Bisabolane sesquiterpenes from the leaves of Lindera benzoin reduce prostaglandin E2 formation in A549 cells

• Published in: Phytochemistry letters Vol. 38; pp. 6 - 11
• Main Authors: Henz Ryen, Astrid, Göls, Thomas, Steinmetz, Julia, Tahir, Ammar, Jakobsson, Per-Johan, Backlund, Anders, Urban, Ernst, Glasl, Sabine
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 01.08.2020
• Subjects: Anti-inflammatory; Lindera benzoin; Medicin och hälsovetenskap; Prostaglandin E2; Sesquiterpenes; Structure elucidation; Prostaglandin E2; Lindera benzoin; Structure elucidation; Anti-inflammatory; Sesquiterpenes
• ISSN: 1874-3900; 1876-7486; 1876-7486
• DOI: 10.1016/j.phytol.2020.04.015

[Display omitted] •Three new bisabolane sesquiterpenes were isolated from Lindera benzoin.•Their structure elucidation was achieved via MS and extensive NMR measurements.•Anti-inflammatory properties of the isolated bisabolane sesquiterpenes were studied.•A significant reduction of pro-inflammatory prostaglandin E2 formation in A549 cells was observed. Phytochemical investigation of leaves from the American shrub Lindera benzoin (L.) Blume (Lauraceae) resulted in the isolation of one pure compound 1 and a diastereomeric mixture of 2 and 3. The structures of these new bisabolane sesquiterpenes were elucidated via MS and extensive NMR measurements and identified as 6-(2-hydroxy-6-methylhept-5-en-2-yl)-3-(hydroxymethyl)-4-oxocyclohex-2-en-1-yl acetate (1) and 3-(hydroxymethyl)-6-(5-(2-hydroxypropan-2-yl)-2-methyltetrahydrofuran-2-yl)-4-oxocyclohex-2-en-1-yl acetate (2 and 3). The compounds were evaluated in vitro for their anti-inflammatory activity. In cellular assays, 1-3 reduced pro-inflammatory prostaglandin E2 production in A549 cells in a dose-dependent manner.