New Casbanes and the First trans‐Cyclopropane seco‐Casbane from the Australian Rainforest Plant Croton insularis. Issue 6 (2nd January 2019)

• Record Type: Journal Article
• Authors: Maslovskaya, Lidiya A.; Savchenko, Andrei I.; Pierce, Carly J.; Boyle, Glen M.; Gordon, Victoria A.; Reddell, Paul W.; Parsons, Peter G.; Williams, Craig M.
• Is Part Of: Chemistry. Volume 25:Issue 6(2019)
• Page Start: 1525
• Page End: 1534
• Publication Date: 2019-01-02
• Subjects: casbanes -- ECD calculations -- natural products -- seco-casbanes -- terpenoids; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201804904
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: Investigation of the Australian rainforest plant Croton insularis revealed seven new cis ‐, two new trans ‐cyclopropane casbanes, and the first trans ‐cyclopropane seco ‐casbane. The relative configuration of the cyclopropane moiety for all compounds (EBC‐182, 217, 218, 220, 343, 357, 358, 361, 365, 373; EBC=EcoBiotics Compound) was assigned using 13 C NMR data. Comparison of the experimental electronic circular dichroism (ECD) spectra with the theoretical curves, calculated by TD‐DFT at the B3LYP/6‐31+G**//B3LYP/6‐31+G** level, in conjunction with NOE data afforded the absolute configuration. EBC‐180, 181 and 220 displayed potent activity against cervical carcinoma (HeLa cells). Abstract : Ask for casbanes and Croton giveth : The Australian rainforest plant Croton Insularis revealed new cis ‐ and trans ‐casbanes, along with the first trans ‐ seco ‐casbane. Absolute configuration of all 10 casbanes was determined by ECD and one derivative displayed potent activity against HeLa cells.