WO 2017/211683 Al 14 December 2017 (14.12.2017) W !P O PCT
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Metabolic Engineering of Microbial Cell Factories for Biosynthesis of Flavonoids: a Review
molecules Review Metabolic Engineering of Microbial Cell Factories for Biosynthesis of Flavonoids: A Review Hanghang Lou 1,†, Lifei Hu 2,†, Hongyun Lu 1, Tianyu Wei 1 and Qihe Chen 1,* 1 Department of Food Science and Nutrition, Zhejiang University, Hangzhou 310058, China; [email protected] (H.L.); [email protected] (H.L.); [email protected] (T.W.) 2 Hubei Key Lab of Quality and Safety of Traditional Chinese Medicine & Health Food, Huangshi 435100, China; [email protected] * Correspondence: [email protected]; Tel.: +86-0571-8698-4316 † These authors are equally to this manuscript. Abstract: Flavonoids belong to a class of plant secondary metabolites that have a polyphenol structure. Flavonoids show extensive biological activity, such as antioxidative, anti-inflammatory, anti-mutagenic, anti-cancer, and antibacterial properties, so they are widely used in the food, phar- maceutical, and nutraceutical industries. However, traditional sources of flavonoids are no longer sufficient to meet current demands. In recent years, with the clarification of the biosynthetic pathway of flavonoids and the development of synthetic biology, it has become possible to use synthetic metabolic engineering methods with microorganisms as hosts to produce flavonoids. This article mainly reviews the biosynthetic pathways of flavonoids and the development of microbial expression systems for the production of flavonoids in order to provide a useful reference for further research on synthetic metabolic engineering of flavonoids. Meanwhile, the application of co-culture systems in the biosynthesis of flavonoids is emphasized in this review. Citation: Lou, H.; Hu, L.; Lu, H.; Wei, Keywords: flavonoids; metabolic engineering; co-culture system; biosynthesis; microbial cell factories T.; Chen, Q. -
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. -
Modification Et Stabilisation De La Réactivité De
Modification et stabilisation de la réactivité de tanins traités chimiquement : applications à la préparation de résines adhésives et de mousses écosoutenables Samuele Giovando To cite this version: Samuele Giovando. Modification et stabilisation de la réactivité de tanins traités chimiquement : applications à la préparation de résines adhésives et de mousses écosoutenables. Alimentation et Nutrition. Université de Lorraine, 2013. Français. NNT : 2013LORR0227. tel-01750522 HAL Id: tel-01750522 https://hal.univ-lorraine.fr/tel-01750522 Submitted on 29 Mar 2018 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. AVERTISSEMENT Ce document est le fruit d'un long travail approuvé par le jury de soutenance et mis à disposition de l'ensemble de la communauté universitaire élargie. Il est soumis à la propriété intellectuelle de l'auteur. Ceci implique une obligation de citation et de référencement lors de l’utilisation de ce document. D'autre part, toute contrefaçon, plagiat, reproduction illicite encourt une poursuite pénale. Contact : [email protected] LIENS Code de la Propriété Intellectuelle. articles L 122. 4 Code de la Propriété Intellectuelle. articles L 335.2- L 335.10 http://www.cfcopies.com/V2/leg/leg_droi.php http://www.culture.gouv.fr/culture/infos-pratiques/droits/protection.htm UFR. -
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. -
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. -
Condensed Tannins 7
120 Biochem. J. (1961) 78, 120 Condensed Tannins 7. ISOLATION OF (-)-7:3':4'-TRIHYDROXYFLAVAN-3-OL [(-)-FISETINIDOL], A NATURALLY OCCURRING CATECHIN FROM BLACK-WATTLE HEARTWOOD* By D. G. ROUX AND E. PAULUS Leather Industries Research Institute, Rhodes University, Grahamstown, South Africa (Received 9 May 1960) The interrelated flavonoid compounds (+ )- aqueous phase extracted with ethyl acetate in each in- 7:3':4'-trihydroxyflavan-3:4-diol (Keppler, 1957) stance. The combined organic and ethyl acetate extracts of 2:3-trans:3:4-cis configuration (Clark-Lewis & from each fraction were evaporated to 50 ml. and applied Roux, 1959), (+ )-fustin (2:3-trans) and in bands to sheets (5 ml./sheet) of 221 in. x 