Vescalagin

Variation in the Phenolic Composition of Cork Stoppers from Different Geographical Origins.[Pubmed:33274939]

J Agric Food Chem. 2020 Dec 4.

Cork stopper granulates from five geographical origins from Portugal and six from Spain were analyzed regarding polyphenol composition by HPLC-DAD/ESI-MS and geographical discrimination studied by near-infrared spectroscopy (NIRS). The phenolic composition of the eleven origins ranged from 30 to 52 mg/g cork granulates, with vescavaloninic acid, castalagin, sanguisorbic acid dilactone, Vescalagin, castavaloninic acid, dehydrated tergallic-C-Glc, and ellagic acid being the major compounds. NIRS revealed to be a powerful tool to discriminate origins and predict the concentration of polyphenols. However, polyphenols do not fully explain the discrimination of geographical origins. Variability in the polyphenol composition of cork stoppers is not significantly influenced by geographical location but probably may be more related to the plant genetics, tree age, and phytosanitary and edaphoclimatic conditions.

Generation Times of E. coli Prolong with Increasing Tannin Concentration while the Lag Phase Extends Exponentially.[Pubmed:33271746]

Plants (Basel). 2020 Dec 1;9(12). pii: plants9121680.

The current study examines the effect of tannins and tannin extracts on the lag phase duration, growth rate, and generation time of Escherichia coli. Effects of castalagin, Vescalagin, gallic acid, Colistizer, tannic acid as well as chestnut, mimosa, and quebracho extracts were determined on E. coli's growth phases using the broth microdilution method and obtained by turbidimetric measurements. E. coli responds to the stress caused by the investigated antimicrobial agents with reduced growth rates, longer generation times, and extended lag phases. Prolongation of the lag phase was relatively small at low tannin concentrations, while it became more pronounced at concentrations above half the MIC. Moreover, for the first time, it was observed that lag time extensions follow a strict exponential relationship with increasing tannin concentrations. This feature is very likely a direct consequence of the tannin complexation of certain essential ions from the growth medium, making them unavailable to E. coli for its growth.

Lythrum salicaria Ellagitannins Stimulate IPEC-J2 Cells Monolayer Formation and Inhibit Enteropathogenic Escherichia coli Growth and Adhesion.[Pubmed:33270444]

J Nat Prod. 2020 Dec 3.

Lythrum salicaria herb (LSH) was applied in diarrhea therapy since ancient times. Despite empirically referenced therapeutic effects, the bioactivity mechanisms and chemical constituents responsible for pharmacological activity remain not fully resolved. Taking into consideration the historical use of LSH in treatment of diarrhea in humans and farm animals, the aim of the study was to examine in vitro the influence of LSH and its C-glycosylic ellagitannins on processes associated with maintaining intestinal epithelium integrity and enteropathogenic Escherichia coli (EPEC) growth and adhesion. LSH was not only inhibiting EPEC growth in a concentration dependent manner but also its adhesion to IPEC-J2 intestinal epithelial cell monolayers. Inhibitory activity toward EPEC growth was additionally confirmed ex vivo in distal colon samples of postweaning piglets. LSH and its dominating C-glycosylic ellagitannins, castalagin (1), Vescalagin (2), and salicarinins A (3) and B (4) were stimulating IPEC-J2 monolayer formation by enhancing claudin 4 production. Parallelly tested gut microbiota metabolites of LSH ellagitannins, urolithin C (5), urolithin A (6), and its glucuronides (7) were inactive. The activities of LSH and the isolated ellagitannins support its purported antidiarrheal properties and indicate potential mechanisms responsible for its beneficial influence on the intestinal epithelium.

New C-Glycosidic Ellagitannins Formed upon Oak Wood Toasting; Identification and Sensory Evaluation.[Pubmed:33081146]

Foods. 2020 Oct 16;9(10). pii: foods9101477.

