Extraction and isolation of phenolic compounds

Methods in Molecular Biology

Volumn 864, Issue , 2012, Pages 427-464

  Santos Buelga, Celestino ^a   Gonzalez Manzano, Susana ^a   Dueñas, Montserrat ^a   Gonzalez Paramas, Ana M ^a  

^a UNIVERSITY OF SALAMANCA   (Spain)

Author keywords

Assisted extraction techniques; Column chromatography; Counter current chromatography; Phenolic compounds; Sample preparation; Solid phase extraction; Solvent extraction

Indexed keywords

PHENOL DERIVATIVE; PLANT EXTRACT; SOLVENT;

ARTICLE; CHEMISTRY; COUNTER CURRENT CHROMATOGRAPHY; HYDROLYSIS; ISOLATION AND PURIFICATION; METHODOLOGY; MICROWAVE RADIATION; PLANT; SOLID PHASE EXTRACTION; SOUND; SUPERCRITICAL FLUID CHROMATOGRAPHY;

CHROMATOGRAPHY, SUPERCRITICAL FLUID; COUNTERCURRENT DISTRIBUTION; HYDROLYSIS; MICROWAVES; PHENOLS; PLANT EXTRACTS; PLANTS; SOLID PHASE EXTRACTION; SOLVENTS; SOUND;

EID: 84859833199     PISSN: 10643745     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-61779-624-1_17     Document Type: Article

References (219)

