Mexicanolide-type limonoids from the twigs and leaves of Cipadessa baccifera

Author(s)
Dong-Hua Cao, Shang-Gao Liao, Peng Sun, Yi-Dian Xiao, Chun-Fen Xiao, Hua-Bin Hu, Wolfram Weckwerth, You-Kai Xu
Abstract

Twelve previously undescribed mexicanolide-type limonoids, including two pairs of isomers, together with seven known analogues were isolated from the twigs and leaves of Cipadessa baccifera. Their structures were determined by extensive spectroscopic methods and electronic circular dichroism (ECD) calculations. Structural variations mainly occurred at the attachment of C-3 and the carbon residues linked to C-17. 21-deoxo-23-oxofebrifugin A and 3-O-detigloyl-3-O-isobutyryl-21-deoxo-23-oxofebrifugin A are two rare naturally occurring mexicanolide-type limonoids bearing an alpha,beta-unsaturated-gamma-lactone motif at C-17. Moreover, cipaferen R is the first degraded tetranortriterpenoid derivative featuring an unique acetyl group at C-17. Some isolated compounds were evaluated for nematicidal, antifungal, cytotoxic (against five human cancer cell lines), and acetylcholinesterase inhibitory activities. No nematicidal and antifungal activities were observed, yet 3-O-detigloyl-3-O-isobutyrylfebrifugin A, febrifugin A, febrifugin, and khaysin T exhibited moderate cytotoxic activity against the tested cells with IC50 values ranging from 18.56 +/- 0.27 to 38.00 +/- 0.85 mu M, and 3-O-detigloyl-3-O-isobutyrylfebrifugin A, granatumin E, khaysin T, and 2'S-cipadesin A showed moderate inhibitory activities against acetylcholinesterase (AChE) at 50 mu M.

Organisation(s)
Functional and Evolutionary Ecology, Large-Instrument Facility for Mass Spectrometry in Life Sciences, Research Platform Vienna Metabolomics Center
External organisation(s)
Chinese Academy of Sciences, Xishuangbanna Tropical Botanical Garden, University of the Chinese Academy of Sciences, Guizhou Medical University, Chinese Academy of Sciences (CAS), Yunnan University, Universität Wien
Journal
Phytochemistry
Volume
177
No. of pages
10
ISSN
0031-9422
DOI
https://doi.org/10.1016/j.phytochem.2020.112449
Publication date
09-2020
Peer reviewed
Yes
Austrian Fields of Science 2012
106031 Plant physiology, 106002 Biochemistry, 301214 Biopharmacy, 106030 Plant ecology
Keywords
Portal url
https://ucris.univie.ac.at/portal/en/publications/mexicanolidetype-limonoids-from-the-twigs-and-leaves-of-cipadessa-baccifera(c8c5e666-6ba9-40ab-a082-c9b16ba50685).html