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Antiproliferative evaluation of terpenoids and terpenoid coumarins from Ferulago macrocarpa (Fenzl) Boiss. fruits.

Sajjadi SE, Jamali M, Shokoohinia Y, Abdi G, Shahbazi B, Fattahi A - Pharmacognosy Res (2014 Oct-Dec)

Bottom Line: The objective was to isolate and characterize terpenoids and coumarins from the acetone extract of F. macrocarpa fruits and to evaluate their antiproliferative effects on several cell lines.Six compounds including bornyl acetate (1), 1,10-di-epi-cubenol (2), stigmasterol (3) and three coumarins grandivittin (4), prantschimgin (5) and 4"-hydroxygrandivittin (7) along with mixtures of feruloyl derivatives (6a-6c) have been purified.Their structures were established by spectroscopic methods including nuclear magnetic resonance and MS analyses.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacognosy, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, Iran.

ABSTRACT

Background: Ferulago macrocarpa is a plant used as flavoring agent and protectant in the food industry and as a folk medicinal plant in Iran with no available information on its chemical identity. Ferulago spp. showed to contain biologically terpenoids and coumarins.

Objective: The objective was to isolate and characterize terpenoids and coumarins from the acetone extract of F. macrocarpa fruits and to evaluate their antiproliferative effects on several cell lines.

Materials and methods: A series of normal and reverse phase gravity and high-performance liquid chromatography analyses were used to purify constituents. Compounds 1-5 and 7 were evaluated for their cytotoxic effects on MCF-7, HT-29 and H-1299 cell lines.

Results: Six compounds including bornyl acetate (1), 1,10-di-epi-cubenol (2), stigmasterol (3) and three coumarins grandivittin (4), prantschimgin (5) and 4"-hydroxygrandivittin (7) along with mixtures of feruloyl derivatives (6a-6c) have been purified. Their structures were established by spectroscopic methods including nuclear magnetic resonance and MS analyses. Compound 2 showed moderate cytotoxicity effect with IC50 values of 5.0 and 6.7 mM on MCF-7 and HT-29, respectively.

Conclusion: 1,10-di-epi-Cubenol could be considered as a potential proliferation inhibitor of MCF-7 and HT-29 cell lines.

No MeSH data available.


Related in: MedlinePlus

Chemical structure of terpenoids and terpenoid coumarins of Ferulago macrocarpa
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Figure 1: Chemical structure of terpenoids and terpenoid coumarins of Ferulago macrocarpa

Mentions: The air dried fruits of F. macrocarpa (500 g) were exhaustively macerated with acetone at room temperature. After the removal, the solvent in vacuo, the residue (87.5 g) was dissolved in methanol, kept in − 20°C and underwent chill filtration to get rid of long chain triglycerides. Defatted extract (75 g) was purified by vacuum liquid chromatography using mixtures of heptane (H) and EtOAc (E) (10:0-0:10) to afford 7 fractions (A–G). Fraction A was fats. Fraction B (1.5 g) was purified through open column chromatography on silica using 5-2% EtOAc in toluene to get pure 13 mg of compound 1 [Figure 1]. Other subfractions of B were mixed and purified using normal phase HPLC (hexane: EtOAc, 80:20-90:10) resulted in compound 2. Fraction C was mixture of B and D. Fraction D was subjected to several normal phase column chromatography and HPLC analyses, were led to isolation of a plant sterol, compound 3 (200 mg) and a pure coumarin, compound 4 (H: EtOAc, 50:50, 9 mg). Fraction E (H: E, 8:2) rendered a mass of impure crystals in which recrystallization resulted in a pure compound 5. Mother liquor of 1E was mixed with 1F and fractionated on normal phase open column and HPLC analyses to get mixtures of compounds 6a-6c (10 mg). Fraction G along with the most polar subfractions of other fractions were subjected to reversed-phase solid phase extraction using mixtures of MeOH and water, and finally furnished with HPLC analysis using RP18 column and 60-100% MeOH in H2 O solvent system to get compound 7 (5 mg).


