scholarly journals A molecular perspective on terpene variation in Australian Myrtaceae

2008 ◽  
Vol 56 (3) ◽  
pp. 197 ◽  
Author(s):  
Andras Keszei ◽  
Curt L. Brubaker ◽  
William. J. Foley
Keyword(s):  
Chemical Diversity ◽  
Oil Yield ◽  
Biosynthesis Pathway ◽  
Ecological Interactions ◽  
Molecular Variation ◽  
Ecological Context ◽  
Terpene Biosynthesis ◽  
Terpene Synthases ◽  
Genetic Studies ◽  
Molecular Information

The terpenoid-dominated essential oils in Australian Myrtaceae mediate many ecological interactions and are important industrially. Of all the significant essential oil-producing families, Myrtaceae is the only one for which there is no molecular information on terpene biosynthesis. Here we summarise available knowledge on terpene biosynthesis and its relevance to the Myrtaceae to provide a foundation for ecological and genetic studies of chemical diversity. There are several steps in the terpene biosynthesis pathway that have potential for influencing the oil yield, profile and composition of leaf oils in Myrtaceae. The biochemical steps that influence oil yield in Myrtaceae probably occur in the steps of the pathway leading up to the synthesis of the terpene backbone. Qualitative differences in oil profiles are more likely to be due to variation in terpene synthases and terpene-modifying enzymes. Most of the information on molecular variation in terpene biosynthesis is based on the analysis of artificially derived mutants but Australian Myrtaceae can provide examples of the same mechanisms in an ecological context.

scholarly journals Terpene Biosynthesis in Red Algae Is Catalyzed by Microbial Type But Not Typical Plant Terpene Synthases

2018 ◽  
Vol 179 (2) ◽  
pp. 382-390 ◽  
Author(s):  
Guo Wei ◽  
Qidong Jia ◽  
Xinlu Chen ◽  
Tobias G. Köllner ◽  
Debashish Bhattacharya ◽  
...  
Keyword(s):  
Red Algae ◽  
Terpene Biosynthesis ◽  
Terpene Synthases

scholarly journals Advanced Chemophenetic Analysis of Essential Oil from Leaves of Piper gaudichaudianum Kunth (Piperaceae) Using a New Reduction-Oxidation Index to Explore Seasonal and Circadian Rhythms

Plants ◽  
2021 ◽  
Vol 10 (10) ◽  
pp. 2116
Author(s):  
Ygor Jessé Ramos ◽  
Claudete da Costa-Oliveira ◽  
Irene Candido-Fonseca ◽  
George Azevedo de Queiroz ◽  
Elsie Franklin Guimarães ◽  
...  
Keyword(s):  
Essential Oils ◽  
Weighted Average ◽  
Chemical Diversity ◽  
Terpene Biosynthesis ◽  
Phenological Stages ◽  
Compound C ◽  
A Value ◽  
Chemical Profiles ◽  
Aromatic Species ◽  
Piper Gaudichaudianum

The aromatic species Piper gaudichaudianum Kunth (Piperaceae) is widely used in Brazil for medicinal and ritualistic applications. In the current study, chemophenetic patterns were realized across season and circadian rhythm based on the chemical profile of essential oils (EOs) from leaves. Hydrodistilled essential oils were analyzed by GC-MS and GC-FID, and a new calculation of metabolite oxidation level, averaged for each individual molecule component of the EO, was used to explore the patterns of metabolism/biosynthesis. This new index used an intermediate calculation, the ‘weighted average redox standard’ (SRO), to enable a value for mixtures of metabolites to be generated, the ‘general mixture redox index’ (GMOR). The indices were subjected to a proof-of-concept approach by making comparison to outcomes from multivariate analyses, i.e., PCA and HCA. Chemical analysis demonstrated that the essential oils were dominated by sesquiterpenes, constructed of 15 classes of compound (C-skeletons), and 4 C-skeletons were recognized in the monoterpene group, giving a total of 19. The variation of chemical profiles was distinct at different phenological stages, but stronger chemical variation was evident between day and night as compared to season. Furthermore, due to comprehensive sampling across different regions, nine chemotypes were recognized, including those previously reported. The SRO and GMRO indices demonstrate that phenological variation of chemistry is mainly an outcome of redox fluctuations in terpene biosynthesis, changing from day to night. These indices also corroborate that chemical diversity is increased with oxidative metabolism. Lastly, the current study demonstrates pronounced phenotypic plasticity in P. gaudichaudianum, which makes it a suitable candidate to help further our understanding of chemophenetics and chemical ecology.

