Synthesis and anti-inflammatory effects of Δ7-Cholestenol and Δ8(14)-Cholestenol derivatives

•We synthesized the O-glycosides of cholesterol derivatives, Δ7-cholestenol and Δ8(14)-cholestenol by Schmidt glycosylation.•1,2,3-triazole-linked N-glycosides of Δ8(14)-cholestenol were prepared by ‘click’ reaction.•Their anti-inflammatory activities were investigated the mRNA expression inhibitory...

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Bibliographic Details
Published in:Steroids 2022-09, Vol.185, p.109043-109043, Article 109043
Main Authors: Moon, Hyejin, Kim, Jungwoog, Yoon, Dowon, Hoon Lee, Tae, Kim, Hakwon
Format: Article
Language:English
Subjects:
Anti-inflammatory
Chemokine
N-glycoside
Δ7-Cholestenol
Δ8-Cholestenol
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Summary:•We synthesized the O-glycosides of cholesterol derivatives, Δ7-cholestenol and Δ8(14)-cholestenol by Schmidt glycosylation.•1,2,3-triazole-linked N-glycosides of Δ8(14)-cholestenol were prepared by ‘click’ reaction.•Their anti-inflammatory activities were investigated the mRNA expression inhibitory activity of CCL17 and CCL22.•1,2,3-triazole-linked N-glycosides of Δ8(14)-cholestenol still showed good anti-inflammatory activity. In this study, O-glycosides of cholesterol derivatives Δ7-cholestenol and Δ8(14)-cholestenol were prepared by Schmidt glycosylation with various glycosyl imidates. In addition, 1,2,3-triazole-linked N-glycosides of Δ8(14)-cholestenol were prepared via the “click” reaction of proparzylic Δ8(14)-cholestenol with glycosyl azides. The anti-inflammatory activities of these molecules were investigated for inhibitory mRNA expression activity of CCL17 and CCL22, which are important biomarkers of atopic dermatitis. Both the O- and N-glycosides Δ7-cholestenol and Δ8(14)-cholestenol were observed to exhibit good anti-inflammatory activity in vitro. In particular, the 1,2,3-triazole-linked N-glycoside of Δ8(14)-cholestenol exhibited anti-inflammatory activity similar to that of O-glycoside in vitro and is expected to be more potent in vivo due to better stability.
ISSN:0039-128X
1878-5867
DOI:10.1016/j.steroids.2022.109043