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MOLECULES · 2017 ·Vol. 22 ·期 11 ·1914 · IF 2.861

Evaluating the Potential Value of Natural Product Cuminic Acid against Plant Pathogenic Fungi in Cucumber

Yong Wang,Jie Zhang,Yang Sun,Juntao Feng,Xing Zhang

Fusarium wilt and anthracnose are two major diseases which limit the yield and quality of cucumber worldwide. Cuminic acid was extracted from the seed ofCuminum cyminumL. The mean EC50values of cuminic acid for inhibiting mycelial growth and zoospore germination of fiveFusarium oxysporumf. sp.cucumerinumstrains were 25.66 ± 3.02 μg/mL and 15.99 ± 2.19 μg/mL, and of fourColletotrichum lagenarium(Pass.) Ellis and Halsted strains were 29.53 ± 3.18 μg/mL and 18.41 ± 2.78 μg/mL, respectively. In greenhouse experiments, cuminic acid at 2000 μg/mL exhibited 70.77% protective and 62.63% curative efficacies againstF. oxysporum, and 65.43% protective and 55.46% curative efficacies againstC. lagenarium. Moreover, the translocation behavior of cuminic acid, determined by high performance liquid chromatography (HPLC), showed that it could be readily absorbed and transported upward and downward in cucumber. Importantly, superoxide dismutase (SOD) and pyphenol oxidase (PPO) activities of cucumber leaves treated with cuminic acid increased significantly. All results indicated that cuminic acid showed antifungal activity, and could be used as a botanical fungicide in disease management. This study encourages further investigation on the mechanism of action of cuminic acid and the development of alternative antifungal drugs.Keywords:botanical fungicide;cuminic acid;cucumber;F. oxysporum;C. lagenarium;control efficacy

研究领域: 植物保护 · 分子生物学
✓ 已验证 DOI PubMed 高影响因子
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INDUSTRIAL CROPS AND PRODUCTS · 2017 · IF 3.181

Application of sustainable natural resources in crop protection: Podophyllotoxin-based botanical pesticides derived from Podophyllum hexandrum for controlling crop-threatening insect pests

Ruige Yang,Xiaobo Huang,Zhiping Che,Yuanyuan Zhang,Hui Xu

Podophyllotoxin is isolated as a sustainable natural bioresource from the roots and rhizomes of Podophyllum hexandrum and Juniperus Sabina . In continuation of our program aimed at the discovery of biorenewable natural product-based pesticides, a series of 4α-acyloxy derivatives of 2'-chloro-5-bromopicropodophyllotoxin or 2',5-dibromopicropodophyllotoxin were synthesized by structural modification of podophyllotoxin, and evaluated as insecticidal and acaricidal agents against two serious agricultural pests, Mythimna separata Walker and Tetranychus cinnabarinus Boisduval. Among all derivatives, compounds 6a and 7a exhibited more promising insecticidal and acaricidal activities than podophyllotoxin, and the final mortality rates of 6a , 7a and 1 against M. separata (at 1   mg/mL) and T. cinnabarinus (at 0.5   mg/mL) were 50%/53.3%/36.7%, and 33%/41.8%/1.6%, respectively. This suggested that introduction of the acetoxy moiety at the C-4 position of 2'-chloro-5-bromopicropodophyllotoxin/2',5-dibromopicropodophyllotoxin was necessary for the insecticidal and acaricidal activities.

CAS / MDL: 538-75-0 1122-58-3
研究领域: 植物化学 · 害虫管理 · 农业科学
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MOLECULES · 2016 ·Vol. 21 ·期 10 ·1359 · IF 2.465

Chemical Compositions of Ligusticum chuanxiong Oil and Lemongrass Oil and Their Joint Action against Aphis citricola Van Der Goot (Hemiptera: Aphididae)

Chao Zhang,Runqiang Liu,Jun He,Zhiqing Ma,Xing Zhang

In order to develop novel botanical insecticides, the joint action ofLigusticum chuanxiongoil (LCO) and lemongrass oil (LO) againstAphis citricolavan der Goot was determined systematically indoors and outdoors. The chemical profiles of LCO and LO as determined by gas chromatography–mass spectrometry (GC-MS) analysis revealed that the main compounds from LCO were (Z)-ligustilide (44.58%) and senkyunolide A (26.92%), and that of LO were geranial (42.16%) and neral (32.58%), respectively. The mixture of LCO and LO showed significant synergy againstA. citricola, with a common-toxicity coefficient (CTC) value of 221.46 at the optimal ratio of LCO to LO (4:1,w:w). Based on the results of solvents and emulsifiers screening,L. chuanxiongoil·Lemongrass oil 20% emulsifiable concentrate (20% LCO·LO EC) was developed, and its stability was confirmed with tests of cold and thermal storage. Field trials indicated that the insecticidal activity of the diluted 20% LCO·LO EC (1000 fold dilution) was comparable to conventional pesticide (20% imidacloprid EC) onA. citricolaseven days after application. Thus, the mixture of LCO and LO has the potential to be further developed as a botanical pesticide.Keywords:lemongrass oil;Ligusticum chuanxiongoil;Aphis citricolavan der Goot;botanical aphicides

