Bioassay-directed isolation of falcarindiol and isoacetovanillon from Pycnocycla caespitosa based on KCl-induced contraction in rat uterus smooth muscles

Mostafa Ghanadian, Hassan Sadraei, Gholamreza Asghari, Zinat Abbasi


Hydroalcoholic extract and essential oil of aerial parts of Pycnocycla caespitosa have spasmolytic activity on rat ileum contractions. The objective of this research was to separate fractions of total hydroalcoholic extract of P. caespitosa guided by their spasmolytic activity on rat uterus. Aerial parts of P. caespitosa were extracted with ethanol. The concentrated extract was subjected to column chromatography and thin layer chromatography (TLC) for isolation fractions, then one of the bioactive fractions was subjected to further isolation to find its active components. Five fractions were obtained (Fr.1-Fr.5) and their anti-spasmodic activities were examined on uterus contraction induced by KCl (80 mM) and compared with ritodrine. In addition, spasmolytic effect of Fr.4 (one of the bioactive fractions) was determined on rat uterus induced by oxytocin (0.0005 IU/mL) and compared with ritodrine. Hydroalcoholic extract of P. caespitosa                 (0.032-2 mg/mL) reduced the responses to KCl but the inhibitory effect was not complete with 2 mg/mL extract in the bath. Four fractions (Fr.1, Fr.2, Fr.3 and Fr.4) (32-500 μg/mL) inhibited rat uterus contractions on the uterus while Fr.4 was slightly more active than others (IC50 = 146 ± 23 μg/mL). Falcarindiol and isoacetovanillone were identified from Fr.4 using phytochemical methods including high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) and TLC. In conclusion, in this research bioactivity guided technique was successfully used for separation of active fraction of P. caespitosa. Falcarindiol and isoacetovanillone were identified from the active fraction which inhibited both tonic and rhythmic contractile responses in rat isolated uterus.


Isoacetovanillone; Falcarindiol; Pycnocycla caespitosa; Uterus; Bioactivity; Anti-spasmodic

Full Text:



Mozaffarian V. The family of Umbellifera in Iran. Tehran: Research Institute of Forests and Rangelands; 1983. pp. 1-101.

Sadraei H, Asghari G, Naddafi A. Relaxant effect of essential oil and hydroalcoholic extract of Pycnocycla spinosa Decne. exBoiss on ileum contractions. Phytother Res. 2003;17:645–649.

Sadraei H, Asghari G, poorkhosravi R. Spasmolytic effect of root and aerial parts extract of Pycnocycla spinosa on neural stimulation of rat ileum. Res Pharm Sci. 2011;6(1):43–50.

Sadraei H, Asghari G, Hekmatti AA. Antispasmodic effect of three fractions of hydroalcoholic extract of Pycnocycla spinosa. J Ethnopharmacol. 2003;86:187–190.

Sadraei H, Asghari G, Andisha M. Antispasmodic effect of Pycnocycla spinosa seed and aerial part extract on rat ileum and uterus smooth muscle contractions. Daru. 2008;13:160-163.

Sadraei H, Asghari G, Arabzadah A. Effect of hydroalcoholic extract of Pycnocycla spinosa on rat isolated bladder. Iranian J Pharm Res. 2004;4:237-241.

Sadraei H, Asghari G, Shams M. Antidiarrheal action of hydroalcoholic extract of Pycnocycla spinosa in comparison with loperamide and dicyclomine. Iran J Pharm Res. 2011;10:835–841.

Sadraei H, Asghari G, Behzad S. Bioactivity-guided isolation of spasmolytic components of Pycnocycla spinosa Decne exBoiss. Res Pharm Sci. 2011;6: 81-86.

Ghanadian M, Sadraei H, Yousuf S, Asghari G, Choudhary MI, Jahed M. New diterpene polyester and phenolic compounds from Pycnocycla spinosa Decne. Ex Boiss with relaxant effects on KCl-induced contraction in rat ileum. Phytochemistry Letters. 2014;7:57-61.

Sadraei H, Ghanadian M, Asghari G, Sharifian R. 3,7,10,14,15 pentaacetyl-5-butanoyl-13,17-epoxy-8- myrsinene a novel compound isolated from Pycnocycla spinosa extract with potent antispasmodic and antidiarrheal properties. Res Pharm Sci. 2015;10:55-61.

Sadraei H, Ghanadian M, Asghari G, Madadi E, Azali N. Antispasmodic and antidiarrheal activities of 6-(4-hydroxy-3-methoxyphenyl)-hexanoic acid from Pycnocycla spinosa Decne ex.Boiss. Res Pharm Sci. 2014;9:279-286.

Parsa A. Flora of Iran. Tehran: Tehran University (Place holder 1) Publications; 1960. pp. 783.

Arazi A, Azemi M, Fakhri A. Analgesic effect of hydroalcoholic extract of Pycnocycla caespitosa in rat by formalin test. Jundishapur J Pharm. 2003;5:105-113.

Khodaei M. Assessment effect of hydroalcoholic extract of Pycnocycla caespitosa on karajynan inflammation in male paws rat. Pharm-D Thesis. [In Persion]. Jundishapur University of Medical Sciences. 2012. Identification number. 23668.

Sadraei H, Asghari G, Alipour M. Anti-spasmodic assessment of hydroalcoholic extract and essential oil of aerial part of Pycnocycla caespitosa Boiss. & Hausskn on rat ileum contractions. Res Pharm Sci. 2016;11(1):33-42.

Sadraei H, Shokoohinia Y, Sajjadi SE, Ghadirian B. Antispasmodic effect of osthole and Prangos ferulacea extract on rat uterus smooth muscle motility. Res Pharm Sci. 2012;7:141-149.

Villegas M, Vargas D, Msonthi JD, Marston A, Hostettmann K. Isolation of the antifungal compounds falcarindiol and sarisan from Heteromorpha Trifoliata. Planta Medica. 1988;54:36-37.

Bentley RK, Bhattacharjee D, Jones ER, Thaller V. Natural acetylenes. Part XXVIII. C 17-polyacetylenic alcohols from the Umbellifer Daucus carota L.(carrot): alkylation of benzene by acetylenyl (vinyl) carbinols in the presence of toluene-p-sulphonic acid. J Chem Soc C. 1969;4:685-688.

Fielding L, McKellar SC, Florence AJ. Precision studies in supramolecular chemistry: a 1H-NMR study of hydroxymethoxyacetophennone/β-cyclodextrin complexes. Magnetic Resonance Chem. 2011;49:405-412.

Ikeda S, Tamaoki H. Pharmacological investigation of ritodrine hydrochloride, a β2-adrenoceptor stimulant. Jpn J Pharmacol. 1984;36(4):477-484.

Sadraei H, Ghanadian M, Asghari G, Madadi E. Antispasmodic activity of isovanillin and isoacetovanillon comparison with Pycnocycla spinosa Decne. exBoiss extract on rat ileum. Res Pharm Sci. 2014;9:187-192.

Matsuda H, Murakami T, Nishida N, Kageura T, Yoshikawa M. Vasorelaxant active constituents from the roots of Angelica furcijuga Kitagawa: structures of hyuganins A, B, C, and D. Chem Pharmaceut Bulletin. 2000;48:1429-1435.


  • There are currently no refbacks.

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial 4.0 International License.

Creative Commons LicenseThis work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License which allows users to read, copy, distribute and make derivative works for non-commercial purposes from the material, as long as the author of the original work is cited properly.