A New Benzopyranyl Cadenane Sesquiterpene and Other Antiplasmodial and Cytotoxic Metabolites from Cleistochlamys kirkii

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Stephen S NyandoroMáté Erdélyi

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.

References

Apr 15, 1977·The Journal of Organic Chemistry·W L Lasswell, C D Hufford
Jan 1, 1987·Journal of Ethnopharmacology·R Verzár, G Petri
Jan 26, 2002·Journal of Natural Products·Yueh-Hsiung KuoYun-Lian Lin
Aug 13, 2003·Chemical & Pharmaceutical Bulletin·Yueh-Hsiung KuoHsiu-Chuan Lin
Feb 11, 2004·Nucleic Acids Research·Olivia NovacJerry Pelletier
Jan 11, 2012·The American Journal of Tropical Medicine and Hygiene·Sandra Duffy, Vicky M Avery
Dec 15, 2015·Journal of Natural Products·Tsegaye DeyouAbiy Yenesew
Dec 22, 2016·Journal of Natural Products·Stephen S NyandoroMáté Erdélyi
Feb 24, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yoseph AtilawAbiy Yenesew

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Citations

May 18, 2021·Chemistry & Biodiversity·Han ChenXiaoling Lu
Aug 28, 2020·Journal of Natural Products·Linda ZandiMáté Erdélyi

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Datasets Mentioned

BETA
YSA
3652

Methods Mentioned

BETA
gel filtration
NMR
X-ray
gravitational column chromatography
circular dichroism
column chromatography

Software Mentioned

Chromulan
MestreNova

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