DOCSLIB.ORG

Review Article Recent Applications of Mass Spectrometry in the Study of Grape and Wine Polyphenols

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Review Article Recent Applications of Mass Spectrometry in the Study of Grape and Wine Polyphenols Hindawi Publishing Corporation ISRN Spectroscopy Volume 2013, Article ID 813563, 45 pages http://dx.doi.org/10.1155/2013/813563 Review Article Recent Applications of Mass Spectrometry in the Study of Grape and Wine Polyphenols Riccardo Flamini Consiglio per la Ricerca e la Sperimentazione in Agricoltura-Centro di Ricerca per la Viticoltura (CRA-VIT), Viale XXVIII Aprile 26, 31015 Conegliano, Italy Correspondence should be addressed to Riccardo Flamini; riccardo.�amini�entecra.it Received 24 September 2012; Accepted 12 October 2012 Academic �ditors: D.-A. Guo, �. Sta�lov, and M. Valko Copyright © 2013 Riccardo Flamini. is is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Polyphenols are the principal compounds associated with health bene�c effects of wine consumption and in general are characterized by antioxidant activities. Mass spectrometry is shown to play a very important role in the research of polyphenols in grape and wine and for the quality control of products. e so ionization of LC/MS makes these techniques suitable to study the structures of polyphenols and anthocyanins in grape extracts and to characterize polyphenolic derivatives formed in wines and correlated to the sensorial characteristics of the product. e coupling of the several MS techniques presented here is shown to be highly effective in structural characterization of the large number of low and high molecular weight polyphenols in grape and wine and also can be highly effective in the study of grape metabolomics. 1. Principal Polyphenols of Grape and Wine During winemaking the condensed (or nonhydrolyzable) tannins are transferred to the wine and contribute strongly to Polyphenols are the principal compounds associated to the sensorial characteristic of the product. In the mouth, the health bene�c effects of wine consumption. A French epi- formation of complexes between tannins and saliva proteins demiological study performed in the end of 1970s reported confers to the wine the sensorial characteristic of astringency: that in France, despite the high consumption of foods rich bitterness and astringency of wine is linked to tannins struc- in saturated fatty acids, the incidence of mortality from ture, in particular galloylation degree (DG) and polymeriza- cardiovascular diseases was lower than that in other com- tion degree (DP) of �avan-3-ols [2, 3]. Grape tannins are used parable countries. is phenomenon was called “the French as active ingredients in medicinal products characterized paradox� and was related to the bene�cial effects of red wine by antioxidant plasma activity and for the treatment of consumption [1]. In general; polyphenols have antioxidant circulatory disorders (capillary fragility, microangiopathy of activities. eir activity as peroxyl radical scavengers and the retina, reducing of platelet aggregation, decreasing of the in the formation of complexes with metals (Cu, Fe, etc.) susceptibility of healthy cells towards toxic and carcinogenic has been shown by in vitro studies. Moreover, the ability of agents, and antioxidant activity toward human low density polyphenols to cross the intestinal wall of mammals confers lipoprotein) (see [4], and references cited herein). their biological properties. Flavonols are another important class of grape polyphe- Flavan-3-ols are one of the principal classes of grape nols. ese compounds are mainly present in the skin of polyphenols which include (+)-catechin and ( )-epicatechin, berry; the principal are quercetin, kaempferol, and myri- and their oligomers called procyanidins, proanthocyanidins, cetin present in glycoside forms such as glucoside, glu- and prodelphinidins. B-type and A-type procyanidins− and