New horizons in the extraction of bioactive compounds using deep eutectic solvents: A review

Analytica Chimica Acta

Volumn 979, Issue , 2017, Pages 1-23

  Zainal Abidin, Mohamad Hamdi ^a   Hayyan, Maan ^a   Hayyan, Adeeb ^a   Jayakumar, Natesan Subramanian ^a  

^a UNIVERSITY OF MALAYA   (Malaysia)

Author keywords

Anti cancer; Anti inflammatory; Anti oxidant; Green solvent; Ionic liquid; Separation technology

Indexed keywords

EUTECTICS; EXTRACTION; FLAVONOIDS; SOLVENTS;

ANTI-CANCER; ANTI-INFLAMMATORIES; BIOACTIVE COMPOUNDS; BIOCHEMICAL PROCESS; DEEP EUTECTIC SOLVENTS; EXTRACTION TECHNIQUES; GREEN SOLVENTS; SEPARATION TECHNOLOGIES;

IONIC LIQUIDS;

APIGENIN; ASTAXANTHIN; CARRAGEENAN; DEEP EUTECTIC SOLVENT; FLAVONOID; GENISTIN; ISOFLAVONE DERIVATIVE; KERATIN; PHENOL DERIVATIVE; SOLVENT; TANSHINONE; TERPENOID; TOCOL; UNCLASSIFIED DRUG; WATER; XANTHONE DERIVATIVE; HYDROXYBENZOIC ACID DERIVATIVE; PHENOLIC ACID; PLANT EXTRACT; TERPENE;

AQUEOUS TWO PHASE PARTITION EXTRACTION; BALL MILL ASSISTED EXTRACTION; DRUG STRUCTURE; EXTRACTION; HEATING STIRRING EXTRACTION; MICROWAVE ASSISTED EXTRACTION; NEGATIVE PRESSURE CAVITATION EXTRACTION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; REVIEW; ULTRASONIC ASSISTED EXTRACTION; ULTRASONIC IRRADIATION ASSISTED EXTRACTION;

CARRAGEENAN; FLAVONOIDS; HYDROXYBENZOATES; PLANT EXTRACTS; SOLVENTS; TERPENES;

EID: 85019725544     PISSN: 00032670     EISSN: 18734324     Source Type: Journal    
DOI: 10.1016/j.aca.2017.05.012     Document Type: Review

References (192)

1. Mbous, Y.P., Hayyan, M., Hayyan, A., Wong, W.F., Hashim, M.A., Looi, C.Y., Applications of deep eutectic solvents in biotechnology and bioengineering—promises and challenges. Biotechnol. Adv. 35 (2017), 105–134.
2. Agostini-Costa, T.d.S., Vieira, R.F., Bizzo, H.R., Silveira, D., Gimenes, M.A., Secondary Metabolites. 2012, InTech, Rijeka, Croatia.
3. Oksman-Caldentey, K.-M., Inzé, D., Plant cell factories in the post-genomic era: new ways to produce designer secondary metabolites. Trends Plant Sci. 9 (2004), 433–440.
4. Ventura, S.P.M., e Silva, F.A., Quental, M.V., Mondal, D., Freire, M.G., Coutinho, J.A.P., Ionic-liquid-mediated extraction and separation processes for bioactive compounds: past, present, and future trends. Chem. Rev., 2017, 10.1021/acs.chemrev.1026b00550.
5. Bart, H.J., Extraction of Natural Products from Plants-an Introduction. 2011, Wiley-VCH Verlag GmbH & Co, KGaA, Kaiserslautern, Germany.
6. Wang, L., Weller, C.L., Recent advances in extraction of nutraceuticals from plants. Trends Food Sci. Technol. 17 (2006), 300–312.
7. Wang, M., Wang, J., Zhang, Y., Xia, Q., Bi, W., Yang, X., Chen, D.D.Y., Fast environment-friendly ball mill-assisted deep eutectic solvent-based extraction of natural products. J. Chromatogr. A 1443 (2016), 262–266.
8. Tang, B., Zhang, H., Row, K.H., Application of deep eutectic solvents in the extraction and separation of target compounds from various samples. J. Sep. Sci. 38 (2015), 1053–1064.
9. Smith, E.L., Abbott, A.P., Ryder, K.S., Deep eutectic solvents (DESs) and their applications. Chem. Rev. 114 (2014), 11060–11082.
10. Jin, W., Yang, Q., Huang, B., Bao, Z., Su, B., Ren, Q., Yang, Y., Xing, H., Enhanced solubilization and extraction of hydrophobic bioactive compounds using water/ionic liquid mixtures. Green Chem. 18 (2016), 3549–3557.
11. Egorova, K.S., Gordeev, E.G., Ananikov, V.P., Biological activity of ionic liquids and their application in pharmaceutics and medicine. Chem. Rev., 2017, 10.1021/acs.chemrev.1026b00562.
12. Hayyan, M., Mbous, Y.P., Looi, C.Y., Wong, W.F., Hayyan, A., Salleh, Z., Mohd-Ali, O., Natural deep eutectic solvents: cytotoxic profile. Springer Plus, 5, 2016, 913.
13. Passos, H., Freire, M.G., Coutinho, J.A.P., Ionic liquid solutions as extractive solvents for value-added compounds from biomass. Green Chem. 16 (2014), 4786–4815.
14. Gorke, J., Srienc, F., Kazlauskas, R., Toward advanced ionic liquids. Polar, enzyme-friendly solvents for biocatalysis. Biotechnol. Bioprocess Eng. 15 (2010), 40–53.
15. Hayyan, M., Looi, C.Y., Hayyan, A., Wong, W.F., Hashim, M.A., In vitro and in vivo toxicity profiling of ammonium-based deep eutectic solvents. PLoS One, 10, 2015, e0117934.
16. Juneidi, I., Hayyan, M., Mohd Ali, O., Toxicity profile of choline chloride-based deep eutectic solvents for fungi and Cyprinus carpio fish. Environ. Sci. Pollut. Res. 23 (2016), 7648–7659.
17. Juneidi, I., Hayyan, M., Hashim, M.A., Evaluation of toxicity and biodegradability for cholinium-based deep eutectic solvents. RSC Adv. 5 (2015), 83636–83647.
18. Kareem, M.A., Mjalli, F.S., Hashim, M.A., AlNashef, I.M., Phosphonium-based ionic liquids analogues and their physical properties. J. Chem. Eng. Data 55 (2010), 4632–4637.
19. van Osch, D.J.G.P., Zubeir, L.F., van den Bruinhorst, A., Rocha, M.A.A., Kroon, M.C., Hydrophobic deep eutectic solvents as water-immiscible extractants. Green Chem. 17 (2015), 4518–4521.
20. Radošević, K., Bubalo, M.C., Srček, V.G., Grgas, D., Dragičević, T.L., Redovniković, I.R., Evaluation of toxicity and biodegradability of choline chloride based deep eutectic solvents. Ecotoxicol. Environ. Saf. 112 (2015), 46–53.
21. Abbott, A.P., Boothby, D., Capper, G., Davies, D.L., Rasheed, R.K., Deep eutectic solvents formed between choline chloride and carboxylic acids: versatile alternatives to ionic liquids. J. Am. Chem. Soc. 126 (2004), 9142–9147.
22. Carriazo, D., Serrano, M.C., Gutierrez, M.C., Ferrer, M.L., del Monte, F., Deep-eutectic solvents playing multiple roles in the synthesis of polymers and related materials. Chem. Soc. Rev. 41 (2012), 4996–5014.
23. Zhang, Q., De Oliveira Vigier, K., Royer, S., Jerome, F., Deep eutectic solvents: syntheses, properties and applications. Chem. Soc. Rev. 41 (2012), 7108–7146.
24. Choi, Y.H., van Spronsen, J., Dai, Y., Verberne, M., Hollmann, F., Arends, I.W.C.E., Witkamp, G.-J., Verpoorte, R., Are natural deep eutectic solvents the missing link in understanding cellular metabolism and physiology?. Plant Physiol. 156 (2011), 1701–1705.
25. Dai, Y., Rozema, E., Verpoorte, R., Choi, Y.H., Application of natural deep eutectic solvents to the extraction of anthocyanins from Catharanthus roseus with high extractability and stability replacing conventional organic solvents. J. Chromatog. A 1434 (2016), 50–56.
26. Dai, Y., van Spronsen, J., Witkamp, G.-J., Verpoorte, R., Choi, Y.H., Natural deep eutectic solvents as new potential media for green technology. Anal. Chim. Acta. 766 (2013), 61–68.
27. Nkuku, C.A., LeSuer, R.J., Electrochemistry in deep eutectic solvents. J. Phys. Chem. B 111 (2007), 13271–13277.
28. Jhong, H.-R., Wong, D.S.-H., Wan, C.-C., Wang, Y.-Y., Wei, T.-C., A novel deep eutectic solvent-based ionic liquid used as electrolyte for dye-sensitized solar cells. Electrochem. Commun. 11 (2009), 209–211.
29. Mbous, Y.P., Hayyan, M., Wong, W.F., Looi, C.Y., Hashim, M.A., Unraveling the cytotoxicity and metabolic pathways of binary natural deep eutectic solvent systems. Sci. Rep., 7, 2017, 41257, 10.1038/srep41257.
30. Duan, L., Dou, L.-L., Guo, L., Li, P., Liu, E.H., Comprehensive evaluation of deep eutectic solvents in extraction of bioactive natural products. ACS Sustain. Chem. Eng. 4 (2016), 2405–2411.
31. Bi, W., Tian, M., Row, K.H., Evaluation of alcohol-based deep eutectic solvent in extraction and determination of flavonoids with response surface methodology optimization. J. Chromatogr. A 1285 (2013), 22–30.
32. Duan, L., Guo, L., Liu, K., Liu, E.H., Li, P., Characterization and classification of seven citrus herbs by liquid chromatography-quadrupole time-of-flight mass spectrometry and genetic algorithm optimized support vector machines. J. Chromatogr. A 1339 (2014), 118–127.
33. Guo, W., Hou, Y., Wu, W., Ren, S., Tian, S., Marsh, K.N., Separation of phenol from model oils with quaternary ammonium salts via forming deep eutectic solvents. Green Chem. 15 (2013), 226–229.
34. Mukhopadhyay, S., Mukherjee, S., Adnan, N.F., Hayyan, A., Hayyan, M., Hashim, M.A., Sen Gupta, B., Ammonium-based deep eutectic solvents as novel soil washing agent for lead removal. Chem. Eng. J. 294 (2016), 316–322.
35. Mukhopadhyay, S., Mukherjee, S., Hayyan, A., Hayyan, M., Hashim, M.A., Sen Gupta, B., Enhanced removal of lead from contaminated soil by polyol-based deep eutectic solvents and saponin. J. Contam. Hydrol. 194 (2016), 17–23.
36. Hizaddin, H.F., Sarwono, M., Hashim, M.A., Alnashef, I.M., Hadj-Kali, M.K., Coupling the capabilities of different complexing agents into deep eutectic solvents to enhance the separation of aromatics from aliphatics. J. Chem. Thermodyn. 84 (2015), 67–75.
37. Jawale, D.V., Pratap, U.R., Mane, R.A., An alternative synthetic route for an antidiabetic drug, rosiglitazone. Bioorg. Med. Chem. Lett. 22 (2012), 924–928.
38. Qi, X.-L., Peng, X., Huang, Y.-Y., Li, L., Wei, Z.-F., Zu, Y.-G., Fu, Y.-J., Green and efficient extraction of bioactive flavonoids from Equisetum palustre L. by deep eutectic solvents-based negative pressure cavitation method combined with macroporous resin enrichment. Ind. Crops Prod. 70 (2015), 142–148.
39. Wei, Z.-F., Wang, X.-Q., Peng, X., Wang, W., Zhao, C.-J., Zu, Y.-G., Fu, Y.-J., Fast and green extraction and separation of main bioactive flavonoids from Radix Scutellariae. Ind. Crops Prod. 63 (2015), 175–181.
40. Bakirtzi, C., Triantafyllidou, K., Makris, D.P., Novel lactic acid-based natural deep eutectic solvents: efficiency in the ultrasound-assisted extraction of antioxidant polyphenols from common native Greek medicinal plants. J. Appl. Res. Med. Aromat. Plants 3 (2016), 120–127.
41. García, A., Rodríguez-Juan, E., Rodríguez-Gutiérrez, G., Rios, J.J., Fernández-Bolaños, J., Extraction of phenolic compounds from virgin olive oil by deep eutectic solvents (DESs). Food Chem. 197:Part A (2016), 554–561.
42. Peng, X., Duan, M.-H., Yao, X.-H., Zhang, Y.-H., Zhao, C.-J., Zu, Y.-G., Fu, Y.-J., Green extraction of five target phenolic acids from Lonicerae japonicae Flos with deep eutectic solvent. Sep. Purif. Technol. 157 (2016), 249–257.
43. Dai, Y., Witkamp, G.-J., Verpoorte, R., Choi, Y.H., Natural deep eutectic solvents as a new extraction media for phenolic metabolites in Carthamus tinctorius L. Anal. Chem. 85 (2013), 6272–6278.
44. Wei, Z., Qi, X., Li, T., Luo, M., Wang, W., Zu, Y., Fu, Y., Application of natural deep eutectic solvents for extraction and determination of phenolics in Cajanus cajan leaves by ultra performance liquid chromatography. Sep. Purif. Technol. 149 (2015), 237–244.
45. Nam, M.W., Zhao, J., Lee, M.S., Jeong, J.H., Lee, J., Enhanced extraction of bioactive natural products using tailor-made deep eutectic solvents: application to flavonoid extraction from Flos sophorae. Green Chem. 17 (2015), 1718–1727.
46. Abbott, A.P., Capper, G., Davies, D.L., Munro, H.L., Rasheed, R.K., Tambyrajah, V., Preparation of novel, moisture-stable, Lewis-acidic ionic liquids containing quaternary ammonium salts with functional side chains. Chem. Commun., 2001, 2010–2011.
47. Abbott, A.P., Capper, G., Davies, D.L., Rasheed, R.K., Tambyrajah, V., Novel solvent properties of choline chloride/urea mixtures. Chem. Commun., 2003, 70–71.
48. Wasserscheid, P., Welton, T., Ionic Liquids in Synthesis. 2008, Wiley Online Library.
49. Abbott, A.P., Capper, G., Gray, S., Design of improved deep eutectic solvents using hole theory. Chem. Phys. Chem 7 (2006), 803–806.
50. Abbott, A.P., Harris, R.C., Ryder, K.S., D'Agostino, C., Gladden, L.F., Mantle, M.D., Glycerol eutectics as sustainable solvent systems. Green Chem. 13 (2011), 82–90.
51. Shahbaz, K., Mjalli, F., Hashim, M., AlNashef, I., Prediction of deep eutectic solvents densities at different temperatures. Thermochim. Acta 515 (2011), 67–72.
52. Dai, Y., Witkamp, G.-J., Verpoorte, R., Choi, Y.H., Tailoring properties of natural deep eutectic solvents with water to facilitate their applications. Food Chem. 187 (2015), 14–19.
53. Abbott, A.P., Harris, R.C., Ryder, K.S., Application of hole theory to define ionic liquids by their transport properties. J. Phys. Chem. B 111 (2007), 4910–4913.
54. D'Agostino, C., Harris, R.C., Abbott, A.P., Gladden, L.F., Mantle, M.D., Molecular motion and ion diffusion in choline chloride based deep eutectic solvents studied by 1H pulsed field gradient NMR spectroscopy. Phys. Chem. Chem. Phys. 13 (2011), 21383–21391.
55. Abbott, A.P., Barron, J.C., Ryder, K.S., Wilson, D., Eutectic-based ionic liquids with metal-containing anions and cations. Chem. Eur. J. 13 (2007), 6495–6501.
56. Shahbaz, K., Baroutian, S., Mjalli, F.S., Hashim, M.A., AlNashef, I.M., Densities of ammonium and phosphonium based deep eutectic solvents: prediction using artificial intelligence and group contribution techniques. Thermochim. Acta 527 (2012), 59–66.
