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FOOD CHEMISTRY · 2022 · IF 9.231

Characterization of a new (Z)-3:(E)-2-hexenal isomerase from tea (Camellia sinensis) involved in the conversion of (Z)-3-hexenal to (E)-2-hexenal

Cong Chen,Fei Yu,Xinli Wen,Shuna Chen,Kaixi Wang,Feiquan Wang,Jianming Zhang,Yuanyuan Wu,Puming He,Youying Tu,Bo Li

Two major green leaf volatiles (GLVs) in tea that contribute greatly to tea aroma, particularly the green odor, are (E)-2-hexenal and (Z)-3-hexenal. Until now, their formation and related mechanisms during tea manufacture have remained unclear. Our data showed that the contents of (E)-2-hexenal and (Z)-3-hexenal increased more than 1000-fold after live tea leaves were torn. Subsequently, a new (Z)-3:(E)-2-hexenal isomerase (CsHI) was identified in Camellia sinensis . CsHI irreversibly catalyzed the conversion of (Z)-3-hexenal to (E)-2-hexenal . Abiotic stresses including low temperature, dehydration, and mechanical wounding, did not influence the (E)-2-hexenal content in intact tea leaves during withering, but regulated the proportions of (Z)-3-hexenal and (E)-2-hexenal in torn leaves by modulating CsHI at the transcript level. For the first time, this work reveals the formation of (E)-2-hexenal during tea processing and suggests that CsHI may play a pivotal role in tea flavor development as well as in plant defense against abiotic stresses.

研究领域: 植物学 · 食品科学 · 分子生物学
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2022 · IF 6.056

(E)-2-Hexenal-based coating induced acquired resistance in apple and its antifungal effects against Penicillium expansum

Xianghua Wang,Maorun Fu,Xiaoqian Qu,Jingjing Liu,Jianwen Bu,Shaoran Feng,Handong Zhao,Wenxiao Jiao,Fei Sun

(E)-2-Hexenal is one of the most prevalent and abundant volatile substances in fruits. Many researchers have attempted fumigation with (E)-2-hexenal to control fungal diseases with poor or no results; the key is the inability to maintain an effective concentration for a long time. Therefore, a new starch-based antifungal coating with (E)-2-hexenal microcapsules was prepared. The obtained results showed that the microcapsule embedding rate reached 78.95% by orthogonal optimization experiments and that the (E)-2-hexenal-based coating was effective at reducing the lesion diameter of apple fruit during storage at 25 °C after Penicillium expansum infection, and in other fruits; it also achieved a good antifungal effect. Moreover, the activities of the main defense-related enzymes and the expression of key genes involved in the salicylic acid (SA) signaling pathway, such as CHI, GLU, PAL , NPR1 , and PR1 , were enhanced by (E)-2-hexenal-based coating treatment. These findings suggest that the (E)-2-hexenal-based coating has the dual effect of direct antifungal and induction of apple system resistance. E2H-based coating is a promising approach to control postharvest Penicillium expansum in fruit.

CAS / MDL: 7732-18-5
研究领域: 植物病理学 · 食品科学 · 分子生物学
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SCIENTIA HORTICULTURAE · 2023 · IF 4.3

(E)-2-hexenal regulates the chloroplast degradation in tomatoes

Xiaoqian Qu,Xince Wang,Maorun Fu,Jianfeng Cheng,Jingjing Liu,Xianghua Wang,Jia Li,Jinjin Wang,Ziqi Wang,Fei Sun

The concentrations of (E) -2-hexenal (E2H) have obvious correlation with the color change process in tomatoes during ripening. It is proposed that E2H may play a role in regulating the chloroplast degradation. In this study, the exogenous E2H was applied to tomato fruits and plants to create a higher concentration of E2H atmosphere than naturel released. A set of indices in response to E2H were detected. The color change was inhibited. The ethylene pathway and the involved genes were limited. The results of subcellular structure changes, the fatty acid profiles and the malondialdehyde (MDA) content supported that the chloroplast membranes were specifically degraded. The hydroperoxide lyase (HPL) and the lipoxygenase (LOX) pathway was activated to decompose the free fatty acids. In tomato plants at the harvest stage, E2H did not affect the ripe tomatoes, but inhibited the color changes of green tomatoes, accelerated the withering of the leaves and the branches, and made the fruits fall off easier. The chlorophagy was activated and the autophagosomes were observed to decompose the chloroplasts in leaves. In conclusion, E2H accelerated the chloroplast degradation, by which the color changes were regulated.

