Isolation of cupanioside, a novel cytotoxic and antibacterial long-chain fatty alcohol glycoside from the bark of Cupania glabra.
The crude dichloromethane extract from the stem bark of Cupania glabra (Sapindaceae), showed in vitro cytotoxic activity against Hep G2, MDA-MB-231, Hs 578T, MCF-7, and PC-3 cells, and antibacterial activity against Bacillus cereus, Staphylococcus aureus, and Escherichia coli. Bioactivity-directed fractionation led to isolation of the new 1-O-[2'',3'',4''-tri-O-acetyl-alpha-L-rhamnopyranosyl-(1-->2)-beta- D-glucopyranosyl]-hexadecanol (cupanioside) as the cytotoxic agent. The structure was elucidated by analysis of 2D-NMR spectra.
Setzer
William N
WN
Department of Chemistry, University of Alabama in Huntsville, Huntsville, Alabama, USA. wsetzer@chemistry.uah.edu
Vogler
Bernhard
B
Schmidt
Jennifer M
JM
Petty
Julie L
JL
Haber
William A
WA
D000900:Anti-Bacterial Agents / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D000972:Antineoplastic Agents, Phytogenic / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D001409:Bacillus cereus / Q000187:drug effects; D045744:Cell Line, Tumor / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D005233:Fatty Alcohols / Q000008:administration & dosage / Q000494:pharmacology / Q000627:therapeutic use; D006027:Glycosides / Q000008:administration & dosage / Q000494:pharmacology / Q000627:therapeutic use; D006801:Humans; D008826:Microbial Sensitivity Tests; D008517:Phytotherapy; D024301:Plant Bark; D010936:Plant Extracts / Q000008:administration & dosage / Q000494:pharmacology* / Q000627:therapeutic use; D029631:Sapindaceae; D013211:Staphylococcus aureus / Q000187:drug effects
D000900:Anti-Bacterial Agents; D000972:Antineoplastic Agents, Phytogenic; D005233:Fatty Alcohols; D006027:Glycosides; D010936:Plant Extracts