Relation Structure/Activité De Tanins Bioactifs Contre Les Nématodes

Total Page:16

File Type:pdf, Size:1020Kb

Relation Structure/Activité De Tanins Bioactifs Contre Les Nématodes En vue de l'obtention du DOCTORAT DE L'UNIVERSITÉ DE TOULOUSE Délivré par : Institut National Polytechnique de Toulouse (INP Toulouse) Discipline ou spécialité : Pathologie, Toxicologie, Génétique et Nutrition Présentée et soutenue par : Mme JESSICA QUIJADA PINANGO le jeudi 17 décembre 2015 Titre : RELATION STRUCTURE/ACTIVITE DE TANINS BIOACTIFS CONTRE LES NEMATODES GASTROINTESTINAUX (HAEMONCHUS CONTORTUS) PARASITES DES PETITS RUMINANTS Ecole doctorale : Sciences Ecologiques, Vétérinaires, Agronomiques et Bioingénieries (SEVAB) Unité de recherche : Interactions Hôtes - Agents Pathogènes (IHAP) Directeur(s) de Thèse : M. HERVÉ HOSTE Rapporteurs : M. ADIBE LUIZ ABDALLA, UNIVERSIDAD DE SAO PAULO Mme HEIDI ENEMARK, NORWEGIAN VETERINARY INSTITUTE Membre(s) du jury : 1 M. FRANÇOIS SCHELCHER, ECOLE NATIONALE VETERINAIRE DE TOULOUSE, Président 2 M. HERVÉ HOSTE, INRA TOULOUSE, Membre 2 Mme CARINE MARIE-MAGDELAINE, INRA PETIT BOURG, Membre 2 M. SMARO SOTIRAKI, HAO-DEMETER, Membre 2 M. VINCENT NIDERKORN, INRA CLERMONT FERRAND, Membre QUIJADA J. 2015 Cette thèse est dédiée à mes parents, Teresa et Héctor, À mon mari, Rafäel, pour son soutien inconditionnel, son amour illimité, sa patience, sa loyauté, son amitié et surtout sa confidence, À ma grand-mère, Marcolina, car m'ait donné le plus grand et précieux cadeau en ma vie : ma foi en Dieu ma forteresse et mon espoir (Isaïas 41:13). À mes adorés sœurs, belle- sœurs et frère : Yurlin, Indira, Iskay, Olga, Zoraida et Jesus. Merci pour l’amour infini que m’ont toujours été donné, celui qu’a été prolongé par l'amour de mes merveilleux neveux. 1 QUIJADA J. 2015 REMERCIEMENTS Je remercie tout d’abord mon Dieu pour me donner le cadeau de la vie, et la forteresse pour vivre chaque jour. Je tiens à remercier le Dr. Hervé Hoste de l’équipe « Interaction Tanins-Nématodes Digestifs » de l’UMR 1225 INRA/ENVT « Interactions Hôtes-Agents Pathogènes », pour avoir dirigé mes travaux de recherche. Je lui suis vraiment reconnaissante pour son aide, ses conseils et son soutien pendant toutes ces années. Je tiens à le remercier pour sa disponibilité, sa patience et gentillesse, ses conseils, bienveillance et la confiance qu’il m’a témoignée dès le premier jour. Je vous remercie de me donner l’opportunité de rejoindre l’équipe de recherche pendant ces trois années, elles representeront en temps précieux dans ma vie professionnelle mais aussi personnelle. Merci beaucoup, pour avoir été le meilleur directeur de thèse que je puisse avoir eu. Je souhaite remercier le Pr. Adibe Luiz Abdalla de l’ « Universidade de São Paulo » et le Dr. Heidi Enemark du « Norwegian Veterinary Institute » d’avoir accepté d’être rapporteurs de mon travail de thèse. Ainsi, je tiens à remercier le Dr. Carine Marie- Magdeleine de l’INRA Petit Bourg, le Dr. Vincent Niderkorn de l’INRA Clermont-Ferrand et le Dr. Smaragda Sotiraki de l’« HAO-DEMETER » d’avoir accepté d’être examinateurs de ma thèse. J’adresse mes sincères remerciements au Pr. Nicolas Fabre de l’Université de Toulouse III Paul Sabatier et au Dr. Vincent Niderkorn de l’INRA Clermont-Ferrand, qui ont bien voulu faire partie de mon comité de thèse. Je les remercie pour leur intérêt pour mon travail, leurs conseils, disponibilité et leur appui permanent. Cette étude a pu être réalisée grâce à l’appui et à la collaboration de nombreuses personnes, tant en France qu’à l’étranger. Je tiens donc également à remercier : Le Pr. Juha-Pekka Salminen et la Pr. Maarit Karonen ensemble ainsi que leur équipe du travail pour m’avoir accueilli dans les laboratoires du « Natural Chemistry Research Group » de l’Université de Turku, Finlande. Merci