An antimitotic and cytotoxic chalcone from Fissistigma lanuginosum.
Bioassay-guided fractionation of an ethyl acetate extract of Fissistigma lanuginosum led to the isolation of the known chalcone pedicin [1], which inhibited tubulin assembly into microtubules (IC50 value of 300 microM). From the same EtOAc fraction, two new condensed chalcones, fissistin [2] and isofissistin [3], which showed cytotoxicity against KB cells, were also obtained, together with the inactive dihydropedicin [4] and 6,7-dimethoxy-5,8-dihydroxyflavone [5]. In addition, the aminoquinones 6, 8, and 9 were isolated from the alkaloid extract. These compounds were artifacts, prepared by treatment of 1, 4, and 2, respectively, with NH4OH. The structures of the new compounds were elucidated by spectral methods, especially 2D nmr.
Alias
Y
Y
Department of Chemistry, University of Malaya, Kuala Lumpur.
Awang
K
K
Hadi
A H
AH
Thoison
O
O
Sévenet
T
T
Païs
M
M
D000970:Antineoplastic Agents / Q000302:isolation & purification* / Q000494:pharmacology; D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology; D002470:Cell Survival / Q000187:drug effects; D002599:Chalcone / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000494:pharmacology; D000431:Ethanol; D006801:Humans; D007624:KB Cells; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D010936:Plant Extracts / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013056:Spectrophotometry, Ultraviolet
D000970:Antineoplastic Agents; D000972:Antineoplastic Agents, Phytogenic; D010936:Plant Extracts; C096505:fissistin; C096506:isofissistin; D000431:Ethanol; D002599:Chalcone