Synthesis and biological activity of new derivatives with the preserved carane system |
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| Authors: | Agata Kozio? Jakub Fr?tczak Ewa Grela Maryla Szczepanik Beata Gabry? Katarzyna Dancewicz |
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| Institution: | 1. Department of Bioorganic Chemistry, Faculty of Chemistry, Wroc?aw University of Science and Technology, Wroc?aw, Poland;2. Institute of Cosmetology, Academy of Physiotherapy in Wroc?aw, Wroc?aw, Poland;3. agata.koziol1@wp.pl;5. Department of Invertebrate Zoology, Nicolaus Copernicus University, Toruń, Poland;6. Department of Botany and Ecology, Faculty of Biological Sciences, University of Zielona Góra, Zielona Góra, Poland |
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| Abstract: | AbstractTerpenoid derivatives, which contain a preserved carane system in their structure, exhibit a broad spectrum of biological activities. Among them, we can distinguish insecticides, structures with pharmacological application etc. In the presented paper, the substrate - (–)-cis-caran-trans-4-ol was transformed using the reactions of typical organic synthesis to obtain novel derivatives. Most importantly, bromolactone ((–)-(1R,4R,6S)-2'-(bromomethyl)-4,7,7-trimethylspirobicyclo4.1.0]heptan-3,3'-furan]-5'(4'H)-one) with the preserved carane system was synthesized. This bromolactone was tested for antifeedant activity against the lesser mealworm, Alphitobius diaperinus Panzer, and peach potato aphid (Myzus persicae). In addition, its moderate antibacterial activity was observed against the Bacillus subtilis strain (with Minimal Inhibitory Concentration of 200 µg/mL). |
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| Keywords: | (+)-carene bromolactone antifeedant activity antibacterial activity |
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