Issue 7, 2024, Issue in Progress

Role of the thiosugar ring in the inhibitory activity of salacinol, a potent natural α-glucosidase inhibitor

Abstract

Herein, ring-cleaved (24) and truncated (25) analogues of an azasugar, 1-deoxynojirimycin (23), exhibited inhibitory activity (Ki = 4–10 μM) equal to that of the parent compound (1, Ki = 14 μM). Based on this structure–activity relationship (SAR), four ring-cleaved (26a–26c and 27c) and three truncated (28a–28c) analogues of salacinol (1), a potent thiosugar-ring-containing α-glucosidase inhibitor, were synthesised. Bioassay results revealed that all the synthetics were inactive, indicating that the 5-membered thiosugar ring of 1 played an essential role in the potent activities of sulfonium-type inhibitors. The present findings are interesting and important in understanding the function of salacinol, considering that the observed inhibitory activity trend was contrary to the SAR observed in aza-compounds (23, 24, and 25) in a previous study, which suggested that the cyclic structure did not contribute to their strong inhibitory activity.

Graphical abstract: Role of the thiosugar ring in the inhibitory activity of salacinol, a potent natural α-glucosidase inhibitor

Supplementary files

Transparent peer review

To support increased transparency, we offer authors the option to publish the peer review history alongside their article.

View this article’s peer review history

Article information

Article type
Paper
Submitted
12 Dec 2023
Accepted
23 Jan 2024
First published
02 Feb 2024
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2024,14, 4471-4481

Role of the thiosugar ring in the inhibitory activity of salacinol, a potent natural α-glucosidase inhibitor

K. Takashima, S. Nakamura, M. Nagayama, S. Marumoto, F. Ishikawa, W. Xie, I. Nakanishi, O. Muraoka, T. Morikawa and G. Tanabe, RSC Adv., 2024, 14, 4471 DOI: 10.1039/D3RA08485J

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements