A1 Journal article (refereed)
A New Benzopyranyl Cadenane Sesquiterpene and Other Antiplasmodial and Cytotoxic Metabolites from Cleistochlamys kirkii (2019)

Nyandoro, S. S., Maeda, G., Munissi, J. J., Gruhonjic, A., Fitzpatrick, P. A., Lindblad, S., Duffy, S., Pelletier, J., Pan, F., Puttreddy, R., Avery, V. M., & Erdélyi, M. (2019). A New Benzopyranyl Cadenane Sesquiterpene and Other Antiplasmodial and Cytotoxic Metabolites from Cleistochlamys kirkii. Molecules, 24(15), Article 2746. https://doi.org/10.3390/molecules24152746

JYU authors or editors

Publication details

All authors or editors: Nyandoro, Stephen S.; Maeda, Gasper; Munissi, Joan J.E.; Gruhonjic, Amra; Fitzpatrick, Paul A.; Lindblad, Sofia; Duffy, Sandra; Pelletier, Jerry; Pan, Fangfang; Puttreddy, Rakesh; et al.

Journal or series: Molecules

eISSN: 1420-3049

Publication year: 2019

Volume: 24

Issue number: 15

Article number: 2746

Publisher: MDPI

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/molecules24152746

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/65307

Abstract

Phytochemical investigations of ethanol root bark and stem bark extracts of Cleistochlamys kirkii (Benth.) Oliv. (Annonaceae) yielded a new benzopyranyl cadinane-type sesquiterpene (cleistonol, 1) alongside 12 known compounds (2–13). The structures of the isolated compounds were established from NMR spectroscopic and mass spectrometric analyses. Structures of compounds 5 and 10 were further confirmed by single crystal X-ray crystallographic analyses, which also established their absolute stereochemical configuration. The ethanolic crude extract of C. kirkii root bark gave 72% inhibition against the chloroquine-sensitive 3D7-strain malaria parasite Plasmodium falciparum at 0.01 μg/mL. The isolated metabolites dichamanetin, (E)-acetylmelodorinol, and cleistenolide showed IC50 = 9.3, 7.6 and 15.2 μM, respectively, against P. falciparum 3D7. Both the crude extract and the isolated compounds exhibited cytotoxicity against the triple-negative, aggressive breast cancer cell line, MDA-MB-231, with IC50 = 42.0 μg/mL (crude extract) and 9.6–30.7 μM (isolated compounds). Our findings demonstrate the potential applicability of C. kirkii as a source of antimalarial and anticancer agents.

Keywords: naturally occurring substances; terpenes; pharmaceutical chemistry; malaria; cancer treatments

Free keywords: Cleistochlamys kirkii; Annonaceae; benzopyranyl sesquiterpene; cleistonol; antiplasmodial activity; malaria; cytotoxicity

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2019

JUFO rating: 1