18j in. What- 1958, man no. 3 chromatographic paper. The chromatograms fisetin (Roux & Paulus, 1960) have been isolated were developed by upward migration in 2 % acetic acid for from black-wattle-wood tannins. In the present 12 hr. The fustin (RF 0-43 on Whatman no. 3 paper), the study a new catechin, (-)-fisetinidol, correspond- polymeric leuco-fisetinidin and the ( +)-mollisacacidin ing to these substances has been isolated, and their (traces) (RF 0 57) bands were located with toluene-p- biogenesis is discussed. sulphonic acid. Bands in the region Rp 050 which appeared yellowish in ordinary light were cut out and eluted with 70% ethanol. Concentrate of the eluents gave 0-113 g. of EXPERIMENTAL AND RESULTS pale-yellow crystals. The mother liquors were purified by All melting points are uncorrected. Mixed melting running on five sheets, as above, yielding a further 0-05 g. points were on equimolecular mixtures of the substances Pale-yellow crystals of (- )-fisetinidol, m.p. -
Different Approaches to Evaluate Tannin Content and Structure of Selected Plant Extracts – Review and New Aspects M
View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by JKI Open Journal Systems (Julius Kühn-Institut) Journal of Applied Botany and Food Quality 86, 154 - 166 (2013), DOI:10.5073/JABFQ.2013.086.021 1University of Kiel, Institute of Crop Science and Plant Breeding – Grass and Forage Science / Organic Agriculture, Kiel, Germany 2Institute of Ecological Chemistry, Plant Analysis and Stored Product Protection; Julius Kühn-Institute, Quedlinburg, Germany Different approaches to evaluate tannin content and structure of selected plant extracts – review and new aspects M. Kardel1*, F. Taube1, H. Schulz2, W. Schütze2, M. Gierus1 (Received July 2, 2013) Summary extracts, tannins, salts and derivates was imported to the EU in the year 2011, mainly from Argentina, with a trade value of nearly Tannins occur in many field herbs and legumes, providing an im- 63.5 mio. US Dollar (UN-COMTRADE, 2013). These extracts are pro- mense variability in structure and molecular weight. This leads to duced industrially on a large scale. They could therefore maintain complications when measuring tannin content; comparability of a relatively constant quality and thus provide an advantage in rumi- different methods is problematic. The present investigations aimed at nant feeding. characterizing four different tannin extracts: quebracho (Schinopsis Tannins from different sources can react very diverse regarding lorentzii), mimosa (Acacia mearnsii), tara (Caesalpinia spinosa), protein affinity (MCNABB et al., 1998; BUENO et al., 2008). Diffe- and gambier (Uncaria gambir) and impact of storage conditions. rences in tannin structure can occur even between similar plant Using photometrical methods as well as HPLC-ESI-MS, fundamen- species (OSBORNE and MCNEILL, 2001; HATTAS et al., 2011) and a tal differences could be determined. -
Pharmaceutical Appendix to the Tariff Schedule 2
Harmonized Tariff Schedule of the United States (2007) (Rev. 2) Annotated for Statistical Reporting Purposes PHARMACEUTICAL APPENDIX TO THE HARMONIZED TARIFF SCHEDULE Harmonized Tariff Schedule of the United States (2007) (Rev. 2) Annotated for Statistical Reporting Purposes PHARMACEUTICAL APPENDIX TO THE TARIFF SCHEDULE 2 Table 1. This table enumerates products described by International Non-proprietary Names (INN) which shall be entered free of duty under general note 13 to the tariff schedule. The Chemical Abstracts Service (CAS) registry numbers also set forth in this table are included to assist in the identification of the products concerned. For purposes of the tariff schedule, any references to a product enumerated in this table includes such product by whatever name known. ABACAVIR 136470-78-5 ACIDUM LIDADRONICUM 63132-38-7 ABAFUNGIN 129639-79-8 ACIDUM SALCAPROZICUM 183990-46-7 ABAMECTIN 65195-55-3 ACIDUM SALCLOBUZICUM 387825-03-8 ABANOQUIL 90402-40-7 ACIFRAN 72420-38-3 ABAPERIDONUM 183849-43-6 ACIPIMOX 51037-30-0 ABARELIX 183552-38-7 ACITAZANOLAST 114607-46-4 ABATACEPTUM 332348-12-6 ACITEMATE 101197-99-3 ABCIXIMAB 143653-53-6 ACITRETIN 55079-83-9 ABECARNIL 111841-85-1 ACIVICIN 42228-92-2 ABETIMUSUM 167362-48-3 ACLANTATE 39633-62-0 ABIRATERONE 154229-19-3 ACLARUBICIN 57576-44-0 ABITESARTAN 137882-98-5 ACLATONIUM NAPADISILATE 55077-30-0 ABLUKAST 96566-25-5 ACODAZOLE 79152-85-5 ABRINEURINUM 178535-93-8 ACOLBIFENUM 182167-02-8 ABUNIDAZOLE 91017-58-2 ACONIAZIDE 13410-86-1 ACADESINE 2627-69-2 ACOTIAMIDUM 185106-16-5 ACAMPROSATE 77337-76-9 -