curonide, and rutin. Recently, also isorhamnetin, laricitrin, proanthocyanidins (the latter are condensed tannins) are and syringetin were identi�ed in grape [5, 6]. e structures present in the grape skin and seeds; tannins are mainly of �avonols are reported in Figure 2(b). e main biological present in seeds, and prodelphinidins are polymeric tannins activity of quercetin is to block human platelets aggregation, composed of gallocatechin units (structures in Figure 1). and it seems that it inhibits carcinogens and the cancer 2 ISRN Spectroscopy OH OH OH OH HO O H HO O H R1 OH R2 OH OH H OH OH H OH ((+) catechin) R1 = R2 = - HO O OH H (( ) epicatechin) R1 = OH R2 = − - H OH O CO OH H OH OH R2 = H R1 = O CO OH Dimer B2 gallate OH OH OH OH HO O OH H OH R1 HO O R2 OH OH O HO O OH H OH R3 R4 O OH OH HO B-type dimer HO OH R1 = OH R2 = H R3 = H R4 = OH A-type dimer OH H OH H = R1 = R2 = R3 = R4 = R1 = H R2 = OH R3 = H R4 = OH R1 = H R2 = OH R3 = OH R4 = H OH OH HO O OH H OH R1 R2 HO OH O H HO OH OH H OH OH OH HO O R3 O H R4 OH H H OH OH HO OH OH OH H OH H R1 = R2 = R3 = R4 = HO O R1 = H R2 = OH R3 = H R4 = OH H = H R1 = OH R2 = H R3 = H R4 = OH R1 = H R2 = OH R3 = OH R4 = H OH OH Trimer F 1: ��type ��� ��type ��������o� ���ers ��� tr��ers prese�t �� t�e �r�pe see�s� ISRN Spectroscopy 3 R1 OH R1 OH HO O+ R2 HO O OH O R2 OR 3 O OH OR OH OH O OR4 Pelargonidin R1 = H; R2 = H R = glucose; glucuronic acid Cyanidin R1 = H; R2 = OH Kaempferol R1 = H; R2 = H Delphinidin R1 = OH; R2 = OH Quercetin R1 = OH; R2 = H Peonidin R1 = OCH3; R2 = H Myricetin R1 = OH; R2 = OH Malvidin R1 = OCH3; R2 = OCH3 Isorhamnetin R1 = H; R2 = OCH3 Petunidin R1 = OCH3; R2 = OH Laricitrin R1 = OH; R2 = OCH3 H, glucose R3 = Syringetin R1 = OCH3;R2 = OCH3 3 ) BDFUZM ८IZESPYZDJOOBNZM DJT USBOT DBČFPZM (a) (b) F 2: (a) e principal monomer anthocyanins of grape: the glucose residue can be linked to an acetyl, coumaroyl, or caffeoyl group. (b) e principal �avonols of grape. cell growth in human tumors (see [4] and references cited e anthocyanin pro�le is also determined for the study herein). of grape chemotaxonomy; for example, the presence of 3,5- Stilbene compounds are the principal phytoalexins of O-diglucoside anthocyanins is used to distinguish between grape: they include cis- and trans-resveratrol (3,5,4 -trihy- V. vinifera and hybrid grape varieties, the former being droxystilbene) and their glucoside derivatives (cis- and trans- characterized by low presence or practical absence of these ′ compounds. Moreover, grape anthocyanins are antioxidant piceid), piceatannol (3,4,3 ,5 -tetrahydroxy-trans-stilbene), and natural colorants used in the nutraceutical, food, and and stilbene oligomers (viniferins).′ ′ A number of studies pharmaceutical industries [26–28]. evidenced anticancer, cardioprotection, anti-in�ammatory During the wine aging, anthocyanins are undergone and antioxidant activities, and platelet aggregation inhibition reactions with other matrix compounds, and new molecules of trans-resveratrol [7–13]. Grapevine synthesizes viniferins with different chromatic characteristics, with respect to in different parts of the plant (roots, clusters, and stems) their precursors, are formed [29]. As a consequence, the in particular -viniferin, two -viniferin glucosides, and anthocyanic pro�le of wine changes dramatically during pallidol [14, 15]. Moreover, viniferins can arise from the aging; for example, the LC-chromatogram of a 4-month aged oligomerisation of trans-resveratrol in grape tissues as active wine recorded at 520 nm shows as main signals the grape defense of the plant against exogenous attacks or could be anthocyanins, and aer 2-year aging, these signals disappear produced from resveratrol by extracellular enzymes released completely, and a broad peak due to the new anthocyanin from the pathogen in an attempt to eliminate undesirable derivatives overlaps the latter part of the chromatogram toxic compounds [16, 17]. Structures