Antiparasitic Constituents of Beilschmiedia louisii and Beilschmiedia obscura and Some Semisynthetic Derivatives (Lauraceae)

Christine C Waleguele; Brice M Mba'ning; Angelbert F Awantu; Jean J K Bankeu; Yannick S F Fongang; Augustin S Ngouela; Etienne Tsamo; Norbert Sewald; Bruno N Lenta; Rui W M Krause

doi:10.3390/molecules25122862

Antiparasitic Constituents of Beilschmiedia louisii and Beilschmiedia obscura and Some Semisynthetic Derivatives (Lauraceae)

Molecules. 2020 Jun 21;25(12):2862. doi: 10.3390/molecules25122862.

Affiliations

¹ Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812 Yaoundé, Cameroon.
² Department of Chemistry, Faculty of Science, The University of Bamenda, P.O. Box 39 Bambili, Cameroon.
³ Department of Chemistry, Higher Teacher Training College, The University of Maroua, P.O. Box 55 Maroua, Cameroon.
⁴ Department of Chemistry, Bielefeld University, P.O. Box 100131, 33501 Bielefeld, Germany.
⁵ Department of Chemistry, Higher Teacher Training College, University of Yaoundé I, P.O. Box 47 Yaoundé, Cameroon.
⁶ Department of Chemistry, Rhodes University, P.O. Box 94, Grahamstown 6140, South Africa.

Abstract

The MeOH/CH₂Cl₂ (1:1) extracts of the roots and leaves of Beilschmiedia louisii and B. obscura showed potent antitrypanosomal activity during preliminary screening on Trypanosoma brucei brucei. Phytochemical investigation of these extracts led to the isolation of a mixture of two new endiandric acid derivatives beilschmiedol B (1) and beilschmiedol C (2), and one new phenylalkene obscurene A (3) together with twelve known compounds (4-15). In addition, four new derivatives (11a-11d) were synthesized from compound 11. Their structures were elucidated based on their NMR and MS data. Compounds 5, 6, and 7 were isolated for the first time from the Beilschmiedia genus. Additionally, the NMR data of compound 4 are given here for the first time. The isolates were evaluated for their antitrypanosomal and antimalarial activities against Tb brucei and the Plasmodium falciparum chloroquine-resistant strain Pf3D7 in vitro, respectively. From the tested compounds, the mixture of new compounds 1 and 2 exhibited the most potent antitrypanosomal activity in vitro with IC₅₀ value of 4.91 μM.

Keywords: Beilschmiedia louisii; Beilschmiedia obscura; Lauraceae; antitrypanosomal activity; endiandric acid.

MeSH terms

Anti-Infective Agents / analysis*
Antimalarials / pharmacology*
Antiparasitic Agents / pharmacology*
Carboxylic Acids / chemistry*
Cell Survival / drug effects
Chloroquine / pharmacology
Inhibitory Concentration 50
Lauraceae / chemistry*
Magnetic Resonance Spectroscopy
Mass Spectrometry
Microbial Sensitivity Tests
Molecular Structure
Plant Extracts / chemistry*
Plant Extracts / pharmacology*
Plant Leaves / chemistry
Plant Roots / chemistry
Plasmodium falciparum / drug effects
Trypanosoma brucei brucei / drug effects

Substances

Anti-Infective Agents
Antimalarials
Antiparasitic Agents
Carboxylic Acids
Plant Extracts
endiandric acid
Chloroquine