engleski

Molecular modeling of wine polyphenols

Due to wide range of health effects of wine polyphenols, it is important to investigate the relationship between their structure and physical properties (quantitative structure-property relationship, QSPR). We have investigated linear, nonlinear (polynomial), and multiple linear relationships between given topological indices and molecular properties of main pharmacological active components of wine, such as molecular weight (MW), van der Waals volume (Vw), molar refractivity (MR), polar molecular surface area (PSA) and lipophilicity (log P). Partition coefficient (log P) was calculated using three different computer program (CLOGP, ALOGPS and MLOGP) and best results were achieved using the MLOGP program. Topological indices used for correlation analysis include: the Wiener index, W(G) ; connectivity indices, c(G) ; Balaban index, J(G) ; information-theoretic index, I(G) ; and Schultz index, MTI. QSPR was performed on the set of 19 polyphenols and, particularly, on the group of phenolic acids, and on the group of flavonoids with resveratrol. The connectivity index has been successfully used for describing almost all parameters. Significant correlations were achieved between the Wiener index and van der Waals volume, as well as molecular weight.

polyphenols ; topological indices ; molecular descriptors ; physico-chemical properties ; QSPR

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