DOCSLIB.ORG

Oligomeric Proanthocyanidin Complexes: History, Structure, and Phytopharmaceutical Applications Anne Marie Fine, CPA, ND Candidate 2000

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Oligomeric Proanthocyanidin Complexes: History, Structure, and Phytopharmaceutical Applications Anne Marie Fine, CPA, ND Candidate 2000 Oligomeric Proanthocyanidin Complexes: History, Structure, and Phytopharmaceutical Applications Anne Marie Fine, CPA, ND Candidate 2000 Abstract Considerable recent research has explored therapeutic applications of oligomeric proanthocyanidin complexes (OPCs), naturally occurring plant metabolites widely available in fruits, vegetables, nuts, seeds, flowers, and bark. OPCs are primarily known for their antioxidant activity. However, these compounds have also been reported to demonstrate antibacterial, antiviral, anticarcinogenic, anti-inflammatory, anti-allergic, and vasodilatory actions. In addition, they have been found to inhibit lipid peroxidation, platelet aggregation, capillary permeability and fragility, and to affect enzyme systems including phospholipase A2, cyclooxygenase, and lipoxygenase. Based on these reported findings, OPCs may be a useful component in the treatment of a number of conditions. (Altern Med Rev 2000;5(2):144-151) Introduction In 1534, a French explorer, Jacques Cartier, led a winter expedition up the St. Lawrence River in New York. The group soon found themselves trapped by ice and forced to survive on salted meat and hard biscuits. The crew began to show signs and symptoms of scurvy, long before anyone knew what caused it. Due to a chance meeting with a Native American, who showed them how to make a tea from the bark and needles of pine trees, the men survived.1 Professor Jacques Masquelier, of the University of Bordeaux, France, read the book eventually written by Cartier, became intrigued with the story and postulated that the pine bark must contain vitamin C as well as flavonoids having ascorbate-like effects. Thus began an ex- haustive study of these compounds which Masquelier named pycnogenols, a term no longer used in the scientific community today except as a trademark for OPCs derived from French maritime pine bark. Today they are known as oligomeric proanthocyanidin complexes (OPCs) or procyanidolic oligomers (PCOs). Professor Masquelier confirmed the structure, effects, and lack of toxicity of these proanthocyanidins.1 Masquelier went on to patent the method of extracting OPCs from pine bark in 1951, and from grape seeds in 1970 (which research has supported as the preferential source).1 Anne Marie Fine, CPA, ND (Cand. 2000)- Vice President of Finance, International Clinical Research Center, Inc. Correspondance address: 13910 N. Frank Lloyd Wright Blvd., Ste. 2A #105, Scottsdale, AZ 85260 Page 144 Alternative Medicine Review ◆ Volume 5 Number 2 ◆ 2000 Copyright©2000 Thorne Research, Inc. All Rights Reserved. No Reprint Without Written Permission Oligomeric Proanthocyanidins Table 1: Main Classes of Polyphenolic Compounds Class Basic Skeleton Basic Structure Simple phenols C6 OH Benzoquinones C6 O O Phenolic acids C6-C1 COOH Acetophenones C6-C2 COCH3 Phenylacetic acids C6-C2 CH2-COOH Hydroxycinnamic acids C6-C3 CH=CH-COOH Phenylpropenes C6-C3 CH2-CH=CH2 O O Coumarins, isocoumarins C6-C3 O O O Chromones C6-C3 O O Naftoquinones C6-C4 O O Xanthones C6-C1-C6 O Stilbenes C6-C2-C6 O Anthraquinones C6-C2-C6 O O Flavonoids C6-C3-C6 Lignans, neolignans (C6-C3)2 Lignins (C6-C3)n Adapted from: Bravo L. Polyphenols: chemistry, dietary sources, metabolism, and nutritional significance. Nutrition Reviews 1998;56(11):317-333. Alternative Medicine Review ◆ Volume 5, Number 2 ◆ 2000 Page 145 Copyright©2000 Thorne Research, Inc. All Rights Reserved. No Reprint Without Written Permission Table 2: Classification of Food Flavonoids Flavonoid Basic Structure Molecular Structure O Proanthocyanidins are naturally Anthocyanidin occurring plant metabolites widely OH O O O available in fruits, vegetables, nuts, Aurones CH C seeds, flowers, and bark.2 Other plant O OCH3 sources of proanthocyanidins include O wine, cranberries, and the leaves of bil- O Biflavonoids berry, birch, ginkgo, and hawthorne. O Also known as procyanidins, these sub- O stances are the main precursors of the Chalcones blue-violet and red pigments in plants. O These compounds are part of a specific group of polyphenolic com- pounds – the flavonoids (Table 1).3 Fla- Dihydrochalcones vonoids are further categorized by sub- O groups. Proanthocyanidins belong to the O category known as condensed tannins, Dihydroflavonol OH one of the two main categories of plant O tannins (Table 2).3 Tannins are highly O hydroxylated structures that can form Flavandiol OH insoluble complexes with carbohydrates or leucoanthocyanidin OH and protein, a measure of their astrin- O gency, based on their ability to cause Flavanol 3 OH precipitation of salivary proteins. The polyphenolics, including proantho- O cyanidins, form a considerable portion Flavanones of the tannins found in wine, and in par- O O ticular contribute heavily to the color Flavones and flavor of red wines. Proanthocyanidins are high-mo- O O lecular-weight polymers comprised of Flavonols the monomeric unit flavan-3-ol ( (+)cat- OH O echin and (-) epicatechin). Oxidative O O condensation occurs between carbon C- Isoflavonoids 4 of the heterocycle and carbons C-6 or O O C-8 of the attached A and B rings (Fig- ure 1).3 The procyanidins B1-B4, char- O acterized by the C4-C8 linkage, are the most common dimers, occasionally ac- Proanthocyanidins companied by corresponding C4-C6 or condensed tannins O linked isomers (B5-B8) (Figure 2).4 At a symposium entitled “Free O Radicals in Biotechnology and Medicine” held in London in 1990, it was reported that esterification of (-)- Adapted from: Bravo L. Polyphenols: chemistry, dietary sources, metabolism, and epicatechin and procyanidin B2 by nutritional significance. Nutrition Reviews 1998;56(11):317-333 Page 146 Alternative Medicine Review ◆ Volume 5, Number 2 ◆ 2000 Copyright©2000 Thorne Research, Inc. All Rights Reserved. No Reprint Without Written Permission Oligomeric Proanthocyanidins Figure 1: Basic Structure and Numbering System of Flavonoids 3´ anticarcinogenic, anti-inflammatory, anti-al- lergic, and vasodilatory actions.2,12 2´ 4´ Proanthocyanidins have also been shown to B inhibit lipid peroxidation, platelet aggrega- 8 O 1´ tion, capillary permeability and fragility, and 5´ to affect enzyme systems including phos- 7 2 6´ pholipase A2, cyclooxygenase, and AC lipoxygenase.1,2,12,13 The free radical scavenging abilities 6 3 of proanthocyanidins have been well docu- 5 4 mented and command the most atten- tion.1,2,12,14 In vivo studies have shown grape seed proanthocyanidin extract is a better free radical scavenger and inhibitor of oxidative gallic acid increases their free radical tissue damage than vitamin C, vitamin E suc- scavenging ability. Information was also cinate, vitamin C and vitamin E succinate com- introduced revealing the dimeric bined, and beta carotene.12 Moreover, in vitro proanthocyanidins having the C4-C8 linkage experimental results have demonstrated have greater free radical scavenging activity proanthocyanidins have specificity for the hy- than the C4-C6 linkage, and that these gallate droxyl radical1,2 in addition to having the abil- esters are only found in the grape seed extract ity to non-competitively inhibit the activity of form. xanthine oxidase, a major generator of free Grape seed extract contains OPCs radicals,1,9,14 elastase, collagenase, hyalu- made up of dimers or trimers of (+)-catechin ronidase, and beta-glucuronidase.9 and (-)-epicatechin.4-6 The procyanidin dimers OPCs have also demonstrated prefer- are comprised of procyanidins B1, B2, B3, B4, ential binding to areas characterized by a high B5, B6, B7, and B8. There are six procyanidin content of glycosaminoglycans (epidermis, trimers which include procyanidin C1 and C2. capillary wall, gastrointestinal mucosa, etc.). Furthermore, several gallolyl procyanidins, This feature makes them useful for decreas- which are most commonly the gallate esters ing vascular permeability and enhancing cap- of the dimeric procyanidins, and some free illary strength, vascular function, and periph- gallic acid are present.4,5 