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Bacterial Hosts for Production of Bioactive Phenolics from Berry Fruits

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University of Groningen BacHBerry Dudnik, Alexey; Almeida, A. Filipa; Andrade, Ricardo; Avila, Barbara; Banados, Pilar; Barbay, Diane; Bassard, Jean-Etienne; Benkoulouche, Mounir; Bott, Michael; Braga, Adelaide Published in: Phytochemistry reviews DOI: 10.1007/s11101-017-9532-2 IMPORTANT NOTE: You are advised to consult the publisher's version (publisher's PDF) if you wish to cite from it. Please check the document version below. Document Version Publisher's PDF, also known as Version of record Publication date: 2018 Link to publication in University of Groningen/UMCG research database Citation for published version (APA): Dudnik, A., Almeida, A. F., Andrade, R., Avila, B., Banados, P., Barbay, D., ... Solopova, A. (2018). BacHBerry: BACterial Hosts for production of Bioactive phenolics from bERRY fruits. Phytochemistry reviews, 17(2), 291-326. https://doi.org/10.1007/s11101-017-9532-2 Copyright Other than for strictly personal use, it is not permitted to download or to forward/distribute the text or part of it without the consent of the author(s) and/or copyright holder(s), unless the work is under an open content license (like Creative Commons). Take-down policy If you believe that this document breaches copyright please contact us providing details, and we will remove access to the work immediately and investigate your claim. Downloaded from the University of Groningen/UMCG research database (Pure): http://www.rug.nl/research/portal. For technical reasons the number of authors shown on this cover page is limited to 10 maximum. Download date: 12-11-2019 Phytochem Rev (2018) 17:291–326 https://doi.org/10.1007/s11101-017-9532-2 BacHBerry: BACterial Hosts for production of Bioactive phenolics from bERRY fruits Alexey Dudnik . A. Filipa Almeida . Ricardo Andrade . Barbara Avila . Pilar Ban˜ados . Diane Barbay . Jean-Etienne Bassard . Mounir Benkoulouche . Michael Bott . Adelaide Braga . Dario Breitel . Rex Brennan . Laurent Bulteau . Celine Chanforan . Ineˆs Costa . Rafael S. Costa . Mahdi Doostmohammadi . Nuno Faria . Chengyong Feng . Armando Fernandes . Patricia Ferreira . Roberto Ferro . Alexandre Foito . Sabine Freitag . Gonc¸alo Garcia . Paula Gaspar . Joana Godinho-Pereira . Bjo¨rn Hamberger . Andra´s Hartmann . Harald Heider . Carolina Jardim . Alice Julien-Laferriere . Nicolai Kallscheuer . Wolfgang Kerbe . Oscar P. Kuipers . Shanshan Li . Nicola Love . Alberto Marchetti-Spaccamela . Jan Marienhagen . Cathie Martin . Arnaud Mary . Vincent Mazurek . Camillo Meinhart . David Me´ndez Sevillano . Regina Menezes . Michael Naesby . Morten H. H. Nørholm . Finn T. Okkels . Joana Oliveira . Marcel Ottens . Delphine Parrot . Lei Pei . Isabel Rocha . Rita Rosado-Ramos . Caroline Rousseau . Marie-France Sagot . Claudia Nunes dos Santos . Markus Schmidt . Tatiana Shelenga . Louise Shepherd . Ana Rita Silva . Marcelo Henriques da Silva . Olivier Simon . Steen Gustav Stahlhut . Ana Solopova . Artem Sorokin . Derek Stewart . Leen Stougie . Shang Su . Vera Thole . Olga Tikhonova . Martin Trick . Philippe Vain . Andre´ Verı´ssimo . Ana Vila-Santa . Susana Vinga . Michael Vogt . Liangsheng Wang . Lijin Wang . Wei Wei . Sandra Youssef . Ana Rute Neves . Jochen Forster Received: 6 December 2016 / Accepted: 29 August 2017 / Published online: 8 September 2017 Ó Springer Science+Business Media B.V. 2017 Abstract BACterial Hosts for production of Bioac- This article is written by the BacHBerry consortium (www. tive phenolics from bERRY fruits (BacHBerry) was a bachberry.eu) and represents the collective effort of all par- 3-year project funded by the Seventh Framework ticipating institutions. The authors are therefore listed in Programme (FP7) of the European Union that ran alphabetical order. between November 2013 and October 2016. The overall aim of the project was to establish a sustainable Electronic supplementary material The online version of this article (doi:10.1007/s11101-017-9532-2) contains supple- and economically-feasible strategy for the production mentary material, which is available to authorized users. A. Dudnik (&) Á R. Ferro Á P. Gaspar Á R. Andrade Á L. Bulteau Á A. Julien-Laferriere Á M. H. H. Nørholm Á S. G. Stahlhut Á J. Forster A. Marchetti-Spaccamela Á A. Mary Á The Novo Nordisk Foundation Center for D. Parrot Á M.