Procyanidins: Characterisation, antioxidant properties and health benefits
Abstract
Procyanidins are phenolic compounds from plants and they are abundant in our diet. Research studies on procyanidins have shown that they have many health benefits, especially as preventive agents for cancer, cardiovascular diseases and diabetes. High concentrations of procyanidins can be found in plants and foods such as red wine, grapes, grape seeds, cocoa, berries and apples. The first chapter of this book reviews the occurrence and the structure of these compounds. Since the extraction method is considered a critical step in procyanidin analysis, the second chapter describes the various methods used in literature so far with reference to the most important factors influencing the extraction. Furthermore, common separation and detection methods like high performance liquid chromatography and mass spectrometry are presented in order to give the complex image of the existing methods described so far. These principles of procyanidin fingerprinting are reflected further in studying the seed shells of the Japanese horse chestnut (Aesculus turbinata BLUME), discarded as waste materials after the preparation of edible seeds. The highly polymeric proanthocyanidins from the Japanese horse chestnut were tested for their health benefits, and this is presented in Chapter Three. As the interest in antioxidant compounds increases, the interest in studying their bioavailability has increased as well. In the context of controversy surrounding the studies on procyandins’ absorption and metabolization, the next chapter tries to present different points of view related to this matter. Several applications of procyanidins in food systems are reviewed in Chapter Five, including: Co-encapsulation of green tea catechins on probiotic bacteria viability during simulated gastrointestinal digestion, stability of polyphenolic compounds on alginate, and chitosan microcapsules and procyanidin effectiveness after incorporation into food edible films. The final part of this book investigates the procyanidin structure-activity relationship and mechanisms of cardiovascular diseases because the intake of procyanidins has been associated with reduced cardiovascular disease risk by epidemiologic studies. The expertise of the authors contributing to this book is useful for graduates studying food science and technology, nutrition, pharmacy and health, and for researchers, scientists, policymakers and professionals from food, pharmacy, nutrition and biotechnology industries working on procyanidins’ characterization, antioxidant properties and health benefits.
... The antitumor and antiinflammatory effects of procyanidin B2 are stronger than those of other procyanidins, that is procyanidin B1, B4, and B5, at similar concentrations. Moreover, procyanidin B2 is beneficial for diabetes complications and presents a protective effect against diabetic nephropathy by ameliorating podocyte injuries and preventing mesangial cell apoptosis [18,19]. Plant biomass, including apple peel, liquefies upon treating it with subcritical water. ...
... First, plant biomass components dissolve in water, and then the main liquefaction product is converted into a light product [3][4][5][6][7][8]. Several methods have been used to extract bioactive substances from plant biomass, and the advantages and disadvantages of each method have been described in the literature [18,19,22]. For example, the Soxhlet extraction method is simple; however, it requires long extraction times, and organic solvents are typically used as extraction media. ...
Subcritical water, which is an effective solvent for polar and nonpolar substances, has been used to extract numerous natural ingredients. In this study, subcritical water was used to extract bioactive substances from apple peel in a batch process in the temperature range of 100-175 °C for 5-60 min. The Fourier-transform infrared spectroscopy results revealed that phenolic compounds were released from apple peel in the aforementioned temperature range. The ultraviolet-visible spectra of the liquid products at 280 nm revealed the high content of phenolic compounds in the extracts. The high-performance liquid chromatography results demonstrated that the yield of procyanidin B2 was approximately 2.28 mg/g of dried apple peel when extraction was performed at 150 °C for 15 min.
The main dietary sources of polyphenols are reviewed, and the daily intake is calculated for a given diet containing some common fruits, vegetables and beverages. Phenolic acids account for about one third of the total intake and flavonoids account for the remaining two thirds. The most abundant flavonoids in the diet are flavanols (catechins plus proanthocyanidins), anthocyanins and their oxidation products. The main polyphenol dietary sources are fruit and beverages (fruit juice, wine, tea, coffee, chocolate and beer) and, to a lesser extent vegetables, dry legumes and cereals. The total intake is ∼1 g/d. Large uncertainties remain due to the lack of comprehensive data on the content of some of the main polyphenol classes in food. Bioavailability studies in humans are discussed. The maximum concentration in plasma rarely exceeds 1 μM after the consumption of 10–100 mg of a single phenolic compound. However, the total plasma phenol concentration is probably higher due to the presence of metabolites formed in the body's tissues or by the colonic microflora. These metabolites are still largely unknown and not accounted for. Both chemical and biochemical factors that affect the absorption and metabolism of polyphenols are reviewed, with particular emphasis on flavonoid glycosides. A better understanding of these factors is essential to explain the large variations in bioavailability observed among polyphenols and among individuals.
Anthocyanins are natural pigments derived from the phenylpropanoid pathway. Most tomatoes produce little anthocyanins, but the transgenic purple tomato biosynthesizes a high level of anthocyanins due to expression of two transcription factors (Del and Ros1). This study was to identify and quantify anthocyanins in this transgenic tomato line. Seven anthocyanins, including two new anthocyanins [malvidin-3-(p-coumaroyl)-rutinoside-5-glucoside and malvidin-3-(feruloyl)-rutinoside-5-glucoside], were identified by LC-MS/MS. Petunidin 3-(trans-coumaroyl)-rutinoside-5-glucoside and delphinidin 3-(trans-coumaroyl)-rutinoside-5-glucoside were the most abundant anthocyanins, making up 86% of the total anthocyanins. Compared to undetectable anthocyanins in the wild type, the contents of anthocyanins in the whole fruit, peel, and flesh of the Del/Ros1-transgenic tomato were 5.2 ± 0.5, 5.1 ± 0.5, and 5.8 ± 0.3 g/kg dry matter, respectively. Anthocyanins were undetectable in the seeds of both wide-type and transgenic tomato lines. Such novel and high levels of anthocyanins obtained in this transgenic tomato may provide unique functional products with potential health benefits.
