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A simple but unusual rearrangement of an oleanane to a taraxerane-28,14 β -olide.

Authors
  • Heise, Niels1
  • Siewert, Bianka2
  • Ströhl, Dieter1
  • Hoenke, Sophie1
  • Kazakova, Oxana3
  • Csuk, René4
  • 1 Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany. , (Germany)
  • 2 University of Innsbruck, Institute of Pharmacy/Pharmacognosy, Center for Chemistry and Biomedicine, Innrain 80 - 82, A-6020 Innsbruck, Austria. , (Austria)
  • 3 Ufa Institute of Chemistry UFRC RAS, pr. Octyabrya 71, 450054 Ufa, Russian Federation. , (Russia)
  • 4 Martin-Luther-University Halle-Wittenberg, Organic Chemistry, Kurt-Mothes-Str. 2, D-06120 Halle (Saale), Germany. Electronic address: [email protected] , (Germany)
Type
Published Article
Journal
Steroids
Publication Date
Apr 27, 2021
Volume
172
Pages
108853–108853
Identifiers
DOI: 10.1016/j.steroids.2021.108853
PMID: 33930390
Source
Medline
Keywords
Language
English
License
Unknown

Abstract

Reaction of 3-O-acetyl-oleanolic acid (3) with formic acid/hydrogen peroxide at 100 °C for several hours provides an extraordinary but simple pathway to a taraxeran-28,14 β -olide type triterpenoid while the same reaction at 0 °C occurred without re-arrangement of the carbon skeleton, and an oleanane-28,13 β -olide was obtained instead. The products from these reactions were subjected to a cytotoxicity screening employing several human tumor cell lines showing the latter compound not cytotoxic while the former was cytotoxic especially for MCF-7 (breast adenocarcinoma), and FaDu (hypopharyngeal carcinoma) cells. The highest cytotoxicity, however, was observed for 3 β, 12α, 13 β -trihydroxy-oleanan-28-oic acid (6) holding with EC50 = 4.2 μM for MCF-7 tumor cells. Copyright © 2021 Elsevier Inc. All rights reserved.

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