Di-nor- and 17-nor-pimaranes from Icacina trichantha

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...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2016-07, Vol.79 (7), p.1815-1821
Main Authors: Guo, Brian, Onakpa, Monday M, Huang, Xiao-Jun, Santarsiero, Bernard D, Chen, Wei-Lun, Zhao, Ming, Zhang, Xiao-Qi, Swanson, Steven M, Burdette, Joanna E, Che, Chun-Tao
Format: Article
Language:English
Subjects:
Crystallography, X-Ray
Diterpenes, Abietane - chemistry
Diterpenes, Abietane - isolation & purification
Diterpenes, Abietane - pharmacology
Drug Screening Assays, Antitumor
Magnoliopsida - chemistry
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Tubers - chemistry
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Summary: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.
ISSN:0163-3864
1520-6025
DOI:10.1021/acs.jnatprod.6b00289