57. Pandey, A., Rai, R., Pal, M., Pandey, S., How polar are choline chloride-based deep eutectic solvents?. Phys. Chem. Chem. Phys. 16 (2014), 1559–1568.
58. Pandey, A., Pandey, S., Solvatochromic probe behavior within choline chloride-based deep eutectic solvents: effect of temperature and water. J. Phys. Chem. B 118 (2014), 14652–14661.
59. Leron, R.B., Li, M.-H., Solubility of carbon dioxide in a choline chloride–ethylene glycol based deep eutectic solvent. Thermochim. Acta 551 (2013), 14–19.
60. Li, Z., Investigation of Deep Eutectic Solvents and Their Derivatives for Pharmaceutical Applications. Master Thesis, 2015, University of Toronto.
61. Aroso, I.M., Silva, J.C., Mano, F., Ferreira, A.S., Dionísio, M., Sá-Nogueira, I., Barreiros, S., Reis, R.L., Paiva, A., Duarte, A.R.C., Dissolution enhancement of active pharmaceutical ingredients by therapeutic deep eutectic systems. Eur. J. Pharm. Biopharm. 98 (2016), 57–66.
62. Mamajanov, I., Engelhart, A.E., Bean, H.D., Hud, N.V., DNA and RNA in anhydrous media: duplex, triplex, and G-quadruplex secondary structures in a deep eutectic solvent. Angew. Chem. Int. Ed. 49 (2010), 6310–6314.
63. Lannan, F.M., Mamajanov, I., Hud, N.V., Human telomere sequence DNA in water-free and high-viscosity solvents: G-quadruplex folding governed by Kramers rate theory. J. Am. Chem. Soc. 134 (2012), 15324–15330.
64. Mondal, D., Sharma, M., Mukesh, C., Gupta, V., Prasad, K., Improved solubility of DNA in recyclable and reusable bio-based deep eutectic solvents with long-term structural and chemical stability. Chem. Commun. 49 (2013), 9606–9608.
65. Morrison, H.G., Sun, C.C., Neervannan, S., Characterization of thermal behavior of deep eutectic solvents and their potential as drug solubilization vehicles. Int. J. Pharm. 378 (2009), 136–139.
66. Paiva, A., Craveiro, R., Aroso, I., Martins, M., Reis, R.L., Duarte, A.R.C., Natural deep eutectic solvents—solvents for the 21st century. ACS Sustain. Chem. Eng. 2 (2014), 1063–1071.
67. Lee, Y.R., Row, K.H., Comparison of ionic liquids and deep eutectic solvents as additives for the ultrasonic extraction of astaxanthin from marine plants. J. Ind. Eng. Chem. 39 (2016), 87–92.
68. Liu, F., Wang, D., Liu, W., Wang, X., Bai, A., Huang, L., Ionic liquid-based ultrahigh pressure extraction of five tanshinones from Salvia miltiorrhiza Bunge. Sep. Purif. Technol. 110 (2013), 86–92.
69. Wu, H., Yao, S., Qian, G., Yao, T., Song, H., A resolution approach of racemic phenylalanine with aqueous two-phase systems of chiral tropine ionic liquids. J. Chromatogr. A 1418 (2015), 150–157.
70. Higuera-Ciapara, I., Félix-Valenzuela, L., Goycoolea, F.M., Astaxanthin: a review of its chemistry and applications. Crit. Rev. Food Sci. Nutr. 46 (2006), 185–196.
71. Shu, Y., Cheng, D., Chen, X., Wang, J., A reverse microemulsion of water/AOT/1-butyl-3-methylimidazolium hexafluorophosphate for selective extraction of hemoglobin. Sep. Purif. Technol. 64 (2008), 154–159.
72. Mao, Q.-X., Wang, H., Shu, Y., Chen, X.-W., Wang, J.-H., A dual-ionic liquid microemulsion system for the selective isolation of hemoglobin. RSC Adv. 4 (2014), 8177–8182.
73. Vicente, F.A., Malpiedi, L.P., e Silva, F.A., Pessoa Jr, A., Coutinho, J.A.P., Ventura, S.P.M., Design of novel aqueous micellar two-phase systems using ionic liquids as co-surfactants for the selective extraction of (bio)molecules. Sep. Purif. Technol. 135 (2014), 259–267.
74. Viçosa, A., Letourneau, J.-J., Espitalier, F., Inês Ré, M., An innovative antisolvent precipitation process as a promising technique to prepare ultrafine rifampicin particles. J. Cryst. Growth 342 (2012), 80–87.
75. Kroon, M.C., Toussaint, V.A., Shariati, A., Florusse, L.J., van Spronsen, J., Witkamp, G.-J., Peters, C.J., Crystallization of an organic compound from an ionic liquid using carbon dioxide as anti-solvent. Green Chem. 10 (2008), 333–336.
76. Smith, K.B., Bridson, R.H., Leeke, G.A., Crystallisation control of paracetamol from ionic liquids. Cryst. Eng. Comm 16 (2014), 10797–10803.
77. Cui, Q., Peng, X., Yao, X.-H., Wei, Z.-F., Luo, M., Wang, W., Zhao, C.-J., Fu, Y.-J., Zu, Y.-G., Deep eutectic solvent-based microwave-assisted extraction of genistin, genistein and apigenin from pigeon pea roots. Sep. Purif. Technol. 150 (2015), 63–72.
78. Yao, X.-H., Zhang, D.-Y., Duan, M.-H., Cui, Q., Xu, W.-J., Luo, M., Li, C.-Y., Zu, Y.-G., Fu, Y.-J., Preparation and determination of phenolic compounds from Pyrola incarnata Fisch. with a green polyols based-deep eutectic solvent. Sep. Purif. Technol. 149 (2015), 116–123.
79. Liu, Y., Yang, L., Zu, Y., Zhao, C., Zhang, L., Zhang, Y., Zhang, Z., Wang, W., Development of an ionic liquid-based microwave-assisted method for simultaneous extraction and distillation for determination of proanthocyanidins and essential oil in Cortex cinnamomi. Food Chem. 135 (2012), 2514–2521.
80. Jiao, J., Gai, Q.-Y., Fu, Y.-J., Zu, Y.-G., Luo, M., Zhao, C.-J., Li, C.-Y., Microwave-assisted ionic liquids treatment followed by hydro-distillation for the efficient isolation of essential oil from Fructus forsythiae seed. Sep. Purif. Technol. 107 (2013), 228–237.
81. Bonny, S., Paquin, L., Carrié, D., Boustie, J., Tomasi, S., Ionic liquids based microwave-assisted extraction of lichen compounds with quantitative spectrophotodensitometry analysis. Anal. Chim. Acta 707 (2011), 69–75.
82. Xia, B., Yan, D., Bai, Y., Xie, J., Cao, Y., Liao, D., Lin, L., Determination of phenolic acids in Prunella vulgaris L.: a safe and green extraction method using alcohol-based deep eutectic solvents. Anal. Methods 7 (2015), 9354–9364.
