Search results for "Phenols"

Conformational Switching of Multi-Responsive Ferrocenyl-Phenol Conjugates

2016

Multifunctional conformational switches based on the ferrocenyl-salicylic acid amide motif with increasing additional complexity at the Fc moiety (R = COOMe, CONHEt, CONHFc; H-2–H-4; Fc = ferrocenyl) have been prepared and their preferred secondary structures in solution have been elucidated by NMR and IR spectroscopy in combination with conformational searches based on DFT calculations. Their distinct conformational responses to deprotonation ([2]––[4]–) and oxidation ([H-2]+·–[H-4]+·) have been revealed by IR, EPR, and UV/Vis spectroscopy as well as by DFT calculations. Deprotonation inverts all amide units (double amide twist) whereas oxidation selectively flips the terminal amide unit (…

Metal- and Reagent-Free Anodic C−C Cross-Coupling of Phenols with Benzofurans leading to a Furan Metathesis

2018

Heterobiaryls consisting of a phenol and a benzofuran motif are of significant importance for pharmaceutical applications. An attractive sustainable, metal- and reagent-free, electrosynthetic, and highly efficient method, that allows access to (2-hydroxyphenyl)benzofurans is presented. Upon the electrochemical dehydrogenative C-C cross-coupling reaction, a metathesis of the benzo moiety at the benzofuran occurs. This gives rise to a substitution pattern at the hydroxyphenyl moiety which would not be compatible by a direct coupling process. The single-step protocol is easy to conduct in an undivided electrolysis cell, therefore scalable, and inherently safe.

Catalytic Carbonylative Double Cyclization of 2-(3-Hydroxy-1-yn-1-yl)phenols in Ionic Liquids Leading to Furobenzofuranone Derivatives

2019

A catalytic carbonylative double cyclization method for the synthesis of furo[3,4-b]benzofuran-1(3H)-ones is reported. It is based on the reaction between readily available 2-(3-hydroxy-1-yn-1-yl)phenols, CO, and oxygen carried out in the presence of catalytic amounts of PdI2 (1 mol %) in conjunction with KI (20 mol %) and 2 equiv of diisopropylethylamine at 80 degrees C for 24 h under 30 atm of a 1:4 mixture of CO-air. Interestingly, the process was not selective when carried out in classical organic non-nucleophilic solvents (such as MeCN or DME), leading to a mixture of the benzofurofuranone derivative and the benzofuran ensuing from simple cycloisomerization, whereas it turned out chemo…

2020

Teraryl-based alpha-helix mimetics have resulted in efficient inhibitors of protein-protein interactions (PPIs). Extending the concept to even longer oligoarene systems would allow for the mimicking of even larger interaction sites. We present a highly efficient synthetic modular access to quateraryl alpha-helix mimetics, in which, at first, two phenols undergo electrooxidative dehydrogenative cross-coupling. The resulting 4,4′-biphenol is then activated by conversion to nonaflates, which serve as leaving groups for iterative Pd-catalyzed Suzuki-cross-coupling reactions with suitably substituted pyridine boronic acids. This work, for the first time, demonstrates the synthetic efficiency of …

Post-harvest Industrial Processes of Almond (Prunus dulcis L. Mill) in Sicily Influence the Nutraceutical Properties of By-Products at Harvest and Du…

2021

Almond cultivation in Sicily is experiencing a phase of great interest which is mainly concentrated in the development of specialized orchards, with irrigation and by adopting cultivars with high qualitative and quantitative performances. These are mostly Mediterranean genotypes with high fat content and hard or semi-hard shell, extremely different from the varieties of Californian diffusion. The development of the sector comprises the primary production of almonds but also a series of secondary products which often represent a burden for the company. From these considerations several researches have been developed with the aim of giving a value to these by-products through circular economy…

Laccases of Botrytis cinerea

2017

Phenolic compounds significantly affect the color, odor and taste of wine. Due to their presumptive beneficial impact on human health, polyphenols in red wine have gained increasing public and scientific interest. Wine phenols are extremely sensitive to oxygen and are easily converted to brownish oxidation products accompanied by loss of nutritive values of the wine. Enzymatic oxidation takes place under the influence of polyphenoloxidases including tyrosinases and laccases. The latter are produced by the phytopathogenic fungus Botrytis cinerea and enter the must with contaminated berries. Although uncontrolled action of Botrytis-laccase has a dramatic impact on wine quality, the oxidative …

Spoilage potential of Brettanomyces bruxellensis strains isolated from Italian wines

2018

Abstract Brettanomyces bruxellensis is an important wine spoilage agent. In this study a population of Brettanomyces strains isolated from Italian wines was thoroughly investigated to evaluate adaptability to wine conditions and spoilage potential. The presumptive isolates of Brettanomyces were identified at species level with 26S rRNA gene sequencing and species-specific PCR, and subsequently subjected to analysis of intra-species variability through the study of intron splice sites (ISS-PCR). Although, some strains were tracked in wines from different regions, extensive genetic biodiversity was observed within the B. bruxellensis population investigated. All strains were evaluated for the…

High‐power ultrasound altered the polyphenolic content and antioxidant capacity in cloudy apple juice during storage

2019

The aim was to investigate the influence of high‐power ultrasound treatment (HPU) on polyphenolic stability and antioxidant capacity in cloudy apple juice during 7 days of storage at 4°C. HPU (100 W, 30 kHz frequency) was operated at: (i) amplitude 40 versus 80%, (ii) the probe diameter 7 versus 10 mm, and (iii) treatment time of 3, 6, and 9 min. Total phenols (TP), total flavan‐3‐ols (TFL), and in vitro antioxidant capacity (DPPH and FRAP) were determined spectrophotometrically. Findings revealed that HPU significantly decreased TP, TFL, and antioxidant capacity in the samples. However, results indicated that examined sonication parameters, represented as the probe diameter and treatment t…

A one step enhanced extraction and encapsulation system of cornelian cherry (Cornus mas L.) polyphenols and iridoids with β-cyclodextrin

2021

Abstract The objective of this study was simultaneous extraction and encapsulation of cornelian cherry active principles. As an encapsulating agent, β-cyclodextrin (β-CD) was used to enhance the ultrasound-assisted extraction of cornelian cherry polyphenols and iridoids. Lyophilized cornelian cherry fruit was extracted by four different solvents: pure water, 50% aqueous ethanol (conventional system), 1.5% β-CD water solution and 1.5% β-CD aqueous ethanol solution. The highest enhancement of the extraction efficiency was observed for flavonoids and anthocyanins, especially for cyaniding 3-galactoside and pelargonidin 3-galactoside. Water-ethanolic extract was used to form inclusion complexes…

Sicilian Myrtle Diversity: Evaluation of Leaf Total Phenols Content and Antioxidant Properties

2017

Myrtle (Myrtus communis L.) is an aromatic plant spontaneously growing and increasingly cultivated in Mediterranean area. Recently, interest on myrtle plant is growing due to the pharmacological and antioxidant properties since myrtle leaves are important sources of phenolic and antioxidant compounds with health-promoting effects. Plant genotype is the primary factor affecting antioxidant activity and phenol content. For this reason, a core collection of local selected myrtle accessions from Sicily was evaluated with the aim to identify genotypes with high antioxidant value. Thirty-six myrtle individuals belonging to seven populations were studied for leaf total phenols, tannins and antioxi…