Dietary chromones as antioxidant agents—the structural variable

Dias, Mafalda M.; Machado, Nelson; Marques, M. P. M.

doi:10.1039/c1fo10098j

Cited by 33 publications

(29 citation statements)

References 57 publications

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“…In sum, the present work highlights the close relationship between structure and activity for hydroxylated flavone derivatives, a thorough conformational analysis being essential for attaining a better understanding of their recognised antioxidant properties (which were evaluated in a parallel study [37]). Furthermore, this detailed knowledge of the conformational behaviour of this group of phytochemicals will allow a rational design of optimised chemopreventive agents of natural origin, with improved efficacy and safety.…”

Section: Discussionmentioning

confidence: 92%

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A conformational study of hydroxyflavones by vibrational spectroscopy coupled to DFT calculations

Machado

Carvalho

Otero

et al. 2013

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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This article appeared in a journal published by Elsevier. The attached copy is furnished to the author for internal non-commercial research and education use, including for instruction at the authors institution and sharing with colleagues.Other uses, including reproduction and distribution, or selling or licensing copies, or posting to personal, institutional or third party websites are prohibited. The conformational preferences of a series of hydroxyflavones were studied by Raman and FTIR spectroscopies, coupled to Density Functional Theory calculations. Special attention was paid to the effect of hydroxyl substitution, due to its importance on the biological activity of these compounds. Their conformational preferences were found to be determined mainly by the orientation of the hydroxylic groups at C 7 and within the catechol moiety, leading to the occurrence of distinct conformers in the solid state. A complete assignment of the experimental spectra was carried out for these molecules, in the light of their most stable conformers and the corresponding predicted vibrational pattern.

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Section: Discussionmentioning

confidence: 92%

“…These will yield relevant information on the conformational preferences of the flavones, closely associated to their biological function. The results thus obtained are related to the free radical scavenging ability of the compounds, which was previously assessed by the authors [37].…”

Section: Introductionmentioning

confidence: 85%

A conformational study of hydroxyflavones by vibrational spectroscopy coupled to DFT calculations

Machado

Carvalho

Otero

et al. 2013

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…pH, temperature, ionic strength or exposure to drugs). 22,27,28 Following previous studies by the authors on dietary polyphenolic compounds -both regarding their structural and conformational preferences 17,[29][30][31][32][33][34][35][36][37][38][39][40] and their chemopreventive and/or chemotherapeutic properties towards several cancer cells -the present work reports the effect of daidzein on the biochemical profile of two human breast cancer cell lines: MCF-7 (estrogendependent, ER + ) and MDA-MB-231 (estrogen-independent, ER -). The results thus obtained are expected to help establishing an accurate balance between DAID´s antioxidant and prooxidant capacities, aiming at a prospective use against breast cancer: either as a chemopreventive agent (sole or in combination with other flavones) or as an adjuvant in chemotherapy (coupled with conventional drugs such as tamoxifen, paclitaxel, docetaxel, methotrexate, gemcitabine or doxorubicin 41,42 and cisplatin.…”

Section: A Introductionmentioning

confidence: 89%

“…1), which is expected to interact effectively with estrogen receptors therefore inhibiting estrogen synthesis 17,57,58 and leading to a growth inhibition of MCF-7 cancer cells. In turn, for the MDA-MB-231 cells lacking estrogen receptors, daidzein is suggested to affect cell proliferation and viability by interference with different metabolic pathways, namely through cell cycle arrest (changes in regulatory proteins) and induction of apoptosis (via activation of caspases).…”

