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Issue 22, 2019
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Leoligin-inspired synthetic lignans with selectivity for cell-type and bioactivity relevant for cardiovascular disease

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Abstract

Recently, a natural compound leoligin, a furan-type lignan, was discovered as an interesting hit compound with an anti-inflammatory pharmacological activity profile. We developed a modular and stereoselective approach for the synthesis of the edelweiss-derived lignan leoligin and used the synthetic route to rapidly prepare leoligin analogs even on the gram scale. Proof of concept of this approach together with cell-based bio-assays gained structural analogs with increased selectivity towards vascular smooth muscle versus endothelial cell proliferation inhibition, a major benefit in fighting vascular neointima formation. In addition, we identified the structural features of leoligin analogs that define their ability to inhibit the pro-inflammatory NF-κB pathway. Results are discussed in the context of structural modification of these novel synthetic lignans.

Graphical abstract: Leoligin-inspired synthetic lignans with selectivity for cell-type and bioactivity relevant for cardiovascular disease

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Supplementary files

Article information


Submitted
25 Jan 2019
Accepted
22 Apr 2019
First published
14 May 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 5815-5820
Article type
Edge Article

Leoligin-inspired synthetic lignans with selectivity for cell-type and bioactivity relevant for cardiovascular disease

T. Linder, R. Liu, A. G. Atanasov, Y. Li, S. Geyrhofer, S. Schwaiger, H. Stuppner, M. Schnürch, V. M. Dirsch and M. D. Mihovilovic, Chem. Sci., 2019, 10, 5815
DOI: 10.1039/C9SC00446G

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