Lipophilicity of some guaianolides isolated from two endemic subspecies of <i>Amphoricarpos neumayeri</i> (Asteraceae) from Montenegro

Atrrog, Abubaker A. B.; Natić, Maja; Tosti, Tomislav; Milojković‐Opsenica, Dušanka; Ðorđević, Iris; Tešević, Vele; Jadranin, Milka; Milosavljević, Slobodan; Lazić, Milan; Radulović, Siniša; Tešić, Živoslav Lj.

doi:10.1002/bmc.1091

Cited by 22 publications

(15 citation statements)

References 32 publications

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“…Compound 9 without such a cumbersome fatty acid substituent and a relatively large P‐ASA value, in contrast, was found to be inactive. The long chain fatty acyl group could also increase the hydrophobicity of compounds, beneficial for their membrane crossing, which is essential for receptor interactions (Atrrog et al , ).…”

Section: Resultsmentioning

confidence: 99%

Bioactivity‐guided Isolation of Antiproliferative Diterpenoids from Euphorbia kansui

Wang

Wei

et al. 2011

Phytotherapy Research

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Cytotoxic assay guided multistep separation on the dichloromethane extract of the roots of Euphorbia kansui resulted in the isolation of 10 ingenol-type diterpenoids (1-4 and 7-12), of which, 5-O-(2'E,4'E-decadienoyl)-20-O-acetylingenol (1) is a new compound, and two are jatrophane-type diterpenoids (13-14). Interconversion of two pairs of positional ester isomers (1-4) in aqueous alcoholic solution was observed, the transesterification mechanism of which was speculated and confirmed by acylation of 3 and 4 to 6 and 5, respectively. All the isolates and the two acyl derivatives (5 and 6) were evaluated in vitro for their cytotoxicities in Bel-7402, Bel-7402/5FU, BGC-823 and SGC-7901 cell lines. The 12 ingenol-type diterpenoids exhibited weak to moderate cytotoxicities, whereas the two jatrophane-type diterpenoids displayed no antiproliferative effects, which, however, may increase the antitumour efficacy of those ingenol-type diterpenoids. The structure--activity relationships were investigated by principal component analysis (PCA) of the pIC₅₀ (-logIC₅₀) values of the compounds tested and their calculated molecular descriptors. The pIC₅₀ values were highly correlated with most descriptors, especially the highest occupied molecular orbital energy (E(HOMO)), absolute hardness (η) and positively charged solvent accessible surface areas (P-ASA). As the values of E(HOMO) increase, η and P-ASA decrease, and the antiproliferative effects of these compounds increase.

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Section: Resultsmentioning

confidence: 99%

Bioactivity‐guided Isolation of Antiproliferative Diterpenoids from Euphorbia kansui

Wang

Wei

et al. 2011

Phytotherapy Research

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“…Extensive spectroscopic ( 1 H NMR) and HPLC PDA/ESI MS analysis of the crude extracts and their purified constituents revealed 21 new guaianolide SLs, named amphoricarpolides (Djordjević et al 2004;Djordjević et al 2006) as the main constituents (≥ 1 % per weight of dried plant material). Some of the isolated amphoricarpolides were screened for their cytotoxicity on human cervical cancer (HeLa) and murine melanoma (B16) cell lines, and most of them have shown reasonable cytotoxic activities (Atrrog et al 2009). Our recent study of biological activity of the surface extract, mostly constituting amphoricarpolides, from the aerial parts of A. neumayeri ssp.…”

Section: Phytochemical Investigationsmentioning

confidence: 99%

Ethnobotany and Biocultural Diversities in the Balkans

Pieroni¹,

Quave²

2014

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“…Chemical structure is the main factor that determines a drug's affinity and activity (Atrrog et al, ; Czopek et al, ; Rabtti et al, ). Some structural parameters are of more importance for the activity than others.…”

Section: Introductionmentioning

confidence: 99%

QSAR characterization of new synthesized hydantoins with antiproliferative activity

Tot

Lazić

Božić

et al. 2019

Biomedical Chromatography

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Hydantois have been identified as constituents of a number of pharmacologically active molecules. In the present study, we have examined in vitro antiproliferative activity against human colon cancer cell lines HCT-116 of three series of 3-(4substituted benzyl)-hydantoins with various substituent attached in position 5 of the hydantoin ring. Since the investigated compounds have recently been synthesized and show antiproliferative activity, a good understanding of the properties of the potential drug responsible for their pharmacokinetics is an important goal for their further development. One of the important properties is lipophilicity. Lipophilicity has been assessed by reversed-phase liquid chromatography (high-performance thin-layer chromatography and high-pressure liquid chromatography) by means of direct and indirect (using calibration curve) methods. Chromatographic lipophilicity indices in addition to calculated logP values were compared by hierarchical cluster analysis. The linear solvation energy relationship approach was used to understand and compare the types and relative strength of the molecular interactions that occur in the chromatographic as well as in the n-octanol-water partitioning systems. Finally, correlation between in silico pharmacokinetic predictors and antiproliferative activity was examined. Preliminary quantitative structure-activity relationship modeling indicates that pharmacokinetic predictors capture only one-quarter of all chemical features that are important for antiproliferative activity itself. Among selected descriptors are chromatographic lipophilicity indices.

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Lipophilicity of some guaianolides isolated from two endemic subspecies of Amphoricarpos neumayeri (Asteraceae) from Montenegro

Cited by 22 publications

References 32 publications

Bioactivity‐guided Isolation of Antiproliferative Diterpenoids from Euphorbia kansui

Bioactivity‐guided Isolation of Antiproliferative Diterpenoids from Euphorbia kansui

Ethnobotany and Biocultural Diversities in the Balkans

QSAR characterization of new synthesized hydantoins with antiproliferative activity

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