Falcarindiol

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Falcarindiol
Falcarindiol.svg
Names
IUPAC name
(3R,8S,9Z)-1,9-Heptadecadiene-4,6-diyne-3,8-diol
Other names
cis-Heptadeca-1,9-diene-4,6-diyne-3,8-diol
Identifiers
55297-87-5 YesY
ChEMBL ChEMBL69018
ChemSpider 4444588
Jmol 3D model Interactive image
PubChem 5281148
Properties
C17H24O2
Molar mass 260.371
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Falcarindiol is a polyacetylene found in carrot roots which has antifungal activity.[1][2] Falcarindiol is the main compound responsible for bitterness in carrots.[3] Falcarindiol and other falcarindiol-type polyacetylenes are also found in many other plants of the Apiaceae family, including some commonly used seasonings such as dill and parsley.[4] A variety of bioactivities have been reported so far for falcaridiol and the falcarindiol-type polyacetylenes,[5][6] and because of potential health-promoting metabolic effects these compounds are studied as potential nutraceuticals.[7] It is the most-active among several polyynes with potential anticancer activity found in Devil's Club (Oplopanax horridus), a medicinal plant used by many indigenous peoples in Alaska and the Pacific Northwest.[8]

See also[edit]

References[edit]

  1. ^ Garrod, B. (1978). "Cis-heptadeca-1,9-diene-4,6-diyne-3,8-diol, an antifungal polyacetylene from carrot root tissue". Physiologial Plant Pathology 13 (2): 241–246. doi:10.1016/0048-4059(78)90039-5. 
  2. ^ Kemp, M. S. (1978). "Falcarindiol: An antifungal polyacetylene from Aegopodium podagraria". Phytochemistry 17 (5): 1002. doi:10.1016/S0031-9422(00)88669-0. 
  3. ^ Czepa, A.; Hofmann, T. (2003). "Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot puree". Journal of Agricultural and Food Chemistry 51 (13): 3865–3873. doi:10.1021/jf034085+. PMID 12797757. 
  4. ^ Christensen, L. P.; Brandt, K. (2006). "Bioactive polyacetylenes in food plants of the Apiaceae family: Occurrence, bioactivity and analysis". Journal of Pharmaceutical and Biomedical Analysis 41 (3): 683–693. doi:10.1016/j.jpba.2006.01.057. PMID 16520011. 
  5. ^ Jin, H. R.; Zhao, J.; Zhang, Z.; Liao, Y.; Wang, C. Z.; Huang, W. H.; Li, S. P.; He, T. C.; Yuan, C. S.; Du, W. (2012). "The antitumor natural compound falcarindiol promotes cancer cell death by inducing endoplasmic reticulum stress". Cell Death and Disease 3 (8): e376. doi:10.1038/cddis.2012.122. PMC 3434669. PMID 22914324. 
  6. ^ Wyrembek, P.; Negri, R.; Kaczor, P.; Czyżewska, M.; Appendino, G.; Mozrzymas, J. W. (2012). "Falcarindiol allosterically modulates GABAergic currents in cultured rat hippocampal neurons". Journal of Natural Products 75 (4): 610–616. doi:10.1021/np2008522. PMID 22432736. 
  7. ^ Christensen, L. P. (2011). "Aliphatic C17-Polyacetylenes of the Falcarinol Type as Potential Health Promoting Compounds in Food Plants of the Apiaceae Family". Recent Patents on Food, Nutrition and Agriculture 3 (1): 64–77. doi:10.2174/2212798411103010064. PMID 21114468. 
  8. ^ Sun, S; Du, GJ; Qi, LW; Williams, S; Wang, CZ; Yuan, CS (2010). "Hydrophobic constituents and their potential anticancer activities from Devil's Club (Oplopanax horridus Miq.)". J Ethnopharmacol. 132 (1): 280–285. doi:10.1016/j.jep.2010.08.026.