"Conformational study of arbutin by quantum chemical calculations and multivariate analysis"

C. ARAUJO-ANDRADE, S. LOPES, R. FAUSTO AND A. GÓMEZ ZAVAGLIA.

Florencia

Congreso; XXXth European Congress on Molecular Spectroscopy (EUCMOS 2010). Florencia. Italia. 30/8/2010-3/9/2010.; 2010

EUCMOS

Arbutin (IUPAC name: (2R,3S,4S,5R,6S)-2-hydroxymethyl-6-(4-hydroxyphen oxy)oxane-3,4,5-triol, also known as hydroquinone-b-D-glucopyranoside) is an abundant solute in the leaves of many freezing- or desiccation-tolerant plants (Figure 1) [1]. Taking into account the protective role of arbutin in such plants and the importance of OH groups on the physico-chemical and biological function of sugars as cryoprotectants, a deep analysis of the molecular structure of arbutin may be very useful for the elucidation of the molecular mechanisms involved in its role as cryoprotectant. Arbutin has eight conformationally relevant dihedral angles, five of them related with the orientation of the hydroxyl groups and the remaining three taking part in the skeletal of the molecule. In this study, a systematic search on the conformational space of arbutin was performed. Conformers were grouped according to structural similarities using multivariate analyses and correlations between their structures and several properties established [2]. Intramolecular interactions involving OH groups were also investigated and correlations between spectroscopic, structural and thermodynamic properties established. The strategy here used might be useful to investigate the structure and structure/properties correlations in other biologically relevant conformationally flexible molecules, in particular carbohydrates.