scholarly journals A Review of the Ephedra genus: Distribution, Ecology, Ethnobotany, Phytochemistry and Pharmacological Properties

Molecules ◽  
2020 ◽  
Vol 25 (14) ◽  
pp. 3283
Author(s):  
Daphne E. González-Juárez ◽  
Abraham Escobedo-Moratilla ◽  
Joel Flores ◽  
Sergio Hidalgo-Figueroa ◽  
Natalia Martínez-Tagüeña ◽  
...  
Keyword(s):  
Chemical Constituents ◽  
Nasal Congestion ◽  
Building Blocks ◽  
Relevant Information ◽  
Chemical Diversity ◽  
Future Research ◽  
Pharmacological Properties ◽  
Ecological Interactions ◽  
Phytochemical Study ◽  
Promising Area

Ephedra is one of the largest genera of the Ephedraceae family, which is distributed in arid and semiarid regions of the world. In the traditional medicine from several countries some species from the genus are commonly used to treat asthma, cold, flu, chills, fever, headache, nasal congestion, and cough. The chemical constituents of Ephedra species have been of research interest for decades due to their contents of ephedrine-type alkaloids and its pharmacological properties. Other chemical constituents such as phenolic and amino acid derivatives also have resulted attractive and have provided evidence-based supporting of the ethnomedical uses of the Ephedra species. In recent years, research has been expanded to explore the endophytic fungal diversity associated to Ephedra species, as well as, the chemical constituents derived from these fungi and their pharmacological bioprospecting. Two additional aspects that illustrate the chemical diversity of Ephedra genus are the chemotaxonomy approaches and the use of ephedrine-type alkaloids as building blocks in organic synthesis. American Ephedra species, especially those that exist in Mexico, are considered to lack ephedrine type alkaloids. In this sense, the phytochemical study of Mexican Ephedra species is a promising area of research to corroborate their ephedrine-type alkaloids content and, in turn, discover new chemical compounds with potential biological activity. Therefore, the present review represents a key compilation of all the relevant information for the Ephedra genus, in particular the American species, the species distribution, their ecological interactions, its ethnobotany, its phytochemistry and their pharmacological activities and toxicities, in order to promote clear directions for future research.

scholarly journals Linking genomics and metabolomics to chart specialized metabolic diversity

2020 ◽  
Vol 49 (11) ◽  
pp. 3297-3314 ◽  
Author(s):  
Justin J. J. van der Hooft ◽  
Hosein Mohimani ◽  
Anelize Bauermeister ◽  
Pieter C. Dorrestein ◽  
Katherine R. Duncan ◽  
...  
Keyword(s):  
Chemical Diversity ◽  
Ecological Interactions ◽  
Metabolic Diversity ◽  
Metabolomics Data ◽  
Specialized Metabolites

Microbial and plant specialized metabolites play key roles in mediating ecological interactions between organisms. Analysis and integration of genomics and metabolomics data facilitates charting their immense chemical diversity.

scholarly journals Differential gene expression associated with a floral scent polymorphism in the evening primrose Oenothera harringtonii (Onagraceae)