83. Wang, W., Li, Q., Liu, Y., Chen, B., Ionic liquid-aqueous solution ultrasonic-assisted extraction of three kinds of alkaloids from Phellodendron amurense Rupr and optimize conditions use response surface. Ultrason. Sonochem. 24 (2015), 13–18.
84. Ma, C.-h., Liu, T.-t., Yang, L., Zu, Y.-g., Wang, S.-y., Zhang, R.-r., Study on ionic liquid-based ultrasonic-assisted extraction of biphenyl cyclooctene lignans from the fruit of Schisandra chinensis Baill. Anal. Chim. Acta 689 (2011), 110–116.
85. Cao, X., Ye, X., Lu, Y., Yu, Y., Mo, W., Ionic liquid-based ultrasonic-assisted extraction of piperine from white pepper. Anal. Chim. Acta 640 (2009), 47–51.
86. Tan, T., Lai, C.-J.-S., OuYang, H., He, M.-Z., Feng, Y., Ionic liquid-based ultrasound-assisted extraction and aqueous two-phase system for analysis of caffeoylquinic acids from Flos Lonicerae Japonicae. J. Pharm. Biomed. Anal. 120 (2016), 134–141.
87. Li, N., Wang, Y., Xu, K., Huang, Y., Wen, Q., Ding, X., Development of green betaine-based deep eutectic solvent aqueous two-phase system for the extraction of protein. Talanta 152 (2016), 23–32.
88. Santos, P.L., Santos, L.N.S., Ventura, S.P.M., de Souza, R.L., Coutinho, J.A.P., Soares, C.M.F., Lima, Á.S., Recovery of capsaicin from Capsicum frutescens by applying aqueous two-phase systems based on acetonitrile and cholinium-based ionic liquids. Chem. Eng. Res. Des. 112 (2016), 103–112.
89. Freire, M.G., Neves, C.M.S.S., Marrucho, I.M., Canongia Lopes, J.N., Rebelo, L.P.N., Coutinho, J.A.P., High-performance extraction of alkaloids using aqueous two-phase systems with ionic liquids. Green Chem. 12 (2010), 1715–1718.
90. Duan, M.-H., Luo, M., Zhao, C.-J., Wang, W., Zu, Y.-G., Zhang, D.-Y., Yao, X.-h., Fu, Y.-J., Ionic liquid-based negative pressure cavitation-assisted extraction of three main flavonoids from the pigeonpea roots and its pilot-scale application. Sep. Purif. Technol. 107 (2013), 26–36.
91. Dong, L.-L., Fu, Y.-J., Zu, Y.-G., Li, J., Li, X.-J., Efferth, T., Negative pressure cavitation accelerated processing for extraction of main bioactive flavonoids from Radix Scutellariae. Chem. Eng. Process. Process Intensif. 50 (2011), 780–789.
92. Moore, K.E., Mangos, D.N., Slattery, A.D., Raston, C.L., Boulos, R.A., Wool deconstruction using a benign eutectic melt. RSC Adv. 6 (2016), 20095–20101.
93. Yang, L., Liu, Y., Zu, Y.-g., Zhao, C.-j., Zhang, L., Chen, X.-q., Zhang, Z.-h., Optimize the process of ionic liquid-based ultrasonic-assisted extraction of aesculin and aesculetin from Cortex fraxini by response surface methodology. Chem. Eng. J. 175 (2011), 539–547.
94. Yang, L., Sun, X., Yang, F., Zhao, C., Zhang, L., Zu, Y., Application of ionic liquids in the microwave-assisted extraction of Proanthocyanidins from Larix gmelini bark. Int. J. Mol. Sci. 13 (2012), 5163–5178.
95. Mulia, K., Krisanti, E., Terahadi, F., Putri, S., Selected natural deep eutectic solvents for the extraction of α-mangostin from mangosteen (Garcinia mangostana l.) pericarp. Int. J. Tech. 7 (2015), 1211–1220.
96. Zhao, B.-Y., Xu, P., Yang, F.-X., Wu, H., Zong, M.-H., Lou, W.-Y., Biocompatible deep eutectic solvents based on choline chloride: characterization and application to the extraction of rutin from Sophora japonica. ACS Sustain. Chem. Eng. 3 (2015), 2746–2755.
97. Xu, K., Wang, Y., Huang, Y., Li, N., Wen, Q., A green deep eutectic solvent-based aqueous two-phase system for protein extracting. Anal. Chim. Acta 864 (2015), 9–20.
98. Abdul Hadi, N.m., Ng, M.H., Choo, Y.M., Hashim, M.A., Jayakumar, N.S., Performance of choline-based deep eutectic solvents in the extraction of tocols from crude palm oil. J. Am. Oil Chem. Soc. 92 (2015), 1709–1716.
99. Paradiso, V.M., Clemente, A., Summo, C., Pasqualone, A., Caponio, F., Towards green analysis of virgin olive oil phenolic compounds: extraction by a natural deep eutectic solvent and direct spectrophotometric detection. Food Chem. 212 (2016), 43–47.
100. Vermerris, W., Nicholson, R., Phenolic Compound Biochemistry. 2007, Springer Science & Business Media, New York.
101. Keleş, A., Koca, I., Gençcelep, H., Antioxidant properties of wild edible mushrooms. J. Food Process Technol. 2 (2011), 130–136.
102. Abidin, M.H., Abdullah, N., Abidin, N.Z., Protective effect of antioxidant extracts from grey oyster mushroom, Pleurotus pulmonarius (Agaricomycetes), against human low-density lipoprotein oxidation and aortic endothelial cell damage. Int. J. Med. Mushrooms 18 (2016), 109–121.
103. Mayakrishnan, V., Abdullah, N., Abidin, M.H.Z., Fadzil, N.H.M., Johari, N.M.K., Aminudin, N., Abidin, N.Z., Investigation of the antioxidative potential of various solvent fractions from fruiting bodies of Schizophyllum commune (Fr.) mushrooms and characterization of phytoconstituents. J. Agric. Sci. 5 (2013), 58–69.
104. Owen, R.W., Giacosa, A., Hull, W.E., Haubner, R., Spiegelhalder, B., Bartsch, H., The antioxidant/anticancer potential of phenolic compounds isolated from olive oil. Eur. J. Cancer 36 (2000), 1235–1247.
105. Phan, C.W., David, P., Naidu, M., Wong, K.H., Sabaratnam, V., Therapeutic potential of culinary-medicinal mushrooms for the management of neurodegenerative diseases: diversity, metabolite, and mechanism. Crit. Rev. Biotechnol. 35 (2015), 355–368.
106. Rahman, M.A., Abdullah, N., Aminudin, N., Interpretation of mushroom as a common therapeutic agent for Alzheimer's disease and cardiovascular diseases. Crit. Rev. Biotechnol. 36 (2016), 1131–1142.
107. Palacios, I., Lozano, M., Moro, C., D'Arrigo, M., Rostagno, M.A., Martínez, J.A., García-Lafuente, A., Guillamón, E., Villares, A., Antioxidant properties of phenolic compounds occurring in edible mushrooms. Food Chem. 128 (2011), 674–678.
108. Abdullah, N., Ismail, S.M., Aminudin, N., Shuib, A.S., Lau, B.F., Evaluation of selected culinary-medicinal mushrooms for antioxidant and ACE inhibitory activities. Evid. Based Complement. Altern. Med., 2012, 1–12.
109. Ghasemzadeh, A., Jaafar, H.Z., Profiling of phenolic compounds and their antioxidant and anticancer activities in pandan (Pandanus amaryllifolius Roxb.) extracts from different locations of Malaysia, BMC Complement. Altern. Med., 13, 2013, 341.
110. Cuong, T.D., Hung, T.M., Lee, J.S., Weon, K.Y., Woo, M.H., Min, B.S., Anti-inflammatory activity of phenolic compounds from the whole plant of Scutellaria indica. Bioorg. Med. Chem. Lett. 25 (2015), 1129–1134.
111. Hayes, J.E., Allen, P., Brunton, N., O'Grady, M.N., Kerry, J.P., Phenolic composition and in vitro antioxidant capacity of four commercial phytochemical products: olive leaf extract (Olea europaea L.), lutein, sesamol and ellagic acid. Food Chem. 126 (2011), 948–955.
112. Orhan, I., Üstün, O., Determination of total phenol content, antioxidant activity and acetylcholinesterase inhibition in selected mushrooms from Turkey. J. Food Compost. Anal. 24 (2011), 386–390.
113. Khezeli, T., Daneshfar, A., Sahraei, R., A green ultrasonic-assisted liquid–liquid microextraction based on deep eutectic solvent for the HPLC-UV determination of ferulic, caffeic and cinnamic acid from olive, almond, sesame and cinnamon oil. Talanta 150 (2016), 577–585.
114. Akao, Y., Nakagawa, Y., Iinuma, M., Nozawa, Y., Anti-cancer effects of xanthones from pericarps of mangosteen. Int. J. Mol. Sci. 9 (2008), 355–370.
115. Kondo, M., Zhang, L., Ji, H., Kou, Y., Ou, B., Bioavailability and antioxidant effects of a xanthone-rich Mangosteen (Garcinia mangostana) product in humans. J. Agric. Food. Chem. 57 (2009), 8788–8792.
116. Weecharangsan, W., Opanasopit, P., Sukma, M., Ngawhirunpat, T., Sotanaphun, U., Siripong, P., Antioxidative and neuroprotective activities of extracts from the fruit hull of mangosteen (Garcinia mangostana Linn.). Med. Princ. Pract. 15 (2006), 281–287.
117. Aisha, A.F.A., Abu-Salah, K.M., Ismail, Z., Majid, A.M.S.A., In vitro and in vivo anti-colon cancer effects of Garcinia mangostana xanthones extract. BMC Complement. Altern. Med. 12 (2012), 1–10.
118. Pedraza-Chaverri, J., Cardenas-Rodriguez, N., Orozco-Ibarra, M., Perez-Rojas, J.M., Medicinal properties of mangosteen (Garcinia mangostana). Food Chem. Toxicol. 46 (2008), 3227–3239.
119. Obolskiy, D., Pischel, I., Siriwatanametanon, N., Heinrich, M., Garcinia mangostana L.: a phytochemical and pharmacological review. Phytother. Res. 23 (2009), 1047–1065.
120. Yu, L., Zhao, M., Yang, B., Zhao, Q., Jiang, Y., Phenolics from hull of Garcinia mangostana fruit and their antioxidant activities. Food Chem. 104 (2007), 176–181.
121. Walker, E.B., HPLC analysis of selected xanthones in mangosteen fruit. J. Sep. Sci. 30 (2007), 1229–1234.
122. Cao, J., Yang, M., Cao, F., Wang, J., Su, E., Well-designed hydrophobic deep eutectic solvents as green and efficient media for the extraction of artemisinin from Artemisia annua leaves. ACS Sustain. Chem. Eng., 2017, 10.1021/acssuschemeng.1026b03092.
123. García-Lafuente, A., Guillamón, E., Villares, A., Rostagno, M.A., Martínez, J.A., Flavonoids as anti-inflammatory agents: implications in cancer and cardiovascular disease. Inflamm. Res. 58 (2009), 537–552.
124. Ravishankar, D., Rajora, A.K., Greco, F., Osborn, H.M., Flavonoids as prospective compounds for anti-cancer therapy. Int. J. Biochem. Cell Biol. 45 (2013), 2821–2831.
125. Chowdhury, A.R., Sharma, S., Mandal, S., Goswami, A., Mukhopadhyay, S., Majumder, H.K., Luteolin, an emerging anti-cancer flavonoid, poisons eukaryotic DNA topoisomerase I. Biochem. J. 366 (2002), 653–661.
126. Nagaprashantha, L.D., Vatsyayan, R., Singhal, J., Fast, S., Roby, R., Awasthi, S., Singhal, S.S., Anti-cancer effects of novel flavonoid vicenin-2 as a single agent and in synergistic combination with docetaxel in prostate cancer. Biochem. Pharmacol. 82 (2011), 1100–1109.
127. Meda, A., Lamien, C.E., Romito, M., Millogo, J., Nacoulma, O.G., Determination of the total phenolic, flavonoid and proline contents in Burkina Fasan honey, as well as their radical scavenging activity. Food Chem. 91 (2005), 571–577.
128. Zeng, H., Wang, Y., Kong, J., Nie, C., Yuan, Y., Ionic liquid-based microwave-assisted extraction of rutin from Chinese medicinal plants. Talanta 83 (2010), 582–590.
129. Gu, H., Chen, F., Zhang, Q., Zang, J., Application of ionic liquids in vacuum microwave-assisted extraction followed by macroporous resin isolation of three flavonoids rutin, hyperoside and hesperidin from Sorbus tianschanica leaves. J. Chromatogr. B 1014 (2016), 45–55.
130. Xu, W., Chu, K., Li, H., Zhang, Y., Zheng, H., Chen, R., Chen, L., Ionic liquid-based microwave-assisted extraction of flavonoids from Bauhinia championii (Benth.) Benth. Molecules 17 (2012), 14323–14335.
131. Ko, M.-J., Cheigh, C.-I., Cho, S.-W., Chung, M.-S., Subcritical water extraction of flavonol quercetin from onion skin. J. Food Eng. 102 (2011), 327–333.
132. Li, B., Xu, Y., Jin, Y.-X., Wu, Y.-Y., Tu, Y.-Y., Response surface optimization of supercritical fluid extraction of kaempferol glycosides from tea seed cake. Ind. Crops Prod. 32 (2010), 123–128.
133. De-Xing, H., Potential mechanisms of cancer chemoprevention by anthocyanins. Curr. Mol. Med. 3 (2003), 149–159.
