Antidiabetic and Anti-Inflammatory Potential of Sorbus Aucuparia Fruits (Rowanberries) from Romania

Quantitative analysis of polyphenolic antioxidants, as well as comparison of various methods for the extraction of phenolic compounds from corn puffed cereals, puffed cereals with an addition of chamomile (3, 5, 10 and 20%) and from [i]Chamomillae anthodium. [/i] [b]Materials and Methods[/b]. Two modern extraction methods - ultrasound assisted extraction (UAE) at 40 °C and 60 °C, as well as accelerated solvent extraction (ASE) at 100 °C and 120 °C were used for the isolation of polyphenols from functional food. Analysis of flavonoids and phenolic acids was carried out using reversed-phase high-performance liquid chromatography and electrospray ionization mass spectrometry (LC-ESI-MS/MS). [b]Results and Conclusions[/b]. For most of the analyzed compounds, the highest yields were obtained by ultrasound assisted extraction. The highest temperature during the ultrasonification process (60 °C) increased the efficiency of extraction, without degradation of polyphenols. UAE easily arrives at extraction equilibrium and therefore permits shorter periods of time, reducing the energy input. Furthermore, UAE meets the requirements of 'Green Chemistry'.

Chlorogenic acid is a major phenolic compound that forms a substantial part of plant foods and is an ester of caffeic acid and quinic acid. However, the effect of the structures of both chlorogenic and caffeic acids on their antioxidant and antidiabetic potentials have not been fully understood. Thus, this study sought to investigate and compare the interaction of caffeic acid and chlorogenic acid with α-amylase and α-glucosidase (key enzymes linked to type 2 diabetes) activities in vitro. The inhibitory effect of the phenolic acids on α-amylase and α-glucosidase activities was evaluated. Thereafter, their antioxidant activities as typified by their 1,1-diphenyl-2 picrylhydrazyl radical scavenging ability and ferric reducing antioxidant properties were determined. The results revealed that both phenolic acids inhibited α-amylase and α-glucosidase activities in a dose-dependent manner (2-8 μg/mL). However, caffeic acid had a significantly (p<0.05) higher inhibitory effect on α-amylase [IC50 (concentration of sample causing 50% enzyme inhibition)=3.68 μg/mL] and α-glucosidase (IC50=4.98 μg/mL) activities than chlorogenic acid (α-amylase IC50=9.10 μg/mL and α-glucosidase IC50=9.24 μg/mL). Furthermore, both phenolic acids exhibited high antioxidant properties, with caffeic acid showing higher effects. The esterification of caffeic acid with quinic acid, producing chlorogenic acid, reduces their ability to inhibit α-amylase and α-glucosidase activities. Thus, the inhibition of α-amylase and α-glucosidase activities by the phenolic acids could be part of the possible mechanism by which the phenolic acids exert their antidiabetic effects.

Exploring efficient extraction methods: Bioactive compounds and antioxidant properties from New Zealand damson plums

This study aimed to investigate the performance of accelerated solvent extraction (ASE) as a green approach for the recovery of polyphenols and pigments from wild nettle leaves (NL). ASE was operated at different temperatures (20, 50, 80 and 110 °C), static times (5 and 10 min) and cycle numbers (1–4) using ethanol (96%) as an extraction solvent. In order to compare the efficiency of ASE, ultrasound assisted extraction (UAE) at 80 °C for 30 min was performed as a referent. Polyphenol and pigment analyses were carried out by HPLC and antioxidant capacity was assessed by ORAC. Seven polyphenols from subclasses of hydroxycinnamic acids and flavonoids, along with chlorophylls a and b and their derivatives and six carotenoids and their derivatives were identified and quantified. Chlorogenic acid was the most abundant polyphenol and chlorophyll a represented the dominant pigment. ASE conditions at 110 °C/10 min/3 or 4 cycles proved to be the optimal for achieving the highest yields of analyzed compounds. In comparison with UAE, ASE showed better performance in terms of yields and antioxidants recovery, hence delivering extract with 60% higher antioxidant capacity. Finally, the potential of NL as a functional ingredient from natural sources can be successfully accessed by ASE.

