Multi-Substrate Terpene Synthases: Their Occurrence and Physiological
Total Page:16
File Type:pdf, Size:1020Kb
Load more
Recommended publications
-
Molecular Regulation of Plant Monoterpene Biosynthesis in Relation to Fragrance
Molecular Regulation of Plant Monoterpene Biosynthesis In Relation To Fragrance Mazen K. El Tamer Promotor: Prof. Dr. A.G.J Voragen, hoogleraar in de Levensmiddelenchemie, Wageningen Universiteit Co-promotoren: Dr. ir. H.J Bouwmeester, senior onderzoeker, Business Unit Celcybernetica, Plant Research International Dr. ir. J.P Roozen, departement Agrotechnologie en Voedingswetenschappen, Wageningen Universiteit Promotiecommissie: Dr. M.C.R Franssen, Wageningen Universiteit Prof. Dr. J.H.A Kroeze, Wageningen Universiteit Prof. Dr. A.J van Tunen, Swammerdam Institute for Life Sciences, Universiteit van Amsterdam. Prof. Dr. R.G.F Visser, Wageningen Universiteit Mazen K. El Tamer Molecular Regulation Of Plant Monoterpene Biosynthesis In Relation To Fragrance Proefschrift ter verkrijging van de graad van doctor op gezag van de rector magnificus van Wageningen Universiteit, Prof. dr. ir. L. Speelman, in het openbaar te verdedigen op woensdag 27 november 2002 des namiddags te vier uur in de Aula Mazen K. El Tamer Molecular Regulation Of Plant Monoterpene Biosynthesis In Relation To Fragrance Proefschrift Wageningen Universiteit ISBN 90-5808-752-2 Cover and Invitation Design: Zeina K. El Tamer This thesis is dedicated to my Family & Friends Contents Abbreviations Chapter 1 General introduction and scope of the thesis 1 Chapter 2 Monoterpene biosynthesis in lemon (Citrus limon) cDNA isolation 21 and functional analysis of four monoterpene synthases Chapter 3 Domain swapping of Citrus limon monoterpene synthases: Impact 57 on enzymatic activity and -
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. -
Floral Volatile Alleles Can Contribute to Pollinatormediated
Zurich Open Repository and Archive University of Zurich Main Library Strickhofstrasse 39 CH-8057 Zurich www.zora.uzh.ch Year: 2014 Floral volatile alleles can contribute to pollinator-mediated reproductive isolation in monkeyflowers (Mimulus) Byers, Kelsey J R P ; Vela, James P ; Peng, Foen ; Riffell, Jeffrey A ; Bradshaw, HD Abstract: Pollinator-mediated reproductive isolation is a major factor in driving the diversification of flowering plants. Studies of floral traits involved in reproductive isolation have focused nearly exclusively on visual signals, such as flower color. The role of less obvious signals, such as floral scent, hasbeen studied only recently. In particular, the genetics of floral volatiles involved in mediating differential pollinator visitation remains unknown. The bumblebee-pollinated Mimulus lewisii and hummingbird- pollinated M. cardinalis are a model system for studying reproductive isolation via pollinator preference. We have shown that these two species differ in three floral terpenoid volatiles - D-limonene, -myrcene, and E--ocimene - that are attractive to bumblebee pollinators. By genetic mapping and in vitro enzyme activity analysis we demonstrate that these interspecific differences are consistent with allelic variation at two loci – LIMONENE-MYRCENE SYNTHASE (LMS) and OCIMENE SYNTHASE (OS). M. lewisii LMS (MlLMS) and OS (MlOS) are expressed most strongly in floral tissue in the last stages of floral development. M. cardinalis LMS (McLMS) is weakly expressed and has a nonsense mutation in exon 3. M. cardinalis OS (McOS) is expressed similarly to MlOS, but the encoded McOS enzyme produces no E--ocimene. Recapitulating the M. cardinalis phenotype by reducing the expression of MlLMS by RNAi in transgenic M. -
{Replace with the Title of Your Dissertation}
Metabolic Regulation and Genetic Tools for Bacterial Neutral Lipid Production A THESIS SUBMITTED TO THE FACULTY OF THE GRADUATE SCHOOL OF THE UNIVERSITY OF MINNESOTA BY Nagendra Prasad Palani IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF MASTER OF SCIENCE Dr. Brett M. Barney September 2011 © Nagendra Prasad Palani 2011 Acknowledgements I express my most sincere thanks to Dr. Brett Barney. He has been an exceptional teacher, advisor and mentor for me. He has been unfailingly supportive during my time here and I cannot thank him enough for all he has taught me. I also thank the Department of Bioproducts & Biosystems Engineering, University of Minnesota, the National Science Foundation and the Department of Energy for their support of research in Dr. Barney’s lab. I thank my committee members Dr. Igor Libourel and Dr. Simo Sarkanen for posing critical questions about my research, helping me think better in the process. Their wisdom and insight often set me into thinking about my research from new perspectives. I thank fellow graduate and undergraduate students of the Barney lab and members of the Libourel lab for the many favors I have asked of them. I thank my friends here in the US for their fantastic company. I cannot express enough gratitude to my friends back home, who stepped in as sons and brothers whenever my family needed me. I thank my parents and my sister for their unwavering love, support and confidence in me. For her incredible patience and steadfast support, many thanks to my best friend and soon-to-be wife, Ajeetha. -
Biosynthetic Origin of Complex Terpenoid Mixtures by Multiproduct Enzymes, Metal Cofactors, and Substrate Isomers
Natural Products Chemistry & Research Review Article Biosynthetic Origin of Complex Terpenoid Mixtures by Multiproduct Enzymes, Metal Cofactors, and Substrate Isomers Vattekkatte A, Boland W * Department of Bioorganic Chemistry, Max Planck Institute for Chemical Ecology, Beutenberg Campus, Hans-Knöll-Strasse 8, D-07745 Jena, Germany ABSTRACT Terpenoids form a substantial portion of chemical diversity in nature. The enormous terpenoid diversity of more than 80,000 compounds is supported by the multisubstrate and multiproduct nature of certain enzymes from the various terpene synthases and terpene cyclases. These highly versatile enzymes are not only able to accept multiple substrates in their active site, but also simultaneously catalyze multiple reactions to the resultant multiple products. Interestingly, apart from the substrates and catalytic mechanisms, multiple regulation factors are able to alter the product profile of multiproduct terpene synthases. Simple variations in cellular conditions by changes in metal cofactors, assay pH, temperature and substrate geometry lead to significant shifts in product profiles. Switch in substrate stereochemistry for multiproduct terpene synthases in some case shows enhanced biocatalysis and in others initiates even a novel cyclization cascade. Hence, organisms can get access to a greater chemodiversity and avoid the expensive process of developing new biocatalysts just by simple changes in the cellular environment. This possibility of modulating chemical diversity provides immobile plants in the same generation access to an enhanced chemical arsenal for defense and communication by simply altering cofactors, pH level, and temperature and substrate geometry. Keywords: Terpenoids; Biocatalysis; Polymers; Substrate isomers; Catalysis INTRODUCTION and waxy cuticles acts as sunscreen, plant polymers like lignin Plants being immobile organisms do not have the ability to and rubber provide support and wound healing. -
WO 2014/152434 A2 25 September 2014 (25.09.2014) P O P C T
(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 WO 2014/152434 A2 25 September 2014 (25.09.2014) P O P C T (51) International Patent Classification: (74) Agents: HEBERT, Michael, L. et al; Jones Day, 222 East A61B 17/70 (2006.01) 41st Street, New York, NY 10017-6702 (US). (21) International Application Number: (81) Designated States (unless otherwise indicated, for every PCT/US2014/027337 kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (22) International Filing Date: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, 14 March 2014 (14.03.2014) DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (25) Filing