Stereoselective metabolomic and lipidomic responses of lettuce (Lactuca sativa L.) exposing to chiral triazole fungicide tebuconazole

Zhao, Liuqing; Zhang, Yanwei; Wang, Lu; Liu, Xiaowei; Zhang, Jingran; He, Zhimin

doi:10.1016/j.foodchem.2021.131209

Cited by 18 publications

(6 citation statements)

References 34 publications

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“…The prominent therapeutic principle of TCM is holistic. network pharmacology provides a possible explanation for the multi-scale action mechanisms of TCM [39,40]. In this study, an interaction network based on metabolomics and network pharmacology analysis was constructed to fully understand the mechanism of ginseng on the spleen-Qi deficiency.…”

Section: Discussionmentioning

confidence: 99%

Metabolomics and network pharmacological analysis to explore the mechanism of ginseng treatment for spleen‐qi deficiency

Liu

Cai

et al. 2022

J of Separation Science

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Ginseng is the main Chinese herbal medicine for tonifying Qi and invigorating the spleen. It has been used to treat spleen‐qi deficiency with good protective effects for thousands of years, however, its biological mechanism has not been fully elucidated. This study aims to explore the mechanism of ginseng in the treatment of spleen‐qi deficiency by using a comprehensive method combining metabolomics and network pharmacological analysis. Gas chromatography‐mass spectroscopy was applied for investigating the changes in urine metabolites in spleen‐qi deficiency rats and after treatment with ginseng. Metabolomics and network pharmacology analysis were applied to screen potential biomarkers and therapeutic targets of ginseng in the treatment of spleen‐qi deficiency, respectively. Molecular docking was employed to further evaluate the docking mode of potential biomarkers and therapeutic target proteins. The results of metabolomics showed that the therapeutic effects of ginseng are mainly related to its regulation of three metabolic pathways. The molecular structure of potential biomarkers and common proteins was further analyzed by molecular docking to verify its effectiveness. Ginseng has good pharmacological effects by controlling key targets of related metabolic pathways, signal pathways, and potential biomarkers.

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Section: Discussionmentioning

confidence: 99%

Metabolomics and network pharmacological analysis to explore the mechanism of ginseng treatment for spleen‐qi deficiency

Liu

Cai

et al. 2022

J of Separation Science

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“…To identify the biomarker for various abiotic stresses, many studies have established more stringent filtering conditions for screening differential metabolites, such as fold change ≥ 2 or fold change ≤ 0.5, p-value < 0.05, and VIP ≥ 1 (30,31). Based on these biomarkers, possible metabolic pathways for edible oils when exposed to abiotic stresses would be clarified (15,17).…”

Section: Discussionmentioning

confidence: 99%

Comprehensive lipidomics analysis reveals the changes in lipid profile of camellia oil affected by insect damage

Zhang

Shen

et al. 2022

Front. Nutr.

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Information on changes in lipid composition of seed oils under biotic stresses is scare. The camellia weevil, Curculio chinensis (Coleoptera: Curculionidae) as a notorious seed predator of Camellia species, has caused huge economic losses in China. Lipidomics is used in this study to reveal the lipid composition of camellia oil and its changes after insect damage. 278 lipids including glycerolipids (GL) (221), glycerophospholipids (GP) (34), fatty acyls (FA) (13), sphingolipids (SP) (8), prenol lipids (PR) (1) and sterol lipids (ST) (1) were determined in camellia oils. Insect damage had a significant impact on lipids, particularly FA and GL. Ten significantly different lipids [FFA(18:2), FFA(24:6), TG(14:1/18:2/18:2), TG(16:0/23:0/18:2), TG(20:1/24:1/18:2), TG(18:2/24:0/18:2), TG(16:3/18:2/22:5), PI(16:1/18:1), PE(16:0/18:1), PE(18:1/18:2)] were identified as potential biomarkers for distinguishing oil extracted from non-infested oilseeds and oil from infested oilseeds. We also detected four most important metabolic pathways by bioinformatics analysis to explore the mechanisms underlying changes. Our findings may be useful for future camellia oil production and may provide new insight into improving of nutritional quality of camellia oil.