Tetramers or greater eral circulation.13 of these flavonols would be known as poly- meric proanthocyanidins and the astringency Therapeutic Applications of the molecule would increase accordingly. Free radical damage has been strongly Therefore, oligomeric proanthocyanidins are associated with virtually every chronic degen- less astringent, bind less strongly to proteins, 5 erative disease, including cardiovascular dis- and are more soluble and mobile in the body. ease, arthritis, and cancer. Free radicals are highly reactive and cause tissue damage by Biological Properties reacting with polyunsaturated fatty acids found The biological properties of fla- in cellular membranes, nucleotides in DNA, vonoids, including proanthocyanidins, have and sulfhydryl bonds in proteins. Free radi- been extensively reviewed.2,7-9 In addition to cals may originate endogenously through nor- their free radical scavenging and antioxidant mal metabolism and exogenously from pol- activity,1,8,10,11 proanthocyanidins have been luted air, solvent-laden water, pesticide-laced reported to have antibacterial, antiviral, food, or radiation exposure. Alternative Medicine Review ◆ Volume 5, Number 2 ◆ 2000 Page 147 Copyright©2000 Thorne Research, Inc. All Rights Reserved. No Reprint Without Written Permission Figure 2: Structure of the Main Procyanidin Dimers from V. vinifera OH OH O O HO OH HO OH OH OH OH OH OH OH C O HO OH HO OH R1 R1 R2 R2 OH OH 1 2 1 2 Procyanidin B1 R =OH, R =H Procyanidin B3 R =OH, R =H 1 2 1 2 Procyanidin B2 R =H, R =OH Procyanidin B4 R =H, R =OH OH OH O O HO OH HO OH OH OH OH OH HO OH HO OH 2 2 R O R O R1 R1 HO HO OH OH 1 2 1 2 Procyanidin B5 R =H, R =OH Procyanidin B6 R =OH, R =H 1 2 1 2 Procyanidin B7 R =OH, R =H Procyanidin B8 R =H, R =OH Bombardelli E, Morazzoni P. Vitis vinifera. Fitoterapia 1995;66:291-317 Clearly, due to their antioxidant proanthocyanidins are the active ingredient in activity, the therapeutic potential of a proprietary pharmaceutical product sold in proanthocyanidins is quite broad. In Europe, France (Endotelon) used primarily for proanthocyanidins are used mainly for the microcirculatory disorders.
Load more

Recommended publications
  • Adaptive Radiations: from Field to Genomic Studies
    Adaptive radiations: From field to genomic studies Scott A. Hodges and Nathan J. Derieg1 Department of Ecology, Evolution, and Marine Biology, University of California, Santa Barbara, CA 93106 Adaptive radiations were central to Darwin’s formation of his phenotype–environment correlation, (iii) trait utility, and (iv) theory of natural selection, and today they are still the centerpiece rapid speciation. Monophyly and rapid speciation for many of for many studies of adaptation and speciation. Here, we review the the classic examples of adaptive radiation have been established advantages of adaptive radiations, especially recent ones, for by using molecular techniques [e.g., cichlids (4), Galapagos detecting evolutionary trends and the genetic dissection of adap- finches (5, 6), and Hawaiian silverswords (7)]. Ecological and tive traits. We focus on Aquilegia as a primary example of these manipulative experiments are used to identify and test pheno- advantages and highlight progress in understanding the genetic type–environmental correlations and trait utility. Ultimately, basis of flower color. Phylogenetic analysis of Aquilegia indicates such studies have pointed to the link between divergent natural that flower color transitions proceed by changes in the types of selection and reproductive isolation and, thus, speciation (3). anthocyanin pigments produced or their complete loss. Biochem- Studies of adaptive radiations have exploded during the last 20 ical, crossing, and gene expression studies have provided a wealth years. In a search of the ISI Web of Science with ‘‘adaptive of information about the genetic basis of these transitions in radiation’’ (limited to the subject area of evolutionary biology) Aquilegia. To obtain both enzymatic and regulatory candidate we found 80 articles published in 2008 compared with only 1 in genes for the entire flavonoid pathway, which produces antho- 1990.
    [Show full text]
  • Grape Seeds Proanthocyanidins: Advanced Technological Preparation and Analytical Characterization
    antioxidants Article Grape Seeds Proanthocyanidins: Advanced Technological Preparation and Analytical Characterization Paolo Morazzoni 1, Paola Vanzani 2, Sandro Santinello 1, Antonina Gucciardi 2,3 , Lucio Zennaro 2, Giovanni Miotto 2,3,4,* and Fulvio Ursini 2,* 1 Distillerie Bonollo Umberto S.p.A., Nutraceutical Division, Mestrino, 35035 Padova, Italy; [email protected] (P.M.); [email protected] (S.S.) 2 Department of Molecular Medicine, University of Padova, 35129 Padova, Italy; [email protected] (P.V.); [email protected] (A.G.); [email protected] (L.Z.) 3 Proteomics Center, University of Padova and Azienda Ospedaliera di Padova, 35129 Padova, Italy 4 CRIBI Biotechnology Center, University of Padova, 35129 Padova, Italy * Correspondence: [email protected] (G.M.); [email protected] (F.U.); Tel.: +39-0498276130 (G.M.); +39-0498276104 (F.U.) Abstract: A “green” solvent-free industrial process (patent pending) is here described for a grape seed extract (GSE) preparation (Ecovitis™) obtained from selected seeds of Veneto region wineries, in the northeast of Italy, by water and selective tangential flow filtration at different porosity. Since a comprehensive, non-ambiguous characterization of GSE is still a difficult task, we resorted to using an integrated combination of gel permeation chromatography (GPC) and electrospray ionization high resolution mass spectrometry (ESI-HRMS). By calibration of retention time and spectroscopic quantification of catechin as chromophore, we succeeded in quantifying GPC polymers up to traces at Citation: Morazzoni, P.; Vanzani, P.; n = 30. The MS analysis carried out by the ESI-HRMS method by direct-infusion allows the detection Santinello, S.; Gucciardi, A.; Zennaro, of more than 70 species, at different polymerization and galloylation, up to n = 13.
    [Show full text]
  • Specialty Sorghums for Gluten Free Foods
    SPECIALTY SORGHUMS FOR HEALTHY FOODS Dr. LLOYD W. ROONEY, Professor and Faculty Fellow Dr. JOSEPH M. AWIKA, Research Associate Cereal Quality Lab, Soil & Crop Sciences Dept. Texas A&M University 2474 TAMUS College Station, Texas 77843-2474 1 I. INTRODUCTION Sorghum is a major crop used for food, feed and industrial purposes worldwide. In the Western Hemisphere it is mainly used as a livestock feed and has not been considered a significant ingredient in foods. With over 40,000 accessions in the world collection, tremendous diversity exists in sorghum in both composition and processing properties. The kernel varies in size, shape, color, density, hardness, composition, processing properties, taste and texture and nutritional value. This chapter reviews information on new food sorghums and other special sorghums with unique properties that could be used in producing a wide variety of food products for specialty markets and health foods. The paper will emphasize white food sorghum hybrids and special tannin and black sorghums with high levels of phytochemicals. These special sorghum varieties are an excellent source of nutraceuticals that can compete effectively with fruits and vegetable sources. In addition, we will indicate other opportunities for producing healthy foods from sorghum. A. Sorghum production Sorghum is the fifth most important cereal crop grown in the world. It is a major food grain in Africa and parts of India and China. In 2003, 42.1 million hectares of sorghum were harvested worldwide, with a total production of 54.7 million metric tons. United States, India, and Nigeria are the largest producers of sorghum representing approximately 19.2%, 14.5%, and 14.5% of the total world production, respectively, in 2003.
    [Show full text]
  • 1 1 2 Trends in Lc-Ms and Lc-Hrms Analysis And
    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Diposit Digital de la Universitat de Barcelona 1 2 3 TRENDS IN LC-MS AND LC-HRMS ANALYSIS AND CHARACTERIZATION OF 4 POLYPHENOLS IN FOOD. 5 6 Paolo Lucci1, Javier Saurina 2,3 and Oscar Núñez 2,3,4 * 7 8 9 1Department of Food Science, University of Udine, via Sondrio 2/a, 33100 Udine, Italy 10 2Department of Analytical Chemistry, University of Barcelona. Martí i Franquès, 1-11, 11 E-08028 Barcelona, Spain. 12 3 Research Institute in Food Nutrition and Food Safety, University of Barcelona, Recinte Torribera, 13 Av. Prat de la Riba 171, Edifici de Recerca (Gaudí), E-08921 Santa Coloma de Gramenet, 14 Barcelona, Spain. 15 4 Serra Húnter Fellow, Generalitat de Catalunya, Spain. 16 17 18 19 20 * Corresponding author: Oscar Núñez 21 Department of Analytical Chemistry, University of Barcelona. 22 Martí i Franquès, 1-11, E-08028 Barcelona, Spain. 23 Phone: 34-93-403-3706 24 Fax: 34-93-402-1233 25 e-mail: [email protected] 26 27 28 29 30 31 1 32 33 34 35 Contents 36 37 Abstract 38 1. Introduction 39 2. Types of polyphenols in foods 40 2.1. Phenolic acids 41 2.2. Flavonoids 42 2.3. Lignans 43 2.4. Stilbenes 44 3. Sample treatment procedures 45 4. Liquid chromatography-mass spectrometry 46 5. High resolution mass spectrometry 47 5.1. Orbitrap mass analyzer 48 5.2. Time-of-flight (TOF) mass analyzer 49 6. Chemometrics 50 6.1.
