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��ࡱ�>��	������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������������	���Hbjbj����4�����@�������^^^^^����rrrr�.4r=�bbbbb===�<�<�<�<�<�<�<$�>��A�<^� ==� � �<^^bb��<�9�9�9� |^b^b�<�9� �<�9�9�9b������8m��ro0��9q<�<0=�9�B-72�B�9�9��B^I:(=n���9gd�(===�<�<_9j====� � � � ���������������������������������������������������������������������B=========$:Influence of extraction methods on the composition of essential oils of Achillea millefolium L. from Lithuania
Hanen Marzoukia*, Alessandra Pirasb, Silvia Porceddab, Danilo Falconieric, Edita Bagdonaited

aFacult� des sciences de Gafsa, Tunis, Tunisia, e-mail�: hanen_marzouki7@yahoo.fr; 
bDipartimento di Scienze Chimiche e Geologiche, Universit� degli Studi di Cagliari, Cittadella Universitaria di Monserrato, SP 8 Monserrato-Sestu Km 0,700, 09042, Monserrato, Italy; 
cIstituto Tecnico Industriale Statale �Michele Giua�, Via Montecassino, 09100 Cagliari, Italy;
dDepartment of Economic Botany, Institute of Botany, Nature Research Centre, Vilnius, LT-08406, Lithuania;

Abstract
In this study, flowering aerial parts of Achillea millefolium were used as a matrix for supercritical CO2 extraction (SFE) of volatile oil. The collected extracts were analyzed by GC-FID and GC-MS methods and their composition were compared with that of the essential oil isolated by hydrodistillation (HD). The differences observed between the composition of the SFE volatile concentrates and of the HD oil were relevant. Indeed, the SFE volatile oil had a pale yellow colour whereas the HD oil had a blue colour due to the presence of chamazulene (48.0 % vs. 4.3 %). Other important constituents of HD oil were (E)-caryophyllene (19.5 %) and (-muurolene (13.1 %). CO2 supercritical extract was dominated by (E)-caryophyllene (26.0 %), (-muurolene (22.0 %), caryophyllene oxide (8.1 %). 
Key words. Achillea millefolium L., hydrodistillation, supercritical CO2 extraction, essential oil, chamazulene.





1. Introduction
Achillea millefolium L. is a well-known aromatic and medicinal plant, widely used in folk medicine against gastrointestinal disorders and lack of appetite. The chemical composition of A. millefolium essential oil was investigated in several countries and a high chemical variability were observed (Pino et al. 1998; Nemet. 2005; Judzentiene et al 2010).
Different studies showed that the chemical composition depends on many parameters as the geographical origin of the plant, the part of the plant analyzed (Couladis et al. 2002; Perry et al. 1996) and the technique of extraction (Ganou 1993; Matelic 2001). Although distillation is a very convenient method for extracting essential oils, some disadvantages are caused by the artefacts produced during the process, especially when thermolabile components are involved. Some authors have reported that A. millefolium from some habitats of Lithuania contain proazulenes, which produced azulenes during hydrodistillation. Several phytochemical studies, previously focused mainly on azulenes and proazulenes (sesquiterpenic lactones) as the most characteristic compounds in yarrow plants (Radusiene et al. 2005; Kastner et al. 1992). However, the inflorescence oils of pink flowers collected in 14 habitats from Lithunia, did not contain chamazulene among the main constituents. Nine oils were azulene-free, four samples contained ( 0.5 % of chamazulene, and only one oil contained 5.7 % of it. (Jud�entien� et al. 2004). Also Orav et al. (2006) found in that chamazulene was within the three principal constituents only in a small part of investigated A. millefolium essential oils.
Extraction by carbon dioxide in the supercritical state is a process that offers many advantages in obtaining volatile extracts or aroma substances for human nutrition and for the pharmaceutical and perfume industries. Indeed, the mild extraction conditions give assurance against chemical reactions not taking place during the process. This technique avoids the degradative thermal processes, hydrolysis, isomerization and racemization (Marongiu et al. 2003; Marongiu et al. 2012; Porcedda et al. 2009). 
This paper reports the composition of the volatile oils of Lithuanian A. millefolium extracted by mean of supercritical CO2, in comparison with that of the HD oil.

2. Results and Discussion
Table 1 shows the detailed identification and area percentage of compounds found in the oil isolated by supercritical extraction and by hydrodistillation. The main compounds responsible for the fragrance of A. millefolium oil were: (E)-caryophyllene, 26.0 % in SFE versus 19.5 % in HD; (-muurolene, 22.0 % in SFE versus 13.1 % in HD; caryophyllene oxide, 8.1 % in SFE versus 5.6 % in HD and chamazulene, 4.3 % in SFE versus 48.2 % in HD. 
The oil obtained by supercritical extraction gave a yield (w/w) of 0.12 % while the one obtained by hydrodistillation a yield of 0.07 %.
The oil composition is variable according to the method of extraction and the main differences in oil quality are clear on comparing their color: the HD oil had a blue color due to chamazulene in aqueous medium, whereas the SFE extract was yellow. In confirmation of this degradative phenomenon,  the SFE oil was water diluted and heated, in bringing a change of its color from yellow to blue. Indeed, the chamazulene has subbasic properties and in acid medium, CO2 medium, it originates a chamazulenio cation colorless (Marongiu et al. 2006).
In previous investigations, it was been reported that fourteen out of the twenty oils collected from five habitats in Lithuania, did not contain chamazulene (Judzentiene et al. 2010). This is not surprising as there are some studies supporting that environmental variations affect content and composition of volatile oil in medicinal and aromatic plants (Malik et al. 2009; Marzouki et al. 2011).
Comparing our results with A. millefolium that of oils from other countries earlier reported, it is evident that these oils are quite different. Recently, Falconieri et al.(2011) found that the volatile extracts obtained from the Sardinian A. millefolium were characterized by high content of (-asarone (25.6-33.3 %, in the SFE extract and in the HD oil, respectively), (-bisabolene (27.3-16.6 %) and (-pinene (10.0-17.0 %). Whereas in the work of  Jaimand et al.( 2006), the major constituents of the leaf oil of Iranian ssp obtained by different methods were: chamazulene, isoborneol, p-cymene and germacerene. Essential oils of A. millefolium ssp. elbursensis flowers isolated by hydrodistillation indicated chamazulene (54 %), camphor (8 %) and isoborneol (7.6 %) as main constituents.  While the leaf oil contained chamazulene (35 %), isoborneol (18 %) and p-cymene (15 %) (Jaimand et al, 2006). The essential oil of A. millefolium grown under tropical conditions was rich in sabinene, 1,8-cineole, borneol, bornyl acetate, (-pinene, (-pinene, terpinine-4-ol and chamazulene (Nadim et al. 2011). 
In conclusion, the data obtained in this study showed a remarkable quantitative variation of constituents in the oil according to the method of extraction. Essential oils that contain chamazulene are important in therapeutic applications because of its apparent radical scavenging activity (El Beyrouthy et al. 2011), so in a second step biological activity potential must be estimated.
3. Experimental
Plants Materials
The flowering aerial parts of Achillea millefolium were collected in July 2013 from its natural habitat in Lithuania. Before utilization, the vegetable matter was ground with a Malavasi mill (Bologna, Italy) taking care to avoid overheating and the particles sizes were in the range (250(425) (m.
Hydrodistillation
Hydrodistillation (HD) was performed for 3 h in a circulatory Clevenger-type apparatus according to the procedure described in the European Pharmacopoeia (European Pharmacopoeia, 1997).
SFE extraction
Supercritical CO2 extractions were performed in a laboratory apparatus, equipped with a 320 cm3 extraction vessel and two separator vessels of 300 and 200 cm3 respectively connected in series. Extraction was carried out in a semi batch mode: batch charging of vegetable matter and continuous flow solvent. The Achillea millefolium oil was obtained working at 90 bar and 40 �C (CO2 density, (CO2 = 0.287 g cm-3) in the extraction vessel, at 90 bar and �10 �C in the first separator and at 20 bar and 15�C in the second one. 
GC/FID and GC/MS analysis of the volatile extracts 
Qualitative analysis were carried out by means of gas chromatography-mass spectrometry (GC/MS) and the quantitative composition were accomplished by gas chromatography (GC/FID).
GC/MS analyses were carried out in a gas chromatograph (Agilent, Model 6890N, Palo Alto, CA) equipped with a split-splitless injector, an autosampler Agilent model 7683 and two different Agilent fused silica capillary columns (30 m � 0.25 mm i.d., film thickness 0.25 (m) of different polarities (HP-5, 5 % phenyl-methylpolysiloxane;  DB-WAXetr, polyethylene glycol).
GC conditions used were: programmed heating from 60 to 250 �C at 3 �C/min followed by 20 min under isothermal conditions. The injector was maintained at 250 �C. Helium was the carrier gas at 1.0 mL/min; the sample (1 (L) was injected in the split mode (1:10). The GC was fitted with a quadrupole mass spectrometer, MS, Agilent model 5973 detector. MS conditions were as follows: ionization energy 70 eV, electronic impact ion source temperature 200 �C, quadrupole temperature 150 �C, scan rate 3.2 scan/sec, mass range 30(480 u. Software adopted to handle mass spectra and chromatograms was ChemStation. Samples were run in chloroform with a dilution ratio of 1:100. The volatile compounds were identified by both their retention indices and their mass spectra. Retention indices (Kovats 1965), calculated by linear interpolation relative to retention times of a series of n-alkanes, were compared with those of authenticated samples from our database. Mass spectra were compared with reference spectra from a home-made library or from literature data (NIST/EPA/NIH Mass spectral library 2005; Adams 2007). 
Analytical GC/FID was carried out in a gas chromatograph (Agilent, Model 7890A, Palo Alto, CA), equipped with a flame ionization detector (FID), an autosampler (Agilent, Model 7683B), Agilent HP5 fused silica column (5 % phenyl-methylpolysiloxane), 30 m � 0.25 mm i.d., film thickness 0.25 (m, and a Agilent ChemStation software system. Oven temperature was settled at 60 �C, raising at 3 �C/min to 250 �C and then held 20 min at 250 �C; injector temperature: 250 �C; carrier gas: helium at 1.0 mL/min; splitting ratio 1:10; detectors temperature: 300 �C.
Percentage of individual components was calculated based on GC/FID peak areas without FID response factor correction. 