1. Quideau S, Deffi eux D, Douat-Casassus C, Pouysegu L (2011) Plant polyphenols: chemical properties, biological activities and synthesis. Angew Chem Int Ed 50:586-621
2. Robards K (2003) Strategies for the determination of bioactive phenols in plants, fruit and vegetables. J Chromatog A 1000:657-691 (Pubitemid 36638479)
3. Luthria DL (2006) Signifi cance of sample preparation in developing analytical methodologies for accurate estimation of bioactive compounds in functional foods. J Sci Food Agric 86:2266-2272 (Pubitemid 44690145)
4. Vallejo F, Tomas-Barberan F, Garcia-Viguera C (2003) Health promoting compounds in broccoli as infl uenced by refrigerated transport and retail sale period. J Agric Food Chem 51:3029-3034
5. Dai J, Mumper RJ (2010) Plant phenolics: extraction, analysis and their antioxidant and anticancer properties. Molecules 15:7313-7352
6. Keinanen M, Julkunen-Tiitto R (1996) Effect of sample preparation method on birch ( Betula pendula Roth) leaf phenolics. J Agric Food Chem 44:2724-2727 (Pubitemid 126453572)
7. Santos-Buelga C, Gonzalez-Manzano S, Dueñas M, Gonzalez-Paramas AM (2011) Analysis and characterization of flavonoid metabolites. In: Cheynier V, Quideau s (eds) Recent advances in polyphenols research, vol III. Wiley-Blackwell, Oxford, UK
8. Andreasen MF, Christensen LP, Meyer AS et al (1999) Release of hydroxycinnamic and hydroxybenzoic acids in rye by commercial plant cell wall degrading enzyme preparations. J Sci Food Agric 79:411-1413
9. Bartolomé B, Gomez-Cordoves C (1999) Barley spent grain: release of hydroxycinnamic acids (ferulic and p-coumaric acids) by commercial enzyme preparations. J Sci Food Agric 79:435-439 (Pubitemid 29150593)
10. Yu J, Vasanthan T, Temelli F (2001) Analysis of phenolic acids in barley by high-performance liquid chromatography. J Agric Food Chem 49:4352-4358 (Pubitemid 32896436)
11. Mattila P, Kumpulainen J (2002) Determination of free and total phenolic acids in plant-derived foods by HPLC with diode-array detection. J Agric Food Chem 50:3660-3667 (Pubitemid 34640687)
12. Ross KA, Beta T, Arntfi eld SD (2009) A comparative study on the phenolic acids identifi ed and quantifi ed in dry beans using HPLC as affected by different extraction and hydrolysis methods. Food Chem 113:336-344
13. Luthria DL, Pastor-Corrales MA (2006) Phenolic acids content of 15 dry edible bean ( Phaseolus vulgaris L.) varieties. J Food Compos Anal 19:205-211 (Pubitemid 43024891)
14. Rivas-Gonzalo JC (2003) Analysis of anthocyanins. In: Santos-Buelga C, Williamson G (eds) Methods in polyphenol analysis. The Royal Society of Chemistry, Cambridge, pp 338-358
15. Krygier K, Sosulski F, Hogge L (1982) Free, esterifi ed, and insoluble-bound phenolic acids. 1. Extraction and purifi cation procedure. J Agric Food Chem 30:330-334
16. Sosulski F, Krygier K, Hogge L (1982) Free, esterifi ed, and insoluble-bound phenolic acids. 3. Composition of phenolic acids in cereal and potato flours. J Agric Food Chem 30:337-340
17. Tomás-Barberán FA, Gil-Izquierdo A, Ferreres F, Gil MI (2003) Analysis and purifi cation of flavanones, chalcones and dihydrochalcones. In: Santos-Buelga C, Williamson G (eds) Methods in polyphenol analysis. The Royal Society of Chemistry, Cambridge, pp 359-371
18. Escribano-Bailon MT, Santos-Buelga C (2003) Polyphenol extraction from foods. In: Santos-Buelga C, Williamson G (eds) Methods in polyphenol analysis. The Royal Society of Chemistry, Cambridge, pp 1-16
19. Luque de Castro MD, Garcia-Ayuso LE (1998) Soxhlet extraction of solid materials: an outdated technique with a promising innovative future. Anal Chim Acta 369:1-10 (Pubitemid 28287289)
20. Santos-Buelga C, García-Viguera C, Tomás-Barberán FA (2003) On-line identifi cation of flavonoids by HPLC coupled to diode array detection. In: Santos-Buelga C, Williamson G (eds) Methods in polyphenol analysis. The Royal Society of Chemistry, Cambridge, pp 92-124
21. de Rijke E, Out P, Wilfried MA et al (2006) Analytical separation and detection methods for flavonoids. J Chromatogr A 1112:31-63
22. Naczk M, Shahidi F (2004) Extraction and analysis of phenolics in food. J Chromatogr A 1054:95-111 (Pubitemid 39445814)
23. Naczk M, Shahidi F, Sullivan A (1992) Recovery of rapeseed tannins by various solvent systems. Food Chem 45:51-54
24. Antolovich M, Prenzler P, Robards K, Ryan D (2000) Sample preparation in the determination of phenolic compounds in fruits. Analyst 125:989-1009 (Pubitemid 30319148)
25. King GA, Sweeny JC, Radford T, Iacobucci GA (1979) The ascorbic acid/O2 degradation of anthocyanidin. Bull Liaison Groupe Polyphenols 9:121-128
26. Bradshaw MP, Prenzler PD, Scollary GR (2001) Ascorbic acid-induced browning of (+)-catechin in a model wine system. J Agric Food Chem 49:934-939 (Pubitemid 32172650)
27. Luque-Garcia JL, Luque de Castro MD (2004) Ultrasound-assisted Soxhlet extraction: an expeditive approach for solid sample treatment. Application to the extraction of total fat from oleaginous seeds. J Chromatogr A 1034:237-242 (Pubitemid 38376437)
