A simple but unusual rearrangement of an oleanane to a taraxerane-28,14 β -olide
Copyright © 2021 Elsevier Inc. All rights reserved..
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.
| Medienart: |
E-Artikel |
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| Erscheinungsjahr: |
2021 |
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| Erschienen: |
2021 |
| Enthalten in: |
Zur Gesamtaufnahme - volume:172 |
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| Enthalten in: |
Steroids - 172(2021) vom: 16. Aug., Seite 108853 |
| Sprache: |
Englisch |
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| Beteiligte Personen: |
Heise, Niels [VerfasserIn] |
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| Links: |
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| Themen: |
6SMK8R7TGJ |
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| Anmerkungen: |
Date Completed 14.01.2022 Date Revised 14.01.2022 published: Print-Electronic Citation Status MEDLINE |
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| doi: |
10.1016/j.steroids.2021.108853 |
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| funding: |
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| Förderinstitution / Projekttitel: |
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| PPN (Katalog-ID): |
NLM324835361 |
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| 245 | 1 | 2 | |a A simple but unusual rearrangement of an oleanane to a taraxerane-28,14 β -olide |
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| 500 | |a Date Revised 14.01.2022 | ||
| 500 | |a published: Print-Electronic | ||
| 500 | |a Citation Status MEDLINE | ||
| 520 | |a Copyright © 2021 Elsevier Inc. All rights reserved. | ||
| 520 | |a 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 | ||
| 650 | 4 | |a Journal Article | |
| 650 | 4 | |a Cytotoxicity | |
| 650 | 4 | |a Oleanolic acid | |
| 650 | 4 | |a Re-arrangement | |
| 650 | 4 | |a Taraxerane | |
| 650 | 7 | |a Antineoplastic Agents |2 NLM | |
| 650 | 7 | |a Triterpenes |2 NLM | |
| 650 | 7 | |a oleanane |2 NLM | |
| 650 | 7 | |a Oleanolic Acid |2 NLM | |
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| 700 | 1 | |a Ströhl, Dieter |e verfasserin |4 aut | |
| 700 | 1 | |a Hoenke, Sophie |e verfasserin |4 aut | |
| 700 | 1 | |a Kazakova, Oxana |e verfasserin |4 aut | |
| 700 | 1 | |a Csuk, René |e verfasserin |4 aut | |
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