Density functional theory-nuclear magnetic resonance-validated full structure elucidation of theionbrunonine C, an unstable N-oxide theionbrunonine from Mostuea brunonis.
Magn Reson Chem
; 60(12): 1178-1184, 2022 12.
Article
em En
| MEDLINE
| ID: mdl-35368097
ABSTRACT
The structure elucidation of theionbrunonine C, a thioether-bridged dimeric monoterpene indole alkaloid (MIA), and more generally, one of the very few sulfur-containing MIA, is reported after its isolation from Mostuea brunonis (Gelsemiaceae). This unstable structure had already been targeted for isolation in our former, molecular network-guided, investigation of this plant, but this compound had degraded before sufficient spectroscopic data could have been acquired for a complete structure assignment. With this constraint in mind, the rapid acquisition of nuclear magnetic resonance (NMR) data enabled retrieving sufficient spectroscopic information for full structure elucidation, although from a partial set of spectroscopic information (1 H and 13 C NMR; COSY, HSQC, and HMBC). In conjunction with biosynthetic considerations, the cursory examination of 13 C NMR data unambiguously defined the complete stereostructure of 1, as further supported by density functional theory (DFT)-NMR calculations and subsequent DP4 probability score.
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Base de dados:
MEDLINE
Assunto principal:
Óxidos
/
Alcaloides Indólicos
Idioma:
En
Ano de publicação:
2022
Tipo de documento:
Article