A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones
| Autor: | Beate Neumann, Abiy Yenesew, Hans-Georg Stammler, Zsuzsanna Majer, Negera Abdissa, Matthias Heydenreich, Norbert Sewald, Albert Ndakala, Jacob O. Midiwo |
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| Jazyk: | angličtina |
| Rok vydání: | 2014 |
| Předmět: |
Phenylanthraquinone knipholone
biology Stereochemistry Cytotoxicity Knipholone seco-Anthraquinone Phenylanthraquinone Plant Science Mannich base Xanthone biology.organism_classification Biochemistry chemistry.chemical_compound chemistry Phytochemical Structure revision Anthraquinones Institut für Chemie Bulbine frutescens Agronomy and Crop Science Biotechnology Dichloromethane |
| Popis: | Phytochemical investigation of the dichloromethane/methanol (1:1) extract of the roots of Bulbine frutescens led to the isolation of a new xanthone, 8-hydroxy-6-methylxanthone-1-carboxylic acid (1) and a new phenylanthraquinone, 6',8-O-dimethylknipholone (2) along with six known compounds. The structures were elucidated on the basis of NMR and MS spectral data analyses. The structure of compound 1 was confirmed through X-ray crystallography which was then used as a reference to propose the revision of the structures of six seco-anthraquinones into xanthones. The isolated compounds were evaluated for cytotoxicity against human cervix carcinoma KB-3-1 cells with the phenylanthraquinone knipholone being the most active (IC50 = 0.43 mu M). Two semi-synthetic knipholone derivatives, knipholone Mannich base and knipholone-1,3-oxazine, were prepared and tested for cytotoxic activity; both showed moderate activities (IC50 value of 1.89 and 2.50 mu M, respectively). (C) 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved. |
| Databáze: | OpenAIRE |
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