134. Wang, H., Nair, M.G., Strasburg, G.M., Chang, Y.C., Booren, A.M., Gray, J.I., DeWitt, D.L., Antioxidant and antiinflammatory activities of anthocyanins and their aglycon, cyanidin, from tart cherries. J. Nat. Prod. 62 (1999), 294–296.
135. Cvjetko Bubalo, M., Ćurko, N., Tomašević, M., Kovačević Ganić, K., Radojčić Redovniković, I., Green extraction of grape skin phenolics by using deep eutectic solvents. Food Chem. 200 (2016), 159–166.
136. Jeong, K.M., Zhao, J., Jin, Y., Heo, S.R., Han, S.Y., Yoo da, E., Lee, J., Highly efficient extraction of anthocyanins from grape skin using deep eutectic solvents as green and tunable media. Arch. Pharm. Res. 38 (2015), 2143–2152.
137. Radošević, K., Ćurko, N., Gaurina Srček, V., Cvjetko Bubalo, M., Tomašević, M., Kovačević Ganić, K., Radojčić Redovniković, I., Natural deep eutectic solvents as beneficial extractants for enhancement of plant extracts bioactivity. LWT - Food Sci. Technol. 73 (2016), 45–51.
138. Huang, Y., Feng, F., Jiang, J., Qiao, Y., Wu, T., Voglmeir, J., Chen, Z.-G., Green and efficient extraction of rutin from tartary buckwheat hull by using natural deep eutectic solvents. Food Chem. 221 (2017), 1400–1405.
139. Kanagasabapathy, G., Chua, K.H., Malek, S.N.A., Vikineswary, S., Kuppusamy, U.R., AMP-activated protein kinase mediates insulin-like and lipo-mobilising effects of β-glucan-rich polysaccharides isolated from Pleurotus sajor-caju (Fr.), Singer mushroom, in 3T3-L1 cells. Food Chem. 145 (2014), 198–204.
140. Zhang, L., Wang, M., Optimization of deep eutectic solvent-based ultrasound-assisted extraction of polysaccharides from Dioscorea opposita Thunb. Int. J. Biol. Macromol. 95 (2017), 675–681.
141. Mizuno, T., The extraction and development of antitumor-active polysaccharides from medicinal mushrooms in Japan (review). Int. J. Med. Mushrooms 1 (1999), 9–29.
142. Chen, R., Li, S., Liu, C., Yang, S., Li, X., Ultrasound complex enzymes assisted extraction and biochemical activities of polysaccharides from Epimedium leaves. Process Biochem. 47 (2012), 2040–2050.
143. van de Velde, F., Gerhard, A.D.R. Dr., Carrageenan, Biopolymers Online. 2005, Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany.
144. Das, A.K., Sharma, M., Mondal, D., Prasad, K., Deep eutectic solvents as efficient solvent system for the extraction of kappa-carrageenan from Kappaphycus alvarezii. Carbohydr. Polym. 136 (2016), 930–935.
145. Phang, S.-M., Potential products from tropical algae and seaweeds, especially with reference to Malaysia. Malays. J. Sci. 29 (2010), 160–166.
146. Sharma, M., Mondal, D., Singh, N., Trivedi, N., Bhatt, J., Prasad, K., High concentration DNA solubility in bio-ionic liquids with long-lasting chemical and structural stability at room temperature. RSC Adv. 5 (2015), 40546–40551.
147. Sharma, M., Prakash Chaudhary, J., Mondal, D., Meena, R., Prasad, K., A green and sustainable approach to utilize bio-ionic liquids for the selective precipitation of high purity agarose from an agarophyte extract. Green Chem. 17 (2015), 2867–2873.
148. Zeng, Q., Wang, Y., Huang, Y., Ding, X., Chen, J., Xu, K., Deep eutectic solvents as novel extraction media for protein partitioning. Analyst 139 (2014), 2565–2573.
149. Shang, Q., Xu, H., Huang, L., Tanshinone IIA: a promising natural cardioprotective agent. Evid. Based Complement. Altern. Med. 2012 (2012), 1–7.
150. Pan, X., Niu, G., Liu, H., Microwave-assisted extraction of tanshinones from Salvia miltiorrhiza bunge with analysis by high-performance liquid chromatography. J. Chromatogr. A 922 (2001), 371–375.
151. Wu, K., Zhang, Q., Liu, Q., Tang, F., Long, Y., Yao, S., Ionic liquid surfactant-mediated ultrasonic-assisted extraction coupled to HPLC: application to analysis of tanshinones in Salvia miltiorrhiza bunge. J. Sep. Sci. 32 (2009), 4220–4226.
152. Hidalgo, A., Brandolini, A., Pompei, C., Piscozzi, R., Carotenoids and tocols of einkorn wheat (Triticum monococcum ssp. monococcum L.). J. Cereal Sci. 44 (2006), 182–193.
153. Sen, C.K., Khanna, S., Roy, S., Tocotrienols in health and disease: the other half of the natural vitamin E family. Mol. Asp. Med. 28 (2007), 692–728.
154. Wiseman, H., Vitamin-D is a membrane antioxidant - ability to inhibit iron-dependent lipid-peroxidation in liposomes compared to cholesterol, ergosterol and tamoxifen and relevance to anticancer action. FEBS Lett. 326 (1993), 285–288.
155. Ha, Y.L., Storkson, J., Pariza, M.W., Inhibition of benzo(a)pyrene-induced mouse forestomach neoplasia by conjugated dienoic derivatives of linoleic-acid. Cancer Res. 50 (1990), 1097–1101.
156. Gee, P.T., Unleashing the untold and misunderstood observations on vitamin E. Genes Nutr. 6 (2011), 5–16.
157. Zoccola, M., Aluigi, A., Tonin, C., Characterisation of keratin biomass from butchery and wool industry wastes. J. Mol. Struct. 938 (2009), 35–40.
158. Idris, A., Vijayaraghavan, R., Rana, U.A., Fredericks, D., Patti, A.F., MacFarlane, D.R., Dissolution of feather keratin in ionic liquids. Green Chem. 15 (2013), 525–534.
159. Huda, S., Yang, Y., Feather fiber reinforced light-weight composites with good acoustic properties. J. Polym. Environ. 17 (2009), 131–142.
160. Xie, H., Li, S., Zhang, S., Ionic liquids as novel solvents for the dissolution and blending of wool keratin fibers. Green Chem. 7 (2005), 606–608.
161. Onifade, A., Al-Sane, N., Al-Musallam, A., Al-Zarban, S., A review: potentials for biotechnological applications of keratin-degrading microorganisms and their enzymes for nutritional improvement of feathers and other keratins as livestock feed resources. Bioresour. Technol. 66 (1998), 1–11.
