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Abstract

Phenolic compounds comprise a broad class of natural products formed mainly by plants, but also microorganisms and marine organisms that have the capacity to form them. Nowadays the interest in these compounds has increased mainly due to their diverse chemical structure and wide biological activity valuable in the prevention of some chronic or degenerative diseases. The functional foods are a rich source of these phytochemicals, and this is the starting point for this book, which shows the state of the art of the phenolic compounds and their biological activity. This book integrates eleven chapters that show the state of the art of diverse biological activity of the phenolic compounds, present in some crops or fruits.
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... activity [31]. Epicatechin has a beneficial role in diabetic patients as it reduces the blood glucose levels and chlorogenic acid, lowers cholesterol, and triglyceride levels, and improves obesity-related hormone levels [32], whereas the flavonoid myricetin was present in both the stages of fruit, quercetin, luteolin, and apigenin were only found in ripe fruits. ...
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Quorum sensing controls bacterial virulence through signaling molecules, which plays a vital role in managing foodborne pathogens that cause food spoilage and human infections. Though many synthetic compounds have been used to control infection, antibiotic resistance has become a global issue. Targeting the bacterial quorum sensing using the bioactive compounds could be an alternative strategy to combat their resistance. In this context, polyphenols from an unexplored unripe and ripe fruits of Carissa spinarum were evaluated for anti-quorum sensing activity. The study aimed at determining nutritional, phytochemical composition, and polyphenol profiling to evaluate their antioxidant potential of the fruit. Furthermore, the violacein inhibition, anti-biofilm, and effect on the motility of foodborne pathogens were also studied. The phytochemical content of C. spinarum fruit showed the phenolic and flavonoid content 273.20 mg GAE/100 g and 453.78 mg QE/100 g fresh weight , respectively, in ripe fruit. HPLC characterization of fruit extracts showed high content of syringic acid, resveratrol, and quercetin in ripe, whereas it showed epicatechin and gentisic acid in unripe fruit. The antioxidant activity of the ripe fruit extract exhibited a higher potential to scavenge DPPH radicals with IC50 4.69 mg/mL. Further, the anti-quorum sensing activity was higher in ripe fruit extract at 1.8 mg/mL inhibited with 78.65% violacein production in Chromobacterium violaceum, swimming motility, and biofilm formation in Pseudomonas aeruginosa and Yersinia enterocolitica (66.25% and 59.36% respectively at 1.2 mg/mL). Hence C. spinarum fruit bioactive could be a natural plant source for anti-quorum sensing activity to manage foodborne pathogens over synthetic compounds.
... Phenolic compounds (phenolic acids, coumarins, flavonoids and tannins), alkaloids and terpenoids, found in plants, have considerable interest in pharmacology (Zillich et al., 2015;Xu et al., 2017;Tanase et al., 2019). The use of polyphenols has become increasingly preferred thanks to their antioxidant, anti-inflammatory (Soto-Hernández et al., 2017;Vaga et al., 2018), anti-diabetics (Duru et al., 2018) and hypocholesterolemic properties (El-Sayyad et al., 2015). Herbal medicine, in Algeria, is an integral part of local culture, population has an important indigenous knowledge, acquired empirically through the generations. ...
Article
Zygophyllum album (Z. album) is an endemic plant in Algeria and is known for its medicinal properties since long times. This study assess Z. album extract supplementation effects on protein oxidation and endothelial dysfunc-tion tissues in rats rendered hypercholesterolemic-diabetic. Male Wistar rats (n=36), weighing 200±10 g were divided into three groups (n=12). The first group was rendered hypercholesterolemic with an enriched cholesterol diet (1 %) (HC). The second group was rendered diabetic by intraperitoneal injection of streptozotocin (STZ) (35 mg/kg of body weight) (D). The third group was hypercholesterolemic and diabetic (HC-D); each group was divided into two groups (n=6), untreated groups (HC, D, HC-D) and treated groups with 1 % Z. album extract (HC-Za, D-Za and HC-D-Za). At d28 of the experiment, Z. album treatment lead to a similar weight growth in HC-Za vs HC and HC-D-Za vs HC-D, while was increased in D-Za vs D (+35 %); similarly, food intake was increased by +17 %. An increase in glutathione (GSH) levels was noted in liver, heart and adipose tissue (p <0.05). Therefore,reduced carbonyls tissue concentrations after Z. album supplementation in HC-Za, D-Za and HC-D-Za was noted; there was respectively a decrease by-38,-52 and-46 % in liver;-36,-32 and-35 % in kidneys and-27,-39 and-27 %, in adipose tissue. An increase in nitric monoxide (NO) levels was observed in all treated groups (p <0.05). In conclusion Z. album stimulates GSH synthesis, attenuates protein oxidation and protects endothelial function in hypercho-lesterolemic-diabetic rats.
