DOCSLIB.ORG

An Update on Antitumor Activity of Naturally Occurring Chalcones

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
An Update on Antitumor Activity of Naturally Occurring Chalcones Hindawi Publishing Corporation Evidence-Based Complementary and Alternative Medicine Volume 2013, Article ID 815621, 22 pages http://dx.doi.org/10.1155/2013/815621 Review Article An Update on Antitumor Activity of Naturally Occurring Chalcones En-Hui Zhang,1 Ru-Feng Wang,1 Shu-Zhen Guo,2 and Bin Liu1 1 School of Chinese Medicine, Beijing University of Chinese Medicine, Beijing 100102, China 2 School of Preclinical Medicine, Beijing University of Chinese Medicine, Beijing 100029, China Correspondence should be addressed to Bin Liu; [email protected] Received 15 January 2013; Accepted 19 March 2013 Academic Editor: Yoshiyuki Kimura Copyright © 2013 En-Hui Zhang et al. 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. Chalcones, which have characteristic 1,3-diaryl-2-propen-1-one skeleton, are mainly produced in roots, rhizomes, heartwood, leaves, and seeds of genera Angelica,Sophora,Glycyrrhiza,Humulus,Scutellaria,Parartocarpus,Ficus,Dorstenia,Morus,Artocarpus, and so forth. They have become of interest in the research and development of natural antitumor agents over the past decades due to their broad range of mechanisms including anti-initiation, induction of apoptosis, antiproliferation, antimetastasis, antiangiogenesis, and so forth. This review summarizes the studies on the antitumor activity of naturally occurring chalcones and their underlying mechanisms in detail during the past decades. 1. Introduction biosynthesis of flavonoids. Structurally, they are a group of compounds bearing 1,3-diaryl-2-propen-1-one framework, Chalcones are one of the subclasses of flavonoid family. which consists of open-chain flavonoids in which the two Theyarecommonlyknownasyellowpigmentsinflowers, aromatic rings are joined together by three carbons in an ,- and are also widely distributed in various parts (roots, unsaturated system. Chemically, they can be easily cyclized rhizomes, heartwood, buds, leaves, flowers, and seeds) of by a Michael addition at the position of the carbonyl species of genera Angelica, Sophora, Glycyrrhiza, Humulus, to form a flavanone. The existence of double bond results Scutellaria, Parartocarpus, Ficus, Dorstenia, Morus, Artocar- in cis and trans isomeric forms of chalcone in nature, of pus, and so forth. A wide range of biological activities which the trans form is thermodynamically stable. Chalcone have been attributed to chalcones, including antitumor, is one of the most structurally diverse groups of flavonoids antimutagenic, anti-inflammatory, antioxidant, antifungal, existing as dimmers, oligomers, Diels-Alder adducts, and antibacterial, antiprotozoal, analgesic, and gastric protective conjugates of various kinds. Additionally, the attachment of properties [1]. As for antitumor activity, chalcones exhibit varieties of hydroxyl, methoxy, and alkenyl functionalities various effects including anti-initiation, apoptosis induction, to the framework of chalcone contributes to its structural antiproliferation, antimetastasis, antiangiogenesis, and