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New Casbanes and the First trans ‐Cyclopropane seco ‐Casbane from the Australian Rainforest Plant Croton insularis
Author(s) -
Maslovskaya Lidiya A.,
Savchenko Andrei I.,
Pierce Carly J.,
Boyle Glen M.,
Gordon Victoria A.,
Reddell Paul W.,
Parsons Peter G.,
Williams Craig M.
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201804904
Subject(s) - cyclopropane , croton , moiety , rainforest , stereochemistry , absolute configuration , chemistry , botany , ring (chemistry) , biology , organic chemistry
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).