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INDUSTRIAL CROPS AND PRODUCTS · 2021 · IF 5.645

Insecticidal activities of Salvia hispanica L. essential oil and combinations of their main compounds against the beet armyworm Spodoptera exigua

Yijuan Chen,Jiaxuan Luo,Nan Zhang,Wenjuan Yu,Jiexian Jiang,Guanghui Dai

Plant essential oils are the powerful candidates to develop natural insect management agents. Their chemical compounds along with their biological activity are often affected by many factors. However, the relationships between the composition and bioactivity of the compounds are not well understood. In this study, eight plant essential oils were screened, and the main compounds from the most effective oil showing insecticidal properties against third-instar larvae of the beet armyworm ( Spodoptera exigua Hübner) were evaluated for comparative and synergistic interactions by topical application. The results indicated that Salvia hispanica L. essential oil showed significant insecticidal activity against S. exigua compared with the other seven essential oils. Fifteen major compounds were identified from S. hispanica via gas chromatography-mass spectrometry, with the most abundant compound (α-thujone) possessing the highest insecticidal activity. Several combinations of the four major compounds (α-thujone, (+)-camphor, 1,8-cineole, and α-caryophyllene) from S. hispanica exhibited synergistic insecticidal activities. This study demonstrates the potential of S. hispanica essential oil and α-thujone as effective botanical insecticides in the control of beet armyworm and provides a better understanding of essential oil compound-pest interactions.

CAS / MDL: 18172-67-3
研究领域: 植物学 · 昆虫学 · 农业科学
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JOURNAL OF FOOD SCIENCE · 2021 ·Vol. 86 ·期 10 ·4554-4565 · IF 3.167

Nanoparticle-stabilized encapsulation of borneol and citral: Physicochemical characteristics, storage stability, and enhanced antibacterial activities

Wen Wang,Zhihui Ren,Li Wang,Ying Cai,Hang Ma,Liming Fang,Jianyu Su

Combinations of phytochemical(s) and engineered nanoparticles have attracted immense research interest due to their superior antimicrobial effects against contaminations. Herein, a Pickering emulsion is developed with capsulized phytochemicals including borneol and citral (BC–Cap) stabilized by hydrophilic amine-functionalized silica nanoparticles (SiO 2 ─NH 2 NPs). The droplet sizes of Pickering emulsion were 5.2 ± 1.4 µm under the condition that the concentrations of SiO 2 ─NH 2 NPs ranged from 0.6 to 1.2 wt.%, and the emulsion showed desirable stability during storage at 40°C for 365 days. In addition, the antibacterial and antibiofilm activities of the Pickering emulsion were investigated. The antibacterial effect of BC–Cap increased by two- to fourfold compared with citral or borneol alone. Treatment of BC/BC–Cap for 4 h eliminated the formation of biofilms generated by Listeria monocytogenes (at 5/1.25 mg/ml; 2 × MIC concentration) and Pseudomonas aeruginosa (at 5/2.5 mg/ml; 2 × MIC concentration). Further mechanistic studies revealed that the antibiofilm effects of BC–Cap were attributed to its ability to increase the porosity and lytic effects on the cell membrane of bacteria. Findings from the current study support the antibacterial and antibiofilm effects of BC–Cap Pickering emulsion as a promising food additive. Practical Application The Pickering emulsion has potential applications as bacteriostatic agent in packaging materials and general surface disinfectant. The combination of borneol and citral is stabilized by hydrophilic amine-functionalized silica nanoparticles (SiO 2 ─NH 2 NPs). With the synergistic effects of borneol and citral, the Pickering emulsion shows a promising elimination effect against the formation of biofilms produced by Listeria monocytogenes and Pseudomonas aeruginosa .

研究领域: 食品科学 · 纳米技术 · 微生物学
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SOUTH AFRICAN JOURNAL OF BOTANY · 2021 · IF 2.315

A new neolignan and a new biphenylpropanoid from the leaves of Cupressus funebris Endl.

