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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. -
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. -
Building Blue E. Coli: Engineering the Anthocyanin Biosynthetic Pathway
Building blue E. coli: Engineering the anthocyanin biosynthetic pathway Leah Johnston1, Lucas Jarche1, Alexander Porter1, Julie Ryu1, Emma Price1, Emma Finlayson-Trick1, Khaled Aly1, Paul Bissonnette2, Eric Pace3, Dr. John Rohde1 1Department of Microbiology and Immunology, 2Department of Chemistry, 3Department of Agriculture Dalhousie University, Halifax, Canada, B3H 1X5 THE ANTHOCYANIN PATHWAY METHODS RESULTS 1kb (B) Method of Template DNA for each of the genes required for the production of the Anthocyanin biosynthetic Gene Size (bp) Function Epitope ladder (B) Acquisition of pathway in E. coli were acquired from the following sources outlined in Figure 1 (B). (A) Name Tag Template DNA 10 Phenylalanine Lyase involved in Amplified from A. (A) 2762 polyphenol S-Tag thaliana cDNA, Ammonia . synthesis. insert in Phenylalanine Ammonia Lyase and 4-Coumaroyl CoA Ligase were acquired as inserts in a 3.0. Lyase pACYCDuet-1 pACYCDuet-1 plasmid from Sinyuan Wang et. al (2005) at Utah State University. Cinnamate 4- 2.0 Phenylalanine from Utah State Hydroxylase-HA fusion protein was inserted into this plasmid at the end of the PAL coding region 1.5 Phenylalanine ammonia lyase University using restriction enzymes and transformed into BL21 CaCl2 competent E. coli with T7 RNA Cinnamate 4- Oxidoreductase Amplified from A. Cinnamic Acid 1518 involved in HA-Tag thaliana cDNA, Polymerase activity. A western blot with anti-HA antibody was used to detect the presence of the 1.0 Hydroxylase phenylalanine purchased from C4H fusion protein in the resultant cells. Cinnamate 4-hydroxylase metabolism. TAIR database P-Coumaric Acid 4-Coumaroyl Ligase involved in Insert in 2546 phenylpropanoid His-Tag pACYCDuet-1 Chalcone Synthase, Chalcone Isomerase and Flavanone 3-Hydroxylase were amplified from the CoA Ligase 0.5 4-coumaryl-coenzyme A ligase biosynthesis. -
L.) Leaves Tao Jiang1,3, Kunyuan Guo2,3, Lingdi Liu1, Wei Tian1, Xiaoliang Xie1, Saiqun Wen1 & Chunxiu Wen1*
www.nature.com/scientificreports OPEN Integrated transcriptomic and metabolomic data reveal the favonoid biosynthesis metabolic pathway in Perilla frutescens (L.) leaves Tao Jiang1,3, Kunyuan Guo2,3, Lingdi Liu1, Wei Tian1, Xiaoliang Xie1, Saiqun Wen1 & Chunxiu Wen1* Perilla frutescens (L.) is an important medicinal and edible plant in China with nutritional and medical uses. The extract from leaves of Perilla frutescens contains favonoids and volatile oils, which are mainly used in traditional Chinese medicine. In this study, we analyzed the transcriptomic and metabolomic data of the leaves of two Perilla frutescens varieties: JIZI 1 and JIZI 2. A total of 9277 diferentially expressed genes and 223 favonoid metabolites were identifed in these varieties. Chrysoeriol, apigenin, malvidin, cyanidin, kaempferol, and their derivatives were abundant in the leaves of Perilla frutescens, which were more than 70% of total favonoid contents. A total of 77 unigenes encoding 15 enzymes were identifed as candidate genes involved in favonoid biosynthesis in the leaves of Perilla frutescens. High expression of the CHS gene enhances the accumulation of favonoids in the leaves of Perilla frutescens. Our results provide valuable information on the favonoid metabolites and candidate genes involved in the favonoid biosynthesis pathways in the leaves of Perilla frutescens. Perilla frutescens (L.), which is a self-compatible annual herb, belongs to the family Lamiaceae. Tis species has been widely cultivated in China, Japan, and Korea for centuries. Perilla frutescens is an important medicinal and edible plant in China with medical and nutritional uses 1. Its leaves can be utilized as a transitional medicinal herb, as a vegetable, and as a spice, and its seeds can be processed into foods and nutritional edible oils 2. -
Analysis of the Chromosomal Clustering of Fusarium-Responsive