Colorectal cancer is one of the main causes of cancer-related mortality in the developed world. Carcinogenesis is a multistage process conventionally defined by the initiation, promotion and progression stages. Natural polyphenolic compounds can act as highly effective antioxidant and chemo-preventive agents able to interfere at the three stages of cancer. Cocoa has been demonstrated to counteract oxidative stress and to have a potential capacity to interact with multiple carcinogenic pathways involved in inflammation, proliferation and apoptosis of initiated and malignant cells. Therefore, restriction of oxidative stress and/or prevention or delayed progression of cancer stages by cocoa antioxidant compounds has gained interest as an effective approach in colorectal cancer prevention. In this review, we look over different in vitro and in vivo studies that have identified potential targets and mechanisms whereby cocoa and their flavonoids could interfere with colonic cancer. In addition, evidence from human studies is also illustrated.
For some classes of dietary polyphenols, there are now sufficient intervention studies to indicate the type and magnitude of effects among humans in vivo, on the basis of short-term changes in biomarkers. Isoflavones (genistein and daidzein, found in soy) have significant effects on bone health among postmenopausal women, together with some weak hormonal effects. Monomeric catechins (found at especially high concentrations in tea) have effects on plasma antioxidant biomarkers and energy metabolism. Procyanidins (oligomeric catechins found at high concentrations in red wine, grapes, cocoa, cranberries, apples, and some supplements such as Pycnogenol) have pronounced effects on the vascular system, including but not limited to plasma antioxidant activity. Quercetin (the main representative of the flavonol class, found at high concentrations in onions, apples, red wine, broccoli, tea, and Ginkgo biloba) influences some carcinogenesis markers and has small effects on plasma antioxidant biomarkers in vivo, although some studies failed to find this effect. Compared with the effects of polyphenols in vitro, the effects in vivo, although significant, are more limited. The reasons for this are 1) lack of validated in vivo biomarkers, especially in the area of carcinogenesis; 2) lack of long-term studies; and 3) lack of understanding or consideration of bioavailability in the in vitro studies, which are subsequently used for the design of in vivo experiments. It is time to rethink the design of in vitro and in vivo studies, so that these issues are carefully considered. The length of human intervention studies should be increased, to more closely reflect the long-term dietary consumption of polyphenols.
The plots the amount of compound extracted versus solvent flow rates and versus solvent volume can determine the relative importance of these steps. For example, if the rate of extraction is controlled by intra-particle diffusion or kinetic desorption, the increase in bulk fluid flow rate would have little effect on extraction rate. On the other hand, if the extraction is controlled by external film transfer diffusion, extraction rates increase with solvent flow rate. In the case where the extraction rate is controlled by thermodynamic partitioning, doubling the bulk fluid flow rate would double the extraction rate, while the curves of extraction efficiency versus the volume of water passed for all flow rates would overlap. In one of our previous work, four proposed models have been applied to describe the extraction mechanisms obtained with SWE of Z. multiflora essential oil. These were included (1) partitioning coefficient model, (2) one-site (3) two-site desorption models and (4) thermodynamic partition with external mass transfer model [11]. In other studying unsteady state mass balance of the solute in solid and subcritical water phases (two-phase model) was investigated [12]. Also Computational Fluid Dynamics (CFD) modeling of extraction was considered [13].
It was tried to give overall view about subcritical water extraction. Effective parameters, mechanism and modeling of extraction were surveyed. Overall by considering mean average errors of models, a mathematical model base on the combination of partition coefficient (KD) and external mass transfer gave a good description of subcritical water extraction of Z. multiflora, while the kinetic model reasonably described the extraction behavior at lower flow rates [11].
The increasing incidence of degenerative diseases has attracted the interest in the obtaining of bioactive compounds. Since seeds and skins from grapes are important sources of polyphenols which have been associated with cancer incidence decreasing, then, one of the pisco (alcoholic beverage made of grape) manufacturing byproduct such as lees, could be a potential source of polyphenols. Supercritical fluid extraction is an environmentally friendly technique that has been applied for obtaining polyphenols. Carbon dioxide is used as unique or main extraction solvent instead of organic solvents, most of them toxics and responsible for reducing the application fields of the extracts. For that reason, among others, supercritical fluid extraction is preferred over conventional techniques for obtaining bioactive compounds. The aim of this work was to study the supercritical fluid extraction of polyphenols from lees of pisco-making. Supercritical carbon dioxide with 10 % of ethanol (w/w) was used as extraction solvent. Overall extraction curves were determined at 20 and 35 MPa; and the experimental data were used to estimate the kinetic parameters. Conventional techniques using ethanol as extraction solvent were performed for comparative purposes. The extracts were analyzed by thin-layer and high-performance liquid chromatography.
Lower global yield was obtained by supercritical fluid extraction than conventional techniques. From the kinetic parameters, the mass transfer rate and the amount of the extract dissolved in supercritical phase were higher at 20 than 35 MPa. Phenolic acids (gallic, protocatechuic, vanillic, syringic, ferulic derivatives and p-coumaric derivatives) and flavonoids (quercetin and its derivatives) were identified in the extracts obtained by all extraction techniques. Polyphenols were rapidly extracted with supercritical fluid and more concentrated extracts were obtained at 20 MPa. However, for longer extraction times, the highest values of extracted polyphenols were obtained by conventional techniques.
Lees from pisco-making are a promising source for recovery polyphenols. Low global yields were obtained when elevated pressures were used. Although supercritical fluid extraction at 20 MPa was the most efficient technique on the extraction of polyphenols from lees of pisco-making due to highly concentrated polyphenols, extracts were rapidly obtained.
