Genomic Organization of Plant Terpene Synthases and Molecular Evolutionary Implications
TL;DR: A model presented for the evolutionary history of plant terpenoid synthases suggests that this superfamily of genes responsible for natural products biosynthesis derived from terpene synthase genes involved in primary metabolism by duplication and divergence in structural and functional specialization.
Abstract: Terpenoids are the largest, most diverse class of plant natural products and they play numerous functional roles in primary metabolism and in ecological interactions. The first committed step in the formation of the various terpenoid classes is the transformation of the prenyl diphosphate precursors, geranyl diphosphate, farnesyl diphosphate, and geranylgeranyl diphosphate, to the parent structures of each type catalyzed by the respective monoterpene (C(10)), sesquiterpene (C(15)), and diterpene synthases (C(20)). Over 30 cDNAs encoding plant terpenoid synthases involved in primary and secondary metabolism have been cloned and characterized. Here we describe the isolation and analysis of six genomic clones encoding terpene synthases of conifers, [(-)-pinene (C(10)), (-)-limonene (C(10)), (E)-alpha-bisabolene (C(15)), delta-selinene (C(15)), and abietadiene synthase (C(20)) from Abies grandis and taxadiene synthase (C(20)) from Taxus brevifolia], all of which are involved in natural products biosynthesis. Genome organization (intron number, size, placement and phase, and exon size) of these gymnosperm terpene synthases was compared to eight previously characterized angiosperm terpene synthase genes and to six putative terpene synthase genomic sequences from Arabidopsis thaliana. Three distinct classes of terpene synthase genes were discerned, from which assumed patterns of sequential intron loss and the loss of an unusual internal sequence element suggest that the ancestral terpenoid synthase gene resembled a contemporary conifer diterpene synthase gene in containing at least 12 introns and 13 exons of conserved size. A model presented for the evolutionary history of plant terpene synthases suggests that this superfamily of genes responsible for natural products biosynthesis derived from terpene synthase genes involved in primary metabolism by duplication and divergence in structural and functional specialization. This novel molecular evolutionary approach focused on genes of secondary metabolism may have broad implications for the origins of natural products and for plant phylogenetics in general.
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TL;DR: Particular focus will be placed on phytocannabinoid‐terpenoid interactions that could produce synergy with respect to treatment of pain, inflammation, depression, anxiety, addiction, epilepsy, cancer, fungal and bacterial infections (including methicillin‐resistant Staphylococcus aureus).
Abstract: Tetrahydrocannabinol (THC) has been the primary focus of cannabis research since 1964, when Raphael Mechoulam isolated and synthesized it. More recently, the synergistic contributions of cannabidiol to cannabis pharmacology and analgesia have been scientifically demonstrated. Other phytocannabinoids, including tetrahydrocannabivarin, cannabigerol and cannabichromene, exert additional effects of therapeutic interest. Innovative conventional plant breeding has yielded cannabis chemotypes expressing high titres of each component for future study. This review will explore another echelon of phytotherapeutic agents, the cannabis terpenoids: limonene, myrcene, α-pinene, linalool, β-caryophyllene, caryophyllene oxide, nerolidol and phytol. Terpenoids share a precursor with phytocannabinoids, and are all flavour and fragrance components common to human diets that have been designated Generally Recognized as Safe by the US Food and Drug Administration and other regulatory agencies. Terpenoids are quite potent, and affect animal and even human behaviour when inhaled from ambient air at serum levels in the single digits ng·mL−1. They display unique therapeutic effects that may contribute meaningfully to the entourage effects of cannabis-based medicinal extracts. Particular focus will be placed on phytocannabinoid-terpenoid interactions that could produce synergy with respect to treatment of pain, inflammation, depression, anxiety, addiction, epilepsy, cancer, fungal and bacterial infections (including methicillin-resistant Staphylococcus aureus). Scientific evidence is presented for non-cannabinoid plant components as putative antidotes to intoxicating effects of THC that could increase its therapeutic index. Methods for investigating entourage effects in future experiments will be proposed. Phytocannabinoid-terpenoid synergy, if proven, increases the likelihood that an extensive pipeline of new therapeutic products is possible from this venerable plant.
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This article is part of a themed issue on Cannabinoids in Biology and Medicine. To view the other articles in this issue visit http://dx.doi.org/10.1111/bph.2011.163.issue-7
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Cites background from "Genomic Organization of Plant Terpe..."
...One important remaining order of business is the elucidation of mono- and sesquiterpenoid biosynthetic pathways in cannabis, as has been achieved previously in other species of plants (Croteau, 1987; Gershenzon and Croteau, 1993; Bohlmann et al., 1998; Turner et al., 1999; Trapp and Croteau, 2001)....
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...…important remaining order of business is the elucidation of mono- and sesquiterpenoid biosynthetic pathways in cannabis, as has been achieved previously in other species of plants (Croteau, 1987; Gershenzon and Croteau, 1993; Bohlmann et al., 1998; Turner et al., 1999; Trapp and Croteau, 2001)....