so diversity as well [3]. forth.Thisreviewsummarizesthestudiesontheantitumor During the last decade, about 90 compounds of chalcones activity of naturally occurring chalcones and their underlying with various antitumor activities were reported. They can mechanisms in detail during the past decade and also briefly be roughly categorized into 4 large groups, namely, chal- categorized these compounds on the basis of their structures. cones with O-substitution, prenylated chalcones, Diels-Alder adducts, and others. All these 90 compounds are shown in Figure 1. 2. Structures Chalcones, a term introduced by Kostanecki and Tabor 2.1. Chalcones with O-Substitution. This group of compounds [2], are considered as the precursors of flavones in the (1–26) carries a varying number of O-substituents on A-ring 2 Evidence-Based Complementary and Alternative Medicine 3 2 4 3 4 2 5 6 5 6 O 2 3 4 5 6 2 3 4 5 6 1 H H OH H OH H OH OH H H 2 OCH3 H OCH3 HOHH H H HH 3 OH H OCH3 HOHH H H HH 4 OH H OH HH HOCH3 OCH3 HH 5 OH H OH HHOCH3 OCH3 H HH 6 OH H OH HH H HOCH3 HH 7 OH CH3 OHCH3 OCH3 H H H H H 8 OCH3 HOHCH3 OHH H H HH 9 OCH3 HOHHOHH H H HH 10 OH HOHH H H H H HH 11 OCH3 HOHH H H H OHHH 12 OH HOHH H H H OHHH 13 OH HHHHOHHHOCH3 OCH3 14 OH H OCH3 HOHH H H HH 15 HOHOHH HOCH3 H OHHOCH3 16 OCH3 H OCH3 HOHH HOCH3 HH 17 OCH3 H OCH3 HOHH H OHHH 18 O--D-Glc H OH H OH H H OH HH 19 OH H OH H OH H HOH H H 20 OCH3 H OH CHO OH H H H H H 21 OH H OCH3 HHOCH3 OCH3 OCH3 HH OH O OH HO OH H O R O OH O 1 O O OH OR2 H O HO OH O OH HO R1 R2 OH O 23 CH3 CH3 22 24 HH 25 CH3 H (a) Figure 1: Continued. Evidence-Based Complementary and Alternative Medicine 3 OH O H3CO OH O OH OH O 26 3 2 4 3 5 4 2 6 5 6 O 2 3 4 5 6 2 3 4 5 6 27 HHOHHOH HPreOHOCH3 H 28 OCH3 H OH Ger OH H H H H H 29 OH Ger OH H OH H H OH H H 30 OH Pre OH PreOCH3 H H OH H H 31 OH OH HOCH H H OH H H OH 3 32 OH Pre OH H OH H H OH H H 33 OH Pre OCH3 H OH H H OH H H 34 OH Pre OCH3 H OCH3 H H OH H H 35 HH OHHHH OH H OCH3 36 HH OHHHHHOH OCH3 37 HH OHHHH OH H OCH3 38 OH Pre OH H OCH3 OH H OH H H 39 H Ger OH H OH H H OH H H 40 H H OH Pre OH HHHH H 41 HHOCH3 Pre OH HHHH H 42 OH Pre OH H H H H OH H H OH 43 OH OCH3 HHH HOH HH 44 H H OH Ger OH H H OH H H 45 OH Pre OH H H H Pre OH H H 46 OH H OH Pre H H Pre OH H H 47 H H Pre OCH3 OH H H OH H H 48 H H OCH3 Ger OH H H OH H H 49 OCH3 H OH Pre OH H H OH H H (b) Figure 1: Continued. 4 Evidence-Based Complementary and Alternative Medicine R Δ 6 R5 R1 R2 R3 R4 R5 R6 O 50 HHOH OH HH R2 HO R 1 R4 51 H H OH OH H OH Δ satd. 52 H H OH OH OH OH Δ satd. 53 OH Pre H H H H R3 O R1 R2 R3 R4 R5 R6 54 OHOCH3 H H OH H R6 R4 Δ 55 OHOCH3 H H OH H Δ satd. R3 R5 56 OH H H H OH H O R 1 57 OH H H H OH H Δ satd. 58 OCH3 OH OH H OH Pre Δ satd. 59 OH H H H H H R2 O 60 OH H H OHOCH3 H 61 OH H H H OCH3 H 62 OH H H H OH H R 2 R3 R R1 OH 2 O O H3CO R3O O R1 O R1 R2 R3 R1 R2 R3 63 OH H CH3 65 OH H Pre 64 HHPre 66 H OCH3 CH3 HO OCH3 OH OH O O O HO OH O 67 68 OH O HO O OH OH O OH O 69 70 (c) Figure 1: Continued. Evidence-Based Complementary and Alternative Medicine 5 R4 R2 OH R2 R3 R1 O R1 O R R R R R1 R2 1 2 3 4 74 OH OCH OH H 71 OH OCH3 3 75 OCH3 OH OH H 72 OCH3 OH 73 OH OH 76 OH OH OH H 77 OH OHOCH3 OH 78 OH OCH3 OCH3 H HO OH HO HO OH O O OH OH HO O O OH OH O OH OH 79 80 OH R1 HO OH HO HO O O OH O O O OH H HO H R2 OH OH R1 R2 O 81 Pre H OH 83 82 H H OH HO OH OH HO O OH O OO OH H HO O OH OH HO OH OH O 84 85 (d) Figure 1: Continued. 