Graphical Abstract:
Supercritical fluid extraction of polyphenols from lees
The experiment assessed the fatty acids (FA) composition of Longissimus dorsi (LD) muscle and plasma polyphenols spectrumin finishing hybrid Topigs fed diets containing dried grape pomace (DGP). The trial was conducted on 24 hybrids Topigs, 75.54±5.55 kg, randomly assigned for 28-d experimental period, to 2 groups, viz. a control (C diet), and an experimental (E diet) with the additional inclusion of 50 g DGP / kg diet. The FA composition wasanalysed by gas chromatography and all the spectra were recorded by spectrophotometry. The results of the study prove that the DGP, by its high content of polyunsaturated fatty acids (PUFA, over 60% of total FAME) and by the active principles such as polyphenols (lmax =273 nm), is a valuable feed which improvedfatty acids composition of LD muscle. In addition, the polyphenols from GP changed in plasma, maximum changes from 273 nm to 279 nm. These properties were reflectedin a positive influence on muscle n-3 FA composition (>1.27 times in DGP group than control group, p=0.02), particularly alpha-linolenicFA (>1.35 times) and eicosapentaenoic FA (>1.30 times than C diet), known for their health benefits.
Cardiovascular disease (CVD) is one of the most prevalent noncommunicable diseases in humans. Different studies have identified dietary procyanidins as bioactive compounds with beneficial properties against CVD by improving lipid homeostasis, among other mechanisms. The aim of this work was to assess whether grape seed procyanidin consumption at a physiological dose during the perinatal period could influence the CVD risk of the offspring. Wistar rat dams were treated with a grape seed procyanidin extract (GSPE; 25mg/kg of body weight per day) or vehicle during gestation and lactation. The adult male offspring of GSPE-treated dams presented decreased high-density lipoprotein cholesterol (HDL-C) levels, increased total cholesterol-to-HDL-C ratios and an exacerbated fasting triglyceride-to-HDL-C ratios (atherogenic index of plasma) compared to the control group. Impaired reverse cholesterol transport (RCT) was evidenced by the accumulation of cholesterol in skeletal muscle and by decreased fecal excretion of cholesterol and bile acids, which was consistent with the observed mRNA down-regulation of the rate-limiting enzyme in the hepatic bile acid synthesis pathway Cyp7A1. Conversely, GSPE programming also resulted in up-regulated gene expression of different key components of the RCT process, such as hepatic Npc1, Abcg1, Abca1, Lxra, Srebp2, Lcat, Scarb1 and Pltp, and the repression of microRNA miR-33a expression, a key negative controller of hepatic RCT at the gene expression level. Our results show that maternal intake of grape procyanidins during the perinatal period impacts different components of the RCT process, resulting in increased CVD risk in the adult offspring.
Grape pomace is a potential source of natural antioxidant and antimicrobial agents. Phenolic compounds, antioxidant, and antibacterial properties of pomace extracts from four Virginia-grown grape varieties were investigated. White grape pomaces had higher (P < 0.05) solvent extraction yield than red varieties. Concentrations of total phenolic (TPC), total flavonoid (TFC), total anthocyanin (TAC), tannins, condensed tannins (CT), as well as antioxidant capacities (DPPH• and ABTS•+free radical scavenging) differed (P < 0.05) among four pomace extracts. ABTS•+ scavenging capacity was positively correlated with TPC, TFC, tannins, and CT (P < 0.05), whereas DPPH• capacity was positively correlated with TAC (P < 0.05). Nine flavonoid compounds were identified, of which catechin and epicatechin were the two most abundant. Antibacterial activity was observed against Listeria monocytogenes ATCC 7644 and Staphylococcus aureus ATCC 29213, but not against Escherichia coli O157:H7 ATCC 3510 and Salmonella typhimurium ATCC 14028. L. monocytogenes was more susceptible than S. aureus.
In the present work, a comparative study of the detailed phenolic profile of fruit and juice samples from an Asturian cider apple breeding program was carried out. To achieve this, a fast, selective and sensitive UHPLC-DAD strategy was developed and validated. The proposed method allowed determining 49 polyphenols in apple samples and 41 phenolic compounds in apple juice samples in 18 min. Furthermore, six minor flavonoids have been quantified for the first time in apples: phloretin-hexosyl-hexoside, isorhamnetin-3-O-galactoside, isorhamnetin-3-O-glucoside, isorhamnetin-3-O-arabinopyranoside, isorhamnetin-3-O-arabinofuranoside and isorhamnetin-3-O-rhamnoside. The selectivity and reliability of this methodology allowed us to apply it in a successful manner to select the most interesting descendants from a progeny of ‘Meana’ × ‘Florina’ (a cider and a dessert apple, respectively) in terms of their phenolic composition. Descendants X9701-349, 119, 370, 120 and 069 could be proposed for cider production, since they exhibited a higher phenolic content than ‘Meana’ apple juice. Although flavan-3-ol, procyanidin and dihydrochalcone levels were similar to those observed in ‘Meana’ apple, flavonol levels increased slightly. Furthermore, it is worth noting that hydroxycinnamic acid concentration was up to three times higher. This fact could lead to an increase in cider astringency and color, as well as in cider aroma. Thus, this methodology is proposed to be applicable to the determination of the phenolic profile in other fruit and/or plant extracts.
With an objective of developing a safe and efficient method to extract proanthocyanidins products from pomegranate peel for use in nutraceuticals or as food additives, the effects of extraction parameters on the production efficiency, product properties, and extraction kinetics were systematically studied. The results showed that both extraction temperature and water-material ratio had significant effects on the proanthocyanidins content, but the yield was significantly affected only by temperature. The moderate temperature and water-material ratio were beneficial to maintain high proanthocyanidins scavenging activity and good product quality. The second-order extraction and Arrhenius kinetic models were developed and successfully used to predict the proanthocyanidins yield for given conditions tested. Extraction temperature of 60 degrees C, water-material ratio of 30: 1 g g(-1), and time of 10 min are recommended for proanthocyanidins extraction from pomegranate peel, which corresponded to the highest yield of 40.6 mg g(-1) and content of 89.1 mg g(-1) having a scavenging activity of 31.5 g g(-1), and an attractive reddish yellow color.