-F. Sagot Á L. Stougie Biosustainability, Technical University of Denmark, Institut National de Recherche en Informatique et Kemitorvet, Building 220, 2800 Kgs., Lyngby, Denmark Automatique, 43 Boulevard du 11 Novembre 1918, e-mail: [email protected] 69622 Villeurbanne Cedex, France 123 292 Phytochem Rev (2018) 17:291–326 of novel high-value phenolic compounds isolated from C30H p-coumaroyl shikimate/quinate 30- berry fruits using bacterial platforms. The project hydroxylase aimed at covering all stages of the discovery and pre- C4H Cinnamate 4-hydroxylase commercialization process, including berry collec- CBD Convention on biological diversity tion, screening and characterization of their bioactive CaN Calcineurin components, identification and functional characteri- CDRE Calcineurin-dependent responsive element zation of the corresponding biosynthetic pathways, CHI Chalcone isomerase and construction of Gram-positive bacterial cell CHR Chalcone reductase factories producing phenolic compounds. Further CHS Chalcone synthase activities included optimization of polyphenol extrac- CPR Cytochrome-P450 reductase tion methods from bacterial cultures, scale-up of CVs Column volumes production by fermentation up to pilot scale, as well as CYP Cytochromes P450 societal and economic analyses of the processes. This DFR Dihydroflavonol 4-reductase review article summarizes some of the key findings F3H Flavanone 3-hydroxylase obtained throughout the duration of the project. F30H Flavonoid 30-hydroxylase F3050H Flavonoid 30-50-hydroxylase Keywords Berries Á Bioprospecting Á Microbial cell FLS Flavonol synthase factories Á Polyphenols Á Sustainable production FNS Flavone synthase FP7 European Commission’s the Seventh Abbreviations Framework programme 4CL 4-coumaryl-CoA ligase GFP Green fluorescent protein AD Alzheimer’s disease GRAS Generally regarded as safe ANS Anthocyanidin synthase HCT Hydroxycinnamoyl-CoA shikimate/quinate ALS Amyotrophic lateral sclerosis; hydroxycinnamoyltransferase anthocyanidin synthase HD Huntington’s disease ANR Anthocyanidin reductase HPLC High-performance liquid chromatography LAR Leucoanthocyanidin reductase C. Chanforan Á V. Mazurek Á F. T. Okkels Á O. Simon B. Avila P. Ban˜ados Á Chr. Hansen Natural Colors A/S, Agern Alle 24, Facultad De Agronomı´a e Ingenierı´a Forestal, Pontificia 2970 Hørsholm, Denmark Universidad Cato´lica de Chile, Av. Vicun˜a Mackenna Ote, 4860 Macul, Chile R. S. Costa Á M. Doostmohammadi Á A. Fernandes Á A. Hartmann Á A. Verı´ssimo Á A. Vila-Santa Á S. Vinga D. Barbay M. Benkoulouche H. Heider Á Á Á IDMEC, Instituto Superior Te´cnico, Universidade de M. Naesby C. Rousseau Á Lisboa, Av. Rovisco Pais 1, 1049-001 Lisbon, Portugal Evolva, Duggingerstrasse 23, 4053 Reinach, Switzerland R. Brennan Á A. Foito Á S. Freitag Á L. Shepherd Á J.-E. Bassard B. Hamberger Á D. Stewart Department of Plant and Environmental Science, The James Hutton Institute, Invergowrie, DD2 5DA, University of Copenhagen, 1871 Frederiksberg, Denmark Dundee, Scotland, UK M. Bott Á N. Kallscheuer Á J. Marienhagen Á M. Vogt O. P. Kuipers Á A. Solopova Forschungszentrum Ju¨lich GmbH, Institut fu¨r Bio- und Groningen Biomolecular Sciences and Biotechnology Geowissenschaften, IBG-1: Biotechnologie, Wilhelm- Institute, Department of Molecular Genetics, University Johnen-Straße, 52428 Ju¨lich, Germany of Groningen, Linnaeusborg, Nijenborgh 7, 9747 AG Groningen, The Netherlands A. Braga Á N. Faria Á P. Ferreira Á J. Oliveira Á I. Rocha Á A. R. Silva D. Breitel Á N. Love Á C. Martin Á V. Thole Á Biotempo, Avepark – Edif. Spinpark, Zona Industrial da M. Trick Á P. Vain Gandra, Barco, 4805-017 Guimara˜es, Portugal John Innes Centre, Norwich Research Park, NR4 7UH Norwich, UK 123 Phytochem Rev (2018) 17:291–326 293 LC- Liquid-chromatography mass-spectrometry eu) has received funding from the European Com- MS mission’s Seventh Framework Programme (FP7) NDs Neurodegenerative diseases under the theme KBBE.2013.3.1-01: ‘‘Plant High NFAT Nuclear Factor of Activated T-cells Value Products—from discovery to final product’’ NFjB Nuclear Factor jB with the goal of bringing together experts from the NP- The Nagoya protocol on access to genetic fields of plant biology, industrial biotechnology, ana- ABS resources and the fair and equitable sharing lytical chemistry, and social sciences in order to of benefits arising from their utilization assemble and validate a complete pipeline for dis- OMT O-methyltransferase covery and microbial production of novel phenolic PAL Phenylalanine ammonia-lyase compounds of plant origin. The consortium consisted PCA Principal component analysis of twelve academic groups, five small and medium PD Parkinson’s disease sized enterprises and one large enterprise from eleven PLS Partial least squares different countries, namely Austria, Chile, China, RNA- RNA sequencing technology Denmark, France, Germany, The Netherlands, Portu- seq gal, Russia, Switzerland and the United Kingdom. The STS Stilbene synthase diversity of partners has allowed access to a variety of SVR Support vector regression expertise and to plant material that had not been TAL Tyrosine ammonia-lyase characterized extensively. UFGT Flavonoid 3-O-glucosyltransferase Polyphenols as a source of bioactive molecules Introduction
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  • Extraction Et Hémisynthèse De Stilbènes De La Vigne Et Du Vin Pour Une Application En Santé Humaine Et Végétale Toni El Khawand