28. Kataoka H (2010) New trends in sample preparation for analysis of plant-derived medicines. Curr Organ Chem 14:1698-1713
29. Priego-Capote F, Luque de Castro MD (2007) Ultrasound in analytical chemistry. Anal Bioanal Chem 387:249-257
30. Ma YQ, Chen JC, Liu DH et al (2009) Simultaneous extraction of phenolic compounds of citrus peel extracts: Effect of ultrasound. Ultrason Sonochem 16:57-62
31. Ma YQ, Ye XQ, Hao YB et al (2008) Ultrasound-assisted extraction of hesperidin from Penggan ( Citrus reticulata ) peel. Ultrason Sonochem 15:227-232
32. Adam M, Dobias P, Eisner A et al (2009) Extraction of antioxidants from plants using ultrasonic methods and their antioxidant capacity. J Sep Sci 32:288-294
33. Chukwumah YC, Walker LT, Verghese M et al (2009) Effect of frequency and duration of ultrasonication on the extraction effi ciency of selected isofl avones and trans-resveratrol from peanuts ( Arachis hypogaea ). Ultrason Sonochem 16:293-299
34. Khan MK, Abert-Vian M, Fabiano-Tixier AS et al (2010) Ultrasound-assisted extraction of polyphenols (fl avanone glycosides) from orange ( Citrus sinensis L.) peel. Food Chem 119:851-858
35. Wang J, Su BG, Cao YP et al (2008) Optimisation of ultrasound-assisted extraction of phenolic compounds from wheat bran. Food Chem 106:804-810 (Pubitemid 47332891)
36. Ghafoor K, Choi YH, Jeon JY, Jo IH (2009) Optimization of ultrasound-assisted extraction of phenolic compounds, antioxidants, and anthocyanins from grape ( Vitis vinifera ) seeds. J Agric Food Chem 57:4988-4994
37. Rostagno MA, Palma M, Barroso CG (2007) Ultrasound-assisted extraction of isofl avones from soy beverages blended with fruit juices. Anal Chim Acta 597:265-272 (Pubitemid 47193203)
38. Jerman T, Trebse P, Vodopivec BM (2010) Ultrasound-assisted solid liquid extraction (USLE) of olive fruit ( Olea europaea ) phenolic compounds. Food Chem 123:175-182
39. Staneva J, Todorova M, Neykov N, Evstatieva L (2009) Ultrasonically assisted extraction of total phenols and flavonoids from Rhodiola rosea . Nat Prod Comm 4:935-938
40. Luque de Castro MD, Priego-Capote F (2007) Ultrasound assistance to liquid-liquid extraction: a debatable analytical tool. Anal Chim Acta 583:2-9 (Pubitemid 46043337)
41. Wang LJ, Weller CL (2006) Recent advances in extraction of nutraceuticals from plants. Trends Food Sci Technol 17:300-312
42. Kaufmann B, Christen P (2002) Recent extraction techniques for natural products: microwave-assisted extraction and pressurised solvent extraction. Phytochem Anal 13:105-113 (Pubitemid 34285524)
43. Eskilsson CS, Bjorklund E (2000) Analytical-scale microwave-assisted extraction. J Chromatogr 902:227-250
44. Pérez-Serradilla JA, Japon-Lujan R, Luque de Castro MD (2007) Simultaneous microwaveassisted solid-liquid extraction of polar and nonpolar compounds from alperujo. Anal Chim Acta 602:82-88 (Pubitemid 47542309)
45. Pérez-Serradilla JA, Luque de Castro MD (2010) Microwave-assisted extraction of phenolic compounds from wine lees and spraydrying of the extract. Food Chem 124:1652-1659
46. Proestos C, Komaitis M (2008) Application of microwave-assisted extraction to the fast extraction of plant phenolic compounds. LWT-Food Sci Technol 41:652-659
47. Xiao WH, Han LJ, Shi B (2008) Microwaveassisted extraction of flavonoids from Radix Astragali. Sep Purif Technol 62:614-618
48. Bai X, Yue TL, Yuan YH et al (2010) Optimization of microwave-assisted extraction of polyphenols from apple pomace using response surface methodology and HPLC analysis. J Sep Sci 33:3751-3758
49. Ballard TS, Mallikarjunan P, Zhou K, O'Keefe S (2010) Microwave-assisted extraction of phenolic antioxidant compounds from peanut skins. Food Chem 120:1185-1192
50. Gallo M, Ferracane R, Graziani G et al (2010) Microwave assisted extraction of phenolic compounds from four different ápices. Molecules 15:6365-6374
51. Terigar BG, Balasubranian S, Boldor D et al (2010) Continuous microwave-assisted isofl avone extraction system: design and performance evaluation. Bioresouce Technol 101:2466-2471
52. Du FY, Xiao XH, Li GK (2007) Application of ionic liquids in the microwave-assisted extraction of trans-resveratrol from Rhizma Polygoni Cuspidati . J Chromatogr A 1140:56-62
53. Du FY, Xiao XH, Luo XJ et al (2009) Application of ionic liquids in the microwaveassisted extraction of polyphenolic compounds from medicinal plants. Talanta 78:1177-1184
54. Liazid A, Palma M, Brigui J, Barroso CG (2007) Investigation on phenolic compounds stability during microwave-assisted extraction. J Chromatogr A 1140:29-34 (Pubitemid 46039772)
55. Carabias-Martinez R, Rodriguez-Gonzalo E, Revilla-Ruiz P, Hernandez-Mendez J (2005) Pressurized liquid extraction in the analysis of food and biological samples. J Chromatogr A 1089:1-17 (Pubitemid 41073550)
56. Casazza AA, Aliakbarian B, Mantenga S et al (2010) Extraction of phenolics from Vitis vinifera wastes using non-conventional techniques. J Food Eng 100:50-55
57. Soltoft M, Christensen JH, Nielsen J et al (2009) Pressurised liquid extraction of flavonoids in onions. Method development and validation. Talanta 80:269-278
