Computational Structural Revision of Elaeophorbate and Other Triterpenoids with the Help of NAPROC-13. A New Strategy for Structural Revision of Natural Products

A considerable number of natural products have been published in recent years with misassigned structure, even though they had been correctly elucidated in the past. The availability of databases containing revised structures can prevent the amplification of errors in structural elucidation. NAPROC-13, a dereplication tool based on the 13C chemical shift, has been used to search for substances that, possessing the same chemical shifts, have been described with different structures. The correct structure of these different structural proposals is verified by computational chemistry. This paper reports the structural revision of nine triterpenoids following this methodology.

Automated summary

In recent years, a significant number of natural products have been published with incorrectly assigned structures, despite having been previously correctly elucidated. The availability of databases containing revised structures can help prevent the spread of errors in structural elucidation. A dereplication tool called NAPROC-13, based on 13C chemical shift, has been used to identify substances that have been described with different structures but possess the same chemical shifts. Computational chemistry is employed to verify the correct structure among these proposed different structures. This paper presents the structural revision of nine triterpenoids using this methodology.