Chemical Characterization of Different Products from the Tunisian Opuntia ficus-indica (L.) Mill.

Various dried (by-)products from the Tunisian O. ficus-indica were elucidated for their proximate composition, fatty acid (FA) composition, inorganic elements, sugars, and polyphenols. Nopal and prickly pear peel and seeds were abundant in fiber (respectively, 28.39, 12.54, and 16.28%). Seeds had also high protein (17.34%) and may be source of an edible oil, due to lipids (9.65%) poor in saturated FAs (14.12%) and rich in linoleic acid (61.11%). Nopal and peel showed the highest levels of Mg (493.57 and 345.19 mg/100 g), K (6949.57 and 1820.83 mg/100 g), Mn (59.73 and 46.86 mg/Kg) and Fe (23.15 and 15.23 mg/Kg), while the fruit pulp predominantly constituted of sugars, glucose and arabinose being predominant (42.57 and 13.56 g/100 g). Total polyphenols widely varied among the Opuntia products (108.36–4785.36 mg GAE/100 g), being mainly represented by hydroxycinnamic and hydroxybenzoic acids, and flavonoids as well. In particular, peel may be revalorized for these valuable bioactives, including 4-hydroxybenzoic acid (484.95 mg/100 g), cinnamic acid (318.95 mg/100 g), rutin (818.94 mg/100 g), quercetin (605.28 mg/100 g), and several isorhamnetin and kaempferol glycosides. Overall, the Tunisian prickly pear cactus could encourage a sustainable production, an effective waste management, and may provide several benefits for human health, in accordance with the model of the Mediterranean diet.

Effect of Must Hyperoxygenation on Sensory Expression and Chemical Composition of the Resulting Wines

This paper evaluates the effect of must hyperoxygenation on final wine. Lower concentrations of caftaric acid (0.29 mg·L−1), coutaric acid (1.37 mg·L−1) and Catechin (0.86 mg·L−1) were observed in hyperoxygenated must in contrast to control must (caftaric acid 32.78 mg·L−1, coutaric acid 5.01 mg·L−1 and Catechin 4.45 mg·L−1). In the final wine, hydroxybenzoic acids were found in higher concentrations in the control variant (gallic acid 2.58 mg·L−1, protocatechuic acid 1.02 mg·L−1, vanillic acid 2.05 mg·L−1, syringic acid 2.10 mg·L−1) than in the hyperoxygenated variant (2.01 mg·L−1, 0.86 mg·L−1, 0.98 mg·L−1 and 1.50 mg·L−1 respectively). Higher concentrations of total flavanols (2 mg·L−1 in hyperoxygenated must and 21 mg·L−1 in control must; 7.5 mg·L−1 in hyperoxygenated wine and 19.8 mg·L−1 in control wine) and polyphenols (97 mg·L−1 in hyperoxygenated must and 249 mg·L−1 in control must; 171 mg·L−1 in hyperoxygenated wine and 240 mg·L−1 in control wine) were found in both the must and the control wine. A total of 24 volatiles were determined using gas chromatography mass spectrometry. Statistical differences were achieved for isobutyl alcohol (26.33 mg·L−1 in control wine and 32.84 mg·L−1 in hyperoxygenated wine), or 1-propanol (7.28 mg·L−1 in control wine and 8.51 mg·L−1 in hyperoxygenated wine), while esters such as isoamyl acetate (1534.41 µg·L−1 in control wine and 698.67 µg·L−1 in hyperoxygenated wine), 1-hexyl acetate (136.32 µg·L−1 in control wine and 71.67 µg·L−1 in hyperoxygenated wine) and isobutyl acetate (73.88 µg·L−1 in control wine and 37.27 µg·L−1 in hyperoxygenated wine) had a statistically lower concentration.

Chemical Composition and Polyphenolic Compounds of Red Wines: Their Antioxidant Activities and Effects on Human Health—A Review

Red wine, an alcoholic beverage is composed of a spectrum of complex compounds such as water, alcohol, glycerol, organic acid, carbohydrates, polyphenols, and minerals as well as volatile compounds. Major factors that affect the levels of phenolic compounds in red wines are the variety of grapes and the storage of the wines. Among the constituents of red wine, phenolic compounds play a crucial role in attributes including color and mouthfeel and confer beneficial properties on health. Most importantly, phenolic compounds such as flavanols, flavonols, flavanones, flavones, tannins, anthocyanins, hydroxycinnamic acids, hydroxybenzoic acids, and resveratrol can prevent the development of cardiovascular diseases, cancers, diabetes, inflammation, and some other chronic diseases.