pour m’avoir mené dans le fascinant monde des tanins. Je vous remercie tous pour votre aide, votre gentillesse, mais surtout l’inspiration et la motivation pendant mon stage dans cet extraordinaire pays. La Pr. Irene Mueller-Harvey de la « School of Agriculture, Policy and Development» de l’« Université de Reading », pour son soutien constant et des précieux temps qu’elle m’a dédiée, ainsi que toute la sagesse qu’elle m’a donnée pendant mon stage dans son laboratoire. Merci à l’équipe constituée par : Christos Fryganas, Honorata Ropiak, 2 QUIJADA J. 2015 Chaweewan Klongsiriwet, Parwin Majid (RIP), Mohammed Munis Dakheel, Christopher Drake et Prabhat Sakya pour toute l’aide, les conseils, et les bonheurs partagés pendant les deux mois où j’ai été avec eux. Je voudrais aussi remercier tous mes collègues étudiants de thèse « ESR (Early Stage Researcher) » du projet « LegumePlus », pour toutes les discussions, nos voyages en commun au travers de cet important projet de recherche, pour les moments partagés au long des réunions du projet et les divers cours de formation faits ensemble. Membres de l’équipe « Interaction Tanins-Nématodes Digestifs » présents au cours des trois dernières années, mes collègue et amis : Dr. Foteini Manolaraki, Dr. Blasius Azuhnwi, Dr. Aina Ramsay, Marine Rabeyrin, Audrey Torlotin, Lucie Legroux, Margaux Simon, Israel Chan-Pérez, Heloïse Legendre, Liza Bastide et M Eric Pardo. Très spécialement je voudrais remercier Elodie Gaudin, Ramzi El-Korso, Marica Engström et Liza Fonsou qui m’ont aide avec succès pour les études in vivo de cette thèse. Je tiens à vous remercier pour votre amitié et pour le temps passé ensemble à l'intérieur et à l'extérieur du laboratoire. Le Pr. Michel Franc et le personnel du département de Parasitologie de l’Ecole Nationale Vétérinaire de Toulouse pour m’avoir accompagnée au quotidien pendant ces années. Merci pour la cordialité et la gentillesse de chaque jour. Le Pr. François Schelcher et le personnel de l’UMR 1225 INRA/ENVT « Interactions Hôtes-Agents Pathogènes » pour leur sympathie et les services rendus et tout specialement d’avoir accepté d’être le président du jury de ma thèse. Les secrétaires de l’UMR 1225 INRA/ENVT : Pascale Fauré, Marie Perrin, Corinne Fabreguettes et Laurence Lecomte pour leur amitié et leur aide au niveau administratif et la chaleureuse cordialité qu’elles m’ont toutes montrée dès le premier jour à l’INRA. Les animaliers dont l’appui a été primordial pour la maintenance de nos animaux d’expérimentation, M Jean-Marc Delmas et toute l’équipe : Merci beaucoup! Je remercie aussi tous mes amis et tous mes proches qui, de près ou de loin, m’ont soutenue durant ma vie mais aussi spécialement pendant ces années de thèse. Enfin, notre travail de thèse a été réalisé grâce au soutien financier de : l’Union Européenne, grâce au projet Marie-Curie « LegumePlus » (Projet PITN-GA-2011-289377). Je voudrais aussi remercier la France, ce pays qui m'a reçu à bras ouverts. “A todos !Muchas gracias! estarán siempre en mi corazón”. (Merci beaucoup à tous, vous serez toujours dans mon cœur) 3 QUIJADA J. 2015 LISTE DES PUBLICATIONS Les différents travaux de recherche menés au cours de cette thèse ont fait l’objet des publications suivantes : Articles intégrés dans la thèse : Hoste, H., Torres-Acosta, J.F.J., Quijada, J., Chan Pérez, I., Dakheel, M.M., Kommuru, D.S., Quijada, J., Mueller-Harvey, I., Terrill, T.H. Interactions between Nutrition and Infections with H. contortus (and related Gastrointestinal Nematodes) in Small Ruminants. Adv. Parasit. (accepté). Quijada, J., Fryganas, C., Ropiak, H.M., Ramsay, A., Mueller-Harvey, I., Hoste, H. 2015. Anthelmintic activities against Haemonchus contortus or Trichostrongylus colubriformis from Small Ruminants are influenced by structural features of condensed tannins. J. Agric. Food Chem., 63, 6346–6354. Klongsiriwet, C., Quijada, J., Williams, A.R., Mueller-Harvey, I., Williamson, E.M., Hoste, H. 2015. Synergistic inhibition of Haemonchus contortus exsheathment by flavonoid monomers and condensed tannins. Int. J. Parasitol. Drugs Drug Resist., 5, 127–134. 