Jejucarbazoles A–C, carbazole glycosides with indoleamine 2,3-dioxygenase 1 inhibitory activity from Streptomyces sp. KCB15JA151

A bioassay-guided investigation led to the isolation of three new carbazole glycosides, jejucarbazoles A–C (1–3), from Streptomyces sp. KCB15JA151. Their planar structures were elucidated by detailed NMR and MS spectroscopic analysis with a literature study. Their relative and absolute configuration...

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Detalles Bibliográficos
Autores principales: Kim, Gil Soo, Jang, Jun-Pil, Kwon, Mincheol, Oh, Tae Hoon, Heo, Kyung Taek, Lee, Byeongsan, Lee, Jung-Sook, Ko, Sung-Kyun, Hong, Young-Soo, Ahn, Jong Seog, Jang, Jae-Hyuk
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2021
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9033820/
https://www.ncbi.nlm.nih.gov/pubmed/35479225
http://dx.doi.org/10.1039/d1ra02895b
Descripción
Sumario:A bioassay-guided investigation led to the isolation of three new carbazole glycosides, jejucarbazoles A–C (1–3), from Streptomyces sp. KCB15JA151. Their planar structures were elucidated by detailed NMR and MS spectroscopic analysis with a literature study. Their relative and absolute configurations were established by ROESY correlations, coupling constants, LC-MS analysis of thiocarbamoyl-thiazolidine carboxylate derivatives, and ECD calculation. Compounds 1–3 showed indoleamine 2,3-dioxygenase 1 (IDO1) inhibitory activity with IC(50) values of 18.38, 9.17, and 8.81 μM. The molecular docking analysis suggested that all compounds act as heme-displacing inhibitors against IDO1 enzyme.

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