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Biosynthesis and Functions of Terpenoids in Plants
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Biosynthesis and Functions of Terpenoids in Plants

A special issue of Plants (ISSN 2223-7747). This special issue belongs to the section "Phytochemistry".

Deadline for manuscript submissions: closed (31 August 2020) | Viewed by 38833

Special Issue Editor

Dr. Isabel Nogués

E-Mail Website
Guest Editor
Research Institute on Terrestrial Ecosystems, CNR, Via Salaria Km. 29,300, 00015 Monterotondo Scalo, Rome, Italy
Interests: plant physiology; plant biochemistry; terpenoids; plant defense; abiotic stress; antioxidants

Special Issue Information

Dear Colleagues,

Terpenes and derived terpenoids, also known as isoprenoids, are the largest class of plant secondary metabolites, with basic functions in growth and development, and more specialized roles in plant–environment interactions, resistance/tolerance to environmental stresses, and defence against predators and pathogens. Moreover, many terpenoids have been reported to have antimicrobial, anti-inflammatory and antioxidant properties making them of great interest in the medical field. Moreover, they are widely used as natural flavouring compounds in the food and fragrances industries, and more recently, as a source of biofuels.

Their biosynthesis may be constitutive or provoked/enhanced by biotic or abiotic stresses and starts with the synthesis of the five-carbon precursor, isopentenyl diphosphate (IPP), and of its isomer, dimethylallyl diphosphate (DMAPP). Through repeated condensations of these five-carbon units by prenyltransferases, rearrangement by terpene synthases and cyclization reactions, the different classes of terpenoids are produced: C5 isoprene, C10 monoterpenoids, C15 sesquiterpenoids, C20 diterpenoids, C25 sesterterpenoids, C30 triterpenoids, C40 tetraterpenoids, and C >40 polyterpenoids.

This Special Issue will be dedicated to the study of the different types of terpenes and terpenoids in plants. In particular, we invite manuscripts on terpenoids biosynthesis, regulation and functions/applications in plants. All studies, including research papers and reviews related to these items, will be considered for publication.

Dr. Isabel Nogués
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Plants is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Isoprene
  • MVA pathway
  • MEP pathway
  • Terpene synthase
  • Photosynthesis
  • Volatiles
  • Plant defense
  • Plant-environment interactions
  • Biotic and abiotic stresses

Published Papers (9 papers)

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Research

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18 pages, 2837 KiB  
Article
Identification of Three Monofunctional Diterpene Synthases with Specific Enzyme Activities Expressed during Heartwood Formation in Western Redcedar (Thuja plicata) Trees
by Sifat Tasnim, Regine Gries and Jim Mattsson
Plants 2020, 9(8), 1018; https://doi.org/10.3390/plants9081018 - 12 Aug 2020
Cited by 7 | Viewed by 4113
Abstract
Upon harvest, Western redcedar (WRC; Thuja plicata) trees have a high incidence and extent of heartwood rot. While monoterpenoids and lignans have been linked to rot resistance in this species, other specialized metabolites, such as diterpenes, are likely to contribute to rot [...] Read more.
Upon harvest, Western redcedar (WRC; Thuja plicata) trees have a high incidence and extent of heartwood rot. While monoterpenoids and lignans have been linked to rot resistance in this species, other specialized metabolites, such as diterpenes, are likely to contribute to rot resistance. Here we report the cloning and functional assessment of three putative diterpene synthase (TpdiTPS) genes expressed during heartwood formation in WRC. The predicted proteins of the three genes lack either of the two catalytically independent active sites typical of most diTPS, indicating monofunctional rather than bifunctional activity. To identify potential catalytic activities of these proteins, we expressed them in genetically engineered Escherichia coli strains that produce four potential substrates, geranylgeranyl diphosphate (GGDP), ent, syn, and normal stereoisomers of copalyl diphosphate (CDP). We found that TpdiTPS3 used GGDP to produce CDP. TpdiTPS2 used normal CDP to produce levopimaradiene. TpdiTPS1 showed stereoselectivity as it used normal CDP to produce sandaracopimaradiene and syn-CDP to produce syn-stemod-13(17)-ene. These genes and protein enzymatic activities have not been previously reported in WRC and provide an opportunity to assess their potential roles in heartwood rot resistance in this economically important species. Full article
(This article belongs to the Special Issue Biosynthesis and Functions of Terpenoids in Plants)
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19 pages, 2946 KiB  
Article
Effects of Soil Fertilization on Terpenoids and Other Carbon-Based Secondary Metabolites in Rosmarinus officinalis Plants: A Comparative Study
by Maria Ángeles Bustamante, Marco Michelozzi, Anna Barra Caracciolo, Paola Grenni, Janine Verbokkem, Peter Geerdink, Carl Safi and Isabel Nogues
Plants 2020, 9(7), 830; https://doi.org/10.3390/plants9070830 - 02 Jul 2020
Cited by 24 | Viewed by 4113
Abstract
Rosmarinus officinalis is an evergreen aromatic plant with important commercial interest as it contains numerous essential oils (composed of terpenoid compounds) and phenolic constituents (natural antioxidant compounds). This work aims at evaluating the concomitant effects of different inorganic and organic fertilization treatments and [...] Read more.
Rosmarinus officinalis is an evergreen aromatic plant with important commercial interest as it contains numerous essential oils (composed of terpenoid compounds) and phenolic constituents (natural antioxidant compounds). This work aims at evaluating the concomitant effects of different inorganic and organic fertilization treatments and the subsequent increases in soil nutrient availability on terpenoids and other carbon-based secondary metabolites, e.g., flavonoids and phenolic compounds, in Rosmarinus officinalis leaves. The results showed that, as expected, the structural carbohydrate content (lignocellulosic compounds) in stems was higher in fertilized plants than in controls. Additionally, positive correlations were observed of the absolute amounts of total terpenoids and some single terpenoid compounds with N or P contents in leaves. On the contrary, the phenolic and flavonoid concentrations in all the rosemary plant parts were lower with the fertilization treatments. Indeed, negative correlations between the phenolic compounds (and flavonoids) and N in rosemary leaves were also found. Overall, the results suggest that the terpenoid production’s response to fertilization was due to N, which is essential for protein synthesis and terpene synthase activity, and to P, which is necessary for the synthesis of both terpenoid precursors and ATP and NADPH, also needed for terpenoid synthesis. On the other hand, the basis for the fertilization’s effects on the production of phenolic compounds is the direct nitrogen trade-off between growth and the shikimic acid pathway by which phenolics compounds are synthesized. Full article
(This article belongs to the Special Issue Biosynthesis and Functions of Terpenoids in Plants)
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21 pages, 6459 KiB  
Article
Molecular Cloning and Functional Characterization of CpMYC2 and CpBHLH13 Transcription Factors from Wintersweet (Chimonanthus praecox L.)
by Muhammad Zeshan Aslam, Xiang Lin, Xiang Li, Nan Yang and Longqing Chen
Plants 2020, 9(6), 785; https://doi.org/10.3390/plants9060785 - 23 Jun 2020
Cited by 24 | Viewed by 3602
Abstract
Wintersweet (Chimonanthus praecox L.) is an ornamental and economically significant shrub known for its unique flowering characteristics, especially the emission of abundant floral volatile organic compounds. Thus, an understanding of the molecular mechanism of the production of these compounds is necessary to [...] Read more.
Wintersweet (Chimonanthus praecox L.) is an ornamental and economically significant shrub known for its unique flowering characteristics, especially the emission of abundant floral volatile organic compounds. Thus, an understanding of the molecular mechanism of the production of these compounds is necessary to create new breeds with high volatile production. In this study, two bHLH transcription factors (CpMYC2 and CpbHLH13) of Wintersweet H29 were functionally characterized to illustrate their possible role in the production of volatile compounds. The qRT-PCR results showed that the expression of CpMYC2 and CpbHLH13 increased from the flower budding to full bloom stage, indicating that these two genes may play an essential role in blooming and aroma production in wintersweet. Gas chromatography-mass spectroscopy (GC-MS) analysis revealed that the overexpression of CpMYC2 in arabidopsis (Arabidopsis thaliana) AtMYC2-2 mutant (Salk_083483) and tobacco (Nicotiana tabaccum) genotype Petit Havana SR1 significantly increased floral volatile monoterpene, especially linalool, while the overexpression of CpbHLH13 in Arabidopsis thaliana ecotype Columbia-0 (Col-0) and tobacco genotype SR1 increased floral sesquiterpene β-caryophyllene production in both types of transgenic plants respectively. High expression of terpene synthase (TPS) genes in transgenic A. thaliana along with high expression of CpMYC2 and CpbHLH13 in transgenic plants was also observed. The application of a combination of methyl jasmonic acid (MeJA) and gibberellic acid (GA3) showed an increment in linalool production in CpMYC2-overexpressing arabidopsis plants, and the high transcript level of TPS genes also suggested the involvement of CpMYC2 in the jasmonic acid (JA) signaling pathway. These results indicate that both the CpMYC2 and CpbHLH13 transcription factors of wintersweet are possibly involved in the positive regulation and biosynthesis of monoterpene (linalool) and sesquiterpene (β-caryophyllene) in transgenic plants. This study also indicates the potential application of wintersweet as a valuable genomic material for the genetic modification of floral scent in other flowering plants that produce less volatile compounds. Full article
(This article belongs to the Special Issue Biosynthesis and Functions of Terpenoids in Plants)
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13 pages, 4114 KiB  
Article
Identification and Molecular Characterization of Geranyl Diphosphate Synthase (GPPS) Genes in Wintersweet Flower
by Hafiz Muhammad Kamran, Syed Bilal Hussain, Shang Junzhong, Lin Xiang and Long-Qing Chen
Plants 2020, 9(5), 666; https://doi.org/10.3390/plants9050666 - 24 May 2020
Cited by 12 | Viewed by 4005
Abstract
Geranyl diphosphate synthase (GPPS) is a plastid localized enzyme that catalyzes the biosynthesis of Geranyl diphosphate (GPP), which is a universal precursor of monoterpenes. Wintersweet (Chimonanthus praecox L.), a famous deciduous flowering shrub with a strong floral scent character, could have GPPS-like [...] Read more.
Geranyl diphosphate synthase (GPPS) is a plastid localized enzyme that catalyzes the biosynthesis of Geranyl diphosphate (GPP), which is a universal precursor of monoterpenes. Wintersweet (Chimonanthus praecox L.), a famous deciduous flowering shrub with a strong floral scent character, could have GPPS-like homologs that are involved in monoterpenes biosynthesis, but it remains unclear. In the present study, five full-length GPPS and geranylgeranyl diphosphate synthases (GGPPS) genes were identified in the wintersweet transcriptome database. The isolated cDNAs showed high protein sequence similarity with the other plants GPPS and GGPPS. The phylogenetic analysis further classified these cDNAs into four distinct clades, representing heterodimeric GPPS small subunits (SSU1 and SSU2), homodimeric GPPS, and GGPPS. Analysis of temporal expression revealed that all genes have the highest transcript level at the full-open flower stage. From tissue-specific expression analysis, CpGPPS.SSU1 and CpGGPPS1 were predominantly expressed in petal and flower, whereas CpGPPS.SSU2, GPPS, and GGPPS2 showed a constitutive expression. Additionally, the subcellular localization assay identified the chloroplast localization of SSUs and GGPPSs proteins, and the yeast two-hybrid assay showed that both CpGPPS.SSU1 and CpGPPS.SSU2 can interact with the GGPPS proteins. Taken together, these preliminary results suggest that the heterodimeric GPPS can regulate floral scent biosynthesis in wintersweet flower. Full article
(This article belongs to the Special Issue Biosynthesis and Functions of Terpenoids in Plants)
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12 pages, 1696 KiB  
Article
The Product Specificities of Maize Terpene Synthases TPS4 and TPS10 Are Determined Both by Active Site Amino Acids and Residues Adjacent to the Active Site
by Tobias G. Köllner, Jörg Degenhardt and Jonathan Gershenzon
Plants 2020, 9(5), 552; https://doi.org/10.3390/plants9050552 - 26 Apr 2020
Cited by 7 | Viewed by 3745
Abstract
Terpene synthases make up a large family of enzymes that convert prenyl diphosphates into an enormous variety of terpene skeletons. Due to their electrophilic reaction mechanism—which involves the formation of carbocations followed by hydride shifts and skeletal rearrangements—terpene synthases often produce complex mixtures [...] Read more.
Terpene synthases make up a large family of enzymes that convert prenyl diphosphates into an enormous variety of terpene skeletons. Due to their electrophilic reaction mechanism—which involves the formation of carbocations followed by hydride shifts and skeletal rearrangements—terpene synthases often produce complex mixtures of products. In the present study, we investigate amino acids that determine the product specificities of the maize terpene synthases TPS4 and TPS10. The enzymes showed 57% amino acid similarity and produced different mixtures of sesquiterpenes. Sequence comparisons and structure modeling revealed that out of the 43 amino acids forming the active site cavity, 17 differed between TPS4 and TPS10. While combined mutation of these 17 residues in TPS4 resulted in an enzyme with a product specificity similar to TPS10, the additional mutation of two amino acids next to the active site led to a nearly complete conversion of TPS4 into TPS10. These data demonstrate that the different product specificities of TPS4 and TPS10 are determined not only by amino acids forming the active site cavity, but also by neighboring residues that influence the conformation of active site amino acids. Full article
(This article belongs to the Special Issue Biosynthesis and Functions of Terpenoids in Plants)
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18 pages, 1890 KiB  
Article
Effects of NtSPS1 Overexpression on Solanesol Content, Plant Growth, Photosynthesis, and Metabolome of Nicotiana tabacum
by Ning Yan, Xiaolei Gai, Lin Xue, Yongmei Du, John Shi and Yanhua Liu
Plants 2020, 9(4), 518; https://doi.org/10.3390/plants9040518 - 17 Apr 2020