    Extraction Et Hémisynthèse De Stilbènes De La Vigne Et Du Vin Pour Une Application En Santé Humaine Et Végétale Toni El Khawand

    Extraction et hémisynthèse de stilbènes de la vigne et du vin pour une application en santé humaine et végétale Toni El Khawand To cite this version: Toni El Khawand. Extraction et hémisynthèse de stilbènes de la vigne et du vin pour une application en santé humaine et végétale. Médecine humaine et pathologie. Université de Bordeaux, 2019. Français. NNT : 2019BORD0402. tel-03083318 HAL Id: tel-03083318 https://tel.archives-ouvertes.fr/tel-03083318 Submitted on 19 Dec 2020 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. THÈSE PRÉSENTÉE POUR OBTENIR LE GRADE DE DOCTEUR DE L’UNIVERSITÉ DE BORDEAUX ÉCOLE DOCTORALE DES SCIENCES DE LA VIE ET DE LA SANTÉ SPÉCIALITÉ ŒNOLOGIE Par Toni EL KHAWAND Extraction et hémisynthèse de stilbènes de la vigne et du vin pour une application en santé humaine et végétale Sous la direction du Dr. Alain DECENDIT la co-direction du Pr. Tristan RICHARD et le co-encadrement du Dr. Stéphanie KRISA Soutenue publiquement le 18 décembre 2019 Membres du jury M. Rémy GHIDOSSI Professeur, Université de Bordeaux Président Mme. Marielle ADRIAN Professeur, Université de Bourgogne Rapporteur Mme. Laurence VOUTQUENNE Professeur, Université de Reims Rapporteur M.
  • Pterostilbene Monograph

