Similarities on the mode of action of the terpenoids citral and farnesene in Arabidopsis seedlings involve interactions with DNA binding proteins
David López-GonzálezElisa GrañaMarta TeijeiraMercedes VerdeguerManuel J. ReigosaAdela M. Sánchez‐MoreirasFabrizio Araniti
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The sesquiterpene farnesene and the monoterpene citral are phytotoxic natural compounds characterized by a high similarity in macroscopic effects, suggesting an equal or similar mechanism of action when assayed at IC50 concentration. In the present study, a short-time experiment (24 and 48 h) using an imaging spectrofluorometer allowed us to monitor the in-vivo effects of the two molecules, highlighting that both terpenoids were similarly affecting all PSII parameters, even when the effects of citral were quicker in appearing than those of farnesene. The multivariate, univariate, and pathway analyses, carried out on untargeted-metabolomic data, confirmed a clear separation of the plant metabolome in response to the two treatments, whereas similarity in the affected pathways was observed. The main metabolites affected were amino acids and polyamine, which significantly accumulated in response to both treatments. On the contrary, a reduction in sugar content (i.e. glucose and sucrose) was observed. Finally, the in-silico studies demonstrated a similar mechanism of action for both molecules by interacting with DNA binding proteins, although differences concerning the affinity with the proteins with which they could potentially interact were also highlighted. Despite the similarities in macroscopic effects of these two molecules, the metabolomic and in-silico data suggest that both terpenoids share a similar but not equal mechanism of action and that the similar effects observed on the photosynthetic machinery are more imputable to a side effect of molecules-induced oxidative stress.Keywords:
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This is a short review on the mechanism of action of high-affinity antiestrogens at the cellular and molecular level. Past and recent data from this and other laboratories are discussed concerning the mode of action of antiestrogens in controlling gene expression and cell proliferation, including their mode of action as inhibitors of growth factor action and oncogene expression. It has been proposed that antiestrogens may not simply act to inhibit estrogen action but may also directly trigger cell growth inhibition via the estrogen receptor in the absence of estrogen. "Estrogen receptor mediated growth inhibitors" may therefore be a more appropriate and general term for defining these estrogen analogues.
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Despite forty years of research on the potential role of chromium in carbohydrate and lipid metabolism, significant progress has only recently been made regarding the mode of action of chromium at a molecular level. The oligopeptide low-molecular-weight chromium-binding substance (LMWCr) may function as part of a novel insulin-signaling autoamplification mechanism. The proposed mechanism of action also sheds some light on the potential of chromium-containing compounds as nutritional supplements or in the treatment of adult-onset diabetes and other conditions. The potential relationship between the results of recent studies on diabetic patients and the proposed mode of action of LMWCr are discussed.
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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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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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