... Polyphenols are commonly found in nature and demonstrate a remarkable range of biological activities (Harborne et al., 1999;Whitting, 2001;Dai and Mumper, 2010;Oksana et al., 2012;De Arias et al., 2012;Soto-Hernandez et al., 2017). The potent in vitro and in vivo pharmacological activity of the 2,5,4 0 -trihydrox ybibenzyl against Leishmania spp. was reported (Roldos et al., 2008;Serna et al., 2015). ...
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Development of new antimicrobial agents, capable of combating resistant and multidrug-resistant fungal and bacterial clinical strains, is necessary. This study presents the synthesis and antimicrobial screening of 42 2-substituted-1,4-benzenediols, being 10 novel compounds. In total, 23 compounds showed activity against fungi and/or bacteria. Benzenediol compounds 2, 5, 6, 8, 11, and 12 demonstrated broad spectrum antimicrobial actions, including resistant and multidrug-resistant species of dermatophytes (Trichophyton mentagrophytes), Candida spp. and the ESKAPE panel of bacteria. Minimum inhibitory concentrations of these compounds for fungi and bacterial strains ranged from 25 to 50 µg/ml and 8–128 µg/ml, respectively. The antifungal mechanism of action is related to the fungal cell wall of dermatophytes and membrane disruption to dermatophytes and yeasts, in the presence of compound 8. Specific structural changes, such as widespread thinning along the hyphae and yeast lysis, were observed by scanning electron microscopy. The effects of compound 8 on cell viability are dose-dependent; however they did not cause genotoxicity and mutagenicity in human leukocyte cells nor haemolysis. Moreover, the compounds were identified as nonirritant by the ex-vivo Hen’s egg test-chorioallantoic membrane (HET-CAM). The furan-1,4-benzenediol compound 5 showed in vivo efficacy to combat S. aureus infection using embryonated chicken eggs. Therefore, the compounds 8, and 5 are promising as hits for the development of new antimicrobial drugs with reduced toxicity. Keywords: Fungi, ESKAPE pathogens, 1,4-benzenediol derivatives, Antimicrobial activity, Mechanism of action, Toxicity
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Phenols ( I ) are extremely relevant chemical functionalities in natural, synthetic and industrial chemistry. Their corresponding electron‐rich anions, namely phenolates ( I ), are characterized by interesting physicochemical properties that can be drastically altered upon light excitation. Specifically, phenolates ( I ) become strong reducing agents in the excited state and are able to generate reactive radicals from suitable precursors via single‐electron transfer processes. Thus, these species can photochemically trigger strategic bond‐forming reactions, including their direct aromatic C‐H functionalization. Moreover, substituted phenolate anions can act as photocatalysts to enable synthetically useful organic transformations. An alternative mechanistic manifold is represented by the ability of phenolate derivatives I to form ground state electron donor‐acceptor (EDA) complexes with electron‐poor radical sources. These complementary scenarios have paved the way for the development of a wide range of relevant organic reactions. In this Minireview, we present the main examples of this research field, and give insight on emerging trends in phenols photocatalysis towards richer organic synthesis.
