Phytochemical investigation of the aerial parts of Cichorium intybus L. resulted in the isolation and identification of two new natural metabolites, 2,6-di[but-3(E)-en-2-onyl]naphthalene (1), and 3,3′,4,4′-tetrahydroxychalcone (2), along with nine known compounds. Their structures were determined by spectroscopic techniques including 1D and 2D NMR. The known compounds were identified as scopoletin (3), 4-hydroxyphenylacetic acid (4), 3-hydroxy-4-methoxybenzoic acid (5), 4,4′-dihydroxychalcone (6), 6,7-dihydroxycoumarine (7), 1-triacontanol (8), lupeol (9), β-sitosterol (10), and β-sitosterol-3-O-β-glucopyranoside (11). Compounds 4-6 and 8 are reported for the first time from C. intybus. Compounds 2 and 3 showed weak inhibitory activities against urease and α-chymotrypsin enzymes, respectively.
MammonM.I.A., ShahaniN.M., SyedG.M. (1988) Glimpses of the medicinal plants of Sindh.Sindh Agriculture University Press, Tandojam. 25.
3.
DanielM. (2006) Medicinal plants chemistry and properties.Oxford and IBH Press, New Delhi. 84.
4.
NorbaekR., NielsenK., KondoT. (2002) Anthocyanins from the flowers of Cichorium intybus. Phytochemistry, 60, 357–359.
5.
KisielW., ZielinskaK. (2001) Guaianolides from Cichorium intybus and structure revision of Cichorium sesquiterpene lactones. Phytochemistry, 57, 523–527.
6.
AbdallaM., LakanyE., MahaA., ElaA., Abdul-GhaniM., HattemM. (2004) Chemical constituents and biological activity of Cichorium intybus L. Natural Product Sciences, 10, 69–73.
7.
TimmermansJ.W., SlaghekT.M., IizukaM., EndeW.V., RooverJ.D., LaereA. (2001) Isolation and structural analysis of new fructans produced by chicory. Journal of Carbohydrate Chemistry, 20, 375–395.
8.
Dem'yanenkoV.G., DranikL.I., Khar'kN.I., KhimF.K. (1973) Flavonoids of Cichorium intybus. Chemistry of Natural Compounds, 9, 115.
9.
Dem'yanekoV.G., DranikL.I. (1971) Coumarins of the raceme of Cichorium intybus. Chemistry of Natural Compounds, 7, 104.
10.
KisielW., MichalskaK. (2002) A new coumarin glucoside ester from Cichorium intybus. Fitoterapia, 73, 544–546.
11.
JunN., HongG., JunK. (2007) Synthesis and evaluation of 2′,4′,6′-trihydroxychalcones as a new class of tyrosinase inhibitors. Bioorganic and Medicinal Chemistry, 15, 2396–2402.
12.
RöseckeJ., WilfriedA., KönigW.A. (2000) Constituents of various wood-rotting basidiomycetes. Phytochemistry, 54, 603–610.
WeatherburnM.W. (1967) Phenol-hypochlorite reaction for determination of ammonia. Analytical Chemistry, 39, 971–974.
17.
ArfanM., AliM., AhmadH., AnisI., KhanA., ChoudharyM.I., ShahM.R. (2010) Urease inhibitors from Hypericum oblongifolium. Journal of Enzyme Inhibition and Medicinal Chemistry, 25, 296–299.
18.
CannellR.J.P., KellamS.J., OwsiankaA.M., WalkerJ.M. (1988) Results of a large scale screen of microalgae for the production of protease inhibitors. Planta Medica, 54, 10–14.