6 Evidence-Based Complementary and Alternative Medicine OH OH HO O OH HO O O O O OH O HO OH HO OH OH 86 87 OH OH HO O HO O O O OH OH OH O OH O HO O HO O OH OH HO HO OH OH 88 89 OH OH HO HO OCH3 OH OH R2 R OH O O OCH3 R1 OH O R HO OH 94 OH 95 OCH3 R1 R2 90 OH OH OH O 91 H OH 92 OH H HO 93 H H OH HO OH OCH HO 3 Δ O OH 97 Δ satd. OH OH O 98 96 (e) Figure 1: Continued. Evidence-Based Complementary and Alternative Medicine 7 OH HO OH O OH HO O O O HO HO OH 99 (f) Figure 1: Structures of chalcones. and B-ring, including hydroxyl and methoxy groups. These 3.1. Cytotoxicity. In most cases, cell cytotoxicity was moni- groups are usually located at C-2 ,C-4, C-6 , and C-4 and toredusingtheMTTorMTSassay.Treatmentofcellswith seldom appear at C-3 , C-5 , C-2, C-3, and C-6. In addition, chalcones can cause a decrease in cell viability, and then 2 O-glycosylated chalcones (18, 22)aswellas4O-chalcone thecellsundergorapidnecrosisoractivateaprogrammed dimmers (23–26) are also included in this group.
Load more

Recommended publications
  • Key Enzymes Involved in the Synthesis of Hops Phytochemical Compounds: from Structure, Functions to Applications
    International Journal of Molecular Sciences Review Key Enzymes Involved in the Synthesis of Hops Phytochemical Compounds: From Structure, Functions to Applications Kai Hong , Limin Wang, Agbaka Johnpaul , Chenyan Lv * and Changwei Ma * College of Food Science and Nutritional Engineering, China Agricultural University, 17 Qinghua Donglu Road, Haidian District, Beijing 100083, China; [email protected] (K.H.); [email protected] (L.W.); [email protected] (A.J.) * Correspondence: [email protected] (C.L.); [email protected] (C.M.); Tel./Fax: +86-10-62737643 (C.M.) Abstract: Humulus lupulus L. is an essential source of aroma compounds, hop bitter acids, and xanthohumol derivatives mainly exploited as flavourings in beer brewing and with demonstrated potential for the treatment of certain diseases. To acquire a comprehensive understanding of the biosynthesis of these compounds, the primary enzymes involved in the three major pathways of hops’ phytochemical composition are herein critically summarized. Hops’ phytochemical components impart bitterness, aroma, and antioxidant activity to beers. The biosynthesis pathways have been extensively studied and enzymes play essential roles in the processes. Here, we introduced the enzymes involved in the biosynthesis of hop bitter acids, monoterpenes and xanthohumol deriva- tives, including the branched-chain aminotransferase (BCAT), branched-chain keto-acid dehydroge- nase (BCKDH), carboxyl CoA ligase (CCL), valerophenone synthase (VPS), prenyltransferase (PT), 1-deoxyxylulose-5-phosphate synthase (DXS), 4-hydroxy-3-methylbut-2-enyl diphosphate reductase (HDR), Geranyl diphosphate synthase (GPPS), monoterpene synthase enzymes (MTS), cinnamate Citation: Hong, K.; Wang, L.; 4-hydroxylase (C4H), chalcone synthase (CHS_H1), chalcone isomerase (CHI)-like proteins (CHIL), Johnpaul, A.; Lv, C.; Ma, C.
