Foetidumins A-D, and other chemical constituents from Helichrysum foetidum (L.) Moench (Asteraceae) with antiparasite activity

Hermine Wete Nono; Arno Rusel Donfack Nanfack; Billy Toussie Tchegnitegni; Cyrille Armel Njanpa Ngansop; Faustine Léonie Mafodong Dongmo; Maurice Ducret Awouafack; Fabrice Fekam Boyom; Bruno Lenta Ndjakou; Hans-Georg Stammler; Beate Neumann; Norbert Sewald; Silvère Augustin Ngouela

doi:10.1016/j.phytochem.2023.113672

Foetidumins A-D, and other chemical constituents from Helichrysum foetidum (L.) Moench (Asteraceae) with antiparasite activity

Phytochemistry. 2023 Jun:210:113672. doi: 10.1016/j.phytochem.2023.113672. Epub 2023 Apr 9.

Affiliations

¹ Department of Chemistry, University of Dschang, P.O. Box 67, Dschang, Cameroon; Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon.
² Department of Chemistry, University of Dschang, P.O. Box 67, Dschang, Cameroon. Electronic address: arnonanfack@yahoo.com.
³ Department of Chemistry, University of Dschang, P.O. Box 67, Dschang, Cameroon.
⁴ Department of Biochemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon.
⁵ Department of Basic Scientific Education, University Institute of Technology, University of Ngaoundere, P.O. Box: 455, Ngaoundere, Cameroon.
⁶ Department of Chemistry, Higher Teacher Training College, University of Yaoundé I, P.O. Box 47 Yaounde, Cameroon.
⁷ Inorganic and Structural Chemistry, Faculty of Chemistry, Bielefeld University, D-33501, Bielefeld, Germany.
⁸ Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, D-33501, Bielefeld, Germany.
⁹ Department of Chemistry, University of Dschang, P.O. Box 67, Dschang, Cameroon; Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon. Electronic address: sngouela@yahoo.fr.

PMID: 37040830
DOI: 10.1016/j.phytochem.2023.113672

Abstract

The phytochemical investigation of the MeOH and CH₂Cl₂-MeOH (1:1) extracts from the flowers and twigs of Helichrysumfoetidum (L.) Moench (Asteraceae), which showed antileishmanial and antiplasmodial activities during the preliminary screening, led to the isolation of four undescribed compounds, including two ent-beyer-15-ene-type diterpenoids, foetidumins A (1) and B (2), one flavonoid, foetidumin C (3) and one chalcopyrone, foetidumin D (4). Additionally, fourteen known compounds comprising, two ent-beyer-15-ene-type diterpenoids (5-6), six flavonoids (7-12), two steroids (13-14), three triterpenoids (15-17), and one glyceryl monostearate (18) were also isolated. The chemical structures of foetidumins A-D were fully elucidated by analyses of their spectroscopic data. The structure and the stereochemistry of foetidumin A (1) were confirmed by SC-XRD analyses. Among the tested compounds, foetidumin C (3), erythroxylol A (6), and kaempferol (7) displayed the highest antileishmanial potency with IC₅₀ values of 13.0, 11.8, and 11.1 μM, respectively. Foetidumin C (3) had no cytotoxicity toward Vero cells with the selectivity index > 3.59. Meanwhile, extracts of flowers and twigs had higher activity against Plasmodium falciparum chloroquine-sensitive (Pf3D7) strain with IC₅₀ values of 3.66 and 10.52 μg/mL, respectively.

Keywords: Antiparasite; Asteraceae; Foetidumins A-D; Helichrysum foetidum; SC-XRD analysis.

MeSH terms

Animals
Anti-Infective Agents*
Antimalarials* / chemistry
Antiparasitic Agents
Asteraceae* / chemistry
Chlorocebus aethiops
Diterpenes* / pharmacology
Helichrysum* / chemistry
Plant Extracts / chemistry
Plasmodium falciparum
Vero Cells

Substances

Antimalarials
Antiparasitic Agents
Plant Extracts
Anti-Infective Agents
Diterpenes