of the principal vine [30, 31]. Reaction of anthocyanins with �avan-3-ols, pro- viniferins are showed in Figure 3. cyanidins, and tannins shis the wine from purple-red to Anthocyanins are the compounds responsible for the brick-red hue, and the formation of pyranoanthocyanins, red color of grapes and wines. Principal anthocyanins of stable structures formed by reaction between anthocyanins Vitis vinifera varieties are delphinidin (Dp), cyanidin (Cy), and acetaldehyde, pyruvic acid, vinylphenol, vinylcatechol, petunidin (Pt), peonidin (Pn), and malvidin (Mv), present in vinylguaiacol, or vinyl(epi)catechin, toward orange hue [20, the skins as 3-O-monoglucoside, 3-O-acetylmonoglucoside, 21, 32–35]. and 3-O-(6-O-p-coumaroyl)monoglucoside. Oen, also Mv- More than hundred structures belonging the pigment 3-O-(6-O-caffeoyl)monoglucoside is present. More recently, families of anthocyanins, pyranoanthocyanins, direct �ava- pelargonidin (Pg) 3-O-monoglucoside was found in grape nol-anthocyanin condensation products and acetaldehyde- [24]. Oen the not V. vinifera (hybrid) red grapes also contain mediated �avanol-anthocyanin condensation products diglucoside anthocyanins with the second glucose molecule (anthocyanin linked to �avan-3-ol either directly or by ethyl linked to the C-5 hydroxyl group (structures showed in bridge), were identi�ed in red wines. Structures of principal Figure 2(a)). anthocyanin-derivatives are showed in Figure 4,[30]. 4 ISRN Spectroscopy OH HO HO OH HO OH OH OH OH HO HO HO H H H H H H O O O OH OH OH OH HO OH 2 3 4 1 OH HO HO HO HO OH H HO H HO OH OH H H H H H O HO HO H OH OH OH OH HO 5 6 7 OH OH OH HO HO OH HO H O OH OH H H O HO H H O H H H H HO H HO H OH H O OH HO HO HO O 8 OH OH 10 9 OH HO HO O OH O H OH HO H H H HO H H H OH H OH O OH OH O HO OH HO 11 12 OH HO HO HO HO OH OH O HO O H H H HO H H H H HO OH H H OH H H H H H H H O OH HO HO O OH OH OH HO OH 14 13 F 3: Continued.
Load more

Recommended publications
  • Dissertation
    Dissertation Charakterisierung von oligomeren Kakao- Proanthocyanidinen: Extraktion und chromatographische Trennung mit simultaner Bestimmung der antioxidativen Kapazität Vasilisa Pedan 2017 Charakterisierung von oligomeren Kakao-Proanthocyanidinen: Extraktion und chromatographische Trennung mit simultaner Bestimmung der antioxidativen Kapazität Dissertation zur Erlangung des naturwissenschaftlichen Doktorgrades (Dr. rer. nat.) des Fachbereichs Chemie, Fakultät für Mathematik, Informatik und Naturwissenschaften der Universität Hamburg vorgelegt von Dipl. LMChem Vasilisa Pedan Hamburg März 2017 Die vorliegende Arbeit wurde in der Zeit von November 2012 bis März 2017 unter der Leitung von Herrn Prof. Dr. Sascha Rohn, Institut für Lebensmittelchemie der Universität Hamburg, angefertigt. Die praktischen Arbeiten erfolgten an der Zürcher Hochschule für Angewandte Wissenschaften in Wädenswil in der Schweiz unter der Betreuung von Herrn Dr. Norbert Fischer. Tag der Disputation: 30.10.2017 1. Gutachter der Dissertation: Prof. Dr. Sascha Rohn 2. Gutachter der Dissertation: Prof. Dr. Bernward Bisping Kein zweites Mal hat die Natur solche Fülle der wertvollsten Nährstoffe auf einem so kleinen Raum zusammengedrängt wie gerade bei der Kakaobohne. Alexander von Humboldt Veröffentlichungen Publikationen Pedan V, Weber, C, Do T, Fischer N, Reich E, Rohn S (2017) HPTLC fingerprint profile analysis of cocoa proanthocyanidins depending on origin and genotype. Food Chemistry. In press Pedan V, Fischer N, Bernath K, Hühn T, Rohn S (2017) Determination of oligomeric proanthocyanidins and their antioxidant activity from different chocolate manufacturing stages using the NP-HPLC-online-DPPH methodology. Food Chemistry, 214, 523-532. Pedan V, Fischer N, & Rohn S (2016) Extraction of cocoa proanthocyanidins and their fractionation by sequential centrifugal partition chromatography and gel permeation chromatography. Analytical and Bioanalytical Chemistry, 408, 5905-5914.