Optimization of accelerated solvent extraction, ultrasound assisted and supercritical fluid extraction to obtain carnosol, carnosic acid and rosmarinic acid from rosemary

Bioprospecting Dodonaea viscosa Jacq.; a traditional medicinal plant for antioxidant, cytotoxic, antidiabetic and antimicrobial potential

Absorption of orally administered chlorogenic acid (5-caffeoylquinic acid) and caffeic acid in rats was studied to obtain plasma pharmacokinetic profiles of their metabolites. Rats were administered 700 micromol/kg body weight of chlorogenic or caffeic acid, and blood was collected from the tail for 6 h after administration. Ingested caffeic acid was absorbed from the alimentary tract and was present in the rat blood circulation in the form of various metabolites. On the other hand, only traces of metabolites, supposedly caffeic and ferulic acids conjugates, were detected in rat plasma for 6 h after chlorogenic acid administration. Chlorogenic acid and small amounts of caffeic acid were found in the small intestine for 6 h after chlorogenic acid administration. These results suggest that chlorogenic acid is not well absorbed from the digestive tract, unlike caffeic acid, and subject to almost no structural changes to the easily absorbed forms.

Chlorogenic acids (CGAs) are major polyphenols found in coffee that offer numerous health benefits. CGAs are compounds in which caffeic or ferulic acids are ester-bonded to quinic acids, with molecules such as caffeoylquinic acid, feruloylquinic acid, and dicaffeoylquinic acid being prominent examples. Due to their diverse structures, CGAs can be converted into multiple molecules during absorption, exerting various health effects through subtle differences in action. This chapter explores the health effects and mechanisms of CGAs, caffeic acid, and ferulic acid. In particular, it focuses on their impact on type 2 diabetes mellitus (T2DM), dyslipidemia, and hypertension associated with obesity, which form the basis of metabolic syndrome. Studies published in PubMed, ScienceDirect, and Web of Science on the health benefits of coffee, coffee-derived CGAs, quinic acid, and caffeic acid were analyzed. CGAs, quinic acids, and caffeic acids may potentially mitigate metabolic syndrome by preventing T2DM and various diseases, such as hypertension, through mechanisms including antioxidant activity.

Introduction: modulation of apoptosis is necessary in the basic physiological response to cancer. However, in some cancer scenarios, apoptosis is inhibited allowing the tumor proliferation. Searching for new therapeutic agents that promote apoptosis in cancer is relevant. Among these potential agents are caffeic acid and chlorogenic acid. Several studies have evaluated the activity of polyphenols as modulators in the apoptosis process. This study evaluated the affinity of caffeic and chlorogenic acid for some proteins related with apoptosis pathway using docking molecular strategies.Methods: the pro and anti-apoptotic proteins included in the analysis were catalase, heat shock protein 27 (HSP27), P27/Kip1/CDKN, Bcl-XL, cytochrome C, PON2, H02-HM0X2, Bax. The crystallographic structures were downloaded from Protein Data Bank and ligands from PubChem. Preparation of the ligands was done in Avogadro 1.2 and proteins in Chimera 1.15. Docking experiments were implemented in Autodock Vina.Results: chorogenic acid showed the best affinity with the proposed proteins. HSP27 presented a good affinity for the two ligands, with score affinity of -7.9 in caffeic acid and -9.0 in chlorogenic acid. In the same way, catalase presented a good affinity with -7.9 in score affinity in both ligands.Conclusions: the docking molecular analysis suggests potential pro-apoptotic functions for chlorogenic and caffeic acid considering their affinity with anti-apoptotic proteins.

Microbial metabolism of caffeic acid and its esters chlorogenic and caftaric acids by human faecal microbiota in vitro

The plant phenols chlorogenic and caffeic acids were tested for their affinity to alter hepatic and intestinal xenobiotic Phase I and Phase II enzyme activities in mice. Mice were fed isocaloric and isonitrogenous powdered diets containing 0 and 0.2% caffeic and chlorogenic acids, respectively. Animals pre-treated with benzo(a)pyrene (B(a)P) were sacrificed 18 h after an oral dose (50 mg/kg Bwt). B(a)P induced animals exhibited higher (p < 0.05) microsomal AHH, UDPGT, P-450 and cytosolic GST liver enzyme activities. The presence of these phenolics in the diet was shown to have little effect in modulating hepatic xenobiotic activating-detoxification enzymes. The dietary intake of caffeic and chlorogenic acids was particularly evident with intestinal xenobiotic AHH and GST enzyme activity. These data indicate that the presence of caffeic and chlorogenic acids in the diet may have an integral role in modulating the carcinogenic potential of reactive xenobiotics such as B(a)P.