Language: English HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, (26) Publication Language: English MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, (30) Priority Data: OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, 61/799,255 15 March 2013 (15.03.2013) US SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, 61/857,174 22 July 2013 (22.07.2013) US TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 61/876,610 11 September 2013 ( 11.09.2013) us ZW. 61/945,082 26 February 2014 (26.02.2014) us (84) Designated States (unless otherwise indicated, for every 61/945,109 26 February 2014 (26.02.2014) us kind of regional protection available): ARIPO (BW, GH, (71) Applicant: GENOMATICA, INC. -
Metabolomics for Plant Improvement: Status and Prospects
fpls-08-01302 August 3, 2017 Time: 16:49 # 1 View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by ICRISAT Open Access Repository REVIEW published: 07 August 2017 doi: 10.3389/fpls.2017.01302 Metabolomics for Plant Improvement: Status and Prospects Rakesh Kumar1,2, Abhishek Bohra3, Arun K. Pandey2, Manish K. Pandey2* and Anirudh Kumar4* 1 Department of Plant Sciences, University of Hyderabad (UoH), Hyderabad, India, 2 International Crops Research Institute for the Semi-Arid Tropics (ICRISAT), Hyderabad, India, 3 Crop Improvement Division, Indian Institute of Pulses Research (IIPR), Kanpur, India, 4 Department of Botany, Indira Gandhi National Tribal University (IGNTU), Amarkantak, India Post-genomics era has witnessed the development of cutting-edge technologies that have offered cost-efficient and high-throughput ways for molecular characterization of the function of a cell or organism. Large-scale metabolite profiling assays have allowed researchers to access the global data sets of metabolites and the corresponding metabolic pathways in an unprecedented way. Recent efforts in metabolomics have been directed to improve the quality along with a major focus on yield related traits. Importantly, an integration of metabolomics with other approaches such as quantitative Edited by: genetics, transcriptomics and genetic modification has established its immense Manoj K. Sharma, Jawaharlal Nehru University, India relevance to plant improvement. An effective combination of these modern approaches Reviewed by: guides researchers to pinpoint the functional gene(s) and the characterization of massive Stefanie Wienkoop, metabolites, in order to prioritize the candidate genes for downstream analyses and University of Vienna, Austria ultimately, offering trait specific markers to improve commercially important traits. -
Plant Terpenoid Synthases: Molecular Biology and Phylogenetic Analysis (Terpene Cyclase͞isoprenoids͞plant Defense͞genetic Engineering͞secondary Metabolism)
Proc. Natl. Acad. Sci. USA Vol. 95, pp. 4126–4133, April 1998 Biochemistry This contribution is part of the special series of Inaugural Articles by members of the National Academy of Sciences elected on April 29, 1997. Plant terpenoid synthases: Molecular biology and phylogenetic analysis (terpene cyclaseyisoprenoidsyplant defenseygenetic engineeringysecondary metabolism) JO¨RG BOHLMANN*†,GILBERT MEYER-GAUEN‡, AND RODNEY CROTEAU*§ *Institute of Biological Chemistry, Washington State University, Pullman, WA 99164-6340; and ‡Human Genetics Center, University of Texas, Houston, TX 77225 Contributed by Rodney Croteau, February 25, 1998 ABSTRACT This review focuses on the monoterpene, field is periodically surveyed (10, 11). After brief coverage of the sesquiterpene, and diterpene synthases of plant origin that use three types of terpene synthases from higher plants, with empha- the corresponding C10,C15, and C20 prenyl diphosphates as sis on common features of structure and function, we focus here substrates to generate the enormous diversity of carbon on molecular cloning and sequence analysis of these important skeletons characteristic of the terpenoid family of natural and fascinating catalysts. products. A