    [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]
  • Chemical Composition of Red Wines Made from Hybrid Grape and Common Grape (Vitis Vinifera L.) Cultivars
    444 Proceedings of the Estonian Academy of Sciences, 2014, 63, 4, 444–453 Proceedings of the Estonian Academy of Sciences, 2014, 63, 4, 444–453 doi: 10.3176/proc.2014.4.10 Available online at www.eap.ee/proceedings Chemical composition of red wines made from hybrid grape and common grape (Vitis vinifera L.) cultivars Priit Pedastsaara*, Merike Vaherb, Kati Helmjab, Maria Kulpb, Mihkel Kaljurandb, Kadri Karpc, Ain Raald, Vaios Karathanose, and Tõnu Püssaa a Department of Food Hygiene, Estonian University of Life Sciences, Kreutzwaldi 58A, 51014 Tartu, Estonia b Department of Chemistry, Tallinn University of Technology, Akadeemia tee 15, 12618 Tallinn, Estonia c Department of Horticulture, Estonian University of Life Sciences, Kreutzwaldi 1, 51014 Tartu, Estonia d Department of Pharmacy, University of Tartu, Nooruse 1, 50411 Tartu, Estonia e Department of Dietetics and Nutrition, Harokopio University, 70 El. Venizelou Ave., Athens, Greece Received 21 June 2013, revised 8 May 2014, accepted 23 May 2014, available online 20 November 2014 Abstract. Since the formulation of the “French paradox”, red grape wines are generally considered to be health-promoting products rather than culpable alcoholic beverages. The total wine production, totalling an equivalent of 30 billion 750 mL bottles in 2009, only verifies the fact that global demand is increasing and that the polyphenols present in wines are accounting for a significant proportion of the daily antioxidant intake of the general population. Both statements justify the interest of new regions to be self-sufficient in the wine production. Novel cold tolerant hybrid grape varieties also make it possible to produce wines in regions where winter temperatures fall below – 30 °C and the yearly sum of active temperatures does not exceed 1750 °C.
    [Show full text]
  • (12) United States Patent (10) Patent No.: US 8,026,285 B2 Bezwada (45) Date of Patent: Sep
    US008O26285B2 (12) United States Patent (10) Patent No.: US 8,026,285 B2 BeZWada (45) Date of Patent: Sep. 27, 2011 (54) CONTROL RELEASE OF BIOLOGICALLY 6,955,827 B2 10/2005 Barabolak ACTIVE COMPOUNDS FROM 2002/0028229 A1 3/2002 Lezdey 2002fO169275 A1 11/2002 Matsuda MULT-ARMED OLGOMERS 2003/O158598 A1 8, 2003 Ashton et al. 2003/0216307 A1 11/2003 Kohn (75) Inventor: Rao S. Bezwada, Hillsborough, NJ (US) 2003/0232091 A1 12/2003 Shefer 2004/0096476 A1 5, 2004 Uhrich (73) Assignee: Bezwada Biomedical, LLC, 2004/01 17007 A1 6/2004 Whitbourne 2004/O185250 A1 9, 2004 John Hillsborough, NJ (US) 2005/0048121 A1 3, 2005 East 2005/OO74493 A1 4/2005 Mehta (*) Notice: Subject to any disclaimer, the term of this 2005/OO953OO A1 5/2005 Wynn patent is extended or adjusted under 35 2005, 0112171 A1 5/2005 Tang U.S.C. 154(b) by 423 days. 2005/O152958 A1 7/2005 Cordes 2005/0238689 A1 10/2005 Carpenter 2006, OO13851 A1 1/2006 Giroux (21) Appl. No.: 12/203,761 2006/0091034 A1 5, 2006 Scalzo 2006/0172983 A1 8, 2006 Bezwada (22) Filed: Sep. 3, 2008 2006,0188547 A1 8, 2006 Bezwada 2007,025 1831 A1 11/2007 Kaczur (65) Prior Publication Data FOREIGN PATENT DOCUMENTS US 2009/0076174 A1 Mar. 19, 2009 EP OO99.177 1, 1984 EP 146.0089 9, 2004 Related U.S. Application Data WO WO9638528 12/1996 WO WO 2004/008101 1, 2004 (60) Provisional application No. 60/969,787, filed on Sep. WO WO 2006/052790 5, 2006 4, 2007.
