Revisiting Previously Investigated Plants: A Molecular Networking-Based Study of Geissospermum laeve

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Fox Ramos A.E.
Alcover C.
Evanno L.
Maciuk A.
Litaudon M.
Duplais C.
Bernadat G.
Gallard J.-F.
Jullian J.-C.
Mouray E.
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American Chemical Society
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Three new monoterpene indole alkaloids (1–3) have been isolated from the bark of Geissospermum laeve, together with the known alkaloids (−)-leuconolam (4), geissolosimine (5), and geissospermine (6). The structures of 1–3 were elucidated by analysis of their HRMS and NMR spectroscopic data. The absolute configuration of geissolaevine (1) was deduced from the comparison of experimental and theoretically calculated ECD spectra. The isolation workflow was guided by a molecular networking-based dereplication strategy using an in-house database of monoterpene indole alkaloids. In addition, five known compounds previously undescribed in the Geissospermum genus were dereplicated from the G. laeve alkaloid extract network and were assigned with various levels of identification confidence. The antiparasitic activities against Plasmodium falciparum and Leishmania donovani as well as the cytotoxic activity against the MRC-5 cell line were determined for compounds 1–5.
This work has been developed with the funding from Cienciactiva, an initiative of the National Council for Science, Technology and Technological Innovation (CONCYTEC) contract 239-2015-FONDECYT. In addition, this work was also supported by the French ANR grant ANR-15-CE29-0001. We express our thanks to Dr. J. Bignon (ICSN) for performing the cytotoxic assays. We also thank K. Leblanc (BioCIS) for her assistance in the preparative HPLC purifications. We are grateful to Dr. M. Wang, Prof. P. Dorrestein, and Prof. N. Bandeira (University of California, San Diego) for developing and making public the GNPS platform.
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leuconolam, antiparasitic agent, geissolosimine, geissospermine, Geissospermum laeve alkaloid extract, indole alkaloid