2021 ◽  
Author(s):  
Lindsey L. Bechen ◽  
Matthew G. Johnson ◽  
Geoffrey T. Broadhead ◽  
Rachel A. Levin ◽  
Rick P. Overson ◽  
...  
Keyword(s):  
Gene Expression ◽  
Differential Gene Expression ◽  
Floral Scent ◽  
Terpene Synthase ◽  
Rna Seq ◽  
Loss Of Function ◽  
Terpene Biosynthesis ◽  
Terpene Synthases ◽  
Evening Primrose ◽  
Differential Gene

AbstractBackgroundPlant volatiles play an important role in both plant-pollinator and plant-herbivore interactions. Intraspecific polymorphisms in volatile production are ubiquitous, but studies that explore underlying differential gene expression are rare. Oenothera harringtonii populations are polymorphic in floral emission of the monoterpene (R)-(-)-linalool; some plants emit (R)-(-)-linalool (linalool+ plants) while others do not (linalool-plants). However, the genes associated with differential production of this floral volatile in Oenothera are unknown. We used RNA-Seq to broadly characterize differential gene expression involved in (R)-(-)-linalool biosynthesis. To identify genes that may be associated with the polymorphism for this trait, we used RNA-Seq to compare gene expression in six different Oenothera harringtonii tissues from each of three linalool+ and linalool-plants.ResultsThree clusters of differentially expressed genes were enriched for terpene synthase activity: two were characterized by tissue-specific upregulation and one by upregulation only in plants with flowers that produce (R)-(-)-linalool. A molecular phylogeny of all terpene synthases identified two putative (R)-(-)-linalool synthase transcripts in Oenothera harringtonii, a single allele of which is found exclusively in linalool+ plants.ConclusionsBy using a naturally occurring polymorphism and comparing different tissues, we were able to identify genes putatively involved in the biosynthesis of (R)-(-)-linalool. Expression of these genes in linalool-plants suggests a regulatory polymorphism, rather than a population-specific loss-of-function allele. Additional terpene biosynthesis-related genes that are up-regulated in plants that emit (R)-(-)-linalool may be associated with herbivore defense, suggesting a potential economy of scale between plant reproduction and defense.

scholarly journals Emission and biosynthesis of volatile terpenoids from the plasmodial slime mold Physarum polycephalum

2019 ◽  
Vol 15 ◽  
pp. 2872-2880
Author(s):  
Xinlu Chen ◽  
Tobias G Köllner ◽  
Wangdan Xiong ◽  
Guo Wei ◽  
Feng Chen
Keyword(s):  
Physarum Polycephalum ◽  
Slime Mold ◽  
Terpene Biosynthesis ◽  
Terpene Synthases ◽  
Slime Molds ◽  
Geranyl Diphosphate ◽  
Monoterpene Synthase ◽  
Cellular Slime ◽  
Volatile Terpenoids

Terpene synthases (TPSs) are pivotal enzymes for the production of diverse terpenes, including monoterpenes, sesquiterpenes, and diterpenes. In our recent studies, dictyostelid social amoebae, also known as cellular slime molds, were found to contain TPS genes for making volatile terpenes. For comparison, here we investigated Physarum polycephalum, a plasmodial slime mold also known as acellular amoeba. Plasmodia of P. polycephalum grown on agar plates were found to release a mixture of volatile terpenoids consisting of four major sesquiterpenes (α-muurolene, (E)-β-caryophyllene, two unidentified sesquiterpenoids) and the monoterpene linalool. There were no qualitative differences in terpenoid composition at two stages of young plasmodia. To understand terpene biosynthesis, we analyzed the transcriptome and genome sequences of P. polycephalum and identified four TPS genes designated PpolyTPS1–PpolyTPS4. They share 28–73% of sequence identities. Full-length cDNAs for the four TPS genes were cloned and expressed in Escherichia coli to produce recombinant proteins, which were tested for sesquiterpene synthase and monoterpene synthase activities. While neither PpolyTPS2 nor PpolyTPS3 was active, PpolyTPS1 and PpolyTPS4 were able to produce sesquiterpenes and monoterpenes from the respective substrates farnesyl diphosphate and geranyl diphosphate. By comparing the volatile profile of P. polycephalum plasmodia and the in vitro products of PpolyTPS1 and PpolyTPS4, it was concluded that most sesquiterpenoids emitted from P. polycephalum were attributed to PpolyTPS4. Phylogenetic analysis placed the four PpolyTPSs genes into two groups: PpolyTPS1 and PpolyTPS4 being one group that was clustered with the TPSs from the dictyostelid social amoeba and PpolyTPS2 and PpolyTPS3 being the other group that showed closer relatedness to bacterial TPSs. The biological role of the volatile terpenoids produced by the plasmodia of P. polycephalum is discussed.

