Quantitative Structure-Retention Relationships Studies of Selected Groups of Compounds Characterized by Different Pharmacological Activity Using Multiple Linear Regression Procedure

The chemical composition of the volatile fraction obtained by head-space solid phase microextraction (HS-SPME), single drop microextraction (SDME) and the essential oil obtained by cold-press from the peels of C. sinensis cv. valencia were analyzed employing gas chromatography-flame ionization detector (GC-FID) and gas chromatography-mass spectrometry (GC-MS). The main components were limonene (61.34 %, 68.27 %, 90.50 %), myrcene (17.55 %, 12.35 %, 2.50 %), sabinene (6.50 %, 7.62 %, 0.5 %) and ?-pinene (0 %, 6.65 %, 1.4 %) respectively obtained by HS-SPME, SDME and cold-press. Then a quantitative structure-retention relationship (QSRR) study for the prediction of retention indices (RI) of the compounds was developed by application of structural descriptors and the multiple linear regression (MLR) method. Principal components analysis was used to select the training set. A simple model with low standard errors and high correlation coefficients was obtained. The results illustrated that linear techniques such as MLR combined with a successful variable selection procedure are capable of generating an efficient QSRR model for prediction of the retention indices of different compounds. This model, with high statistical significance (R2 train = 0.983, R2 test = 0.970, Q2 LOO = 0.962, Q2 LGO = 0.936, REP(%) = 3.00), could be used adequately for the prediction and description of the retention indices of the volatile compounds.

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Prediction of the retention of β-diketonato complexes in TLC systems on silica gel by quantitative structure-retention relationships

Journal of the Serbian Chemical Society ◽

10.2298/jsc090225002b ◽

2010 ◽

Vol 75 (4) ◽

pp. 513-521 ◽

Cited By ~ 1

Author(s):

Rada Baosic ◽

Ana Radojevic ◽

Zivoslav Tesic

Keyword(s):

Linear Regression ◽

Multiple Linear Regression ◽

Surface Area ◽

Molecular Orbital ◽

Silica Gel ◽

Molecular Descriptors ◽

Quantitative Structure ◽

Hydrophilic Lipophilic Balance ◽

Structure Retention ◽

Retention Parameters

Quantitative structure-retention relationships for a series of 30 mixed ?-diketonato complexes of cobalt(III), chromium(III) and ruthenium(III) were derived by multiple linear regression analyses using molecular descriptors obtained by quantum chemical calculations. The retention parameters were obtained by thin layer chromatography on silica gel using mono and two-component solvent systems. The molecular descriptors included in the multiple linear regression analysis were molecular weight, molecular volume, surface area, hydrophilic-lipophilic balance, percent hydrophilic surface area, dipole moment, polarizability, refractivity, energy of the highest occupied molecular orbital and energy of the lowest unoccupied molecular orbital. High agreement between the experimental and predicted retention parameters was obtained when polarizability and the hydrophilic-lipophilic balance were used as the molecular descriptors. Comparison of the models with those established on polyacrylonitrile showed that the structure of the sorbent is responsible for the chromatographic behaviour of the same compounds. The presented models can be used for the prediction of the retention of new solutes in screening chromatographic systems.

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