    [Show full text]
  • Beer As a Source of Hop Prenylated Flavonoids, Compounds with Antioxidant, Chemoprotective and Phytoestrogen Activity
    BEER AS A SOURCE OF HOP PRENYLATED FLAVONOIDS, COMPOUNDS WITH ANTIOXIDANT, CHEMOPROTECTIVE AND PHYTOESTROGEN ACTIVITY Dana Urminská*1 and Nora Jedináková2 Address(es): Doc. RNDr. Dana Urminská, CSc., 1Slovak University of Agriculture, Faculty of Biotechnology and Food Sciences, Department of Biochemistry and Biotechnology, Trieda Andreja Hlinku 2, 949 76 Nitra-Chrenová, Slovakia, phone number: +421 37 641 4696. *Corresponding author: [email protected] https://doi.org/10.15414/jmbfs.4426 ARTICLE INFO ABSTRACT Received 4. 3. 2021 Beer is an alcoholic beverage consumed worldwide, which is given its typical taste by the presence of hops. Hops contain an array Revised 1. 6. 2021 technologically important substances, which are primarily represented by hop resins (humulones, lupulones, humulinones, hulupones, Accepted 1. 6. 2021 etc.), essential oils (humulene, myrcene, etc.) and tannins (phenolic compounds quercetin, catechin, etc.). In addition to their sensory Published 1. 8. 2021 properties, these molecules contribute to the biological and colloidal stability of beer with their antiseptic and antioxidant properties. Recently, an increased attention has been given to prenylated hop flavonoids, particularly xanthohumol, isoxanthohumol and 8- prenylnaringenin. Xanthohumol is a prenylated chalcone that exhibit antioxidant, anticancer and chemoprotective effects. Its only source Regular article in human nutrition is beer, nevertheless a large part of xanthohumol from hops is isomerized by heat to isoxanthohumol and desmethylxanthohumol, from which a racemic mixture of 6- and 8-prenylnaringenins is formed during the beer production. Xanthohumol is also converted to isoxanthohumol by digestion, leading to the formation of 8-prenylnaringenin that is being catalyzed by the enzymes of the intestinal microorganisms as well as liver enzymes.
    [Show full text]
  • (12) Patent Application Publication (10) Pub. No.: US 2004/0121040 A1 Forster Et Al
    US 20040121040A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2004/0121040 A1 Forster et al. (43) Pub. Date: Jun. 24, 2004 (54) METHOD OF PRODUCING A (21) Appl. No.: 10/724,237 XANTHOHUMOL-CONCENTRATED HOP EXTRACTED AND USE THEREOF (22) Filed: Dec. 1, 2003 (75) Inventors: Adrian Forster, Wolnzach (DE); Josef (30) Foreign Application Priority Data Schulmeyr, Wolnzach (DE); Roland Schmidt, Wolnzach (DE); Karin Nov. 30, 2002 (DE)..................................... 102 56 O31.5 Simon, Pfaffenhofen (DE); Martin O O Ketterer, Wolnzach (DE); Birgit Publication Classification Forchhammer, Neustadt (DE); Stefan 7 Geyer, Wolnzach (DE); Manfred s - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - close Gehrig, Woln Zach (DE) ( ) O O - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - - f Correspondence Address: (57) ABSTRACT BROWDY AND NEIMARK, P.L.L.C. 624 NINTH STREET, NW SUTE 300 In a method of producing a Xanthohumol-concentrated hop WASHINGTON, DC 20001-5303 (US) extract, the Xanthohumol-containing hop extract is extracted from a Xanthohumol-containing hop raw material by highly (73) Assignee: NATECO2 GMBH & CO. KG, Woln compressed CO as a solvent at pressures above 500 bar and Zach (DE) temperatures above 60° C. US 2004/O121040 A1 Jun. 24, 2004 METHOD OF PRODUCING A the finished beer or other kinds of food or used by itself as XANTHOHUMOL-CONCENTRATED HOP a chemo-preventive preparation. EXTRACTED AND USE THEREOF 0010 Presently, there are two prior art solutions. DE 199 39350 A1 describes a method of producing a xanthohumol BACKGROUND OF THE INVENTION enriched hop extract, with combinations of water and etha nol being used preferably in two steps of extraction. 5 to 15 0001) 1. Field of the Invention percent by weight of Xanthohumol are specified as being 0002 The invention relates to a method of producing a typical.
