Isolation of essential oil from different plants and herbs by supercritical fluid extraction.

Supercritical fluid extraction (SFE) is an innovative, clean and environmental friendly technology with particular interest for the extraction of essential oil from plants and herbs. Supercritical CO(2) is selective, there is no associated waste treatment of a toxic solvent, and extraction times are moderate. Further, supercritical extracts were often recognized of superior quality when compared with those produced by hydro-distillation or liquid-solid extraction. This review provides a comprehensive and updated discussion of the developments and applications of SFE in the isolation of essential oils from plant matrices. SFE is normally performed with pure CO(2) or using a cosolvent; fractionation of the extract is commonly accomplished in order to isolate the volatile oil compounds from other co-extracted substances. In this review the effect of pressure, temperature and cosolvent on the extraction and fractionation procedure is discussed. Additionally, a comparison of the extraction yield and composition of the essential oil of several plants and herbs from Lamiaceae family, namely oregano, sage, thyme, rosemary, basil, marjoram and marigold, which were produced in our supercritical pilot-plant device, is presented and discussed.

[1]  Ž. Knez,et al.  Supercritical fluid extraction of chamomile flower heads: Comparison with conventional extraction, kinetics and scale-up , 2007 .

[2]  M. Komaitis,et al.  Composition of the essential oil of marjoram (Origanum majorana L.) , 1992 .

[3]  M. Koel,et al.  Identification and characterization of supercritical fluid extracts from herbs , 2004 .

[4]  G. Reglero,et al.  Fractionation of thyme (Thymus vulgaris L.) by supercritical fluid extraction and chromatography , 2011 .

[5]  J. Deli,et al.  HPLC study on the carotenoid composition of Calendula products. , 2002, Journal of biochemical and biophysical methods.

[6]  M. Saito,et al.  Fractionation of lemon-peel oil by semi-preparative supercritical fluid chromatography , 1990 .

[7]  I. Zizović,et al.  Supercritical carbon dioxide extraction of sesquiterpenes from valerian root , 2007 .

[8]  M. Boussaid,et al.  Essential oils composition in two Rosmarinus officinalis L. varieties and incidence for antimicrobial and antioxidant activities. , 2010, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[9]  Y. Yamini,et al.  Comparison of essential oil compositions of Salvia mirzayanii obtained by supercritical carbon dioxide extraction and hydrodistillation methods , 2008 .

[10]  E. Ibáñez,et al.  Isolation of functional ingredients from rosemary by preparative-supercritical fluid chromatography (Prep-SFC). , 2006, Journal of pharmaceutical and biomedical analysis.

[11]  E. Reverchon,et al.  Rose Concrete Fractionation by Supercritical CO2 , 1996 .

[12]  R. Yunes,et al.  Marigold (Calendula officinalis L.) oleoresin: Solubility in SC-CO2 and composition profile , 2007 .

[13]  M. Mosaddak,et al.  Chemical composition and antimicrobial activities of two aromatic plants: Origanum majorana L. and O. compactum Benth , 1996 .

[14]  Y. Yamini,et al.  Comparative analysis of the oil and supercritical CO2 extract of Artemisia sieberi , 2007 .

[15]  M. Suhaj.  Spice antioxidants isolation and their antiradical activity: a review , 2006 .

[16]  B. Simándi,et al.  Supercritical carbon dioxide extraction and fractionation of oregano oleoresin , 1998 .

[17]  S. Bandyopadhyay,et al.  Extraction of cashew (Anacardium occidentale) nut shell liquid using supercritical carbon dioxide. , 2006, Bioresource technology.

[18]  Farid Chemat,et al.  Applications of ultrasound in food technology: Processing, preservation and extraction. , 2011, Ultrasonics sonochemistry.

[19]  V. Ferraro,et al.  Supercritical carbon dioxide extraction of volatile oil from Italian coriander seeds , 2008 .

[20]  G. Reglero,et al.  Supercritical Fractionation of Rosemary Extracts to Improve the Antioxidant Activity , 2012 .

[21]  N. Mimica-Dukić,et al.  Antimicrobial and antioxidant activities of Melissa officinalis L. (Lamiaceae) essential oil. , 2004, Journal of agricultural and food chemistry.

[22]  P. Cabras,et al.  Chemical composition and antioxidant, antimicrobial, and antifungal activities of the essential oil of Achillea ligustica all. , 2005, Journal of agricultural and food chemistry.