    [Show full text]
  • Characterization of Cell Wall Degrading Enzymes from Chrysosporium Lucknowense C1 and Their Use to Degrade Sugar Beet Pulp
    Characterization of cell wall degrading enzymes from Chrysosporium lucknowense C1 and their use to degrade sugar beet pulp Stefan Kühnel Thesis committee Thesis supervisor Prof. dr. ir. H. Gruppen Professor of Food Chemistry Wageningen University Thesis co-supervisor Dr. H. A. Schols Associate Professor, Laboratory of Food Chemistry Wageningen University Other members Dr. E. Bonnin Institut National de la Recherche Agronomique (INRA), Nantes, France Prof. dr. J. van der Oost Wageningen University Prof. dr. J. G. M. Sanders Wageningen University Dr. J. A. M. de Bont C5 Yeast Company B. V., Bergen op Zoom This research was conducted under the auspices of the Graduate School VLAG (Graduate School of Nutrition, Food Technology, Agrobiotechnology and Health Sciences) Characterization of cell wall degrading enzymes from Chrysosporium lucknowense C1 and their use to degrade sugar beet pulp Stefan Kühnel Thesis submitted in fulfilment of the requirements for the degree of doctor at Wageningen University by the authority of the Rector Magnificus Prof. dr. M. J. Kropff, in the presence of the Thesis Committee appointed by the Academic Board to be defended in public on Friday 9 September 2011 at 4 p.m. in the Aula. Stefan Kühnel Characterization of cell wall degrading enzymes from Chrysosporium lucknowense C1 and their use to degrade sugar beet pulp 192 pages PhD thesis Wageningen University, NL (2011) With references, with summaries in English, Dutch and German ISBN: 978-90-8585-978-9 Abstract Kühnel, S Characterization of cell wall degrading enzymes from Chrysosporium lucknowense C1 and their use to degrade sugar beet pulp Ph.D. thesis Wageningen University, The Netherlands, 2011 Key words Pectin, arabinan, biorefinery, mode of action, branched arabinose oligomers, ferulic acid esterase, arabinohydrolase, pretreatment Sugar beet pulp is the cellulose and pectin-rich debris remaining after sugar extrac- tion from sugar beets.