研究领域: 植物学 · 昆虫学 · 农业科学
✓ 已验证 DOI PubMed 高影响因子
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ACS Omega · 2021 · IF 3.512

Trace Analysis of Fenbutatin Oxide in Soil and Plant- and Animal-Derived Foods Using Modified QuEChERS Coupled with HPLC-MS/MS

Zhihui Lin,Yingnan Lin,Jianqi Lin,Yizhi Zhang,Song Fang

A modified QuEChERS method in combination with high-performance liquid chromatography-tandem mass spectrometry (HPLC-MS/MS) was first developed for the determination of fenbutatin oxide in six types of samples (soil, tobacco, rice, milk, pork liver, and pork). Fenbutatin oxide was extracted with acetonitrile containing 1% formic acid (v/v) and purified by dispersive solid-phase extraction using primary secondary amine (PSA) and quantitatively analyzed by HPLC-MS/MS. In the range of 0.005–1 mg/kg, a good linear relationship exists between the concentration of fenbutatin oxide and the peak area, giving a coefficient of determination (R2) of >0.99. The recoveries of fenbutatin oxide at three spiked levels were 79.04–97.12% with the relative standard deviations (RSDs) of 3.30–10.96%, and the limit of quantification (LOQ) was 0.007 mg/kg. In addition, the developed method is consistent with the reference method (R2 = 0.9896, n = 40). The method is demonstrated to be convenient and reliable for the routine monitoring of fenbutatin oxide in soil and plant- and animal-derived foods.

CAS / MDL: 13356-08-6
研究领域: 分析化学 · 食品安全
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2022 · IF 5.895

Preparation and Biological Evaluation of Novel Osthole-Derived N-Benzoylthioureas as Insecticide Candidates

Ruige Yang,Zhiyan Liu,Meiyue Han,Liping Cui,Yong Guo

To discover novel natural-product-based insecticide candidates, herein, a variety of osthole-derived N-benzoylthioureas were synthesized and assessed for their insecticidal activities against three insect pests. An insecticidal assay showed that most of the target osthole-derived N-benzoylthioureas displayed a more potent and broad-spectrum insecticidal effect than the parent osthole after the introduction of N-benzoylthioureas on the C-3′ position of osthole. Compound B24 displayed the most potent growth inhibitory (GI) effect on Mythimna separata Walker, with a final corrected mortality rate of 82.1% when treated with a concentration of 1 mg/mL, which was 1.64- and 1.53-fold higher in comparison to osthole and the botanical insecticide toosendanin, respectively. Compounds B22, B23, and B25 displayed a more promising aphicidal effect on Myzus persicae Sulzer, and their LD50 values were 0.015, 0.017, and 0.019 μg/larvae, respectively, superior to the commercially available insecticide rotenone (0.024 μg/larvae). Derivatives B19, B20, B23, and B25 displayed more potent larvicidal activity against Plutella xylostella Linnaeus, with LC50 values of 0.22, 0.26, 0.15, and 0.30 mg/mL, respectively, exceeding that of rotenone (0.37 mg/mL). Furthermore, both compounds B19 and B23 against P. xylostella were found to be more effective than rotenone in a control efficacy assay under greenhouse conditions. The structure–activity relationship (SAR) suggested that osthole-derived N-benzoylthioureas are more active in most cases when the R group is an electron-withdrawing group than when it is an electron-donating group, especially for halogenated groups. Additionally, the potent compounds B19 and B23 possessed good selectivity and were less toxic to non-target organisms. This study suggests that these osthole-derived N-benzoylthioureas could be further studied in depth as eco-friendly natural product pesticides in crop protection.