[23]  C. Peters,et al.  Experimental determination of high-pressure phase equilibria of the ternary system carbon dioxide + limonene + linalool , 2005 .

[24]  Spiridon Kintzios,et al.  Sage : The Genus Salvia , 2000 .

[25]  G. Reglero,et al.  Kinetic study of the supercritical CO2 extraction of different plants from Lamiaceae family , 2012 .

[26]  I. Zizović,et al.  The analysis of simultaneous clove/oregano and clove/thyme supercritical extraction , 2011 .

[27]  M. Díaz-Maroto,et al.  Volatile components and key odorants of fennel (Foeniculum vulgare Mill.) and thyme (Thymus vulgaris L.) oil extracts obtained by simultaneous distillation-extraction and supercritical fluid extraction. , 2005, Journal of agricultural and food chemistry.

[28]  Jae-Jin Shim,et al.  Solubility in Supercritical Carbon Dioxide , 2006 .

[29]  F. Raofie,et al.  Application of response surface methodology and central composite design for the optimisation of supercritical fluid extraction of essential oils from Myrtus communis L. leaves , 2011 .

[30]  M. Ashokkumar,et al.  Ultrasonic enhancement of the supercritical extraction from ginger. , 2006, Ultrasonics sonochemistry.

[31]  Takahiro Nakamura,et al.  Novel fractionation method for squalene and phytosterols contained in the deodorization distillate of rice bran oil. , 2010, Journal of oleo science.

[32]  H. Sovová,et al.  Supercritical CO2 extraction of Salvia officinalis L , 2007 .

[33]  A. Palavra,et al.  Supercritical CO2 extraction of Thymus zygis L. subsp. sylvestris aroma , 2000 .

[34]  M. Hamburger,et al.  Supercritical carbon dioxide extraction of selected medicinal plants--effects of high pressure and added ethanol on yield of extracted substances. , 2004, Phytochemical analysis : PCA.

[35]  Mehmet Musa Özcan,et al.  Comparative essential oil composition of flowers, leavesand stems of basil (Ocimum basilicum L.) used as herb. , 2008, Food chemistry.

[36]  E. Reverchon,et al.  Isolation of Clove Bud and Star Anise Essential Oil by Supercritical CO2Extraction , 1998 .

[37]  G. Mittal,et al.  Solubility of Carotenoids in Supercritical CO2 , 2007 .

[38]  Y. Yamini,et al.  Supercritical carbon dioxide extraction of Mentha pulegium L. essential oil. , 2004, Talanta.

[39]  P. Winterhalter,et al.  In vitro radical scavenging activity of essential oils from Columbian plants and fractions from oregano (Origanum vulgare L.) essential oil , 2002 .

[40]  A. Stoyanova,et al.  Chemical composition and antioxidant properties of clove leaf essential oil. , 2006, Journal of agricultural and food chemistry.

[41]  M. Díaz-Maroto,et al.  Supercritical carbon dioxide extraction of volatiles from spices. Comparison with simultaneous distillation-extraction. , 2002, Journal of chromatography. A.

[42]  C. Chyau,et al.  The essential oil of Glossogyne tenuifolia , 2007 .

[43]  L. Lamberti,et al.  Supercritical deterpenation of lemon essential oil, experimental data and simulation of the semicontinuous extraction process , 2001 .

[44]  T. Shibamoto,et al.  Identification of volatile components in basil Ocimum basilicum L and thyme leaves Thymus vulgaris L and their antioxidant properties , 2005 .

[45]  D. Sattelle,et al.  Thymol, a constituent of thyme essential oil, is a positive allosteric modulator of human GABAA receptors and a homo‐oligomeric GABA receptor from Drosophila melanogaster , 2003, British journal of pharmacology.

[46]  F. Sukan,et al.  In vitro antioxidant activities of Rosmarinus officinalis extracts treated with supercritical carbon dioxide , 2007 .

[47]  E. Reverchon,et al.  Isolation of eucalyptus oil by supercritical fluid extraction , 1999 .

[48]  H. Sovová,et al.  Essential oils from seeds: solubility of limonene in supercritical CO2 and how it is affected by fatty oil , 2001 .

[49]  E. Ibáñez,et al.  Sub- and supercritical fluid extraction of functional ingredients from different natural sources: Plants, food-by-products, algae and microalgae: A review , 2006 .