CAS / MDL: 7732-18-5
研究领域: 植物学 · 分子生物学
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INTERNATIONAL JOURNAL OF FOOD MICROBIOLOGY · 2022 · IF 5.911

Natural food flavour (E)-2-hexenal, a potential antifungal agent, induces mitochondria-mediated apoptosis in Aspergillus flavus conidia via a ROS-dependent pathway

Weibin Ma,Luling Zhao,Eric T. Johnson,Yanli Xie,Mingming Zhang

Natural food flavour ( E )-2-hexenal, a green leaf volatile, exhibits potent antifungal activity on Aspergillus flavus , but its antifungal mechanism has not been fully elucidated. In this study, we evaluated ( E )-2-hexenal-induced apoptosis in A. flavus conidia and explored the underlying mechanisms of action. Evidence of apoptosis in A. flavus conidia were investigated by methods including fluorescent staining, flow cytometry, confocal laser scanning microscope, and spectral analysis. Results indicated that 4.0 μL/mL (minimum fungicidal concentration, MFC) of ( E )-2-hexenal application induced early markers of apoptotic cell death in A. flavus conidia with a rate of 38.4% after 6 h exposure. Meanwhile, typical hallmarks of apoptosis, such as decreased mitochondrial membrane potential (MMP), activated metacaspase activity, fragmented DNA, mitochondrial permeability transition pore (MPTP) opening and cytochrome c (Cyt C) release from mitochondria to the cytosol were also confirmed. Furthermore, intracellular ATP levels were reduced by 63.3 ± 3.6% and reactive oxygen species (ROS) positive cells increased by 31.1 ± 3.1% during A. flavus apoptosis induced by ( E )-2-hexenal. l -Cysteine (Cys), an antioxidant, could strongly block the excess ROS generation caused by ( E )-2-hexenal, which correspondingly resulted in a significant inhibition of MPTP opening and decrease of apoptosis in A. flavus , indicating that ROS palys a pivotal role in ( E )-2-hexenal-induced apoptosis. These results suggest that ( E )-2-hexenal exerts its antifungal effect on A. flavus conidia via a ROS-dependent mitochondrial apoptotic pathway.

CAS / MDL: 6728-26-3
研究领域: 微生物学 · 药理学 · 食品科学
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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2025 · IF 8.5

(E)-2-Hexenal-loaded ethyl cellulose/agarose aerogel: Preparation, characterization and application in fresh rice noodles preservation

Haiyan Li,Zekun Jin,Nengguo Tao

This study aimed to develop food-grade ethyl cellulose/agarose aerogels for the controlled release of plant essential oils to extend the shelf life of fresh rice noodles. The antibacterial efficacy of ten unsaturated aldehyde essential oils was evaluated against primary spoilage bacteria, including Leuconostoc lactis , Lactococcus lactis , Acinetobacter johnsonii , Exiguobacterium indicum , and Enterobacter sichuanensis . Based on its superior antimicrobial performance, (E)-2-hexenal was selected for encapsulation within ethyl cellulose/agarose aerogels to achieve controlled release and extend the shelf life of fresh rice noodles. Increasing the ethyl cellulose concentration resulted in a more uniform pore size distribution, enhanced mechanical properties and hydrophobicity, and improved controlled release of (E)-2-hexenal in the aerogels. The optimized aerogel, loaded with 0.20 μL/mL of (E)-2-hexenal, exhibited significant antimicrobial activity, effectively inhibiting bacterial growth for 72 h. Moreover, the aerogel formulation effectively preserved the quality of fresh rice noodles by mitigating changes in total plate count, pH, water content, water activity, cooking properties, color, and texture, ultimately extending the product's shelf life by 4 days at 25 °C. These findings highlight the potential of ethyl cellulose/agarose aerogels loaded with (E)-2-hexenal as an innovative preservation strategy for fresh rice noodles, providing a promising method for enhancing food quality and longevity.

研究领域: 食品科学 · 微生物学
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JOURNAL OF COLLOID AND INTERFACE SCIENCE · 2024 · IF 9.4

Portable hydrogel kit based on Michael addition reaction for (E)-2-hexenal gas detection

Ziyu Gan,Jun Wang

Plants exhibit rapid responses to biotic and abiotic stresses by releasing a range of volatile organic compounds (VOCs). Monitoring changes in these VOCs holds the potential for the early detection of plant diseases. This study proposes a method for identifying late blight in potatoes based on the detection of (E) -2-hexenal, one of the major VOC markers released during plant infection by Phytophthora infestans . By combining the Michael addition reaction with cysteine-mediated etching of aggregation-induced emission gold nanoclusters (Au NCs), we have developed a portable hydrogel kit for on-site detection of (E) -2-hexenal. The Michael addition reaction between (E) -2-hexenal and cysteine effectively alleviates the etching of cysteine-mediated Au NCs, leading to a distinct fluorescence color change in the Au NCs, enabling a detection limit of 0.61 ppm. Utilizing the superior loading and diffusion characteristics of the three-dimensional structure of agarose hydrogel, our sensor demonstrated exceptional performance in terms of sensitivity, selectivity, reaction time, and ease of use. Moreover, quantitative measurement of (E) -2-hexenal was made easier by using ImageJ software to transform fluorescent images from the hydrogel kit into digital data. Such method was effectively used for the early detection of potato late blight. This study presents a low-cost, portable fluorescent analytical tool, offering a new avenue for on-site detection of plant diseases.

研究领域: 植物病理学 · 分析化学
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JOURNAL OF PEST SCIENCE · 2020 ·Vol. 94 ·期 2 ·463-472 · IF 4.578

Chemical polymorphism regulates the attractiveness to nymphs in the bean bug Riptortus pedestris

Xu Hao,Zhao Jiajia,Li Faqian,Yan Qi,Meng Ling,Li Baoping

Riptortus pedestris (Fab.) is an important pest on soybean plants in East Asia. Females lay eggs scattered not only on host plants, but also on non-host plants, probably for avoiding detection by natural enemies. Newly hatched nymphs can develop to the second instar without the need of food except water. Second instar nymphs, the first-feeding stage with a strong locomotion, need to find suitable feeding sites on host plants. The mechanism is still not well understood. Here, we found second instars were attracted by both male and female adults, but generally repelled by second and fifth instar nymphs, wherein their responses were little affected by food volatiles (soybean seeds or seedlings). Nymphs distinctly differed from adults in chemical composition of the whole-body extracts. 4-oxo-( E )-2-Hexenal was the major component in nymph’s extracts, but it was not found in adults, whereas some ester compounds, such as ( E )-2-hexenyl esters, were exclusively found in adults and accounted for the main part in their extracts. The three esters, ( E )-2-hexenyl ( Z )-3-hexenoate (E2-6:Z3Hx), ( E )-2-hexenyl ( E )-2-hexenoate (E2-6:E2Hx) and myristyl isobutyrate, were male specific and had been reported as an aggregation pheromone. Synthetic 4-oxo-( E )-2-hexenal strongly repelled second instars, while ( E )-2-hexenyl hexanoate emitted by both males and females attracted them. The main component of the aggregation pheromone, myristyl isobutyrate, also strongly attracted second instars. How the findings may improve the efficiency of chemical traps in fields was discussed.