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TL;DR: This review focuses on the functions of plant volatiles, their biosynthesis and regulation, and the metabolic engineering of the volatile spectrum, which results in plant defense improvement and changes of scent and aroma properties of flowers and fruits.
Abstract: Volatile compounds act as a language that plants use for their communication and interaction with the surrounding environment. To date, a total of 1700 volatile compounds have been isolated from more than 90 plant families. These volatiles, released from leaves, flowers, and fruits into the atmosphere and from roots into the soil, defend plants against herbivores and pathogens or provide a reproductive advantage by attracting pollinators and seed dispersers. Plant volatiles constitute about 1% of plant secondary metabolites and are mainly represented by terpenoids, phenylpropanoids/benzenoids, fatty acid derivatives, and amino acid derivatives. In this review we focus on the functions of plant volatiles, their biosynthesis and regulation, and the metabolic engineering of the volatile spectrum, which results in plant defense improvement and changes of scent and aroma properties of flowers and fruits.
1,090 citations
Cites background from "Genomic Organization of Plant Terpe..."
...They belong to the terpene synthase (TPS) gene family, which has been divided into seven subfamilies (designated TPS-a through TPS-g) based on sequence relatedness, functional assessment, and gene architecture (Figure 4) (Bohlmann et al., 1998; Trapp and Croteau, 2001; Aubourg et al., 2002; Martin et al., 2004)....
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...…the terpene synthase (TPS) gene family, which has been divided into seven subfamilies (designated TPS-a through TPS-g) based on sequence relatedness, functional assessment, and gene architecture (Figure 4) (Bohlmann et al., 1998; Trapp and Croteau, 2001; Aubourg et al., 2002; Martin et al., 2004)....
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TL;DR: The terpene synthases (TPSs) as mentioned in this paper are a family of enzymes responsible for the synthesis of various terpenes from two isomeric 5-carbon precursor molecules, leading to 5-carbinear isoprene, 10-carbon monoterpenes, 15-carbon sesquiterpenes and 20-carbenes.
Abstract: Summary
Some plant terpenes such as sterols and carotenes are part of primary metabolism and found essentially in all plants. However, the majority of the terpenes found in plants are classified as ‘secondary’ compounds, those chemicals whose synthesis has evolved in plants as a result of selection for increased fitness via better adaptation to the local ecological niche of each species. Thousands of such terpenes have been found in the plant kingdom, but each species is capable of synthesizing only a small fraction of this total. In plants, a family of terpene synthases (TPSs) is responsible for the synthesis of the various terpene molecules from two isomeric 5-carbon precursor ‘building blocks’, leading to 5-carbon isoprene, 10-carbon monoterpenes, 15-carbon sesquiterpenes and 20-carbon diterpenes. The bryophyte Physcomitrella patens has a single TPS gene, copalyl synthase/kaurene synthase (CPS/KS), encoding a bifunctional enzyme producing ent-kaurene, which is a precursor of gibberellins. The genome of the lycophyte Selaginella moellendorffii contains 18 TPS genes, and the genomes of some model angiosperms and gymnosperms contain 40–152 TPS genes, not all of them functional and most of the functional ones having lost activity in either the CPS- or KS-type domains. TPS genes are generally divided into seven clades, with some plant lineages having a majority of their TPS genes in one or two clades, indicating lineage-specific expansion of specific types of genes. Evolutionary plasticity is evident in the TPS family, with closely related enzymes differing in their product profiles, subcellular localization, or the in planta substrates they use.
990 citations
TL;DR: This review covers the monoterpene and sesquiterpene synthases presenting an up-to-date list of enzymes reported and evidence for their ability to form multiple products.
857 citations
Cites background from "Genomic Organization of Plant Terpe..."
...AAX69064 b-Myrcene ( 50) LeMTS2 Lycopersicon esculentum None van Schie et al. (2007) ACC66282 a-Terpineol (100) Mg17 Magnolia grandiflora 1–6, $ Lee and Chappell (2008) AAP40638 Inactive – Melaleuca alternifolia Shelton et al....
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TL;DR: In conclusion, oxidative and thermal stresses are relieved in the presence of volatile terpenes and C6 compounds, and methyl salicylate are thought to promote direct and indirect defence by modulating the signalling that biochemically activate defence pathways.
823 citations
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15 Jan 2001
TL;DR: Molecular Cloning has served as the foundation of technical expertise in labs worldwide for 30 years as mentioned in this paper and has been so popular, or so influential, that no other manual has been more widely used and influential.
