Transcriptome and binding data indicate that citral inhibits single strand DNA‐binding proteins
Elisa GrañaCarla Díaz‐TielasAdela M. Sánchez‐MoreirasManuel J. ReigosaMaría CeleiroRuben AbagyanMarta TeijeiraMary V. DukeTracy ClerkZhiqiang PanStephen O. Duke
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The mechanism of phytotoxicity of citral was probed in Arabidopsis thaliana using RNA-Seq and in silico binding analyses. Inhibition of growth by 50% by citral downregulated transcription of 9156 and 5541 genes in roots and shoots, respectively, after 1 h. Only 56 and 62 genes in roots and shoots, respectively, were upregulated. In the shoots, the downregulation increased at 3 h (6239 genes downregulated, vs 66 upregulated). Of all genes affected in roots at 1 h (time of greatest effect), 7.69% of affected genes were for nucleic acid binding functions. Genes for single strand DNA binding proteins (SSBP) WHY1, WHY 2 and WHY3 were strongly downregulated in the shoot up until 12 h after citral exposure. Effects were strong in the root at just 1 h after the treatment and then at 12 and 24 h. Similar effects occurred with the transcription factors MYC-2, ANAC and SCR-SHR, which were also significantly downregulated for the first hour of treatment, and downregulation occurred again after 12 and 24 h treatment. Downregulation of ANAC in the first hour of treatment was significantly (P < 0.0001) decreased more than eight times compared to the control. In silico molecular docking analysis suggests binding of citral isomers to the SSBPs WHY1, WHY2, and WHY3, as well as with other transcription factors such as MYC-2, ANAC and SCR-SHR. Such effects could account for the profound and unusual effects of citral on downregulation of gene transcription.Keywords:
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Inclusion of the two isomers of citral (E-citral and Z-citral), components of lemongrass oil, was investigated within the confines of various cyclodextrin (α-CD, β-CD and γ-CD) host molecules. Aqueous complex formation constants for E-citral with α-CD, β-CD and γ-CD were determined to be 123, 185, and 204 L/mol, respectively, whereas Z-citral exhibited stronger affinities (157, 206, and 253 L/mol, respectively). The binding trend γ-CD > β-CD > α-CD is a reflection of the more favorable geometrical accommodation of the citral isomers with increasing cavity size. Encapsulation of lemongrass oil within CDs was undertaken through shaking citral:CD (1:1, 1.5:1, and 2:1 molar ratio) mixtures followed by spray drying. Maximum citral retention occurred at a 1:1 molar ratio with β-CD and α-CD demonstrating the highest levels of total E-citral and Z-citral retention, respectively. Furthermore, the β-CD complex demonstrated the slowest release rate of all inclusion complex powders.
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14C-labelled citral was applied on four groups of guinea pigs: (a) one sensitized to citral alone; (b) one sensitized to a citral-d-limonene 1 : 1 molar mixture; (c) FCA-treated controls; (d) controls. The most important results concern the amount of labelled material in soluble compared with insoluble skin protein extracts (SPE). In citral-sensitized animals, more label was found in the soluble SPE when citral + limonene was applied to the skin; in citral + limonene sensitized animals, the same trend (i.e. more label in soluble SPE) was found. The possible role of limonene in alleviating the allergic reaction to citral is discussed.
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Carvone
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Abstract Citral forms an important constituent of many essential oils. It is present in a large number of essential oils containing lemon perfume and is of great commercial value. Methods of estimation of citral, available in literature are not very accurate or time consuming. The method developed by the author is based on colour change reaction of citral with rhodium (III). If all necessary requirements for experiment are ready, the estimation of citral occures within ten minutes. Rhodium (III) can also be determined with its colour change reaction by citral.
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The importance of yeast old yellow enzymes is increasingly recognized for direct asymmetric reduction of (E/Z)-citral to (R)-citronellal. As one of the most performing old yellow enzymes, the enzyme OYE3 from Saccharomyces cerevisiae S288C exhibited complementary enantioselectivity for the reduction of (E)-citral and (Z)-citral, resulting in lower e.e. value of (R)-citronellal in the reduction of (E/Z)-citral. To develop a novel approach for the direct synthesis of enantio-pure (R)-citronellal from the reduction of (E/Z)-citral, the enzyme OYE3 was firstly modified by semi-rational design to improve its (R)-enantioselectivity. The OYE3 variants W116A and S296F showed strict (R)-enantioselectivity in the reduction of (E)-citral, and significantly reversed the (S)-enantioselectivity in the reduction of (Z)-citral. Next, the double substitution of OYE3 led to the unique variant S296F/W116G, which exhibited strict (R)-enantioselectivity in the reduction of (E)-citral and (E/Z)-citral, but was not active on (Z)-citral. Relying on its capability discriminating (E)-citral and (Z)-citral, a new cascade reaction catalyzed by the OYE3 variant S296F/W116G and glucose dehydrogenase was developed, providing the enantio-pure (R)-citronellal and the retained (Z)-citral after complete reduction of (E)-citral.
