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BacHBerry: BACterial Hosts for production of Bioactive phenolics from bERRY fruits Alexey Dudnik, Filipa Almeida, Ricardo Andrade, Barbara Avila, Pilar Bañados, Barbay Diane, Jean-Etienne Bassard, Mounir Benkoulouche, Michael Bott, Adelaide Braga, et al. To cite this version: Alexey Dudnik, Filipa Almeida, Ricardo Andrade, Barbara Avila, Pilar Bañados, et al.. BacHBerry: BACterial Hosts for production of Bioactive phenolics from bERRY fruits. Phytochemistry Reviews, Springer Verlag, 2017, pp.1-36. 10.1007/s11101-017-9532-2. hal-01673596 HAL Id: hal-01673596 https://hal.inria.fr/hal-01673596 Submitted on 30 Dec 2017 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. 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 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 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. F30HFlavonoid 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 ADAlzheimer’s disease GRAS Generally regarded as safe ANS Anthocyanidin synthase HCT Hydroxycinnamoyl-CoA shikimate/quinate ALS Amyotrophic lateral sclerosis; hydroxycinnamoyltransferase anthocyanidin synthase HDHuntington’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 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’’ NFjBNuclear 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 PDParkinson’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 Historically, plants have been not only important BacHBerry (BACterial Hosts for production of Bioac- sources of nutrients and energy in the human diet but tive phenolics from bERRY fruits, www.bachberry. also have provided the fundamentals of traditional and W. Kerbe Á C. Meinhart Á L. Pei Á M. Schmidt Á D. Stewart S. Youssef Institute of Mechanical, Process and Energy Engineering, Biofaction KG, Kundmanngasse 39/12, 1030 Vienna, School of Engineering and Physical Sciences, Heriot Watt Austria University, Edinburgh, Scotland, UK D. M. Sevillano Á M. Ottens Á M. H. da Silva A. F. Almeida Á I. Costa Á G. Garcia Á Department of Biotechnology, Delft University of J. Godinho-Pereira Á C. Jardim Á R.
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    Stability and Photoisomerization of Stilbenes Isolated from the Bark of Norway Spruce Roots

    molecules Article Stability and Photoisomerization of Stilbenes Isolated from the Bark of Norway Spruce Roots Harri Latva-Mäenpää 1,2,* , Riziwanguli Wufu 1 , Daniel Mulat 1, Tytti Sarjala 3, Pekka Saranpää 3,* and Kristiina Wähälä 1,4,* 1 Department of Chemistry, University of Helsinki, P.O. Box 55, FI-00014 Helsinki, Finland; riziwanguli.wufu@helsinki.fi (R.W.); [email protected] (D.M.) 2 Foodwest, Kärryväylä 4, FI-60100 Seinäjoki, Finland 3 Natural Resources Institute Finland, Tietotie 2, FI-02150 Espoo, Finland; tytti.sarjala@luke.fi 4 Department of Biochemistry and Developmental Biology, University of Helsinki, P.O. Box 63, FI-00014 Helsinki, Finland * Correspondence: harri.latva-maenpaa@foodwest.fi (H.L.-M.); pekka.saranpaa@luke.fi (P.S.); kristiina.wahala@helsinki.fi (K.W.); Tel.: +358-50-4487502 (H.L.-M. & P.S. & K.W.) Abstract: Stilbenes or stilbenoids, major polyphenolic compounds of the bark of Norway spruce (Picea abies L. Karst), have potential future applications as drugs, preservatives and other functional ingredients due to their antioxidative, antibacterial and antifungal properties. Stilbenes are photosen- sitive and UV and fluorescent light induce trans to cis isomerisation via intramolecular cyclization. So far, the characterizations of possible new compounds derived from trans-stilbenes under UV light exposure have been mainly tentative based only on UV or MS spectra without utilizing more detailed structural spectroscopy techniques such as NMR. The objective of this work was to study the stability Citation: Latva-Mäenpää, H.; Wufu, of biologically interesting and readily available stilbenes such as astringin and isorhapontin and R.; Mulat, D.; Sarjala, T.; Saranpää, P.; their aglucones piceatannol and isorhapontigenin, which have not been studied previously.
  • Resveratrol: Twenty Years of Growth, Development and Controversy

    Resveratrol: Twenty Years of Growth, Development and Controversy

    Invited Review Biomol Ther 27(1), 1-14 (2019) Resveratrol: Twenty Years of Growth, Development and Controversy John M. Pezzuto* Arnold & Marie Schwartz College of Pharmacy and Health Sciences, Long Island University, Brooklyn, NY 11201, USA Abstract Resveratrol was first isolated in 1939 by Takaoka fromVeratrum grandiflorum O. Loes. Following this discovery, sporadic descrip- tive reports appeared in the literature. However, spurred by our seminal paper published nearly 60 years later, resveratrol became a household word and the subject of extensive investigation. Now, in addition to appearing in over 20,000 research papers, resveratrol has inspired monographs, conferences, symposia, patents, chemical derivatives, etc. In addition, dietary supple- ments are marketed under various tradenames. Once resveratrol was brought to the limelight, early research tended to focus on pharmacological activities related to the cardiovascular system, inflammation, and cancer but, over the years, the horizon greatly expanded. Around 130 human clinical trials have been (or are being) conducted with varying results. This may be due to factors such as disparate doses (ca. 5 to 5,000 mg/day) and variable experimental settings. Further, molecular targets are numerous and a dominant mechanism is elusive or nonexistent. In this context, the compound is overtly promiscuous. Nonetheless, since the safety profile is pristine, and use as a dietary supplement is prevalent, these features are not viewed as detrimental. Given the ongoing history of resveratrol, it is reasonable to advocate for additional development and further clinical investigation. Topical preparations seem especially promising, as do conditions that can respond to anti-inflammatory action and/or direct exposure, such as colon cancer prevention.