4 QUIJADA J. 2015 LISTE DES ABREVIATIONS ADD Dérives d'amino-acetonitrile ADN Acide désoxyribonucléique AH Anthelminthique BZs Benzimidazoles Da(s) Daltons C Catéchol (catechin) CE50 Concentration efficace pour avoir le 50% d’effet EC Epicatéchol (epicatechin) EGC Epigallocatéchol (epigallocatechin) EGCG Epigallocatéchol gallaic (epigallocathechin gallate) g Gramme GABA Acide gamma aminobutyrique GC Gallocatéchol (gallocatechin) GCG Gallocatéchol gallaic (gallocathechin gallate) GI(s) Gastro-intestinal(aux) GIN(s) Nématodes gastro-intestinaux HCl Acide hydrochlorhydrique HPLC Chromatographie en phase liquide à haute performance Kg Kilogramme L1s Larves de stade 1 L2s Larves de stade 2 L3s Larves de stade 3 L4s Larves de stade 4 LEIA Méthode d'inhibition du dégainement larvaire LMIA Méthode d'inhibition de la migration larvaire mDP Degré moyen de polymérisation MS Matière sèche OH Hydroxyle OPG Œufs par gramme de fèces PC Procyanidol (procyanidin) PD Prodelphinidol (prodelphinidin) PEG Polyéthylène glycol PM Poids moléculaire PS Poids sec PSMs Métabolites secondaires des plantes PRPs Protéines riches en proline PVPP Polyvinyl polypyrrolidone SGIs Strongles gastro-intestinalaux TCs Tannins condensés THs Tannins hydrolysables TR Riche en tanin TTs Tannins totaux 5 QUIJADA J. 2015 TABLE DES MATIERES REMERCIEMENTS ................................................................................................ 2 LISTE DES PUBLICATIONS .................................................................................. 4 LISTE DES ABREVIATIONS ................................................................................. 5 TABLE DES MATIERES ......................................................................................... 6 RESUME ...........................................................................................................
Recommended publications
  • Flavonoid Glucodiversification with Engineered Sucrose-Active Enzymes Yannick Malbert
    Flavonoid glucodiversification with engineered sucrose-active enzymes Yannick Malbert To cite this version: Yannick Malbert. Flavonoid glucodiversification with engineered sucrose-active enzymes. Biotechnol- ogy. INSA de Toulouse, 2014. English. NNT : 2014ISAT0038. tel-01219406 HAL Id: tel-01219406 https://tel.archives-ouvertes.fr/tel-01219406 Submitted on 22 Oct 2015 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. Last name: MALBERT First name: Yannick Title: Flavonoid glucodiversification with engineered sucrose-active enzymes Speciality: Ecological, Veterinary, Agronomic Sciences and Bioengineering, Field: Enzymatic and microbial engineering. Year: 2014 Number of pages: 257 Flavonoid glycosides are natural plant secondary metabolites exhibiting many physicochemical and biological properties. Glycosylation usually improves flavonoid solubility but access to flavonoid glycosides is limited by their low production levels in plants. In this thesis work, the focus was placed on the development of new glucodiversification routes of natural flavonoids by taking advantage of protein engineering. Two biochemically and structurally characterized recombinant transglucosylases, the amylosucrase from Neisseria polysaccharea and the α-(1→2) branching sucrase, a truncated form of the dextransucrase from L. Mesenteroides NRRL B-1299, were selected to attempt glucosylation of different flavonoids, synthesize new α-glucoside derivatives with original patterns of glucosylation and hopefully improved their water-solubility.
