Antiplasmodial Quinones from the Rhizomes of Kniphofia Foliosa

Extracts of the rhizomes of Kniphofia foliosa exhibited antiplasmodial activities against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum with IC50 values of 3–5 μg/mL. A phenyloxanthrone, named 10-acetonylknipholone cyclooxanthrone (1) and an anthraquinone-anthrone dimer, chryslandicin 10-methyl ether (2), were isolated from the rhizomes, along with known quinones, including the rare phenylanthraquinone dimers, joziknipholones A and B. The structures of these compounds were determined based on spectroscopic data. This is the second report on the occurrence of the dimeric phenylanthraquinones in nature. In an in vitro antiplasmodial assay of the isolated compounds, activity was observed for phenylanthraquinones, anthraquinone-anthrone dimers and dimeric phenylanthraquinones, with joziknipholone A being the most active. The new compound, 10-acetonylknipholone cyclooxanthrone, also showed anti-plasmodial activity. In an in vivo assay, knipholone anthrone displayed marginal antimalarial activity.

[1]  M. Heydenreich,et al.  Knipholone cyclooxanthrone and an anthraquinone dimer with antiplasmodial activities from the roots of Kniphofia foliosa , 2013 .

[2]  V. Lipipun,et al.  Neolignans from leaves of Miliusa mollis. , 2013, Fitoterapia.

[3]  A. Yenesew,et al.  Naphthoquinones from the roots of Aloe secundiflora , 2012 .

[4]  N. Waters,et al.  The antiplasmodial and radical scavenging activities of flavonoids of Erythrina burttii. , 2012, Acta tropica.

[5]  Kirandeep Kaur,et al.  Antimalarials from nature. , 2009, Bioorganic & medicinal chemistry.

[6]  G. Bringmann,et al.  Knipholone and related 4-phenylanthraquinones: structurally, pharmacologically, and biosynthetically remarkable natural products. , 2008, Natural product reports.

[7]  M. Heydenreich,et al.  Joziknipholones A and B: the first dimeric phenylanthraquinones, from the roots of Bulbine frutescens. , 2008, Chemistry.

[8]  S. Habtemariam.  Antioxidant activity of Knipholone anthrone , 2007 .

[9]  R. Bauer,et al.  Knipholone, a selective inhibitor of leukotriene metabolism. , 2006, Phytomedicine : international journal of phytotherapy and phytopharmacology.

[10]  S. Croft,et al.  Antimalarial compounds from Kniphofia foliosa roots , 2005, Phytotherapy research : PTR.

[11]  Niresh Bhagwandin,et al.  In vitro antiplasmodial activity of medicinal plants native to or naturalised in South Africa. , 2004, Journal of ethnopharmacology.

[12]  V. Karunaratne,et al.  Antimicrobial alkaloids from Zanthoxylum tetraspermum and caudatum. , 2001, Phytochemistry.

[13]  Michael Müller,et al.  An anthrone, an anthraquinone and two oxanthrones from Kniphofia foliosa , 1994 .

[14]  M. Adinolfi,et al.  A new class of anthraquinone-anthrone-C-glycosides from asphodelus ramosus tubers. , 1991 .

[15]  W. Steglich,et al.  New bianthraquinone pigments from kniphofia species , 1987 .

[16]  M. Fetene,et al.  Anthraquinones as taxonomic markers in ethiopian Kniphofia species , 1986 .

[17]  E. Dagne,et al.  Aloe-Emodin Acetate, an Anthraquinone Derivative from Leaves of Kniphofia foliosa , 1984, Planta medica.

[18]  W. Peters,et al.  The chemotherapy of rodent malaria, XXIII Causal prophylaxis, part II: Practical experience with Plasmodium yoelii nigeriensis in drug screening. , 1975, Annals of tropical medicine and parasitology.

[19]  K. Makino,et al.  Studies on the Constituents of Aloe sapnaria HAW. I. The Structures of Tetrahydroanthracene Derivatives and the Related Anthraquinones , 1974 .