Planta Med 2001; 67(5): 437-442
DOI: 10.1055/s-2001-15817
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

Further Phenols and Polyacetylenes from the Rhizomes of Atractylodes lancea and their Anti-Inflammatory Activity[1]

M. Resch1 , J. Heilmann2 , A. Steigel3 , R. Bauer1,*
  • 1 Institut für Pharmazeutische Biologie, Heinrich-Heine-Universität, Düsseldorf, Germany
  • 2 Institut für Pharmazeutische Wissenschaften, ETH Zürich, Switzerland
  • 3 Institut für Organische Chemie und Makromolekulare Chemie, Heinrich-Heine-Universität, Düsseldorf, Germany
Further Information

Publication History

July 11, 2000

November 11, 2000

Publication Date:
31 December 2001 (online)

Abstract

From the rhizomes of Atractylodes lancea, 2-[(2′E)-3′,7′-dimethyl-2′,6′-octadienyl]-4-methoxy-6-methylphenol (1) was isolated as a new natural product. The compound showed strong inhibitory effects on 5-lipoxygenase (5-LOX) and cyclooxygenase-1 (COX-1), but exhibited only weak antioxidative activities [IC50 =0.1 μM (5-LOX), 2 μM (COX-1), 9 μM (PMN/FMLP), 28 μM (PMN/OZ)]. Moreover, five new acetylenes were isolated and elucidated as (3Z,5E,11E)-tridecatriene-7,9-diynyl-1-O-(E)-ferulate (2), erythro-(1,3Z,11E)-tridecatriene-7,9-diyne-5,6-diyl diacetate (3), (1Z)-atractylodin (4), (1Z)-atractylodinol (5), (1Z)-acetylatractylodinol (6) plus the known (4E,6E,12E)-tetradecatriene-8,10-diyne-1,3-diyl diacetate (7). Among the acetylenes, only 2 showed strong inhibition of 5-LOX and COX-1 activity (IC50 (5-LOX)=3 μM, IC50 (COX-1)=1 μM). In addition, the fatty acids linoleic acid, oleic acid and palmitic acid with previously established 5-LOX-/COX-1 inhibitory actions were identified as major constituents of the n-hexane extract and thus seem to contribute to the plant’s in vitro activity.

1 This work is part of the PhD thesis of M. Resch.