description of the enzymology and mechanism of Enzymology and Mechanism of Terpenoid Cyclization terpenoid cyclization is followed by a discussion of molecular cloning and heterologous expression of terpenoid synthases. GDP is considered to be the natural substrate for monoterpene Sequence relatedness and phylogenetic reconstruction, based synthases, because all enzymes of this class efficiently utilize this on 33 members of the Tps gene family, are delineated, and precursor without the formation of free intermediates (12). Since comparison of important structural features of these enzymes GDP cannot be cyclized directly because of the C2-C3 trans- is provided. -
Transcriptome Analysis of Thapsia
PUBLISHED VERSION Drew, Damian; Dueholm, Bjorn; Weitzel, Corinna; Zhang, Ye; Sensen, Christoph W.; Simonsen, Henrik Transcriptome analysis of Thapsia laciniata rouy provides insights into terpenoid biosynthesis and diversity in apiaceae, International Journal of Molecular Sciences, 2013; 14(5):9080-9098. © 2013 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). PERMISSIONS http://www.mdpi.com/about/openaccess All articles published by MDPI are made immediately available worldwide under an open access license. This means: everyone has free and unlimited access to the full-text of all articles published in MDPI journals, and everyone is free to re-use the published material if proper accreditation/citation of the original publication is given. 8th August 2013 http://hdl.handle.net/2440/79105 Int. J. Mol. Sci. 2013, 14, 9080-9098; doi:10.3390/ijms14059080 OPEN ACCESS International Journal of Molecular Sciences ISSN 1422-0067 www.mdpi.com/journal/ijms Article Transcriptome Analysis of Thapsia laciniata Rouy Provides Insights into Terpenoid Biosynthesis and Diversity in Apiaceae Damian Paul Drew 1,2, Bjørn Dueholm 1, Corinna Weitzel 1, Ye Zhang 3, Christoph W. Sensen 3 and Henrik Toft Simonsen 1,* 1 Department of Plant and Environmental Sciences, Faculty of Sciences, University of Copenhagen, Frederiksberg DK-1871, Denmark; E-Mails: [email protected] (D.P.D.); [email protected] (B.D.); [email protected] (C.W.) 2 Wine Science and Business, School of Agriculture Food and Wine, University of Adelaide, South Australia, SA 5064, Australia 3 Department of Biochemistry and Molecular Biology, Faculty of Medicine, University of Calgary, Calgary, AB T2N 1N4, Canada; E-Mails: [email protected] (Y.Z.); [email protected] (C.W.S.) * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +45-353-33328. -
( 12 ) Patent Application Publication ( 10 ) Pub . No .: US 2019/0382802 A1
INDUS 20190382802A1 IN (19 ) United States (12 ) Patent Application Publication ( 10) Pub. No .: US 2019/0382802 A1 Keasling et al. (43 ) Pub . Date : Dec. 19 , 2019 (54 ) GENETICALLY MODIFIED HOST CELLS Publication Classification AND USE OF SAME FOR PRODUCING ( 51 ) Int. Ci. ISOPRENOID COMPOUNDS C12P 5/00 (2006.01 ) C12N 9/10 (2006.01 ) (71 ) Applicant: The Regents of the University of C12N 15/81 (2006.01 ) California , Oakland , CA (US ) C12P 23/00 (2006.01 ) C12N 9/04 (2006.01 ) ( 72 ) Inventors : Jay D. Keasling, Berkeley , CA (US ) ; C12N 9/88 ( 2006.01 ) James Kirby , Berkeley , CA (US ) ; Eric (52 ) U.S. CI. M. Paradise , Vienna , VA (US ) CPC C12P 5/007 ( 2013.01) ; C12N 9/1085 ( 2013.01 ) ; C12N 15/81 ( 2013.01 ) ; C12P 23/00 ( 2013.01 ); C12Y 402/03024 ( 2013.01) ; C12N ( 21) Appl. No .: 16 /554,125 9/88 ( 2013.01 ) ; C12Y 101/01034 (2013.01 ) ; C12Y 205/01092 (2013.01 ) ; C12N 9/0006 ( 2013.01) ( 22 ) Filed : Aug. 28 , 2019 (57 ) ABSTRACT The present invention provides genetically modified eukary otic host cells that produce isoprenoid precursors or iso Related U.S. Application Data prenoid compounds. A subject genetically modified host cell ( 63 ) Continuation of application No. 15/ 722,844 , filed on comprises increased activity levels of one or more of Oct. 2 , 2017 , now Pat . No. 10,435,717 , which is a mevalonate pathway enzymes , increased levels of prenyl continuation of application No. 14 /451,056 , filed on transferase activity , and decreased levels of squalene syn Aug. 4 , 2014 , now Pat. No. 9,809,829 , which is a thase activity . -
