Molecular cloning and functional characterization of three terpene synthases from unripe fruit of black pepper (Piper nigrum)

Jin, Zhehao; Kwon, Min-Chul; Lee, Ahreum; Ro, Dae‐Kyun; Wungsintaweekul, Juraithip; Kim, Soo-Un

doi:10.1016/j.abb.2017.12.011

Cited by 16 publications

(7 citation statements)

References 31 publications

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“…The pnpks gene was identified through a CHS homology search on the black pepper (P. nigrum) fruit transcriptome data as described previously (Jin et al, 2018(Jin et al, , 2020. Gene-specific primer pairs were designed from the candidate genes to clone the respective open reading frames (ORFs) from the cDNA library.…”

Section: Isolation Of the Pnpks Genementioning

confidence: 99%

Construction of an Artificial Biosynthetic Pathway for the Styrylpyrone Compound 11-Methoxy-Bisnoryangonin Produced in Engineered Escherichia coli

et al. 2021

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A cDNA clone (named pnpks), which shows high homology to the known chalcone synthase (CHS)-like type III PKS, was obtained from the leaves of Piper nigrum. The PnPKS protein with ferulic acid catalyzed lactonization instead of chalcone or stilbene formation. The new product was characterized as a styrylpyrone, 11-methoxy-bisnoryangonin, which is the lactonization compound of a linear triketide formed as the reaction product of PnPKS protein with ferulic acid. These results show that pnpks encodes a styrylpyrone synthase (SPS)-like PKS that catalyzes two-chain elongation with feruloyl CoA-linked starter substrates. Although these styrylpyrone compounds are promising for use in human healthcare, they are mainly obtained by extraction from raw plant or mushroom sources. For de novo synthesis of 11-methoxy-bisnoryangonin in the heterologous host Escherichia coli from a simple sugar as a starter, the artificial biosynthetic pathway contained five genes: optal, sam5, com, and 4cl2nt, along with the pnpks gene. The engineered L-tyrosine overproducing E. coli ∆COS1 strain, in which five biosynthetic genes were cloned into two vectors, pET-opT5M and pET22-4P, was cultured for 24 h in a minimal glucose medium containing ampicillin and kanamycin. As a result, 11-methoxy-bisnoryangonin production of up to 52.8 mg/L was achieved, which is approximately 8.5-fold higher than that in the parental E. coli strain harboring a plasmid for 11-methoxy-bisnoryangonin biosynthesis. As a potential styrylpyrone compound, 11-methoxy-bisnoryangonin, was successfully produced in E. coli from a simple glucose medium, and its production titer was also increased using engineered strains. This study provides a useful reference for establishing the biological manufacture of styrylpyrone compounds.

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Section: Isolation Of the Pnpks Genementioning

confidence: 99%

Construction of an Artificial Biosynthetic Pathway for the Styrylpyrone Compound 11-Methoxy-Bisnoryangonin Produced in Engineered Escherichia coli

et al. 2021

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“…The scaffold of sesquiterpenes in plants is catalyzed by Terpene Synthases (TPS), which produce structurally distinct acyclic, mono-, bi- and tri-cyclic ST from common prenyl diphosphate precursors [ 31 ]. Genomic studies have associated the transcription of TPS genes to the ST profile in Myrtaceae [ 32 , 33 ], Lauraceae [ 34 , 35 ], and Piperaceae [ 36 ]. The shikimate pathway and phenylalanine biosynthesis from chorismate produce volatile benzenoids, although the information is from plant reproductive structures and does not include Lauraceae [ 37 ].…”

Section: Discussionmentioning

confidence: 99%

Essential Oils of Aromatic Plant Species from the Atlantic Rainforest Exhibit Extensive Chemical Diversity and Antimicrobial Activity

et al. 2022

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Microbial resistance, caused by the overuse or inadequate application of antibiotics, is a worldwide crisis, increasing the risk of treatment failure and healthcare costs. Plant essential oils (EOs) consist of hydrophobic metabolites with antimicrobial activity. The antimicrobial potential of the chemical diversity of plants from the Atlantic Rainforest remains scarcely characterized. In the current work, we determined the metabolite profile of the EOs from aromatic plants from nine locations and accessed their antimicrobial and biocidal activity by agar diffusion assays, minimum inhibitory concentration, time-kill and cell-component leakage assays. The pharmacokinetic properties of the EO compounds were investigated by in silico tools. More than a hundred metabolites were identified, mainly consisting of sesqui- and mono-terpenes. Individual plants and botanical families exhibited extensive chemical variations in their EO composition. Probabilistic models demonstrated that qualitative and quantitative differences contribute to chemical diversity, depending on the botanical family. The EOs exhibited antimicrobial biocidal activity against pathogenic bacteria, fungi and multiple predicted pharmacological targets. Our results demonstrate the antimicrobial potential of EOs from rainforest plants, indicate novel macromolecular targets, and contribute to highlighting the chemical diversity of native species.

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“…It provides a unique aroma to essential oils and plays a pivotal role in the survival and evolution of higher plants. This plant volatile compound is commonly found in grapes ( V. vinifera ) ( Schwab & Wust, 2015 ), rose myrtle ( Rhodomyrtus tomentosa ) ( He et al, 2018 ), black pepper ( P. nigrum ) ( Jin et al, 2018 ), cannabis ( Cannabis sativa ) ( Booth, Page, & Bohlmann, 2017 ), and Japanese chrysanthemum ( Chrysanthemum japonense ) ( Usami, Ono, Marumoto, & Miyazawa, 2013 ) . However, few studies have been conducted on aroma compounds, such as BCP, in B. campestris .…”

Section: Discussionmentioning

confidence: 99%

Transcriptome sequencing and gas chromatography–mass spectrometry analyses provide insights into β-caryophyllene biosynthesis in Brassica campestris

Wang

Zong

Bai

et al. 2022

Food Chemistry: Molecular Sciences

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Molecular cloning and functional characterization of three terpene synthases from unripe fruit of black pepper (Piper nigrum)

Cited by 16 publications

References 31 publications

Construction of an Artificial Biosynthetic Pathway for the Styrylpyrone Compound 11-Methoxy-Bisnoryangonin Produced in Engineered Escherichia coli

Construction of an Artificial Biosynthetic Pathway for the Styrylpyrone Compound 11-Methoxy-Bisnoryangonin Produced in Engineered Escherichia coli

Essential Oils of Aromatic Plant Species from the Atlantic Rainforest Exhibit Extensive Chemical Diversity and Antimicrobial Activity

Transcriptome sequencing and gas chromatography–mass spectrometry analyses provide insights into β-caryophyllene biosynthesis in Brassica campestris

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