研究领域: 昆虫学 · 有机化学 · 农药科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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BIOMEDICAL CHROMATOGRAPHY · 2021 ·Vol. 36 ·期 1 ·e5229 · IF 1.902

Enantioselective determination of phenthoate enantiomers in plant-origin matrices using reversed-phase high-performance liquid chromatography–tandem mass spectrometry

Chao Dong,Jie Zhou,Wei Zuo,Zhixia Li,Jing Li,Bining Jiao

Phenthoate is a chiral organophosphate pesticide with a pair of enantiomers which differ in toxicity, behavior and insecticidal activity, and its acute toxicity on human health owing to the inhibition of acetylcholinesterase highlights the need for enantioselective detection of enantiomers. Therefore, this study aimed to establish a simple rapid method for separation and detection of phenthoate enantiomers in fruits, vegetables and grains. The enantiomers were separated using reversed-phase high-performance liquid chromatography–tandem mass spectrometry for the first time. Rapid chiral separation (within 9 min) of the target compound was achieved on a chiral OJ-RH column with the mobile phase of methanol–water = 85:15(v/v), at a flow rate of 1 ml/min and a column temperature of 30°C. Acetonitrile and graphitized carbon black were used as the extractant and sorbent for pretreatment, respectively. This method provides excellent linearity (correlation coefficient ≥0.9986), high sensitivity (limit of quantification 5 μg/kg and limit of detection <0.25 μg/kg), satisfactory mean recoveries (76.2–91.0%) and relative standard deviation (intra-day RSDs ranged from 2.0 to 7.9% and inter-day RSDs ranged from 2.4 to 8.4%). In addition, a field trial to explore the stereoselective degradation of phenthoate enantiomers in citrus showed that (−)-phenthoate degraded faster than its antipode, resulting in the relative accumulation of (+)-phenthoate.

CAS / MDL: 7487-88-9
研究领域: 分析化学 · 环境科学 · 食品科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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PESTICIDE BIOCHEMISTRY AND PHYSIOLOGY · 2024 · IF 4.2

Identification and potential application of key insecticidal metabolites in Tilia amurensis, a low-preference host of Hyphantria cunea

Lisha Yuan,Tao Li,Yi Huang,Aoying Zhang,Shanchun Yan,Dun Jiang

Developing effective insecticidal strategies is an important means of reducing the spread and host plant damage by Hyphantria cunea . In this study, key metabolites with insecticidal activity against H. cunea were screened by targeted metabolomics in Tilia amurensis , a low-preference host plant. Subsequently, the potential of key metabolites that could be used as botanical pesticides was evaluated. The results showed that coumarin was the key insecticidal metabolite of T. amurensis and had a significant insecticidal effect and weight inhibition effect on H. cunea larvae. Coumarin treatment significantly decreased the larval nutrient content and the gene expression of rate-limiting enzymes in the glycolytic pathway and tricarboxylic acid cycle . A significantly enhanced detoxification enzyme activity (CarE and GST), antioxidant oxidase activity (SOD and CAT), non-enzymatic antioxidant levels (GSH), and total antioxidant capacity were observed in coumarin-treated larvae. Coumarin treatment resulted in a significant increase in the expression levels of detoxification enzyme genes ( CarE1 , CarE2 , CarE3 , GST2 , and GST3 ) and antioxidant oxidase genes ( SOD1 , CAT1 , and CAT2 ) in H. cunea larvae. Coumarin treatment significantly increased the levels of MDA and H 2 O 2 in larvae but did not cause pathological changes in the ultrastructure of the larval midgut. Coumarin solution sprayed directly or as a microcapsule suspension formulation with coumarin as the active ingredient had significant insecticidal activity against the H. cunea larvae. Overall, coumarin, a key anti-insect metabolite identified from T. amurensis , can significantly inhibit the growth and survival of H. cunea larvae and has the potential to be developed as a botanical pesticide.

研究领域: 植物学 · 昆虫学 · 代谢组学
✓ 已验证 DOI PubMed 高影响因子
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Insects · 2023 ·Vol. 14 ·期 12 ·959 · IF 3

Disruptive Effects of Two Curcuminoids (Demethoxycurcumin and Bisdemethoxycurcumin) on the Larval Development of Drosophila melanogaster

Jun-Hyoung Jeon,Seon-Ah Jeong,Doo-Sang Park,Hong-Hyun Park,Sang-Woon Shin,Hyun-Woo Oh