scholarly journals Terpene synthase genes in eukaryotes beyond plants and fungi: Occurrence in social amoebae

2016 ◽  
Vol 113 (43) ◽  
pp. 12132-12137 ◽  
Author(s):  
Xinlu Chen ◽  
Tobias G. Köllner ◽  
Qidong Jia ◽  
Ayla Norris ◽  
Balaji Santhanam ◽  
...  
Keyword(s):  
Early Stage ◽  
Terpene Synthase ◽  
Functional Study ◽  
Terpene Biosynthesis ◽  
Terpene Synthases ◽  
Multicellular Development ◽  
Stage Of Development ◽  
The Social ◽  
Volatile Terpenes ◽  
Social Amoebae

Terpenes are structurally diverse natural products involved in many ecological interactions. The pivotal enzymes for terpene biosynthesis, terpene synthases (TPSs), had been described only in plants and fungi in the eukaryotic domain. In this report, we systematically analyzed the genome sequences of a broad range of nonplant/nonfungus eukaryotes and identified putative TPS genes in six species of amoebae, five of which are multicellular social amoebae from the order of Dictyosteliida. A phylogenetic analysis revealed that amoebal TPSs are evolutionarily more closely related to fungal TPSs than to bacterial TPSs. The social amoeba Dictyostelium discoideum was selected for functional study of the identified TPSs. D. discoideum grows as a unicellular organism when food is abundant and switches from vegetative growth to multicellular development upon starvation. We found that expression of most D. discoideum TPS genes was induced during development. Upon heterologous expression, all nine TPSs from D. discoideum showed sesquiterpene synthase activities. Some also exhibited monoterpene and/or diterpene synthase activities. Direct measurement of volatile terpenes in cultures of D. discoideum revealed essentially no emission at an early stage of development. In contrast, a bouquet of terpenes, dominated by sesquiterpenes including β-barbatene and (E,E)-α-farnesene, was detected at the middle and late stages of development, suggesting a development-specific function of volatile terpenes in D. discoideum. The patchy distribution of TPS genes in the eukaryotic domain and the evidence for TPS function in D. discoideum indicate that the TPS genes mediate lineage-specific adaptations.

Transcriptome sequencing reveals terpene biosynthesis pathway genes accounting for volatile terpene of tree peony

Planta ◽  
2021 ◽  
Vol 254 (4) ◽  
Author(s):  
Rongchen Li ◽  
Ziyao Li ◽  
Pingsheng Leng ◽  
Zenghui Hu ◽  
Jing Wu ◽  
...  
Keyword(s):  
Transcriptome Sequencing ◽  
Biosynthesis Pathway ◽  
Tree Peony ◽  
Terpene Biosynthesis ◽  
Volatile Terpene

scholarly journals Generation of a chromosome-scale genome assembly of the insect-repellent terpenoid-producing Lamiaceae species, Callicarpa americana

GigaScience ◽  
2020 ◽  
Vol 9 (9) ◽  
Author(s):  
John P Hamilton ◽  
Grant T Godden ◽  
Emily Lanier ◽  
Wajid Waheed Bhat ◽  
Taliesin J Kinser ◽  
...  
Keyword(s):  
Genome Assembly ◽  
Tectona Grandis ◽  
Chemical Diversity ◽  
Insect Repellent ◽  
Terpene Synthases ◽  
Insect Repellents ◽  
Road Map ◽  
Genes Encoding ◽  
Long Read ◽  
Duplication Events