    [Show full text]
  • Xanthohumol, a Prenylated Chalcone Derived from Hops, Inhibits Growth and Metastasis of Melanoma Cells
    cancers Article Xanthohumol, a Prenylated Chalcone Derived from Hops, Inhibits Growth and Metastasis of Melanoma Cells Tatjana Seitz 1,2, Christina Hackl 3, Kim Freese 1, Peter Dietrich 1,4 , Abdo Mahli 1 , Reinhard Manfred Thasler 5, Wolfgang Erwin Thasler 6, Sven Arke Lang 7, Anja Katrin Bosserhoff 1,8 and Claus Hellerbrand 1,2,8,* 1 Institute of Biochemistry (Emil-Fischer-Zentrum), Friedrich-Alexander University Erlangen-Nürnberg, D-91054 Erlangen, Germany; [email protected] (T.S.); [email protected] (K.F.); [email protected] (P.D.); [email protected] (A.M.); [email protected] (A.K.B.) 2 Department of Internal Medicine I, University Hospital Regensburg, D-93053 Regensburg, Germany 3 Department of Surgery, University Hospital Regensburg, D-93053 Regensburg, Germany; [email protected] 4 Medical Clinic 1, Department of Medicine, University Hospital Erlangen, Friedrich-Alexander-University, D-91054 Erlangen, Germany 5 Stiftung HTCR, BioPark III, Am BioPark 13, D-93053 Regensburg, Germany; [email protected] 6 Hepacult GmbH, D-82152 Martinsried, Germany; [email protected] 7 Department of Surgery and Transplantation, University Hospital RWTH Aachen, D-52074 Aachen, Germany; [email protected] 8 Comprehensive Cancer Center (CCC) Erlangen-EMN, D-91054 Erlangen, Germany * Correspondence: [email protected] Simple Summary: Melanoma is an aggressively growing form of skin cancer. It has a high metastatic Citation: Seitz, T.; Hackl, C.; potential, and the liver is one of the most common sites for visceral metastasis. Patients with Freese, K.; Dietrich, P.; Mahli, A.; hepatic metastases have a very poor prognosis, and effective forms of treatment are urgently needed.
    [Show full text]
  • Hop Compounds: Extraction Techniques, Chemical Analyses, Antioxidative, Antimicrobial, and Anticarcinogenic Effects
    nutrients Review Hop Compounds: Extraction Techniques, Chemical Analyses, Antioxidative, Antimicrobial, and Anticarcinogenic Effects Maša Knez Hrnˇciˇc 1,†, Eva Španinger 2,†, Iztok Jože Košir 3, Željko Knez 1 and Urban Bren 2,* 1 Laboratory of Separation Processes and Product Design, Faculty of Chemistry and Chemical Engineering, University of Maribor, Smetanova ulica 17, SI-2000 Maribor, Slovenia; [email protected] (M.K.H.); [email protected] (Ž.K.) 2 Laboratory of Physical Chemistry and Chemical Thermodynamics, Faculty of Chemistry and Chemical Engineering, University of Maribor, Smetanova ulica 17, SI-2000 Maribor, Slovenia; [email protected] 3 Slovenian Institute of Hop Research and Brewing, Cesta Žalskega Tabora 2, SI-3310 Žalec, Slovenia; [email protected] * Correspondence: [email protected]; Tel.: +386-2-2294-421 † These authors contributed equally to this work. Received: 7 December 2018; Accepted: 18 January 2019; Published: 24 January 2019 Abstract: Hop plants comprise a variety of natural compounds greatly differing in their structure and properties. A wide range of methods have been developed for their isolation and chemical analysis, as well as for determining their antioxidative, antimicrobial, and antigenotoxic potentials. This contribution provides an overview of extraction and fractionation techniques of the most important hop compounds known for their health-promoting features. Although hops remain the principal ingredient for providing the taste, stability, and antimicrobial protection of beer, they have found applications in the pharmaceutical and other food industries as well. This review focuses on numerous health-promoting effects of hops raging from antioxidative, sedative, and anti-inflammatory potentials, over anticarcinogenic features to estrogenic activity.
