Falcarinol carrots

Kobaek-Larsen M, Christensen L P, Vach W, Ritskes-Hoitinga J and Brandt K (2005), Inhibitory effects of feeding with carrots or (-) falcarinol on development of azomethane-induced preneoplastic lesions in the rat colon , J Agric Food Chem, 53, 1823-1827. 

Myristicin has not been reported to possess antifungal activity, and therefore is not a phytoalexin according to the standard interpretation of this term (1 ). It does, however, potentiate the activity of the insecticide, paraoxon, in flies by inhibiting its degradation (2), and may in similar manner potentiate the action of phytoalexins of carrot root (falcarinol, falcarindiol,... 

In the following experiments carrot roots were exposed to various sources of ultraviolet light in the laboratory and set aside to allow time for enzyme synthesis. Following this period, changes in myristicin and phytoalexin levels were measured. All of these components of carrot root are measured in one assay. Myristicin and 6-methoxymellein concentrations increased in some samples after irradiation with ultraviolet light falcarinol and falcarindiol concentration changes did not appear to be related to the ultraviolet light used in this study. 

A four-year study of field-grown commercial carrot roots revealed that recently harvested, unprocessed carrot roots contained 24 ppm falcarinol and 65 ppm falcarindiol (8). 6-Methoxymellein (6-MM) had not been identified by Yates al (8) at that time, and was not measured in that study. Reexamination of data revealed that 6-MM was absent from most samples, but present in a few at concentrations of 2 to 8 ppm. Myristicin, 1 ppm, was detected in only one sample. Wulf et 1978, reported that myristicin was present in supermarket carrots. Other studies have shown that certain brands of supermarket carrots contain myristicin while others do not (Yates, unpub.). The presence of myristicin in some samples from the supermarket and its absence in unprocessed carrots analyzed as soon after harvest as possible suggests that myristicin formation is induced during some stage of processing. Since light is known to be an elicitor of a plant system that results in the synthesis of phenylpropanoid compounds, a study of the effect of light on harvested carrot roots was undertaken. 

Falcarinol and falcarindiol concentration changes are small compared to those in myristicin and 6-MM content, and do not appear related to radiation (Table II). These polyacetylenes are present in fresh carrots. Immediately upon wounding, they are translocated to the surface through oil ducts (3 ) > and, therefore, their function as phytoalexins apparently does not depend upon novo synthesis. 

Yates, S. G., and R. E. England. Isolation and analysis of carrot constituents myristicin, falcarinol, and falcarindiol. J Agr Food Chem 1982 30(2) 317-320. 

Few recent studies have been made on alkyne biosynthesis. Crepenynic acid has been shown to be a precursor of C9 to C14 polyalkynes in fungal cultures, and was also demonstrated to be a precursor of falcarinol cf 4, falcarinone) in tissue cultures of Daucus car Ota (carrot). (14-Z)-14,15-didehydrocrepenynic acid (67, Figure 10) is predominately converted into 68 by fungi of Lepista spp whereas Caprinis spp yield 69. ... 

Analysis of Carrot Constituents Myristicin, Falcarinol, and Falcarindiol... 

Falcarinol, falcarindiol, and myristicin contents of carrots, Daucus carota L., were determined by a sequence of dichloromethane extraction, column chromatographic purification, and gas-liquid chromatographic analysis. High Color 9, Long Imperator 58, Danvers 126, and Spartan Bonus varieties were grown in Wisconsin (1979-1982), Florida (1980-1982), California (1980-1982), Arizona... 

The standard error of a mean based on 2 samples (4 carrots per sample), 2 aliquots per sample, and 2 runs per sample, or 8 observations, was 2.8 for falcarinol and 4.8 for falcarindiol. For single observations, the respective standard deviations were 15.2 and 24.8. About 70% of the variation for falcarinol was associated with sample, but only about 25% for falcarindiol. For falcarindiol, variation associated with the assay differences contributed most of the variation. Precision for both toxicants... 

Table I. ummary of Means of Falcarinol and Falcarindiol for Thirteen Carrot Varieties-...