Thrombosis is considered to be closely related to several diseases such as atherosclerosis, ischemic heart disease and stroke, as well as rheumatoid arthritis, hyperuricemia, and various inflammatory conditions. More and more studies have been focused on understanding the mechanism of molecular and cellular basis of thrombus formation as well as preventing thrombosis for the treatment of thrombotic diseases. In reality, there is considerable interest in the role of natural products and their bioactive components in the prevention and treatment of thrombosis related disorders. This paper briefly describes the mechanisms of thrombus formation on three aspects, including coagulation system, platelet activation, and aggregation, and change of blood flow conditions. Furthermore, the natural products for antithrombosis by anticoagulation, antiplatelet aggregation, and fibrinolysis were summarized, respectively.
The aim of the present study was to test whether the administration of a grape seed procyanidin extract (GSPE) during pregnancy and lactation, at doses extrapolated to human consumption, programs male offspring toward improved metabolism in adulthood. For this purpose, female rats were fed a normal-fat diet (NFD) and treated with either GSPE (25 mg kg(-1) of body weight/day) or vehicle during gestation and lactation. The metabolic programming effects of GSPE were evaluated in the male offspring fed NFD from 30 to 170 days of life. No changes were observed in body weight, adiposity, circulating lipid profile and insulin sensitivity between the offspring of dams treated with GSPE (STD-GSPE group) and their counterparts (STD-veh). However, the STD-GSPE offspring had lower circulating levels of C-reactive protein and lower respiratory quotient values, shifting whole-body energy catabolism from carbohydrate to fat oxidation. Furthermore, the STD-GSPE animals also exhibited increased levels of total and phosphorylated AMP-activated protein kinase (AMPK) and an over-expression of the mRNA levels of key genes related to fatty acid uptake (Fatp1 and CD36) and β-oxidation (pparα and had) in skeletal muscle. Our results indicate that GSPE programs healthy male offspring towards a better circulating inflammatory profile and greater lipid utilisation in adulthood. The metabolic programming effects of GSPE that are related to the enhancement of fatty acid oxidation in skeletal muscle seem to be mediated, at least in part, by AMPK. These findings could be of relevance in the prevention of pathologies associated to lifestyle and aging, such as obesity and insulin resistance.
Copyright © 2015. Published by Elsevier Inc.
Flavonol (−)-epicatechin and its derived dimer procyanidin B2, present in high amounts in cocoa products, have been shown to exert beneficial effects on the heart and cardiovascular system; however, their mechanism of action has not been fully elucidated. We studied effects of (−)-epicatechin and procyanidin B2 on the oxidative phosphorylation of isolated rat heart mitochondria. (−)-Epicatechin and procyanidin B2 had stimulating effect (up to 30% compared to control) on substrate-driven (State 2) mitochondrial respiration. Their effect was dependent on the respiratory substrates used. (−)-Epicatechin at higher concentrations (from 0.27 µg/mL) significantly decreased (up to 15%) substrate- and ADP-driven (State 3) mitochondrial respiration in case of pyruvate and malate oxidation only. Procyanidin B2 (0.7–17.9 ng/mL) inhibited State 3 respiration rate up to 19%, the most profound effect being expressed with succinate as the substrate. (−)-Epicatechin at concentrations of 0.23 µg/mL and 0.46 µg/mL prevented loss of the cytochrome
c
from mitochondria when substrate was succinate, supporting the evidence of membrane stabilizing properties of this flavonol. Thus, both (−)-epicatechin and procyanidin B2 directly influenced mitochondrial functions and the observed effects could help to explain cardiometabolic risk reduction ascribed to the consumption of modest amounts of cocoa products.
There is now a large body of evidence that platelets are central actors of inflammatory reactions. Indeed, platelets play a significant role in a variety of inflammatory diseases. These diseases include conditions as varied as atherosclerosis, arthritis, dermatitis, glomerulonephritis, or acute lung injury. In this context, one can note that inflammation is a convenient but imprecise catch-all term that is used to cover a wide range of situations. Therefore, when discussing the role of platelets in inflammation, it is important to clearly define the pathophysiological context and the exact stage of the reaction. Inflammatory reactions are indeed multistep processes that can be either acute or chronic, and their sequence can vary greatly depending on the situation and organ concerned. Here, we focus on how platelets contribute to inflammatory reactions involving recruitment of neutrophils and/or macrophages. Specifically, we review past and recent data showing that platelets intervene at various stages of these reactions to regulate parameters such as endothelial permeability, the recruitment of neutrophils and macrophages and their effector functions, as well as inflammatory bleeding. The mechanisms underlying these various modulating effect of platelets are also discussed.
Spatholobus suberectus (SS) is an excellent functional and medicinal food source of dietary procyanidins, which have numerous health benefits. Ten procyanidin fractions with different polymerization degrees were prepared from SS. For the first time, trimers to 11-mers were detected in SS extracts, and their compositions were elucidated through thiolysis, ESI-MS and MALDI-TOF-MS analyses. The results determined that the mean polymerization degree (mDP) of the crude SS procyanidins was 5.2 and that the mass distribution of the monomer and the oligomers (mDP of 1.0–5.7) was 70.4%, whereas that of the polymers (mDP of 6.2–11.8) was 25.6%. Catechin and epicatechin were the main monomeric units with minor quantities of epigallocatechin and gallocatechin. The observed interflavan linkages were both A-type (minor type) and B-type (major type). The fractions enriched in the monomer and oligomers showed the highest activities, including antioxidant activity and inhibitory activities on both the proliferation of MCF-7 breast cancer cells and lactate dehydrogenase A (LDH-A). These results suggested that the monomer- and oligomer-enriched procyanidin fractions from SS could undergo further development to become a beneficial source of antioxidants, LDH-A inhibitors, and potential inhibitors of breast cancer.
