New unsaturated fatty acid and other chemical constituents from the roots of Cola rostrata K. Schum. (Malvaceae)

• Published in: Biochemical systematics and ecology 2019-10, Vol.86, p.103913, Article 103913
• Main Authors: Tékapi Tsopgni, Willifred Dongmo, Blaise Azebaze, Anatole Guy, Mbosso Teinkela, Jean Emmanuel, Ndjakou, Bruno Lenta, Bosyom, Fabrice Fekam, Tchaleu, Bonaventure Ngadjui, Vardamides, Juliette Catherine
• Format: Article
• Language: English
• Subjects: Antimicrobial; Chemotaxonomic; Cola rostrata; Cytotoxicity; Fatty acid; Malvaceae; Roots; Semisynthetic
• ISSN: 0305-1978; 1873-2925
• DOI: 10.1016/j.bse.2019.103913

Phytochemical investigation of the roots of Cola rostrata K. Schum. led to the isolation of a new unsaturated fatty acid, named rostratanic acid (1), together with fourteen known compounds, lignoceric acid, friedelan (7), friedelanone (8), bauerenol (3), lupeol (4), herranone (9), acotatarone A (11), betulinic acid (6), betulin (5), nonanedioc acid (2), arjunolic acid (10) stigmasterol, β−sitosterol, and β−sitosterol-3-O-β-D-glucopyranoside. The structure of the new compound as well as those of the known compounds were established by means of spectroscopic methods: NMR analysis (1H and 13C NMR, 1H–1H–COSY, HSQC and HMBC) and high-resolution mass spectrometry (HR-ESI-MS), and by comparison with previously reported data. Two of those known compounds were modified chemically to afford three new derivatives. All those compounds were tested for their cytotoxic activity against the human cervix carcinoma KB-3-1 cells and their antibacterial activity against Escherichia coli, Salmonella enterica, Pseudomonas aeruginosa and Staphylococcus aureus. Although the crude extract gave weak antibacterial activity, none of the isolated compounds showed antibacterial activity, and, only the prenylated derivative showed weak cytotoxicity. In addition, the chemotaxonomic significance of the species Cola rostrata is discussed. [Display omitted] •Isolation of a new fatty acid, rostratanic acid.•Isolation of rostratanic acid as a new unsaturated fatty acid and identification of fourteen other compounds (lignoceric acid, friedelan (7), friedelanone (8), bauerenol (3), lupeol (4), herranone (9), acotatarone A (11), betulinic acid (6), betulin (5), nonanedioc acid (2), arjunolic acid (10), stigmasterol and β−sitosterol, stigmasterol and β−sitosterol glucoside).•Preparation of three semi-synthetic derivatives.•Antimicrobial and cytotoxic assay