Flavonols and an oxychromonol from Piliostigma reticulatum.
The leaf extract from the plant Piliostigma reticulatum was found to exhibit antimicrobial activity against some bacteria and fungi such as Staphylococcus aureus (NCTC 6571), Escherichia coli (NCTC 10418), Bacillus subtilis (NCTC 8236), Proteus vulgaris (NCTC 4175), Aspergillus niger (ATCC 10578) and Candida albicans (ATCC 10231). Upon investigation of the chemical constituents present in the leaf extract, a total of seven compounds were isolated and their structures were unambiguously established by spectroscopic methods including HR-MS and NMR spectrometry. Four of the isolated compounds were novel, namely 6-C-methyl-2-p-hydroxyphenyloxychromonol (piliostigmol), 1, 6,8-di-C-methylquercetin-3,3',7-trimethyl ether, 2, 6,8-di-C-methylquercetin-3,3'-dimethyl ether, 3 and 3',6,8,-tri-C-methylquercetin-3,7-dimethyl ether, 4. The other three were known C-methylated flavonols and they were isolated from P. reticulatum for the first time. These were 6-C-methylquercetin-3-methyl ether, 5, 6,8-di-C-methylkaempferol-3-methyl ether, 6 and 6-C-methylquercetin-3,3',7-trimethyl ether 7. All the isolated compounds were tested for cytotoxicity using the brine shrimp toxicity assay and all of them were active albeit at different levels. With respect to antibacterial activity piliostigmol, 1 showed the highest activity against E. coli (MIC=2.57 microg/ml, 0.006 micromol), which is three times more that of Amoxicillin, where as 4 and 7 showed the least activity.
Babajide
Olalekan J
OJ
Department of Chemistry, University of the Western Cape, Private Bag X17, Bellville 7535, South Africa.
Babajide
Omotola O
OO
Daramola
Abimbola O
AO
Mabusela
Wilfred T
WT
D000818:Animals; D000900:Anti-Bacterial Agents / Q000737:chemistry / Q000494:pharmacology; D001156:Artemia / Q000187:drug effects; D007887:Fabaceae / Q000737:chemistry*; D044948:Flavonols / Q000737:chemistry* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D050296:Microbial Viability / Q000187:drug effects; D015394:Molecular Structure; D013329:Structure-Activity Relationship
D000900:Anti-Bacterial Agents; D044948:Flavonols