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Results for “Terpenoid”

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At least 19 recordsLinked to original sources
PubMed2025

Genomic mechanism of aroma terpenoids biosynthesis in plants.

BACKGROUND: Aroma terpenoids are crucial plant secondary metabolites with physiological and commercial importance. Interestingly, both closely and distantly related species can synthesize identical aroma terpenoids. With the development of genome sequencing technology, it has become possible to elucidate the genomic mechanism underlying this phenomenon. AIM: This review highlights whole-genome data as a robust strategy for investigating the genomic mechanism of aroma terpenoids biosynthesis in plants, and provides new perspectives on the origin, evolution, and engineering of terpene synthases (TPSs). This aims to significantly benefit plant breeding and enhance suitability for industrial production. KEY SCIENTIFIC CONCEPTS OF REVIEW: Genomic mechanism of aroma terpenoids biosynthesis in plant genomes is the genetic and evolutionary dynamics. We elaborate the genomic mechanism governing the biosynthesis of plant-derived aroma terpenoids in three dimensions: (1) Genome-wide identification and phylogenetic analyses of TPSs. The same aroma terpenoids were produced by numerous plant species with chromosome-level genomes. Based on 34 plant genomes, we identified 1643 TPSs and classified them into seven subfamilies. (2) Functional and structural basis of TPSs. We found that TPSs with identical functions in distant species exhibit low sequence similarity but conserved active cavity architectures. Conversely, functionally distinct TPSs in closely related species cluster phylogenetically but differ in active cavity structures. (3) Patterns of TPS gene origination. Comparative genomic analyses within and between species revealed three patterns enabling TPSs to acquire the same functions: tandem duplications, dispersed duplications, and genes without duplication.

Terpenes↗
PubMed1975

Gas-liquid chromatography of carotenoids and other terpenoids.

The retention behaviour of over seventy terpenoids on three silicone polymer liquid phases under both isothermal and temperature-programmed conditions is reported. Terpenoids with conjugated unsaturation (e.g., carotenoids) were hydrogenated prior to analysis in order to prevent thermal decomposition. Analyses of the acetates and TMS ethers of both the natural hydroxycarotenoids and their perhydroderivatives are also reported. In addition, a system is described for the routine analysis of terpenols, including those whose pyrophosphates are intermediates in sterol and carotenoid biosynthesis.

Acetylation↗
PubMed2026

Divergent Lineage of Terpene Synthases Establishes Terpenoid Biosynthesis in Brown Macroalgae.

Brown algae of the order Dictyotales uniquely stand out among stramenopiles (heterokonts) as prolific producers of bioactive terpenoid molecules associated with chemical defense and antifouling. Although more than 200 sesquiterpenoids and diterpenoids have been reported, largely from the genera of Dictyota and Dictyopteris, their biosynthetic origin has remained unknown for decades. Leveraging de novo genome and transcriptome sequencing in the nonmodel alga Dictyota coriacea, we identified a brown algal-specific lineage of type I terpene synthases (TSs) that harbors novel catalytic motifs distinct from those characterized in plants, microbes, red algae, and metazoans. Across three brown algal species, we characterized 15 terpene synthases, including DcTS-2, which produces the diterpene alcohol dilophol, a proposed biosynthetic intermediate to the antifouling metabolite pachydictyol A. X-ray crystal structures of the monoterpene synthase DcTS-3 further revealed that the brown algal enzymes retain the canonical terpene synthase fold, and together with mutagenesis studies, suggest the catalytic role of the novel motifs defining this newly established evolutionary lineage. Brown algal terpene synthases separate into two subgroups, with mono- and diTSs containing putative chloroplast-targeting sequences while sesquiTSs lack them, suggesting convergent compartmentalization of terpene biosynthesis with land plants. Together, these findings establish the molecular basis of terpenoid biosynthesis in brown algae and highlight the challenges of adapting established biosynthetic logic to nonmodel marine algae.

Alkyl and Aryl Transferases↗
PubMed2025

A multifunctional sesquiterpene synthase integrates with cytochrome P450s to reinforce the terpenoid defense network in maize.

Terpenoids, the largest and most structurally diverse class of plant natural products, play essential roles in maize defense and ecological interactions. In this study, we identified and functionally characterized a sesquiterpenoid-based defense pathway in maize centered on α-santalenoic acid, a pathogen-inducible sesquiterpenoid antibiotic. Using a combination of metabolite-based genome-wide association studies (mGWAS), linkage mapping, and heterologous expression assays, we identified ZmTPS9 as a multiproduct terpene synthase that primarily produces α-santalene and β-bisabolene. Sequence analysis and site-directed mutagenesis revealed that threonine at position 413 is critical for enzyme activity, with its deletion resulting in a complete loss of enzyme activity. The sesquiterpene hydrocarbons produced by ZmTPS9 are further oxidized by three cytochrome P450 monooxygenases, ZmCYP71Z16, ZmCYP71Z18, and ZmCYP71Z19, to yield antimicrobial metabolites including α-santalenoic acid, zealexin D1 (ZD1), and zealexin D2 (ZD2). Together, these findings demonstrate a convergent biosynthetic strategy in maize, where multiproduct terpene synthases and promiscuous P450s collaboratively generate a flexible and robust terpenoid defense network.

Zea mays↗
PubMed2026

Whole-Genome Sequence Dataset of Rhodococcus qingshengii IEGM 267-Terpenoid Biotransformer Toward Genetic Functional Annotation.