    [Show full text]
  • Functional Analysis of Ghchs, Ghanr And
    Gao et al. BMC Plant Biology (2019) 19:455 https://doi.org/10.1186/s12870-019-2065-7 RESEARCH ARTICLE Open Access Functional analysis of GhCHS, GhANR and GhLAR in colored fiber formation of Gossypium hirsutum L Jianfang Gao1†, Li Shen1†, Jingli Yuan1, Hongli Zheng1, Quansheng Su1, Weiguang Yang1, Liqing Zhang1, Vitalis Ekene Nnaemeka1, Jie Sun2, Liping Ke1* and Yuqiang Sun1* Abstract Background: The formation of natural colored fibers mainly results from the accumulation of different anthocyanidins and their derivatives in the fibers of Gossypium hirsutum L. Chalcone synthase (CHS) is the first committed enzyme of flavonoid biosynthesis, and anthocyanidins are transported into fiber cells after biosynthesis mainly by Anthocyanidin reductase (ANR) and Leucoanthocyanidin reductase (LAR) to present diverse colors with distinct stability. The biochemical and molecular mechanism of pigment formation in natural colored cotton fiber is not clear. Results: The three key genes of GhCHS, GhANR and GhLAR were predominantly expressed in the developing fibers of colored cotton. In the GhCHSi, GhANRi and GhLARi transgenic cottons, the expression levels of GhCHS, GhANR and GhLAR significantly decreased in the developing cotton fiber, negatively correlated with the content of anthocyanidins and the color depth of cotton fiber. In colored cotton Zongxu1 (ZX1) and the GhCHSi, GhANRi and GhLARi transgenic lines of ZX1, HZ and ZH, the anthocyanidin contents of the leaves, cotton kernels, the mixture of fiber and seedcoat were all changed and positively correlated with the fiber color. Conclusion: The three genes of GhCHS, GhANR and GhLAR were predominantly expressed early in developing colored cotton fibers and identified to be a key genes of cotton fiber color formation.
    [Show full text]
  • Anthocyanins, Vibrant Color Pigments, and Their Role in Skin Cancer Prevention
    biomedicines Review Anthocyanins, Vibrant Color Pigments, and Their Role in Skin Cancer Prevention 1,2, , 2,3, 4,5 3 Zorit, a Diaconeasa * y , Ioana S, tirbu y, Jianbo Xiao , Nicolae Leopold , Zayde Ayvaz 6 , Corina Danciu 7, Huseyin Ayvaz 8 , Andreea Stanilˇ aˇ 1,2,Madˇ alinaˇ Nistor 1,2 and Carmen Socaciu 1,2 1 Faculty of Food Science and Technology, University of Agricultural Sciences and Veterinary Medicine, 400372 Cluj-Napoca, Romania; [email protected] (A.S.); [email protected] (M.N.); [email protected] (C.S.) 2 Institute of Life Sciences, University of Agricultural Sciences and Veterinary Medicine, Calea Mănă¸stur3-5, 400372 Cluj-Napoca, Romania; [email protected] 3 Faculty of Physics, Babes, -Bolyai University, Kogalniceanu 1, 400084 Cluj-Napoca, Romania; [email protected] 4 Institute of Chinese Medical Sciences, State Key Laboratory of Quality Research in Chinese Medicine, University of Macau, Taipa, Macau 999078, China; [email protected] 5 International Research Center for Food Nutrition and Safety, Jiangsu University, Zhenjiang 212013, China 6 Faculty of Marine Science and Technology, Department of Marine Technology Engineering, Canakkale Onsekiz Mart University, 17100 Canakkale, Turkey; [email protected] 7 Victor Babes University of Medicine and Pharmacy, Department of Pharmacognosy, 2 Eftimie Murgu Sq., 300041 Timisoara, Romania; [email protected] 8 Department of Food Engineering, Engineering Faculty, Canakkale Onsekiz Mart University, 17020 Canakkale, Turkey; [email protected] * Correspondence: [email protected]; Tel.: +40-751-033-871 These authors contributed equally to this work. y Received: 31 July 2020; Accepted: 25 August 2020; Published: 9 September 2020 Abstract: Until today, numerous studies evaluated the topic of anthocyanins and various types of cancer, regarding the anthocyanins’ preventative and inhibitory effects, underlying molecular mechanisms, and such.
