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

Autor: Cao DH; Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, 666303, PR China; University of Chinese Academy of Sciences, Beijing, 100049, PR China; Department of Ecogenomics and Systems Biology, University of Vienna, Althanstrasse 14, Vienna, 1090, Austria., Liao SG; State Key Laboratory of Functions and Applications of Medicinal Plants & School of Pharmacy, Guizhou Medical University, Guizhou, 550025, PR China., Sun P; Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, 666303, PR China; University of Chinese Academy of Sciences, Beijing, 100049, PR China., Xiao YD; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, 650201, PR China; School of Chemical Science and Technology, Key Laboratory of Medicinal Chemistry for Nature Resource, Ministry of Education, Yunnan University, Kunming, 650091, PR China., Xiao CF; Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, 666303, PR China., Hu HB; Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, 666303, PR China., Weckwerth W; Department of Ecogenomics and Systems Biology, University of Vienna, Althanstrasse 14, Vienna, 1090, Austria; Vienna Metabolomics Center (VIME), University of Vienna, Althanstrasse 14, Vienna, 1090, Austria., Xu YK; Key Laboratory of Tropical Plant Resources and Sustainable Use, Xishuangbanna Tropical Botanical Garden, Chinese Academy of Sciences, Menglun, 666303, PR China. Electronic address: xyk@xtbg.ac.cn.
Jazyk: angličtina
Zdroj: Phytochemistry [Phytochemistry] 2020 Sep; Vol. 177, pp. 112449. Date of Electronic Publication: 2020 Jun 26.
DOI: 10.1016/j.phytochem.2020.112449
Abstrakt: 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 α,β-unsaturated-γ-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 IC 50 values ranging from 18.56 ± 0.27 to 38.00 ± 0.85 μM, 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 μM.
(Copyright © 2020 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
Externí odkaz: