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Terpenes and Terpenoids in Plants: From Biosynthesis and Structural Identification to Ecological Functions and Biotechnological Applications

A special issue of International Journal of Molecular Sciences (ISSN 1422-0067). This special issue belongs to the section "Molecular Plant Sciences".

Deadline for manuscript submissions: closed (31 March 2023) | Viewed by 10768

Special Issue Editors

Dr. Ali Siah

E-Mail Website
Guest Editor
UMR-t INRAE 1158 BioEcoAgro Junia Lille, F-59014 Lille, France
Interests: plant biology; plant physiology; molecular plant biology; transcriptomics; plant-microbe interactions; plant immunity; specialized metabolites; biological activities
Dr. David Gagneul

E-Mail Website
Guest Editor
UMR-t INRAE 1158 BioEcoAgro, University of Lille, Villeneuve d’Ascq, F-59655 Lille, France
Interests: plant physiology; molecular plant biology; phytochemistry; metabolomics; specialized metabolites; terpenes and terpenoids; biosynthesic pathways
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues, 

Terpenes, also known as terpenoids or isoprenoids, constitute a major class of metabolites, with a remarkable diversity in both structure and function. They are made of isoprene molecules (five carbon building blocks). The word terpenes is sometimes used to refer to simple hydrocarbons based on combinations of dimethylallyl pyrophosphate and its isomer, isopentenyl pyrophosphate, while the word terpenoids (or isoprenoids) refers to terpenes with oxygen moiety and additional structural rearrangements. They are naturally synthesized by a wide range of living organisms where they are known to play primary functions, but a huge set of chemically diverse terpenes synthesized by plants are known for their roles in the interaction of the plant with its environment. These particular types of terpenes are ranked among plant specialized metabolites.

This Special Issue will focus on the recent advances in plant terpenes and terpenoids and is dedicated to all disciplinary fields related to this class of plant specialized metabolites. Particular attention will be given to the recent discoveries regarding: (i) the identification, as well as the molecular and biochemical mechanisms underlaying the biosynthesic pathways of plant terpenes and terpenoids; (ii) the separation, isolation, and production of these compounds using green and innovative bioprocesses; and (iii) the unraveling of their roles in plant–environment interactions, including plant responses to biotic (pathogens, beneficial microbes, microbiome, insects, herbivores, neighboring plants, etc.) and abiotic (drought, temperature, soil chemistry, etc.) factors.

Dr. Ali Siah
Dr. David Gagneul
Guest Editors

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Keywords

  • phytochemistry
  • metabolomics
  • specialized metabolites
  • terpenes
  • terpenoids
  • biosynthesic pathways

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Published Papers (5 papers)

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16 pages, 4495 KiB  
Article
De Novo Transcriptome Sequencing of Codonopsis lanceolata for Identification of Triterpene Synthase and Triterpene Acetyltransferase
by Han-Bin Choi, Sangrea Shim, Myeong-Hyeon Wang and Yong-Eui Choi
Int. J. Mol. Sci. 2023, 24(6), 5769; https://doi.org/10.3390/ijms24065769 - 17 Mar 2023
Cited by 2 | Viewed by 1690
Abstract
Codonopsis lanceolata (Campanulaceae) is a perennial plant commonly known as the bonnet bellflower. This species is widely used in traditional medicine and is considered to have multiple medicinal properties. In this study, we found that shoots and roots of C. lanceolata contained various [...] Read more.
Codonopsis lanceolata (Campanulaceae) is a perennial plant commonly known as the bonnet bellflower. This species is widely used in traditional medicine and is considered to have multiple medicinal properties. In this study, we found that shoots and roots of C. lanceolata contained various types of free triterpenes (taraxerol, β-amyrin, α-amyrin, and friedelin) and triterpene acetates (taraxerol acetate, β-amyrin acetate, and α-amyrin acetate). The content of triterpenes and triterpene acetates by GC analysis was higher in the shoot than in the roots. To investigate the transcriptional activity of genes involved in triterpenes and triterpene acetate biosynthesis, we performed de novo transcriptome analysis of shoots and roots of C. lanceolata by sequencing using the Illumina platform. A total of 39,523 representative transcripts were obtained. After functional annotation of the transcripts, the differential expression of genes involved in triterpene biosynthetic pathways was investigated. Generally, the transcriptional activity of unigenes in the upstream region (MVA and MEP pathway) of triterpene biosynthetic pathways was higher in shoots than in roots. Various triterpene synthases (2,3-oxidosqualene cyclase, OSC) participate to produce triterpene skeletons by the cyclization of 2,3-oxidosqualene. A total of fifteen contigs were obtained in annotated OSCs in the representative transcripts. Functional characterization of four OSC sequences by heterologous expression in yeast revealed that ClOSC1 was determined as taraxerol synthase, and ClOSC2 was a mixed-amyrin synthase producing α-amyrin and β-amyrin. Five putative contigs of triterpene acetyltransferases showed high homology to the lettuce triterpene acetyltransferases. Conclusively, this study provides the basis of molecular information, particularly for the biosynthesis of triterpenes and triterpene acetates in C. lanceolata. Full article
(This article belongs to the Special Issue Terpenes and Terpenoids in Plants: From Biosynthesis and Structural Identification to Ecological Functions and Biotechnological Applications)
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15 pages, 2330 KiB  
Article
Functional Prediction of trans-Prenyltransferases Reveals the Distribution of GFPPSs in Species beyond the Brassicaceae Clade
by Jing Zhang, Yihua Ma, Qingwen Chen, Mingxia Yang, Deyu Feng, Fei Zhou, Guodong Wang and Chengyuan Wang
Int. J. Mol. Sci. 2022, 23(16), 9471; https://doi.org/10.3390/ijms23169471 - 22 Aug 2022
Cited by 1 | Viewed by 1880
Abstract
Terpenoids are the most diverse class of plant primary and specialized metabolites, and trans-prenyltransferases (trans-PTs) are the first branch point to synthesize precursors of various chain lengths for further metabolism. Whereas the catalytic mechanism of the enzyme is known, there [...] Read more.
Terpenoids are the most diverse class of plant primary and specialized metabolites, and trans-prenyltransferases (trans-PTs) are the first branch point to synthesize precursors of various chain lengths for further metabolism. Whereas the catalytic mechanism of the enzyme is known, there is no reliable method for precisely predicting the functions of trans-PTs. With the exponentially increasing number of available trans-PTs genes in public databases, an in silico functional prediction method for this gene family is urgently needed. Here, we present PTS-Pre, a web tool developed on the basis of the “three floors” model, which shows an overall 86% prediction accuracy for 141 experimentally determined trans-PTs. The method was further validated by in vitro enzyme assays for randomly selected trans-PTs. In addition, using this method, we identified nine new GFPPSs from different plants which are beyond the previously reported Brassicaceae clade, suggesting these genes may have occurred via convergent evolution and are more likely lineage-specific. The high accuracy of our blind prediction validated by enzymatic assays suggests that PTS-Pre provides a convenient and reliable method for genome-wide functional prediction of trans-PTs enzymes and will surely benefit the elucidation and metabolic engineering of terpenoid biosynthetic pathways. Full article
(This article belongs to the Special Issue Terpenes and Terpenoids in Plants: From Biosynthesis and Structural Identification to Ecological Functions and Biotechnological Applications)
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19 pages, 1405 KiB  
Review
Biosynthesis and the Transcriptional Regulation of Terpenoids in Tea Plants (Camellia sinensis)
by Junchi Wei, Yun Yang, Ye Peng, Shaoying Wang, Jing Zhang, Xiaobo Liu, Jianjun Liu, Beibei Wen and Meifeng Li
Int. J. Mol. Sci. 2023, 24(8), 6937; https://doi.org/10.3390/ijms24086937 - 8 Apr 2023
Cited by 19 | Viewed by 4004
Abstract
Terpenes, especially volatile terpenes, are important components of tea aroma due to their unique scents. They are also widely used in the cosmetic and medical industries. In addition, terpene emission can be induced by herbivory, wounding, light, low temperature, and other stress conditions, [...] Read more.
