Falcarinol

Abstract: 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.

Abstract: The effects of genotype, root size, storage, and processing on the content of bioactive compounds in carrots were determined to investigate the possibilities for optimizing the health-promoting properties of this vegetable. The content of polyacetylenes (falcarinol, falcarindiol, falcarindiol-3-acetate), carotenoids (α-and β-carotene), and isocoumarin 6-methoxymellein (6-MM) varied significantly between 6 genotypes of the Nantes type. The content of falcarindiol, falcarindiol-3-acetate, and 6-MM was significantly higher in small (50- to 100-g root size) than in extra large root sizes (>250-g root size). Refrigerated storage of the roots for 4 mo at 1 °C before processing resulted in a significantly higher content of polyacetylenes and no differences in the content of carotenoids and 6-MM compared with frozen storage of processed carrots. The content of falcarinol increased and that of falcarindiol and falcarindiol-3-acetate decreased during steam blanching of the carrots before freezing. No changes were observed in the content of carotenoids and 6-MM.

Abstract: The effects of intake of dietary amounts of carrot or corresponding amounts of (−)-(3R)-falcarinol from carrots on development of azoxymethane (AOM)-induced colon preneoplastic lesions were examined in male BDIX rats. Three groups of eight AOM-treated rats were fed the standard rat feed Altromin supplemented with either 10% (w/w) freeze-dried carrots with a natural content of 35 μg falcarinol/g, 10% maize starch to which was added 35 μg falcarinol/g purified from carrots, or 10% maize starch (control). After 18 weeks, the animals were euthanized and the colon was examined for tumors and aberrant crypt foci (ACF), which were classified into four size classes. Although the number of small ACF was unaffected by the feeding treatments, the numbers of lesions as a function of increasing size class decreased significantly in the rats that received one of the two experimental treatments, as compared with the control treatment. This indicates that the dietary treatments with carrot and falcarinol delayed or retar...

Abstract: Carrots ( Daucus carota L.) contain phytochemicals including carotenoids, phenolics, polyacetylenes, isocoumarins, and sesquiterpenes. Purple carrots also contain anthocyanins. The anti-inflammatory activity of extracts and phytochemicals from purple carrots was investigated by determining attenuation of the response to lipopolysaccharide (LPS). A bioactive chromatographic fraction (Sephadex LH-20) reduced LPS inflammatory response. There was a dose-dependent reduction in nitric oxide production and mRNA of pro-inflammatory cytokines (IL-6, IL-1beta, TNF-alpha) and iNOS in macrophage cells. Protein secretions of IL-6 and TNF-alpha were reduced 77 and 66% in porcine aortic endothelial cells treated with 6.6 and 13.3 microg/mL of the LH-20 fraction, respectively. Preparative liquid chromatography resulted in a bioactive subfraction enriched in the polyacetylene compounds falcarindiol, falcarindiol 3-acetate, and falcarinol. The polyacetylenes were isolated and reduced nitric oxide production in macrophage cells by as much as 65% without cytotoxicity. These results suggest that polyacetylenes, not anthocyanins, in purple carrots are responsible for anti-inflammatory bioactivity.