    [Show full text]
  • IN SILICO ANALYSIS of FUNCTIONAL Snps of ALOX12 GENE and IDENTIFICATION of PHARMACOLOGICALLY SIGNIFICANT FLAVONOIDS AS
    Tulasidharan Suja Saranya et al. Int. Res. J. Pharm. 2014, 5 (6) INTERNATIONAL RESEARCH JOURNAL OF PHARMACY www.irjponline.com ISSN 2230 – 8407 Research Article IN SILICO ANALYSIS OF FUNCTIONAL SNPs OF ALOX12 GENE AND IDENTIFICATION OF PHARMACOLOGICALLY SIGNIFICANT FLAVONOIDS AS LIPOXYGENASE INHIBITORS Tulasidharan Suja Saranya, K.S. Silvipriya, Manakadan Asha Asokan* Department of Pharmaceutical Chemistry, Amrita School of Pharmacy, Amrita Viswa Vidyapeetham University, AIMS Health Sciences Campus, Kochi, Kerala, India *Corresponding Author Email: [email protected] Article Received on: 20/04/14 Revised on: 08/05/14 Approved for publication: 22/06/14 DOI: 10.7897/2230-8407.0506103 ABSTRACT Cancer is a disease affecting any part of the body and in comparison with normal cells there is an elevated level of lipoxygenase enzyme in different cancer cells. Thus generation of lipoxygenase enzyme inhibitors have suggested being valuable. Individual variation was identified by the functional effects of Single Nucleotide Polymorphisms (SNPs). 696 SNPs were identified from the ALOX12 gene, out of which 73 were in the coding non-synonymous region, from which 8 were found to be damaging. In silico analysis was performed to determine naturally occurring flavonoids such as isoflavones having the basic 3- phenylchromen-4-one skeleton for the pharmacological activity, like Genistein, Diadzein, Irilone, Orobol and Pseudobaptigenin. O-methylated isoflavones such as Biochanin, Calycosin, Formononetin, Glycitein, Irigenin, 5-O-Methylgenistein, Pratensein, Prunetin, ψ-Tectorigenin, Retusin and Tectorigenine were also used for the study. Other natural products like Aesculetin, a coumarin derivative; flavones such as ajoene and baicalein were also used for the comparative study of these natural compounds along with acteoside and nordihydroguaiaretic acid (antioxidants) and active inhibitors like Diethylcarbamazine, Zileuton and Azelastine as standard for the computational analysis.
    [Show full text]
  • Revisiting Greek Propolis: Chromatographic Analysis and Antioxidant Activity Study
    RESEARCH ARTICLE Revisiting Greek Propolis: Chromatographic Analysis and Antioxidant Activity Study Konstantinos M. Kasiotis1*, Pelagia Anastasiadou1, Antonis Papadopoulos2, Kyriaki Machera1* 1 Benaki Phytopathological Institute, Department of Pesticides Control and Phytopharmacy, Laboratory of Pesticides' Toxicology, Kifissia, Athens, Greece, 2 Benaki Phytopathological Institute, Department of Phytopathology, Laboratory of Non-Parasitic Diseases, Kifissia, Athens, Greece * [email protected] (KMK); [email protected] (KM) Abstract a1111111111 Propolis is a bee product that has been extensively used in alternative medicine and recently a1111111111 a1111111111 has gained interest on a global scale as an essential ingredient of healthy foods and cosmet- a1111111111 ics. Propolis is also considered to improve human health and to prevent diseases such as a1111111111 inflammation, heart disease, diabetes and even cancer. However, the claimed effects are anticipated to be correlated to its chemical composition. Since propolis is a natural product, its composition is consequently expected to be variable depending on the local flora align- ment. In this work, we present the development of a novel HPLC-PDA-ESI/MS targeted OPEN ACCESS method, used to identify and quantify 59 phenolic compounds in Greek propolis hydroalco- holic extracts. Amongst them, nine phenolic compounds are herein reported for the first time Citation: Kasiotis KM, Anastasiadou P, Papadopoulos A, Machera K (2017) Revisiting in Greek propolis. Alongside GC-MS complementary analysis was employed, unveiling Greek Propolis: Chromatographic Analysis and eight additional newly reported compounds. The antioxidant activity study of the propolis Antioxidant Activity Study. PLoS ONE 12(1): samples verified the potential of these extracts to effectively scavenge radicals, with the e0170077. doi:10.1371/journal.pone.0170077 extract of Imathia region exhibiting comparable antioxidant activity to that of quercetin.
