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来自KCB15JA151菌株的具有吲哚胺2,3-双加氧酶1抑制活性的咔唑糖苷类化合物Jejucarbazoles A-C。

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

作者信息

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

机构信息

Anticancer Agent Research Center, Korea Research Institute of Bioscience and Biotechnology Cheongju 28116 Korea

Department of Biomolecular Science, KRIBB School of Bioscience, University of Science and Technology Daejeon 34113 Korea.

出版信息

RSC Adv. 2021 Jun 1;11(32):19805-19812. doi: 10.1039/d1ra02895b. eCollection 2021 May 27.

DOI:10.1039/d1ra02895b
PMID:35479225
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9033820/
Abstract

A bioassay-guided investigation led to the isolation of three new carbazole glycosides, jejucarbazoles A-C (1-3), from 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 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.

摘要

通过生物活性导向研究，从 sp. KCB15JA151 中分离出三种新的咔唑糖苷，即空肠咔唑 A - C（1 - 3）。通过详细的核磁共振（NMR）和质谱（MS）光谱分析以及文献研究阐明了它们的平面结构。通过旋转 Overhauser 效应光谱（ROESY）相关、耦合常数、硫代氨基甲酰 - 噻唑烷羧酸酯衍生物的液相色谱 - 质谱（LC - MS）分析以及电子圆二色光谱（ECD）计算确定了它们的相对和绝对构型。化合物 1 - 3 表现出对吲哚胺 2,3 - 双加氧酶 1（IDO1）的抑制活性，IC 值分别为 18.38、9.17 和 8.81 μM。分子对接分析表明，所有化合物均作为血红素置换抑制剂作用于 IDO1 酶。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/94b6/9033820/d81f76b90075/d1ra02895b-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/94b6/9033820/84d5e1b82581/d1ra02895b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/94b6/9033820/c9870492b85b/d1ra02895b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/94b6/9033820/d95f7de447c7/d1ra02895b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/94b6/9033820/61787d74914d/d1ra02895b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/94b6/9033820/d81f76b90075/d1ra02895b-f5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/94b6/9033820/84d5e1b82581/d1ra02895b-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/94b6/9033820/c9870492b85b/d1ra02895b-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/94b6/9033820/d95f7de447c7/d1ra02895b-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/94b6/9033820/61787d74914d/d1ra02895b-f4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/94b6/9033820/d81f76b90075/d1ra02895b-f5.jpg

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