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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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
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author 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
author_facet 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
author_sort Kim, Gil Soo
collection PubMed
description 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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spelling pubmed-90338202022-04-26 Jejucarbazoles A–C, carbazole glycosides with indoleamine 2,3-dioxygenase 1 inhibitory activity from Streptomyces sp. KCB15JA151 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 RSC Adv Chemistry 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. The Royal Society of Chemistry 2021-06-01 /pmc/articles/PMC9033820/ /pubmed/35479225 http://dx.doi.org/10.1039/d1ra02895b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
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
Jejucarbazoles A–C, carbazole glycosides with indoleamine 2,3-dioxygenase 1 inhibitory activity from Streptomyces sp. KCB15JA151
title Jejucarbazoles A–C, carbazole glycosides with indoleamine 2,3-dioxygenase 1 inhibitory activity from Streptomyces sp. KCB15JA151
title_full Jejucarbazoles A–C, carbazole glycosides with indoleamine 2,3-dioxygenase 1 inhibitory activity from Streptomyces sp. KCB15JA151
title_fullStr Jejucarbazoles A–C, carbazole glycosides with indoleamine 2,3-dioxygenase 1 inhibitory activity from Streptomyces sp. KCB15JA151
title_full_unstemmed Jejucarbazoles A–C, carbazole glycosides with indoleamine 2,3-dioxygenase 1 inhibitory activity from Streptomyces sp. KCB15JA151
title_short Jejucarbazoles A–C, carbazole glycosides with indoleamine 2,3-dioxygenase 1 inhibitory activity from Streptomyces sp. KCB15JA151
title_sort jejucarbazoles a–c, carbazole glycosides with indoleamine 2,3-dioxygenase 1 inhibitory activity from streptomyces sp. kcb15ja151
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9033820/
https://www.ncbi.nlm.nih.gov/pubmed/35479225
http://dx.doi.org/10.1039/d1ra02895b
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