Cited by 3 | Viewed by 2284
Abstract
Nicotiana tabacum solanesyl diphosphate synthase 1 (NtSPS1) is the key enzyme in solanesol biosynthesis. However, changes in the solanesol content, plant growth, photosynthesis, and metabolome of tobacco plants after NtSPS1 overexpression (OE) have not been previously reported. In the present study, these parameters, [...] Read more.
Nicotiana tabacum solanesyl diphosphate synthase 1 (NtSPS1) is the key enzyme in solanesol biosynthesis. However, changes in the solanesol content, plant growth, photosynthesis, and metabolome of tobacco plants after NtSPS1 overexpression (OE) have not been previously reported. In the present study, these parameters, as well as photosynthetic gas exchange, chlorophyll content, and chlorophyll fluorescence parameters, were compared between NtSPS1 OE and wild type (WT) lines of tobacco. As expected, NtSPS1 OE significantly increased solanesol content in tobacco leaves. Although NtSPS1 OE significantly increased leaf growth, photosynthesis, and chlorophyll content, the chlorophyll fluorescence parameters in the leaves of the NtSPS1 OE lines were only slightly higher than those in the WT leaves. Furthermore, NtSPS1 OE resulted in 64 differential metabolites, including 30 up-regulated and 34 down-regulated metabolites, between the OE and WT leaves. Pathway enrichment analysis of these differential metabolites identified differentially enriched pathways between the OE and WT leaves, e.g., carbon fixation in photosynthetic organisms. The maximum carboxylation rate of RuBisCO and the maximum rate of RuBP regeneration were also elevated in the NtSPS1 OE line. To our knowledge, this is the first study to confirm the role of NtSPS1 in solanesol biosynthesis and its possible functional mechanisms in tobacco. Full article
(This article belongs to the Special Issue Biosynthesis and Functions of Terpenoids in Plants)
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14 pages, 4774 KiB  
Article
Exogenous Isoprene Confers Physiological Benefits in a Negligible Isoprene Emitter (Acer monspessulanum L.) under Water Deficit
by Elena Ormeño, Justine Viros, Jean-Philippe Mévy, Alain Tonetto, Amélie Saunier, Anne Bousquet-Mélou and Catherine Fernandez
Plants 2020, 9(2), 159; https://doi.org/10.3390/plants9020159 - 28 Jan 2020
Cited by 12 | Viewed by 2974
Abstract
Isoprene, the main volatile released by plants, is known to protect the photosynthetic apparatus in isoprene emitters submitted to oxidative pressures caused by environmental constraints. Whether ambient isoprene contributes to protect negligible plant emitters under abiotic stress conditions is less clear, and no [...] Read more.
Isoprene, the main volatile released by plants, is known to protect the photosynthetic apparatus in isoprene emitters submitted to oxidative pressures caused by environmental constraints. Whether ambient isoprene contributes to protect negligible plant emitters under abiotic stress conditions is less clear, and no study has tested if ambient isoprene is beneficial during drought periods in plant species that naturally release negligible isoprene emissions. This study examines the effect of exogenous isoprene (20 ppbv) on net photosynthesis, stomatal conductance and production of H2O2 (a reactive oxygen species: ROS) in leaves of Acer monspessulanum (a negligible isoprene emitter) submitted to three watering treatments (optimal, moderate water stress and severe water stress). Results showed that A. monspessulanum exhibited a net photosynthesis increase (+30%) and a relative leaf H2O2 decrease when saplings were exposed to an enriched isoprene atmosphere compared to isoprene-free conditions under moderate water deficit. Such physiological improvement under isoprene exposure was not observed under optimal watering or severe water stress. These findings suggest that when negligible isoprene emitters are surrounded by a very high concentration of isoprene in the ambient air, some plant protection mechanism occurs under moderate water deficit probably related to protection against ROS damage eventually impeding photosynthesis drop. Full article
(This article belongs to the Special Issue Biosynthesis and Functions of Terpenoids in Plants)
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52 pages, 502 KiB  
Review
Phytotoxic Effects and Mechanism of Action of Essential Oils and Terpenoids
by Mercedes Verdeguer, Adela M. Sánchez-Moreiras and Fabrizio Araniti
Plants 2020, 9(11), 1571; https://doi.org/10.3390/plants9111571 - 13 Nov 2020
Cited by 91 | Viewed by 7931
Abstract
Weeds are one of the major constraints in crop production affecting both yield and quality. The excessive and exclusive use of synthetic herbicides for their management is increasing the development of herbicide-resistant weeds and is provoking risks for the environment and human health. [...] Read more.
Weeds are one of the major constraints in crop production affecting both yield and quality. The excessive and exclusive use of synthetic herbicides for their management is increasing the development of herbicide-resistant weeds and is provoking risks for the environment and human health. Therefore, the development of new herbicides with multitarget-site activity, new modes of action and low impact on the environment and health are badly needed. The study of plant–plant interactions through the release of secondary metabolites could be a starting point for the identification of new molecules with herbicidal activity. Essential oils (EOs) and their components, mainly terpenoids, as pure natural compounds or in mixtures, because of their structural diversity and strong phytotoxic activity, could be good candidates for the development of new bioherbicides or could serve as a basis for the development of new natural-like low impact synthetic herbicides. EOs and terpenoids have been largely studied for their phytotoxicity and several evidences on their modes of action have been highlighted in the last decades through the use of integrated approaches. The review is focused on the knowledge concerning the phytotoxicity of these molecules, their putative target, as well as their potential mode of action. Full article
(This article belongs to the Special Issue Biosynthesis and Functions of Terpenoids in Plants)