    [Show full text]
  • Panax Ginseng Callus, Suspension, and Root Cultures: Extraction and Qualitative Analysis Lyubov S
    Dyshlyuk L.S. et al. Foods and Raw Materials, 2020, vol. 8, no. 2, pp. 369–376 E-ISSN 2310-9599 Foods and Raw Materials, 2020, vol. 8, no. 2 ISSN 2308-4057 Research Article DOI: http://doi.org/10.21603/2308-4057-2020-2-369-376 Open Access Available online at http://jfrm.ru/en Panax ginseng callus, suspension, and root cultures: extraction and qualitative analysis Lyubov S. Dyshlyuk , Anastasia I. Dmitrieva* , Svetlana A. Ivanova , Yuliya V. Golubcova, Lev A. Ostroumov Kemerovo State University, Kemerovo, Russia * e-mail: [email protected] Received May 29, 2020; Accepted in revised form June 11, 2020; Published August 25, 2020 Abstract: Introduction. In recent years, scientists have been actively searching for medicinal plants containing biologically active substances with geroprotective properties to treat diseases of old age, in particular cancer, diabetes, cardiovascular diseases, and others. Ginseng (Panax ginseng L.) is a promising source of geroprotective compounds. We aimed to select optimal parameters for extracting organic compounds from ginseng callus, suspension, and root cultures and analyze their qualitative composition. Study objects and methods. We studied ginseng callus, suspension, and root cultures, as well as their extracts. Biologically active substances were extracted with 30 to 70% ethanol. Organic compounds were determined by thin-layer chromatography. The results for each plant were archived and analyzed for the presence of quercetin, mangiferin, luteolin, rutin, quercetin-2-D-glucoside, malvidin, as well as caffeic, cinnamic, ferulic, and sinapinic acids. Results and discussion. We developed a procedure for screening solvents and performed a fractional qualitative analysis of biologically active substances extracted from ginseng.
    [Show full text]
  • Application of MALDI Mass Spectrometry in Natural Products Analysis
    Reviews 671 Application of MALDI Mass Spectrometry in Natural Products Analysis Authors Ricardo Silva 1, Norberto Peporine Lopes1, Denise Brentan Silva 1, 2 Affiliations 1 Núcleo de Pesquisa em Produtos Naturais e Sintéticos (NPPNS), Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil 2 Laboratório de Produtos Naturais e Espectrometria de Massas (LAPNEM), Centro de Ciências Biológicas e da Saúde (CCBS), Universidade Federal de Mato Grosso do Sul (UFMS), Campo Grande, MS, Brazil Key words Abstract DHAP: 2,5-dihydroxyacetophenone l" MALDI ! DHB: 2,5-dihydroxybenzoic acid l" dereplication This article presents the utility of mass spectrom- DIT: dithranol l" natural products etry with a MALDI ionization source in natural EI: electron ionization l" fragmentation products analysis. The advantages and drawbacks FAB: fast atom bombardment l" data processing of this technique for natural products analyses FT: Fourier transform will be presented and discussed. In addition, the IAA: trans-3-indoleacrylic acid structural determination of secondary metabo- ICR: ion cyclotron resonance lites using MALDI‑MS/MS will be explored, which IMS: imaging mass spectrometry received May 3, 2015 can guide MALDI experimental methods and IT: ion trap revised March 1, 2016 stimulate new research in this area. Finally, sev- LDI: laser desorption/ionization accepted March 2, 2016 eral important approaches for MALDI data pro- LiDHB: lithium 2,4-dihydroxybenzoate Bibliography cessing will be discussed. HABA: 2-(4-hydroxyphenylazo)benzoic
    [Show full text]
  • Free Radicals Induced Oxidative Stress at a Molecular Level: the Current Status, Challenges and Perspectives of Computational Chemistry Based Protocols
    J. Mex. Chem. Soc. 2015, 59(4), 231-262 Article © 2015, Sociedad Química de México ISSN 1870-249X Free Radicals Induced Oxidative Stress at a Molecular Level: The Current Status, Challenges and Perspectives of Computational Chemistry Based Protocols Annia Galano1 1 To whom correspondence should be addressed. E-mail: [email protected]; [email protected] Departamento de Química. Universidad Autónoma Metropolitana-Iztapalapa. San Rafael Atlixco 186, Col. Vicentina. Iztapalapa. C. P. 09340. México D. F. México. Received September 14th, 2015; Accepted January 18th, 2016 Abstract. Oxidative stress is frequently caused by an excess of free Resumen. El estrés oxidativo frecuentemente es causado por un exce- radicals and has been associated with a wide variety of health disor- so de radicales libres, y ha sido asociado con una amplia variedad de ders. Therefore, finding strategies for scavenging free radicals has be- problemas de salud. Es por ello que encontrar estrategias viables para come an active area of research. This review summarizes, from a eliminar radicales libres se ha convertido en una activa área de inves- physicochemical perspective, relevant strategies to fight oxidative tigación. Esta reseña resume, desde una perspectiva fisicoquímica, stress via antioxidants, including prevention, deactivation of oxidants, estrategias relevantes para combatir el estrés oxidativo por medio de and repair of damaged targets. Different reaction mechanisms in- antioxidantes incluyendo prevención, desactivación de oxidantes, y volved in the chemical protection exerted by antioxidants are dis- reparación de blancos dañados. Se discuten diferentes mecanismos de cussed, as well as their relative importance depending on several reacción involucrados en la protección química que ejercen los an- aspects.
