Proanthocyanidin characterization and bioactivity of extracts from different parts of Uncaria tomentosa L. (cat’s claw)

This article belongs to the Special Issue Dietary Antioxidants and Health Promotion.-- et al.Apart from alkaloids, bioactive properties of Uncaria tomentosa L. have been attributed to its phenolic constituents. Although there are some reports concerning low-molecular-weight polyphenols in U. tomentosa, its polymeric phenolic composition has been scarcely studied. In this study, phenolic-rich extracts from leaves, stems, bark and wood (n = 14) of Uncaria tomentosa plants from several regions of Costa Rica were obtained and analysed in respect to their proanthocyanidin profile determined by a quadrupole-time-of-flight analyser (ESI-QTOF MS). Main structural characteristics found for U. tomentosa proanthocyanidins were: (a) monomer composition, including pure procyanidins (only composed of (epi)catechin units) and propelargonidins (only composed of (epi)afzelechin units) as well as mixed proanthocyanidins; and (b) degree of polymerization, from 3 up to 11 units. In addition, U. tomentosa phenolic extracts were found to exhibit reasonable antioxidant capacity (ORAC (Oxygen Radical Absorbance Capacity) values between 1.5 and 18.8 mmol TE/g) and antimicrobial activity against potential respiratory pathogens (minimum IC of 133 µg/mL). There were also found to be particularly cytotoxic to gastric adenocarcinoma AGS and colon adenocarcinoma SW620 cell lines. The results state the particularities of U. tomentosa proanthocyanidins and suggest the potential value of these extracts with prospective use as functional ingredients.This project was partially funded by grant from the Spanish International Development Cooperation Agency (AECID) (Ref. A/023397/09 and A/030037/10) and a joint grant from the Costa Rica-USA Foundation (CRUSA) and the Spanish Scientific Research Council (CSIC) (Ref. CR0024). Authors also thank financial support from the Comunidad de Madrid (Spain) and European funding from FEDER program (projects AVANSECAL-CM S2013/ABI-3028 and ALIBIRD-CM S2013/ABI-2728) and from the University of Costa Rica. Special thanks are due to Eng. Juan Jose Cordero from Costa Rican National Production Council (CNP).Peer Reviewe

Comparative effects of A- and B-type proanthocyanidins in the prevention of urinary tract infection in mice

Resumen del póster presentado a la VI International Conference on Polyphenols and Health celebrada en Buenos Aires (Argentina) del 16 al 19 de octubre de 2013.Consumption of cranberry (Vaccinium macrocarpum) is widely recommended forprophylaxis against urinary tract infections (UTI) in women. Among cranberry components, A-type proanthocyanins would be implicated in these preventive effects against UTI. However, proanthocyanidins are poorly absorbed in the small intestine, but subjected to extensive biotransformation in the colon, although studies are almost restricted to B-type proanthocyanidins. Therefore, the hypothesis of this study is that urinary metabolome from of A-type and B-type proanthocyanidins-mainly derived from their colonic catabolism-differ,and only metabolites from the A-type procyanidins have protective effects against UTI. To test this hypothesis, JAXc3H/OuJ female mice previously fed with specific diet (control, 1% cranberry extract and 1% grape seed extract) for 2 weeks, were inoculated with the uropathogenic E. coli (ATCC 53503™) to provoke infection, and maintained 2 weeks more before being sacrificed. Urine samples were collected at different times and subjected to E.coli counting, leukocytary esterase and nitrites analyses, and mieloperoxidase task. Samples of kidney and bladder tissues were also collected for E. coli counting and histopathologic analysis. Additionally, the capacity of the urine samples to inhibit bacterial adherence was tested in the T24 bladder cell line (ATCC HTB4 ™).Peer reviewe

Evolución en botella de vinos tintos monovarietales y mezclas de Vitis vinifera L. Polifenoles y color

Tesis doctoral inédita leída en la Universidad Autónoma de Madrid, Facultad de Ciencias, Departamento de Química Física e Instituto de Fermentaciones Industriales (CSIC). Fecha de lectura 21-06-2004En esta memoria se presentan los cambios que ocurren en los compuestos fenólicos antociánios y no-antociánicos, y en el color de vinos tintos jóvenes y monovarietales de Vitis vinifera L. Tempranillo (variedad española por exigencia). Graciano (variedad española poco extendida pero altamente apreciada) y Cabernet Sauvignon (variedad francesa conocida y cultivada a nivel internacional durante el (envejecimiento en botella". Para ello, los vino (vendimia 2000) elaborados en la estación de Enología y Viticultura de Navarra -EVENA- (Olite, Navarra, España), se analizaron en diferentes fechas a lo largo de 26 meses de envejecimiento en botella determinándose el contenido fenólico total, la composición fenólica pormenorizada mediante HPLC/DAD y HPLC/ESI-MS, así como, las características cromáticas mediante el cálculo de índices colorimétricos y variables CIELAB