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. -
1. Introduction
1. Introduction 1.1-General approach Natural products are compounds produced by living organisms and include both small and macromolecules. All of these compounds are derived biosynthetically, from precursors called primary metabolites, which include amino acids, carbohydrate, and fatty acids.These metabolites are considered to be building blocks of life and are necessary for regular cellular functions. Some of the small molecular do not have a clearly defined function. They are considered secondary metabolites and make up the majority of work on natural products. Secondary metabolites are generally considered to be specific. 1 Flavonoids are phenolic substances is isolated from a wide range of vascular plant.There are more than 8150 different flavonoids have been reported 2.Flavonoids are located inside the cell or in the surface of the various functions of plants 3.They act in the plants as antioxidants, antimicrobials, photoreceptors, visual attractors, feeding repellents and for light screening 4.Many studies have shown that flavonoids exhibit biological and pharmacological activities, including antioxidant ,cytotoxic, anticancer ,antiviral ,antibacterial, cardioprotetive, neuroprotective ,antimalarial, antileshmanial ,antitrypanosomal and antiambebial properties 5 . 1 These biological and pharmacological properties are usually attributed to their free radicals scavenging efficacies, metal complexion capabilities, and their ability to bind to proteins with a high degree of specificity 6. The basic flavonoid structure contain the flavones nucleus which consist of 15 carbons atoms derived from a C6-C3-C6 skeleton .Flavonoid skeleton is composed of two aromatic rings (commonly designated as A and B) which are linked by three carbon chain the connecting carbon chain which combines with an oxygen to form a heterocyclic central or C ring for most flavonoids with the exception of chalcones-2 in which the carbon chain between the A and B ring is linear 7. -
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. -
Condensed Tannins in Tropical Forage Legumes: Their Characterisation and Study of Their Nutritional Impact from the Standpoint of Structure-Activity
The University of Reading Condensed tannins in tropical forage legumes: their characterisation and study of their nutritional impact from the standpoint of structure-activity relationships By Rolando Barahona Rosales B.S. (Kansas State University, 1992) M.Sc. (Kansas State University, 1995) A thesis submitted for the degree of Doctor of Philosophy Department of Agriculture, The University of Reading July 1999 SOLANGE, SAMUEL, SANTIAGO and ISABELA: Contar con ustedes ha sido la bendicion mas grande de mi vida. En esta y en las futuras obras de mi vida se los encontrara a Uds. como mi inagotable fuente de inspiracion. i ACKNOWLEDGEMENTS This thesis is the culmination of a long-held dream, that started in the days I was attending the John F. Kennedy School of Agriculture at San Francisco, Atlantida, Honduras. There, and throughout my days as a student at Kansas State University, my daily interactions with friends and professors kept alive and nurtured those aspirations. Undoubtedly, the number of persons and institutions to whom I am indebted for the completion of my PhD career is enormous. I would have not advanced so far into this journey, however, without the encouragement and inspiration provided by my parents, sisters and brothers, who never made a secret of their satisfaction for my chosen career. Throughout my PhD studies, I was fortunate to receive advice and supervision from four great individuals: At the Centro Internacional de Agricultura Tropical (CIAT) in Cali, Colombia, I received supervision and most invaluably, friendship from Dr. Carlos Lascano. Ever since we met in 1994, Carlos and I have shared the desire to understand the true impact of tannins in ruminant nutrition.