Simple SummarySeveral plant species have diterpene compounds with juvenile hormone (JH) disruptor activity in insects. Demethoxycurcumin (DMC) and bisdemethoxycurcumin (BDMC) are two curcuminoid components of turmeric, interfering with the JH-mediated formation of the JH receptor complex. In vitro, DMC and BDMC also inhibit larval and pupal development inDrosophila melanogaster. The results suggest that both DMC and BDMC are JH disruptors that affect insect growth and development by regulating JH-mediated gene expression.AbstractJuvenile hormones (JHs) play a central role in insect development, reproduction, and various physiological functions. Curcuminoids generally exhibit a wide range of biological activities, such as antioxidant, anti-inflammatory, antibacterial, and insecticidal, and they exhibit insect growth inhibitory effects. However, research on insecticidal properties of curcuminoids has been limited. Moreover, to the best of our knowledge, studies on JHs of insects and curcuminoids are lacking. Therefore, this study aimed to identify the substances that act as JH disruptors (JHDs) from edible plants. Demethoxycurcumin (DMC) and bisdemethoxycurcumin (BDMC), two curcuminoids from the turmeric plantCurcuma longaL. inhibited the formation of a methoprene-tolerant (Met)–Taiman (Tai) heterodimer complex inDrosophila melanogaster, as shown through in vitro yeast two-hybrid assays. An artificial diet containing 1% (w/v) DMC or BDMC significantly reduced the number ofD. melanogasterlarvae in a concentration-dependent manner; larval development was disrupted, preventing the progression of larvae to pupal stages, resulting in an absence of adults. Building on the results obtained in this study on curcuminoids, researchers can use our study as a reference to develop eco-friendly pesticides.Keywords:juvenile hormone;methoprene-tolerant;diterpene;juvenile hormone disruptor;curcuminoids;demethoxycurcumin;bisdemethoxycurcumin

CAS / MDL: 458-37-7 616-38-6
研究领域: 昆虫学 · 分子生物学 · 植物化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF ECONOMIC ENTOMOLOGY · 2021 ·Vol. 114 ·期 2 ·979-987 · IF 2.381

Biological Activity of trans-2-Hexenal Against the Storage Insect Pest Tribolium castaneum (Coleoptera: Tenebrionidae) and Mycotoxigenic Storage Fungi

Cui Kaidi,He Leiming,Cui Guangrui,Zhang Tao,Chen Yue,Zhang Tao,Mu Wei,Liu Feng

Grain commodities in postharvest storage often deteriorate because of fungal and insect attacks. With the green consumption requirements of consumers, ecofriendly and safe pesticides are needed for grain storage. The current study investigated the efficacy of the plant volatile compound trans-2-hexenal against the storage insect pest Tribolium castaneum (Herbst) and three commonly occurring storage fungi, viz., Fusarium graminearum, Aspergillus flavus, and Aspergillus niger, to recommend its application as a botanical fumigant for grain commodities. trans-2-Hexenal weakly repels T. castaneum but has favorable insecticidal activity against multiple developmental stages of T. castaneum, ranging in sensitivity as follows: eggs (LC50 = 14.3 µl/l) > adults (31.6 µl/l) > young larvae (42.1 µl/l) > mature larvae (64.5 µl/l) > pupae (70.5 µl/l). Moreover, trans-2-hexenal caused a high malformation rate and high mortality in adults developed from fumigated pupae. In a 7-d grain, trans-2-hexenal at 0.8 µl/ml provided an appreciable efficacy (81.3%), and concentrations ≥ 0.1 µl/ml completely inhibited the offspring of T. castaneum. trans-2-Hexenal was nonphytotoxic to the seed germination and seedling growth of wheat seeds. Furthermore, trans-2-hexenal completely inhibited the growth of A. flavus, F. graminearum, and A. niger at 5, 10, and 10 µl/l, respectively. The favorable biological activity of trans-2-hexenal against T. castaneum and three frequently occurring mycotoxigenic storage fungi indicated the potential of trans-2-hexenal for simultaneously controlling pests and pathogens, which could reduce its application frequency in grains and decrease pesticide resistance risks.

研究领域: 昆虫学 · 植物化学 · 食品科学 · 真菌学
✓ 已验证 DOI 高影响因子
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FOOD CHEMISTRY · 2020 · IF 6.306

Facile preparation of hydroxyl bearing covalent organic frameworks for analysis of phenoxy carboxylic acid pesticide residue in plant-derived food

Guiju Xu,Longfei Hou,Baoyu Li,Xiaoli Wang,Lu Liu,Na Li,Ming-Lin Wang,Ru-Song Zhao

The development of sensitive method for analysis of   pesticide residue is of great significance to ensure food safety and promote globalization of food trade. An original method was proposed for analysis of phenoxy carboxylic acids (PCAs) pesticide in plant-derived food. To concentrate trace PCAs, the TAPT-DHTA-COF was fabricated by a facile room-temperature method and utilized as the solid phase extraction cartridge packing. The TAPT-DHTA-COF exhibited excellent adsorption capacity and recyclability towards PCAs. Theoretical simulation indicated that the adsorption of PCAs onto the TAPT-DHTA-COF was driven by hydrogen bond, halogen bond and π-π interaction. Using liquid chromatography tandem mass spectrometry for detection, good linearity ranged from 0.10 to 40 ng·g −1 and low limits of detection varied from 0.007 to 0.030 ng·g −1 were achieved for PCAs in rice, apple and greengrocery. The recoveries of PCAs from the spiked samples ranged from 81.2% to 107%. The reliability was verified by the accurate determination of certified reference materials.

