Journal
PHYTOCHEMISTRY
Volume 163, Issue -, Pages 38-45Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.phytochem.2019.03.024
Keywords
Picramnia glazioviana Engl. (Picramniaceae); Nortriterpenes; Picravianes A and B; Vibrational circular dichroism; Electronic circular dichroism; Triple negative breast cancer
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Funding
- Sao Paulo Research Foundation (FAPESP) [2013/20458-1, 2016/18024-1]
- FAPESP [2012/25299-6, 2014/25222-9, 2015/07089-2, 2016/23794-0]
- National Council for Scientific and Technological Development (CNPq) [305190/2017-2]
- Coordination for the Improvement of Higher Education Personnel (CAPES) [001]
- Danish Agency for Science, Technology and Innovation via the National Research Infrastructure funds
- 'Apotekerfonden of 1991', The Carlsberg Foundation
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Two highly oxygenated nortriterpenes, picraviane A and B, were isolated from the ethanolic extract of Picramnia glazioviana Engl. The structures were determined by analysis of HRMS and 2D NMR spectroscopic data. Single-crystal X-ray diffraction data was also obtained for picraviane B. The absolute configuration of both compounds were assigned by comparison of experimental and calculated vibrational and electronic circular dichroism spectroscopy, respectively. Picraviane A showed a moderate cytotoxic activity against the triple negative MDA-MB-231 breast cancer cell line. These compounds represent an undescribed class of natural products with limonoid-like skeletons containing a heptanolide as the E-ring.
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