Green extraction of oil from Carum carvi seeds using bio-based solvent and supercritical fluid: evaluation of its antioxidant and anti-inflammatory activities
Carvi seeds; Green extraction; Oil; Supercritical fluid; MeTHF; Bioactivities
Abstract :
[en] Introduction: The consumption of health-promoting products such as oil seeds may improve
human health and prevent certain diseases. Carvi seeds have the potential to produce oil with
nutritional and functional properties rich on active compounds.
Objective: To extract bioactive lipids from Carum carvi seeds using green methodologies.
Material and methods: Supercritical CO2 and ethanol as co-solvent and bio-based solvent 2-
methyltetrahydrofuran (MeTHF) were used to extract the oil from Carum carvi. The yield, the
chemical composition, as well as antioxidant and anti-inflammatory activities of green
extracted oils were investigated and compared to those obtained with conventional methods
(hexane and Folch system).
Results: MeTHF extraction gave higher oil yield than that obtained by hexane. Fatty acids
composition of the two obtained green extracted oils was similar to conventional extracted
ones where petroselinic (39-43%), linoleic (29-31%) and oleic (19-21%) acids were the major
compounds. Besides, MeTHF and Sc-CO2 green extracted oils were enriched on bioactive
compounds including sterols (5.4 and 7.3 mg/g oil) and total polyphenols (9.3 and 7.6 mg
EAG/g oil) which were correlated to enhanced antiradical capacity. Moreover, the green
extracted oils exhibited high anti-inflammatory capacity inhibiting NO release in LPS-
induced RAW 264.7 macrophages with IC50 values of 28 and 24 μg/ml.
Conclusion: Green solvents are a good alternative to petroleum solvents to recover oil from
carvi seeds with high amount of nutritionally important fatty acids, along with significant
antioxidant and anti-inflammatory potential.
Daklaoui, Sarra; Biotechnology Center of Borj-Cedria
Msaada, Kamel; Biotechnology Center of Borj-Cedria
Saidani Tounsi, Moufida; Biotechnology Center of Borj-Cedria
Ksouri, Riadh; Biotechnology Center of Borj-Cedria
Fauconnier, Marie-Laure ; Université de Liège - ULiège > Agronomie, Bio-ingénierie et Chimie (AgroBioChem) > Chimie des agro-biosystèmes
Hamrouni-Sellemi, Ibtissem; Biotechnology Center of Borj-Cedria
Language :
English
Title :
Green extraction of oil from Carum carvi seeds using bio-based solvent and supercritical fluid: evaluation of its antioxidant and anti-inflammatory activities
Publication date :
2020
Journal title :
Phytochemical Analysis
ISSN :
0958-0344
eISSN :
1099-1565
Publisher :
John Wiley & Sons, Hoboken, United States - New Jersey
Kuna A, Achinna P. Mono unsaturated fatty acids for CVD and diabetes: a healthy choice. Int J Nutr Pharmacol Neurol Dis. 2013;3(3):236-248.
Moon DO, Kim MO, Choi YH, Kim GY. Beta-sitosterol induces G2/M arrest, endoreduplication, and apoptosis through the Bcl-2 and PI3k/Akt. Cancer Lett. 2008;264(2):181-191.
Lin TK, Zhong L, Santiago JL. Anti-inflammatory and skin barrier repair effects of topical application of some plant oils. Int J Mol Sci. 2018;19:70.
Ngo-Duy CC, Destaillats F, Keskitalo M, Arul J, Paul A. Triacylglycerols of Apiaceae seed oils: composition and regiodistribution of fatty acids. Eur J Lipid Sci Technol. 2009;111(2):164-169.
Shikov AN, Tsitsilin AN, Pozharitskaya ON, Makarov VG, Heinrich M. Traditional and current food use of wild plants listed in the Russian pharmacopoeia. Front Pharmacol. 2017;8:1-15.
Shikov AN, Pozharitskaya ON, Makarov VG, Wagner H, Verpoorte R, Heinrich M. Medicinal plants of the Russian pharmacopoeia; their history and applications. J Ethnopharmacol. 2014;154(3):481-536.
Keshavarz A, Minaiyan M, Ghannadi A, Mahzouni P. Effects of Carum carvi L. (caraway) extract and essential oil on TNBS-induced colitis in rats. Res Pharm Sci. 2013;8(1):1-8.
Johri RK. Cuminum cyminum and Carum carvi: an update. Pharmacogn Rev. 2011;5(9):63-72.
Delbeke EIP, Everaert J, Uitterhaegen E, et al. Petroselinic acid purification and its use for the fermentation of new sophorolipids. AMB Express. 2016;6(1):28.
Iverson SJ, Lang SLC, Cooper MH. Comparison of the Bligh and dyer and Folch methods for total lipid determination in a broad range of marine tissue. Lipids. 2001;36(11):1283-1287.
Fine F, Vian MA, Tixier ASF, Carre P, Pages X, Chemat F. Les agro-solvants pour l'extraction des huiles végétales issues de graines oléagineuses. OCL. 2013;20(5):A502.
De Simone JM. Practical approaches to green solvents. Science. 2002;297:799-802.
Kumar SPJ, Prasad SR, Banerjee R, Agarwal DK, Kulkarni KS, Ramesh KV. Green solvents and technologies for oil extraction from oil seeds. Chem Cent J. 2017;11-19.
Byrne FP, Jin S, Paggiola G, et al. Tools and techniques for solvent selection: green solvent selection guides. Sustain Chem Process. 2016;4-7.
Chemat F, Vian MA, Cravotto G. Green extraction of natural products: concept and principles. Int J Mol Sci. 2012;13(7):8615-8627.
Herrero M, Ibanez E. Green extraction processes, biorefineries and sustainability: recovery of high added-value products from natural sources. J Supercrit Fluid. 2018;134:252-259.
Hu A, Zhang Z, Zheng J, et al. Optimizations and comparison of two supercritical extractions of adlay oil. Innov Food Sci Emerg Technol. 2012;13:128-133.
Hurtado-Benavides A, Dorado AD, Del PilarSánchez-Camargo A. Study of the fatty acid profile and the aroma composition of oil obtained from roasted Colombian coffee beans by supercritical fluid extraction. J Supercr Fluid. 2016;113:44-52.
Soares JF, Pra VD, De Souza M, et al. Extraction of rice bran oil using supercritical CO2 and compressed liquefied petroleum gas. J Food Eng. 2016;170:58-63.
Kumar JSP, Kumar VG, Dash A, Scholz P, Banerjee R. Sustainable green solvents and techniques for lipid extraction from microalgae: a review. Algal Res. 2017;21:138-147.
Pace V, Hoyos P, Fernández M, Sinisterra JV, Alcántara AR. 2-Methyltetrahydrofuran as a suitable green solvent for phthalimide functionalization promoted by supported KF. Green Chem. 2010;12(8):1380-1382.
Gu Y, Jerome F. Bio-based solvents: an emerging generation of fluids for the design of eco-efficient processes in catalysis and organic chemistry. Chem Soc Rev. 2013;42(24):9550-9570.
Antonucci V, Coleman J, Ferry JB, et al. Toxicological assessment of 2-methyltetrahydrofuran and cyclopentyl methyl ether in support of their use in pharmaceutical chemical process development. Org Process Res Dev. 2011;15(4):939-941.
Pace V, Hoyos P, Castoldi L, De Maria PD, Alcntara AR. 2-Methyltetrahydrofuran (2-MeTHF): a biomass-derived solvent with broad application in organic chemistry. Chem Sus Chem. 2012;5(8):1369-1379.
Ben Youssef S, Fakhfakh J, Breil C, Abert-Vian M, Chemat F, Allouche N. Green extraction procedures of lipids from Tunisian date palm seeds. Ind Crop Prod. 2017;108:520-525.
Cascant MM, Breil C, Garrigues S, De la Guardia M, Fabiano Tixier AS, Chemat F. A green analytical chemistry approach for lipid extraction: computation methods in the selection of green solvents as alternative to hexane. Anal Bioanal Chem. 2017;409(14):3527-3539.
Chemat S, Lagh A, Amar HA, Bartels PV, Chemat F. Extraction of carvone and limonene from caraway seeds. Flav Frag J. 2004;19(3):188-195.
Assami K, Pingret D, Chemat S, Meklatia BY, Chemat F. Ultrasound induced intensification and selective extraction of essential oil from Carum carvi L. seeds. Chem Eng Proc. 2012;62:99-105.
Folch J, Lees M, Stanley GHS. A simple method for the isolation and purification of total lipids from animal tissues. J Biol Chem. 1957;226(1):497-509.
Koubaa M, Roselló-Soto E, ŠicŽlabur J, et al. Current and new insights in the sustainable and green recovery of nutritionally valuable compounds from Stevia rebaudiana Bertoni. J Agric Food Chem. 2015;63(31):6835-6846.
Cecchi G, Biasini S, Castano J. Méthanolyse rapide des huiles en solvant. Note de laboratoire. Rev Fr Corps Gras. 1985;4:163-164.
Parry J, Su L, Luther M, et al. Fatty acid composition and antioxidant properties of cold-pressed marionberry, boysenberry, red raspberry, and blueberry seed oils. J Agric Food Chem. 2005;53(3):566-573.
Green SJ, Meltzer MS, Hibbs JJB, Nacy CA. Activated macrophages destroy intracellular Leishmania major amastigotes by an l-arginine-dependent killing mechanism. J Immunol. 1990;144:278-283.
Krzyczkowska J, Kozłowska M. Effect of oils extracted from plant seeds on the growth and lipolytic activity of Yarrowia lipolytica yeast. J Am Oil Chem Soc. 2017;94(5):661-671.
Sicaire AG, Vian M, Fine F, et al. Alternative bio-based solvents for extraction of fat and oils: solubility prediction, global yield, extraction kinetics, chemical composition and cost of manufacturing. Int J Mol Sci. 2015;16(12):8430-8453.
Sicaire AG, Vian MA, Fine F, Carré P, Tostain S, Chemat F. Experimental approach versus COSMO-RS assisted solvent screening for predicting the solubility of rapeseed oil. OCL. 2015;22:1-7.
