Efficacy and mechanism of Mentha haplocalyx and Schizonepeta tenuifolia essential oils on the inhibition of Panax notoginseng pathogens

Chen, Chuan‐Jiao; Li, Qingqing; Zeng, Zi-Ying; Duan, Su-Su; Wang, Wei; Xu, Furong; Cheng, Yong‐Xian; Dong, Xian

doi:10.1016/j.indcrop.2019.112073

Cited by 25 publications

(22 citation statements)

References 49 publications

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“…Pulegone reductase from Mentha piperita (MpPR) that catalyzes the reduction of the C2-C8 double bond of (+)-pulegone to (−)menthone using NADP(H) as a co-factor has been established for decades (Lange, 2015). Besides M. piperita, many other medicinal herbs, such as Nepeta tenuifolia and Agastache rugosa are also producers of essential oils, in which menthone and menthol are the major components (Chen et al, 2019). Intriguingly, it has been reported that N. tenuifolia and A. rugosa produce (+)menthone and (+)-menthol as the major metabolites, in contrast to M. piperita that predominantly biosynthesizes (−)-menthone and (−)-menthol (Chen et al, 2019).…”

Section: Resultsmentioning

confidence: 99%

“…(−)-Menthone, the second most abundant monoterpenoid in peppermint essential oil, is a critical intermediate in menthol biosynthesis ( Lange, 2015 ; Chen et al, 2019 ). In Mentha piperita , (−)-menthone is directly synthesized from (+)-pulegone through the reduction of C2–C8 alkene double bond catalyzed by (+)-pulegone reductase (EC number 1.3.1.81).…”

Section: Introductionmentioning

confidence: 99%

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Functional Characterization and Structural Insights Into Stereoselectivity of Pulegone Reductase in Menthol Biosynthesis

et al. 2021

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Monoterpenoids are the main components of plant essential oils and the active components of some traditional Chinese medicinal herbs like Mentha haplocalyx Briq., Nepeta tenuifolia Briq., Perilla frutescens (L.) Britt and Pogostemin cablin (Blanco) Benth. Pulegone reductase is the key enzyme in the biosynthesis of menthol and is required for the stereoselective reduction of the Δ2,8 double bond of pulegone to produce the major intermediate menthone, thus determining the stereochemistry of menthol. However, the structural basis and mechanism underlying the stereoselectivity of pulegone reductase remain poorly understood. In this study, we characterized a novel (−)-pulegone reductase from Nepeta tenuifolia (NtPR), which can catalyze (−)-pulegone to (+)-menthone and (−)-isomenthone through our RNA-seq, bioinformatic analysis in combination with in vitro enzyme activity assay, and determined the structure of (+)-pulegone reductase from M. piperita (MpPR) by using X-ray crystallography, molecular modeling and docking, site-directed mutagenesis, molecular dynamics simulations, and biochemical analysis. We identified and validated the critical residues in the crystal structure of MpPR involved in the binding of the substrate pulegone. We also further identified that residues Leu56, Val282, and Val284 determine the stereoselectivity of the substrate pulegone, and mainly contributes to the product stereoselectivity. This work not only provides a starting point for the understanding of stereoselectivity of pulegone reductases, but also offers a basis for the engineering of menthone/menthol biosynthetic enzymes to achieve high-titer, industrial-scale production of enantiomerically pure products.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Functional Characterization and Structural Insights Into Stereoselectivity of Pulegone Reductase in Menthol Biosynthesis

et al. 2021

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“…An injured plasma membrane may result in a leakage of cellular components, including nucleic acids and proteins, and cellular collapse until death, representing the mode of action underlying the biostatic and biocidal EOs effects [106]. EOs also may induce decreased Succinate dehydrogenase (SDH) and nicotinamide adenine dinucleotide hydride (NADH) oxidase activities and cause extreme changes in ultra-structures by penetrating and dissolving the mitochondrial membranes [107]. The exposure of Escherichia coli and Staphyloccocus aureus to Salvia sclarea EO caused cell plasmalemma disintegration with a massive leakage of cellular material and reduction of the intracellular ATP, as well as nuclear DNA content [108].…”

