Molecular Networking Reveals Serpentinine-Related Bisindole Alkaloids from Picralima nitida, a Previously Well-Investigated Species

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2020-04, Vol.83 (4), p.1207-1216
• Main Authors: Alcover, Charlotte Fox, Bernadat, Guillaume, Kabran, Faustin A, Le Pogam, Pierre, Leblanc, Karine, Fox Ramos, Alexander E, Gallard, Jean-François, Mouray, Elisabeth, Grellier, Philippe, Poupon, Erwan, Beniddir, Mehdi A
• Format: Article
• Language: English
• Subjects: Antiparasitic Agents; Antiparasitic Agents - chemistry; Antiparasitic Agents - pharmacology; Apocynaceae; Apocynaceae - anatomy & histology; Apocynaceae - chemistry; Chemical Sciences; Indole Alkaloids; Indole Alkaloids - chemistry; Life Sciences; Molecular Structure; Monoterpenes; Monoterpenes - chemistry; Monoterpenes - isolation & purification; Monoterpenes - pharmacology; Plasmodium falciparum; Plasmodium falciparum - chemistry; Secologanin Tryptamine Alkaloids; Secologanin Tryptamine Alkaloids - chemistry
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/acs.jnatprod.9b01247

Five new monoterpene indole alkaloids (1–5), including four serpentinine-related bisindoles and one alstonine derivative monomer, have been isolated from the aerial parts of Picralima nitida. Their structures were elucidated by analysis of their HRMS and NMR spectroscopic data, and their absolute configurations were deduced from the comparison of experimental and simulated ECD spectra. In addition, two known compounds (6 and 7), previously undescribed from P. nitida, have also been purified. The compound isolation workflow was guided by a molecular networking-based dereplication strategy. Twenty-three compounds were dereplicated from the EtOH extract of P. nitida and fractions network and were assigned various levels of identification confidence. The antiparasitic activities against Plasmodium falciparum as well as the cytotoxic activity against the MRC-5 cell line were determined for compounds 1–7.