In the courses of studies on ellagitannin changes during oak wood toasting, two C-glycosidic ellagitannins were isolated from the french oak wood for the first time. These two compounds exhibited [M-H](-) ion peak at m/z 1055.0631 (compound A) and at m/z 1011.0756 (compound B). A compound is named Castacrenin E and is produced by Castacrenin D oxidation. Castacrenin D is a Vescalagin with an additional aromating ring to the C-1 through a C-C bond. These compounds are not only found under laboratory conditions but also in commercial oak wood representing different toasting methods and sizes. Their levels are conditioned by oak wood dimensions and toasting degree. The wood pieces with the smallest size present almost two times more compounds A and B. Moreover, the compound B is the only compound to be present in medium toasting temperatures of the smallest wood pieces. Both of them can influence either astringency sensation or bitterness taste.

Polyphenols of jabuticaba [Myrciaria jaboticaba (Vell.) O.Berg] seeds incorporated in a yogurt model exert antioxidant activity and modulate gut microbiota of 1,2-dimethylhydrazine-induced colon cancer in rats.[Pubmed:32717686]

Food Chem. 2021 Jan 1;334:127565.

The chemical composition, antioxidant activity (AA), cytotoxic activity, antihemolytic effects, and enzyme inhibition (EI) of lyophilized jabuticaba (Myrciaria jaboticaba) seed extract (LJE) was studied. The main compounds found were castalagin, Vescalagin, procyanidin A2, and ellagic acid. LJE was more toxic to cancer cells than to normal cells, meaning relative toxicological safety. This cytotoxic effect can be attributed to the pro-oxidant effect observed in the reactive oxygen species (ROS) generation assay. LJE inhibited alpha-amylase, alpha-glucosidase, and ACE-I activities and protected human erythrocytes from hemolysis. LJE was incorporated into yogurts at different concentrations and the total phenolic content, AA, and EI increased in a dose-dependent manner. LJE-containing yogurt presented 86% sensory acceptance. The yogurt was administered to Wistar rats bearing cancer and it modulated the gut bacterial microbiota, having a prebiotic effect. LJE is a potential functional ingredient for food companies looking for TPC, AA, and prebiotic effect in vivo.

Foliar traits of sessile oak (Quercus petraea Liebl) seedlings are largely determined by site properties rather than seed origin.[Pubmed:32705139]

Tree Physiol. 2020 Dec 5;40(12):1648-1667.

Due to climate change, sessile oak (Quercus petraea) seedlings experience an increasing risk of drought during regeneration of forest stands by management practices. The present study was aimed at elucidating the potential of sessile oak seedlings originating from sites with different aridity and nitrogen (N) supply to acclimate to contrasting water availability. For this purpose, a free-air cross-exchange experiment was conducted between a dry and a humid forest stand with high and low soil N contents, respectively, during two consecutive years differing in aridity before harvest. Almost all structural and physiological foliar traits analyzed did not differ consistently between seed origins during both years, when cultivated at the same site. As an exception, the arid provenance upregulated foliar ascorbate contents under drought, whereas the humid provenance accumulated the phenolic antioxidants Vescalagin and castalagin (VC) under favorable weather conditions and consumed VC upon drought. Apparently, differences in long-term aridity at the forest sites resulted in only few genetically fixed differences in foliar traits between the provenances. However, structural and physiological traits strongly responded to soil N contents and weather conditions before harvest. Foliar N contents and their partitioning were mostly determined by the differences in soil N availability at the sites, but still were modulated by weather conditions before harvest. In the first year, differences in aridity before harvest resulted in differences between most foliar traits. In the second year, when weather conditions at both sites were considerably similar and more arid compared to the first year, differences in foliar traits were almost negligible. This pattern was observed irrespective of seed origin. These results support the view that leaves of sessile oak seedlings generally possess a high plasticity to cope with extreme differences in aridity by immediate acclimation responses that are even better developed in plants of arid origin.

Response surface optimization of phenolic compounds extraction from camu-camu (Myrciaria dubia) seed coat based on chemical properties and bioactivity.[Pubmed:32645216]

J Food Sci. 2020 Aug;85(8):2358-2367.