    [Show full text]
  • Biogeography, Phylogeny and Divergence Date Estimates of Artocarpus (Moraceae)
    Annals of Botany 119: 611–627, 2017 doi:10.1093/aob/mcw249, available online at www.aob.oxfordjournals.org Out of Borneo: biogeography, phylogeny and divergence date estimates of Artocarpus (Moraceae) Evelyn W. Williams1,*, Elliot M. Gardner1,2, Robert Harris III2,†, Arunrat Chaveerach3, Joan T. Pereira4 and Nyree J. C. Zerega1,2,* 1Chicago Botanic Garden, Plant Science and Conservation, 1000 Lake Cook Road, Glencoe, IL 60022, USA, 2Northwestern University, Plant Biology and Conservation Program, 2205 Tech Dr., Evanston, IL 60208, USA, 3Faculty of Science, Genetics Downloaded from https://academic.oup.com/aob/article/119/4/611/2884288 by guest on 03 January 2021 and Environmental Toxicology Research Group, Khon Kaen University, 123 Mittraphap Highway, Khon Kaen, 40002, Thailand and 4Forest Research Centre, Sabah Forestry Department, PO Box 407, 90715 Sandakan, Sabah, Malaysia *For correspondence. E-mail [email protected], [email protected] †Present address: Carleton College, Biology Department, One North College St., Northfield, MN 55057, USA. Received: 25 March 2016 Returned for revision: 1 August 2016 Editorial decision: 3 November 2016 Published electronically: 10 January 2017 Background and Aims The breadfruit genus (Artocarpus, Moraceae) includes valuable underutilized fruit tree crops with a centre of diversity in Southeast Asia. It belongs to the monophyletic tribe Artocarpeae, whose only other members include two small neotropical genera. This study aimed to reconstruct the phylogeny, estimate diver- gence dates and infer ancestral ranges of Artocarpeae, especially Artocarpus, to better understand spatial and tem- poral evolutionary relationships and dispersal patterns in a geologically complex region. Methods To investigate the phylogeny and biogeography of Artocarpeae, this study used Bayesian and maximum likelihood approaches to analyze DNA sequences from six plastid and two nuclear regions from 75% of Artocarpus species, both neotropical Artocarpeae genera, and members of all other Moraceae tribes.
    [Show full text]
  • The Systematic Wood Anatomy of the Moraceae (Urticales) V. Genera of the Tribe Moreae Without Urticaceous Stamens *
    IAWA Bulletin n.s., Vol. 7 (3),1986 175 THE SYSTEMATIC WOOD ANATOMY OF THE MORACEAE (URTICALES) V. GENERA OF THE TRIBE MOREAE WITHOUT URTICACEOUS STAMENS * by B.1. H. ter Welle, 1. Koek-Noorman and S. M. C. Topper Institute of Systematic Botany, University of Utrecht, Heidelberglaan 2, 3508 TC Utrecht, The Netherlands Summary The wood anatomy of the Moreae without based upon these characters, however (Berg, urticaceous stamens is described in detail. Ge­ 1983), is not in accordance with the tribes neric descriptions of the following genera are Moreae and Artocarpeae sensu Corner (1962). provided: Antiaropsis, Artocarpus, Bagassa, Ba­ Both Berg's and Corner's subdivisions deviate tocarpus, Clarisia, Parartocarpus, Poulsenia, from older classifications, as given by, for in­ Prainea, Sorocea, Sparattosyce, and Treculia. stance, Bentham and Hooker (1880) and Engler Wood anatomical variation below the genus (1888). level is very limited, except in the genus Clari­ The Moreae characterised by the absence of sia. Intergeneric variation, however, is much urticaceous stamens comprise the genera Antia­ more evident. Most genera can be recognised ropsis (New Guinea), Artocarpus (Southeast by the presence or absence of septate fibres, Asia), Bagassa (Neotropics), Batocarpus (Neo­ and of radial latex tubes, the size of the inter­ tropics), Clarisia (Neotropics), Hullettia (South­ vascular pits, the parenchyma distribution, and east Asia),Parartocarpus (Southeast Asia), Poul­ crystal distribution. The diagnostic and taxon­ senia (Neotropics), Prainea (Malesia), Sorocea omic value of several characters is discussed. (Neotropics), Sparattosyce (New Caledonia), Key words: Moraceae, Moreae, systematic wood and Treculia (Tropical Africa). anatomy. Methods and Materials In troduction The methods employed are those given in This paper is part of a series, in which the the first paper of this series (Koek-Noorman et wood anatomy of the Moraceae is described aI., 1984).
