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

Negera Abdissa, Matthias Heydenreich, Jacob O. Midiwo, Albert Ndakala, Zs. Majer, Beate Neumann, Hans Georg Stammler, Norbert Sewald, Abiy Yenesew

Research output: Contribution to journalArticle

7 Citations (Scopus)

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 μM). 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 μM, respectively).

Original languageEnglish
Pages (from-to)67-73
Number of pages7
JournalPhytochemistry Letters
Volume9
Issue number1
DOIs
Publication statusPublished - 2014

Fingerprint

Xanthones
xanthone
xanthones
Anthraquinones
anthraquinones
inhibitory concentration 50
Inhibitory Concentration 50
cervix
methylene chloride
carboxylic acids
Mannich Bases
Oxazines
X-ray diffraction
spectral analysis
phytopharmaceuticals
carcinoma
cytotoxicity
methanol
chemical derivatives
Methylene Chloride

Keywords

  • Bulbine frutescens
  • Cytotoxicity
  • Phenylanthraquinone
  • seco-Anthraquinone
  • Structure revision
  • Xanthone

ASJC Scopus subject areas

  • Plant Science
  • Agronomy and Crop Science
  • Biochemistry
  • Biotechnology

Cite this

A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones. / Abdissa, Negera; Heydenreich, Matthias; Midiwo, Jacob O.; Ndakala, Albert; Majer, Zs.; Neumann, Beate; Stammler, Hans Georg; Sewald, Norbert; Yenesew, Abiy.

In: Phytochemistry Letters, Vol. 9, No. 1, 2014, p. 67-73.

Research output: Contribution to journalArticle

Abdissa, Negera ; Heydenreich, Matthias ; Midiwo, Jacob O. ; Ndakala, Albert ; Majer, Zs. ; Neumann, Beate ; Stammler, Hans Georg ; Sewald, Norbert ; Yenesew, Abiy. / A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones. In: Phytochemistry Letters. 2014 ; Vol. 9, No. 1. pp. 67-73.
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