Evolución en botella de vinos tintos monovarietales y mezclas de Vitis Vinífera L. polifenoles y color

En esta memoria se presentan los cambios que ocurren en los compuestos fenólicos antociánicos y noantociánicos, y en el color de vinos tintos jóvenes monovarietales de Vitis vinifera L. Tempranillo (variedad española por excelencia), Graciano (variedad española poco extendida pero altamente apreciada), y Cabernet Sauvignon (variedad francesa conocida y cultivada a nivel internacional) durante el >envejecimiento en botella>. Para ello, los vinos (vendimia 2000), elaborados en la Estación de Enología y Viticultura de Navarra -EVENA- (Olite, Navarra, España), se analizaron en diferentes fechas a lo largo de 26 meses de envejecimiento en botella determinándose el contenido fenólico total y la composición fenólica pormenorizada mediante HPLC/DAD y HPLC/ESI-MS, así como, las características cromáticas mediante el cálculo de índices colorimétricos y variables CIELAB. Paralelamente, se realizó un estudio similar con mezclas de vinos, empleando el vino de Tempranillo como vino base, y los vinos de las variedades Graciano y Cabernet Sauvignon como modificadores en las proporciones de 90:10 y 75:25 (v/v), con la finalidad de comparar y valorar el efecto que tienen estas variedades sobre la composición fenólica y el color del vino de la variedad de Tempranillo durante el envejecimiento en botella.Peer Reviewe

Effect of cocoa powder in the prevention of cardiovascular disease: Biological, consumption and inflammatory biomarkers. A metabolomic approach

12 páginas, 2 figuras.-- et al.Numerous health benefits have been attributed to cocoa and its derived products in the last decade including antioxidant, anti-platelet and positive effects on lipid metabolism and vascular function. Inflammation plays a key role in the initiation and progression of atherosclerosis. However, cocoa feeding trials focused on inflammation are still rare and the results yielded are controversial. Health effects derived from cocoa consumption have been partly attributed to its polyphenol content, in particular of flavanols. Bioavailability is a key issue for cocoa polyphenols in order to be able to exert their biological activities. In the case of flavanols, bioavailability is strongly influenced by several factors, such as their degree of polymerization and the food matrix in which the polyphenols are delivered. Furthermore, gut has become an active site for the metabolism of procyanidins (oligomeric and polymeric flavanols). Estimation of polyphenol consumption or exposure is also a very challenging task in Food and Nutrition Science in order to correlate the intake of phytochemicals with in vivo health effects. In the area of nutrition, modern analytical techniques based on mass spectrometry are leading to considerable advances in targeted metabolite analysis and particularly in Metabolomics or global metabolite analysis. In this chapter we have summarized the most relevant results of our recent research on the bioavailability of cocoa polyphenols in humans and the effect of the matrix in which cocoa polyphenols are delivered considering both targeted analysis and a metabolomic approach. Furthermore, we have also summarized the effect of long-term consumption of cocoa powder in patients at high risk of cardiovascular disease (CVD) on the inflammatory biomarkers of atherosclerosis.This research was supported by national grants CICYT (AGL: 2004- 08378-C02-01/02, 2006-14228-C03-02/01 and 2009-13906-C02-01); CIBER 06/03 Fisiopatología de la Obesidad y la Nutrición is an initiative of the Instituto de Salud Carlos III, Spain; Centro Nacional de Investigaciones Cardiovasculares (CNIC-06) and Ingenio-CONSOLIDER program, Fun-cfood (CSD2007-063). M.U.-S. thanks the Sara Borrell postdoctoral program (CD09/00134), M.M. thanks the Ramon y Cajal program, R.Ll. thanks the Fondo de Investigación Sanitaria program (FIS, CD06/00161), and N.K. thanks the FPU fellowship program, all from the Ministry of Science and Innovation. M.R.-R. thanks the FI-DGR2010 fellowship program from the Generalitat de Catalunya. R.E. is recipient of a grant from FIS, Madrid, Spain.Peer reviewe