    Pterostilbene Monograph

    Monograph amr Pterostilbene Monograph OH H3CO Introduction Pterostilbene is a chemical classified as a benzylidene compound (more specifically a stilbene) and is biologically classified as a Pterostilbene phytoalexin, which are antimicrobial sub- OCH stances that are part of the plant’s defense 3 system and are synthesized in response to pathogen infection. This monograph focuses coronary heart disease, as it can increase the HDL/ on trans-pterostilbene. LDL cholesterol ratio.20 Stilbenes are low molecular weight (approxi- Colon cancer is one of the leading causes of mately 200-300 g/mol), naturally occurring cancer mortality in men and women in Western polyphenol compounds produced by a variety of countries. Epidemiological studies have linked the plants that secrete them in response to environ- consumption of fruits and vegetables to a reduced mental challenges such as viral, microbial, and risk of colon cancer, in particular small fruits that fungal infection or excessive ultraviolet exposure.1 are particularly rich sources of pterostilbene and Stilbenes are found in a wide range of plant other pharmacologically active stilbenes.14 Recent families, including Vitis and Vaccinium.2,3 These advances in the study of colon cancer have stimu- molecules are synthesized via the phenylpropanoid lated an interest in diet and lifestyle as an effective pathway and are structurally similar to estrogen.4 means of prevention. As constituents of small Natural sources of pterostilbene include Vitis fruits such as grapes and berries and their products,
  • Profile of Stilbenes and Other Phenolics in Fanagoria White and Red Russian Wines

    Profile of Stilbenes and Other Phenolics in Fanagoria White and Red Russian Wines

    H OH metabolites OH Article Profile of Stilbenes and Other Phenolics in Fanagoria White and Red Russian Wines Andrey R. Suprun, Alexandra S. Dubrovina , Alexey P. Tyunin and Konstantin V. Kiselev * Laboratory of Biotechnology, Federal Scientific Center of the East Asia Terrestrial Biodiversity, FEB RAS, 690022 Vladivostok, Russia; [email protected] (A.R.S.); [email protected] (A.S.D.); [email protected] (A.P.T.) * Correspondence: [email protected]; Fax: +7-4232-310193 Abstract: Grapes and wines represent the most important source of edible stilbenes and other phenolic metabolites, which demonstrate a wide range of valuable biological activities. However, there is no information about the profile and content of phenolic compounds in Russian wines. We firstly analyzed phenolics (stilbenes, phenolic acids, and flavonols) in some representatives of Russian wines, including eleven red and seven white Russian wines from Fanagoria, Krasnodarsky Territory. The Russian red wines contained six stilbenes (trans-resveratrol, cis-resveratrol, trans-, cis-piceid, trans-piceatannol, d-viniferin), while the white wines contained only five stilbenes (cis- resveratrol, trans-, cis-piceid, trans-piceatannol, trans-resveratrol). More than a half of the total stilbenes in the wines (65% of all stilbenes) were presented by trans-piceid and cis-piceid, while trans-resveratrol reached 16% of all the stilbenes. The red wines also contained six phenolic acids and six flavonols, while the white wines contained six phenolic acids and only three flavonols. Myrecitin- Citation: Suprun, A.R.; Dubrovina, 3-O-glucoside, quercetin-3-O-glucoside, and myricetin were the major flavonols in the red wines, A.S.; Tyunin, A.P.; Kiselev, K.V.