Abstract: Molecular Cloning has served as the foundation of technical expertise in labs worldwide for 30 years. No other manual has been so popular, or so influential. Molecular Cloning, Fourth Edition, by the celebrated founding author Joe Sambrook and new co-author, the distinguished HHMI investigator Michael Green, preserves the highly praised detail and clarity of previous editions and includes specific chapters and protocols commissioned for the book from expert practitioners at Yale, U Mass, Rockefeller University, Texas Tech, Cold Spring Harbor Laboratory, Washington University, and other leading institutions. The theoretical and historical underpinnings of techniques are prominent features of the presentation throughout, information that does much to help trouble-shoot experimental problems. For the fourth edition of this classic work, the content has been entirely recast to include nucleic-acid based methods selected as the most widely used and valuable in molecular and cellular biology laboratories. Core chapters from the third edition have been revised to feature current strategies and approaches to the preparation and cloning of nucleic acids, gene transfer, and expression analysis. They are augmented by 12 new chapters which show how DNA, RNA, and proteins should be prepared, evaluated, and manipulated, and how data generation and analysis can be handled. The new content includes methods for studying interactions between cellular components, such as microarrays, next-generation sequencing technologies, RNA interference, and epigenetic analysis using DNA methylation techniques and chromatin immunoprecipitation. To make sense of the wealth of data produced by these techniques, a bioinformatics chapter describes the use of analytical tools for comparing sequences of genes and proteins and identifying common expression patterns among sets of genes. Building on thirty years of trust, reliability, and authority, the fourth edition of Mol
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TL;DR: A new approach to rapid sequence comparison, basic local alignment search tool (BLAST), directly approximates alignments that optimize a measure of local similarity, the maximal segment pair (MSP) score.
88,255 citations
TL;DR: A new criterion for triggering the extension of word hits, combined with a new heuristic for generating gapped alignments, yields a gapped BLAST program that runs at approximately three times the speed of the original.
Abstract: The BLAST programs are widely used tools for searching protein and DNA databases for sequence similarities. For protein comparisons, a variety of definitional, algorithmic and statistical refinements described here permits the execution time of the BLAST programs to be decreased substantially while enhancing their sensitivity to weak similarities. A new criterion for triggering the extension of word hits, combined with a new heuristic for generating gapped alignments, yields a gapped BLAST program that runs at approximately three times the speed of the original. In addition, a method is introduced for automatically combining statistically significant alignments produced by BLAST into a position-specific score matrix, and searching the database using this matrix. The resulting Position-Specific Iterated BLAST (PSIBLAST) program runs at approximately the same speed per iteration as gapped BLAST, but in many cases is much more sensitive to weak but biologically relevant sequence similarities. PSI-BLAST is used to uncover several new and interesting members of the BRCT superfamily.
70,111 citations
Book•
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01 Jan 1989
TL;DR: To develop a program to print the barcodes using two commonly uses command sets and hence evaluates their ease of use for such applications, students should be able to program dot matrix printers, by manipulating bit level information and ink jet printers using page description language, such as PCL.
Abstract: 1. OBJECTIVE To develop a program to print the barcodes using two commonly uses command sets and hence evaluates their ease of use for such applications. Upon completion of this experiment, students should be able to program dot matrix printers, by manipulating bit level information and ink jet printers using page description language, such as PCL which uses raster image for graphics output. Students will also become familiar with the encoding and dimensional requirements of barcode symbologies, and the suitability of the selected printers for barcode printing. The Computer Engineering Laboratory is set up with IBM-compatible PC's installed with standard C compiler. The laboratory also has several kinds of printers for this experiment. They are classified into two groups. One group consists of dot-matrix printers and the other group consists of HP ink jet printers. In this experiment, each student will have to program a dot-matrix printer using Epson 9-pin graphics command codes in group A printers and HP PCL graphics commands for the ink jet printer in group B. The assignment of different printers is as follows: 4. INTRODUCTION Barcode labelling is widely implemented in the retail marketplace and is gaining increasing visibility in a broad range of non-retail applications. To read the information contained in a barcode symbol, a scanning device such as a wand can be used. As the scanning device is moved across the symbol, the width pattern of the bars and the spaces is analysed by the reading equipment and the original data is recovered. A number of barcodes has been developed over the years, these include UPS, interleaved 2 of 5, rationalised codabar, code 39, code 128, code 93 and code 49. The American format for article numbering is the Universal Product Code (UPC). The UPC has been successfully employed in the supermarket industry since 1973. It is designed to uniquely identify a product and its manufacturer. Refer to Appendix A for UPC specifications which are necessary for this experiment. Barcode symbols can be printed with various printing technologies and on a variety of substrate labels, tags and papers. In this experiment, plain paper will be used. Hence, the quality of printed barcode will only depend on the printing mechanism. In this experiment, students will learn to program dot matrix printers by manipulating bit level information. A brief summary of the commonly used commands is attached in Appendix B and abstract from the manuals …
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2,699 citations
"Genomic Organization of Plant Terpe..." refers background in this paper
...…classified alternative, pyruvate/glyceraldehyde-3-phosphate pathas secondary metabolites, compounds not required for way (Eisenreich et al. 1998; Lichtenthaler 1999), by plant growth and development but presumed to have which the monoterpenes (C10), diterpenes (C20), and an ecological function…...
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