Anti-malarial natural and synthetic bromopyrrole alkaloids

One project whose results were published in 2018 and has not been mentioned here was the discovery of anti-malarial activity of pseudoceratidine and synthetic derivatives. This project started some years ago when a MSc student Ivan Severo started to work on a sample of the sponge Tedania brasiliensis, endemic to Brazil, and isolated pseudoceratidine. Unfortunately Ivan left the group before finishing his MSc dissertation. Afterwards, a new PhD student, Lorena Parra, took the project and developed it with great enthusiasm. Lorena did a very fine and careful isolation work and discovered a series of pseudoceratidine derivatives with varied bromination at the pyrrole groups. She also discovered unprecedented modified pseudoceratidine derivatives that we named tedamides. When the first results of bioassays were available, a new PhD student joined the group, Ariane Bertonha. Ariane had a previous experience on organic synthesis during her MSc degree. We then agreed for her to develop a project on the synthesis of pseudoceratidine derivatives in collaboration with Professor Daniel Romo’s group at Baylor University. Ariane was awarded with a Science without Borders scholarship to spend 11 months at Professor Romo’s group, where she prepared 20 pseudoceratidine derivatives. This collaboration was extremely fruitful after we got the complete results of bioassays performed by Dr. Danilo C. Miguel (on anti-Leishmanial activity, Biology Institute at UNICAMP), Prof. Fernanda Gadelha (on anti-Trypanosoma cruzi activity, Biology Institute at UNICAMP) and Prof. Rafael Guido (on anti-malarial activity, Physics Institute at São Carlos, USP). This was a true interdisciplinary project involving natural products chemistry, synthetic chemistry and biology, thanks to the great team involved. We are particularly grateful to Professor Daniel Romo for hosting Ariane at his group. The results have been reported in a paper published last year in the Journal of Natural Products. If you are interested in the article, please read it and check the Supplementary Material including isolation and synthesis data.

This is Tedania brasiliensis, a beautiful red-pink sponge with large oscula. The photo was taken by our sponge taxonomy collaborator Professor Eduardo Hajdu (Museu Nacional, UFRJ)