Foetidumins A-D, and other chemical constituents from Helichrysum foetidum (L.) Moench (Asteraceae) with antiparasite activity. (June 2023)

• Record Type: Journal Article
• Authors: Nono, Hermine Wete; Donfack Nanfack, Arno Rusel; Tchegnitegni, Billy Toussie; Njanpa Ngansop, Cyrille Armel; Mafodong Dongmo, Faustine Léonie; Awouafack, Maurice Ducret; Fekam Boyom, Fabrice; Ndjakou, Bruno Lenta; Stammler, Hans-Georg; Neumann, Beate; Sewald, Norbert; Ngouela, Silvère Augustin
• Is Part Of: Phytochemistry. Volume 210(2023)
• Publication Date: 2023-06
• Subjects: Helichrysum foetidum -- Asteraceae -- SC-XRD analysis -- Foetidumins A-D -- Antiparasite; Botanical chemistry -- Periodicals; Biochemistry -- Periodicals; Botany -- Periodicals; Chimie végétale -- Périodiques; 572.2
• DOI: 10.1016/j.phytochem.2023.113672
• Languages: English
• ISSNs: 0031-9422

Abstract

Abstract: The phytochemical investigation of the MeOH and CH2 Cl2 –MeOH (1:1) extracts from the flowers and twigs of Helichrysum foetidum (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 ( Pf 3D7) strain with IC50 values of 3.66 and 10.52 μg/mL, respectively. Graphical abstract: Image 1 Highlights: Four undescribed compounds and fourteen known ones were isolated from H. foetidum. Their structures were fully elucidated using NMR, HRMS and SC-XRD analyses. This is the first report of Hederagenin 3-O- β -D-glucopyranoside from Helichrysum. Foetidumin C, erythroxylol A, and kaempferol had highest antileishmanial potency. Foetidumin C had no toxicity toward Vero cells (SI > 3.59).