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Isolation of antiplasmodial anthraquinones from Kniphofia ensifolia, and synthesis and structure-activity relationships of related compounds.

Abstract：

:Bioassay-guided separation of the South African plant Kniphofia ensifolia for antiplasmodial activity led to the isolation of two new anthraquinones, named kniphofiones A and B (3 and 4), together with three known bioactive anthraquinone monomers (1, 2 and 5), and four known bisanthraquinones (6-9). The structures of the two new compounds were elucidated based on analyses of their 1D and 2D NMR spectra and mass spectrometric data. The dimeric compounds 6 and 7 displayed the strongest antiplasmodial activity among all the isolated compounds, with IC₅₀ values of 0.4 ± 0.1 and 0.2 ± 0.1 μM, respectively. The two new compounds displayed modest activities, with IC₅₀ values of 26 ± 4 and 9 ± 1 μM, respectively. Due to the synthetic accessibility of the new compounds and the increased activity shown by the dimeric compounds, a structure-activity relationship study was conducted. As a result, one analogue of kniphofione B (4), the caffeic acid derivative of aloe-emodin, was found to have the highest activity among all the aloe-emodin derivatives, with an IC50 value of 1.3 ± 0.2 μM.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Dai Y,Harinantenaina L,Bowman JD,Da Fonseca IO,Brodie PJ,Goetz M,Cassera MB,Kingston DG

doi

10.1016/j.bmc.2013.11.032

subject

Has Abstract

pub_date

2014-01-01 00:00:00

pages

269-76

issue

1

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(13)00963-2

journal_volume

22

pub_type

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