    [Show full text]
  • Anti-Inflammatory Activity of Sambucus Plant Bioactive
    Natural Product Sciences 25(3) : 215-221 (2019) https://doi.org/10.20307/nps.2019.25.3.215 Anti-inflammatory Activity of Sambucus Plant Bioactive Compounds against TNF-α and TRAIL as Solution to Overcome Inflammation Associated Diseases: The Insight from Bioinformatics Study Wira Eka Putra1, Wa Ode Salma2, Muhaimin Rifa'i3,* 1Department of Biology, Faculty of Mathematics and Natural Sciences, Universitas Negeri Malang, Indonesia 2Department of Nutrition, Faculty of Medicine, Halu Oleo University, Indonesia 3Department of Biology, Faculty of Mathematics and Natural Sciences, Brawijaya University, Indonesia Abstract − Inflammation is the crucial biological process of immune system which acts as body’s defense and protective response against the injuries or infection. However, the systemic inflammation devotes the adverse effects such as multiple inflammation associated diseases. One of the best ways to treat this entity is by blocking the tumor necrosis factor alpha (TNF-α) and TNF-related apoptosis-inducing ligand (TRAIL) to avoid the pro- inflammation cytokines production. Thus, this study aims to evaluate the potency of Sambucus bioactive compounds as anti-inflammation through in silico approach. In order to assess that, molecular docking was performed to evaluate the interaction properties between the TNF-α or TRAIL with the ligands. The 2D structure of ligands were retrieved online via PubChem and the 3D protein modeling was done by using SWISS Model. The prediction results of the study showed that caffeic acid (-6.4 kcal/mol) and homovanillic acid (-6.6 kcal/mol) have the greatest binding affinity against the TNF-α and TRAIL respectively. This evidence suggests that caffeic acid and homovanillic acid may potent as anti-inflammatory agent against the inflammation associated diseases.
    [Show full text]
  • Phenolic Compounds in Cereal Grains and Their Health Benefits
    and antioxidant activity are reported in the Phenolic Compounds in Cereal literature. Unfortunately, it is difficult to make comparisons of phenol and anti- Grains and Their Health Benefits oxidant activity levels in cereals since different methods have been used. The ➤ Whole grain cereals are a good source of phenolics. purpose of this article is to give an overview ➤ Black sorghums contain high levels of the unique 3-deoxyanthocyanidins. of phenolic compounds reported in whole ➤ Oats are the only source of avenanthramides. grain cereals and to compare their phenol and antioxidant activity levels. ➤ Among cereal grains, tannin sorghum and black rice contain the highest antioxidant activity in vitro. Phenolic Acids Phenolic acids are derivatives of benzoic and cinnamic acids (Fig. 1) and are present in all cereals (Table I). There are two Most of the literature on plant phenolics classes of phenolic acids: hydroxybenzoic L. DYKES AND L. W. ROONEY focuses mainly on those in fruits, acids and hydroxycinnamic acids. Hy- TEXAS A&M UNIVERSITY vegetables, wines, and teas (33,50,53,58, droxybenzoic acids include gallic, p- College Station, TX 74). However, many phenolic compounds hydroxybenzoic, vanillic, syringic, and in fruits and vegetables (i.e., phenolic acids protocatechuic acids. The hydroxycinna- esearch has shown that whole grain and flavonoids) are also reported in cereals. mic acids have a C6-C3 structure and Rconsumption helps lower the risk of The different species of grains have a great include coumaric, caffeic, ferulic, and cardiovascular disease, ischemic stroke, deal of diversity in their germplasm sinapic acids. The phenolic acids reported type II diabetes, metabolic syndrome, and resources, which can be exploited.