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The application of essential oils in form of nanoemulsions has been proposed as a method to improve their solubility in aqueous solutions, and hence their antimicrobial activity. The objective of this study was to evaluate the antimicrobial activity of citral, applied directly or in combined treatments with heat or pulsed electric fields (PEF), as a function of the inoculation procedure assayed: (i) a simple, vigorous shaking method by vortex agitation (suspension of citral; s-citral) or (ii) the previous preparation of nanoemulsions by the emulsion phase inversion (EPI) method (nanoemulsion of citral; n-citral). n-Citral was more effective in either inhibiting or inactivating Escherichia coli O157:H7 Sakai than s-citral. However, when combined with heat, a greater synergistic effect was observed with s-citral rather than with n-citral, either in lab media (pH 7·0 and 4·0) or apple juice. For instance, while almost 5 log10 cell cycles were inactivated in apple juice after 15 min at 53°C in the presence of 0·1 μl ml-1 of s-citral, the use of n-citral required 30 min. The use of nanoemulsions did not modify the slight synergism observed when citral and mild PEF were combined (150 μs, 30 kV cm-1 ).The exploration of different delivery systems of antimicrobial compounds such as citral in aqueous food products aids in the establishment of successful combined treatments for food preservation. While at room temperature, citral in form of a nanoemulsion shows a higher antimicrobial activity; its combination with heat would imply a partial loss of the outstanding synergistic lethal effect achieved when added in suspension form. Therefore, the most suitable procedure to magnify the synergism between heat and citral when processing juices would merely require an intense homogenization step prior to the combined treatment.
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At present the usual method of estimation of citral in lemon grass (C i m b 0 p o g e n f l e x u o s u s) oil is by sodium bisulphite adducting. However this method cannot be expected to give correct val ue since other aldehydes and methyl ketones, known to be present in lemon grass oil will also get adducted. A new method of estimation for citral is now developed which avoids this defect, by physically separ ating citral quantitatively in pure form from lemon grass oil samples by colum chromatography. This method yields very reliable results, since the citral present is physically isolated quantitively from the oil in pure form. The above method involving the use of no chemical, can also be adopted as an excellent method, superior to all the other methods known for the isolation of pure citral. Hence this method can be of commerical value for the production of pure citral.
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Abstract Citral is a lemon scented acyclic monoterpene aldehyde consists of a racemic mixture of two isomers geranial (trans-citral or citral A) and neral (cis-citral or citral B). It is most important component of essential oils of Cymbopogon species mainly, East Indian (Cymbopogon flexuosus) and West Indian (C. citratus) lemongrass. It is also present as major component in other plant species particularly, citrus fruits. Citral imparts a characteristic lemon like aroma to the essential oils of lemongrass. Citral possesses many significant bioactivities such as, antimicrobial, anti-inflammatory, antiparasitic, allelopathic and mosquito repellent. Citral is most valuable monoterpene in flavors, fragrances, cosmetics, perfumery and pharmaceuticals. It is used for the synthesis of vitamin A and β-ionones and other specialty chemicals. A growing number of reports published on bioactivities of citral and citral rich essential oils have reflected their rapidly increasing medicinal and pharmacological significance. In the present work, we have reviewed reports published recently on bioactivities of citral, citral derivatives and essential oils rich in citral content.
Citral
Cymbopogon citratus
Monoterpene
Citronellal
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Abstract BACKGROUND Citral is one of the most important flavor compounds in fresh juice and lemon oil. Unfortunately, citral is chemically unstable and degrades over time in aqueous solutions. Here, citral nanoemulsions including a mixture of gelatin and Tween 20 as emulsifiers were produced in an effort to maintain the stability of citral in an acidic system. RESULTS The mean droplet size and polydispersity index of the citral nanoemulsion were 467.83 nm and 0.259 respectively when the mass ratio of gelatin/Tween 20 was 3:1 and the total emulsifier concentration of the emulsion system was 10 g kg −1 . The citral nanoemulsion remained stable during storage for 14 days at 30 °C. Therefore this nanoemulsion system effectively protected citral from degradation and decreased the formation of off‐flavor compounds (e.g. p ‐cymene, p ‐cresol and p ‐methylacetophenone) relative to a single emulsifier. CONCLUSION The mixture of gelatin and Tween 20 enhanced the stability of citral under acidic conditions and could be used as an effective emulsifier to protect citral from degradation under acidic environments in the food industry. © 2016 Society of Chemical Industry
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Gelatin
Genipin
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Nerol
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Citral showed appreciable antimicrobial activity against Gram‐positive and Gram‐negative bacteria as well as fungi. Media composition and inoculum size had no observable effect on activity but alkaline pH increased citral activity. The growth rates of Escherichia coli cultures were reduced at concentrations of citral ≥0·01% v/v while concentrations ≥0·03% v/v produced rapid reduction in viable cells followed by limited regrowth. In a non‐growth medium, 0·08% and 0·1% v/v showed rapid bactericidal effects. Citral may therefore be of preservative use in addition to its other uses in the food, soap and cosmetic industries.
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