Brian Guo1, Monday M Onakpa1,2, Xiao-Jun Huang3, Bernard D Santarsiero4, Wei-Lun Chen1, Ming Zhao1, Xiao-Qi Zhang3, Steven M Swanson1,5, Joanna E Burdette1, Chun-Tao Che1. 1. Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , Chicago, Illinois 60612, United States. 2. Department of Veterinary Pharmacology and Toxicology, Faculty of Veterinary Medicine, University of Abuja , Abuja 920001, Nigeria. 3. Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, People's Republic of China. 4. Center for Biomolecular Sciences and Department of Medicinal Chemistry and Pharmacognosy, University of Illinois at Chicago , Chicago, Illinois 60607, United States. 5. School of Pharmacy, University of Wisconsin-Madison , Madison, Wisconsin 53705, United States.
Abstract
Six new pimarane derivatives, including two di-nor-pimaranes (1, 2), two 17-nor-pimaranes (3, 4), and two 17-nor-(9β-H)-pimaranes (5, 6), were isolated from the tuber of Icacina trichantha. Their structures were elucidated based on spectroscopic and HRMS data. The absolute configurations of 1 and 5 were determined by single-crystal X-ray diffraction, and that of 2 was established by electronic circular dichroism data analysis. Compound 3 possesses a unique C-20 acetal moiety. This is the first report of the isolation of di-nor-(9β-H)-pimarane derivatives from Icacina plants. Compounds 5 and 6 showed moderate cytotoxicity against MDA-MB-435, MDA-MB-231, and OVCAR3 cell lines, with IC50 values of 2.91-7.60 and 1.48-3.23 μM, respectively.
Six new pimarane derivatives, including two n class="Chemical">di-nor-pimaranes (1, 2), two 17-nor-pimaranes (3, 4), and two 17-nor-(9β-H)-pimaranes (5, 6), were isolated from the tuber of Icacina trichantha. Their structures were elucidated based on spectroscopic and HRMS data. The absolute configurations of 1 and 5 were determined by single-crystal X-ray diffraction, and that of 2 was established by electronic circular dichroism data analysis. Compound 3 possesses a unique C-20 acetal moiety. This is the first report of the isolation of di-nor-(9β-H)-pimarane derivatives from Icacina plants. Compounds 5 and 6 showed moderate cytotoxicity against MDA-MB-435, MDA-MB-231, and OVCAR3 cell lines, with IC50 values of 2.91-7.60 and 1.48-3.23 μM, respectively.
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