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A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Natural Products Chemistry".

Deadline for manuscript submissions: closed (30 September 2019) | Viewed by 58122

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Prof. Dr. Ewa Swiezewska

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Institute of Biochemistry and Biophysics, Polish Academy of Sciences, 02-106 Warsaw, Poland
Interests: biochemistry, genetics and molecular biology; agricultural and biological sciences; pharmacology, toxicology and pharmaceutics

Dr. Liliana Surmacz

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Special Issue Information

Dear Colleagues,

Isoprenoids called also terpenoids, are constituents of all living cells, but they are especially abundant in plant tissues. They constitute the most structurally (>50,000 compounds) and functionally diverse class of plant natural products, including both essential primary metabolites and a broad range of secondary metabolites - also termed ‘specialized’ to underline their vital functions in plant cells, e.g. as stress-responsive compounds, attractants, repellents, modulators of allelopathic interactions, etc. The profile of plant isoprenoids (the ‘terpenome’) is species- but also cell-type specific. Moreover, some isoprenoids are produced constitutively while the synthesis of others is induced in response to environmental cues. To maintain the required cellular balance of particular isoprenoids a precise and strictly regulated metabolic network exists. Last but not least, numerous applications of plant isoprenoids, e.g. as pharmaceuticals, fragrances, flavours, colorants, and dietary supplements, make them the most commercially exploited group of plant-derived natural products; to satisfy the demands of the market, efficient platforms producing isoprenoids are continuously being developed. Such efforts are preceded by the identification of the biosynthetic routes and regulatory mechanisms responsible for the biosynthesis of the compound(s) of interest. This Special Issue aims to present the latest achievements in the field of studies on metabolic routes and elucidations of function of plant isoprenoids.

Prof. Ewa Swiezewska
Assoc. Prof. Liliana Surmacz
Guest Editors

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Keywords

Isoprenoid primary and specialized metabolites of plants
Mevalonic acid (MVA) and methylerythritol phosphate (MEP) routes – isoprenoid producing pathways
Biosynthesis, metabolism and metabolomics of plant isoprenoids
Functions of plant isoprenoids
Isoprenoid-generating platforms

Published Papers (11 papers)

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Research

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20 pages, 3125 KiB

Open AccessFeature PaperArticle

Biosynthesis of Isoprene Units in Euphorbia lathyris Laticifers vs. Other Tissues: MVA and MEP Pathways, Compartmentation and Putative Endophytic Fungi Contribution

by Clément Gastaldo, Agata Lipko, Estelle Motsch, Pierre Adam, Philippe Schaeffer and Michel Rohmer

Molecules 2019, 24(23), 4322; https://doi.org/10.3390/molecules24234322 - 26 Nov 2019

Cited by 6 | Viewed by 4703

Abstract

Euphorbia species are characterized by a net of laticifers producing large amounts of triterpenes. These hydrocarbon-like metabolites can be converted into fuel by the methods of the oil industry. Euphorbia lathyris is easily grown at an industrial scale. In an attempt to increase its triterpene production, the metabolic pathways leading to isoprenoid were investigated by incorporation of ¹³C labeled glucose and mevalonate and ²H labeled deoxyxylulose as well as by natural abundance isotope ratio GC-MS. Latex triterpenes are exclusively synthesized via the mevalonate (MVA) pathway: this may orient future search for improving the triterpene production in E. lathyris. Phytosterols and their precursors are mainly derived from MVA pathway with a slight contribution of the methylerythritol phosphate (MEP) pathway, whereas phytol is issued from MEP pathway with a minor contribution of the MVA pathway: this is in accordance with the metabolic cross-talk between cytosolic and plastidial compartments in plants. In addition, hopenol B behaved differently from the other latex triterpenes. Its ¹³C isotope abundance after incorporation of ¹³C labeled glucose and its natural abundance δ²H signature clearly differed from those of the other latex triterpenes indicating another metabolic origin and suggesting that it may be synthesized by an endophytic fungus. Full article

(This article belongs to the Special Issue Plant Isoprenoids)

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17 pages, 2259 KiB

Open AccessArticle

Influence of Selected Abiotic Factors on Triterpenoid Biosynthesis and Saponin Secretion in Marigold (Calendula officinalis L.) in Vitro Hairy Root Cultures

by Abdulwadood Shakir Mahmood Alsoufi, Cezary Pączkowski, Marek Długosz and Anna Szakiel

Molecules 2019, 24(16), 2907; https://doi.org/10.3390/molecules24162907 - 10 Aug 2019

Cited by 24 | Viewed by 4326

Abstract

The aim of the study was the evaluation of the efficiency of selected abiotic elicitors, i.e., silver and cadmium ions, ultrasound, and UV-C irradiation, in the stimulation of triterpenoid biosynthesis, accumulation, and saponin secretion in Calendula officinalis hairy root cultures. Apart from the possible enhancement of triterpenoid production, the relationship between primary and secondary metabolism (represented respectively by sterols and pentacyclic triterpenes), modifications of the sterol compositional profile, and fluctuations in the total triterpenoid content were monitored in the performed experiments. The main phenomenon observed as a response to heavy metal treatment was the stimulation (up to 12-fold) of the secretion of saponins, accompanied by significant changes in sterol composition. Ultrasound stimulated the secretion of saponins (up to 11-fold); however, it exerted diverse influences on the triterpenoid content in hairy root tissue (stimulating or decreasing) depending on the duration of the exposure to the elicitor. UV-C radiation caused a slight increase in the content of both sterols and saponins in hairy root tissue, and stimulated saponin secretion up to 8.5-fold. The expected symptoms of the competition between the biosynthetic pathways of sterols and pentacyclic triterpenoids were less evident in reactions to abiotic stressors than those reported previously for biotic elicitors. Full article

(This article belongs to the Special Issue Plant Isoprenoids)

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14 pages, 5192 KiB

Open AccessFeature PaperArticle

Long-Chain Polyisoprenoids Are Synthesized by AtCPT1 in Arabidopsis thaliana

by Przemyslaw Surowiecki, Agnieszka Onysk, Katarzyna Manko, Ewa Swiezewska and Liliana Surmacz

Molecules 2019, 24(15), 2789; https://doi.org/10.3390/molecules24152789 - 31 Jul 2019

Cited by 11 | Viewed by 3215

Abstract

Arabidopsis roots accumulate a complex mixture of dolichols composed of three families, (i.e., short-, medium- and long-chain dolichols), but until now none of the cis-prenyltransferases (CPTs) predicted in the Arabidopsis genome has been considered responsible for their synthesis. In this report, using homo- and heterologous (yeast and tobacco) models, we have characterized the AtCPT1 gene (At2g23410) which encodes a CPT responsible for the formation of long-chain dolichols, Dol-18 to -23, with Dol-21 dominating, in Arabidopsis. The content of these dolichols was significantly reduced in AtCPT1 T-DNA insertion mutant lines and highly increased in AtCPT1-overexpressing plants. Similar to the majority of eukaryotic CPTs, AtCPT1 is localized to the endoplasmic reticulum (ER). Functional complementation tests using yeast rer2Δ or srt1Δ mutants devoid of medium- or long-chain dolichols, respectively, confirmed that this enzyme synthesizes long-chain dolichols, although the dolichol chains thus formed are somewhat shorter than those synthesized in planta. Moreover, AtCPT1 acts as a homomeric CPT and does not need LEW1 for its activity. AtCPT1 is the first plant CPT producing long-chain polyisoprenoids that does not form a complex with the NgBR/NUS1 homologue. Full article

(This article belongs to the Special Issue Plant Isoprenoids)

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12 pages, 3653 KiB

Open AccessArticle

Characterization of a Cis-Prenyltransferase from Lilium longiflorum Anther

by Jyun-Yu Yao, Kuo-Hsun Teng, Ming-Che Liu, Co-Shine Wang and Po-Huang Liang

Molecules 2019, 24(15), 2728; https://doi.org/10.3390/molecules24152728 - 26 Jul 2019