We describe the antioxidant capability of scavenging the superoxide radical of several tea and yerba mate samples using rotating ring–disk electrochemistry (RRDE). We directly measured superoxide concentrations and detected their decrease upon the addition of an antioxidant to the electrochemical cell. We studied two varieties of yerba mate, two varieties of black tea from Bangladesh, a sample of Pu-erh tea from China, and two components, caffeic acid and chlorogenic acid. All of these plant infusions and components showed strong antioxidant activities, virtually annihilating the available superoxide concentration. Using density functional theory (DFT) calculations, we describe a mechanism of superoxide scavenging via caffeic and chlorogenic acids. Superoxide can initially interact at two sites in these acids: the H4 catechol hydrogen (a) or the acidic proton of the acid (b). For (a), caffeic acid needs an additional π–π superoxide radical, which transfers electron density to the ring and forms a HO2− anion. A second caffeic acid proton and HO2− anion forms H2O2. Chlorogenic acid acts differently, as the initial approach of superoxide to the catechol moiety (a) is enough to form the HO2− anion. After an additional acidic proton of chlorogenic acid is given to HO2−, three well-separated compounds arise: (1) a carboxylate moiety, (2) H2O2, and a (3) chlorogenic acid semiquinone. The latter can capture a second superoxide in a π–π manner, which remains trapped due to the aromatic ring, as for caffeic acid. With enough of both acids and superoxide radicals, the final products are equivalent: H2O2 plus a complex of the type [X-acid–η–O2], X = caffeic, chlorogenic. Chlorogenic acid (b) is described by the following reaction: 2 O2•− + 2 chlorogenic acid → 2 chlorogenic carboxylate + O2 + H2O2, and so, it acts as a non-enzymatic superoxide dismutase (SOD) mimic, as shown via the product formation of O2 plus H2O2, which is limited due to chlorogenic acid consumption. Caffeic acid (b) differs from chlorogenic acid, as there is no acidic proton capture via superoxide. In this case, approaching a second superoxide to the H4 polyphenol moiety forms a HO2− anion and, later, an H2O2 molecule upon the transfer of a second caffeic acid proton.

Fungal biotransformation of chlorogenic and caffeic acids by Fusarium graminearum: New insights in the contribution of phenolic acids to resistance to deoxynivalenol accumulation in cereals

The absorption and metabolism in the small intestine of chlorogenic acid (5-O-caffeoylquinic acid), the main phenolic acid in the human diet, and of caffeic acid were studied in rats in order to determine whether chlorogenic acid is directly absorbed or hydrolysed in the small intestine. Chlorogenic and caffeic acids were perfused into a segment of ileum plus jejunum during 45 min (50 microm, 0.75 ml/min) using an in situ intestinal perfusion rat model with cannulation of the biliary duct, and were quantified together with their metabolites in perfusion effluent, bile and plasma. The net absorption (influent flux minus effluent flux of phenolic acids and their metabolites) accounted for 19.5 % and 8 % of the perfused caffeic and chlorogenic acids, respectively. A minor fraction of the perfused caffeic acid was metabolized in the intestinal wall and secreted back into the gut lumen in the form of ferulic acid (0.5 % of the perfused flux). Part of the chlorogenic acid (1.2 % of the perfused flux) was recovered in the gut effluent as caffeic acid, showing the presence of trace esterase activity in the gut mucosa. No chlorogenic acid was detected in either plasma or bile, and only low amounts of phenolic acids (less than 0.4 %) were secreted in the bile. The present results show that chlorogenic acid is absorbed and hydrolysed in the small intestine. In contrast to numerous flavonoids, absorbed phenolic acids are poorly excreted in the bile or gut lumen. Their bioavailability therefore appears to be governed largely by their uptake into the gut mucosa.

It is not uncommon to treat plant-derived foods and feeds with alkali. Such exposure to high pH is being used to recover proteins from cereals and legumes, to induce the formation of fiber-forming meat analogue vegetable protein, for preparing peeled fruits and vegetables, and for destroying microorganisms. In addition to their profound effects on functional and nutritional properties in such foods, such treatments may also cause other side reactions, including the destruction of natural polyphenolic compounds. Because plants contain a large number of structurally different antioxidant, anticarcinogenic, and antimicrobial polyphenolic compounds, it is of interest to know whether such compounds are stable to heat and to high pH. In this model study, the stability of the following natural polyphenols to pH in the range 3-11 was studied with the aid of ultraviolet spectroscopy: caffeic acid, (-)-catechin, chlorogenic acid, ferulic acid, gallic acid, (-)-epigallocatechin, rutin, and the nonphenolic compound trans-cinnamic acid. This study demonstrates that caffeic, chlorogenic, and gallic acids are not stable to high pH and that the pH- and time-dependent spectral transformations are not reversible. By contrast, chlorogenic acid is stable to acid pH, to heat, and to storage when added to apple juice. (-)-Catechin, (-)-epigallocatechin, ferulic acid, rutin, and trans-cinnamic acid resisted major pH-induced degradation. The results are rationalized in terms of relative resonance stabilization of phenoxide ions and quinone oxidation intermediates. The possible significance of these findings to food chemistry and microbiology is discussed.