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Chemical Compound Review: 

Falcarinol     (9E)-heptadeca-1,9-dien-4,6- diyn-3-ol

Synonyms: AC1NS4DT, (Z)-(-)-1,9-heptadecadiene-4,6-diyne-3-ol
 
 
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Disease relevance of Falcarinol

 

High impact information on Falcarinol

  • The naturally occurring toxicants myristicin, twelve related aromatic ethers and the toxic acetylenic alcohol, falcarinol, were separated from one another by high-pressure liquid chromatography (HPLC) [3].
  • Panaxynol, a polyacetylene ((3R)-heptadeca-1,9-diene-4,6-diyn-3-ol; syn. falcarinol), was isolated from the lipophilic fractions of Panax notoginseng, a Chinese traditional medicinal plant [4].
  • Keywords: Panax quinquefolium; roots; ginsenosides; falcarinol; panaxydol; extraction; quantification; HPLC analysis [5].
  • The known compounds were the diterpenes anisotomenoic acid 1, anisotomene-1-ol 2, 16-acetoxyanisotomenoic acid 4 and anisotomene-1,12-diol 5; and the polyacetylenes falcarinol 8, falcarindiol 9, (+)-9(Z),17-octadecadiene-12,14-diyne-1,11,16-triol 10, and (+)-9(Z),17-octadecadiene-12,14-diyne-1,11,16-triol 1-acetate 11 [6].
  • Two of these are known C17 polyacetylenic metabolites, falcarinol [1] and falcarindiol [2], previously isolated from several species of the Umbelliferae and Araliaceae [7].

References

  1. Occupational allergic contact dermatitis from falcarinol. Machado, S., Silva, E., Massa, A. Contact Derm. (2002) [Pubmed]
  2. Polyacetylenes from the Apiaceae vegetables carrot, celery, fennel, parsley, and parsnip and their cytotoxic activities. Zidorn, C., Jöhrer, K., Ganzera, M., Schubert, B., Sigmund, E.M., Mader, J., Greil, R., Ellmerer, E.P., Stuppner, H. J. Agric. Food Chem. (2005) [Pubmed]
  3. High-pressure liquid chromatographic separation of the naturally occurring toxicants myristicin, related aromatic ethers and falcarinol. Wulf, L.W., Nagel, C.W., Branen, A.L. J. Chromatogr. (1978) [Pubmed]
  4. Panaxynol induces neurite outgrowth in PC12D cells via cAMP- and MAP kinase-dependent mechanisms. Wang, Z.J., Nie, B.M., Chen, H.Z., Lu, Y. Chem. Biol. Interact. (2006) [Pubmed]
  5. Simultaneous Determination of Ginsenosides and Polyacetylenes in American Ginseng Root (Panax quinquefolium L.) by High-Performance Liquid Chromatography. Christensen, L.P., Jensen, M., Kidmose, U. J. Agric. Food Chem. (2006) [Pubmed]
  6. Chemosystematic investigations of irregular diterpenes in Anisotome and related New Zealand Apiaceae. Zidorn, C., Sturm, S., Dawson, J.W., van Klink, J.W., Stuppner, H., Perry, N.B. Phytochemistry (2002) [Pubmed]
  7. Bioactive metabolites from Sicilian marine fennel, Crithmum maritimum. Cunsolo, F., Ruberto, G., Amico, V., Piattelli, M. J. Nat. Prod. (1993) [Pubmed]
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