Breil C, Meullemiestre A, Vian M, Chemat F. Bio-based solvents for green extraction of lipids from oleaginous yeast biomass for sustainable aviation biofuel. Molecules. 2016;21(2):196.
Salgın U, Salgın S, Din D, Ekici DD, Uludag G. Oil recovery in rosehip seeds from food plant waste products using supercritical CO2 extraction. J Supercr Fluids. 2016;118:194-202.
Aladić K, Jarni K, Barbir T, et al. Supercritical CO2 extraction of hemp (Cannabis sativa L.) seed oil. Ind Crops Prod. 2015;76:472-478.
Kozłowska M, Gruczynska E, Scibisz I, Rudzinsk M. Fatty acids and sterols composition, and antioxidant activity of oils extracted from plant seeds. Food Chem. 2016;213:450-456.
Laribi B, Kouki K, Mougou A, Marzouk B. Fatty acid and essential oil composition of three Tunisian caraway (Carum carvi L.) seed ecotypes. J Sci Food Agric. 2010;90(3):391-396.
Aladic K, Jarni K, Barbir T, et al. Supercritical CO2 extraction of hemp (Cannabis sativa L.) seed oil. Ind Crops Prod. 2015;76:472-478.
Erkkila A, De Mello VDF, Riserus U, Laaksone DE. Dietary fatty acids and cardiovascular disease: an epidemiological approach. Prog Lipid Res. 2008;47(3):172-118.
Mhemdi H, Rodier E, Kechaou N, Fages J. A supercritical tuneable process for the selective extraction of fats and essential oil from coriander seeds. J Food Eng. 2011;105(4):609-616.
Dabrowski G, Konopka I, Czaplicki S. Supercritical CO2 extraction in chia oils production: impact of process duration and CO-solvent addition. Food Sci Biotechnol. 2018;27(3):677-686.
Prache N, Abreu S, Sassiat P, Thiebaut D, Chaminade P. Alternative solvents for improving the greenness of normal phase liquid chromatography of lipid classes. J Chromatogr a. 2016;1464:55-63.
Sajfrtová M, Licková I, Wimmerová M, Sovová H, Wimmer Z. β-Sitosterol: supercritical carbon dioxide extraction from sea buckthorn (Hippophae rhamnoides L.) seeds. Int J Mol Sci. 2010;11(4):1842-1850.
Mezni F, Slama A, Ksouri R, Hamdaoui G, Khouja ML, Khaldi A. Phenolic profile and effect of growing area on Pistacia lentiscus seed oil. Food Chem. 2018;257:206-210.
Ramadan MF. Healthy blends of high linoleic sunflower oil with selected cold pressed oils: functionality, stability and antioxidative characteristics. Ind Crop Prod. 2013;43:65-72.
Li H, Wu J, Rempel CB, Thiyam U. Effect of operating parameters on oil and phenolic extraction using supercritical CO2. Am Oil Chem Soc. 2010;87(9):1081-1089.
Temelli F. Perspective on supercritical processing of fats and oils. J Supercrit Fluids. 2009;47(3):583-590.
Piluzza G, Bullitta S. Correlations between phenolic content and antioxidant properties in twenty-four plant species of traditional ethnoveterinary use in the Mediterranean area. Pharm Biol. 2011;49(3):240-247.
Salkowski CA, Detore G, Menally R, Van Rooijem N, Vogel SN. Regulation of inducible nitric oxide synthase messenger RNA expression and nitric oxide production by lipopolysaccharide in vivo: the roles of macrophages, endogenous IFN-gamma and TNF receptor-1-mediated signalling. J Immunol. 1997;158:905-912.
Szabo C. Multiple pathways of peroxynitrite cytotoxicity. Toxicol Lett. 2003;140–141:105-112.
Cardeno A, Sanchez-Hidalgo M, Aparicio-Soto M, Sanchez-Fidalgo S, Alarcon-de-la-Lastra C. Extra virgin olive oil polyphenolic extracts downregulate inflammatory responses in LPS-activated murine peritoneal macrophages suppressing NF k B and MAPK signalling pathways. Food Funct. 2014;5(6):1270-1277.
Aparicio-soto M, Sanchez-Fidalgo S, Gonzalez-Benjumea A, Maya I, Fernandez-Bolanos JG, Alarcon-de-la-Lastra C. Naturally occurring hydroxytyrosol derivatives: hydroxytyrosyl acetate and 3,4-dihydroxyphenylglycol modulate inflammatory response in murine peritoneal macrophages. Potential utility as new dietary supplements. J Agric Food Chem. 2014;63:836-846.
Moreno JJ. Effect of olive oil minor components on oxidative stress and arachidonic acid mobilization and metabolism by macrophages RAW 264.7. Free Radic Biol Med. 2003;35(9):1073-1081.
Montserrat-de la Paz S, Fernández-Arche A, Angel-Martín M, García-Giménez MD. The sterols isolated from evening primrose oil modulate the release of proinflammatory mediators. Phytomedicine. 2012;19(12):1072-1076.
