Digitizing historical collections of natural products to further explore the monoterpene indole alkaloids chemical space

Monoterpene indole alkaloids (MIAs) constitute a broad class of nitrogen-containing plant-derived natural products composed of more than 3000 members.[1] This natural product class is found in hundreds of plant species from the Apocynaceae, Loganiaceae, Rubiaceae, Icacinaceae, Nyssaceae, and Gelsemiaceae plant families. Throughout the six past decades, the structural intricacies and biological activities of these molecules have captured the interest of many researchers all over the world.

As part of our continuing interest in MIA chemistry, we recently implemented an in-house MS/MS database, constituted of a cumulative collection of alkaloids from the global natural products research community. These endeavors led to the construction of the largest MS/MS dataset of MIAs to date, that we named: Monoterpene Indole Alkaloids DataBase (MIADB).[2] Thanks to this database, we developed a streamlined molecular networking dereplication pipeline directed toward the reinvestigation of previously studied MIA-containing plants. This pipeline allowed to prioritize the isolation workflow toward new alkaloids bearing unprecedented carbon skeleton and interesting biological activities. This presentation is intended to describe the most significant results gleaned from the reinvestigation of several forgotten plants by this new generation of sophisticated tools.

Fig. 1

• References

• 1 Pan Q, Mustafa NR, Tang K, Choi YH, Verpoorte R. Monoterpenoid indole alkaloids biosynthesis and its regulation in Catharanthus roseus: a literature review from genes to metabolites. Phytochemistry Rev 2016; 15: 221-250.
• 2 Fox Ramos AE, Le Pogam P, Fox Alcover C, Otogo N’Nang E, Cauchie G, Hazni H. et al. Collected mass spectrometry data on monoterpene indole alkaloids from natural product chemistry research. Sci Data 2019; 6: 15.