Si-Yu Zhong,Hong-Yu Jiang,Li-Ping Wu,Meng-Ying Liu,Ya-Rui Yu,Cheng-Rong Li,Jing Huang

A new neolignan, (-)-(7 S , 8 R )-3‑methoxy-4', 7-epoxy-8, 5'-neolignane-5, 9, 3', 9′-tetraol ( 1 ) and a new biphenylpropanoid, 1, 2-epoxy-1-(3', 4'-dihydroxyphenyl-)-3-(2'', 3'', 5''-trihydroxyphenyl-) propane ( 2 ), together with eight known compounds ( 3-10 ), were isolated from the 95% EtOH extract of the leaves of Cupressus funebris Endl . Their structures were determined by spectroscopic methods including NMR, circular dichroism (CD) spectra and comparison of the NMR data with reported in references. The antioxidant activities of all compounds were evaluated by DPPH, ABTS, and FRAP methods. Compounds 2 (IC 50 : 33.98 ± 0.11 μM), 3 (IC 50 : 32.97 ± 0.63 μM), 8 (IC 50 : 32.07 ± 1.57 μM), and 9 (IC 50 : 33.30 ± 2.29 μM) showed stronger DPPH free radical scavenging activity than l -ascorbic acid (IC 50 : 64.31 ± 1.32 μM). Except for 4 , the other compounds showed ABTS radical scavenging abilities comparable to l -ascorbic acid (54.91 ± 1.18 μM) with the IC 50 ranged from 24.42 ± 1.78 μM to 138.70 ± 13.58 μM. Compound 3 (0.72 ± 0.02 mmol/g) showed the same ferric reducing antioxidant power (FRAP) as l -ascorbic acid (0.83±0.02 mmol/g).

CAS / MDL: 28752-68-3
研究领域: 药用植物学 · 天然产物化学 · 生物化学
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FOOD AND CHEMICAL TOXICOLOGY · 2021 · IF 6.025

Mechanistic study of bergamottin-induced inactivation of CYP2C9

Ying Liu,Shiyu Zhang,Tingting Jiang,Rong Tan,Yao Fu,Xiaojing Yang,Bowen Gong,Ying Zou,Weiwei Li,Jiang Zheng

Bergamottin (BGM) is a major furanocoumarin constituent of grapefruit and is reported to have inhibitory effects on cytochrome P450 enzymes. This study investigated the chemical interactions between BGM and the enzyme CYP2C9 . BGM exhibited time-, concentration-, and NADPH-dependent inhibition of CYP2C9. Co-incubation with diclofenac, a reversible inhibitor of CYP2C9, attenuated the time-dependent enzyme inhibition. Exhaustive dialysis did not restore enzyme activity post-inhibition. Glutathione (GSH) and catalase/superoxide dismutase failed to reverse BGM-induced CYP2C9 inactivation. A GSH trapping study suggested that BGM was metabolized to an epoxide and/or γ-ketoenal that may have been responsible for the enzyme inactivation. In conclusion, BGM can be characterized as a mechanism-based inactivator of CYP2C9 acting via the formation of an epoxide and/or γ-ketoenal.

研究领域: 药理学 · 生物化学 · 毒理学
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Frontiers in Plant Science · 2016 · IF 4.495

Cloning, Functional Characterization, and Catalytic Mechanism of a Bergaptol O-Methyltransferase from Peucedanum praeruptorum Dunn

Zhao Yucheng,Wang Nana,Zeng Zhixiong,Xu Sheng,Huang Chuanlong,Wang Wei,Liu Tingting,Luo Jun,Kong Lingyi

Coumarins are main active components of Peucedanum praeruptorum Dunn. Among them, methoxylated coumarin compound, such as bergapten, xanthotoxin, and isopimpinellin, has high officinal value and plays an important role in medicinal field. However, major issues associated with the biosynthesis mechanism of coumarins remain unsolved and no corresponding enzyme has been cloned from P. praeruptorum. In this study, a local BLASTN program was conducted to find the candidate genes from P. praeruptorum transcriptome database using the nucleotide sequence of Ammi majus bergaptol O-methyltransferase (AmBMT, GenBank accession No: AY443006) as a template. As a result, a 1335 bp full-length of cDNA sequence which contains an open reading frame of 1080 bp encoding a BMT polypeptide of 359 amino acids was obtained. The recombinant protein was functionally expressed in Escherichia coli and displayed an observed activity to bergaptol. In vitro experiments show that the protein has narrow substrate specificity for bergaptol. Expression profile indicated that the cloned gene had a higher expression level in roots and can be induced by methyl jasmonate (MeJA). Subcellular localization analysis showed that the BMT protein was located in cytoplasm in planta. Homology modeling and docking based site-directed mutagenesis have been employed to investigate the amino acid residues in BMT required for substrate binding and catalysis. Conservative amino acid substitutions at residue H264 affected BMT catalysis, whereas substitutions at residues F171, M175, D226, and L312 affected substrate binding. The systemic study summarized here will enlarge our knowledge on OMTs and provide useful information in investigating the coumarins biosynthesis mechanism in P. praeruptorum.

