Synthesis and biological activity of new derivatives with the preserved carane system. Issue 10 (18th May 2020)

• Record Type: Journal Article
• Authors: Kozioł, Agata; Frątczak, Jakub; Grela, Ewa; Szczepanik, Maryla; Gabryś, Beata; Dancewicz, Katarzyna; Lochyński, Stanisław
• Is Part Of: Natural product research. Volume 34:Issue 10(2020)
• Page Start: 1399
• Page End: 1403
• Publication Date: 2020-05-18
• Subjects: (+)-carene -- bromolactone -- antifeedant activity -- antibacterial activity; Natural products -- Periodicals; Natural products -- Research -- Periodicals; Biological Factors -- Periodicals; Biological Products -- Periodicals; 547
• DOI: 10.1080/14786419.2018.1512992
• Languages: English
• ISSNs: 1478-6419

Abstract

Abstract: Terpenoid 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-trimethylspiro[bicyclo[4.1.0]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). Graphical Abstract: