Cytotoxic falcarinol oxylipins from Dendropanax arboreus.
The crude organic extract of Dendropanax arboreus was selected as a candidate for bioassayguided fractionation on the basis of its relatively selective cytotoxicity to a subset of cell lines within the National Cancer Institute's disease-oriented in vitro tumor-screening panel. The major compound responsible for the in vitro cytotoxicity was falcarinol (1). Several other known compounds were isolated and found to be cytotoxic, including dehydrofalcarinol (2), a diyenne (3), falcarindiol (4), and dehydrofalcarindiol (5). In addition, two novel polyacetylenes, dendroarboreols A (6) and B (7), were isolated and characterized by standard and inverse-detected NMR methods. Compounds were selected from this series for absolute stereochemical determination using the modified Mosher method and preliminary in vivo evaluation using a LOX melanoma mouse xenograft model.
Bernart
M W
MW
Division of Cancer Treatment, Diagnosis and Centers, National Cancer Institute-Frederick Cancer Research & Development Center, Frederick, Maryland 21702-1201, USA.
Cardellina
J H
JH
Balaschak
M S
MS
Alexander
M R
MR
Shoemaker
R H
RH
Boyd
M R
MR
D000480:Alkynes; D000818:Animals; D002455:Cell Division / Q000187:drug effects; D005591:Chemical Fractionation; D002850:Chromatography, Gel; D004195:Disease Models, Animal; D053280:Diynes; D004305:Dose-Response Relationship, Drug; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005233:Fatty Alcohols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D005260:Female; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008545:Melanoma / Q000188:drug therapy* / Q000473:pathology; D051379:Mice; D008819:Mice, Nude; D005894:Panax; D010936:Plant Extracts / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D010946:Plants, Medicinal; D013329:Structure-Activity Relationship; D014183:Transplantation, Heterologous; D014407:Tumor Cells, Cultured
D000480:Alkynes; D053280:Diynes; D004365:Drugs, Chinese Herbal; D005233:Fatty Alcohols; D010936:Plant Extracts; C018541:falcarinol