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

Nyandoro, Stephen S.; Maeda, Gasper; Munissi, Joan J.E.; Gruhonjic, Amra; Fitzpatrick, Paul A.; Lindblad, Sofia; Duffy, Sandra; Pelletier, Jerry; Pan, Fangfang; Puttreddy, Rakesh; Avery, Vicky M. et al. (2019). A New Benzopyranyl Cadenane Sesquiterpene and Other Antiplasmodial and Cytotoxic Metabolites from Cleistochlamys kirkii. Molecules, 24 (15), 2746. DOI: 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: http://doi.org/10.3390/molecules24152746

Open Access: Publication published in an 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