Section: Mcf-7mentioning

confidence: 99%

Raman microspectroscopy for probing the impact of a dietary antioxidant on human breast cancer cells

et al. 2016

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Breast cancer is the second most common type of cancer worldwide and the most frequent among women, being the fifth cause of death from neoplastic disease. Since this is an oxidative-stress related neoplasia, it is largely preventable. A dietary isoflavone abundant in soybean -daidzein -was currently investigated as to its chemopreventive and/or chemotherapeutic properties towards the human MDA-MB-231 (metastatic, estrogen-unresponsive) and MCF-7 (estrogen-responsive) breast cancer cell lines. Biological assays for evaluation of antitumour and anti-invasive activities were combined with state-of-theart vibrational microspectroscopy techniques. At 50 and 100 µM concentrations and 48 h incubation time, daidzein was found to induce a marked decrease in cell viability (ca. 50%) for MDA-MB-231 and MCF-7 cells (respectively ca. 50% and 42%) and 40% inhibition of cell migration 48 h. MicroRaman analysis of fixed cells upon exposure to this isoflavone unveiled its metabolic impact on both cell lines. Multivariate data analysis (unsupervised PCA) led to a clear discrimination between control and DAID-exposed cells, with distinctive effects on their biochemical profile, particularly regarding DNA, lipids and protein components, in a cell-dependent way. This is the first reported study on the impact of dietary antioxidants on cancer cells by microRaman techniques. A IntroductionCancer is one of the major causes of morbidity and mortality worldwide, closely following cardiovascular disorders. Breast carcinoma, in particular, is an important public health problem since it is the second most lethal cancer among women worldwide: according to the World Health Organisation (WHO), it affects 28% of the women in Europe 1 , being the second most lethal cancer type in Portugal (16%). 2 Epidemiological evidence has demonstrated a clear difference in breast cancer incidence between eastern and western countries, asian women being the least affected, which can be closely related to dietary habits.Phytochemicals, secondary plant metabolites widespread in fruits, vegetables, cereals and beverages such as tea, coffee and wine, and very abundant in a mediterranean diet, are an abundant source of dietary antioxidants known to significantly decrease the harmful effect of oxidative species, thus being promising chemopreventive agents towards carcinogenesis. [3][4][5][6] Actually, several studies have established a direct relationship between the intake of polyphenols and the prevention of oxidative stress-induced diseases, namely neurodegenerative and cardiovascular disorders, and some types of cancer. 7,8 The isoflavone daidzein (DAID), in particular, is the second most abundant component of soybean (following genistein), a growingly consumed food product, which renders this isoflavone a very suitable target of study regarding its potential health beneficial effects. In addition, it exhibits structural and functional similarities to the endogenous hormone estrogen 9 (Fig. 1). Since some breast cancers are estrogen-dependent (ER + ), DAID may...

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“…The superoxide scavenging ability of the compound was assessed by the method of Winterbourn et al (1975) [21 ]. Principle of this assay is based on ability of superoxide ion to inhibit the reduction of nitro-blue tetrazolium (NBT) to nitroblue tetrazolium formazon and is measured spectrophotometrically at 560nm.…”

Section: Measurement Of Superoxide Scavenging Activitymentioning

confidence: 99%

QSAR, Docking and Invitro Antioxidant Activity Study of Novel Chromone Derivatives

Shanthi¹,

Ramesh²,

Srimai³

et al. 2013

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:Invitro antioxidant activity and Molecular modeling studies of nine chromone derivatives optimize their inhibitory activity against Poly [ADP correlated to different molecular properties. The AM1and PM3 semiempirical methods are used to estimate vertical ioniz tion potentials (IPv's), electron affinity (EA tion coefficient (LogP), hydration energ regression analysis are proposed. The leave final QSAR equations. The hardness (η) was found to be studies of chromone with Poly [ADP-ribose results of both QSAR and Docking studies suggested that remarkable inhibi hydrogen bond interactions along with hydrophobic and electrostatic interactions

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Dietary chromones as antioxidant agents—the structural variable

Cited by 33 publications

References 57 publications

A conformational study of hydroxyflavones by vibrational spectroscopy coupled to DFT calculations

A conformational study of hydroxyflavones by vibrational spectroscopy coupled to DFT calculations

Raman microspectroscopy for probing the impact of a dietary antioxidant on human breast cancer cells

QSAR, Docking and Invitro Antioxidant Activity Study of Novel Chromone Derivatives

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