Proanthocyanidins (PACs) are known for their ability to bind, inhibit, and precipitate enzymes, which makes them potential bioDrugs with an impact on the digestive process. PAC degree of polymerization (DP) is one of the structural features responsible for their differential inhibitory potency but the explanation for this phenomenon is still unclear. Pecan nut (Carya illinoinensis L.) kernels and nutshells are rich in oligomeric and polymeric PACs. We have used thiolysis and HPLC analyses to propose four theoretical model structures of PACs representative of four semipurified fractions obtained from pecan kernel and shell, which showed different inhibitory activity against intestinal lipases, amylases, and proteases. The noncovalent interactions between PACs and digestive enzymes were predicted by in silico methods through computational software. These observations are discussed in view of current literature on the biological effects of PACs with different DPs and allowed us to propose the hypothesis that "small oligomeric PACs could be digestive enzyme inhibitors due to their capacity to enter and bind the enzymes' specific cavities better than polymers and oligomers of medium and high molecular weight."

Variation in the pH of experimental diets affects the performance of Lymantria dispar asiatica larvae and its gut microbiota

“…Variation in diet composition/quality influences many pre-and postdigestive processes, including the activity of digestive enzymes in gypsy moth larvae (Milanović et al, 2016) which is also family-specific (Mrdakovic et al, 2013). In addition, many compounds of plant origin help in defending against the invasion of herbivores insects through influence on digestive enzyme activities (Ivashov, Simchuk, & Medvedkov, 2001;Mehrabadi, Bandani, Mehrabadi, & Alizadeh, 2012;Oliveira et al, 2007;Rekha, Sasikiran, & Padmaja, 2004;Vazquez Flores et al, 2018). Therefore, to identify potential targets for pest control, it is important to expand our understanding of the digestive enzymes (Rodrigues Macedo & Das Gracas Machado Freire, 2011).…”

Is Chickpea a Potential Substitute for Soybean? Phenolic Bioactives and Potential Health Benefits

“…It has been extensively reported that phenolic acids show lower inhibitory activity than flavonoids and that the activity of phenolic acids increases with the number of hydroxyl groups present in their structure [231]. In the case of polymeric compounds (condensed tannins), oligomeric structures (<10 monomeric units) show higher inhibitory activity compared to polymeric structures (>10 monomeric units) and monomeric phenolic compounds, probably because oligomeric structures are able to form specific interactions with the active site of the enzyme, while bigger structures form non-specific interactions within all the enzyme surface [258] and monomeric compounds form less or weaker interactions. Interestingly, a synergic effect of monomeric phenolic compounds and condensed tannins with different degree of polymerization from black bean extracts has been reported for the inhibition of α-amylase, α-glucosidase, and lipase [242].…”

The Sorbus spp.—Underutilised Plants for Foods and Nutraceuticals: Review on Polyphenolic Phytochemicals and Antioxidant Potential

“…Underutilised plants have become of a particular interest in the era of functional foods, nutraceuticals and personalized nutrition. Thus, natural bioactive compounds can play the most important role in the development of health promoting products based on individual genome and/or microbiome [ 1 , 2 ].…”