Abstract
Water-distilled essential oil of Ferulago macrocarpa (Umbelliferae) fruits was analyzed using GC-MS for the first time. Forty-two components comprising 99.5% of the total oil were identified, of which bornyl acetate (40.8%), 2,3,6-trimethyl benzaldehyde (7.2%), δ-selinene (5.5%), 1,10-di-epi-cubenol (5.1%), germacrene D (3.5%), β-phellandrene (3.5%) and α-pinene (3.4%) were found to be the major components. The oil of F. macrocarpa fruits consisted of 15 monoterpene hydrocarbons (21.4%), 6 oxygenated monoterpenes (42.2%), 17 sesquiterpene hydrocarbons (22.4%) and one oxygenated sesquiterpene (5.1%). Three benzenoid derivatives also comprised 8.4% of the oil. Monoterpenes and sesquiterpenes comprised 63.6% and 27.5% of the F. macrocarpa fruits essential oil respectively; however, bornyl acetate (40.8%) was identified as the most abundant component of the oil.
Keywords: Ferulago macrocarpa; bornyl acetate; 2; essential oil composition; GC/MS; bornyl acetate; 2,3,6-trimethyl benzaldehyde
INTRODUCTION
Apiaceae (Umbelliferae) family comprises 300 genera and 2500-3000 species distributed in most parts of the world(1). The genus Ferulago (Chavil in Persian) consists of about 40 species which are centered in south-west of Asia(2). Seven Ferulago species are also found in the flora of Iran, most of which are endemic(3).
Previous phytochemical studies of Ferulago have led to isolation of various coumarins(4–6) and volatile oils(7–9). Some of the isolated coumarins have shown antimicrobial, antioxidant(10), cytotoxic(11) and acetylcholinesterase inhibitor(12) activities. In addition, the essential oils of many other Ferulago species have exhibited antimicrobial activities(13–16).
Ferulago macrocarpa (Fenzl) Boiss. is a perennial herb which grows in the west of Iran. The plant popularly referred to as Chavil-e-Roshanball in Farsi. A literature survey has revealed that the essential oil of the aerial parts of the plant has shown larvicidal activity(17); however, the available information indicates that the essential oil of F. macrocarpa fruits has not been the subject of any study, and this paper is the first report in this regard.
MATERIALS AND METHODS
Plant material and isolation of the oil
F. macrocarpa fruits collected from Salehabad in Ilam province in the west of Iran in May 2010 at an altitude of ca. 800 m above sea level and the plant identity was confirmed by the Ilam Agricultural and Natural Resource Research Center. Crushed dry fruits of F. macrocarpa were subjected to hydro distillation for 3 h, using a Clevenger-type apparatus, according to the method recomm-ended in the British Pharmacopoeia(18), and the resulting oil was subsequently dried over anhydrous sodium sulfate.
GC/MS analysis
Gas chromatography combined with mass spectrometry was used for the identification of the components. The analysis was performed on an Agilent 5975C mass selective detector coupled with a Hewlett-Packard 6890 gas chromatograph equipped with a HP-5MS capillary column (30 m × 0.25 mm; film thickness 0.25 μm). The oven temperature was programmed from 60 to 280°C at 4°C/min. Helium was used as the carrier gas at a flow rate of 2 ml/min. The injector and detector temperature was 280°C. The MS operating parameters were: ionization voltage 70 eV, ion source temperature 200°C.
Identification of the oil components was based on the retention indices relative to n-alkanes (C8-C24) and computer matching with NIST and Wiley 275 libraries, as well as by the comparison of fragmentation patterns of the mass spectra with those reported in the literature(19,20).
RESULTS
The air-dried fruits of F. macrocarpa yielded 0.8% of a yellowish essential oil. Forty-two components, comprising 99.5% of the total oil, were identified in the F. macrocarpa fruits essential oil. The compounds identified in the oil sample are presented in Table. As it is evident, bornyl acetate (40.8%), 2,3,6-trimethyl benzaldehyde (7.2%), δ-selinene (5.5%), 1,10-di-epi-cubenol (5.1%), germacrene D (3.5%), β-phellandrene (3.5%) and α-pinene (3.4%) were found to be the major components.
Table 1.
Composition of the essential oil of the fruits of Ferulago macrocarpa
The oil of F. macrocarpa fruits consisted of 15 monoterpene hydrocarbons (21.4%), 6 oxygenated monoterpenes (42.2%), 17 sesquiterpene hydrocarbons (22.4%) and one oxygenated sesquiterpene (5.1%). Three benzenoid derivatives also comprised 8.4% of the oil. Monoterpenes and sesquiterpenes comprised 63.6% and 27.5% of the F. macrocarpa fruits essential oil respectively.
