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Caulerpenyne and Related Bis‐enol Esters Are Novel‐Type Inhibitors of Human 5‐Lipoxygenase |
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| Authors: | Phillipp Richter Gregor Schubert Anja Maria Schaible Prof. Dr. Levent Cavas Prof. Dr. Oliver Werz Prof. Dr. Georg Pohnert |
| Affiliation: | 1. Friedrich Schiller University Jena, Institute for Inorganic and Analytical Chemistry, Bioorganic Analytics, Lessingstra?e 8, 07743 Jena (Germany);2. Friedrich Schiller University Jena, Chair of Pharmaceutical/Medicinal Chemistry, Philosophenweg 14, 07743 Jena (Germany);3. Dokuz Eylül University, Faculty of Sciences, Department of Chemistry, Tinaztepe Campus, 35160 ?zmir (Turkey) |
| Abstract: | Caulerpenyne (CYN) is a sesquiterpene from green algae with known inhibitory properties against soybean lipoxygenase. Here we introduce a detailed structure–activity study elucidating the inhibitory effects of CYN and a library of six synthetic CYN analogues on isolated human 5‐lipoxygenase (5‐LO) and cellular 5‐LO in polymorphonuclear leukocytes. Essential structural elements are identified and a structurally simplified inhibitor is introduced. The modes of 5‐LO inhibition by CYN and the synthetic inhibitors cannot be assigned to any of the known categories of lipoxygenase inhibitors. These compounds clearly interfere directly with 5‐LO and represent rather small and flexible molecules, with unique structures among 5‐LO inhibitors identified thus far. |
| Keywords: | caulerpenyne inhibition lipoxygenase structure activity synthetic analogues |