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“…5,8 For tebuconazole, (R)-tebuconazole showed the fungicidal activity to be 44-and 242-fold higher than (S)-tebuconazole to target the pathogens Botrytis cinerea 9 and Fusarium verticillioides, 2 respectively. In addition, (R)-tebuconazole obviously degraded faster than (S)-tebuconazole in grape and lettuce, 10,11 whereas it was slower in nontarget Danio rerio and in rat liver microsomes. 12,13 In spite of low acute toxicity, tebuconazole has been proven to induce chronic adrenal gland hypertrophy in dog, teratogenic effects in mice, and physiological impairment and endocrine disruption in male zebrafish.…”

Section: ■ Introductionmentioning

confidence: 93%

“…To date, various studies have demonstrated that chiral triazole fungicides exhibit significant stereoselective dissimilarities in target bioactivity, nontarget toxicity, bioaccumulation in organisms, and environmental behaviors. , For tebuconazole, ( R )-tebuconazole showed the fungicidal activity to be 44- and 242-fold higher than ( S )-tebuconazole to target the pathogens Botrytis cinerea and Fusarium verticillioides , respectively. In addition, ( R )-tebuconazole obviously degraded faster than ( S )-tebuconazole in grape and lettuce, , whereas it was slower in nontarget Danio rerio and in rat liver microsomes. , In spite of low acute toxicity, tebuconazole has been proven to induce chronic adrenal gland hypertrophy in dog, teratogenic effects in mice, and physiological impairment and endocrine disruption in male zebrafish. , More importantly, triazole fungicides could enter and accumulate in the human body through daily diet, posing risks to human health . For example, triazole fungicides have been found to exhibit the inhibition of human recombinant CYP19 (aromatase), potentially leading to disruption of normal endocrine homeostasis .…”

Section: Introductionmentioning

confidence: 99%

Chemoenzymatic Asymmetric Synthesis of Chiral Triazole Fungicide (R)-Tebuconazole in High Optical Purity Mediated by an Epoxide Hydrolase from Rhodotorula paludigensis

Hu,

Jia,

et al. 2024

J. Agric. Food Chem.

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Tebuconazole is a chiral triazole fungicide used globally in agriculture as a racemic mixture, but its enantiomers exhibit significant enantioselective dissimilarities in bioactivity and environmental behaviors. The steric hindrance caused by the tertbutyl group makes it a great challenge to synthesize tebuconazole enantiomers. Here, we designed a simple chemoenzymatic approach for the asymmetric synthesis of (R)-tebuconazole, which includes the biocatalytic resolution of racemic epoxy-precursor (2-tert-butyl-2-[2-(4-chlorophenyl)ethyl] oxirane, rac-1a) by Escherichia coli/Rpeh whole cells expressed epoxide hydrolase from Rhodotorula paludigensis (RpEH), followed by a one-step chemocatalytic synthesis of (R)-tebuconazole. It was observed that (S)-1a was preferentially hydrolyzed by E. coli/Rpeh, whereas (R)-1a was retained with a specific activity of 103.8 U/g wet cells and a moderate enantiomeric ratio (E value) of 13.4, which was remarkably improved to 43.8 after optimizing the reaction conditions. Additionally, a gram-scale resolution of 200 mM rac-1a was performed using 150 mg/mL E. coli/Rpeh wet cells, resulting in the retention of (R)-1a in a 97.0% ee s , a 42.5% yield s , and a 40.5 g/L/d space-time yield. Subsequently, the synthesis of highly optical purity (R)-tebuconazole (>99% ee) was easily achieved through the chemocatalytic ring-opening of the epoxy-precursor (R)-1a with 1,2,4-triazole. To elucidate insight into the enantioselectivity, molecular docking simulations revealed that the unique L-shaped substrate-binding pocket of RpEH plays a crucial role in the enantioselective recognition of bulky 2,2-disubstituted oxirane 1a.

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Stereoselective metabolomic and lipidomic responses of lettuce (Lactuca sativa L.) exposing to chiral triazole fungicide tebuconazole

Cited by 18 publications

References 34 publications

Metabolomics and network pharmacological analysis to explore the mechanism of ginseng treatment for spleen‐qi deficiency

Metabolomics and network pharmacological analysis to explore the mechanism of ginseng treatment for spleen‐qi deficiency

Comprehensive lipidomics analysis reveals the changes in lipid profile of camellia oil affected by insect damage

Chemoenzymatic Asymmetric Synthesis of Chiral Triazole Fungicide (R)-Tebuconazole in High Optical Purity Mediated by an Epoxide Hydrolase from Rhodotorula paludigensis

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