[50]  M. Eberlin,et al.  Sweet Basil (Ocimum basilicum) Extracts Obtained by Supercritical Fluid Extraction (SFE): Global Yields, Chemical Composition, Antioxidant Activity, and Estimation of the Cost of Manufacturing , 2008 .

[51]  M. Meireles,et al.  Supercritical fluid extraction from Lippia alba: global yields, kinetic data, and extract chemical composition , 2005 .

[52]  W. O. Lundberg,et al.  THE ANTIOXIDANT PROPERTIES OF NATURAL SPICESa,b , 1952 .

[53]  D. Skala,et al.  Extraction of sage (Salvia officinalis L.) by supercritical CO2: Kinetic data, chemical composition and selectivity of diterpenes , 2010 .

[54]  B. Simándi,et al.  Essential oil composition and antimicrobial activity of Origanum majorana L. extracts obtained with ethyl alcohol and supercritical carbon dioxide , 2005 .

[55]  The effects of temperature and pressure on the characteristics of the extracts from high-pressure CO(2) extraction of Majorana hortensis Moench. , 2003, Journal of agricultural and food chemistry.

[56]  I. Zizović,et al.  Supercritical carbon dioxide extraction of carrot fruit essential oil: Chemical composition and antimicrobial activity , 2007 .

[57]  G. Curcuruto,et al.  Screening of the essential oil composition of wild Sicilian rosemary , 2010 .

[58]  Guillermo Reglero,et al.  In vitro antioxidant analysis of supercritical fluid extracts from rosemary (Rosmarinus officinalis L.) , 2005 .

[59]  Shaokun Tang,et al.  Comparison of essential oils of clove buds extracted with supercritical carbon dioxide and other three traditional extraction methods , 2007 .

[60]  E. LaVoie,et al.  Antioxidative Phenolic Compounds from Sage (Salvia officinalis) , 1998 .

[61]  Phineas Masango,et al.  Cleaner production of essential oils by steam distillation , 2005 .

[62]  M Vinatoru,et al.  An overview of the ultrasonically assisted extraction of bioactive principles from herbs. , 2001, Ultrasonics sonochemistry.

[63]  E. Fukusaki,et al.  Separation of hydrophobic metabolites using monolithic silica column in high-performance liquid chromatography and supercritical fluid chromatography. , 2009, Journal of separation science.

[64]  B. Simándi,et al.  Antioxidant activity of pilot-plant alcoholic and supercritical carbon dioxide extracts of thyme , 2001 .

[65]  M. Valcárcel,et al.  Determination of the Carnosic Acid Content in Wild and Cultivated Rosmarinus officinalis , 1998 .

[66]  M. Sanz,et al.  Solubility of three hydroxycinnamic acids in supercritical carbon dioxide , 2003 .

[67]  M. Saito,et al.  New double-stage separation analysis method: directly coupled laboratory-scale supercritical fluid extraction-supercritical fluid chromatography, monitored with a multiwavelength ultraviolet detector , 1985 .

[68]  A. Figiel,et al.  Composition of rosemary essential oil (Rosmarinus officinalis) as affected by drying method , 2010 .

[69]  E. Ibáñez,et al.  Isolation of phenolic antioxidant compounds by SFC , 2005 .

[70]  M. Hamburger,et al.  Preparative purification of the major anti-inflammatory triterpenoid esters from Marigold (Calendula officinalis). , 2003, Fitoterapia.

[71]  A. Meireles,et al.  Global Yields, Chemical Compositions, and Antioxidant activities of extracts from Achyrocline alata and Achyrocline satureioides , 2006 .

[72]  G. Reglero,et al.  Kinetic study of pilot-scale supercritical CO2 extraction of rosemary (Rosmarinus officinalis) leaves , 2011 .

[73]  T. Lanaras,et al.  AUTUMN ESSENTIAL OILS OF GREEK OREGANO , 1997 .

[74]  D. A. Golden,et al.  Antimicrobial activity of essential oils from plants against selected pathogenic and saprophytic microorganisms. , 2001, Journal of food protection.

[75]  C. Peters,et al.  Application of double retrograde vaporization as an optimizing factor in supercritical fluid separations , 2005 .

[76]  F. Gironi,et al.  Continuous countercurrent deterpenation of lemon essential oil by means of supercritical carbon dioxide: Experimental data and process modelling , 2008 .

[77]  F. Anwar,et al.  Chemical composition, antioxidant and antimicrobial activities of basil (Ocimum basilicum) essential oils depends on seasonal variations. , 2008, Food chemistry.

