Molecular physicochemical parameters predicting antioxidant activity of Brazilian natural products

Scotti, Luciana; Scotti, Marcus Tullius; Pasqualoto, Kerly Fernanda Mesquita; Bolzani, Vanderlan da Silva; Ferreira, Elizabeth Igne

doi:10.1590/s0102-695x2009000600020

Cited by 15 publications

(15 citation statements)

References 19 publications

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“…Optimization of the geometry was accepted using the semi-empiric method AM 1 (Austin Model 1) [17]. The options designated in the process of the geometry optimization, like total charge and multiplicity as the follows: charge 0 and singlet for the closed shell species; charge 0 and doublet for the free radicals; charge 1 and doublet for the cationic species [18]. The SCF convergence is set to 0.0001 kcal/mol and the RMS gradient is set to 0.001 kcal/mol in the geometry optimization.…”

Section: Methodsmentioning

confidence: 99%

“…(H-L gap) parameter that guesses the hydrophobic interactions using Ghose-Pritchett-Crippen theoretical method (ClogP). Calculation of the Log P values, simulating separating of phenols in an n-octanol/water (1; 1, v/v) system, was skilled using the HyperChem-8 packet [18,20]. We have performed all the calculations by using the HyperChem-8 packet.…”

Section: Methodsmentioning

confidence: 99%

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Studies of the Relationship between Structure and Antioxidant Activity in Interesting Systems, Including Tyrosol, Hydroxytyrosol Derivatives Indicated by Quantum Chemical Calculations

Rezaei-Sadabady¹,

Zarghami²,

Barzegar³

et al. 2013

Soft

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In nature, tyrosol (TY) and hydroxytyrosol (HT) are found in olive leaves which are for medical aims, with immune stimulant and antibiotic properties as well as the ability to be used for the treatment of neurodegenerative diseases such as Alzheimer. This ability of phytochemical TY and HT compounds are mainly believed to be of higher radical scavenging potential with effective antioxidant properties. In order to establish the possible structure-antioxidant activity relationship of tyrosol, hydroxytyrosol, hydroxytyrosol acetate and two designed hydroxytyrosol derivatives were studied by the help of quantum chemical calculations. The molecular electronic properties such as heat formation of the neutral, radical and orbitals energies were calculated as descriptors to predict the H atom donating abilities of compounds. Considering the results from the calculated descriptors, the derivatives having OH group substitutions in position number four of the aromatic ring can be classified highly active and better antioxidant compound. Therefore, the designed hydroxytyrosol derivatives showed most active feasible H atom donation. This work can be useful to design novel antioxidants.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Studies of the Relationship between Structure and Antioxidant Activity in Interesting Systems, Including Tyrosol, Hydroxytyrosol Derivatives Indicated by Quantum Chemical Calculations

Rezaei-Sadabady¹,

Zarghami²,

Barzegar³

et al. 2013

Soft

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“…Also, Tasdemir et al () reported the anti‐ T. cruzi activity of chrysin dimethylether ( 153 ; IC 50 : 3.5 μg/ml; SI: 5.51, L6 cells) and 3′‐hydroxydaidzein ( 154 ; IC 50 : 4.7 μg/ml; SI: 4.53, L6 cells; Table ). Scotti, Scotti, Bolzani, and Ferreira () and Scotti, Ferreira, Silva, and Scotti () developed in silico studies to propose a pharmacophore group of many flavonoids and to know about their physicochemical properties, which could influence their biological activities.…”

Section: Natural Flavonoids As Potential Leads For the Treatment Of Mmentioning

confidence: 99%

Flavonoids as efficient scaffolds: Recent trends for malaria, leishmaniasis, Chagas disease, and dengue

Boniface

Ferreira

2019

Phytotherapy Research

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Endemic in 149 tropical and subtropical countries, neglected tropical diseases (NTDs) affect more than 1 billion people annually with over 500,000 deaths. Among the NTDs, some of the most severe consist of leishmaniasis, Chagas disease, and dengue. The impact of the combined NTDs closely rivals that of malaria. According to the World Health Organization, 216 million cases of malaria were reported in 2016 with 445,000 deaths. Current treatment options are associated with various limitations including widespread drug resistance, severe adverse effects, lengthy treatment duration, unfavorable toxicity profiles, and complicated drug administration procedures. Flavonoids are a class of compounds that has been the subject of considerable scientific interest. New developments of flavonoids have made promising advances for the potential treatment of malaria, leishmaniasis, Chagas disease, and dengue, with less toxicity, high efficacy, and improved bioavailability. This review summarizes the current standings of the use of flavonoids to treat malaria and neglected diseases such as leishmaniasis, Chagas disease, and dengue. Natural and synthetic flavonoids are leading compounds that can be used for developing antiprotozoal and antiviral agents. However, detailed studies on toxicity, pharmacokinetics, and mechanisms of action of these compounds are required to confirm the in vitro pharmacological claims of flavonoids for pharmaceutical applications. Highlights In the current review, we have tried to compile recent discoveries on natural and synthetic flavonoids as well as their implication in the treatment of malaria, leishmaniasis, Chagas disease, and dengue. A total of 373 (220 natural and 153 synthetic) flavonoids have been evaluated for antimalarial, antileishmanial, antichagasic, and antidengue activities. Most of these flavonoids showed promising results against the above diseases. Reports on molecular modeling of flavonoid compounds to the disease target indicated encouraging results. Flavonoids can be prospected as potential leads for drug development; however, more rigorously designed studies on toxicity and pharmacokinetics, as well as the quantitative structure–activity relationship studies of these compounds, need to be addressed.

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“…The antioxidant activity was evaluated and compared between the diterpenes after DFT calculations through HOMO surface and H-L GAP parameter [22] using the HyperChem 8.0 program. Docking: Molecular docking is defined as the collision of the substrate with the binding site in the correct conformation and orientation.…”

Section: Dftmentioning

confidence: 99%

Theoretical Research into Anticancer Activity of Diterpenes Isolated from the Paraiban Flora

Ishiki

Mendonça

Santos

et al. 2014

Natural Product Communications

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Many studies of the scientific literature discuss the anticancer activity of diterpenes inhibiting the Akt/IKK/NF-B pro-survival signaling cascade, mainly by the activation of serine/threonine phosphatase PP2A. The aim of this work was to evaluate and compare the anticancer potential of three atisane, three kaurane and three trachylobane diterpenes extracted from the roots of Xylopia langsdorffiana. Thus, we investigated the reactivity (H-L GAP parameter), HOMO atmosphere favorable to neutralize the radical reactivity, and the docking of compounds with PP2A. With all approaches, this theoretical study showed that atisane diterpenes have favorable characteristics for antitumor activity, like electron donating ability and greater hydrophilic interactions with the enzyme, by inhibition of Akt/IKK/NF-B, and activation of PP2A.

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Molecular physicochemical parameters predicting antioxidant activity of Brazilian natural products

Cited by 15 publications

References 19 publications

Studies of the Relationship between Structure and Antioxidant Activity in Interesting Systems, Including Tyrosol, Hydroxytyrosol Derivatives Indicated by Quantum Chemical Calculations

Studies of the Relationship between Structure and Antioxidant Activity in Interesting Systems, Including Tyrosol, Hydroxytyrosol Derivatives Indicated by Quantum Chemical Calculations

Flavonoids as efficient scaffolds: Recent trends for malaria, leishmaniasis, Chagas disease, and dengue

Theoretical Research into Anticancer Activity of Diterpenes Isolated from the Paraiban Flora

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