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Issue 90, 2018
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Structure-inspired design of a sphingolipid mimic sphingosine-1-phosphate receptor agonist from a naturally occurring sphingomyelin synthase inhibitor

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Abstract

Ginkgolic acid obtained as a sphingomyelin synthase inhibitor from a plant extract library inspired the concept of sphingolipid mimics. Ginkgolic acid-derived N-acyl anilines and ginkgolic acid 2-phosphate (GA2P) respectively mimic ceramide and sphingosine 1-phosphate (S1P) in structure and function. The GA2P-induced phosphorylation of ERK and internalization of S1P receptor 1 (S1P1) indicated potent agonist activity. Docking studies revealed that GA2P adopts a similar binding conformation to the bound ligand ML5, which is a strong antagonist of S1P1.

Graphical abstract: Structure-inspired design of a sphingolipid mimic sphingosine-1-phosphate receptor agonist from a naturally occurring sphingomyelin synthase inhibitor

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Publication details

The article was received on 11 Jul 2018, accepted on 14 Oct 2018 and first published on 16 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC05595E
Citation: Chem. Commun., 2018,54, 12758-12761
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    Structure-inspired design of a sphingolipid mimic sphingosine-1-phosphate receptor agonist from a naturally occurring sphingomyelin synthase inhibitor

    M. M. M. Swamy, Y. Murai, Y. Ohno, K. Jojima, A. Kihara, S. Mitsutake, Y. Igarashi, J. Yu, M. Yao, Y. Suga, M. Anetai and K. Monde, Chem. Commun., 2018, 54, 12758
    DOI: 10.1039/C8CC05595E

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