Phenolic Compounds and Capsaicinoids in Three Capsicum annuum Varieties: From Analytical Characterization to In Silico Hypotheses on Biological Activity

Abstract

The affinity of specific phenolic compounds (PCs) and capsaicinoids (CAPs) present in three Capsicum annuum varieties (Friariello, Cayenne and Dzuljunska Sipka) to the transient receptor potential vanilloid member 1 (TRPV1) was investigated by integrating an analytic approach for the simultaneous extraction and analysis through high-performance liquid chromatography coupled with ion trap mass spectrometry (HPLC/ITMS) and UV detection (HPLC-UV) of PCs and CAPs and structural bioinformatics based on the protein modelling and molecular simulations of protein–ligand docking. Overall, a total of 35 compounds were identified in the different samples and CAPs were quantified. The highest content of total polyphenols was recorded in the pungent Dzuljunska Sipka variety (8.91 ± 0.05 gGAE/Kg DW) while the lowest was found in the non-pungent variety Friariello (3.58 ± 0.02 gGAE/Kg DW). Protein modelling generated for the first time a complete model of the homotetrameric human TRPV1, and it was used for docking simulations with the compounds detected via the analytic approach, as well as with other compounds, as an inhibitor reference. The simulations indicate that different capsaicinoids can interact with the receptor, providing details on the molecular interaction, with similar predicted binding energy values. These results offer new insights into the interaction of capsaicinoids with TRPV1 and their possible actions.

Interaction Between Salicylic or Ferulic Acid and Cellulase Used to Produce Phenolic Compounds Aggregates from “Jalapeño” (Capsicum AnnumL.) Chili Pepper Seeds

“…Herrera-Pool et al obtained extracts from chili pepper leaves ( Capsicum chinense ) with a TPC content of 2.92 mg GAE/g ext using n -hexane as the organic solvent. Otherwise, Giordano et al . obtained a TPC content of 3.58 mg GAE/g ext in 80% aqueous methanol extracts of chili pepper ( C.…”

“…Herrera-Pool et al 16 obtained extracts from chili pepper leaves (Capsicum chinense) with a TPC content of 2.92 mg GAE/g ext using n-hexane as the organic solvent. Otherwise, Giordano et al 17 obtained a TPC content of 3.58 mg GAE/g ext in 80% aqueous methanol extracts of chili pepper (C. annuum). These were lower contents than the results obtained using EAE in our study, demonstrating that it is a green alternative for industrial purposes.…”

Structural and Functional Characterization of Lipoxygenases from Diatoms by Bioinformatics and Modelling Studies

“…Therefore, we adopted a strategy to model LOXs of Fragilariopsis cylindrus and Pseudo-nitzschia arenysensis with the correct active conformation features, and then used these models as a template for modelling the other LOX sequences. Similar procedures are routinely applied in our laboratory for several protein models’ construction and investigation (for a recent example, see [ 37 ]). In detail, the crystallographic structure of the allene oxide synthase-lipoxygenase protein from Plexaura homomalla (PDB code: 3FG1) and of the lipoxygenase 3 from Glycine max (PDB code: 1HU9) have been used as templates for modelling the LOX sequences isolated from Fragilariopsis cylindrus and Pseudo-nitzschia arenysensis , respectively.…”

Assessment of the Effects of Roasting, Contact Grilling, Microwave Processing, and Steaming on the Functional Characteristics of Bell Pepper (Capsicum annuum L.)

“…Polyphenols present in the diet have also been shown to help modify the blood lipid profile, normalize blood pressure, reduce insulin resistance, and reduce systemic inflammation [ 6 , 7 ], while the consumption of polyphenols such as quercetin and resveratrol has been linked to improved cardiovascular function [ 8 ]. Analyses using high-performance liquid chromatography coupled with tandem mass spectrometry and electrospray ionization (HPLC-ITMS) techniques have enabled the identification of a number of polyphenolic compounds in Capsicum annuum fruits, such as caffeic acid, coumaric acid, coumaroylquinic acid, 3- O -caffeoylquinic acid, ferulic acid, sinapic acid, apigenin- O -hexoside, and quercetin- O -rhamnosyl- O -hexoside [ 9 ]. The health-promoting and therapeutic potential of polyphenols present in the diet is also closely linked to the functioning of the gut microbiome, which converts polyphenolic compounds into a form that is highly bioactive and bioavailable [ 10 , 11 ].…”