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JOURNAL OF STORED PRODUCTS RESEARCH · 2024 · IF 2.7

Insect-resistant activities of Elsholtzia ciliata essential oil and its main components carvone against Tribolium castaneum in different development stages

Junyu Liang,Xiaohan Zhang,Qian Zhang,Yufei Tang,Weibao Kong,Ji Zhang,Yue An

The main objectives of the present study are to introduce a ecologically safe, and natural compound for controlling the red flour beetle , Tribolium castaneum . This study aims to thoroughly examine the effects of Elsholtzia ciliata essential oil ( E. ciliata EO) and its primary components, carvone , on Tribolium castaneum eggs, larvae, pupae, and adults. The study also includes a simulated warehouse test to assess the efficacy of these substances as contact agents, fumigants , repellents, and antifeedants. All of these anti-insect activities were positively correlated with the concentrations of E. ciliata EO and carvone. Firstly, in the contact activity assay, E. ciliata EO and carvone completely inhibited the hatching of eggs and pupae of the T. castaneum at a concentration of 2.5 μL/cm 2 . The LC 50 of E. ciliata EO and carvone were 7.62 and 4.33 μg/adult, respectively, against senior adults (5 weeks old). Secondly, in the fumigant activity assay, 60 mg/L of E. ciliata EO and carvone essentially completely inhibited pupae eclosion . On the other hand, the LD 50 of E. ciliata EO and carvone against senior adults (5 weeks old) were 8.72 and 5.02 mg/L, respectively. Thirdly, for T. castaneum adults, at the highest test concentration, the repellent rate of the E. ciliata EO was above 90%. Fourthly, the larvae and adults of the T. castaneum could reach complete antifeedant activity by E. ciliata EO and carvone at the highest test concentrations. Finally, 3000 ppm of carvone was sufficient to kill all the pests in the warehouse in the simulated warehouse test. In conclusion, the results of this study will contribute to the better control of the storage pest , T. castaneum , and the development of environmentally friendly insecticides based on E. ciliata EO and carvone.

研究领域: 昆虫学 · 植物化学 · 害虫防治
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Genes · 2022 ·Vol. 13 ·期 11 ·1956 · IF 4.141

Functional Study on Cytochrome P450 in Response to L(−)-Carvone Stress in Bursaphelenchus xylophilus

Jie Chen,Xin Hao,Ruina Tan,Yang Li,Bowen Wang,Jialiang Pan,Wei Ma,Ling Ma

Bursaphelenchus xylophilus(PWN) causes pine wilt disease (PWD), which is one of the most devastating pine diseases worldwide. Cytochrome P450 (CYP) catalyzes the biosynthetic metabolism of terpenoids and plays an important role in the modification of secondary metabolites in all living organisms. We investigated the molecular characteristics and biological functions ofBx-cyp29A3inB. xylophilus. The bioinformatics analysis results indicated thatBx-cyp29A3has a transmembrane domain and could dock with L(−)-carvone. The gene expression pattern indicated thatBx-cyp29A3was expressed in 0.2, 0.4, 0.6, 0.8, and 1.0 mg/mL L(−)-carvone solutions. TheBx-cyp29A3expression increased in a dose-dependent manner and peaked at 24 h of exposure when the L(−)-carvone solution concentration was 0.8 mg/mL. However, the gene expression peaked at 0.6 mg/mL after 36 h. Furthermore, RNA interference (RNAi) indicated thatBx-cyp29A3played an essential role in the response to L(−)-carvone. The mortality rates of theBx-cyp29A3knockdown groups were higher than those of the control groups in the 0.4, 0.6, 0.8, and 1.0 mg/mL carvone solutions after 24 h of exposure or 36 h of exposure. In summary, bioinformatics provided the structural characteristics and conserved sequence properties ofBx-cyp29A3and its encoded protein, which provided a target gene for the study of the P450 family ofB. xylophilus. Gene silencing experiments clarified the function ofBx-cyp29A3in the immune defense ofB. xylophilus.This study provides a basis for the screening of new molecular targets for the prevention and management ofB. xylophilus.Keywords:cytochrome P450;L(−)-carvone;Bursaphelenchus xylophilus;RNAi