Evolution of polyphenols in red wines from Vitis vinifera L. during aging in the bottle

The evolution of anthocyanins and pyranoanthocyanins (as measured by high-performance liquid chromatography) in young red wines from Vitis vinifera L. cv Tempranillo, Graciano and Cabernet Sauvignon (vintage 2000) from Navarra (Spain) was studied during 26 months of aging in the bottle. For the anthocyanin pigments of grape origin, a progressive decrease in their concentration, corresponding to first-order kinetics, was observed during this period. Independently of the anthocyanin structure studied, grape anthocyanins in Tempranillo wine presented twofold slower kinetics than those in Graciano and Cabernet Sauvignon wines, which exhibited a very similar disappearance rate. Acylated anthocyanins presented a slightly higher disappearance rate than the nonacylated ones, indicating the possible hydrolysis of the former into the latter forms. However, no distinction was observed in the kinetics of the different anthocyanidin forms (delphinidins, petunidins, peonidins and malvidins). These results indicate that during aging under nonoxidative conditions (bottle), the chemical reactivity of grape anthocyanins in wine is influenced by the grape variety, a factor that imposes over the stability associated with the chemical structure of each anthocyanin form. In relation to the evolution of pyranoanthocyanins, anthocyanin–pyruvic acid adducts presented a similar or lower disappearance rate than their corresponding anthocyanin precursors during the first months of aging in the bottle, while anthocyanin–vinylphenol and anthocyanin–vinylflavanol adducts did not exhibit significant variations during the whole period studied.The authors also thank the Agencia Española de Cooperación International for a MUTIS predoctoral scholarship to M.M. and the Spanish Comisión Interministerial de Ciencia y Tecnología (projects AGL2000-1427-C02-02 and AGL2003-07394-C02-02) for funding.Peer reviewe

Updated knowledge about the presence of phenolic compounds in wine

Phenolic compounds are partly responsible for the color, astringency, and bitterness of wine, as well as for numerous physiological properties associated with wine consumption. Mass spectrometry has allowed for great progress in the identification and characterization of wine polyphenols. The aim of the present article is to summarize the numerous advances recently achieved in this field. The main type of phenolic compounds found in wine, including hydroxybenzoic and hydroxycinnamic acids, stilbenes, flavones, flavonols, flavanonols, flavanols, and anthocyanins, are firstly described. Chemical reactions and mechanisms involving phenolic compounds during winemaking are also extensively discussed, including enzymatic and chemical oxidation reactions, direct and acetaldehyde-mediated anthocyanin-tannin condensation reactions, acetaldehyde-mediated and glyoxylic acid-mediated tannin-tannin condensation reactions and, C-4/C-5 anthocyanin cycloaddition reactions with 4-vinylphenols, vinylflavanols and pyruvic acid, among others, leading to the formation of pyranoanthocyanins. Useful mass spectral data of well-known and novel phenolic compounds recently identified in wine, and details related to their fragmentation pathway according to different ionization techniques, are given.The authors are grateful to the Agencia Espanola de Cooperacion International (AECI) for a MUTIS predoctoral scholarship to M.M. and to the Spanish Comision Interministerial de Ciencia y Tecnologia (CICYT) (Projects AGL2000-1427-C02-02 and AGL2003-07394-C02-02/ALI) for funding.Peer reviewe

II. Non-anthocyanin phenolic compounds

The evolution of non-anthocyanin phenolic compounds (as measured by high-performance liquid chromatography) in young red wines from Vitis vinifera L. cv Tempranillo, Graciano and Cabernet Sauvignon (vintage 2000) from Navarra (Spain) was studied during 26 months of aging in the bottle. Hydroxybenzoic acids and derivatives (gallic, protocatechuic, vanillic and syringic acids, and methyl and ethyl gallates), hydroxycinnamic acids and derivatives (trans-caftaric, cutaric, caffeic and p-coumaric acids, and hexose esters of trans-p-coumaric acid), stilbenes (trans- and cis-resveratrol-3-O-glucosides, and trans- and cis-resveratrol), phenolic alcohols and other related compounds (tyrosol and tryptophol), flavanols [procyanidins B1 and B2, (+)-catechin and (−)-epicatechin] and flavonols (myricetin-3-O-glucoside, quercetin-3-O-galactoside and quercetin-3-O-glucuronide, kaempherol-3-O-glucoside, myricetin and quercetin) presented different evolution patterns during aging, in some cases also being different depending on the grape variety studied. The changes that occurred during aging in the bottle were the decrease of the concentration of trans-caftaric and cutaric acids accompanied by an increase of trans-caffeic acid and, especially of trans-p-coumaric acid. The greater increase of trans-p-coumaric acid was also associated with the disappearance of p-coumaroyl-acylated anthocyanins that occurs during aging in the bottle. Flavanols registered a major decrease, with the disappearance rate being greater for the dimeric procyanidins than for the monomeric flavanols, and the order of the disappearance rate by variety was as follows: Tempranillo<Graciano≅Cabernet Sauvignon. The low disappearance rate of flavanols in wines from Tempranillo was attributed to their low reactivity with anthocyanins, which in turn could be associated with the particular anthocyanin-to-flavanol ratio and with the high pH value of this variety.The authors thank the Agencia Española de Cooperación International for a MUTIS predoctoral scholarship to M.M. and the Spanish Comisión Interministerial de Ciencia y Tecnología (projects AGL2000-1427-C02-02 and AGL2003-07394-C02-02) for funding.Peer reviewe

