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Endogenous metabolites of vitamin E limit inflammation by targeting 5-lipoxygenase. 2018
Helmut Pein, and
Alexia Ville, and
Simona Pace, and
Veronika Temml, and
Ulrike Garscha, and
Martin Raasch, and
Khaled Alsabil, and
Guillaume Viault, and
Chau-Phi Dinh, and
David Guilet, and
Fabiana Troisi, and
Konstantin Neukirch, and
Stefanie König, and
Rosella Bilancia, and
Birgit Waltenberger, and
Hermann Stuppner, and
Maria Wallert, and
Stefan Lorkowski, and
Christina Weinigel, and
Silke Rummler, and
Marc Birringer, and
Fiorentina Roviezzo, and
Lidia Sautebin, and
Jean-Jacques Helesbeux, and
Denis Séraphin, and
Alexander S Mosig, and
Daniela Schuster, and
Antonietta Rossi, and
Pascal Richomme, and
Oliver Werz, and
Andreas Koeberle
Chair of Pharmaceutical/Medicinal Chemistry, Institute of Pharmacy, Friedrich-Schiller-University Jena, 07743, Jena, Germany.
Systemic vitamin E metabolites have been proposed as signaling molecules, but their physiological role is unknown. Here we show, by library screening of potential human vitamin E metabolites, that long-chain ω-carboxylates are potent allosteric inhibitors of 5-lipoxygenase, a key enzyme in the biosynthesis of chemoattractant and vasoactive leukotrienes. 13-((2R)-6-hydroxy-2,5,7,8-tetramethylchroman-2-yl)-2,6,10-trimethyltridecanoic acid (α-T-13'-COOH) can be synthesized from α-tocopherol in a human liver-on-chip, and is detected in human and mouse plasma at concentrations (8-49 nM) that inhibit 5-lipoxygenase in human leukocytes. α-T-13'-COOH accumulates in immune cells and inflamed murine exudates, selectively inhibits the biosynthesis of 5-lipoxygenase-derived lipid mediators in vitro and in vivo, and efficiently suppresses inflammation and bronchial hyper-reactivity in mouse models of peritonitis and asthma. Together, our data suggest that the immune regulatory and anti-inflammatory functions of α-tocopherol depend on its endogenous metabolite α-T-13'-COOH, potentially through inhibiting 5-lipoxygenase in immune cells.
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