[78]  B. Kayan,et al.  Terpene degradation and extraction from basil and oregano leaves using subcritical water. , 2007, Journal of chromatography. A.

[79]  E. Perry,et al.  Medicinal Plants and Alzheimer's Disease: from Ethnobotany to Phytotherapy ** , 1999, The Journal of pharmacy and pharmacology.

[80]  M. Meireles,et al.  Supercritical fluid extraction from rosemary (Rosmarinus officinalis): Kinetic data, extract's global yield, composition, and antioxidant activity , 2005 .

[81]  Raymond Mawson,et al.  APPLICATIONS AND OPPORTUNITIES FOR ULTRASOUND ASSISTED EXTRACTION IN THE FOOD INDUSTRY-A REVIEW , 2008 .

[82]  M. Melzig,et al.  Antispasmodic activity of essential oil from Lippia dulcis Trev. , 2008, Journal of Ethnopharmacology.

[83]  E. Ibáñez,et al.  Supercritical fluid extraction and fractionation of different preprocessed rosemary plants. , 1999, Journal of agricultural and food chemistry.

[84]  C. Doneanu,et al.  Isolation of Coriander Oil: Comparison Between Steam Distillation and Supercritical CO2 Extraction , 1997 .

[85]  M. Sanz,et al.  Solubility of some phenolic compounds contained in grape seeds, in supercritical carbon dioxide , 2002 .

[86]  K. Hua,et al.  Study on the antiinflammatory activity of essential oil from leaves of Cinnamomum osmophloeum. , 2005, Journal of agricultural and food chemistry.

[87]  T J Mason,et al.  Potential for the use of ultrasound in the extraction of antioxidants from Rosmarinus officinalis for the food and pharmaceutical industry. , 2004, Ultrasonics sonochemistry.

[88]  M. Angela A. Meireles,et al.  Supercritical Fluid Extraction of Bioactive Compounds: Fundamentals, Applications and Economic Perspectives , 2010 .

[89]  M. S. Díaz,et al.  Process optimization for supercritical concentration of orange peel oil , 2005 .

[90]  E. Reverchon,et al.  Extraction of sage oil by supercritical C02: Influence of some process parameters , 1995 .

[91]  B. Marongiu,et al.  Supercritical carbon dioxide extraction and characterization of Laurus nobilis essential oil. , 2002, Journal of agricultural and food chemistry.

[92]  Iolanda De Marco,et al.  Supercritical fluid extraction and fractionation of natural matter , 2006 .

[93]  M. Meireles,et al.  Supercritical fluid extraction of black pepper (Piper nigrun L.) essential oil , 1999 .

[94]  H. J. Dorman,et al.  Antimicrobial and antioxidant properties of some commercial essential oils , 1998 .

[95]  S. M. Pourmortazavi,et al.  Supercritical fluid extraction in plant essential and volatile oil analysis. , 2007, Journal of chromatography. A.

[96]  E. Stashenko,et al.  Comparison of different extraction methods for the analysis of volatile secondary metabolites of Lippia alba (Mill.) N.E. Brown, grown in Colombia, and evaluation of its in vitro antioxidant activity. , 2004, Journal of chromatography. A.

[97]  M. Meireles,et al.  Supercritical extraction of essential oil from aniseed (Pimpinella anisum L) using CO2: solubility, kinetics, and composition data. , 2003, Journal of agricultural and food chemistry.

[98]  E. Lesellier,et al.  Improved separation of furocoumarins of essential oils by supercritical fluid chromatography. , 2009, Journal of chromatography. A.

[99]  Ireneo Kikic,et al.  Flavour compounds of Lavandula angustifolia L. to use in food manufacturing: Comparison of three different extraction methods , 2009 .

[100]  E. Reverchon.  Fractional separation of SCF extracts from marjoram leaves: Mass transfer and optimization , 1992 .

[101]  Ana Belen Martin-Diana,et al.  Optimisation of Accelerated Solvent Extraction of Antioxidant Compounds from Rosemary (Rosmarinus officinalis L.), Marjoram (Origanum majorana L.) and Oregano (Origanum vulgare L.) Using Response Surface Methodology , 2011 .

[102]  K. Rezaei,et al.  Supercriticial fluid extraction of flavors and fragrances from Hyssopus officinalis L. cultivated in Iran , 2007 .