Correlation between structure, retention and activity of cholic acid derived <i>cis</i>–<i>trans</i> isomeric bis‐steroidal tetraoxanes

Šegan, Sandra; Andrić, Filip; Radoičić, Aleksandra; Opsenica, Dejan; Šolaja, Bogdan A.; Zlatović, Mario; Milojković‐Opsenica, Dušanka

doi:10.1002/jssc.201100185

Cited by 19 publications

(6 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As a continuation of our previous research on chromatographic behavior of steroidal tetraoxanes [7,8] in this study the QSRR and QSAR studies of new class of mixed 1,2,4,5steroidal tetraoxanes, cholic and deoxycholic acid derivatives with observed antimalarial activity [9][10][11], were performed. The first goal of this article was to characterize the lipophilic properties of 1,2,4,5-mixed tetraoxanes and to understand the separation mechanism in a given chromatographic system by applying different methods of multivariate analysis.…”

Section: Accepted Manuscriptmentioning

confidence: 92%

Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters

Šegan

Jovanović

Milojković‐Opsenica

et al. 2014

Journal of Pharmaceutical and Biomedical Analysis

Self Cite

View full text Add to dashboard Cite

The chromatographic behavior of mixed 1,2,4,5-tetraoxanes, cholic and deoxycholic acid derivatives with distinct biological activity, was examined by high-performance thin-layer chromatography in order to correlate their structure and retention. Chromatographic systems were consisted of RP-18 or CN-silica as stationary phase, and binary mixtures of water with methanol, dioxane or acetone as mobile phase. Based on the respective retentions, the lipophilicity of the investigated compounds was determined. Multiple linear regression and partial least squares have been used to select variables that best describe the behavior of the investigated compounds in chromatographic systems and to quantify influences of most important parameters. The validation and cross-validation of the QSRR model suggest its applicability for prediction and understanding of retention of congeners. The models indicate the importance of nonpolar properties of the solutes and their ability for hydrophobic interactions, as well as the importance of proton donating abilities, hydrophilic and π interactions pointing out on that way the possible separation mechanism in the studied chromatographic systems. Observed correlations between structure and biological activity of mixed 1,2,4,5-tetraoxanes, indicate that the antimalarial activity against W2 and D6 Plasmodium falciparum strains, is governed by hydrophobic feature (measured with lipophilicity parameter), hydrophilic feature (measured with HLB, %HS, HB and HBA descriptors), and electronic feature (HOMO).

show abstract

Section: Accepted Manuscriptmentioning

confidence: 92%

Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters

Šegan

Jovanović

Milojković‐Opsenica

et al. 2014

Journal of Pharmaceutical and Biomedical Analysis

Self Cite

View full text Add to dashboard Cite

show abstract

“…Similar results could be found elsewhere in the literature. 23,24 CONCLUSIONS The present work focused on identifying the most important descriptors affecting the lipophilicity of twelve coumarin derivatives. Four commonly used descriptors for assessing the lipophilicity of unknown solutes, obtained from the thin-layer chromatographic data, were compared.…”

Section: Quantitative Structure-toxicity Relationshipmentioning

confidence: 99%

Quantitative structure-toxicity relationship study of some natural and synthetic coumarins using retention parameters

Rabtti

Natić

Milojković‐Opsenica

et al. 2012

JSCS

View full text Add to dashboard Cite

Four lipophilicity descriptors (RM0, b, C0, PC1) for twelve coumarine derivatives were determined by reversed-phase thin-layer chromatography in order to analyze which descriptor best describes the lipophilicity of coumarines investigated. Moreover, possible chemical toxicity of coumarins, expressed as the probability of a compound to cause organ-specific health effects, was calculated using ACD/Tox Suite program. The quantitative relationships between toxicity and molecular descriptors, including experimentally determined lipophilicity descriptors obtained in current study, were investigated using partial least square regression. The best models were obtained for kidney and liver health effects. Quantitative structure-toxicity relationship models revealed the importance of electric polarization descriptors, size descriptors and lipophilicity descriptors. Obtained models were used for the selection of the structural features of the compounds that are significantly affecting their absorption, distribution, metabolism, excretion, and toxicity. [Acknowledgements. This work has been supported by the Ministry of Education and Science of Serbia, Grant 172017.

show abstract

“…HCA was performed in order to confirm the grouping of compounds already obtained by the PCA. It is sometimes used to make the process of grouping similar objects in PCA score graphs easier [67]. Cluster analysis is a method for dividing a group of objects into classes so that simila objects are in the same class.…”

Section: Principal Component Analysis (Pca) and Hierarchical Cluster ...mentioning

confidence: 99%

Antioxidant Activity and Multi-Elemental Analysis of Dark Chocolate

Jaćimović

Popović‐Djordjević

Sarić

et al. 2022

Foods

View full text Add to dashboard Cite

Cocoa beans are part of the cocoa plant fruit (Theobroma cacao L.) used to prepare various products such as chocolate, cocoa butter, jelly, liqueurs, cosmetics, etc. Dark chocolate is consumed worldwide by different populations and is known for its good taste, making it one of the most favoured food products. This work aimed to determine the content of total polyphenols (TPC), total flavonoids (TFC), and the antioxidant potential measured through the ability to scavenge DPPH free radicals (DPPH), ferric reducing power (FRAP), and total antioxidant capacity (TAC), as well as major and trace elements contained in twelve commercially available dark chocolate samples, with cocoa content ranging from 40% to 99%. The total polyphenols content ranged between 10.55 and 39.82 mg/g GAE, while the total flavonoid content was from 10.04 to 37.85 mg/g CE. All applied antioxidant assays indicate that the sample with the highest cocoa percentage shows the greatest antioxidant activity (DPPH: 48.34% of inhibition; FRAP: 89.00 mg/g GAE; TAC: 83.86 mg/g AAE). Statistical methods were applied to establish the differences between the samples concerning TPC, TFC, DPPH, FRAP and TAC, as well as to differentiate the samples according to the mineral content. The results indicated that the differences in TPC and TFC between different samples depended on the cocoa content and the addition of dried fruit pieces. A good correlation between antioxidant potency composite index (ACI) and declared cocoa content was noticed (R2 = 0.8034), indicating that the declared percentage of cocoa is a reliable indicator for antioxidant activity of analysed dark chocolate samples. The nutritional evaluation proved that the studied chocolate samples were an excellent source of Mg, Fe, Mn and Cu.

show abstract

Correlation between structure, retention and activity of cholic acid derived cis–trans isomeric bis‐steroidal tetraoxanes

Cited by 19 publications

References 20 publications

Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters

Correlation study of retention data and antimalarial activity of 1,2,4,5-mixed tetraoxanes with their molecular structure descriptors and LSER parameters

Quantitative structure-toxicity relationship study of some natural and synthetic coumarins using retention parameters

Antioxidant Activity and Multi-Elemental Analysis of Dark Chocolate

Contact Info

Product

Resources

About