162. Rouse, J.G., Van Dyke, M.E., A review of keratin-based biomaterials for biomedical applications. Materials 3 (2010), 999–1014.
163. Veves, A., Falanga, V., Armstrong, D.G., Sabolinski, M.L., Graftskin, a human skin equivalent, is effective in the management of noninfected neuropathic diabetic foot ulcers: a prospective randomized multicenter clinical trial. Diabetes Care 24 (2001), 290–295.
164. Pechter, P.M., Gil, J., Valdes, J., Tomic-Canic, M., Pastar, I., Stojadinovic, O., Kirsner, R.S., Davis, S.C., Keratin dressings speed epithelialization of deep partial-thickness wounds. Wound Repair Regen. 20 (2012), 236–242.
165. Zhou, R., Li, J., Hua, L., Yang, Z., Berne, B., Comment on “urea-mediated protein denaturation: a consensus view”. J. Phys. Chem. B 115 (2011), 1323–1326.
166. Watlaufer, D.B., Malik, S.K., Stoller, L., Coffin, R.L., Nonpolar group participation in the denaturation of proteins by urea and guanidinium salts. Model compound studies. J. Am. Chem. Soc. 86 (1964), 508–514.
167. Stumpe, M.C., Grubmüller, H., Interaction of urea with amino acids: implications for urea-induced protein denaturation. J. Am. Chem. Soc. 129 (2007), 16126–16131.
168. Frank, H.S., Franks, F., Structural approach to the solvent power of water for hydrocarbons; urea as a structure breaker. J. Chem. Phys. 48 (1968), 4746–4757.
169. Manayi, A., Nabavi, S.M., Daglia, M., Jafari, S., Natural terpenoids as a promising source for modulation of GABAergic system and treatment of neurological diseases. Pharmacol. Rep. 68 (2016), 671–679.
170. Okasaka, M., Takaishi, Y., Kashiwada, Y., Kodzhimatov, O.K., Ashurmetov, O., Lin, A.J., Consentino, L.M., Lee, K.-H., Terpenoids from Juniperus polycarpus var. seravschanica. Phytochemistry 67 (2006), 2635–2640.
171. Marimuthu, P., Wu, C.L., Chang, H.T., Chang, S.T., Antioxidant activity of the ethanolic extract from the bark of Chamaecyparis obtusa var. formosana. J. Sci. Food Agric. 88 (2008), 1400–1405.
172. Barrero, A.F., del Moral, J.F.Q.l., Herrador, M.M., Akssira, M., Bennamara, A., Akkad, S., Aitigri, M., Oxygenated diterpenes and other constituents from Moroccan Juniperus phoenicea and Juniperus thurifera var. africana. Phytochemistry 65 (2004), 2507–2515.
173. Zhao, Q.-Q., Wang, S.-F., Li, Y., Song, Q.-Y., Gao, K., Terpenoids with anti-inflammatory activity from Abies chensiensis. Fitoterapia 111 (2016), 87–94.
174. Lu, J.-J., Dang, Y.-Y., Huang, M., Xu, W.-S., Chen, X.-P., Wang, Y.-T., Anti-cancer properties of terpenoids isolated from Rhizoma Curcumae – a review. J. Ethnopharmacol. 143 (2012), 406–411.
175. Tang, B., Bi, W., Zhang, H., Row, K.H., Deep eutectic solvent-based HS-SME coupled with GC for the analysis of bioactive terpenoids in chamaecyparis obtusa leaves. Chromatographia 77 (2014), 373–377.
176. Tankeviciute, A., Kazlauskas, R., Vickackaite, V., Headspace extraction of alcohols into a single drop. Analyst 126 (2001), 1674–1677.
177. Wang, G.J., Tian, L., Fan, Y.M., Qi, M.L., Headspace single-drop microextraction gas chromatography mass spectrometry for the analysis of volatile compounds from herba asari. J. Anal. Methods Chem. 2013 (2013), 1–6.
178. Bicchi, C., Cordero, C., Liberto, E., Sgorbini, B., Rubiolo, P., Headspace sampling of the volatile fraction of vegetable matrices. J. Chromatogr. A 1184 (2008), 220–233.
179. Yan, X., Yang, C., Ren, C., Li, D., Importance of extracting solvent vapor pressure in headspace liquid-phase microextraction. J. Chromatogr. A 1205 (2008), 182–185.
180. Jackson, H., Braun, C.L., Ernst, H., The chemistry of novel xanthophyll carotenoids. Am. J. Cardiol. 101 (2008), S50–S57.
181. Juhl, A.R., Ohman, M.D., Goericke, R., Astaxanthin in Calanus pacificus: assessment of pigment-based measures of omnivory. Limnol. Oceanogr. 41 (1996), 1198–1207.
182. Naguib, Y.M., Antioxidant activities of astaxanthin and related carotenoids. J. Agric. Food. Chem. 48 (2000), 1150–1154.
183. Chew, B., Park, J., Wong, M., Wong, T., A comparison of the anticancer activities of dietary beta-carotene, canthaxanthin and astaxanthin in mice in vivo. Anticancer Res. 19 (1998), 1849–1853.
184. Lee, S.H., Park, M.S., Jung, J.Y., Jeon, C.O., Leuconostoc miyukkimchii sp. nov., isolated from brown algae (Undaria pinnatifida) kimchi. Int. J. Syst. Evol. Microbiol. 62 (2012), 1098–1103.
185. Yuan, J.-P., Peng, J., Yin, K., Wang, J.-H., Potential health-promoting effects of astaxanthin: a high-value carotenoid mostly from microalgae. Mol. Nutr. Food Res. 55 (2011), 150–165.
186. Handayani, A.D., Sutrisno, Indraswati, N., Ismadji, S., Extraction of astaxanthin from giant tiger (Panaeus monodon) shrimp waste using palm oil: studies of extraction kinetics and thermodynamic. Bioresour. Technol. 99 (2008), 4414–4419.
187. Quan, C., Turner, C., Extraction of astaxanthin from shrimp waste using pressurized hot ethanol. Chromatographia 70 (2009), 247–251.
188. Pu, J., Sathivel, S., Kinetics of lipid oxidation and degradation of flaxseed oil containing crawfish (Procambarus clarkii) Astaxanthin. J. Am. Oil Chem. Soc. 88 (2011), 595–601.
189. Seabra, L.M.J., Pedrosa, L.F.C., Astaxanthin: structural and functional aspects. Rev. Nutr. 23 (2010), 1041–1050.
190. Rao, A.R., Sarada, R., Ravishankar, G.A., Stabilization of astaxanthin in edible oils and its use as an antioxidant. J. Sci. Food Agric. 87 (2007), 957–965.
191. Zhao, S., Kwok, K.-C., Liang, H., Investigation on ultrasound assisted extraction of saikosaponins from Radix Bupleuri. Sep. Purif. Technol. 55 (2007), 307–312.
192. Leszkiewicz, B., Kasperek, M., The effect of heat treatment on fatty acids of rapeseed oils. J. Am. Oil Chem. Soc. 65 (1988), 1511–1515.