Terpene and Isoprenoid Biosynthesis in Cannabis Sativa
TERPENE AND ISOPRENOID BIOSYNTHESIS IN CANNABIS SATIVA by Judith Booth B.Sc., The University of King’s College, 2012 A THESIS SUBMITTED IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR THE DEGREE OF DOCTOR OF PHILOSOPHY in The Faculty of Graduate and Postdoctoral Studies (Genome Science and Technology) THE UNIVERSITY OF BRITISH COLUMBIA (Vancouver) September 2020 © Judith Booth, 2020 The following individuals certify that they have read, and recommend to the Faculty of Graduate and Postdoctoral Studies for acceptance, the dissertation entitled: Terpene and Isoprenoid Biosynthesis in Cannabis sativa submitted by Judith Booth in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Genome Science and Technology Examining Committee: Dr. Joerg Bohlmann, Professor, Michael Smith Laboratories, UBC Supervisor Dr. Anne Lacey Samuels, Professor, Botany, UBC Supervisory Committee Member Dr. Murray Isman, Professor Emeritus, Land and Food Systems, UBC University Examiner Dr. Corey Nislow, Professor, Biochemistry and Molecular Biology, UBC University Examiner Additional Supervisory Committee Members: Dr. Jonathan Page, Adjunct Professor, Botany, UBC Supervisory Committee Member Dr. Reinhard Jetter, Professor, Professor, Botany, UBC Supervisory Committee Member ii Abstract Cannabis sativa (cannabis, marijuana, hemp) is a plant species grown widely for its psychoactive and medicinal properties. Cannabis products were made illegal in most of the world in the early 1900s, but regulations have recently been relaxed or lifted in some jurisdictions, notably Canada and parts of the United States. Cannabis is usually grown for the resin produced in trichomes on the flowers of female plants. The major components of that resin are isoprenoids: cannabinoids, monoterpenes, and sesquiterpenes. Terpene profiles in cannabis flowers can vary widely between cultivars. -
Functional Characterization of Myrcene Hydroxylases from Two Geographically Distinct Ips Pini Populations
Insect Biochemistry and Molecular Biology 43 (2013) 336e343 Contents lists available at SciVerse ScienceDirect Insect Biochemistry and Molecular Biology journal homepage: www.elsevier.com/locate/ibmb Functional characterization of myrcene hydroxylases from two geographically distinct Ips pini populations Minmin Song a, Amy C. Kim a, Andrew J. Gorzalski a, Marina MacLean a, Sharon Young a, Matthew D. Ginzel b, Gary J. Blomquist a, Claus Tittiger a,* a Department of Biochemistry and Molecular Biology, University of Nevada, Reno, NV 89557, USA b Departments of Entomology and Forestry and Natural Resources, Purdue University, West Lafayette, IN 47907, USA article info abstract Article history: Ips pini bark beetles use myrcene hydroxylases to produce the aggregation pheromone component, Received 12 July 2012 ipsdienol, from myrcene. The enantiomeric ratio of pheromonal ipsdienol is an important prezygotic Received in revised form mating isolation mechanism of I. pini and differs among geographically distinct populations. We explored 7 January 2013 the substrate and product ranges of myrcene hydroxylases (CYP9T2 and CYP9T3) from reproductively- Accepted 15 January 2013 isolated western and eastern I. pini. The two cytochromes P450 share 94% amino acid identity. CYP9T2 mRNA levels were not induced in adults exposed to myrcene-saturated atmosphere. Functional assays Keywords: of recombinant enzymes showed both hydroxylated myrcene, (þ)- and (À)-a-pinene, 3-carene, and Cytochrome P450 þ À Monoterpene R-( )-limonene, but not a-phellandrene, ( )-b-pinene, g-terpinene, or terpinolene, with evidence that Pheromone CYP9T2 strongly preferred myrcene over other substrates. They differed in the enantiomeric ratios of Detoxification ipsdienol produced from myrcene, and in the products resulting from different a-pinene enantiomers.