Potential of Hydroxybenzoic Acids From Graptopetalum paraguayense for Inhibiting of Herpes Simplex Virus DNA Polymerase – Metabolome Profiling, Molecular Docking and Quantum-chemical Analysis

According to our previous investigation the total methanol extract from Graptopetalum paraguayense E. Walther demonstrates a significant inhibitory effect on HSV-1. To clarify what causes this inhibitory activity on HSV-1, a metabolic profile of the plant was performed. Three main fractions: non-polar substances, polar metabolites and phenolic compounds were obtained and GC-MS analysis was carried out. Since it is well known that phenolic compounds show a significant anti-herpes effect and that viral DNA polymerase (DNApol) appears to play a key role in HSV virus replication, we present a docking and quantum-chemical analysis of the binding of these compounds to viral DNApol amino acids. Fourteen different phenolic acids found by GS/MS analyses, were used in molecular docking simulations. According to the interaction energies of all fourteen ligands in the DNApol pockets based on docking results, DFT calculations were performed on the five optimally interacting with the receptor acids. It was found that hydroxybenzoic acids from phenolic fraction of Graptopetalum paraguayense E. Walther show a good binding affinity to the amino acids from the active site of the HSV DNApol, but significantly lower than that of acyclovir. The mode of action on virus replication of acyclovir (by DNApol) is different from that of the plant phenolic acids one, probably.

Phenolic Profile and Antioxidant Capacity of Selected Medicinal and Aromatic Plants: Diversity upon Plant Species and Extraction Technique

Phenolic content and antioxidant capacity (AC) was evaluated in extracts of bay, sage and thyme leaves, myrtle leaves and berries, and sea buckthorn berries obtained by conventional (CE) and advanced extraction techniques [ultrasound-assisted (UAE) and accelerated solvent extraction (ASE)] using 80% acetone (v/v) as extraction solvent. Extracts were analyzed for phenolic content using UPLC/ESI MS2 and AC by ORAC method. Results indicated the variations in the phenolic composition and concentrations among analyzed plant species and applied extraction methods. Flavonoids showed to be the predominant phenolic group represented by flavonols kaemferol-3-O-hexoside (182.58–321.45 mg 100−1 g dm) and quercetin-3-glucoside (253.05–315.67 mg/100 g dm) in bay leaves, by flavonol isorhamnetine-3-O-hexoside (27.76–45.16 mg/100 g dm) in sea buckthorn berries and by flavone luteolin-7-O-glucoside (470.27–781.78 mg/100 g dm) in sage leaves. Among the phenolic acids, hydroxybenzoic acids and their derivates were the predominant phenolic group in thyme leaves and myrtle. Statistical analysis showed that ASE contributed to the highest content of total flavonols, flavones, hydroxycinnamic and hydroxybenzoic acids as well as AC. CE was more efficient method for the extraction of total flavan-3-ols, while UAE showed the highest efficiency in extraction of total anthocyanins. Analyzed plant extracts proved to be a rich source of various phenolics and results indicated suitable extraction methods for target phenolic compounds characteristic for certain plant species.

Potential of Hydroxybenzoic Acids from Graptopetalum paraguayense for Inhibiting of Herpes Simplex Virus DNA Polymerase – Metabolome Profiling, Molecular Docking and Quantum-chemical Analysis

According to our previous investigation the total methanol extract from Graptopetalum paraguayense E. Walther demonstrates a significant inhibitory effect on HSV-1. To clarify what causes this inhibitory activity on HSV-1, a metabolic profile of the plant was performed. Three main fractions: non-polar substances, polar metabolites and phenolic compounds were obtained and GC-MS analysis was carried out. Since it is well known that phenolic compounds show a significant anti-herpes effect and that viral DNA polymerase (DNApol) appears to play a key role in HSV virus replication, we present a docking and quantum-chemical analysis of the binding of these compounds to viral DNApol amino acids. Fourteen different phenolic acids found by GS/MS analyses, were used in molecular docking simulations. According to the interaction energies of all fourteen ligands in the DNApol pockets based on docking results, DFT calculations were performed on the five optimally interacting with the receptor acids. It was found that hydroxybenzoic acids from phenolic fraction of Graptopetalum paraguayense E. Walther show a good binding affinity to the amino acids from the active site of the HSV DNApol, but significantly lower than that of acyclovir. The mode of action on virus replication of acyclovir (by DNApol) is different from that of the plant phenolic acids one, probably.