    [Show full text]
  • Grape Pip/CD
    Research Grape Seed Extract Abstracts The cellular and molecular basis of health benefits of grape seed proanthocyanidin extract Red grape seed extract containing proanthocyanidins and other antioxidants are being used as nutritional supplements by many health conscious individuals. The beneficial effects of grape seed proanthocyanidins (GSPE) have been reported, however, little is known about their mechanism(s) of action. One of the beneficial effects of GSPE is chemoprevention of cellular damage. The precise mechanism by which GSPE mediates, chemoprevention is not yet understood. This report addresses this issue. We investigated the mechanisms of actions of GSPE, which ameliorates chemotherapy-induced toxic effects of Idarubicin (Ida) and 4,-hydroxyperoxycyclophosphamide (4-HC) in normal human Chang liver cells. Exposure to GSPE resulted in a significant reduction in apoptosis in response to the cytotoxicity of chemotherapeutic agents. RT-PCR analysis showed a significant increase in the anti-apoptotic gene Bcl-2 and a decrease in the cell cycle associated and proapoptotic genes, c-myc and p53 in cells treated with GSPE. These results suggest that some of the chemopreventive effects of GSPE are mediated by upregulating Bcl-2 and down regulating c-myc and p53 genes. Joshi SS, Kuszynski CA, Bagchi D Curr Pharm Biotechnol 2001 Jun;2(2):187-200. Free radicals scavenging action and anti-enzyme activities of procyanidines from Vitis vinifera. A mechanism for their capillary protective action The scavenging by procyanidines (polyphenol oligomers from Vitis vinifera seeds, CAS 85594-37-2) of reactive oxygen species (ROS) involved in the onset (HO degrees) and the maintenance of microvascular injury (lipid radicals R degrees, RO degrees, ROO degrees) has been studied in phosphatidylcholine liposomes (PCL), using two different models of free radical generation: a) iron-promoted and b) ultrasound-induced lipid peroxidation.
    [Show full text]
  • Sinapic Acid and Its Derivatives As Medicine in Oxidative Stress-Induced Diseases and Aging
    Hindawi Publishing Corporation Oxidative Medicine and Cellular Longevity Volume 2016, Article ID 3571614, 10 pages http://dx.doi.org/10.1155/2016/3571614 Review Article Sinapic Acid and Its Derivatives as Medicine in Oxidative Stress-Induced Diseases and Aging Chunye Chen Key Laboratory of Biorheological Science and Technology, Ministry of Education, Bioengineering College, Chongqing University, Chongqing 400030, China Correspondence should be addressed to Chunye Chen; [email protected] Received 29 October 2014; Revised 2 January 2015; Accepted 12 January 2015 Academic Editor: Mat´ıas Mosqueira Copyright © 2016 Chunye Chen. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Sinapic acid (3,5-dimethoxy-4-hydroxycinnamic acid) is an orally bioavailable phytochemical, extensively found in spices, citrus and berry fruits, vegetables, cereals, and oilseed crops and is known to exhibit antioxidant, anti-inflammatory, anticancer, antimutagenic, antiglycemic, neuroprotective, and antibacterial activities. The literature reveals that sinapic acid is a bioactive phenolic acid and has the potential to attenuate various chemically induced toxicities. This minireview is an effort to summarize the available literature about pharmacokinetic, therapeutic, and protective potential of this versatile molecule in health related areas. 1. Introduction Sinapicacidexistsinbothfreeandesterform;some esters are sinapoyl esters, sinapine (sinapoylcholine), and As a result of metabolic processes, there is continuous pro- sinapoyl malate [8, 9]. Sinapic acid is a phytochemical found duction of reactive oxygen species (ROS), such as hydroxyl in various edible plants such as spices, citrus and berry fruits, radicals [1], in human body.