Food companies should comply with the requirements of a zero-waste concept to adapt to the circular economy requirements. In fruit companies, usually seeds are discarded without proper utilization and extraction of the bioactive compounds. Fruit seeds are sources of chemical compounds that can be extracted, studied, and applied in high value-added products. Thus, in this work the experimental conditions for the water extraction of phenolic compounds from camu-camu (Myrciaria dubia) seed coat were optimized using a central composite design and the desirability function. Total phenolic content (TPC), and condensed tannins (CT), DPPH radical scavenging activity, ferric reducing antioxidant capacity (FRAP), Folin-Ciocalteu reducing capacity (FCRC), and Cu(2+) chelating ability were assessed. Seed coat extracted for 51.1 min using a 1:34.1 solid:liquid ratio was the optimal condition to extract 6,242 mg gallic acid equivalent (GAE)/100 g of TPC and 695 mg catechin equivalent (CE)/100 g of CT. The optimized extract displayed free-radical scavenging activity, reducing properties and ability to chelate Cu(2+) , and inhibited the growth of Listeria monocytogenes, Pseudomonas aeruginosa, Salmonella Typhimurium, Salmonella Enteritidis, Bacillus cereus, and Staphylococcus aureus. Additionally, the lyophilized water extract inhibited the in vitro activity of alpha-amylase, alpha-glucosidase, and angiotensin converting enzyme and showed cytotoxic effects towards Caco-2, A549, and HepG2 cancer cells, but no cytotoxicity towards IMR90 cells. Vescalagin, castalagin, and 3,4-dihydroxybenzoic acid were the major phenolic compounds identified in the optimized extract. In conclusion, the optimized camu-camu seed coat water extract is a rich source of phenolic compounds with antioxidant, antidiabetic, antihypertensive, and antiproliferative effects. PRACTICAL APPLICATION: Camu-camu fruit pulp and seeds have been studied for their phenolic composition and bioactivity. However, seeds are usually discarded and represent an environmental problem in South American countries. We presented a methodological overview on the extraction optimization of the phenolic compounds from camu-camu seed coat and studied the bioactivity of the optimized extract using chemical, enzymatic, and cell-based experiments. Results can be used by camu-camu processors to obtain a phenolic-rich extract for industrial applications, without any further processing.

The Effect of Growth Medium Strength on Minimum Inhibitory Concentrations of Tannins and Tannin Extracts against E. coli.[Pubmed:32604845]

Molecules. 2020 Jun 26;25(12). pii: molecules25122947.

In this study the effect of growth medium strength on the minimum inhibitory concentration (MIC) of different tannins and tannin extracts against Escherichia coli was systematically investigated for the first time. Three pure compounds (Vescalagin, castalagin and gallic acid) and five extracts (chestnut, quebracho, mimosa, Colistizer and tannic acid) were studied. Broth microdilution was assayed and bacteria were grown using different growth medium strengths varying from half to double the concentration recommended by the producer. MICs were determined using the iodonitrotetrazolium chloride (INT) dye or turbidity measurements. It was observed that MIC values depend on the growth medium strength. With an increase in the growth medium concentration MIC values rose roughly linearly for all samples, while their relative order remained unchanged, indicating that a direct interaction of tannins with growth medium nutrients represents the likely source of their antimicrobial activity. Understanding the effect of growth medium strength can finally yield a plausible explanation for the observed variation in MIC values reported in the scientific literature as well as provide help in planning proper applications of tannins in the livestock production.

Subcritical Water Extraction of Chestnut Bark and Optimization of Process Parameters.[Pubmed:32560152]

Molecules. 2020 Jun 16;25(12). pii: molecules25122774.

The aim of the work was the optimization of the subcritical water extraction process of chestnut bark using Box-Behnken response surface methodology. The influence of process parameters, such as temperature, extraction time and solvent-solid ratio, on extraction yield, yield of the main compounds, total phenol content, total tannin content and antioxidant activity has been investigated. The identified compounds were ellagic and gallic acids, ellagitannins (Vescalagin, castalagin, 1-o-galloyl castalagin, vescalin and castalin), sugars (maltose, glucose, fructose and arabinose) and sugar derivatives (5-HMF, furfural and levulinic acid). Finally, the optimal process conditions for obtaining the bark extract highly rich in ellagic acid and with satisfactory levels of total phenols and total tannins have been determined.