Cited by 3 | Viewed by 3150

Abstract

A group of prenyltransferases catalyze chain elongation of farnesyl diphosphate (FPP) to designated lengths via consecutive condensation reactions with specific numbers of isopentenyl diphosphate (IPP). cis-Prenyltransferases, which catalyze cis-double bond formation during IPP condensation, usually synthesize long-chain products as lipid carriers to mediate peptidoglycan biosynthesis in prokaryotes and protein glycosylation in eukaryotes. Unlike only one or two cis-prenyltransferases in bacteria, yeast, and animals, plants have several cis-prenyltransferases and their functions are less understood. As reported here, a cis-prenyltransferase from Lilium longiflorum anther, named LLA66, was expressed in Saccharomyces cerevisiae and characterized to produce C40/C45 products without the capability to restore the growth defect from Rer2-deletion, although it was phylogenetically categorized as a long-chain enzyme. Our studies suggest that evolutional mutations may occur in the plant cis-prenyltransferase to convert it into a shorter-chain enzyme. Full article

(This article belongs to the Special Issue Plant Isoprenoids)

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12 pages, 1679 KiB

Open AccessArticle

Oxidosqualene Cyclase Knock-Down in Latex of Taraxacum koksaghyz Reduces Triterpenes in Roots and Separated Natural Rubber

by Nicole van Deenen, Kristina Unland, Dirk Prüfer and Christian Schulze Gronover

Molecules 2019, 24(15), 2703; https://doi.org/10.3390/molecules24152703 - 25 Jul 2019

Cited by 10 | Viewed by 3858

Abstract

In addition to natural rubber (NR), several triterpenes are synthesized in laticifers of the Russian dandelion (Taraxacum koksaghyz). Detailed analysis of NR and resin contents revealed different concentrations of various pentacyclic triterpenes such as α-, β-amyrin and taraxasterol, which strongly affect the mechanical properties of the resulting rubber material. Therefore, the reduction of triterpene content would certainly improve the industrial applications of dandelion NR. We developed T. koksaghyz plants with reduced triterpene contents by tissue-specific downregulation of major laticifer-specific oxidosqualene cyclases (OSCs) by RNA interference, resulting in an almost 67% reduction in the triterpene content of NR. Plants of the T1 generation showed no obvious phenotypic changes and the rubber yield also remained unaffected. Hence, this study will provide a solid basis for subsequent modern breeding programs to develop Russian dandelion plants with low and stable triterpene levels. Full article

(This article belongs to the Special Issue Plant Isoprenoids)

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21 pages, 4120 KiB

Open AccessArticle

Integration of Metabolite Profiling and Transcriptome Analysis Reveals Genes Related to Volatile Terpenoid Metabolism in Finger Citron (C. medica var. sarcodactylis)

by Yaying Xu, Changqing Zhu, Changjie Xu, Jun Sun, Donald Grierson, Bo Zhang and Kunsong Chen

Molecules 2019, 24(14), 2564; https://doi.org/10.3390/molecules24142564 - 15 Jul 2019

Cited by 42 | Viewed by 5003

Abstract

Finger citron (Citrus medica var. sarcodactylis) is a popular ornamental tree and an important source of essential oils rich in terpenoids, but the mechanisms behind volatile formation are poorly understood. We investigated gene expression changes combined with volatile profiling of ten samples from three developing organs: flower, leaf, and fruit. A total of 62 volatiles were identified with limonene and γ-terpinene being the most abundant ones. Six volatiles were identified using partial least squares discriminant analysis (PLS-DA) that could be used as markers for distinguishing finger citron from other citrus species. RNA-Seq revealed 1,611,966,118 high quality clean reads that were assembled into 32,579 unigenes. From these a total of 58 terpene synthase (TPS) gene family members were identified and the spatial and temporal distribution of their transcripts was measured in developing organs. Transcript levels of transcription factor genes AP2/ERF (251), bHLH (169), bZIP (76), MYB (155), NAC (184), and WRKY (66) during finger citron development were also analyzed. From extracted subnetworks of three modules constructed by weighted gene co-expression network analysis (WGCNA), thirteen TPS genes and fifteen transcription factors were suggested to be related to volatile terpenoid formation. These results provide a framework for future investigations into the identification and regulatory network of terpenoids in finger citron. Full article

(This article belongs to the Special Issue Plant Isoprenoids)

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13 pages, 1842 KiB

Open AccessArticle

Identification and Characterization of trans-Isopentenyl Diphosphate Synthases Involved in Herbivory-Induced Volatile Terpene Formation in Populus trichocarpa

by Nathalie D. Lackus, Nora P. Petersen, Raimund Nagel, Axel Schmidt, Sandra Irmisch, Jonathan Gershenzon and Tobias G. Köllner

Molecules 2019, 24(13), 2408; https://doi.org/10.3390/molecules24132408 - 29 Jun 2019

Cited by 11 | Viewed by 3238

Abstract

In response to insect herbivory, poplar releases a blend of volatiles that plays important roles in plant defense. Although the volatile bouquet is highly complex and comprises several classes of compounds, it is dominated by mono- and sesquiterpenes. The most common precursors for mono- and sesquiterpenes, geranyl diphosphate (GPP) and (E,E)-farnesyl diphosphate (FPP), respectively, are in general produced by homodimeric or heterodimeric trans-isopentenyl diphosphate synthases (trans-IDSs) that belong to the family of prenyltransferases. To understand the molecular basis of herbivory-induced terpene formation in poplar, we investigated the trans-IDS gene family in the western balsam poplar Populus trichocarpa. Sequence comparisons suggested that this species possesses a single FPP synthase gene (PtFPPS1) and four genes encoding two large subunits (PtGPPS1.LSU and PtGPPS2.LSU) and two small subunits (PtGPPS.SSU1 and PtGPPS.SSU2) of GPP synthases. Transcript accumulation of PtGPPS1.LSU and PtGPPS.SSU1 was significantly upregulated upon leaf herbivory, while the expression of PtFPPS1, PtGPPS2.LSU, and PtGPPS.SSU2 was not influenced by the herbivore treatment. Heterologous expression and biochemical characterization of recombinant PtFPPS1, PtGPPS1.LSU, and PtGPPS2.LSU confirmed their respective IDS activities. Recombinant PtGPPS.SSU1 and PtGPPS.SSU2, however, had no enzymatic activity on their own, but PtGPPS.SSU1 enhanced the GPP synthase activities of PtGPPS1.LSU and PtGPPS2.LSU in vitro. Altogether, our data suggest that PtGPPS1.LSU and PtGPPS2.LSU in combination with PtGPPS.SSU1 may provide the substrate for herbivory-induced monoterpene formation in P. trichocarpa. The sole FPP synthase PtFPPS1 likely produces FPP for both primary and specialized metabolism in this plant species. Full article

(This article belongs to the Special Issue Plant Isoprenoids)

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14 pages, 2933 KiB

Open AccessArticle

16-Hydroxy-Lycopersene, a Polyisoprenoid Alcohol Isolated from Tournefortia hirsutissima, Inhibits Nitric Oxide Production in RAW 264.7 Cells and Induces Apoptosis in Hep3B Cells

by Israel Hurtado-Díaz, Jessica Nayelli Sánchez-Carranza, Antonio Romero-Estrada, Leticia González-Maya, Judith González-Christen, Maribel Herrera-Ruiz and Laura Alvarez

Molecules 2019, 24(13), 2366; https://doi.org/10.3390/molecules24132366 - 26 Jun 2019

Cited by 6 | Viewed by 3421

Abstract

Three polyisoprenoid alcohols were isolated from the leaves of Tournefortia hirsutissima by a bioassay-guided phytochemical investigation. The compounds were identified as 16-hydroxy-lycopersene (Compound 1), (Z₈,E₃,ω)-dodecaprenol (Compound 2) and (Z₉,E₃,ω)-tridecaprenol (Compound 3). Compound 1, an unusual polyisoprenoid, was characterized by 1D and 2D NMR. We also determined the absolute configuration at C-16 by the modified Mosher’s method. The in vitro antiproliferative and anti-inflammatory activities of the isolated compounds were evaluated. Among isolates, Compound 1 moderately inhibited the nitric oxide production in lipopolysaccharide (LPS)-stimulated RAW 264.7 cells. On the other hand, Compound 1 displayed selective antiproliferative activity against HeLa, PC3, HepG2 and Hep3B cancer cells and was less potent against IHH non-cancerous cells. Compound 1 in Hep3B cells showed significant inhibition of cell cycle progression increasing the sub-G₁ phase, suggesting cell death. Acridine orange/ethidium bromide staining and Annexin V-FITC/PI staining demonstrated that cell death induced by Compound 1 in cells Hep3B was by apoptosis. Further study showed that apoptosis induced by Compound 1 in Hep3b cells is associated with the increase of the ratio of Bax/Bcl-2, and caspase 3/7 activation. These results suggest that Compound 1 induce apoptotic cell death by the mitochondrial pathway. To our knowledge, this is the first report about the presence of polyprenol Compounds 1–3 in T. hirsutissima, and the apoptotic and anti-inflammatory action of Compound 1. Full article