研究领域: 植物生物化学 · 分子生物学 · 生药学 · 酶学
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MEDICINAL CHEMISTRY RESEARCH · 2020 ·Vol. 29 ·期 7 ·1230-1237 · IF 1.783

Bergaptol, a mechanism-based inactivator of CYP2C9

Jiang Tingting,Cheng Ting,Li Jing,Zhou Mengyue,Tan Rong,Yang Xiaojing,Wang Yang,Li Weiwei,Zheng Jiang

Grapefruit-mediated fruit–drug interaction has been well discussed in clinical practice. However, the biochemical mechanisms for such interaction are far beyond our understanding. The objectives of the present study aimed at the interaction between bergaptol (BGT) and CYP2C9. BGT, one of the major furanocoumarin constituents in grapefruit, has been reported to inhibit the activity of CYP2C9. And a number of furan-containing compounds are known to act as mechanism-based inactivators of CYP2C9. In this study, BGT was found to induce time-, concentration-, and NADPH-dependent irreversible inhibition of CYP2C9. A GSH conjugate was detected in an incubation mixture containing CYP2C9, BGT, NADPH, and GSH. Further mechanistic investigation revealed that a γ-ketoenal metabolite was responsible for the enzyme inactivation. The obtained data indicate that BGT was a mechanism-based inactivator of CYP2C9. The study would facilitate the understanding of the mechanistic insight into fruit–drug interactions mediated by grapefruits.

研究领域: 药理学 · 生物化学 · 临床药理学
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INTERNATIONAL JOURNAL OF FOOD PROPERTIES · 2023 · IF 2.9

Chemical composition and bioactivities of the essential oil of Coreopsis tinctoria and Chrysanthemum morifolium

Zhong-Rong Jiang,Ting Zhang,Ling-Bo Ji,Lei Wu,Hong-Hui Dong,Guo-Liang Zhao,Hong-Qian Shentu,Bao-Jiang He,Tian-Xiao Li

This study was aiming at the differences in the aroma, flavor compounds, and bioactivities of essential oil of Coreopsis tinctoria flower (CTFEO) and essential oil of Chrysanthemum morifolium flower (CMFEO). Both essential oils were extracted by steam distillation. Their flavor compositions were determined by GC-MS and the antioxidant, antibacterial, and anti-inflammatory activities were also evaluated. It was found that CTFEO possessed a special medicinal herb odor, which was obviously stronger than those of CMFEO. A preferred condition for steam distillation was flower powder–water ratio of 7.5:100 and extraction for more than 3.0 h. Interestingly, the main flavor compounds of CTFEO were determined as D-limonene (34.54%), cis-carveol (5.49%), trans-α-bergamotene (4.44%), and α-pinene (3.90%), which were quite different from those of CMFEO. CTFEO showed better antioxidant activities with IC50 value of 121.4 ± 9.8 μg/mL than those of CMFEO. It also exhibited stronger antibacterial effects than those of CMFEO, with minimal inhibitory concentrations (MICs) ranging from 0.183 to 1.412 mg/mL against six strains of bacteria. Moreover, CTFEO was also found to exhibit strong anti-inflammatory effects that reduced the LPS-induced RAW 264.7 cell mRNA expression of the cytokines IL-1β, IL-6, and TNF-α at a concentration of 10.0 μg/mL. All these results suggest that the aroma, flavor compounds, and bioactivities of the two essential oils were quite different and they could be used as tea, drink, and food additive in the food industry for further development.

研究领域: 植物学 · 药理学 · 食品科学
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