Tea is rich in polyphenols and phenolics compounds that have been widely reported to have beneficial health effects. The aim of this study was to investigate the ability of catechins, major phenols in tea, to act as growth factors for Lactobacillus casei during lactic acid fermentation. Major catechins presented in tea extracts are gallocatechin, catechin, epigalocatechin, galocatechingalat, epicatechingalat, catechingalat. Different concentrations of green tea and black tea extracts have been added to MRS model media. Growth and viability of Lactobacillus casei was positively affected by the addition of green tea and black tea extracts. This indicates that green tea and black tea addition exert protective effect on Lactobacillus casei growth in MRS media, increasing the viability and biomass production, probably by acting as metabolic enhancer. This results indicated the posibility of using green tea and black tea as metabolic enhancers for the growth of Lactobacillus casei.Â
Plasticized wheat starch (PWS)/cellulose fiber composites were formulated and tested in thermoforming applications. The composites have increased modulus and strength, improved temp. stability and glass transition shifts. Thermoformed trays were tested in storage conditions from 4° to ambient temp.; the composite based-materials show reduced aging compared with PWS alone. [on SciFinder(R)]
The production of new blood vessels (angiogenesis) is an important stage in the growth and spread of cancerous tumors. Anti-angiogenesis is one strategy for controlling tumor progression. This study evaluated the antioxidant and antiangiogenic activities of a proanthocyanidins (PAs) extract from Choerospondias axillaris peels. HPLC-MS analysis revealed that numerous oligomeric forms of the PAs were detected in the PAs extract, including dimers, trimers, tetramers and flavan-3-ol monomers. The PAs extract possessed appreciable free radical scavenging activity (IC50/DPPH =164 ± 7 µg/mL, IC50/ABTS =154 ± 6 µg/mL), potent reducing power (0.930 ± 0.030 g AAE/g), and strong cellular antioxidant activity (EC50 =10.2 ± 1.4 and 38.9 ± 2.1 µg/mL without or with PBS wash, respectively). It could also retard various stages of angiogenesis, such as the migration of endothelial cells and the creation of tubes without causing toxicity to the cells. Regarding intracellular signal transduction, the PAs extract attenuated the phosphorylation of Akt, ERK, and p38MAPK dose-dependently in endothelial cells from human umbilical veins. In transgenic zebrafish embryo, new blood vessel formation was suppressed by PAs extract in a concentration-dependent manner at 72 h post fertilization. Thus, these results suggest that PAs from Choerospondias axillaris peels could be a good source of natural inhibitors to target angiogenesis.
Serum C-reactive protein (CRP) is a biomarker for chronic inflammation and a sensitive risk factor for cardiovascular diseases. Though CRP has been reported to be related to food intake, there is no documentation of a direct association with flavonoid intake, We aimed to test the associations between dietary flavonoid intake and serum CRP concentrations among U.S. adults after adjusting for dietary, sociodemographic, and lifestyle factors. Data from the NHANES 1999-2002 were used for this cross-sectional study. Subjects were >= 19-y-old adults (n = 8335), and did not include pregnant and/or lactating women. Flavonoid intake of U.S. adults was estimated by the USDA flavonoid databases matched with a 24-h dietary recall in NHANES 1999-2002. The serum CRP concentration was higher in women, older adults, blacks, and smokers, and in those with high BMI or low exercise level, and in those taking NSAID, than in their counterparts (P < 0.01). Intakes of apples and vegetables were inversely associated with serum CRP concentrations after adjusting for covariates (P < 0.05). Total flavonoid and also individual flavonol, anthocyanidin, and isoflavone intakes were inversely associated with serum CRP concentration after adjusting for the covariates (P < 0.05). Among the flavonoid compounds investigated, quercetin, kaempferol, malvidin, peonidin, daidzein, and genistein had inverse associations with serum CRP concentration (P < 0.05). These associations did not change even after the additional adjustment for fruit and vegetable consumption. Our findings demonstrate that intake of dietary flavonoids is inversely associated with serum CRP concentrations in U.S. adults. Intake of flavonoid-rich foods may thus reduce inflammation-mediated chronic diseases.
Polyphenols are abundant micronutrients in our diet, and evidence for their role in the prevention of degenerative diseases is emerging. Bioavailability differs greatly from one polyphenol to another, so that the most abundant polyphenols in our diet are not necessarily those leading to the highest concentrations of active metabolites in target tissues. Mean values for the maximal plasma concentration, the time to reach the maximal plasma concentration, the area under the plasma concentration-time curve, the elimination half-life, and the relative urinary excretion were calculated for 18 major polyphenols. We used data from 97 studies that investigated the kinetics and extent of polyphenol absorption among adults, after ingestion of a single dose of polyphenol provided as pure compound, plant extract, or whole food/beverage. The metabolites present in blood, resulting from digestive and hepatic activity, usually differ from the native compounds. The nature of the known metabolites is described when data are available. The plasma concentrations of total metabolites ranged from 0 to 4 mumol/L with an intake of 50 mg aglycone equivalents, and the relative urinary excretion ranged from 0.3% to 43% of the ingested dose, depending on the polyphenol. Gallic acid and isoflavones are the most well-absorbed polyphenols, followed by catechins, flavanones, and quercetin glucosides, but with different kinetics. The least well-absorbed polyphenols are the proanthocyanidins, the galloylated tea catechins, and the anthocyanins. Data are still too limited for assessment of hydroxycinnamic acids and other polyphenols. These data may be useful for the design and interpretation of intervention studies investigating the health effects of polyphenols.