From the ether-soluble fraction, Takahashi etal. 134, 135) isolated sitosterol-P-D-glucoside, sitosterol, p-elemene (96), eremophilene (97) and a new polyacetylenic alcohol named panaxynol (98), the structure of which was elucidated as heptadeca-l,9(Z)-diene-4,6-diyn-3-ol by degradative and synthetic procedures. It is identical with carotatoxin from carrots 136) and falcarinol from Falcaria vulgaris 137). Recently two other polyacetylenic alcohols, 9,10-epoxy-3-hydroxyheptadeca-l-en-4,6-diyne [(99), panaxydol] 138) and heptadeca-l-en-4,6-diyn-3,9-diol (100) 139) were isolated from Ginseng roots by Wrobel et al. 

Yates, S. G., R. E. England, W. F. Kwolek, and P. W. Simon, Analysis of carrot constituents Myristicin, falcarinol, and falc-arindiol, in Xenobiotics in Foods and Feeds, ACS Symposium Series 234, (J. W. Finley and D. E. Schwass, eds.), 333-344, American Chemical Society, Washington, DC, 1983. 

Falcarinol, 0.1% (Hedera spp [ivy], Schefflera actin-ophylla [umbrella tree and carrots]) (Hausen et al. 1987)... 

More than 700 polyacetylene compounds have been characterized from plants, which are mainly prominent in the Asteraceae, Apiaceae and Campanulaceae including many medicinal plants from various parts of the world (Hudson 1989). Food plants of the Apiaceae plant family such as carrots, celery, parsley, fennel and parsnip contain a group of bioactive aliphatic C17-polyacetylenes including falcarinol, falcarindiol, panaxydiol, and polyacetylene 8-0-methylfalcarindiol (Zidom et al. 2005 Christensen and Brandt 2006). 

The most common acetylenes isolated from food plants are aliphatic acetylenes (Figures 5.1 and 5.3, and Table 5.1). Aliphatic acetylenes of the falcarinol-type (especially compounds 1, 2, 4 and 5) are widely distributed in the Apiaceae and Araliaceae plant families (Bohlmann et al. 1973 Hansen and Boll 1986), and consequently nearly all acetylenes found in the utilized/edible parts of food plants of the Apiaceae, such as carrot, caraway (Carum carvi), celery, celeriac (Apium graveolens var. rapaceum), fennel (Feonkulum vulgare), parsnip (Pastinaca sativa) and parsley are of the falcarinol-type... 

In the human diet carrots are the major dietary source of falcarinol, although it may also be supplied by many other plant food sources (Table 5.1). A recent in vitro study aiming to screen for potentially health promoting compounds from vegetables showed that falcarinol, but not -carotene, could stimulate differentiation of primary mammalian cells in concentrations between 0.004 and 0.4 p,M falcarinol. Toxic effects were found above >4p,M falcarinol (Figure 5.14), while f)-carotene had no effect even at 400 xM (Hansen et al 2003). This biphasic effect (hormesis) of falcarinol on cell proliferation is fiiUy in accordance with the hypothesis that most toxic compounds have beneficial effects... 

Figure 5.15 Concentration of falcarinol in ptema of 14 volunteers as a function of time after ingestion of a breakfast meal with 300, 600 and 900 ml carrot juice, respectively, containing 16, 33 and 49 pmol falcarinol, respectively. Means SEM.

Figure 5.16 Effect of treatments with carrot or falcarinol on the average numbers per animal of four types of (pre)cancerous lesions in rat colons, each size class representing increasingly advanced steps on the progression towards cancer. The size of aberrant crypt foci (ACF) was measured as the number of crypts found on a corresponding area of normal colon tissue. The smallest tumours correspond to an ACF size of 20. The trend for reduced relative numbers with increasing size of lesion was significant at P = 0.028.

Barley, G.C., Jones, E.R.H. and Thaller, V. (1988) Crepenynate as a precursor of falcarinol in carrot tissue culture. In J. Lam, H. Breteler, T. Arnason et al. (eds). Chemistry and Biology of Naturally-Occurring Acetylenes and Related Compounds (NOARC). Elsevier, Amsterdam, pp. 85-91. 

Figure 7.4 Carrots contain carotenoids, chlorogenic acids, phytosterols and the polyacetylene, falcarinol.

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