    [Show full text]
  • Protects Rat Tissues Against Oxidative Damage After Acute Ethanol Administration
    Toxicology Reports 1 (2014) 726–733 Contents lists available at ScienceDirect Toxicology Reports j ournal homepage: www.elsevier.com/locate/toxrep Xanthohumol, a prenylated flavonoid from hops (Humulus lupulus L.), protects rat tissues against oxidative damage after acute ethanol administration ∗ Carmen Pinto, Juan J. Cestero, Beatriz Rodríguez-Galdón, Pedro Macías Department of Biochemistry and Molecular Biology, Science Faculty, Extremadura University, Av. Elvas s/n, 06006 Badajoz, Spain a r a t i c l e i n f o b s t r a c t Article history: Ethanol-mediated free radical generation is directly involved in alcoholic liver disease. Received 9 June 2014 In addition, chronic alcohol bingeing also induces pathological changes and dysfunc- Received in revised form 5 September 2014 tion in multi-organs. In the present study, the protective effect of xanthohumol (XN) Accepted 8 September 2014 on ethanol-induced damage was evaluated by determining antioxidative parameters and Available online 16 September 2014 stress oxidative markers in liver, kidney, lung, heart and brain of rats. An acute treatment (4 g/kg b.w.) of ethanol resulted in the depletion of superoxide dismutase, catalase and Keywords: glutathione S-transferase activities and reduced glutathione content. This effect was accom- Xanthohumol panied by the increased activity of tissue damage marker enzymes (glutamate oxaloacetate Ethanol intoxication Rat transaminase, glutamate pyruvate transaminase and lactate dehydrogenase) and a signif- icant increase in lipid peroxidation and hydrogen peroxide concentrations. Pre-treatment Antioxidant defense system Serum enzymes with XN protected rat tissues from ethanol-induced oxidative imbalance and partially Stress oxidative mitigated the levels to nearly normal levels in all tissues checked.
    [Show full text]
  • On the Fate of Certain Hop Substances During Dry Hopping
    93 July / August 2013 (Vol. 66) BrewingScience Monatsschrift für Brauwissenschaft A. Forster and A. Gahr The scientifi c organ Yearbook 2006 of the Weihenstephan Scientifi c Centre of the TU Munich of the Versuchs- und Lehranstalt für Brauerei in Berlin (VLB) On the Fate of Certain Hop Substancesof the Scientifi c Station for Breweries in Munich of the Veritas laboratory in Zurich of Doemens wba – Technikum GmbH in Graefelfi ng/Munich www.brauwissenschaft.de during Dry Hopping Dry hopping is becoming increasingly popular especially in small breweries. It is a complex and sophisticated method, but it is exactly those qualities which make it a highly efficient method for craft brewers to stand out among the mass of other beers. Empirical experience is the key factor here in the choice of hops and type of application. There is still little known about the transfer rates of hop substances during dry hopping which can provide a great variability of application. A test was made in which four dry hopped pale lager beers were contrasted with a similar produced beer without dry hopping. Here the new German varieties Mandarina Bavaria, Hüll Melon, Hallertauer Blanc and Polaris were used for dry hopping. The dosed quantity of 1.5 ml/hl was based on the hop oil content. The transfer rates were calculated from the difference between analysis values of the dry hopped beers and the control beer divided by the dosed dry hopping quantities. As the calculations were made from three analytical values they inevitably produced relatively large ranges of fluctuation. Of the dosed α-acids, 4 to 5 % can be found in the beers, of the total polyphenols 50 to 60 % and of the low-molecular polyphenols 60 to 70 %.
    [Show full text]
  • Flora Malesiana Precursor for the Treatment of Moraceae 8: Other Genera Than Ficus
    BLUMEA 50: 535 –550 Published on 14 December 2005 http://dx.doi.org/10.3767/000651905X622815 FLORA MALESIANA PRECURSOR FOR THE TREATMENT OF MORACEAE 8: OTHER GENERA THAN FICUS C.C. BERG Bergen Museum, University of Bergen, Allégate 41, 5007 Bergen, Norway; Nationaal Herbarium Nederland, Universiteit Leiden branch, P.O. Box 9514, 2300 RA Leiden, The Netherlands. SUMMARY The tribe Artocarpeae is redefined, the tribe Soroceae is established by change of rank, and as a consequence a new tribe Antiaropsidae is established. Moreover, a new species Antiaropsis uniflora C.C. Berg is described. In Artocarpus a new species is described, A. albobrunneus C.C. Berg, one subspecies is raised to the rank of species, A. brevipedunculatus (F.M. Jarrett) C.C. Berg, and new subspecies are described in several species, A. longifolius Becc. subsp. adpressus C.C. Berg, A. teijs- mannii Miq. subsp. subglabrus C.C. Berg. In Prainea, P. papuana is reduced to a subspecies, P. limpato (Miq.) K. Heyne subsp. papuana (Becc.) C.C. Berg. In Streblus the sections Pseudomorus (Bureau) Corner and Taxotrophis (Blume) Corner are reinstated, S. urophyllus is reduced to a subspecies, S. glaber (Merr.) Corner subsp. urophyllus (Diels) C.C. Berg, in S. streblus var. australianus is raised to S. glaber subsp. australianus (C.T. White) C.C. Berg, and S. celebensis C.C. Berg is described as a new species. Key words: Moraceae, Artocarpeae, Antiaropsis, Artocarpus, Prainea, Streblus, Malesia. INTRODUCTION A precursory study on Moraceae focussed on its classification and the Asian repre- sentatives was published by Corner in 1962. It was preceded by a monographic study on Artocarpus and allied genera by Jarrett (1959a, b, c, 1960a, b).