    [Show full text]
  • Original Article Utilizing Network Pharmacology to Explore the Underlying Mechanism of Cinnamomum Cassia Presl in Treating Osteoarthritis
    Int J Clin Exp Med 2019;12(12):13359-13369 www.ijcem.com /ISSN:1940-5901/IJCEM0100310 Original Article Utilizing network pharmacology to explore the underlying mechanism of Cinnamomum cassia Presl in treating osteoarthritis Guowei Zhou, Ruoqi Li, Tianwei Xia, Chaoqun Ma, Jirong Shen Affiliated Hospital of Nanjing University of Chinese Medicine, Nanjing 210029, Jiangsu, China Received July 30, 2019; Accepted October 8, 2019; Epub December 15, 2019; Published December 30, 2019 Abstract: Objective: The network pharmacology method was adopted to establish the relationship between “Ingre- dients-Disease Targets-Biological Pathway”, screen the potential target of Cinnamomum cassia Presl in treating osteoarthritis (OA), and explore the underlying mechanism. Methods: Chemical components and selected targets related to Cinnamomum cassia Presl were retrieved from BATMAN-TCM. OA disease targets were searched from TTD, DrugBank, OMIM, GAD, PharmGKB, and DisGeNET databases. Canonical SMILES were obtained from Pub- chem, and targets were obtained from SwissTargetPrediction. We constructed a target interaction network graph by using the STRING database and Cytoscape 3.2.1, and screened key targets by using the MCC algorithm of cytoHubba. Enrichment analysis of the GO function and KEGG pathway was conducted using the DAVID database. Results: Eighteen active compounds derived from Cinnamomum cassia Presl and 40 intersections between Cin- namomum cassia Presl and OA were obtained. Ten key targets were screened by the MCC algorithm, including PTGS2, MAPK8, MMP9, ALB, MMP2, MMP1, SERPINE1, TGFB1, PLAU, and ESR1. The GO analysis consisted of 33 enrichment results, including biological processes (e.g., collagen catabolic process and inflammatory response), cell composition (e.g., extracellular space and extracellular matrix), and molecular function (e.g., heme binding and aromatase activity).
    [Show full text]
  • Heidker Unr 0139D 12054.Pdf
    University of Nevada, Reno Metabolic Effects of a Grape Seed Procyanidin Extract and its Relation to Bile Acid Homeostasis A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Cell and Molecular Biology By Rebecca M. Heidker Dr. Marie-Louise Ricketts/Dissertation Advisor May, 2016 Copyright by Rebecca M. Heidker 2016 All rights reserved THE GRADUATE SCHOOL We recommend that the dissertation prepared under our supervision by REBECCA HEIDKER Entitled Metabolic Effects Of Grape Seed Procyanidin Extract On Risk Factors Of Cardiovascular Disease be accepted in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY Marie-Louise Ricketts, Advisor Patricia Berinsone, Committee Member Patricia Ellison, Committee Member Cynthia Mastick, Committee Member Thomas Kidd, Graduate School Representative David W. Zeh, Ph. D., Dean, Graduate School May, 2016 i Abstract Bile acid (BA) recirculation and synthesis are tightly regulated via communication along the gut-liver axis and assist in the regulation of triglyceride (TG) and cholesterol homeostasis. Serum TGs and cholesterol are considered to be treatable risk factors for cardiovascular disease, which is the leading cause of death both globally and in the United States. While pharmaceuticals are common treatment strategies, nearly one-third of the population use complementary and alternative (CAM) therapy alone or in conjunction with medications, consequently it is important that we understand the mechanisms by which CAM treatments function at the molecular level. It was previously demonstrated that one such CAM therapy, namely a grape seed procyanidin extract (GSPE), reduces serum TGs via the farnesoid X receptor (Fxr).
    [Show full text]