Falkarindiol
| Falkarindiol | |
|---|---|
 Strukturní vzorec | |
 Model molekuly | |
| Obecné | |
| Systematický název | (3R,8S,9Z)-heptadeka-1,9-dien-4,6-diyn-3,8-diol |
| Ostatní názvy | cis-heptadeka-1,9-dien-4,6-diyn-3,8-diol |
| Sumární vzorec | C17H24O2 |
| Identifikace | |
| Registrační číslo CAS | 55297-87-5 |
| PubChem | 5281148 |
| SMILES | CCCCCCC/C=C\[C@H](O)C#CC#C[C@H](O)C=C |
| InChI | 1S/C17H24O2/c1-3-5-6-7-8-9-10-14-17(19)15-12-11-13-16(18)4-2/h4,10,14,16-19H,2-3,5-9H2,1H3/b14-10-/t16-,17+/m1/s1 |
| Vlastnosti | |
| Molární hmotnost | 260,37 g/mol |
Některá data mohou pocházet z datové položky. | |
Falkarindiol je organická sloučenina patřící mezi polyyny, která se vyskytuje v mrkvi, kde má fungicidní účinky.[1][2]
Falkarindiol má hlavní podíl na hořké chuti mrkví.[3]
Falkarindiol a jiné podobné polyyny se nacházejí i v mnoha jiných miříkovitých rostlinách, například kopru a petrželi.[4]
U falkarindiolu a podobných sloučenin byla objevena řada biologických účinků,[5][6][7] díky čemuž mají účinky na metabolismus a jsou zkoumány jako možné doplňky stravy.[8]
Falkarindiol je nejaktivnějším z několika potenciálně protinádorově působících polyynů v oplopanaxu hrozivém (Oplopanax horridus), rostlině používané při léčení domorodci na Aljašce a na severozápadním pobřeží Tichého oceánu.[9]
Odkazy
Reference
V tomto článku byl použit překlad textu z článku Falcarindiol na anglické Wikipedii.
- ↑ B. Garrod. Cis-heptadeca-1,9-diene-4,6-diyne-3,8-diol, an antifungal polyacetylene from carrot root tissue. Physiological Plant Pathology. 1978, s. 241–246. DOI 10.1016/0048-4059(78)90039-5.
- ↑ M. S. Kemp. Falcarindiol: An antifungal polyacetylene from Aegopodium podagraria. Phytochemistry. 1978, s. 1002. DOI 10.1016/S0031-9422(00)88669-0.
- ↑ A. Czepa; T. Hofmann. 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. 2003, s. 3865–3873. DOI 10.1021/jf034085+. PMID 12797757.
- ↑ L. P. Christensen; K. Brandt. Bioactive polyacetylenes in food plants of the Apiaceae family: Occurrence, bioactivity and analysis. Journal of Pharmaceutical and Biomedical Analysis. 2006, s. 683–693. DOI 10.1016/j.jpba.2006.01.057. PMID 16520011.
- ↑ H. R. Jin, J. Zhao, Z. Zhang, Y. Liao, C. Z. Wang, W. H. Huang, S. P. Li, T. C. He, C. S. Yuan, W. Du. The antitumor natural compound falcarindiol promotes cancer cell death by inducing endoplasmic reticulum stress. Cell Death and Disease. 2012, s. e376. DOI 10.1038/cddis.2012.122. PMID 22914324.
- ↑ P. Wyrembek; R. Negri; P. Kaczor; M. Czyżewska; G. Appendino; J. W. Mozrzymas. Falcarindiol allosterically modulates GABAergic currents in cultured rat hippocampal neurons. Journal of Natural Products. 2012, s. 610–616. DOI 10.1021/np2008522. PMID 22432736.
- ↑ Wang L, Palme V, Schilcher N, Ladurner A, Heiss EH, Stangl H, Bauer R, Dirsch VM, Atanasov AG The Dietary Constituent Falcarindiol Promotes Cholesterol Efflux from THP-1 Macrophages by Increasing ABCA1 Gene Transcription and Protein Stability. Frontiers in Pharmacology 2017 Sep 1;8:596 doi: 10.3389/fphar.2017.00596
- ↑ L. P. Christensen. Aliphatic C17-Polyacetylenes of the Falcarinol Type as Potential Health Promoting Compounds in Food Plants of the Apiaceae Family. Recent Patents on Food, Nutrition & Agriculture. 2011, s. 64–77. DOI 10.2174/2212798411103010064. PMID 21114468.
- ↑ S. Sun; G. J. Du; L. W. Qi; S. Williams; C. Z. Wang; C. S. Yuan. Hydrophobic constituents and their potential anticancer activities from Devil's Club (Oplopanax horridus Miq.). Journal of Ethnopharmacology. 2010, s. 280–285. DOI 10.1016/j.jep.2010.08.026. PMID 20723598.
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Falcarindiol 3D BS.png
Autor: Mplanine, Licence: CC BY-SA 4.0
Falcarindiol is a polyyne found in carrot roots which has antifungal activity. Falcarindiol is the main compound responsible for bitterness in carrots. Falcarindiol and other falcarindiol-type polyacetylenes are also found in many other plants of the family Apiaceae, including some commonly used seasonings such as dill and parsley. A variety of bioactivities have been reported so far for falcaridiol and the falcarindiol-type polyacetylenes, and because of potential health-promoting metabolic effects these compounds are studied as potential nutraceuticals. 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.
Autor: Mplanine, Licence: CC BY-SA 4.0
Falcarindiol is a polyyne found in carrot roots which has antifungal activity. Falcarindiol is the main compound responsible for bitterness in carrots. Falcarindiol and other falcarindiol-type polyacetylenes are also found in many other plants of the family Apiaceae, including some commonly used seasonings such as dill and parsley. A variety of bioactivities have been reported so far for falcaridiol and the falcarindiol-type polyacetylenes, and because of potential health-promoting metabolic effects these compounds are studied as potential nutraceuticals. 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.
Falcarindiol.svg
Chemical structure of falcarindiol
Chemical structure of falcarindiol