Two new anti-plasmodial flavonoid glycosides from Duranta repens.
The CHCl(3)-soluble fraction of the whole plant of Duranta repens showed anti-plasmodial activity against the chloroquine-sensitive (D6) and chloroquine-resistant (W2) strains of Plasmodium falciparum, with IC(50) values of 8.5 ± 0.9 and 10.2 ± 1.5 μg/mL, respectively. From this fraction, two new flavonoid glycosides, 7-O-α-d-glucopyranosyl-3,4'-dihydroxy-3'-(4-hydroxy-3-methylbutyl)-5,6-dimethoxyflavone (1) and 7-O-α-d-glucopyranosyl(6'''-p-hydroxcinnamoyl)-3,4'-dihydroxy-3'-(4-hydroxy-3-methylbutyl)-5,6-dimethoxyflavone (2), along with five known flavonoids, 3,7,4'-trihydroxy-3'-(4-hydroxy-3-methylbutyl)-5,6-dimethoxyflavone (3), 3,7-dihydroxy-3'-(4-hydroxy-3-methylbutyl)-5,6,4'-trimethoxyflavone (4), 5,7-dihydroxy-3'-(2-hydroxy-3-methyl-3-butenyl)-3,6,4'-trimethoxyflavone (5), 3,7-dihydroxy-3'-(2-hydroxy-3-methyl-3-buten-yl)-5,6,4'-trimethoxyflavone (6), and 7-O-α-d-glucopyranosyl-3,5-dihydroxy-3'-(4''-acetoxy-3''-methylbutyl)-6,4'-dimethoxyflavone (7), have been isolated as anti-plasmodial principles. Their structures were deduced by spectroscopic analysis including 1D and 2D NMR techniques. The compounds (1-7) showed potent anti-plasmodial activities against D6 and W2 strains of Plasmodium falciparum, with IC(50) values in the range of 5.2-13.5 μM and 5.9-13.1 μM, respectively.
Ijaz
Fozia
F
Kohat Institute of Medical Sciences, Kohat University of Science and Technology, Kohat, N.W.F.P., Pakistan.
Ahmad
Nisar
N
Ahmad
Ijaz
I
ul Haq
Azhar
A
Wang
Fanghai
F
D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D055808:Drug Discovery; D004351:Drug Resistance; D005419:Flavonoids / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D020128:Inhibitory Concentration 50; D016778:Malaria, Falciparum / Q000188:drug therapy; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology; D010963:Plasmodium falciparum / Q000187:drug effects*; D029648:Verbenaceae / Q000737:chemistry*
C556601:7-O-alpha-D-glucopyranosyl(6'''-p-hydroxcinnamoyl)-3,4'-dihydroxy-3'-(4-hydroxy-3-methylbutyl)-5,6-dimethoxyflavone; C556600:7-O-alpha-D-glucopyranosyl-3,4'-dihydroxy-3'-(4-hydroxy-3-methylbutyl)-5,6-dimethoxyflavone; D000962:Antimalarials; D005419:Flavonoids; D006027:Glycosides; D010936:Plant Extracts