Stereochemical Analysis of Natural Products: Bisindole Alkaloids of the Strychnos-Strychnos Type

monomeric and dimeric indole alkaloids of Strychnos type- stereochemistry- conformational analysis-; 1 H and 13 C NMR computational analysis -DFT (Density Functional Theory) calculations

Abstract :

[en] Results of the high-level computational study of 12 bisindole alkaloids of the Strychnos-Strychnos type are reported in addition of that of five retuline-like monomers frequently encountered in moieties constituting dimeric alkaloids. Based on the comparison of theoretical and experimental NMR chemical shifts, a detailed conformational survey of these stereochemically rich natural products containing multiple asymmetric centers was performed. Our original methodology is based on searching multiple conformational states, geometry optimization, and high-level NMR calculations at the DFT level. Taking into account all known experimental chemical shifts together with their calculated values in the natural products under study, a correlation estimate of NMR chemical shifts was performed by using statistical descriptors. In general, a good agreement of the performed calculations with experiment was achieved, which is manifested by the Corrected Mean Absolute Error of about 0.2 ppm for 1H and 1.9 ppm for 13C NMR chemical shifts in this series.

Research Center/Unit :

Center of Interdiciplinary Research on Medicines, Faculty of Medicine, University of Liège ( Lab. of Pharmacognosy)-

Disciplines :

Chemistry
Biochemistry, biophysics & molecular biology

Author, co-author :

Grigoriev, Dmitry A.; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky St. 1, 664033 Irkutsk, Russia

Semenov, Valentin A. ; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky St. 1, 664033 Irkutsk, Russia

Angenot, Luc ; Université de Liège - ULiège > Département de pharmacie

Krivdin, Leonid B. ; A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, Favorsky St. 1, 664033 Irkutsk, Russia

Language :

English

Title :

Stereochemical Analysis of Natural Products: Bisindole Alkaloids of the Strychnos-Strychnos Type

Publication date :

28 December 2025

Journal title :

International Journal of Molecular Sciences

ISSN :

1661-6596

eISSN :

1422-0067

Publisher :

MDPI AG

Volume :

Issue :

Pages :

337 (24 pages)

Peer reviewed :

Peer Reviewed verified by ORBi

Additional URL :

https://www.mdpi.com/1422-0067/27/1/337/pdf

Available on ORBi :

since 02 January 2026

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