CAS / MDL: 631-61-8 71-36-3 95-50-1
研究领域: 食品安全 · 分析化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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PEST MANAGEMENT SCIENCE · 2025 · IF 3.8

Antimicrobial activity and mechanism of the plant-derived compound evodiamine against Phytophthora capsici

Wenhao Liang,Xiaoxiao Xu,Tong Shi,Shengyang Xu,Qizhi Wang,Bi Wang

BACKGROUND Phytophthora capsici is a devastating oomycete pathogen with major economic concern. However, the use of traditional chemical fungicides is associated with environmental pollution, and fungicide resistance is increasingly prevalent. Consequently, developing safe, effective, and environmentally friendly alternatives is critically required. Evodiamine (EVO), a bioactive alkaloid from plants, has been extensively investigated for its anti-cancer properties. However, its inhibitory effects against phytopathogens have not yet been fully elucidated. This study evaluated EVO's antimicrobial activity toward P. capsici and its potential mode of action. RESULTS EVO significantly inhibited P. capsici mycelial growth and spore germination, with median effective concentration (EC 50 ) values of 6.48 μg mL −1 and 7.13 μg mL −1 respectively, across 108 P. capsici isolates. EVO exerted its antimicrobial effects by disrupting the cellular integrity of P. capsici , specifically targeting both the cell membrane and wall. Furthermore, EVO exhibited strong protective and curative efficacies in pepper leaves and seedlings. Genome-wide transcriptional analysis revealed that EVO treatment significantly altered the gene expression profile of P. capsici , especially affecting genes relevant to cell membrane integrity and transporter activity. CONCLUSION Overall, this study revealed that EVO showed great control efficacy against P. capsici and held promise as a novel botanical fungicide. © 2025 Society of Chemical Industry.

CAS / MDL: 57837-19-1
研究领域: 植物病理学 · 农业微生物学 · 分子植物-病原互作 · 天然产物药理学 · 农药学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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FOREST PATHOLOGY · 2019 ·Vol. 49 ·期 2 ·e12467 · IF 1.434

Molecular characterization and functional analysis of daf-16-2b gene in the pine wood nematode, Bursaphelenchus xylophilus

Buyong Wang,Rongrong Wen,Ling Ma,Yan Ma,T. Hua Zhou

The Forkhead box O transcription factor DAF-16 is an important downstream transcription factor in the well-conserved insulin signalling (IIS) pathway in Caenorhabditis elegans . The nuclear localization of DAF-16 can activate a series of genes that mediate oxidative stress, heat shock, xenobiotic responses, innate immunity, metabolism and autophagy. In this study, a Bxdaf-16-2b gene encoding 510 amino acids was cloned from Bursaphelenchus xylophilus . Sequence analysis showed that the BxDAF-16-2b protein shared the highest similarity value (92%) with the DAF16-2 (accession no. ADD84716.1 ) of B. xylophilus . Using in situ hybridization, Bxdaf-16-2b was shown to be constitutively expressed in the circum-pharyngeal nerve rings and intestines of males, and in the head neurons and the ovaries of females. Quantitative RT-PCR showed that the highest gene expression was found in females, followed by juveniles, males and eggs. Bxdaf-16-2b expression was up-regulated after treatment with the botanical pesticides rotenone and matrine. RNA interference showed that the expression of Bxdaf-16-2b gene was reduced by dsRNA, and the silencing of Bxdaf-16-2b suppressed the expression of several IIS pathway genes. Bursaphelenchus xylophilus showed increased mortality at sublethal doses of rotenone and matrine when subjected to Bxdaf-16-2b gene silencing. Thus, Bxdaf-16-2b may participate in the stress response of B. xylophilus and play important roles in the immune system. This study paves the way towards design of new drug targets for non-polluting control of nematodes.

CAS / MDL: 67-68-5
研究领域: 分子生物学 · 遗传学 · 植物保护
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