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Industrial hemp (Cannabis sativa L.) represents an important plant, used for a variety of uses including pharmaceutical and nutraceutical purposes. As such, a detailed characterization of the composition of this plant could help future research to further exploit the beneficial effects of hemp compounds on the human health. Among the many compounds of hemp, fatty acids represent an interesting class of minor components, which has been overlooked so far. In this work, an untargeted approach based on liquid-chromatography coupled to a high-resolution mass spectrometry and a dedicated structure-based workflow for raw data interpretation was employed for the characterization of fatty acids from hemp inflorescences. A simple method, without any chemical derivatization, was developed for extraction and characterization of fatty acids leading to the tentative identification of 39 fatty acid species in the five hemp samples. A quantitative analysis on the untargeted data was initially performed, using peak areas as surrogate of analyte abundance for relative quantitation. Five fatty acids resulted the most abundant in all hemp samples, with ca. 90% of the total peak area. For these compounds a targeted quantitative method was validated, indicating that the most abundant ones were linolenic acid (1.39-7.95 mg g-1) and linoleic acid (1.04-7.87 mg g-1), followed by palmitic acid (3.74-6.08 mg g-1), oleic acid (0.91-4.73 mg g-1) and stearic acid (0.64-2.25 mg g-1).
Conference Paper
The total phenolic compound is a huge contributor to antioxidant activity. Natural antioxidants provide no side effect to the user and is a better option as compared to synthetic antioxidant. This paper studied the single-factor optimisation of ultrasonic-assisted extraction (UAE) conditions of Citrus Hystix, also known as Kaffir Lime for the total phenolic content (TPC). The selected parameters to study were raw materials to solvent ratio (1:10 to 1:30), solvent concentration (40% to 80%), extraction temperature (30°C to 70°C), ultrasonic power (40% to 80%) and extraction time (30 min to 90 min). The extraction solvent used was ethanol and the TPC was tested using Folin-Ciocalteu method. The optimum levels of the UAE conditions were identified through single-factor analysis. Based on experimental results, the optimum raw materials to solvent ratio was 1:30, solvent concentration was 70%, extraction temperature was 50°C, ultrasonic power was 60% and extraction time was 45 min. Based on single-factor analysis, the most significant factor was raw materials to solvent ratio and the least significant factor was the extraction time.
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Twenty-nine flavonoid glycosides were identified in the aqueous extract (PC) of Petroselinum crispum var crispum leaves and apiin, the major compound, was isolated thereof. Apigenin was obtained (90% of purity) by hydrolysis of apiin. A high content of phenolics (12.49 ± 1.70 mg GAE/g of parsley extract - Folin-Ciocalteu method) and total flavonoids (15.05 ± 2.20 mg of quercetin equivalents/g of parsley extract - aluminum chloride method) were quantified in P. crispum, as well as high antioxidant activity (EC50 – 15.50 mg.mL-1, DPPH method) and (189.8 mM Fe (II)/mg of dry plant aqueous extract - FRAP method). In vivo analyzes with Saccharomyces cerevisiae cells showed low toxicity of the aqueous extract of parsley, however it revealed a high dose-dependent antioxidant potential, mainly in the lipoperoxidation assay. In addition, flavonoid apiin also showed antioxidant action on yeast cells under oxidative stress in the cell viability assay (0.1 mM) and lipid peroxidation (0.01 and 0.1 mM), while apigenin was slightly antioxidant. Therefore, it is likely that the antioxidant activity of apiin is related to the total antioxidant capacity of parsley.
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A method for protection of alcohols with vinyl groups is suggested and studied in detail. The procedures of protection and deprotection via vinylation and devinylation reactions are evaluated. Vinylation reaction is performed using cheap and convenient calcium carbide reagent. Stability of the vinyl group under various conditions is examined. The vinyl group is found to be stable under basic conditions and labile under acidic conditions. The vinyl protecting group shows high tolerance to functional groups and good compatibility with common synthetic reagents. Applicability of the procedure in the Suzuki and Sonogashira catalytic reactions and its flexible utilization in the reaction with Grignard reagent are demonstrated.
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Chiral phosphoric acids catalyzed biomimetic asymmetric [4+2]-cycloaddition of the ortho-alkenyl naphthols/phenols and ortho-quinone methides (o-QMs) has been demonstrated to afford various importance 2,3,4-trisubstituted chromans in high yields with excellent enantio- and diastereoselectivities (up to 99% yield, 98% ee, >20:1 dr). Notably, this methodology not only enabled access to the trans-cis chiral trisubstituted chromans from 1-alkenyl 2-naphthols, but also is compatible with 2-alkenyl 1-naphthols and phenols to deliver trans-trans chiral trisubstituted chroman.
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