    [Show full text]
  • Trimer Procyanidin Oligomers Contribute to the Protective Effects of Cinnamon Extracts on Pancreatic Β-Cells in Vitro
    Acta Pharmacologica Sinica (2016) 37: 1083–1090 © 2016 CPS and SIMM All rights reserved 1671-4083/16 www.nature.com/aps Original Article Trimer procyanidin oligomers contribute to the protective effects of cinnamon extracts on pancreatic β-cells in vitro Peng SUN1, 2, #, Ting WANG1, #, Lu CHEN2, #, Bang-wei YU1, Qi JIA2, Kai-xian CHEN1, 2, Hui-min FAN3, Yi-ming LI2, *, He-yao WANG1, * 1Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; 2School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203, China; 3Department of Cardiovascular and Thoracic Surgery, Shanghai Heart Failure Research Center, Shanghai East Hospital, Tongji University School of Medicine, Shanghai 200123, China Aim: Cinnamon extracts rich in procyanidin oligomers have shown to improve pancreatic β-cell function in diabetic db/db mice. The aim of this study was to identify the active compounds in extracts from two species of cinnamon responsible for the pancreatic β-cell protection in vitro. Methods: Cinnamon extracts were prepared from Cinnamomum tamala (CT-E) and Cinnamomum cassia (CC-E). Six compounds procyanidin B2 (cpd1), (–)-epicatechin (cpd2), cinnamtannin B1 (cpd3), procyanidin C1 (cpd4), parameritannin A1 (cpd5) and cinnamtannin D1 (cpd6) were isolated from the extracts. INS-1 pancreatic β-cells were exposed to palmitic acid (PA) or H2O2 to induce lipotoxicity and oxidative stress. Cell viability and apoptosis as well as ROS levels were assessed. Glucose-stimulated insulin secretion was examined in PA-treated β-cells and murine islets. Results: CT-E, CC-E as well as the compounds, except cpd5, did not cause cytotoxicity in the β-cells up to the maximum dosage using in this experiment.
    [Show full text]
  • Naturally Occurring Anthocyanin, Structure, Functions And
    iochemis t B try n & la P P h f y o s l i Journal of o a l n o r g Pervaiz et al., J Plant Biochem Physiol 2017, 5:2 u y o J DOI: 10.4172/2329-9029.1000187 ISSN: 2329-9029 Plant Biochemistry & Physiology Review Article Open Access Naturally Occurring Anthocyanin, Structure, Functions and Biosynthetic Pathway in Fruit Plants Tariq Pervaiz1,2, Jiu Songtao1, Faezeh Faghihi3, Muhammad Salman Haider1 and Jinggui Fang1* 1Key Laboratory of Genetics and Fruit Development, College of Horticulture, Nanjing Agricultural University, Nanjing 210095, PR China 2Department of Agriculture and Food Technology, Karakoram International University Gilgit, Pakistan 3Cellular and Molecular Research Center, Iran University of Medical Sciences, Tehran, Iran *Corresponding author: Jinggui Fang, Key Laboratory of Genetics and Fruit Development, College of Horticulture, Nanjing Agricultural University, Nanjing, PR China, E-mail: [email protected] Received Date: April 25, 2017; Accepted Date: April 29, 2017; Published Date: May 06, 2017 Copyright: © 2017 Pervaiz T, et al. This is an open-access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited. Abstract Anthocyanins are naturally occurring compounds, member of the flavonoid groups of photochemical, involved in defense against the damaging effects of UV irradiation in plants and protect from many oxidants. The anthocyanins, group of pigments are relatively small and diverse flavonoid family in nature, and responsible for the attractive colors, red and purple to blue in many plants. Presence of pigments in flowers and fruits seems to provide attraction for pollination and aiding seed distribution, it also provides antiviral and antimicrobial activities, however their occurrence in the vacuoles remains ambiguous.