www.nature.com/scientificreports OPEN Analysis of the chromosomal clustering of Fusarium‑responsive wheat genes uncovers new players in the defence against head blight disease Alexandre Perochon1,2, Harriet R. Benbow1,2, Katarzyna Ślęczka‑Brady1, Keshav B. Malla1 & Fiona M. Doohan1* There is increasing evidence that some functionally related, co‑expressed genes cluster within eukaryotic genomes. We present a novel pipeline that delineates such eukaryotic gene clusters. Using this tool for bread wheat, we uncovered 44 clusters of genes that are responsive to the fungal pathogen Fusarium graminearum. As expected, these Fusarium‑responsive gene clusters (FRGCs) included metabolic gene clusters, many of which are associated with disease resistance, but hitherto not described for wheat. However, the majority of the FRGCs are non‑metabolic, many of which contain clusters of paralogues, including those implicated in plant disease responses, such as glutathione transferases, MAP kinases, and germin‑like proteins. 20 of the FRGCs encode nonhomologous, non‑metabolic genes (including defence‑related genes). One of these clusters includes the characterised Fusarium resistance orphan gene, TaFROG. Eight of the FRGCs map within 6 FHB resistance loci. One small QTL on chromosome 7D (4.7 Mb) encodes eight Fusarium‑ responsive genes, fve of which are within a FRGC. This study provides a new tool to identify genomic regions enriched in genes responsive to specifc traits of interest and applied herein it highlighted gene families, genetic loci and biological pathways of importance in the response of wheat to disease. Prokaryote genomes encode co-transcribed genes with related functions that cluster together within operons. Clusters of functionally related genes also exist in eukaryote genomes, including fungi, nematodes, mammals and plants1. -
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. -
Anti-Inflammatory Role of Curcumin in LPS Treated A549 Cells at Global Proteome Level and on Mycobacterial Infection
Anti-inflammatory Role of Curcumin in LPS Treated A549 cells at Global Proteome level and on Mycobacterial infection. Suchita Singh1,+, Rakesh Arya2,3,+, Rhishikesh R Bargaje1, Mrinal Kumar Das2,4, Subia Akram2, Hossain Md. Faruquee2,5, Rajendra Kumar Behera3, Ranjan Kumar Nanda2,*, Anurag Agrawal1 1Center of Excellence for Translational Research in Asthma and Lung Disease, CSIR- Institute of Genomics and Integrative Biology, New Delhi, 110025, India. 2Translational Health Group, International Centre for Genetic Engineering and Biotechnology, New Delhi, 110067, India. 3School of Life Sciences, Sambalpur University, Jyoti Vihar, Sambalpur, Orissa, 768019, India. 4Department of Respiratory Sciences, #211, Maurice Shock Building, University of Leicester, LE1 9HN 5Department of Biotechnology and Genetic Engineering, Islamic University, Kushtia- 7003, Bangladesh. +Contributed equally for this work. S-1 70 G1 S 60 G2/M 50 40 30 % of cells 20 10 0 CURI LPSI LPSCUR Figure S1: Effect of curcumin and/or LPS treatment on A549 cell viability A549 cells were treated with curcumin (10 µM) and/or LPS or 1 µg/ml for the indicated times and after fixation were stained with propidium iodide and Annexin V-FITC. The DNA contents were determined by flow cytometry to calculate percentage of cells present in each phase of the cell cycle (G1, S and G2/M) using Flowing analysis software. S-2 Figure S2: Total proteins identified in all the three experiments and their distribution betwee curcumin and/or LPS treated conditions. The proteins showing differential expressions (log2 fold change≥2) in these experiments were presented in the venn diagram and certain number of proteins are common in all three experiments. -
Supplementary Material
CSIRO PUBLISHING www.publish.csiro.au/journals/fpb Functional Plant Biology 33, 1–24 Supplementary material: FP05139_AC Supplementary material Molecular targets of elevated [CO2] in leaves and stems of Populus deltoides: implications for future tree growth and carbon sequestration Nathalie DruartA,B, Marisa Rodríguez-BueyA, Greg Barron-GaffordC, Andreas SjödinA, Rishikesh BhaleraoB and Vaughan HurryA,D AUmeå Plant Science Centre, Department of Plant Physiology, Umeå University, S-901 87 Umeå, Sweden. BUmeå Plant Science Centre, Department of Forest Genetics and Plant Physiology, Swedish University of Agricultural Sciences, S-901 83 Umeå, Sweden. CBiosphere 2 Laboratory, Columbia University, Oracle AZ 85623 USA. Current address: Ecology and Evolutionary Biology, University of Arizona, Tucson, AZ 85719, USA. DCorresponding author. Email: [email protected] Appendix S1 1.0 1.0 A B 0.5 0.5 0.0 0.0 –0.5 –0.5 –1.0 –1.0 Relative gene expression (log gene expression Relative ) 1.0 1.0 2 C D 0.5 0.5 0.0 0.0 –0.5 –0.5 2 ) Relative gene expression (log gene expression Relative –1.0 –1.0 1.0 1.0 E F 0.5 0.5 0.0 0.0 –0.5 –0.5 –1.0 –1.0 400 800 1200 400 800 1200 Ambient [CO2] (µmol mol–1) Validation of reproducibility of the hybridisations by comparing the hybridisation results of three genes for which two independent cDNA clones had been spotted on the array. (A, C, E leaves; B, D, F stems). (A, B) Protein phosphatase 2A, 65 kDa subunit. (C, D) Elicitor-inducible cytochrome P450. -
