Analysis of sesquiterpenes and sesquiterpenoids

Lorigooini, Zahra; Jamshidi-kia, Fatemeh; Dodman, Sadegh

doi:10.1016/b978-0-12-816455-6.00008-1

Cited by 11 publications

(5 citation statements)

References 56 publications

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“…IPP and DMAPP go through a series of condensation reactions by prenyl diphosphate synthases to form prenyl diphosphates like geranyl diphosphate (GPP; C10), farnesyl diphosphate (FPP; C15), geranylgeranyl diphosphate (GGPP; C20) and other diphosphates. These prenyl diphosphate precursors form a basis for the biosynthesis of a diverse classes of terpenoids currently observed in plants ( Figure 4 ; Figure S2 ) ( Lorigooini et al., 2020 ). The formation of FPP from IPP by the enzyme short-chain Z-isoprenyl diphosphate synthase (K12503, 1 unigene) leads to triterpenoid synthesis via squalene.…”

Section: Resultsmentioning

confidence: 99%

De novo transcriptome analysis of Dysoxylum binectariferum to unravel the biosynthesis of pharmaceutically relevant specialized metabolites

Kumara,

Varun,

Sanjay

et al. 2023

Front. Plant Sci.

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The tropical tree, D. binectariferum, is a prominent source of chromone alkaloid rohitukine, which is used in the semi-syntheses of anticancer molecules such as flavopiridol and P-276-00. The biosynthetic pathway of rohitukine or its derivatives is currently unknown in plants. Here, we explored chromone alkaloid biosynthesis in D. binectariferum through targeted transcriptome sequencing. Illumina sequencing of leaves and roots of a year-old D. binectariferum seedling generated, 42.43 and 38.74 million paired-end short reads, respectively. Quality filtering and de novo assembly of the transcriptome generated 274,970 contigs and 126,788 unigenes with an N50 contig length of 1560 bp. The assembly generated 117,619 translated unigene protein sequences and 51,598 non-redundant sequences. Nearly 80% of these non-redundant sequences were annotated to publicly available protein and nucleotide databases, suggesting the completeness and effectiveness of the transcriptome assembly. Using the assembly, we identified a chalcone synthase (CHS) and three type III polyketide synthases (PKS-III; non-CHS type) that are likely to be involved in the biosynthesis of chromone ring/noreugenin moiety of rohitukine. We also identified key enzymes like lysine decarboxylase in the piperidine pathway that make the piperidine moiety of rohitukine. Besides these, the upstream enzymes in flavonoid biosynthesis like phenylalanine ammonia-lyase (PAL), trans-cinnamate 4-hydroxylase (C4H),4-coumarate-CoA ligase (4CL), and chalcone isomerase (CHI) have also been identified. Also, terpene synthases that are likely to be involved in the biosynthesis of various terpenoid scaffolds have been identified. Together, the D. binectariferum transcriptome resource forms a basis for further exploration of biosynthetic pathways of these valuable compounds through functional validation of the candidate genes and metabolic engineering in heterologous hosts. Additionally, the transcriptome dataset generated will serve as an important resource for research on functional genomics and enzyme discovery in D. binectariferum and comparative analysis with other Meliaceae family members.

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Section: Resultsmentioning

confidence: 99%

De novo transcriptome analysis of Dysoxylum binectariferum to unravel the biosynthesis of pharmaceutically relevant specialized metabolites

Kumara,

Varun,

Sanjay

et al. 2023

Front. Plant Sci.

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“…Several researchers have also described the pharmaceutical and pest protection abilities of monoterpenoids and sesquiterpenoids from medicinal plants [21,54]. Many sesquiterpene compounds have been documented to have a variety of bioactivities, including cytotoxic [55], antioxidant [56], anti-aging, anti-inflammation, anti-anaphylaxis, antimicrobial, and antifungal activities [52,53,57,58]. Liu et al (2022) [59] stated that four sesquiterpenes isolated from Ambrosia artemisiifolia had inhibitory effects on Chenopodium album, Digitaria sanguinalis, Setaria viridis, and Arabidopsis thaliana.…”

Section: Discussionmentioning

confidence: 99%

Allelopathic Activity of a Novel Compound and Two Known Sesquiterpene from Croton oblongifolius Roxb.

Moh,

Tojo,

Teruya

et al. 2024

Agronomy

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Plant extracts with allelopathic activity and their related compounds have been investigated for a long time as an eco-friendly approach to sustainable weed management. Croton oblongifolius (Roxb.) is a traditional medicinal plant valued for its diverse source of bioactive compounds that have been used to treat various diseases. C. oblongifolius leaf extract was previously described to involve a number of allelochemicals. Therefore, we conducted this research to explore more of the allelochemicals in the leaves of C. oblongifolius. The leaf extracts showed significant inhibitory activity against two test plants, Lolium multiflorum (monocot) and Medicago sativa (dicot). The bioassay-directed chromatographic purification of the leaf extracts yielded three compounds, including one novel compound, identified using spectral data, as follows: (1) alpinolide peroxide, (2) 6-hydroxy alpinolide, and (3) 3-hydroxy-5-isopropyl-3-methyl-2,3-dihydro-1H-inden-1-one (a novel sesquiterpene). These compounds considerably limited the growth of L. sativum. The compound concentrations affecting a 50% growth limitation (IC50) of L. sativum varied from 0.16 to 0.34 mM. Therefore, these characterized compounds may be allelopathic agents that cause the allelopathy of C. oblongifolius.

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“…They have a more pungent odor and show anti-inammatory and antibacterial properties. 74,75 Aer oxidation, sesquiterpenes get converted into sesquiterpenols. 76 The a-methylene-g-lactone group (aMgL) of sesquiterpenes is responsible for anticarcinogenic and anti-inammatory activity, whereas helenalin causes anti-inammatory effects only and parthenolide accounts for antitumor activity.…”

Section: Sesquiterpenesmentioning

confidence: 99%

A review on terpenes for treatment of gastric cancer: current status and nanotechnology-enabled future

et al. 2023

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Analysis of sesquiterpenes and sesquiterpenoids

Cited by 11 publications

References 56 publications

De novo transcriptome analysis of Dysoxylum binectariferum to unravel the biosynthesis of pharmaceutically relevant specialized metabolites

De novo transcriptome analysis of Dysoxylum binectariferum to unravel the biosynthesis of pharmaceutically relevant specialized metabolites

Allelopathic Activity of a Novel Compound and Two Known Sesquiterpene from Croton oblongifolius Roxb.

A review on terpenes for treatment of gastric cancer: current status and nanotechnology-enabled future

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