Terpenes, especially volatile terpenes, are important components of tea aroma due to their unique scents. They are also widely used in the cosmetic and medical industries. In addition, terpene emission can be induced by herbivory, wounding, light, low temperature, and other stress conditions, leading to plant defense responses and plant–plant interactions. The transcriptional levels of important core genes (including HMGR, DXS, and TPS) involved in terpenoid biosynthesis are up- or downregulated by the MYB, MYC, NAC, ERF, WRKY, and bHLH transcription factors. These regulators can bind to corresponding cis-elements in the promoter regions of the corresponding genes, and some of them interact with other transcription factors to form a complex. Recently, several key terpene synthesis genes and important transcription factors involved in terpene biosynthesis have been isolated and functionally identified from tea plants. In this work, we focus on the research progress on the transcriptional regulation of terpenes in tea plants (Camellia sinensis) and thoroughly detail the biosynthesis of terpene compounds, the terpene biosynthesis-related genes, the transcription factors involved in terpene biosynthesis, and their importance. Furthermore, we review the potential strategies used in studying the specific transcriptional regulation functions of candidate transcription factors that have been discriminated to date. Full article
(This article belongs to the Special Issue Terpenes and Terpenoids in Plants: From Biosynthesis and Structural Identification to Ecological Functions and Biotechnological Applications)
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19 pages, 3385 KiB  
Article
A Discovery-Based Metabolomic Approach Using UPLC-Q-TOF-MS/MS Reveals Potential Antimalarial Compounds Present in Artemisia annua L.
by Henan Shi, Zhuqing Wang, Fujie Xu, Jialin Li, Jing Li and Manyuan Wang
Int. J. Mol. Sci. 2022, 23(23), 14903; https://doi.org/10.3390/ijms232314903 - 28 Nov 2022
Cited by 6 | Viewed by 1477
Abstract
In 1972, Nobel laureate Youyou Tu’s research team conducted clinical trials on the dried material of Artemisia annua L. from Beijing extracted by ether and then treated with alkali (called “ether neutral dry”), which showed that artemisinin was not the only antimalarial component [...] Read more.
In 1972, Nobel laureate Youyou Tu’s research team conducted clinical trials on the dried material of Artemisia annua L. from Beijing extracted by ether and then treated with alkali (called “ether neutral dry”), which showed that artemisinin was not the only antimalarial component contained. The biosynthesis of sesquiterpenoids in A. annua has increased exponentially after unremitting cultivation efforts, and the plant resources are now quite different from those in the 1970s. In consideration of emerging artemisinin resistance, it is of great theoretical and practical value to further study the antimalarial activity of A. annua and explore its causes. The purpose of this study is to clarify scientific questions, such as “What ingredients are synergistic with artemisinin in A. annua?”, and “Are there non-artemisinin antimalarial ingredients in A. annua?”. In this paper, Beijing wild A. annua was used as a control and two representative cultivation species of A. annua were selected to evaluate the antimalarial activity of the herbal medicine. The antimalarial activity of different extracts on mice was studied using the Peters’ four-day suppressive test. UPLC-Q-TOF-MS was used to obtain mass spectrum data for all samples, and a UNIFI platform was used for identification. A multivariate statistical method was used to screen the different compounds with positive correlations. The antimalarial activity of different components from the ether extract and alkali treatments was determined and antimalarial components other than artemisinin were obtained. A total of 24 flavonoids, 68 sesquiterpenoids and 21 other compounds were identified. Compounds associated with differential antimalarial activity were identified. The material basis for the antimalarial activity of A. annua was clarified. The antimalarial components of A. annua include two categories: first, artemisinin and non-artemisinin antimalarial active components, of which the non-artemisinin antimalarial active components may include 5α-hydroperoxy-eudesma-4(15),11-diene; second, several antimalarial synergistic ingredients in A. annua, including arteanniun B, arteanniun B analogues and polymethoxy flavonoids. Full article
(This article belongs to the Special Issue Terpenes and Terpenoids in Plants: From Biosynthesis and Structural Identification to Ecological Functions and Biotechnological Applications)
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11 pages, 1943 KiB  
Article
Enhancing Structural Diversity of Lathyrane Derivatives through Biotransformation by the Marine-Derived Actinomycete Streptomyces puniceus BC-5GB.11
by Felipe Escobar-Montaño, Victoria E. González-Rodríguez, Antonio J. Macías-Sánchez, José M. Botubol-Ares, Rosa Durán-Patrón and Rosario Hernández-Galán
Int. J. Mol. Sci. 2024, 25(4), 2289; https://doi.org/10.3390/ijms25042289 - 14 Feb 2024
Cited by 2 | Viewed by 895
Abstract
Lathyrane-type diterpenes have a wide range of biological activities. Among them, euphoboetirane A (1) exerts neurogenesis-promoting activity. In order to increase the structural diversity of this type of lathyrane and explore its potential use in neurodegenerative disorders, the biotransformation of 1 [...] Read more.
Lathyrane-type diterpenes have a wide range of biological activities. Among them, euphoboetirane A (1) exerts neurogenesis-promoting activity. In order to increase the structural diversity of this type of lathyrane and explore its potential use in neurodegenerative disorders, the biotransformation of 1 by Streptomyces puniceus BC-5GB.11 has been investigated. The strain BC-5GB.11, isolated from surface sediments collected from the intertidal zone of the inner Bay of Cadiz, was identified as Streptomyces puniceus, as determined by phylogenetic analysis using 16S rRNA gene sequence. Biotransformation of 1 by BC-5GB.11 afforded five products (3–7), all of which were reported here for the first time. The main biotransformation pathways involved regioselective oxidation at non-activated carbons (3–5) and isomerization of the ∆12,13 double bond (6). In addition, a cyclopropane-rearranged compound was found (7). The structures of all compounds were elucidated on the basis of extensive NMR and HRESIMS spectroscopic studies. Full article
(This article belongs to the Special Issue Terpenes and Terpenoids in Plants: From Biosynthesis and Structural Identification to Ecological Functions and Biotechnological Applications)
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