Ginger and Turmeric Expressed Sequence Tags Identify Signature
Ginger and turmeric expressed sequence tags identify signature genes for rhizome identity and development and the biosynthesis of curcuminoids, gingerols and terpenoids Koo et al. Koo et al. BMC Plant Biology 2013, 13:27 http://www.biomedcentral.com/1471-2229/13/27 Koo et al. BMC Plant Biology 2013, 13:27 http://www.biomedcentral.com/1471-2229/13/27 RESEARCH ARTICLE Open Access Ginger and turmeric expressed sequence tags identify signature genes for rhizome identity and development and the biosynthesis of curcuminoids, gingerols and terpenoids Hyun Jo Koo1,6†, Eric T McDowell1†, Xiaoqiang Ma1,7†, Kevin A Greer2,8, Jeremy Kapteyn1, Zhengzhi Xie1,3,9, Anne Descour2, HyeRan Kim1,4,10, Yeisoo Yu1,4, David Kudrna1,4, Rod A Wing1,4, Carol A Soderlund2 and David R Gang1,5,11* Abstract Background: Ginger (Zingiber officinale) and turmeric (Curcuma longa) accumulate important pharmacologically active metabolites at high levels in their rhizomes. Despite their importance, relatively little is known regarding gene expression in the rhizomes of ginger and turmeric. Results: In order to identify rhizome-enriched genes and genes encoding specialized metabolism enzymes and pathway regulators, we evaluated an assembled collection of expressed sequence tags (ESTs) from eight different ginger and turmeric tissues. Comparisons to publicly available sorghum rhizome ESTs revealed a total of 777 gene transcripts expressed in ginger/turmeric and sorghum rhizomes but apparently absent from other tissues. The list of rhizome-specific transcripts was enriched for genes associated with regulation of tissue growth, development, and transcription. In particular, transcripts for ethylene response factors and AUX/IAA proteins appeared to accumulate in patterns mirroring results from previous studies regarding rhizome growth responses to exogenous applications of auxin and ethylene. -
Epigenetic Associations in Relation to Cardiovascular Prevention and Therapeutics Susanne Voelter-Mahlknecht
Voelter-Mahlknecht Clinical Epigenetics (2016) 8:4 DOI 10.1186/s13148-016-0170-0 REVIEW Open Access Epigenetic associations in relation to cardiovascular prevention and therapeutics Susanne Voelter-Mahlknecht Abstract Cardiovascular diseases (CVD) increasingly burden societies with vast financial and health care problems. Therefore, the importance of improving preventive and therapeutic measures against cardiovascular diseases is continually growing. To accomplish such improvements, research must focus particularly on understanding the underlying mechanisms of such diseases, as in the field of epigenetics, and pay more attention to strengthening primary prevention. To date, preliminary research has found a connection between DNA methylation, histone modifications, RNA-based mechanisms and the development of CVD like atherosclerosis, cardiac hypertrophy, myocardial infarction, and heart failure. Several therapeutic agents based on the findings of such research projects are currently being tested for use in clinical practice. Although these tests have produced promising data so far, no epigenetically active agents or drugs targeting histone acetylation and/or methylation have actually entered clinical trials for CVDs, nor have they been approved by the FDA. To ensure the most effective prevention and treatment possible, further studies are required to understand the complex relationship between epigenetic regulation and the development of CVD. Similarly, several classes of RNA therapeutics are currently under development. The use of miRNAs and their targets as diagnostic or prognostic markers for CVDs is promising, but has not yet been realized. Further studies are necessary to improve our understanding of the involvement of lncRNA in regulating gene expression changes underlying heart failure. Through the data obtained from such studies, specific therapeutic strategies to avoid heart failure based on interference with incRNA pathways could be developed. -