研究领域: 昆虫学 · 化学生态学 · 害虫管理
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Plants-Basel · 2024 ·Vol. 13 ·期 2 ·317 · IF 4

Allelopathy and Identification of Volatile Components from the Roots and Aerial Parts of Astragalus mongholicus Bunge

Xiu Wang,Yaqi Liu,Na Peng,Haitao Yu,Yu Ma,Mingxin Zhang,Yaoyao Wang,Yi Wang,Weiwei Gao

The volatile compounds produced by plants play an important role in plant growth, plant communication, and resistance to biological and abiotic stresses.Astragalus membranaceusvar.mongholicus(AM) is a perennial herbaceous plant (Leguminosae) that is widely cultivated in northwest China. The bioactive compounds in its root have shown various pharmacological activities. Root rot disease caused byFusariumspp. often occurs inAMplanting with increasing severity in continuous monoculture. It is currently still unclear what are the effects of the volatile compounds produced by freshAMon itself, other crops cultivated on the same field afterAM, pathogen, and rhizobia. In this study, we found that seed germination and seedling growth ofAM, lettuce (Lactuca sativaL.), and wheat (Triticum aestivumL.) could be affected if they were in an enclosed space with freshAMtissue. Additionally, 90 volatile compounds were identified by SPME-GC-MS from wholeAMplant during the vegetative growth, 36 of which were specific to aerial parts ofAM(stems and leaves, AMA), 17 to roots (AMR), and 37 were found in both AMA and AMR. To further identify the allelopathic effects of these volatile compounds, five compounds (1-hexanol, (E)-2-hexenal, (E,E)-2,4-decadienal, hexanal, and eugenol) with relatively high content inAMwere tested on three receptor plants and two microorganisms. We found that (E,E)-2,4-decadienal and (E)-2-hexenal showed significant inhibitory effects on the growth ofAMand lettuce. One-hexanol and hexanal suppressed the growth of wheat, while eugenol showed a similar effect on all three plant species. Moreover, the activities of these compounds were dose dependent. Notably, we discovered that (E)-2-hexenal and eugenol also inhibited the growth of the pathogenFusarium solaniby as high as 100%. Meanwhile, all five compounds tested suppressed the rhizobiaSinorhizobium fredii. In summary, this study furthered our understanding of the comprehensive allelopathic effects of the main volatile components ofAM.

研究领域: 植物科学 · 药理学 · 微生物学 · 农业科学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2019 · IF 3.571

(E)-2-Hexenal, as a Potential Natural Antifungal Compound, Inhibits Aspergillus flavus Spore Germination by Disrupting Mitochondrial Energy Metabolism

Weibin Ma,Luling Zhao,Wenhong Zhao,Yanli Xie

Fungal contamination imposes threats to agriculture and food production and human health. A method to safely and effectively restrict fungal contamination is still needed. Here, we report the effect and mode of action of (E)-2-hexenal, one of the green leaf volatiles (GLVs), on the spore germination of Aspergillus flavus, which can contaminate a variety of crops. The EC50 value, minimum inhibitory concentration (MIC), and minimum fungicidal concentration (MFC) of (E)-2-hexenal were 0.26, 1.0, and 4.0 μL/mL, respectively. As observed by scanning electron microscopy (SEM), the surface morphology of A. flavus spores did not change after treatment with the MIC of (E)-2-hexenal, but the spores were shrunken and depressed upon treatment with the MFC of (E)-2-hexenal. The MIC and MFC of (E)-2-hexenal induced evident phosphatidylserine (PS) externalization of A. flavus spores as detected by double staining with Annexin V-FITC and propidium iodide, indicating that early apoptosis was potentially induced. Furthermore, sublethal doses of (E)-2-hexenal disturbed pyruvate metabolism and reduced the intracellular soluble protein content of A. flavus spores during the early stage of germination, and MIC treatment decreased acetyl-CoA and ATP contents by 65.7 ± 3.7% and 53.9 ± 4.0% (P < 0.05), respectively. Additionally, the activity of mitochondrial dehydrogenases was dramatically inhibited by 23.8 ± 2.2% (P < 0.05) at the MIC of (E)-2-hexenal. Therefore, the disruption of mitochondrial energy metabolism and the induction of early apoptosis are involved in the mechanism of action of (E)-2-hexenal against A. flavus spore germination.

CAS / MDL: 6728-26-3
研究领域: 微生物学 · 植物科学 · 药理学 · 真菌学
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EUROPEAN FOOD RESEARCH AND TECHNOLOGY · 2016 ·Vol. 243 ·期 2 ·203-214 · IF 1.433

Comparison of the nutritional as well as the volatile composition of in-season and off-season Hezuo 903 tomato at red stage

Liu Tao,Zhu Wei,Huang Jing,Chen Huahan,Nie Rongzu,Li Chun-mei

The influence of the planting season on the nutritional as well as the aromatic composition of Hezuo 903 tomato was investigated by combining use of nutrition analysis, sensory evaluation, electronic nose and electronic tongue analysis, gas chromatography–mass spectrometry (GC–MS) and GC–MS–olfactometry (GC–MS–O) method. The results suggested that in-season tomato contained higher levels of reducing sugar, vitamin C and lycopene than off-season tomato. In-season tomato showed a better overall flavor and acceptability than off-season tomato. Significant difference was observed in both composition and concentration of the typical volatile and aroma-active compounds in two samples. E-2-Hexenal and methyl salicylate were only found in off-season tomato, and phenylacetaldehyde detected merely in in-season tomato. In addition, significantly higher levels of 6-methyl-5-hepten-2-one ( P  < 0.01) and 2-isobutylthiazole ( P  < 0.01) were detected in off-season tomato than in-season tomato, which showed a negative effect on the overall flavor of tomato. Our result indicated that the planting season affected the composition and concentration of both non-volatile and volatile compounds of tomato fruit.

CAS / MDL: 108-94-1 109-66-0
研究领域: 农业 · 食品科学 · 营养学 · 植物生理学
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FOOD RESEARCH INTERNATIONAL · 2018 · IF 3.52

Variation of aroma profile in fermentation process of Wuliangye baobaoqu starter

Jia Zheng,Dong Zhao,Zhifu Peng,Kangzhuo Yang,Qiang Zhang,Yongkui Zhang

Changes of volatile compounds and sensory properties in the fermentation process of Wuliangye baobaoqu starter (WBS) were determined by sensory analysis, gas chromatography-olfactometry (GC/O) and GC quantitative analyses. The sensory properties of WBS changed from the sour, fruity, bready notes at the temperature-rise phase (3-day and 7-day) to the nutty and moldy notes at the temperature-fall phase (18-day, 21-day and 27-day). Acetic acid, methional, ethyl acetate, phenylethyl alcohol, ethyl 2-phenylacetate, 4-vinylguaiacol were potential aroma active compounds based on their Osme values. Results of GC quantitative analyses showed that the acids had the highest concentration. The concentration of ( E )-2-hexenal, ethyl acetate, isoamyl alcohol, phenylethyl alcohol, 2- n -pentylfuran, acetic acid and lactic acid increased with the fermentation time, presented the highest level in the temperature-rise phase and decreased after this period. The concentration of ( E,E )-2,4-hexadienal, 2,6-dimethylpyrazine, trimethylpyrazine, tetramethylpyrazine presented the highest level at the temperature-fall phase. Ethyl 3-methylbutanoate, ( E , E )-2,4-hexadienal, ( E , E )-2,4-nonadienal, acetic acid and butanoic acid had high odor active values. Results of principal component analysis showed that acetic acid, hexanal, ( E )-2-hexenal, lactic acid, isoamyl alcohol, 1-hexanol and 1-octen-3-ol were critical volatile chemicals to distinguish different WBS samples.

研究领域: 食品科学 · 分析化学 · 感官科学
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