Abstract Background Plants exhibit wide chemical diversity due to the production of specialized metabolites that function as pollinator attractants, defensive compounds, and signaling molecules. Lamiaceae (mints) are known for their chemodiversity and have been cultivated for use as culinary herbs, as well as sources of insect repellents, health-promoting compounds, and fragrance. Findings We report the chromosome-scale genome assembly of Callicarpa americana L. (American beautyberry), a species within the early-diverging Callicarpoideae clade of Lamiaceae, known for its metallic purple fruits and use as an insect repellent due to its production of terpenoids. Using long-read sequencing and Hi-C scaffolding, we generated a 506.1-Mb assembly spanning 17 pseudomolecules with N50 contig and N50 scaffold sizes of 7.5 and 29.0 Mb, respectively. In all, 32,164 genes were annotated, including 53 candidate terpene synthases and 47 putative clusters of specialized metabolite biosynthetic pathways. Our analyses revealed 3 putative whole-genome duplication events, which, together with local tandem duplications, contributed to gene family expansion of terpene synthases. Kolavenyl diphosphate is a gateway to many of the bioactive terpenoids in C. americana; experimental validation confirmed that CamTPS2 encodes kolavenyl diphosphate synthase. Syntenic analyses with Tectona grandis L. f. (teak), a member of the Tectonoideae clade of Lamiaceae known for exceptionally strong wood resistant to insects, revealed 963 collinear blocks and 21,297 C. americana syntelogs. Conclusions Access to the C. americana genome provides a road map for rapid discovery of genes encoding plant-derived agrichemicals and a key resource for understanding the evolution of chemical diversity in Lamiaceae.

scholarly journals First Draft Genome of a Brazilian Atlantic Rainforest Burseraceae reveals commercially-promising genes involved in terpenic oleoresins synthesis

2018 ◽  
Author(s):  
Luana Ferreira Afonso ◽  
Danielle Amaral ◽  
Marcela Uliano-Silva ◽  
André Luiz Quintanilha Torres ◽  
Daniel Reis Simas ◽  
...  
Keyword(s):  
De Novo ◽  
Pfam Domain ◽  
Draft Genome ◽  
Atlantic Rainforest ◽  
Volatile Fraction ◽  
Terpene Biosynthesis ◽  
Terpene Synthases ◽  
Limonene Synthase ◽  
Molecular Bases

BackgroundProtium species produce abundant aromatic oleoresins composed mainly of different types of terpenes, which are highly sought after by the flavor and fragrance industry.ResultsHere we present (i) the first draft genome of an endemic tree of the Brazil’s Atlantic Rainforest (Mata Atlântica), Protium kleinii Cuatrec., (ii) a first characterization of its genes involved in the terpene pathways, and (iii) the composition of the resin’s volatile fraction. The de novo draft genome was assembled using Illumina paired-end-only data, totalizing 407 Mb in size present in 229,912 scaffolds. The N50 is 2.60 Kb and the longest scaffold is 52.26 Kb. Despite its fragmentation, we were able to infer 53,538 gene models of which 5,434 were complete. The draft genome of P. kleinii presents 76.67 % (62.01 % complete and 14.66 % partial) of plant-core BUSCO genes. InterProScan was able to assign at least one Gene Ontology annotation and one Pfam domain for 13,629 and 26,469 sequences, respectively. We were able to identify 116 enzymes involved in terpene biosynthesis, such as monoterpenes α-terpineol, 1,8-cineole, geraniol, (+)-neomenthol and (+)-(R)-limonene. Through the phylogenetic analysis of the Terpene Synthases gene family, three candidates of limonene synthase were identified. Chemical analysis of the resin’s volatile fraction identified four monoterpenes: terpinolene, limonene, α-pinene and α-phellandrene.ConclusionThese results provide resources for further studies to identify the molecular bases of the main aroma compounds and new biotechnological approaches to their production.

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