Falcarinol (9Z-heptadeca-1,9-diene-4,6-diyn-3-ol; (1) is a polyacetylene commonly found in several plant families. The absolute configuration of naturally occurring 1 is not clear and contradictory results have been reported in the literature. Determination of the absolute configuration of 1 from Pastinaca sativa L. was carried out. Isolation of 95% pure 1 was performed via successive fractionation and preparative-HPLC. A racemic mixture comprised of 3R-1 and 3S-1 was synthesized in order to confirm the absolute configuration of the isolated natural product using chiral HPLC. Based on a combination of chiral HPLC and specific rotation, 1 present in P. sativa was found to have a 3R absolute configuration (i.e. (3R, 9Z)-heptadeca-1,9-diene-4,6-diyn-3-ol).
MintoR.E., BlacklockB.J. (2008) Biosynthesis and function of polyacetylenes and allied natural products. Progress in Lipid Research, 47, 233–306.
2.
ChristensenL.P. (1998) Biological activities of naturally occurring acetylenes and related compounds from higher plants. Recent Research Developments in Phytochemistry, 2, 227–257.
3.
TanakaN., MatsuuraE., TeraharaN., IshimaruK. (1999) Secondary Metabolites in Transformed Root Cultures of Campanula glomerata, Journal of Plant Physiology, 155, 251–254.
4.
TengC-M, KuoS-C, KoF-N, LeeJ-C, LeeL-G, ChenS-C, HuangT-F. (1989) Antiplatelet actions of panaxynol and ginsenosides isolated from ginseng. Biochimica et Biophysica Acta (BBA) - General Subjects, 990, 315–320.
5.
LechnerD., StavriM., OluwatuyiM., Pereda-MirandaR., GibbonsS. (2004) The anti-staphylococcal activity of Angelica dahurica (Bai Zhi). Phytochemistry, 65, 331–335.
MatsunagaH., KatanoM., YamamotoH., FujitoH., MoriM., TakataK. (1990) Cytotoxic activity of polyacetylene compounds in Panax ginseng C. A. MEYER, Chemical & Pharmaceutical Bulletin, 38, 3480–3482.
8.
ChristensenL.P., JensenM., KidmoseU. (2006) Simultaneous determination of ginsenosides and polyacetylenes in American ginseng root (Panax quinquefolium L.) by high-performance liquid chromatography. Journal of Agricultural and Food Chemistry, 54, 8995–9003.
9.
TakahashiM., IsoiM., YoshitakaK., YoshikuraM. (1964) Studies on the components of Panax ginseng C. A. Meyer. II. Yakugaku Zasshi, 84, 752–756.
10.
TakahashiM., YoshikuraM. (1964) Studies on the components of Panax ginseng C. A. Meyer. III, Yakugaku Zasshi, 84, 757–759.
11.
BohlmannF., NiedballaU., RodeK-M. (1966) Polyacetylenverbindungen. CXVIII. Über neue polyine mit C17-Kette, Chemische Berichte, 99, 3552–3558.
12.
CrosbyD.G., AharonsonN. (1967) The structure of carotatoxin, a natural toxicant from carrot. Tetrahedron, 23, 465–472.
13.
KobayashiM., MahmudT., UmezomeT., WangW., MurakamiN., KitagawaI. (1997) The absolute stereostructures of the polyacetylenic constituents of ginseng Radix Rubra, Tetrahedron, 53, 15691–15700.
14.
ZhengG., LuW., AisaH.A., CaiJ. (1999) Absolute configuration of falcarinol, a potent antitumor agent commonly occurring in plants. Tetrahedron Letters, 40, 2181–2182.
15.
MayerS.F., SteinreiberA., OrruR.V.A., FaberK. (2002) Chemoenzymatic asymmetric total syntheses of antitumor agents (3R,9R,10R)- and (3S,9R,10R)-panaxytriol and (R)- and (S)-falcarinol from Panax ginseng using an enantioconvergent enzyme-triggered Cascade reaction. The Journal of Organic Chemistry, 67, 9115–9121.
16.
McLaughlinN.P., ButlerE., EvansP., BruntonN.P., KoidisA., RaiD.K. (2010) A short synthesis of (+) and (-)-falcarinol. Tetrahedron, 66, 9681–9687.
17.
MatsuuraH., SaxenaG., FarmerS.W., HancockR.E.W., TowersG.H.N. (1996) Antibacterial and antifungal polyine compounds from Glehnia littoralis ssp. leiocarpa. Planta Medica, 62, 256–259.
18.
RatnayakeA.S., HemscheidtT. (2002) Olefin cross-metathesis as a tool in natural product degradation. The stereochemistry of (+)-falcarindiol, Organic Letters, 4, 4667–4669.
19.
LemmichE. (1981) The absolute configuration of the acetylenic compound falcarindiol. Phytochemistry, 20, 1419–1420.
20.
BernartM.W., CardellinaJ.H., BalaschakM.S., AlexanderM.R., ShoemakerR.H., BoydM.R. (1996) Cytotoxic falcarinol oxylipins from Dendropanax arboreus. Journal of Natural Products, 59, 748–753.
21.
YadavJ.S., BoyapellyK., AlugubelliS.R., PabbarajaS., VangalaJ.R., KalivendiS.V. (2011) Stereoselective total synthesis of (+)-oploxyne A, (-)-oploxyne B, and their C–10 epimers and structure revision of natural oploxyne B, The Journal of Organic Chemistry, 76, 2568–2576.
22.
YangM.C., KwonH.C., KimY-J, LeeK.R., YangH.O. (2010) Oploxynes A and B, polyacetylenes from the stems of Oplopanax elatus. Journal of Natural Products, 73, 801–805.
23.
SatohY., SatohM., IsobeK., MohriK., YoshidaY., FujimotoY. (2007) Studies on Panax acetylenes: Absolute structure of a new Panax acetylene, and inhibitory effects of related acetylenes on the growth of L-1210 cells, Chemical & Pharmaceutical Bulletin (Tokyo), 55, 561–564.
24.
ChristensenL.P., BrandtK. (2006) Bioactive polyacetylenes in food plants of the Apiaceae family: Occurrence, bioactivity and analysis. Journal of Pharmaceutical and Biomedical Analysis, 41, 683–693.
25.
ChristensenL.P., JakobsenH.B. (2008) Polyacetylenes: distribution in higher plants, pharmacological effects and analysis. In Thin Layer Chromatography in Phytochemistry, Vol. 99, Waksmundzka-HajnosM, ShermaJ, KowalskaT., (Eds), CRC Press, Boca Raton, FL, USA
26.
ZidornC., JohrerK., GanzeraM., SchubertB., SigmundE.M., MaderJ., GreilR., EllmererE.P., StuppnerH. (2005) Polyacetylenes from the Apiaceae vegetables carrot, celery, fennel, parsley, and parsnip and their cytotoxic activities. Journal of Agricultural and Food Chemistry, 53, 2518–2523.
27.
SøltoftM., EriksenM., TrägerA., NielsenJ., LaursenK., HustedS., HalekohU., KnuthsenP. (2010) Comparison of polyacetylene content in organically and conventionally grown carrots using a fast ultrasonic liquid extraction method, Journal of Agricultural and Food Chemistry, 58, 7673–7679.