CAS / MDL: 6485-40-1
研究领域: 分子生物学 · 植物病理学 · 线虫学
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BIOTECHNOLOGY AND APPLIED BIOCHEMISTRY · 2022 ·Vol. 70 ·期 2 ·697-706 · IF 2.724

Semi-rational protein engineering of a novel ene-reductase from Galdieria sulphuraria for asymmetric reduction of (R)-carvone and ketoisophorone

Shijin Wu,Bijiao Wang,Hongde Yan

Asymmetric reduction of ( R )-carvone and ketoisophorone by an engineered ene-reductase from Galdieria sulphuraria (GsOYE) combined with glucose dehydrogenase for NADPH regeneration were studied. A semi-rational protein engineering was used to enhance the activity and selectivity of GsOYE. Upon the sequence alignment and molecular docking results, two amino acid residues at positions 66 and 270 were selected as saturation mutation sites. Finally, a single substitution variant of GsOYE-N270A with complete conversion (100%) and diastereoselectivity (de p >99%) for reduction of ( R )-carvone and a double substitution variant GsOYE-Y66P/N270H with improved stereoselectivity for reduction of ketoisophorone were obtained.

CAS / MDL: 6485-40-1 1125-21-9
研究领域: 生物化学 · 蛋白质工程 · 催化 · 酶学
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Foods · 2025 ·Vol. 14 ·期 15 ·2645 · IF 5.1

Preparation and Characterization of D-Carvone-Doped Chitosan–Gelatin Bifunctional (Antioxidant and Antibacterial Properties) Film and Its Application in Xinjiang Ramen

Cong Zhang,Kai Jiang,Yilin Lin,Rui Cui,Hong Wu

In this study, a composite film with dual antioxidant and antibacterial properties was prepared by combining 2% chitosan and 7% gelatin (2:1, w:w), with D-carvone (0–4%) as the primary active component. The effect of D-carvone content on the performance of the composite films was systematically investigated. The results showed that adding 1% D-carvone increased the water contact angle by 28%, increased the elongation at break by 35%, and decreased the WVTR by 18%. FTIR and SEM confirmed that ≤2% D-carvone uniformly bonded with the substrate through hydrogen bonds, and the film was dense and non-porous. In addition, the DPPH scavenging rate of the 1–2% D-carvone composite film increased to about 30–40%, and the ABTS+scavenging rate increased to about 35–40%; the antibacterial effect on Escherichia coli and Staphylococcus aureus increased by more than 70%. However, when the addition amount was too high (exceeding 2%), the composite film became agglomerated, microporous, and phase-separated, affecting the film performance, and due to its own taste, it reduced the sensory quality of the noodles. Comprehensively, the composites showed better performance when the content of D-carvone was 1–2% and also the best effect for freshness preservation in Xinjiang ramen. This study provides a broad application prospect for natural terpene compound-based composite films in the field of high-moisture, multi-fat food preservation, and provides a theoretical basis and practical guidance for the development of efficient and safe food packaging materials. In the future, the composite film can be further optimized, and the effect of flavor can be further explored to meet the needs of different food preservation methods.

CAS / MDL: 9012-76-4
研究领域: 食品科学 · 高分子科学 · 材料工程 · 食品包装 · 抗菌技术 · 抗氧化研究
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FLAVOUR AND FRAGRANCE JOURNAL · 2022 ·Vol. 37 ·期 4 ·254-261 · IF 2.5

Study on green extraction of limonene from orange peel and cascade catalysis to produce carvol and carvone in deep eutectic solvents

Zongquan Li,Yunjian Ma,Frank Hollmann,Yonghua Wang

Carvol and carvone are oxidation products from the natural product limonene. They are important raw materials for the flavours and fragrances industry and also act as pharmaceutical active ingredients. Orange waste peels possibly represent an attractive source for limonene, but studies on valorizing orange peel wastes are rare. In this study, we report a new enzymatic cascade system for the in-situ conversion of limonene from orange peel into valued-added carvol and carvone. The use of deep eutectic solvents (DES) allows for efficient in-situ extraction of limonene from waste orange peels. We propose a dual function use of DES as solvent for the extraction and the biocatalytic oxidation of limonene as well as cosubstrate to promote the oxidation reaction. Using ChCl-Pro-H 2 O DES for the extraction of limonene from waste orange peels, approximately 17 milligrams of limonene per gram of orange peel was achieved at 40°C for 24 h. Then, with ChCl-Pro-H 2 O DES as the extractant and reaction medium, a cascade reaction system of choline oxidase (ChOx) and unspecific peroxygenase (UPO) was established to catalyse the conversion of limonene into carvol and carvone. The concentration of the final products was up to about 1.6 mmol L −1 . This study showed a biocatalytic transformation pathway and provides technical support for the high-value utilization of waste in orange peel.

研究领域: 生物化学 · 环境科学 · 香料工业
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Environmental Science-Nano · 2023 ·Vol. 10 ·期 12 ·3317-3328 · IF 7.3

Rational design and synthesis of L-carvone-derived 4-methyl-1,2,4-triazole-thioether/nanochitosan complexes as potent nanopesticides for sustainable and efficient herbicidal application

Baoyu Li,Wengui Duan,Guishan Lin,Yucheng Cui,Rongzhu Wen,Chuwen Liu,Yulu Xie

Natural product-based nanopesticide is an effective and sustainable approach for solving the environmental issues caused by the application of current commercial herbicides. In this study, 21 novel L-carvone-derived 4-methyl-1,2,4-triazole-thioether derivatives 5a–5u were rationally designed by transketolase-based in silicon virtual screening, synthesized, and structurally characterized using FT-IR spectroscopy, 1H/13C NMR spectroscopy, and HRMS technique. Besides, the herbicidal activity of the target compounds against Brassica campestris and Echinochloa crusgalli L. was evaluated, and the bioassay results revealed that compound 5a with the most significant herbicidal and TK-inhibition activities could serve as a potential TK inhibitor and could serve as a leading compound for further study of green herbicides. Subsequently, the molecular skeletons of chitosan and L-carvone were incorporated for developing high-efficiency nanopesticide carriers, and thus samples 7a–7d were synthesized by N-alkylation of chitosan and characterized using various methods. Compared with unmodified chitosan, L-carvone-derived nanochitosan carrier 7b with the micro-morphologies of nubby lumps and porous surfaces exhibited higher dispersibility and similar thermostability. Finally, L-carvone-derived 4-methyl-1,2,4-triazole-thioether/nanochitosan complexes 7b/5a, 7c/5a, and 7d/5a with better 5a-loading capacities and multi-stage sustained releasing performances were constructed, and the herbicidal activities of 7b/5a and 7d/5a against Brassica campestris were evaluated in the petri dish and greenhouse. It was found that 7b/5a and 7d/5a exhibited significant herbicidal activities. Among them, 7b/5a had great potential as a green and eco-friendly nanopesticide for weed control.

研究领域: 植物学 · 农业科学 · 材料科学
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Journal of Materials Chemistry A · 2024 · IF 10.7

“Polymer to polymer” recycling and body-temperature triggered shape memory of a carvone-based epoxy thermoset system achieved using a thiol-Michael covalent adaptable network

Beitao Liu,Jiahui Li,Cijian Zhang,Yibo Wang,Xigao Jian,Zhihuan Weng

Environmental economics is intensifying the necessity for the advancement of recycling technologies to address the increasing volume of discarded thermoset polymers. Covalent adaptable networks (CANs) provide a new strategy for the recycling and functionalization of thermosetting resins. Herein, a carvone-based CAN is developed, in which thermally driven depolymerization of mechanically robust polymer networks is achieved by dynamic thiol-Michael bonds. The original cross-linking network can be retained through simple drying and hot-pressing steps without purifying degradation products. The reversibility of the thiol-Michael group is demonstrated and the CAN exhibits shape memory behaviors triggered by human body temperature. We propose a micro-robotic injection model with good mechanical strength and fast response speed for complex 1D to 3D shape morphing in aqueous media at 37 °C. Our findings present a high-quality strategy to realize recycling and functionalization of bio-based thermoset resins and expand the toolbox for the preparation of bio-based CANs with thermo-responsive behavior.

研究领域: 材料科学 · 聚合物化学 · 可持续材料 · 回收技术
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