Procyanidins (PAs) are polyphenols in plant food that have many health benefits, including cancer prevention, cardiovascular protection and diabetes prevention. PAs have been known to have low oral bioavilability. In this review, we summarize the published results on the ADME (absorption, distribution, metabolism and excretion) of PAs in vivo and in vitro. After oral administration, in the stomach the decomposition of PAs is highly dependent on the pH value of gastric juice, which is also affected by food intake. In the small intestine, PA polymers and oligomers with DP > 4 are not directly absorbed in vivo, but minor PA monomers and dimers could be detected in the plasma. Methylated and glucuronidated PA dimers and monomers are the main metabolites of PAs in plasma. In the colon, PAs are catabolized by colonic microflora into a series of low molecular weight phenolic acids, such as phenyl valerolactone, phenylacetic acids and phenylpropionic acids. We reviewed the degradation of PAs in gastric digestion, the absorption of PAs in the small intestine and the metabolic pathway of PAs by colonic microflora. To clearly explain the in vivo pharmacokinetics of PAs, a systematic comparative analysis on previously published data on PAs was conducted.
As evidenced by a growing number of respective clinical trials, a promising and increasingly valued approach to cancer prevention is chemoprevention which is based on using synthetic, semisynthetic, or natural compounds with the aim of preventing, delaying, arresting, or reversing carcinogenesis. Research carried out in the last two decades indicates that natural polyphenols isolated from plants (as well as their derivatives and synthetic analogs) exhibit pleiotropic actions toward cancer cells and therefore they could be used in both cancer prevention and therapy. This review discusses selected covalent modifications of polyphenols as a means for increasing their anticancer potential in relation to the parent compounds. The modifications include hydroxylation, methylation, acylation, and galloylation, among others. They were demonstrated to enhance cytotoxic, pro-oxidant, antiproliferative, proapoptotic, proauthophagic, and antimigratory activities of phenolics toward various cancer cell lines in vitro. Importantly, some derivatives proved to suppress tumor growth and metastasis in animal models more strongly than the parent compounds. Some of the above-mentioned covalent modifications were also shown to increase absorption and tissue distribution of tested phenolic compounds in vivo. Anticancer clinical trials with polyphenol derivatives therefore seem warranted.
Proanthocyanidins (PAs) are the most abundant flavonoids in the human diet. Several epidemiological studies connect PA consumption and health benefits and the designation of PAs as healthy compounds started at the early stages of the 20th century. The beneficial health properties of PAs are attributed to their conjugated and colonic metabolites. Therefore, gut microbial compositions can determine the effectiveness of PAs. Reciprocally, dietary polyphenols can act as prebiotics. Recently, it has also been described that PAs modulate the circadian rhythm. Biochemical and epigenetic mechanisms, including the modulation of microRNAs, allow PAs to modulate cell functionality. PA effects in metabolic diseases are also reviewed. © 2016 BioFactors, 2016.
An experiment combining the Taguchi methodology with the response surface methodology to optimize the Pressurized Liquid Extraction (PLE) of proanthocyanidins from Taiwan pines was conducted. A L18 orthogonal array was selected to investigate the total yield and the amount of proanthocyanidins. Experimental results showed that the extraction temperature most significantly affected the efficiency of extraction, but that a higher temperature also caused decomposition of bioactive components. Optimum conditions were identified as 20% EtOH, 140°C, 750 psig, and 1.5 h. The PLE total yield, proanthocyanidins content and total flavonoids were 2.09, 2.07, and 2.01 times greater than those obtained using a 50% EtOH conventional extraction method. Hot pressurized extraction has the advantages of low energy and high yield of bioactive compounds. The antioxidant activities of several extracts from two Taiwan pine-needles were individually evaluated for scavenging of DPPH free radicals and superoxide anion radicals, and for the inhibition of lipid peroxidation. The results revealed that both PLE M (Pinus morrisonicola) and PLE T (Pinus taiwanensis) extracted from two fresh pine needles scavenged 78.91% of DPPH free radicals. Air-dried pine needles also strongly inhibited superoxide anion radicals. The purification of four anthocyanidins from a PLE T extract was initially tested using HP-20 resin solid phase extraction and showed little enhancement. The isolation, purification and antioxidative mechanism of active components from pine needles need to be further investigated.
The barberry (Berberis vulgaris) extract which is a rich source of anthocyanins was used for spray drying encapsulation with three different wall materials, i.e., combination of maltodextrin and gum Arabic (MD + GA), maltodextrin and gelatin (MD + GE), and maltodextrin (MD). Response Surface Methodology (RSM) was applied for optimization of microencapsulation efficiency and physical properties of encapsulated powders considering wall material type as well as different ratios of core to wall materials as independent variables. Physical characteristics of spray-dried powders were investigated by further analyses of moisture content, hygroscopicity, degree of caking, solubility, bulk and absolute density, porosity, flowability and microstructural evaluation of encapsulated powders. Our results indicated that samples produced with MD + GA as wall materials represented the highest process efficiency and best powder quality; the optimum conditions of microencapsulation process for barberry anthocyanins were found to be the wall material content and anthocyanin load of 24.54% and 13.82%, respectively. Under such conditions, the microencapsulation efficiency (ME) of anthocyanins could be as high as 92.83%.
In this research, encapsulation efficiency of cress seed gum (CSG) as a native hydrocolloid was compared with Arabic gum (AG) and maltodextrin (dextrose equivalent of 20 (M20), and 7 (M7)) for saffron (Crocus sativus) petal's extract by freeze drying method. Combinations of CSG-M20, AG-M20, and M7-M20 with ratios of 50:50 and M20 alone (100%) were used as wall materials. A mixture of 1:5 (based on dry matter) between core (concentrated anthocyanin extract of saffron petal) and wall materials were freeze dried and stability of encapsulated anthocyanins along with color parameters (a∗, b∗, L∗, C, H° and TCD) of final powders were measured during 10 weeks of storage (at 35 °C as an accelerated method). Total anthocyanins were determined through pH differential method every week. Four prepared formulations of encapsulated powders didn't show any significant differences (P > 0.01) in terms of total anthocyanin content measured immediately after production and after 10 weeks storage. AG-M20 mixture and M20 alone showed the highest and lowest TCD, respectively. The mixture of CSG-M20 in comparison with AG-M20 and M20 had the same protecting effect (P < 0.01) but showed a relatively high TCD (9.33).
