Falcarinol

      Falcarinol
      IUPAC name

      (3S,9Z)-Heptadeca-1,9-diene-4,6-diyn-3-ol
      Other names

      Carotatoxin
      Identifiers
      CAS number 21852-80-2 YesY
      PubChem 5469789
      ChemSpider 4580244
      KEGG C08450 YesY
      Jmol-3D images Image 1
      Properties
      Molecular formula C17H24O
      Molar mass 244.37 g mol−1
       YesY (verify) (what is: YesY/N?)
      Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
      Infobox references

      Falcarinol (carotatoxin) is a natural pesticide and fatty alcohol found in carrots (Daucus carota), red ginseng (Panax ginseng) and ivy. In carrots, it occurs in a concentration of approximately 2 mg/kg.[1][2] As a toxin, it protects roots from fungal diseases, such as liquorice rot that causes black spots on the roots during storage.

      Chemistry

      Falcarinol is a polyyne with two carbon carbon triple bonds and two double bonds.[3] Falcarinol can cause allergic and irritant contact dermatitis.[4] It is structurally related to the oenanthotoxin and cicutoxin.

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      Biological effects

      It was shown that falcarinol acts as a covalent cannabinoid receptor type 1 inverse agonist and blocks the effect of anandamide in keratinocytes, leading to pro-allergic effects in human skin.[5]

      Preliminary research in animal models suggest that falcarinol may have a protective effect against certain types of cancer. Laboratory rats fed a diet containing raw carrots or isolated falcarinol were a third less likely to develop full-scale tumors induced by azoxymethane than those in a control group.[6]

      Normal consumption of carrots doesn't causes any toxic effect in humans. However, when falcarinol is delivered in high doses to laboratory animals, it causes neurotoxical problems.[7]

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      See also

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      References

      1. ^ Crosbya, D. G.; Aharonson, N. (1967). "The Structure of Carotatoxin, a Natural Toxicant From Carrot". Tetrahedron 23 (1): 465–472. doi:10.1016/S0040-4020(01)83330-5. 
      2. ^ Badui (1988). Diccionario de Tecnología de Alimentos. D. F. Mexico: Alhambra Mexicana. ISBN 968-444-071-5. 
      3. ^ S. G. Yates, R. E. England (1982). "Isolation and analysis of carrot constituents: myristicin, falcarinol, and falcarindiol". Journal of Agricultural and Food Chemistry 30 (2): 317–320. doi:10.1021/jf00110a025. 
      4. ^ S. Machado, E. Silva, A. Massa (2002). "Occupational allergic contact dermatitis from falcarinol". Contact Dermatitis 47 (2): 109–125. doi:10.1034/j.1600-0536.2002.470210_5.x. 
      5. ^ M. Leonti, S. Raduner, L. Casu, F. Cottiglia, C. Floris, KH. Altmann, J. Gertsch (2010). "Falcarinol is a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin". Biochemical Pharmacology 79 (12): 1815–1826. doi:10.1016/j.bcp.2010.02.015. PMID 20206138. 
      6. ^ M. Kobæk-Larsen, L. P. Christensen, W. Vach, J. Ritskes-Hoitinga and K. Brandt (2005). "Inhibitory Effects of Feeding with Carrots or (-)-Falcarinol on Development of Azoxymethane-Induced Preneoplastic Lesions in the Rat Colon". Journal of Acricultural and Food Chemistry 53 (5): 1823–1827. doi:10.1021/jf048519s. PMID 15740080. 
      7. ^ Deshpande (2002). Handbook of Food Toxicology. Hyderabad, India: CRC Press. ISBN 978-0-8247-0760-6. 
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      Last modified on 16 May 2013, at 20:03