ABSTRACT
The inclusion compounds of carvone enantiomers in cylcomaltoheptaose (beta-cyclodextrin, betaCD) are studied at defined temperatures above room temperature and in relation to H-->D and D-->H exchanges. Loss of water molecules and release of carvone molecules from the betaCD cavity are caused by increase of temperature above room temperature and are measured by the integrated intensities of the O-H and C-H Raman stretching bands, respectively. In turn, H-->D and D-->H exchanges are monitored by the integrated intensities of the O-H and O-D Raman stretching bands, respectively. All of these processes were followed in real time with a Raman spectrometer equipped with CCD detection. The results indicate that distinct carvone enantiomers lead to the formation of different betaCD inclusion hydrates that have different water content and hydration structures. In particular, the results suggest that SCarv-betaCD has a greater water content, dehydrates strongly for temperatures above room temperature, and exchanges protons faster than the RCarv-betaCD complex.
Subject(s)
Cyclodextrins/chemistry , Terpenes/chemistry , beta-Cyclodextrins , Binding Sites , Cyclohexane Monoterpenes , Deuterium , Hydrogen , Monoterpenes , Spectrum Analysis, Raman , Stereoisomerism , Temperature , Water/chemistryABSTRACT
Two Gram-negative bacterial strains capable of using lupanine, the predominant quinolizidine alkaloid in Lupinus albus, as a sole carbon source were isolated from soil in which L. albus and L. luteus had been grown [Santana, F. M. et al. J. Ind. Microbiol. 1996, 17, 110-115]. In the present study, we present results suggesting that these isolates are of potential interest for removing lupanine and other quinolizidine alkaloids (QA) from the effluent resulting from the wet processing of Lupinus seeds, at temperatures within the range 20-34 degrees C. Growth in L. albus aqueous extract was diauxic, with a first period of rapid growth leading to the simultaneous consumption of a significant part of the initial concentration of QA (3 g L(-1), being 2 g L(-1) lupanine) and amino acids (1.5 g L(-1)). This period was followed by a second period of slower growth corresponding to the subsequent partial utilization (25%) of the carbohydrates (initial concentration of 20 g L(-1)) together with further removal of QA and amino acids. Despite the differences detected in the susceptibility of the two strains to lupanine toxicity, in particular at supraoptimal temperatures, and in the efficiency of lupanine catabolism, their performance on L. albus extract did not vary significantly.