Section: Sage Essential Oilsmentioning

confidence: 99%

Sage Species Case Study on a Spontaneous Mediterranean Plant to Control Phytopathogenic Fungi and Bacteria

Zaccardelli

Pane

Caputo

et al. 2020

Forests

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Sage species belong to the family of Labiatae/Lamiaceae and are diffused worldwide. More than 900 species of sage have been identified, and many of them are used for different purposes, i.e., culinary uses, traditional medicines and natural remedies and cosmetic applications. Another use of sage is the application of non-distilled sage extracts and essential oils to control phytopathogenic bacteria and fungi, for a sustainable, environmentally friendly agriculture. Biocidal propriety of non-distilled extracts and essential oils of sage are w documented. Antimicrobial effects of these sage extracts/essential oils depend on both sage species and bacteria and fungi species to control. In general, it is possible to choose some specific extracts/essential oils to control specific phytopathogenic bacteria or fungi. In this context, the use of nanotechnology techniques applied to essential oil from salvia could represent a future direction for improving the performance of eco-compatible and sustainable plant defence and represents a great challenge for the future.

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“…The damage of plant pathogenic fungi is one of the main reasons for the decrease of crop yield. 1,2 Crops once infected by pathogenic fungi will cause a large reduction in production, slow growth and death, and finally lead to incalculable economic loss. [3][4][5] Chemical pesticides are often used to control plant diseases in agriculture.…”

Section: Introductionmentioning

confidence: 99%

Discovery of zeylenone from Uvaria grandiflora as a potential botanical fungicide

Dou

Xie

et al. 2021

Pest Management Science

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BACKGROUND: Botanical pesticides play an important role in organic agricultural practices and are widely used in integrated pest management (IPM). Uvaria grandiflora was mainly reported as traditional medicines and possessed antibacterial, antioxidant, and antiprotozoal activities. Therefore, important biological activities of U. grandiflora may suggest that they have the potential to be used as botanical pesticides.RESULTS: The extract of U. grandiflora exhibited broad-spectrum inhibitory activity toward phytopathogenic fungi and oomycetes, particularly against Colletotrichum musae and Phytophthora capsici, and its secondary metabolite zeylenone also displayed strong antifungal and anti-oomycete activities against phytopathogens. Particularly, half maximal effective concentration (EC 50 ) values of zeylenone against Phytophthora capsici and C. musae were 6.98 and 3.37 ∼g mL −1 , showing better inhibitory effects than those of commercial fungicides (azoxystrobin and osthole). Additionally, the pot experiments showed that the extract of U. grandiflora could effectively control Pseudoperonospora cubensis, Phytophthora infestans, Phytophthora capsici and Podosphaera xanthii. In the field experiment, 5% microemulsion of U. grandiflora extract exhibited 79.72% efficacy against cucumber powdery mildew at 87.5 g ha −1 on the 14th day after two sprayings, which was better than that of 21.5% trifloxystrobin and 21.5% fluopyram SC at 200.9 g ha −1 . Surprisingly, 5% microemulsion of U. grandiflora extract could promote cucumber growth significantly. Furthermore, the action mechanism analysis indicated that zeylenone may damage the cytoderm and affect energy metabolism of Phytophthora capsici.CONCLUSION: It is the first time that the extract of U. grandiflora and zeylenone have been discovered leading to broad application prospects in the development as botanical fungicides.

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Efficacy and mechanism of Mentha haplocalyx and Schizonepeta tenuifolia essential oils on the inhibition of Panax notoginseng pathogens

Cited by 25 publications

References 49 publications

Functional Characterization and Structural Insights Into Stereoselectivity of Pulegone Reductase in Menthol Biosynthesis

Functional Characterization and Structural Insights Into Stereoselectivity of Pulegone Reductase in Menthol Biosynthesis

Sage Species Case Study on a Spontaneous Mediterranean Plant to Control Phytopathogenic Fungi and Bacteria

Discovery of zeylenone from Uvaria grandiflora as a potential botanical fungicide

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