Other

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8 pages, 2007 KiB  
Brief Report
Plant Triterpenoid Crosstalk: The Interaction of Brassinosteroids and Phytoecdysteroids in Lepidium sativum
by Danuše Tarkowská, Eliška Krampolová and Miroslav Strnad
Plants 2020, 9(10), 1325; https://doi.org/10.3390/plants9101325 - 07 Oct 2020
Cited by 5 | Viewed by 1874
Abstract
Plant steroid alcohols, plant sterols, are essential components of cell membranes that perform many functions. Their most prominent function is maintaining membrane semipermeability and regulating its fluidity through their specific interaction with phospholipids and membrane proteins. This work is focused on the study [...] Read more.
Plant steroid alcohols, plant sterols, are essential components of cell membranes that perform many functions. Their most prominent function is maintaining membrane semipermeability and regulating its fluidity through their specific interaction with phospholipids and membrane proteins. This work is focused on the study of the interaction of two groups of plant sterols, brassinosteroids (BRs) and phytoecdysteroids (PE). Steroid substances belonging to both groups are important signaling molecules essential for plant growth and development, but while the first group has all the known attributes of plant hormones, the second lacks hormonal function in plants. The aim of this preliminary study was to determine at what concentration level and to what extent substances of this type are able to interact with each other, and thus influence the early growth and development of a plant. It was found that exogenously applied PE 20-hydroxyecdysone (20E) significantly reduced the level of endogenous BRs in four-day-old garden cress (Lepidium sativum) seedlings. On the other hand, exogenously applied BRs, 24-epibrassinolide (epiBL), caused the opposite effect. Endogenous 20E was further detected at the picogram level in garden cress seedlings. Thus, this is the first report indicating that this plant species is PE-positive. The level of endogenous 20E in garden cress seedlings can be decreased by exogenous epiBL, but only at a relatively high concentration of 1·10−6 M in a culture medium. The image analysis of garden cress seedlings revealed that the length of shoot is affected neither by exogenous BRs nor PE, whereas the root length varies depending on the type and concentration of steroid applied. Full article
(This article belongs to the Special Issue Biosynthesis and Functions of Terpenoids in Plants)
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