Identification and Quantification of Naphthoquinones and Other Phenolic Compounds in Leaves, Petioles, Bark, Roots, and Buds of Juglans regia L., Using HPLC-MS/MS

The present study was designed to identify and quantify the major phenolic compounds in different Juglans regia L. (common walnut) tissues (leaves, petioles, bark, roots, buds), to define the compositions and contents of phenolic compounds between these tissues. A total of 91 individual phenolic compounds were identified and quantified, which comprised 8 hydroxycinnamic acids, 28 hydroxybenzoic acids, 11 flavanols, 20 flavonols, 22 napthoquinones, and 2 coumarins. Naphthoquinones were the major phenolic group in leaves, petioles, bark, and buds, as >60% of those identified, while hydroxybenzoic acids were the major phenolic group in side roots, as ~50% of those identified. The highest content of phenolic compounds was in the J. regia main root, followed by side roots and buds, leaves, and 1-year-old bark; the lowest content was in petioles and 2-year-old bark. Leaves, roots, and buds of J. regia represent a valuable source of these agro-residues.

Plant-Derived and Dietary Hydroxybenzoic Acids—A Comprehensive Study of Structural, Anti-/Pro-Oxidant, Lipophilic, Antimicrobial, and Cytotoxic Activity in MDA-MB-231 and MCF-7 Cell Lines

Seven derivatives of plant-derived hydroxybenzoic acid (HBA)—including 2,3-dihydroxybenzoic (2,3-DHB, pyrocatechuic), 2,4-dihydroxybenzoic (2,4-DHB, β-resorcylic), 2,5-dihydroxybenzoic (2,5-DHB, gentisic), 2,6-dihydroxybenzoic (2,6-DHB, γ-resorcylic acid), 3,4-dihydroxybenzoic (3,4-DHB, protocatechuic), 3,5-dihydroxybenzoic (3,5-DHB, α-resorcylic), and 3,4,5-trihydroxybenzoic (3,4,5-THB, gallic) acids—were studied for their structural and biological properties. Anti-/pro-oxidant properties were evaluated by using DPPH• (2,2-diphenyl-1-picrylhydrazyl), ABTS•+ (2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid), FRAP (ferric-reducing antioxidant power), CUPRAC (cupric-reducing antioxidant power), and Trolox oxidation assays. Lipophilicity was estimated by means of experimental (HPLC) and theoretical methods. The antimicrobial activity against Escherichia coli (E. coli), Pseudomonas aeruginosa (P. aeruginosa), Staphylococcus aureus (S. aureus), Bacillus subtilis (B. subtilis), Salmonella enteritidis (S. enteritidis), and Candida albicans (C. albicans) was studied. The cytotoxicity of HBAs in MCF-7 and MDA-MB-231 cell lines was estimated. Moreover, the structure of HBAs was studied by means of experimental (FTIR, 1H, and 13C NMR) and quantum chemical DFT methods (the NBO and CHelpG charges, electrostatic potential maps, and electronic parameters based on the energy of HOMO and LUMO orbitals). The aromaticity of HBA was studied based on the calculated geometric and magnetic aromaticity indices (HOMA, Aj, BAC, I6, NICS). The biological activity of hydroxybenzoic acids was discussed in relation to their geometry, the electronic charge distribution in their molecules, their lipophilicity, and their acidity. Principal component analysis (PCA) was used in the statistical analysis of the obtained data and the discussion of the dependency between the structure and activity (SAR: structure–activity relationship) of HBAs. This work provides valuable information on the potential application of hydroxybenzoic acids as bioactive components in dietary supplements, functional foods, or even drugs.