A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones

Abdissa N, Heydenreich M, Midiwo JO, Ndakala A, Majer Z, Neumann B, Stammler H-G, Sewald N, Yenesew A (2014)
Phytochemistry Letters 9: 67-73.

Journal Article | Published | English

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Abstract
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.
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Abdissa N, Heydenreich M, Midiwo JO, et al. A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones. Phytochemistry Letters. 2014;9:67-73.
Abdissa, N., Heydenreich, M., Midiwo, J. O., Ndakala, A., Majer, Z., Neumann, B., Stammler, H. - G., et al. (2014). A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones. Phytochemistry Letters, 9, 67-73.
Abdissa, N., Heydenreich, M., Midiwo, J. O., Ndakala, A., Majer, Z., Neumann, B., Stammler, H. - G., Sewald, N., and Yenesew, A. (2014). A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones. Phytochemistry Letters 9, 67-73.
Abdissa, N., et al., 2014. A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones. Phytochemistry Letters, 9, p 67-73.
N. Abdissa, et al., “A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones”, Phytochemistry Letters, vol. 9, 2014, pp. 67-73.
Abdissa, N., Heydenreich, M., Midiwo, J.O., Ndakala, A., Majer, Z., Neumann, B., Stammler, H.-G., Sewald, N., Yenesew, A.: A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones. Phytochemistry Letters. 9, 67-73 (2014).
Abdissa, Negera, Heydenreich, Matthias, Midiwo, Jacob O., Ndakala, Albert, Majer, Zsuzsanna, Neumann, Beate, Stammler, Hans-Georg, Sewald, Norbert, and Yenesew, Abiy. “A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones”. Phytochemistry Letters 9 (2014): 67-73.
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