    [Show full text]
  • 2.1 Structure Elucidation 14 2.2 Synthesis 15
    , HIERDIE EKSEMPlAAR MAG ONDER University Free State GEEN OMSTANDIGHEDE UIT DIE mml~lmmMMllllllln34300000347405 Universiteit Vrystaat BIBLIOTEEK VER\VYDER WORD NIE THE STRUCTURE AND SYNTHESIS OF OLIGOFLA VANOIDS AND OLIGOSTILBENES FROM CASSIA ABBREVIATA. Dissertation submitted infulfilment of the requirements for the degree Master of Science in the Department of Chemisrty Faculty of Natural Sciences at University of Orange Free State Bloemfontein by Makhosazana Claribel Mthembu Supervisor: Prof. E. Malan Co-supervisor Dr J. C. Coetzee JANUARY 2000 ACKNOWLEDGEMENTS I wish to express my gratitude to the following people: • God the Almighty for the love and support he has shown me throughout my studies. • My supervisors Professor f. Malan and Dr j. C. Coetzee, their guidance and helpful recommendations throughout this study will always be appreciated: • • Proff. Malan for his constructive guidance, critism and invaluable support in putting this work in paper. • Dr j. C. Coetzeefor recording my NMR spectra, his encourangement and unselfish assistance. • Proff. V. Brandt ,D. Ferrdra and NRF sponsor for granting me this opportumity. • Finally the members of the fomily and [riends, Irene,jaqui, Zanele, Vusl and Busi for their love, tolerance and constant encouragement, I owe the greatest debt to them. M. C. Mthembu Table of Content Abstract LITERATURE SURVERY CHAPTER 1: MONOMERIC STILBENES 1 1.1 Nomenclature 1 1.2 Structure and Natural Occurrence 3 1.3 Structure Elucidation 5 1.4 Synthesis 5 CHAPTER 2: OLIGOMERIC STILBENES 11 2.1 Structure Elucidation 14 2.2 Synthesis 15 CHAPTER 3.: FLA VAN-3-0LS 16 3.1 Nomenclature 16 3.2 Structure and Natural Occurrence 17 3.3 Structure Elucidation 19 CHAPTER 4: LEUCOANTHOCY ANIDINS.
    [Show full text]
  • (12) Patent Application Publication (10) Pub. No.: US 2011/0268722 A1 Siegelin Et Al
    US 20110268722A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2011/0268722 A1 Siegelin et al. (43) Pub. Date: Nov. 3, 2011 (54) COMBINATION THERAPIES WITH Publication Classification MTOCHONORAL-TARGETED (51) Int. Cl ANT-TUMIORAGENTS A638/17 (2006.01) CI2N 5/071 (2010.01) (76) Inventors: Markus D. Siegelin, Weehawken, A6IP35/00 (2006.01) NJ (US); Dario C. Altieri, A 6LX 39/395 (2006.01) Worcester, MA (US) C07D 225/06 (2006.01) (52) U.S. Cl. ..................... 424/130.1; 514/18.9; 540/461; (21) Appl. No.: 13/092,475 435/375 (57) ABSTRACT (22) Filed: Apr. 22, 2011 Described are mitochondria-targeted anti-tumor agents, death receptor agonists, autophagy inhibitors, and NF-KB Related U.S. Application Data signaling pathway inhibitors, and methods of making and (60) Provisional application No. 61/326,872, filed on Apr. using the same for the treatment of disorders associated with 22, 2010. unwanted cell proliferation. Patent Application Publication Nov. 3, 2011 Sheet 1 of 13 US 2011/0268722 A1 120% 8: 8: 8 CE 60% : 5 P_GA s : RA 2:: : P-GA-RA : : 8 N3 FAS Figure 1A Patent Application Publication Nov. 3, 2011 Sheet 2 of 13 US 2011/0268722 A1 igure 1B ---, igure 2A Figure 2B Patent Application Publication Nov. 3, 2011 Sheet 3 of 13 US 2011/0268722 A1 8. s::::::: se: -83.383.3 ---sixxxxx:----- --~~~x-x-x-xxii. : s: 8 i88 s: sig ::::::: ...i Figure 2C Figure 2D Figure 3A Figure 3B Patent Application Publication Nov. 3, 2011 Sheet 4 of 13 US 2011/0268722 A1 ::: :*:: & : : isix; {S3.g3-8 : Exx8:8-3 : {kari 333333.