Response surface optimization of phenolic compounds from jabuticaba (Myrciaria cauliflora [Mart.] O.Berg) seeds: Antioxidant, antimicrobial, antihyperglycemic, antihypertensive and cytotoxic assessments.[Pubmed:32450285]

Food Chem Toxicol. 2020 Aug;142:111439.

The aim of this study was to evaluate the effects of different solvents and maximize the extraction of bioactive compounds from jabuticaba (Myrciaria cauliflora) seeds. In general, the solvent system composed of water and propanone (52:48 v/v) modified the extract polarity and increased extraction yield of bioactive compounds. The optimized extract presented antioxidant capacity measured by different chemical and biological assays. The optimized extract exerted antiproliferative and cytotoxic effects against A549 and HCT8 cells, antimicrobial and antihemolytic effects, inhibited alpha-amylase/alpha-glucosidase activities and presented in vitro antihypertensive effect. Nonetheless, the optimized extract showed no cytotoxicity in a human cell model (IMR90). Vescalagin, castalagin and ellagic acid were the major phenolic compounds in the optimized extract. Our results show that jabuticaba seed may be a potential ingredient for the development of potentially functional foods.

Vescalagin and castalagin reduce the toxicity of amyloid-beta42 oligomers through the remodelling of its secondary structure.[Pubmed:32068230]

Chem Commun (Camb). 2020 Mar 12;56(21):3187-3190.

The isomers Vescalagin and castalagin protect SH-SY5Y cells from Abeta42-mediated death. This is achieved better by Vescalagin due to the spatial organization of its OH group at the C1 position of the glycosidic chain, improving its capacity to remodel the secondary structure of toxic Abeta42 oligomers.

Oxidation of the Oak Ellagitannin, Vescalagin.[Pubmed:32004001]

J Nat Prod. 2020 Feb 28;83(2):413-421.

Vescalagin (1) is a major ellagitannin from young spring leaves of Quercus glauca; however, the amount of 1 decreases as the leaves mature with a concomitant rise in the levels of catechin (3) and procyanidins. In this report, the chemical mechanism responsible for the degradation of 1 was investigated. In vitro model experiments indicated that initially a polyphenol oxidase oxidizes the catechin B-ring, and the resulting catechin o-quinone oxidizes one of the pyrogallol rings of 1 to give a cyclopenten-1,2-dione-type product 4. The presence of 4 in young oak leaves was confirmed by the detection of 4 and its quinoxaline derivative 4a. Furthermore, it was demonstrated that the cyclopenten-1,2-dione moiety of 4 nonenzymatically reacted with the catechin A-ring to yield the conjugate 5. Similar conjugations probably occur with procyanidins; thus, these reactions are possibly responsible for the decrease in the levels of 1 in leaves. The same cyclopenten-1,2-dione product 4 was also generated by treatment of 1 with a wood-rotting mushroom, Lentinula edodes, and further oxidative cleavage of a second pyrogallol ring of 4 was also observed. The results indicate the presence of a common degradation mechanism of 1 by plants and microbes.

Camu-camu seed (Myrciaria dubia) - From side stream to anantioxidant, antihyperglycemic, antiproliferative, antimicrobial, antihemolytic, anti-inflammatory, and antihypertensive ingredient.[Pubmed:31816536]

Food Chem. 2020 Apr 25;310:125909.

Camu-camu (Myrciaria dubia) seeds are discarded without recovering the bioactive compounds. The main aim of the present work was to optimise the solvent mixture to extract higher total phenolic content and antioxidant capacity of camu-camu seeds. The optimised solvent system increased the extraction of phenolic compounds, in which Vescalagin and castalagin were the main compounds. The optimised extract displayed antioxidant capacity measured by different chemical and biological assays, exerted antiproliferative and cytotoxic effects against A549 and HCT8 cancer cells, antimicrobial effects, protected human erythrocytes against hemolysis, inhibited alpha-amylase and alpha-glucosidase enzymes and presented in vitro antihypertensive effect. Additionally, the optimized extract inhibited human LDL copper-induced oxidation in vitro and reduced the TNF-alpha release and NF-kappaB activation in macrophages cell culture. Thus, the use of camu-camu seed showed to be a sustainable way to recover bioactive compounds with in vitro functional properties.