Effect of the modifier (Graciano vs. Cabernet Sauvignon) on blends of Tempranillo wine during ageing in the bottle. I. Anthocyanins, pyranoanthocyanins and non-anthocyanin phenolics

The effect of Graciano (GRA) (Spanish valuable variety of limited production) vs. Cabernet Sauvignon (CS) (world wide known French variety) wines on the anthocyanin, pyranoanthocyanin and non-anthocyanin phenolic composition of wines from Tempranillo (TEM-base wine) (largely cultivated Spanish variety) was studied in wine blends prepared with 25% and 10% (v/v) of each modifier after 4, 6, 9, 16.5 and 23 months of ageing in the bottle. Blending mainly resulted in a higher concentration of peonidin anthocyanins for the TEM–GRA blends, of acetyl-glucoside anthocyanins and anthocyanin–pyruvic acid adducts for the TEM–CS blends, and of flavanols for the blends with both GRA and CS varieties, giving rise to wines with a more balanced anthocyanin/flavanol ratio. Blending also enhanced the changes expected to occur in the phenolic compounds during ageing in the bottle. Particularly, anthocyanins and flavanols in the blends disappeared faster than in the base wine, and this was more pronounced for the 75:25 than for the 90:10 blends. These effects were similar for both modifier wines, independent of the specific changes produced in the anthocyanin profile of the base wine, but coincided with the similar optimization of the anthocyanin/flavanol ratio provided by both Graciano and Cabernet Sauvignon wines.The authors also thank the Agencia Española de Cooperación International (AECI) for a MUTIS predoctoral scholarship to M.M. and the Spanish Comisión Interministerial de Ciencia y Tecnología (CICYT) (Project ALI2003-07394-C02-02) for funding.Peer reviewe

Evolution of the phenolic content of red wines from Vitis vinifera L. during ageing in bottle

The evolution of the phenolic content, as measured by spectrophotometric methodologies [total polyphenols (TP), low-polymerized polyphenols (LPP), total anthocyanins (TA), catechins (CAT), proanthocyanidins (PRO) and o-diphenols (OD)], was studied in young red wines from Vitis vinifera L. cv Tempranillo, Graciano and Cabernet Sauvignon during 26 months of ageing in bottle. Although the wines showed differences in their initial phenolic profiles, the evolution trend of the different families of phenolic compounds was similar in the wines from the three grape varieties. TA markedly decreased during ageing in bottle (43% for Tempranillo, 65% for Graciano and 66% for Cabernet Sauvignon), following a first-order kinetic. Calculation of the kinetic parameters revealed that the disappearance rate of TA was 2-fold lower for Tempranillo wine than for Graciano and Cabernet Sauvignon wines, which exhibited similar kinetics. This decrease in TA (due to the disappearance of monomeric anthocyanins), together with a increase registered in CAT and PRO (due to the cleavage of proanthocyanidins and their structural tranformations), was consistent with a decrease in LPP, suggesting the occurrence of condensation reactions during ageing in bottle. The evolution trends observed for TP and OD during ageing in bottle were the results of changes in the different groups of phenolic compounds involved in both determinations. Global phenolic determinations, usually performed in wineries, provided useful information in relation to the evolution of wine polyphenols during ageing in bottle.The authors thank the Agencia Española de Cooperación International (AECI) for a MUTIS predoctoral scholarship to M.M. and the Spanish Comisión Interministerial de Ciencia y Tecnología (CICYT) (Project AGL2003-07394-C02-02) for funding.Peer reviewe