Microsphere technology serves as an efficient and effective platform for cell applications (in vitro cell culture and in vivo cell delivery) due to its mimicry of the 3D native environment, high surface area:volume ratio, and ability to isolate the entrapped cells from the environment. Properties of cell-laden microspheres are determined by the type of application and the cell. While high cell densities are preferable for large-scale therapeutic biomolecule production in vitro, an immunoprotective barrier is most important for allogeneic pancreatic islet transplantation into patients. Furthermore, the biological cells require a suitable microenvironment in terms of its physical and biochemical properties. Here, we discuss applications of cell-laden microspheres and their corresponding design parameters.
The development of a multi-purpose four steps-cascading biorefinery scheme for the valorization of a red grape pomace (GP) was proposed. The consecutive processes were respectively dedicated to (a) the recovery of polyphenols by supercritical CO2 extraction, (b) the production of volatile fatty acids (VFAs) by anaerobic acidogenic digestion, (c) the exploitation of produced VFAs as the precursors for the biotechnological production of polyhydroxyalkanoates (PHAs) and (d) the production of a CH4-rich biogas by the anaerobic digestion of solid leftovers from the acidogenic process. More than 2.7 g of total polyphenols (as Gallic acid equivalents) per 100 g of dry matter were extracted. High contents of valuable proanthocyanidins occurred in the recovered polyphenolic fraction. The dephenolized GP was anaerobically digested under batch acidogenic conditions, obtaining about 20 g L-1 of total VFAs in the liquid effluent. The latter matrix was employed to feed a pure culture of a Cupriavidus necator strain,
Plants and their biologically active chemical constituents present numerous opportunities for improving animal production by inclusion in the diet. In recent years, interest has grown in the antioxidant and antimicrobial properties of a number of polyphenols found in different plants. The by-products of the wine industry (grape pomace, skin and seeds) and wine polyphenol extracts contain a wide range of bioactive compounds. However, studies on grape by-products are very limited, despite their richness polyphenolic substances. In this context, the purpose of this review is summarize recent advances of research in grape by-products including the phenolic composition, mechanism of intestinal and hepatic conjugation, plasma transport and elimination in bile and urine, and biological activities such as antioxidant and antimicrobial effect. Given their antioxidant activity, the inclusion of these by-products in feed rations would not only enhance the oxidative stability of the meat and reduce the amount of additives like vitamin E but also improve meat quality through direct addition of these natural antioxidants, thereby helping to meet consumer demand for healthier meat products. With respect to antimicrobial activity, they enhance the growth of specific beneficial bacteria strains in the intestinal tract while competitively excluding certain pathogenic bacteria.
There is increasing consumer dissatisfaction regarding the quality of peaches due to the rapid decay that these fruit undergo after harvest.This study aimed to determine the phenolics contents and provide sensory characterisations of four commercial melting flesh (MF) and four commercial non-melting flesh (NMF) peach cultivars. Low molecular weight phenolic compounds (LMWPC) were determined by high performance liquid chromatography coupled to a diode array detector (HPLC-DAD). A trained sensory panel with 12 members evaluated the principal quality attributes of each cultivar. Skin ground colour was different among the MF and NMF cultivars. Fifteen LMWPC were identified in peach flesh tissue. Procyanidin gallate 1, procyanidin gallate 3, procyanidin B3, and flavonoids 1, 2, and 3 were detected in all eight cultivars, while gallic acid was present only in 'Elegant Lady'.Two main clusters were formed based on the 15 LMWPC observed, but no correlation with flesh type was observed. On the other hand, a principal components analysis (PCA) based on sensory attributes showed a clear segregation between the MF and NMF cultivars. The NMF cultivars were associated with "texture" and a low score for "visual appearance", while the MF cultivars were associated with attributes such as "sweetness", "juiciness", and "flavour". The types and amounts of LMWPC were not correlated with flesh type in both these peach cultivars (MF and NMF). LMWPC profiles were therefore more dependent on genetic background than on the specific MF or NMF trait.
Garcinia brasiliensis, a plant native to the Brazilian Amazon Rainforest, is used in traditional medicine to treat inflammation of the urinary tract, peptic ulcers, arthritis and other conditions.
The purposes of this study were to analyze the chemical constituents of G. brasiliensis branches and leaves and to evaluate the potential of isolated compounds to act as inhibitors of both the oxidative burst of stimulated neutrophils and oxidative damage in human erythrocyte membranes to verify the antioxidant and anti-inflammatory effects of this plant.
Neutrophils were isolated from the blood of healthy donors by Ficoll-Paque density gradient centrifugation. Superoxide anion and total reactive oxygen species (ROS) produced by stimulated neutrophils were measured by WST-1 reduction and luminol-enhanced chemiluminescence assays, respectively. Radical-induced lipoperoxidation and hemolysis were performed using erythrocytes from the blood of healthy donors. Compounds were isolated from G. brasiliensis branches and leaves by HPLC microfractionation, and structure elucidation of the isolated compounds was performed based on NMR and HR-MS analyses.
The biflavonoids procyanidin, fukugetin, amentoflavone and podocarpusflavone isolated from G. brasiliensis showed potent inhibitory effects on the oxidative burst of human neutrophils, inhibiting ROS production by 50% at 1 μmol L(-1). These biflavonoids also proved to be potent inhibitors of hemolysis (with 88±7% inhibition at 50 µmol L(-1) for procyanidin) and lipid peroxidation in human erythrocytes, with a malondialdehyde level (a biomarker of oxidative stress) of 8.5±0.3nmol/mg Hb at 50µmol L(-1) for procyanidin.