DISCUSSION
Essential oil compositions of the aerial parts of some Ferulago species have been reported earlier(8,9,14,15,21–23). There have also been reports on their fruit oil composition. The main constituents of the fruit oils of F.angulata, F. campestris and F. confusa are reported as cis-ocimene (64.8%), myrcene (33.4%) and cis-chrysanthenyl acetate (37.7%), respectively(24–26).
Chemical constituents of the essential oil of the aerial parts of F. macrocarpa have been previously reported. Bornyl acetate (45.7%), borneol (17.2%) and β-gurjunene (9.2%) are the main components of the aerial parts oil(17) which is in accordance with our findings. According to the results of our study, bornyl acetate (40.8%) was found to be the major components of the essential oil of the fruits of F. macrocarpa. 2,3,6-Trimethylbenaldehyde comprising 7.2% of the F. macrocarpa fruits essential oil is not present in the aerial parts essential oil of this herb. 2,3,6-Trimethyl benzaldehyde, the other main volatile oil constituent of the fruits of F. macrocarpa, has been also identified as the major component of the F. asparagifolia (38.9%) and F. longistylis (29.0%) fruit oils(27,28).
CONCLUSION
In summary, the present study, for the first time, showed that the essential oil of F. macrocarpa fruits is mainly composed of terpenoids and benzenoid derivatives were also detected.
ACKNOWLEDGMENT
The authors would like to acknowledge the financial support of the Research Council of Isfahan University of Medical Sciences
REFERENCES
- 1.Heywood VH. Flowering plants of the world. Sydney: Croom Helm; 2001. p. 219. [Google Scholar]
- 2.Rechinger KH. Verlagsanstalt. Graz: Akademische Druck-u; 1987. Flora Iranica, No.162; p. 428. [Google Scholar]
- 3.Mozaffarian V. A dictionary of Iranian plant names. Tehran: Farhang Moaser; 1996. p. 230. [Google Scholar]
- 4.Jimenez B, Grande MC, Anaya J, Torres P, Grande M. Coumarins from Ferulago capillaris and F. brachyloba. Phytochemistry. 2000;53:1025–1031. doi: 10.1016/s0031-9422(99)00524-5. [DOI] [PubMed] [Google Scholar]
- 5.Khalighi-Sigaroodi F, Hadjiakhoondi A, Shafiee A, Mozaffarian VA, Shahverdi AR, Alavi SHR. Phytochemical analysis of Ferulogo Bernardii Tomk and M. Pimen. Daru. 2006;14:214–221. [Google Scholar]
- 6.Sklyar YE, Andrianova VB, Pimenov MG. Coumarins of the roots of Ferulago sylvatica. Chem Nat Comp. 1982;18:488–489. [Google Scholar]
- 7.Erdurak CS, Coskun M, Demirci B, Baser KHC. Composition of the essential oil of fruits and roots of Ferulago isaurica Pesmen and F. syriaca Boiss (Umbelliferae) from Turkey. Flavour Fragr J. 2006;21:118–21. [Google Scholar]
- 8.Kilic CS, Ozkan AMG, Demirci B, Coskun M, Baser KHC. Essential oil composition of four endemic Ferulago species growing in Turkey. Nat Prod Commun. 2010;5:1951–1954. [PubMed] [Google Scholar]
- 9.Akhlaghi H. The essential oils from flowers, stems and leaves of Ferulago angulata from Iran. Chem Nat Comp. 2008;44:396–397. [Google Scholar]
- 10.Basile A, Sorbo S, Spadaro V, Bruno M, Maggio A, Faraone N, Rosselli S. Antimicrobial and antioxidant activities of coumarins from the roots of Ferulago campestris (Apiaceae) Molecules. 2009;14:939–952. doi: 10.3390/molecules14030939. [DOI] [PMC free article] [PubMed] [Google Scholar]
- 11.Rosselli S, Maggio AM, Faraone N, Spadaro V, Morris-Natschke SL, Bastow KF, et al. The cytotoxic properties of natural coumarins isolated from roots of Ferulago campestris (Apiaceae) and of synthetic ester derivatives of aegelinol. Nat Prod Commun. 2009;4:1701–6. [PubMed] [Google Scholar]
