New Sesquiterpene Lactones from Laurus nobilis Leaves as Inhibitors of Nitric Oxide Production

Abstract

Two new metabolites 5αH,7αH-eudesman-4α,6α,11,12-tetraol (1) and 1β,15-dihydroxy-5αH,7αH-eudesma-3,11(13)-dien-12,6α-olide (2) have been isolated from the methanolic extract of Laurus nobilis L. leaves. Their structures were determined through analysis of their one- and two-dimensional NMR spectral data (¹H- and ¹³C-NMR, DEPT, COSY, HMQC, HMBC and ROESY). The relative stereochemistry is proposed on the basis of combined J-based configuration analysis and ROESY data. In addition, three known sesquiterpene lactones santamarine (3), reynosin (4) and costunolide (5) along with blumenol C (6) were isolated and identified by spectral means. The isolated compounds 1 - 6 were found to inhibit nitric oxide (NO) production in lipopolysaccharide (LPS)-activated murine macrophages. The most active compound 2 potently inhibited NO₂ ^- release with an IC₅₀ value of 0.8 μM.

Laurus nobilis - Lauraceae - sesquiterpenoids - eudesmane - costunolide - nitric oxide

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