Multidisciplinary analysis of structurally complex natural products

In recent years an increasing number of natural product structure misassignments have been reported in the literature [1-3], in spite of exceptional advances in spectrometric and spectroscopic instrumentation, in particular of mass spectrometry and nuclear magnetic resonance. In this sense, a major challenge remains to correctly assign the configuration of natural products isolated from various sources [4].
In the course of our biodiscovery program aiming to the isolation of bioactive and structurally unique secondary metabolites from marine invertebrates and from microorganisms, we have faced challenges in structure assignment, specially related to establish the correct configuration of natural products.
In this lecture examples of our recent results will be presented and discussed, illustrating the power of combining “traditional” NMR structure assignment with the use of advanced tools of NMR calculations, bioinformatics genomic analyses and chiroptical analyses.

References
1. Shen, S.-M.; Appendino, G.; Guo, Y.-W. Nat. Prod Rep, 2022, 39, 1803−1832.
2. Chhetri, B. K.; Lavoie, S.; Sweeney-Jones, A. M.; Kubanek, J. Nat. Prod Rep, 2018, 35, 514−531.
3. De León, E. G.; Sánchez-Martínez, H.; Morán-Pinzón, J. A.; Fernández, E. O.; López-Pérez, J. L. J. Nat. Prod. 2023, 86, 897−908.
4. Santos Jr., F. M.; Batista Jr., J. M., in Chiral Separations and Stereochemical Elucidation: Fundamentals, Methods, and Applications, Cass, Q. B.; Tiritan, M. E.; Batista Jr, J. M.; Barreiro, J. C., eds. John Wiley & Sons, Inc., 2023.
Funding: FAPESP, CNPq and CAPS