RESUMEN
The differentiation of enantiomers is of significance in synthetic chemistry and pharmaceutical chemistry. Herein, we report a facile method for chirality sensing of monoalcohols, a challenging target due to the poor reactivity, by combining dynamic covalent chemistry with helical chirality. Four diphenylethene (DPE) derived cyclic hemiaminals were constructed, and the incorporation of a broad range of alcohols and thiols with high efficiency was achieved. The reversibility was further verified by dynamic component exchange. The helical chirality of the DPE motif was induced through chirality transfer by the central chirality of the analytes, resulting in circular dichroism responses. The chirality differentiation of seven chiral secondary alcohols including both alkyl and aryl alcohols was realized, further allowing the quantification of enantiomeric excess with high accuracy. The results described should lay a foundation for future endeavors in chemical sensing, asymmetric synthesis, and chiroptical materials.
RESUMEN
Sour rot is a leading disease of citrus fruit caused by the postharvest pathogen Geotrichum citri-aurantii. It has been reported that essential oils can be used as substitutes for synthetic fungicides to control the pathogen. In this study, changes in metabolites and antifungal effects of G. citri-aurantii treated with peppermint oil (PO) were investigated. The inhibition rate of the mycelial growth increased as the PO concentration increased, and 6 µl PO/disk resulted in a radial growth inhibition of 79.2%. The electrical conductivity of G. citri-aurantii treated with PO increased compared to the control. By comparing the metabolic profiles of treated and untreated G. citri-aurantii cells, a total of 53 distinct metabolites 9 were up-regulated and 44 were down-regulated were found, including 16 lipid metabolites, 6 carbohydrate metabolites, 2 amino acid metabolites, 5 alcohols, 2 glycoside metabolites, and 3 ketone metabolites, etc, and these metabolites are involved in 25 major metabolic pathways. PRACTICAL APPLICATIONS: Chemical fungicides can effectively control G. citri-aurantii during fruit postharvest period. However, synthetic chemical fungicides have gradually led to buildup of resistance of fungil, which seriously causes the frequent of food-borne diseases. PO extracted from natural plants can be used as natural additive in many foods due to their antioxidant, antibacterial, and antifungal properties. Therefore, PO can be considered as a promising bacteriostatic agent for the defense of G. citri-aurantii during fruit postharvest period.
Asunto(s)
Proteínas Fúngicas/genética , Fungicidas Industriales/farmacología , Geotrichum/química , Geotrichum/efectos de los fármacos , Aceites de Plantas/farmacología , Cromatografía Líquida de Alta Presión , Citrus/microbiología , Proteínas Fúngicas/metabolismo , Cromatografía de Gases y Espectrometría de Masas , Regulación Fúngica de la Expresión Génica/efectos de los fármacos , Geotrichum/genética , Geotrichum/metabolismo , Mentha piperita , Enfermedades de las Plantas/microbiología , Enfermedades de las Plantas/prevención & controlRESUMEN
Resveratrol dimers belong to a group of compounds called stilbenes, which along with proanthocyanidins, anthocyanins, catechins, and flavonols are natural phenolic compounds found in grapes and red wine. Stilbenes have a variety of structural isomers, all of which exhibit various biological properties. Counter-current chromatography with a two-phase solvent system composed of n-hexane/ethyl acetate/methanol/water (2:5:4:5, v/v/v/v) was applied to isolate and purify stilbene from the stems of wine grape. Two isomers of resveratrol dimers trans-ε-viniferin and trans-δ-viniferin were obtained from the crude sample in a one-step separation, with purities of 93.2 and 97.5%, respectively, as determined by high-performance liquid chromatography. The structures of these two compounds were identified by (1) H and (13) C NMR spectroscopy. In addition, their antioxidant activities were assessed by 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The antioxidant activities of trans-δ-viniferin were higher than that of trans-ε-viniferin in this model. This work demonstrated that counter-current chromatography is a powerful and effective method for the isolation and purification of polyphenols from wine grape. Additionally, the DPPH radical assay showed that the isolated component trans-δ-viniferin exhibited stronger antioxidant activities than trans-ε-viniferin and a little bit weaker than vitamin E at the same concentration.