    [Show full text]
  • Perennial Edible Fruits of the Tropics: an and Taxonomists Throughout the World Who Have Left Inventory
    United States Department of Agriculture Perennial Edible Fruits Agricultural Research Service of the Tropics Agriculture Handbook No. 642 An Inventory t Abstract Acknowledgments Martin, Franklin W., Carl W. Cannpbell, Ruth M. Puberté. We owe first thanks to the botanists, horticulturists 1987 Perennial Edible Fruits of the Tropics: An and taxonomists throughout the world who have left Inventory. U.S. Department of Agriculture, written records of the fruits they encountered. Agriculture Handbook No. 642, 252 p., illus. Second, we thank Richard A. Hamilton, who read and The edible fruits of the Tropics are nnany in number, criticized the major part of the manuscript. His help varied in form, and irregular in distribution. They can be was invaluable. categorized as major or minor. Only about 300 Tropical fruits can be considered great. These are outstanding We also thank the many individuals who read, criti- in one or more of the following: Size, beauty, flavor, and cized, or contributed to various parts of the book. In nutritional value. In contrast are the more than 3,000 alphabetical order, they are Susan Abraham (Indian fruits that can be considered minor, limited severely by fruits), Herbert Barrett (citrus fruits), Jose Calzada one or more defects, such as very small size, poor taste Benza (fruits of Peru), Clarkson (South African fruits), or appeal, limited adaptability, or limited distribution. William 0. Cooper (citrus fruits), Derek Cormack The major fruits are not all well known. Some excellent (arrangements for review in Africa), Milton de Albu- fruits which rival the commercialized greatest are still querque (Brazilian fruits), Enriquito D.
    [Show full text]
  • Xanthohumol, a Flavonoid from Hops(Humulus Lupulus): in Vitro and in Vivo Metabolism, Antioxidant Properties of Metabolites, and Risk Assessment in Humans
    AN ABSTRACT OF THE DISSERTATION OF Meltem Yilmazer for the degree of Doctor of Philosophy in Toxicology presented on January 5, 2001. Title: Xanthohumol, A Flavonoid From Hops(Humulus lupulus): In Vitro and In Vivo Metabolism, Antioxidant Properties of Metabolites, and Risk Assessment In Humans. Abstract approved: Redacted for Privacy Donald R. Buhler Reported here is an investigation to determine thein vitroandin vivometabolism of xanthohumol (XN). XN is the major prenylated flavonoid of the female inflorescences (cones) of the hop plant(Humulus lupulus).It is also a constituent of beer, the major dietary source of prenylated flavonoids. Recent studies have suggested that XN may have potential cancer chemopreventive activity but little is known about its metabolism. We investigated the in vitro metabolism of XN by rat and human liver microsomes, and cDNA-expressed cytochrome P450s, and the in vivo metabolism of XN by rats. The metabolites and conjugates were identified by using high-pressure liquid chromatography, liquid chromatography-mass spectrometry, and nuclear magnetic resonance. The antioxidant properties of two metabolites and two glucuronides were examined. The possible risk of XN consumption from beer or dietary supplements is discussed. The involvement of metabolites of XN in cancer chemoprevention remains to be established. ©Copynght by Meltem Yilmazer January 5, 2001 All Rights Reserved XANTHOHUMOL, A FLAVONOID FROM HOPS (Humulus lupulus): IN VITRO AND IN VIVO METABOLISM, ANTIOXIDANT PROPERTIES OF METABOLITES, AND RISK ASSESSMENT
    [Show full text]