    [Show full text]
  • Phylogenetic Insights on the Isoflavone Profile Variations In
    Food Research International 76 (2015) 51–57 Contents lists available at ScienceDirect Food Research International journal homepage: www.elsevier.com/locate/foodres Phylogenetic insights on the isoflavone profile variations in Fabaceae spp.: Assessment through PCA and LDA Tatiana Visnevschi-Necrasov a,b, João C.M. Barreira b,c,⁎,SaraC.Cunhab, Graça Pereira d, Eugénia Nunes a, M. Beatriz P.P. Oliveira b a CIBIO-ICETA, Faculdade de Ciências, Universidade do Porto, R. Padre Armando Quintas 4485-661 Vairão, Portugal b REQUIMTE, Departamento de Ciências Químicas, Faculdade de Farmácia, Universidade do Porto, Rua Jorge Viterbo Ferreira, No. 228, 4050-313, Porto,Portugal c CIMO-ESA, Instituto Politécnico de Bragança, Campus de Santa Apolónia, Apartado 1172, 5301-855 Bragança, Portugal d INRB/IP — INIA — Instituto Nacional de Recursos Biológicos, Caia E São Pedro Estrada Gil Vaz, 7350-228 Elvas, Portugal article info abstract Article history: Legumes (Fabaceae) are important crops, known as sources of food, feed for livestock and raw materials for in- Received 30 September 2014 dustry. Their ability to capture atmospheric nitrogen during symbiotic processes with soil bacteria reduces the Received in revised form 15 November 2014 need for expensive chemical fertilizers, improving soil and water quality. Several Fabaceae species are acknowl- Accepted 20 November 2014 edged for the high levels of secondary metabolites. Isoflavones are among the most well-known examples of Available online 28 November 2014 these compounds, being recognized for their several types of biological activity. Herein, isoflavone profiles were characterized in nine species of four Fabaceae genera (Biserrula, Lotus, Ornithopus and Scorpiurus). Plants Chemical compounds studied in this article: fl Daidzin (PubChem CID: 107971) were harvested in the late ower physiological stage to prevent biased results due to naturally occurring varia- Genistin (PubChem CID: 5281377) tions along the vegetative cycle.
    [Show full text]
  • Polymerization Degrees, Molecular Weights and Protein-Binding Affinities of Condensed Tannin Fractions from a Leucaena Leucocephala Hybrid
    Molecules 2014, 19, 7990-8010; doi:10.3390/molecules19067990 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Polymerization Degrees, Molecular Weights and Protein-Binding Affinities of Condensed Tannin Fractions from a Leucaena leucocephala Hybrid Mookiah Saminathan 1, Hui Yin Tan 2, Chin Chin Sieo 1,3, Norhani Abdullah 3,4, Clemente Michael Vui Ling Wong 5, Emilia Abdulmalek 6 and Yin Wan Ho 1,* 1 Institute of Bioscience, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; E-Mails: [email protected] (M.S.); [email protected] (C.C.S.) 2 Faculty of Applied Sciences and Computing, Tunku Abdul Rahman University College, 53300 Kuala Lumpur, Malaysia; E-Mail: [email protected] 3 Faculty of Biotechnology and Biomolecular Sciences, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; E-Mail: [email protected] 4 Institute of Tropical Agriculture, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia 5 Biotechnology Research Institute, Universiti Malaysia Sabah, Jalan UMS, 88400 Kota Kinabalu, Sabah, Malaysia; E-Mail: [email protected] 6 Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor, Malaysia; E-Mail: [email protected] * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +603-8947-2161; Fax: +603-8947-2101. Received: 18 March 2014; in revised form: 11 May 2014 / Accepted: 21 May 2014 / Published: 12 June 2014 Abstract: Condensed tannins (CTs) form insoluble complexes with proteins and are able to protect them from degradation, which could lead to rumen bypass proteins. Depending on their degrees of polymerization (DP) and molecular weights, CT fractions vary in their capability to bind proteins.
    [Show full text]
  • WO 2011/086458 Al
    (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date _ . ... _ 21 July 2011 (21.07.2011) WO 2011/086458 Al (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every A61L 27/20 (2006.01) A61L 27/54 (2006.01) kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BR, BW, BY, BZ, (21) International Application Number: CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, DO, PCT/IB20 11/000052 DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (22) International Filing Date: HN, HR, HU, ID, IL, IN, IS, JP, KE, KG, KM, KN, KP, 13 January 201 1 (13.01 .201 1) KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, (25) Filing Language: English NO, NZ, OM, PE, PG, PH, PL, PT, RO, RS, RU, SC, SD, (26) Publication Language: English SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, ZW. (30) Priority Data: 12/687,048 13 January 2010 (13.01 .2010) US (84) Designated States (unless otherwise indicated, for every 12/714,377 26 February 2010 (26.02.2010) US kind of regional protection available): ARIPO (BW, GH, 12/956,542 30 November 2010 (30.1 1.2010) us GM, KE, LR, LS, MW, MZ, NA, SD, SL, SZ, TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, MD, RU, TJ, (71) Applicant (for all designated States except US): AL- TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, LERGAN INDUSTRIE, SAS [FR/FR]; Route de EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, Promery, Zone Artisanale de Pre-Mairy, F-74370 Pringy LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, (FR).
    [Show full text]
  • Ep 3138585 A1
    (19) TZZ¥_¥_T (11) EP 3 138 585 A1 (12) EUROPEAN PATENT APPLICATION (43) Date of publication: (51) Int Cl.: 08.03.2017 Bulletin 2017/10 A61L 27/20 (2006.01) A61L 27/54 (2006.01) A61L 27/52 (2006.01) (21) Application number: 16191450.2 (22) Date of filing: 13.01.2011 (84) Designated Contracting States: (72) Inventors: AL AT BE BG CH CY CZ DE DK EE ES FI FR GB • Gousse, Cecile GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO 74230 Dingy Saint Clair (FR) PL PT RO RS SE SI SK SM TR • Lebreton, Pierre Designated Extension States: 74000 Annecy (FR) BA ME •Prost,Nicloas 69440 Mornant (FR) (30) Priority: 13.01.2010 US 687048 26.02.2010 US 714377 (74) Representative: Hoffmann Eitle 30.11.2010 US 956542 Patent- und Rechtsanwälte PartmbB Arabellastraße 30 (62) Document number(s) of the earlier application(s) in 81925 München (DE) accordance with Art. 76 EPC: 15178823.9 / 2 959 923 Remarks: 11709184.3 / 2 523 701 This application was filed on 29-09-2016 as a divisional application to the application mentioned (71) Applicant: Allergan Industrie, SAS under INID code 62. 74370 Pringy (FR) (54) STABLE HYDROGEL COMPOSITIONS INCLUDING ADDITIVES (57) The present specification generally relates to hydrogel compositions and methods of treating a soft tissue condition using such hydrogel compositions. EP 3 138 585 A1 Printed by Jouve, 75001 PARIS (FR) EP 3 138 585 A1 Description CROSS REFERENCE 5 [0001] This patent application is a continuation-in-part of U.S.
    [Show full text]
  • PDF-Document
    Supplementary Materials 1 Metabolomics profiling analysis of red clover Table S1. Compound identification of red clover in positive and negative ion modes. MS1 No RT Ion Ion Measur Predicte Ste Le Flow Err MS2 MS3 Identification . min Form Formula ed d m af er ppm m/z m/z [M − 195.050 1 1.43 C6H11O7 195.0499 2.82 Gluconic acid ++ ++ +++ H]- 5 179.03506(C9H7O4); Benzoylcitronensa [M − 295.045 295.0448 ++ 2 4.46 C13H11O8 0.67 133.01451(C4H5O5); [295-179]135.04524(C8H7O2); ure ++ +++ H]- 0 4 + 115.00400(C4H3O4); [M + 355.102 ++ 3 5.42 C16H19O9 355.1024 1.21 chlorogenic acid + +++ H]+ 8 + [433-271]253.04956(C15H9O4); 243.06529(C14H11O4); [M + 433.111 Genistein- ++ 4 6.60 C21H21O10 433.1129 −3.54 271.06067(C15H11O5); 215.07042(C13H11O3); +++ +++ H]+ 4 glucoside + 153.01839(C7H5O4); 149.02335(C8H5O3); [M + 417.117 5 6.71 C21H21O9 417.1180 −2.34 239.07021(C15H11O3) daidzin + ++ +++ H]+ 0 [M + 447.127 calycosin-7-O-β-D- ++ 6 7.20 C22H23O10 447.1286 −1.91 269.08072(C16H13O4) +++ +++ H]+ 7 glucoside + 1 [533-285]270.05258(C15H10O5); Calycosin-7-O-β- [M + 533.127 253.04982(C15H9O4); ++ 7 8.03 C25H25O13 533.1290 −3.54 285.07642(C16H13O5); D-glucoside 4′′-O- +++ +++ H]+ 1 225.05478(C14H9O3); + malonate 137.02333(C7H5O3); [M + 433.112 ++ 8 8.95 C21H21O10 433.1129 −2.11 255.06516(C15H11O4) genistin ++ +++ H]+ 0 + [519-271]253.04958(C15H9O4,); Genistein- 243.06526(C14H11O4); [M + 519.111 433.11377(C21H21O10); glucoside ++ 9 9.31 C24H23O13 519.1133 −3.25 215.07045(C13H11O3); - +++ H]+ 6 271.06073(C15H11O5); malonate + 153.01833(C7H5O4); 149.02333(C8H5O3);
    [Show full text]
  • 48003 Hughes Et Al 2017 Accepted Version.Pdf