These findings indicate that the biflavonoids extracted from G. brasiliensis branches and leaves modulate oxidative stress via inhibition of NADPH oxidase and ROS production by stimulated human neutrophils. Furthermore, the biflavonoids exhibited potent inhibition of oxidant hemolysis and lipid peroxidation induced by AAPH in human erythrocytes. Therefore, these studies suggest the use of G. brasiliensis extract as an antioxidant and anti-inflammatory agent.
Copyright © 2015. Published by Elsevier Ireland Ltd.
Purification and bioassay-guided fractionation were employed to isolate proanthocyanidins with antioxidant activity from peanut skin (Arachis hypogaea Runner 886). The crude extract was prepared with acetone (60% v/v) and purified using chromatographic methods, including a semipreparative HPLC technique. As a result, two proanthocyanidins were isolated and identified using NMR, epicatechin-(2 β→O→7, 4 β→8)-catechin (proanthocyanidin A1) and epicatechin-(β→2 O→7, 4 β→8)-epicatechin (proanthocyanidin A2). Despite the structural similarity, differences were observed in their antioxidant activity. Proanthocyanidin A1 proved to be more active, with EC50 value for DPPH radical scavenging of 18.25μg/mL and reduction of Fe(3+)-TPTZ complex of 7.59mmol/g, higher than that of synthetic antioxidant BHT. This compound evaluated by ABTS(+) was similar to that of natural quercetin. Therefore, peanut skin is an important source of bioactive compounds that may be used as a mild antioxidant for food preservation.
Copyright © 2015 Elsevier Ltd. All rights reserved.
Animal feed provides a range of antioxidants that help the body building an integrated antioxidant system
responsible for a prevention of damaging effects of free radicals and products of their metabolism. Vitamin E is
considered to be the main chain-breaking antioxidant located in the membranes and effectively protecting them
against lipid peroxidation. Recently, various polyphenol compounds, especially flavonoids, have received
substantial attention because of their antioxidant activities in various in vitro systems. However, it was shown
that flavonoid compounds are poorly absorbed in the gut and their concentrations in target tissues are too low to perform an effective antioxidant defences. The aim of the present paper is to review existing evidence about
possible roles of various plant extracts provided with the diet in animal/poultry nutrition with a specific emphasis
to their antioxidant activities.
Procyanidins are available in the diet from sources such as cocoa and grapes. Procyanidins are unique in that they are comprised of repeating monomeric units and can exist in various degrees of polymerization. The degree of polymerization plays a role in determining the biological activities of procyanidins. However, generalizations cannot be made regarding the correlation between procyanidin structure and bioactivity because the size-activity relationship appears to be system dependent. Our aim was to screen fractions of procyanidins with differing degrees of polymerization in vitro for anti-inflammatory activities in models of colonic inflammation. Monomeric, oligomeric and polymeric cocoa procyanidin fractions were screened using cell models of disrupted membrane integrity and inflammation in human colon cells. High-molecular-weight polymeric procyanidins were the most effective at preserving membrane integrity and reducing secretion of interleukin-8 in response to inflammatory stimuli. Conversely, oligomeric procyanidins appeared to be the least effective. These results suggest that polymeric cocoa procyanidins may be the most effective for preventing loss of gut barrier function and epithelial inflammation, which are critical steps in the pathogenesis of metabolic endotoxemia, inflammatory bowel disease and colon cancer. Therefore, further investigations of the potential health-protective benefits of cocoa procyanidins with distinct degrees of polymerization, particularly high-molecular-weight procyanidins, are warranted.
Copyright © 2015. Published by Elsevier Inc.
The main procyanidins, including dimeric B2 and B5, trimeric C1, tetrameric and pentameric procyanidins, were isolated from unroasted cocoa beans (Theobroma cacao L.) using various techniques of countercurrent chromatography, such as high-speed countercurrent chromatography (HSCCC), low-speed rotary countercurrent chromatography (LSRCCC) and spiral-coil LSRCCC. Furthermore, dimeric procyanidins B1 and B7, which are not present naturally in the analysed cocoa beans, were obtained after semisynthesis of cocoa bean polymers with (+)-catechin as nucleophile and separated by countercurrent chromatography. In this way, the isolation of dimeric procyanidin B1 in considerable amounts (500mg, purity>97%) was possible in a single run. This is the first report concerning the isolation and semisynthesis of dimeric to pentameric procyanidins from T. cacao by countercurrent chromatography. Additionally, the chemical structures of tetrameric (cinnamtannin A2) and pentameric procyanidins (cinnamtannin A3) were elucidated on the basis of (1)H NMR spectroscopy. Interflavanoid linkage was determined by NOE-correlations, for the first time.
Copyright © 2015 Elsevier Ltd. All rights reserved.
The effect of fruit size (<26 mm, 26-28 mm, >28 mm) and fruit colour (Ctifl 4 and Ctifl 6) of ‘Kordia’ sweet cherry on composition of nutritive (sugars, organic acids) and bioactive (phenolics) compounds, on content of vitamin C, total phenolic content (TPC) and total antioxidant activity (TAA) was evaluated. The compositional data analysis was used for comparing relative contents of chemical compounds. The differences in average composition were examined on the basis of multivariate analysis of variance and further analysis of variance for each isometric log-ratio transformed variable. Five compounds have been identified for the first time: dicaffeoylquinic acid ([M−H]− at m/z 515), procyanidin trimer ([M−H]− at m/z 865), quercetin-3-(2G-glucosyl-rutinoside) ([M−H]− at m/z 771), quercetin-3-galactoside ([M−H]− at m/z 463) and kaempferol-3-glucoside ([M−H]− at m/z 447). In the composition of sweet cherry ‘Kordia’ fruit bioactive compounds represented from 0.6% to 0.8%. The fruit colour modifies the chemical composition of phytochemicals more than fruit size; the two variables were correlated. More coloured fruit were larger, with better pomological traits and changed composition of nutritive compounds and phenolics.
