Cytotoxic Falcarinol Oxylipins from Dendropanax arboreus

• Published in: Journal of natural products (Washington, D.C.) D.C.), 1996-08, Vol.59 (8), p.748-753
• Main Authors: Bernart, Matthew W, Cardellina, John H, Balaschak, Michael S, Alexander, Mark R, Shoemaker, Robert H, Boyd, Michael R
• Format: Article
• Language: English
• Subjects: agentes antineoplasticos; Alkynes; Animals; antineoplastic agents; araliaceae; Biological and medical sciences; Cell Division - drug effects; chemical composition; Chemical Fractionation; chemical structure; chemistry; chimie; Chromatography, Gel; composicion quimica; composition chimique; Disease Models, Animal; Diynes; Dose-Response Relationship, Drug; Drugs, Chinese Herbal - chemistry; Drugs, Chinese Herbal - isolation & purification; Drugs, Chinese Herbal - pharmacology; espectrometria; estructura quimica; Fatty Alcohols - chemistry; Fatty Alcohols - isolation & purification; Fatty Alcohols - pharmacology; Female; feuille; General pharmacology; hidrocarburos; hojas; Humans; hydrocarbons; hydrocarbure; leaves; Magnetic Resonance Spectroscopy; Medical sciences; medicament cytostatique; Melanoma - drug therapy; Melanoma - pathology; Mice; Mice, Nude; Panax; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant Extracts - pharmacology; Plants, Medicinal; porto rico; puerto rico; quimica; spectrometrie; spectrometry; structure chimique; Structure-Activity Relationship; substance toxique; sustancias toxicas; toxic substances; Transplantation, Heterologous; Tumor Cells, Cultured
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np960224o

The crude organic extract of Dendropanax arboreus was selected as a candidate for bioassay-guided 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 diynene (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.