- 12.Dall’Acqua S, Maggi F, Minesso P, Salvagno M, Papa F, Vittori S, Innocenti G. Identification of non-alkaloid acetylcholinesterase inhibitors from Ferulago campestris (Besser) Grecescu (Apiaceae) Fitoterapia. 2010;81:1208–1212. doi: 10.1016/j.fitote.2010.08.003. [DOI] [PubMed] [Google Scholar]
- 13.Demircia F, Iscan G, Guven K, Kirimer N, Demircia B, Baser KHC. Antimicrobial activities of Ferulago essential oils. Z. Naturforsch. 2000;55c:886–889. doi: 10.1515/znc-2000-11-1207. [DOI] [PubMed] [Google Scholar]
- 14.Maggi F, Tirillini B, Papa F, Sagratini G, Vittori S, Cresci A, et al. Chemical composition and antimicrobial activity of the essential oil of Ferulago campestris (Besser) Grecescu growing in central Italy. Flavour Fragr J. 2009;24:309–315. [Google Scholar]
- 15.Demetzos C, Perdetzoglou D, Gazouli M, Tan K, Economakis C. Chemical analysis and antimicrobial studies on three species of Ferulago from Greece. Planta Med. 2000;66:560–3. doi: 10.1055/s-2000-8652. [DOI] [PubMed] [Google Scholar]
- 16.Taran M, Ghasempour HR, Shirinpour E. Antimicrobial activity of essential oil of Ferulago angulata subsp. carduchorum. Jundishapur J Microbiol. 2013;3:10–14. [Google Scholar]
- 17.Hadjiakhoondi A, Aghel N, Etemadi R. Chemical and biological study of essential oil of Ferulago macrocarpa (Fenzl) Boiss. Hamdard Med. 2002;45:35–38. [Google Scholar]
- 18.British pharmacopoeia. Vol. 2. London: HMSO Publication; 1988. pp. A137–A138. [Google Scholar]
- 19.Adams RP. Identification of essential oil components by gas chromatography / mass spectroscopy. Illinois: Allured Publishing Corporation; 1995. [Google Scholar]
- 20.Swigar AA, Silverstein RM. Monoterpenes, infrared, mass, 1H-NMR, 13C-NMR spectra and Kovats indices. Wisconsin: Aldrich Chemical Company Inc; 1981. [Google Scholar]
- 21.Khalighi-Sigaroodi F, Hadjiakhoondi A, Shahverdi AR, Mozaffarian V, Shafiee A. Chemical composition and antimicrobial activity of the essential oil of Ferulogo Bernardii Tomk. and M. Pimen. Daru. 2005;13:100–104. [Google Scholar]
- 22.Samiee K, Akhgar MR, Rustaiyan A, Masoudi S. Composition of the volatiles of Ferulago carduchorum Boiss. et Hausskn. and Levisticum officinale Koch. obtained by hydrodistillation and extraction. J Essent Oil Res. 2006;18:19–21. [Google Scholar]
- 23.Ruberto G, Biondi D, Renda A. The composition of the volatile oil of Ferulago nodosa obtained by steam distillation and supercritical carbon dioxide extraction. Phytochem Anal. 1999;10:241–246. [Google Scholar]
- 24.Ghasempour HR, Shirinpour E, Heidari H. Analysis by gas chromatography-mass spectrometry of essential oil from seeds and aerial parts of Ferulago angulata (Schlecht.) Boiss. gathered in Nevakoh and Shahoo, Zagross mountain, west of Iran. Pakistan J Biol Sci. 2007;10:814–817. doi: 10.3923/pjbs.2007.814.817. [DOI] [PubMed] [Google Scholar]
- 25.Cecchini C, Coman MM, Cresci A, Tirillini B, Cristalli G, Papa F, et al. Essential oil from fruits and roots of Ferulago campestris (Besser) Grecescu (Apiaceae), composition and antioxidant and anti-Candida activity. Flavour Fragr. J. 2010;25:493–502. [Google Scholar]
- 26.Kurkcuoglu M, Iscan G, Demirci F, Baser KHC, Mayer H, Erdogan E. Composition and antibacterial activity of the essential oil of Ferulago confusa Velen. J Essent Oil Res. 2010;22:490–492. [Google Scholar]
- 27.Baser KHC, Demirci B, Duman H. Composition of the essential oil of Ferulago asparagifolia Boiss. from Turkey. J Essent Oil Res. 2001;13:134–135. [Google Scholar]
- 28.Ozkan AMG, Demirci B, Demirci F, Baser KHC. Composition and antimicrobial activity of essential oil of Ferulago longistylis Boiss. fruits. J Essent Oil Res. 2008;20:569–573. [Google Scholar]