Transcription Factors Regulating Terpene Synthases in Tomato Trichomes
UvA-DARE (Digital Academic Repository) Transcription factors regulating terpene synthases in tomato trichomes Spyropoulou, E. Publication date 2012 Document Version Final published version Link to publication Citation for published version (APA): Spyropoulou, E. (2012). Transcription factors regulating terpene synthases in tomato trichomes. General rights 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), other than for strictly personal, individual use, unless the work is under an open content license (like Creative Commons). Disclaimer/Complaints regulations If you believe that digital publication of certain material infringes any of your rights or (privacy) interests, please let the Library know, stating your reasons. In case of a legitimate complaint, the Library will make the material inaccessible and/or remove it from the website. Please Ask the Library: https://uba.uva.nl/en/contact, or a letter to: Library of the University of Amsterdam, Secretariat, Singel 425, 1012 WP Amsterdam, The Netherlands. You will be contacted as soon as possible. UvA-DARE is a service provided by the library of the University of Amsterdam (https://dare.uva.nl) Download date:03 Oct 2021 Transcription factors regulating terpene synthases in tomato trichomes factors regulating Transcription Transcription factors regulating terpene synthases in tomato trichomes Eleni Spyropoulou Eleni Spyropoulou Transcription factors regulating terpene synthases in tomato trichomes ACADEMISCH PROEFSCHRIFT ter verkrijging van de graad van doctor aan de Universiteit van Amsterdam op gezag van de Rector Magnificus prof. dr. D.C. van den Boom ten overstaan van een door het college voor promoties ingestelde commissie, in het openbaar te verdedigen in de Agnietenkapel op dinsdag 03 juli 2012, te 16:00 uur door Eleni Spyropoulou geboren te Marousi, Griekenland PROMOTIECOMISSIE Promotor Prof. -
Noncatalytic Chalcone Isomerase-Fold Proteins in Humulus Lupulus Are Auxiliary Components in Prenylated Flavonoid Biosynthesis
Noncatalytic chalcone isomerase-fold proteins in Humulus lupulus are auxiliary components in prenylated flavonoid biosynthesis Zhaonan Bana,b, Hao Qina, Andrew J. Mitchellc, Baoxiu Liua, Fengxia Zhanga, Jing-Ke Wengc,d, Richard A. Dixone,f,1, and Guodong Wanga,1 aState Key Laboratory of Plant Genomics and National Center for Plant Gene Research, Institute of Genetics and Developmental Biology, Chinese Academy of Sciences, 100101 Beijing, China; bUniversity of Chinese Academy of Sciences, 100049 Beijing, China; cWhitehead Institute for Biomedical Research, Cambridge, MA 02142; dDepartment of Biology, Massachusetts Institute of Technology, Cambridge, MA 02139; eBioDiscovery Institute, University of North Texas, Denton, TX 76203; and fDepartment of Biological Sciences, University of North Texas, Denton, TX 76203 Contributed by Richard A. Dixon, April 25, 2018 (sent for review February 6, 2018; reviewed by Joerg Bohlmann and Mattheos A. G. Koffas) Xanthohumol (XN) and demethylxanthohumol (DMX) are special- braries have been deposited in the TrichOME database [www. ized prenylated chalconoids with multiple pharmaceutical appli- planttrichome.org (18)], and numerous large RNAseq datasets from cations that accumulate to high levels in the glandular trichomes different hop tissues or cultivars have also been made publically of hops (Humulus lupulus L.). Although all structural enzymes in available. By mining the hops transcriptome data, we and others have the XN pathway have been functionally identified, biochemical functionally identified several key terpenophenolic biosynthetic en- mechanisms underlying highly efficient production of XN have zymes from hop glandular trichomes (1, 18–23); these include car- not been fully resolved. In this study, we characterized two non- boxyl CoA ligase (CCL) genes and two aromatic prenyltransferase catalytic chalcone isomerase (CHI)-like proteins (designated as (PT) genes (HlPT1L and HlPT2) (22, 23).