Combination of Machine Learning and Empirical Computation for the Structural Validation of Trirosaline, a Natural Trimeric Monoterpene Indole Alkaloid from Catharanthus roseus.
Org Lett
; 26(1): 274-279, 2024 01 12.
Article
em En
| MEDLINE
| ID: mdl-38134219
ABSTRACT
Chemical investigation of the emblematic Catharanthus roseus led to the discovery of trirosaline (1), the first example of a tris-ajmalicine-type monoterpene indole alkaloid and the first natural trimeric MIA ever reported from this deeply dug plant species. Its structure was primarily elucidated based on NMR and HRESIMS analyses, and the nature of its unique intermonomeric linkages was firmly confirmed based on a combination of empirical computation and ML-J-DP4 study. Its absolute configuration was mitigated by comparison of experimental and TDDFT-simulated electronic circular dichroism (ECD) spectra. A possible biosynthetic pathway for trirosaline (1) was postulated.
Texto completo:
1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Catharanthus
/
Alcaloides de Triptamina e Secologanina
Idioma:
En
Revista:
Org Lett
Ano de publicação:
2024
Tipo de documento:
Article