    [Show full text]
  • PROSPECÇÃO DE GENES TECIDO ESPECÍFICO E METABÓLITOS EM Elaeis Spp
    LUIZ HENRIQUE GALLI VARGAS PROSPECÇÃO DE GENES TECIDO ESPECÍFICO E METABÓLITOS EM Elaeis spp. LAVRAS - MG 2014 LUIZ HENRIQUE GALLI VARGAS PROSPECÇÃO DE GENES TECIDO ESPECÍFICO E METABÓLITOS EM Elaeis spp. Dissertação apresentada à Universidade Federal de Lavras, como parte das exigências do Programa de Pós- Graduação em Biotecnologia Vegetal, área de concentração em Biotecnologia Vegetal, para a obtenção do título de Mestre. Orientador Dr. Manoel Teixeira Souza Júnior Coorientadores Dr. Eduardo Fernandes Formighieri Dra. Patrícia Verardi Abdelnur LAVRAS – MG 2014 Ficha Catalográfica Elaborada pela Coordenadoria de Produtos e Serviços da Biblioteca Universitária da UFLA Vargas, Luiz Henrique Galli. Prospecção de genes tecido específico e metabólitos em Elaeis spp. / Luiz Henrique Galli Vargas. – Lavras : UFLA, 2014. 138 p. : il. Dissertação (mestrado) – Universidade Federal de Lavras, 2014. Orientador: Manoel Teixeira Souza Júnior. Bibliografia. 1. Genoma. 2. Palma de óleo. 3. Caiaué. 4. UHPLC-MS. 5. Expressão relativa. I. Universidade Federal de Lavras. II. Título. CDD – 633.851233 LUIZ HENRIQUE GALLI VARGAS PROSPECÇÃO DE GENES TECIDO ESPECÍFICO E METABÓLITOS EM Elaeis spp. Dissertação apresentada à Universidade Federal de Lavras, como parte das exigências do Programa de Pós- Graduação em Biotecnologia Vegetal, área de concentração em Biotecnologia Vegetal, para a obtenção do título de Mestre. APROVADO em 15 de agosto de 2014. Dr. Eduardo Fernandes Formighieri EMBRAPA - Agroenergia Dra. Patrícia Verardi Abdelnur EMBRAPA - Agroenergia Dr. João Ricardo Moreira de Almeida EMBRAPA - Agroenergia Dr. Alexandre Alonso Alves EMBRAPA - Agroenergia Dr. Manoel Teixeira Souza Júnior Orientador LAVRAS – MG 2014 Aos meus pais, irmãos e toda família. Aos meus avós (in memoriam). DEDICO AGRADECIMENTOS Aos meus pais, Luiz Sérgio Oliveira Vargas e Neli Galli, por permitirem a realização deste sonho, à minha “mãe” de coração, Magna Viana pelos incentivos durante os anos.
    [Show full text]
  • Datasheet Inhibitors / Agonists / Screening Libraries a DRUG SCREENING EXPERT
    Datasheet Inhibitors / Agonists / Screening Libraries A DRUG SCREENING EXPERT Product Name : Procyanidin B4 Catalog Number : TN1151 CAS Number : 29106-51-2 Molecular Formula : C30H26O12 Molecular Weight : 578.52 Description: Procyanidin B4 reveals significant antioxidant activity Storage: 2 years -80°C in solvent; 3 years -20°C powder; Receptor (IC50) Nrf2 In vitro Activity Aimed to isolate and purify the proanthocyanidins from lotus seed skin by acetone extraction and rotary evaporation, identify their chemical structures by HPLC-MS-MS and NMR, and further investigate the antioxidant properties of the extract purified by macroporous resin (PMR) from lotus seed skin both in vitro and in vivo. The results showed that PMR mainly contained oligomeric proanthocyanidins, especially dimeric procyanidin B1 (PB1), procyanidin B2 and Procyanidin B4. Although it had limited ability to directly scavenge radicals in vitro, PMR could significantly enhance the expressions of antioxidant proteins via activation of nuclear factor-E2-related factor 2 (Nrf2)-antioxidant response element (ARE) pathway in HepG2 cells. Molecular data revealed that PB1, a major component in PMR, stabilized Nrf2 by inhibiting the ubiquitination of Nrf2, which led to subsequent activation of the Nrf2-ARE pathway, including the enhancements of Nrf2 nuclear translocation, Nrf2-ARE binding and ARE transcriptional activity. Moreover, the in vivo results in high fat diet-induced mice further verified the powerful antioxidant property of PMR[1] Reference 1. Lotus seed skin proanthocyanidin extract exhibits potent antioxidant property via activation of the Nrf2-ARE pathway.Acta Biochim Biophys Sin (Shanghai). 2019 Jan 1;51(1):31-40. 2. Comparison of compounds of three Rubus species and their antioxidant activity.Drug Discov Ther.
    [Show full text]