References  

Adams RP. 2007. Identification of essential oil components by gas chromatography/mass spectroscopy. Carol Stream, Illinois, USA: Allured Publishing Corporation.

Council of Europe. 1997. European Pharmacopoeia, third ed., Council of Europe Press, Strasbourg, p. 121-122.

Kovats E. 1965. Gas chromatographyc characterization of organic substances in the retention index system. Adv. Chromatogr. 1: 229-247.

NIST/EPA/NIH. 2005. Mass spectral library; National Institute of Standard and Technology, Gaithersburg.

Marongiu B, Piras A, Porcedda S. 2003. Supercritical extraction of essential oils from natural matrices. Research Advanced. in Agricultural & Food Chemistry. 4: 53-62.

Marongiu B, Piras A, Porcedda S, Falconieri D. 2012. Traditional and Modern Methods for the Preparation of Essential Oils in Essential Oils as Natural Food Additives: Composition, Applications, Antioxidant and Antimicrobial Properties; L. Nova Science Publishers, New York, Valgimigli (Ed.).pp 25-45.

Porcedda S, Piras A, Falconieri D, Marongiu B. 2009. Supercritical fluid extraction and fractionation of essential oils and related products from natural matrices. Essential oils and aromas. Green extraction and application. Farid Chemat Editor. HKB, India. pp. 66-83.

Falconieri D, Piras A, Porcedda S, Marongiu B, Gon�alves MJ, Cabral C, Cavaleiro C, Salgueiro L. 2011. Chemical Composition and Biological Activity of the Volatile Extracts of Achillea millefolium. Natural Product Communications. 6 (10): 1527-1530.

El Beyrouthy M, Arnold-Apostolides N, Labaki M, Cazier F, Najm, S, AbouKa�s A. 2011. Chemical composition of the essential oil of the Artemisia arborescens L. growing wild in Lebanon Lebanese. Sci. J. 12, 71.

Jaimand K., Rezaee M.B., Mozaffarian V. 2006. Chemical constituents of the leaf and flower oils from Achillea millefolium ssp. elbursensis Hub.-Mor. from Iran rich in chamazulene, J. Essent. Oil Res., 18, 293-295

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Table 1: Retention index and chromatographic area percentages of compounds identified in Achillea millefolium volatile oil extracted by SFE at 90 bar 40�C (SFE) and by hydrodistillation (HD) 
COMPOUND RI HD SFE sabinene 976 tr tr (-pinene 979 1.5 0.6 1,8-cineole 1034 1.91.5 cis-chrysanthenol 1164 1.43.0 borneol 1167 tr 1.1 (-terpineol 1191 tr 2.6 trans-carveol  1210 tr 1.5 cis-chrysanthenyl acetate 1263 tr tr (-bourbonene 1384 tr 1.0 (E)-caryophyllene 1418 19.526.0 (-humulene 1453 2.6 3.7 (-muurolene 1480 13.1 22.0 (-zingiberene 1495 1.5 2.4 (-cadinene 1523 1.9 2.5 (E)-nerolidol 1564 1.3 1.8 germacrene D-4-ol 1574 tr 1.0 caryophyllene oxide 1581 5.6 8.1 viridflorol 1589 1.5 2.410-epi-gamma-eudesmol 1622 tr 1.1 3-iso-thujopsanone 1644 tr 1.2 selin-11-en-4-(-ol 1652 tr 2.0 14-hydroxy-9-epi-(E)-caryophyllene 1670 tr 1.4 n.i. 1691 tr 5.8 chamazulene 1726 48.2 4.3 n.i. 1755 tr 2.8 Total identified100.0 91.1Hydrocarbon monoterpenes, HM1.50.6 Oxygenated monoterpenes, OM3.3 9.7Hydrocarbon sesquiterpenes, HS38.757.6 Oxygenated sesquiterpenes, OS8.4 18.9 Azulenes48.2 4.3 tr: trace, i.e., percentage lower than 0.1%. n.i.: not identified compound.








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