(This article belongs to the Special Issue Plant Isoprenoids)

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Review

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25 pages, 3258 KiB

Open AccessReview

Functional Gene Network of Prenyltransferases in Arabidopsis thaliana

by Diana Kopcsayová and Eva Vranová

Molecules 2019, 24(24), 4556; https://doi.org/10.3390/molecules24244556 - 12 Dec 2019

Cited by 12 | Viewed by 3592

Abstract

Prenyltransferases (PTs) are enzymes that catalyze prenyl chain elongation. Some are highly similar to each other at the amino acid level. Therefore, it is difficult to assign their function based solely on their sequence homology to functional orthologs. Other experiments, such as in vitro enzymatic assay, mutant analysis, and mutant complementation are necessary to assign their precise function. Moreover, subcellular localization can also influence the functionality of the enzymes within the pathway network, because different isoprenoid end products are synthesized in the cytosol, mitochondria, or plastids from prenyl diphosphate (prenyl-PP) substrates. In addition to in vivo functional experiments, in silico approaches, such as co-expression analysis, can provide information about the topology of PTs within the isoprenoid pathway network. There has been huge progress in the last few years in the characterization of individual Arabidopsis PTs, resulting in better understanding of their function and their topology within the isoprenoid pathway. Here, we summarize these findings and present the updated topological model of PTs in the Arabidopsis thaliana isoprenoid pathway. Full article

(This article belongs to the Special Issue Plant Isoprenoids)

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23 pages, 3226 KiB

Open AccessReview

Medically Useful Plant Terpenoids: Biosynthesis, Occurrence, and Mechanism of Action

by Matthew E. Bergman, Benjamin Davis and Michael A. Phillips

Molecules 2019, 24(21), 3961; https://doi.org/10.3390/molecules24213961 - 01 Nov 2019

Cited by 183 | Viewed by 17628

Abstract

Specialized plant terpenoids have found fortuitous uses in medicine due to their evolutionary and biochemical selection for biological activity in animals. However, these highly functionalized natural products are produced through complex biosynthetic pathways for which we have a complete understanding in only a few cases. Here we review some of the most effective and promising plant terpenoids that are currently used in medicine and medical research and provide updates on their biosynthesis, natural occurrence, and mechanism of action in the body. This includes pharmacologically useful plastidic terpenoids such as p-menthane monoterpenoids, cannabinoids, paclitaxel (taxol^®), and ingenol mebutate which are derived from the 2-C-methyl-d-erythritol-4-phosphate (MEP) pathway, as well as cytosolic terpenoids such as thapsigargin and artemisinin produced through the mevalonate (MVA) pathway. We further provide a review of the MEP and MVA precursor pathways which supply the carbon skeletons for the downstream transformations yielding these medically significant natural products. Full article

(This article belongs to the Special Issue Plant Isoprenoids)

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14 pages, 847 KiB

Open AccessReview

Protein Prenylation in Plant Stress Responses

by Michal Hála and Viktor Žárský

Molecules 2019, 24(21), 3906; https://doi.org/10.3390/molecules24213906 - 30 Oct 2019

Cited by 8 | Viewed by 5203

Abstract

Protein prenylation is one of the most important posttranslational modifications of proteins. Prenylated proteins play important roles in different developmental processes as well as stress responses in plants as the addition of hydrophobic prenyl chains (mostly farnesyl or geranyl) allow otherwise hydrophilic proteins to operate as peripheral lipid membrane proteins. This review focuses on selected aspects connecting protein prenylation with plant responses to both abiotic and biotic stresses. It summarizes how changes in protein prenylation impact plant growth, deals with several families of proteins involved in stress response and highlights prominent regulatory importance of prenylated small GTPases and chaperons. Potential possibilities of these proteins to be applicable for biotechnologies are discussed. Full article

(This article belongs to the Special Issue Plant Isoprenoids)

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