    ResearchOnline@JCU This is the Accepted Version of a paper published in the Journal: Critical Reviews in Food Science and Nutrition Hughes, Samuel D., Ketheesan, Natkunam, and Haleagrahara, Nagaraja (2017) The therapeutic potential of plant flavonoids on rheumatoid arthritis. Critical Reviews in Food Science and Nutrition, 57 (17). pp. 3601-3613. http://dx.doi.org/10.1080/10408398.2016.1246413 © 2015. This manuscript version is made available under the CC-BY-NC-ND 4.0 license http://creativecommons.org/licenses/by-nc-nd/4.0/ Critical Reviews in Food Science and Nutrition ISSN: 1040-8398 (Print) 1549-7852 (Online) Journal homepage: http://www.tandfonline.com/loi/bfsn20 The Therapeutic Potential of Plant Flavonoids on Rheumatoid Arthritis Samuel D. Hughes, Natkunam Ketheesan & Nagaraja Haleagrahara To cite this article: Samuel D. Hughes, Natkunam Ketheesan & Nagaraja Haleagrahara (2016): The Therapeutic Potential of Plant Flavonoids on Rheumatoid Arthritis, Critical Reviews in Food Science and Nutrition, DOI: 10.1080/10408398.2016.1246413 To link to this article: http://dx.doi.org/10.1080/10408398.2016.1246413 Accepted author version posted online: 22 Nov 2016. Submit your article to this journal Article views: 122 View related articles View Crossmark data Full Terms & Conditions of access and use can be found at http://www.tandfonline.com/action/journalInformation?journalCode=bfsn20 Download by: [JAMES COOK UNIVERSITY] Date: 23 March 2017, At: 16:37 ACCEPTED MANUSCRIPT The Therapeutic Potential of Plant Flavonoids on Rheumatoid Arthritis Samuel D. Hughes1, Natkunam Ketheesan2 & Nagaraja Haleagrahara3,* 1,2,3Biomedicine, College of Public Health, Medical & Veterinary Sciences, and 2, 3Australian Institute of Tropical Health and Medicine (AITHM), James Cook University, Townsville, Australia *Address correspondence to: Nagaraja Haleagrahara, Biomedicine, College of Public Health, Medical & Veterinary Sciences, James Cook University, Townsville, Australia.
    [Show full text]
  • Supplementary Files
    Supplementary Files Table S1. Calibration curves, detection limits and quantification limits for the twelve investigated components (n = 6) of B. chinensis. Analyte Calibration Curve R2 (n = 6) Linear Range (μg/mL) Neomangiferin y = 28.17x + 2.68 0.9999 0.27–55.00 Mangiferin y = 20.76x − 6.51 0.9990 0.35–70.40 Tectoridin y = 94.19x − 37.26 0.9998 3.86–154.50 Iristectorin B y = 82.51x − 10.64 0.9999 1.65–66.00 Iristectorin A y = 49.80x − 43.19 0.9992 1.10–110.00 Iridin y = 60.23x − 11.30 0.9999 1.06–159.00 Tectorigenin y = 95.28x+25.32 0.9999 0.27–108.50 Iristectorigenin A y = 56.82x − 4.84 0.9999 0.16–16.20 Irigenin y = 109.93x + 5.03 0.9998 0.83–41.60 Irisflorentin y = 123.90x − 0.19 0.9993 0.23–11.70 Irilone y = 146.93x − 2.92 0.9992 0.11–4.40 Dictomitin y = 18.20x − 1.47 0.9991 0.59–17.70 y, peak area; x, the concentration of each reference compound (μg/mL). Table S2-1. The data of rhizome of B. chinensis in G1 from different sampling points at 40 °C. a Drying Time (min) T. b Analytes 0 120 240 360 480 600 Moist. c 63.24 ± 0.21 42.31 ± 0.23 27.25 ± 0.06 20.14 ± 0.10 12.04 ± 0.13 8.13 ± 0.06 1 d 2.10 ± 0.07 0.95 ± 0.00 0.50 ± 0.11 1.37 ± 0.00 1.11 ± 0.07 1.17 ± 0.10 2 d 1.84 ± 0.03 1.02 ± 0.01 0.77 ± 0.06 1.20 ± 0.08 1.03 ± 0.05 1.23 ± 0.06 3 d 12.85 ± 0.06 11.12 ± 0.03 10.55 ± 0.03 15.58 ± 0.13 14.36 ± 0.13 14.17 ± 0.04 4 d 1.89 ± 0.12 1.41 ± 0.04 1.19 ± 0.04 2.00 ± 0.08 1.72 ± 0.02 1.83 ±0.02 5 d 6.14 ± 0.03 5.42 ± 0.02 4.72 ± 0.07 6.94 ± 0.10 6.59 ± 0.01 7.74 ± 0.15 40 °C 6 d 7.16 ± 0.03 5.33 ± 0.26 5.25 ± 0.01 7.41 ± 0.17 6.34 ±
    [Show full text]