Background/Objectives: Microbial biotransformation of monoterpenoids is a promising approach for obtaining bioactive compounds. Rhodococcus species are attractive biocatalysts due to their metabolic versatility and ability to transform hydrophobic substrates. In this study, we investigated the catalytic potential of Rhodococcus qingshengii IEGM 267 toward carveol isomers and explored genomic features that may underlie this activity. Methods: The strain was cultivated in mineral medium supplemented with (-)-trans-carveol. Biotransformation products were analyzed by TLC and GC-MS. The draft genome was sequenced, assembled, taxonomically assigned, and annotated using standard bioinformatics tools. Results: Rhodococcus qingshengii IEGM 267 efficiently converted (-)-trans-carveol to carvone. Genome analysis confirmed the taxonomic assignment of the strain and revealed a large repertoire of oxidoreductases, including monooxygenases, hydroxylases, and dehydrogenases. Seven genes encoding cytochrome P450-dependent oxygenases were identified as candidate enzymes potentially involved in carveol oxidation. Conclusions: R. qingshengii IEGM 267 is an efficient and stereoselective biocatalyst for (-)-trans-carveol oxidation. The results of bioinformatics analysis suggest an alternative enzymatic basis for this transformation and provide a foundation for future functional characterization.

Rhodococcus↗
PubMed1979

Terpenoid biotransformation in mammals. II: Biotransformation of dl-camphene in rabbits.

The biotransformation of dl-camphene in rabbits was investigated. Four neutral metabolites, 6-exo-hydroxycamphene, 10-hydroxycamphene, and diastereoisomers of camphene-2,10-glycol, were identified and two alcohols, 7-hydroxycamphene and 3-hydroxytricyclene, were estimated by IR, UV, NMR, and mass spectra and chemical degradations. The formation of these compounds can be explained through a homoallylic oxidation or an epoxide formation.

Animals↗
PubMed2025

Insights into dill (Anethum graveolens) flavor formation via integrative analysis of chromosomal-scale genome, metabolome and transcriptome.

INTRODUCTION: Dill (Anethum graveolens) is a significant medicinal herb belonging to the Apiaceae family. Owing to its high levels of volatile organic compounds (VOCs), dill is commonly utilized for essential oil extraction and medicine purpose. However, the biosynthesis of the crucial VOC in dill remains obscure. OBJECTIVES: Identify the key VOCs related to the flavor formation in dill and dissect the regulatory mechanism of their synthesis. METHODS: The dill chromosomal-level genome was constructed by PacBio HiFi, Hi-C, and BGISEQ second generation sequencing and assembly. The VOCs in dill leaves were identified through GC-MS. The potential mechanism involved in regulating the VOC accumulation in dill flavor formation was analyzed by multi-omics analysis. RESULTS: A 1.17 Gb chromosome-scale genome of dill with a contig N50 of 10.78 Mb was constructed. A total of 46,538 genes were annotated across 11 assembled chromosomes. Comparative genomics analysis suggested that transposable element insertions, especially LTR-Gypsy, have contributed to the evolution and expansion of the dill genome. The flavor formation of dill was mainly attributed to terpenoids, especially α-phellandrene, β-ocimene, and o-cymene. The contribution of expansion and replication of terpenoid synthesis pathway genes, especially terpene synthase (TPS), to the abundant terpenoid production of dill was identified. Differential gene expression patterns observed at various developmental stages and tissues provided key candidate genes for the regulation of terpenoid synthesis, as well as transcription factors. The different accumulation of esters and aromatics also affected the flavor formation of dill. The key genes implicated in the synthesis of anethole, namely AIS and AMT were further identified. CONCLUSION: This study constructed the chromosome level genome and identified the main VOCs and related key genes in flavor formation of dill, shedding lights on our understanding of terpenoid biosynthesis but also offered guidance for future genetic research on molecular breeding in Anethum graveolens.

Transcriptome↗
PubMed2026

Ubiquitin ligase HcPUB30 targets HcWRKY1 to regulate monoterpenoids synthesis in Hedychium coronarium.

Hedychium coronarium, a perennial herb belonging to the genus Hedychium Koenig within the family Zingiberaceae, is renowned for its pleasant fragrance. The volatile compounds of flowers are primarily terpenoids, which are catalyzed by terpenoid synthase (TPS). Earlier studies have shown that HcWRKY1 transcription factor can bind to the promoter of HcTPS1, regulating the metabolism of terpenoids. To further investigate the upstream molecular mechanisms that regulate the release of volatile compounds in Hedychium, we focused on a crucial U-box type of E3 ubiquitin ligase involved in regulating transcription factors. This study utilized genomic data to identify HcPUB gene family. In combination with transcriptome data, seven candidate HcPUB genes were identified and cloned with subsequent functional analysis. Yeast two-hybrid assay demonstrated that HcPUB30 was the sole interactor of HcWRKY1 among the seven HcPUB candidates. In vivo and in vitro ubiquitination assays demonstrated that HcPUB30 ubiquitinates and promotes the degradation of HcWRKY1 via the 26S proteasome pathway. Multi-alignment analysis revealed that HcPUB30 possesses a conserved U-box domain and ARM motifs, which are implicated in plant growth and development. Subcellular localization indicated that HcPUB30 is localized in both the nucleus and cytoplasm. Quantitative real-time PCR analysis revealed that HcPUB30 exhibited the highest expression in petal tissues, and its expression peaked during floral senescence stage. Virus-induced gene silencing of HcPUB30 in Hedychium petals resulted in a significant decrease in monoterpenoid content, accompanied by a significant reduction in the relative expression levels of HcWRKY1 and HcTPS1. These findings indicate that HcPUB30 participates in the regulation of monoterpenoid biosynthesis by mediating HcWRKY1 in Hedychium petals.

Plant Proteins↗