Antiproliferative evaluation of terpenoids and terpenoid coumarins from Ferulago macrocarpa (Fenzl) Boiss. fruits.

Sajjadi SE, Jamali M, Shokoohinia Y, Abdi G, Shahbazi B, Fattahi A - Pharmacognosy Res (2014 Oct-Dec)

Chemical structure of terpenoids and terpenoid coumarins of Ferulago macrocarpa
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4660510&req=5

Figure 1: Chemical structure of terpenoids and terpenoid coumarins of Ferulago macrocarpa
Mentions: The air dried fruits of F. macrocarpa (500 g) were exhaustively macerated with acetone at room temperature. After the removal, the solvent in vacuo, the residue (87.5 g) was dissolved in methanol, kept in − 20°C and underwent chill filtration to get rid of long chain triglycerides. Defatted extract (75 g) was purified by vacuum liquid chromatography using mixtures of heptane (H) and EtOAc (E) (10:0-0:10) to afford 7 fractions (A–G). Fraction A was fats. Fraction B (1.5 g) was purified through open column chromatography on silica using 5-2% EtOAc in toluene to get pure 13 mg of compound 1 [Figure 1]. Other subfractions of B were mixed and purified using normal phase HPLC (hexane: EtOAc, 80:20-90:10) resulted in compound 2. Fraction C was mixture of B and D. Fraction D was subjected to several normal phase column chromatography and HPLC analyses, were led to isolation of a plant sterol, compound 3 (200 mg) and a pure coumarin, compound 4 (H: EtOAc, 50:50, 9 mg). Fraction E (H: E, 8:2) rendered a mass of impure crystals in which recrystallization resulted in a pure compound 5. Mother liquor of 1E was mixed with 1F and fractionated on normal phase open column and HPLC analyses to get mixtures of compounds 6a-6c (10 mg). Fraction G along with the most polar subfractions of other fractions were subjected to reversed-phase solid phase extraction using mixtures of MeOH and water, and finally furnished with HPLC analysis using RP18 column and 60-100% MeOH in H2 O solvent system to get compound 7 (5 mg).

Bottom Line: The objective was to isolate and characterize terpenoids and coumarins from the acetone extract of F. macrocarpa fruits and to evaluate their antiproliferative effects on several cell lines.Six compounds including bornyl acetate (1), 1,10-di-epi-cubenol (2), stigmasterol (3) and three coumarins grandivittin (4), prantschimgin (5) and 4"-hydroxygrandivittin (7) along with mixtures of feruloyl derivatives (6a-6c) have been purified.Their structures were established by spectroscopic methods including nuclear magnetic resonance and MS analyses.

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacognosy, School of Pharmacy and Pharmaceutical Sciences, Isfahan University of Medical Sciences, Isfahan, Iran.

ABSTRACT

Background: Ferulago macrocarpa is a plant used as flavoring agent and protectant in the food industry and as a folk medicinal plant in Iran with no available information on its chemical identity. Ferulago spp. showed to contain biologically terpenoids and coumarins.

Objective: The objective was to isolate and characterize terpenoids and coumarins from the acetone extract of F. macrocarpa fruits and to evaluate their antiproliferative effects on several cell lines.

Materials and methods: A series of normal and reverse phase gravity and high-performance liquid chromatography analyses were used to purify constituents. Compounds 1-5 and 7 were evaluated for their cytotoxic effects on MCF-7, HT-29 and H-1299 cell lines.

Results: Six compounds including bornyl acetate (1), 1,10-di-epi-cubenol (2), stigmasterol (3) and three coumarins grandivittin (4), prantschimgin (5) and 4"-hydroxygrandivittin (7) along with mixtures of feruloyl derivatives (6a-6c) have been purified. Their structures were established by spectroscopic methods including nuclear magnetic resonance and MS analyses. Compound 2 showed moderate cytotoxicity effect with IC50 values of 5.0 and 6.7 mM on MCF-7 and HT-29, respectively.

Conclusion: 1,10-di-epi-Cubenol could be considered as a potential proliferation inhibitor of MCF-7 and HT-29 cell lines.

No MeSH data available.


Related in: MedlinePlus