58. Zgórka G (2009) Pressurized liquid extraction versus other extraction techniques in micropreparative isolation of pharmacologically active isofl avones from Trifolium L. species. Talanta 79:46-53
59. Dobias P, Pavlikova P, Adam M et al (2010) Comparison of pressurised fluid and ultrasonic extraction methods for analysis of plant antioxidants and their antioxidant capacity. Cent Eur J Chem 8:87-95
60. Palma M, Pineiro Z, Barroso CG (2001) Stability of phenolic compounds during extraction with superheated solvents. J Chromatogr A 921:169-174 (Pubitemid 32537822)
61. Wijngaard H, Brunton N (2009) The optimization of extraction of antioxidants from apple pomace by pressurized liquids. J Agric Food Chem 57:10625-10631
62. Howard L, Pandjaitan N (2008) Pressurized liquid extraction of flavonoids from spinach. J Food Sci 73:C151-C157 (Pubitemid 351489941)
63. Ju ZY, Howard LR (2003) Effects of solvent and temperature on pressurized liquid extraction of anthocyanins and total phenolics from dried red grape skin. J Agric Food Chem 51:5207-5213
64. Luque-Rodriguez JM, Luque de Castro MD, Perez-Juan P (2007) Dynamic superheated liquid extraction of anthocyanins and other phenolics from red grape skins of winemaking residues. Bioresour Technol 98:2705-2713 (Pubitemid 46498740)
65. Alonso-Salces RM, Korta E, Barranco A et al (2001) Pressurized liquid extraction for the determination of polyphenols in apple. J Chromatogr A 933:37-43 (Pubitemid 33043739)
66. Monrad JK, Howard LR, King JW et al (2010) Subcritical solvent extraction of procyanidins from dried red grape pomace. J Agric Food Chem 58:4014-4021
67. Chen XJ, Guo BL, Li SP et al (2007) Simultaneous determination of 15 flavonoids in Epimedium using pressurized liquid extraction and high-performance liquid chromatography. J Chromatogr A 1163:96-104 (Pubitemid 47247697)
68. Herrero M, Ibanez E, Senorans FJ, Cifuentes A (2004) Pressurized liquid extracts from Spirulina platensis microalga: determination of their antioxidant activity and preliminary analysis by micellar electrokinetic chromatography. J Chromatogr A 1047:195-203 (Pubitemid 39164691)
69. Ibanez E, Herrero M, Martin-Alvarez PJ (2006) Accelerated solvent extraction: a new procedure to obtain functional ingredients from natural sources. In: Turner C (ed) Modern extraction techniques; ACS Symposium Series, vol 925. American Chemical Society, Washington DC, pp 65-78
70. Runnqvist H, Bak SA, Hansen M et al (2010) Determination of pharmaceuticals in environmental and biological matrices using pressurised liquid extraction-Are we developing sound extraction methods? J Chromatogr A 1217:2447-2470
71. Chen Y, Guoa A, Wang X et al (2008) Sample preparation. J Chromatog A 1184:191-219 (Pubitemid 351296221)
72. Garcia-Marino M, Rivas-Gonzalo JC, Ibanez E, Garcia-Moreno C (2006) Recovery of catechins and proanthocyanidins from winery by-products using subcritical water extraction. Anal Chim Acta 563:44-50
73. Kim WJ, Kim J, Veriansyah B et al (2009) Extraction of bioactive components from Centella asiatica using subcritical water. J Sup Fluid 48:211-216
74. Kim JW, Nagaoka T, Ishida Y et al (2009) Subcritical water extraction of nutraceutical compounds from citrus pomaces. Sep Sci Technol 44:2598-2608
75. Rodriguez-Meizoso I, Marin FR, Herrero M et al (2006) Subcritical water extraction of nutraceuticals with antioxidant activity from oregano. Chemical and functional characterization. J Pharm Biome Anal 41:1560-1565 (Pubitemid 44247456)
76. Hartonen K, Parshintsev J, Sandberg K et al (2007) Isolation of flavonoids from aspen knotwood by pressurized hot water extraction and comparison with other extraction techniques. Talanta 74:32-38 (Pubitemid 47632730)
77. Fabian C, Tran-Thi NY, Kasim NS et al (2010) Release of phenolic acids from defatted rice bran by subcritical water treatment. J Sci Food Agric 90:2576-2581
78. Ibanez E, Kubatova A, Senorans FJ et al (2003) Subcritical water extraction of antioxidant compounds from rosemary plants. J Agric Food Chem 51:375-382
79. Nováková L, Vl ková H (2009) A review of current trends and advances in modern bioanalytical methods: chromatography and sample preparation. Anal Chim Acta 656:8-35
80. Fritz JS, Dumont PJ, Schmidt LW (1995) Methods and materials for solid-phase extraction. J Chromatogr A 691:133-140
81. Kalt W, MacKinnon S, McDonald J et al (2008) Phenolics of Vaccinium berries and other fruit crops. J Sci Food Agric 88:68-76
82. Wallace TC, Giusti MM (2010) Extraction and normal-phase HPLC-fl uorescenceelectrospray MS characterization and quantifi cation of procyanidins in cranberry extracts. J Food Sci 75:C690-C696
83. Budryn G, Nebesny E, Podsddek A et al (2009) Effect of different extraction methods on the recovery of chlorogenic acids, caffeine and Maillard reaction products in coffee beans. Eur Food Res Technol 228:913-922
84. Zgorka G, Hajnos A (2003) The application of solid-phase extraction and reversed phase high-performance liquid chromatography for simultaneous isolation and determination of plant flavonoids and phenolic acids. Chromatographia 57:S77-S80 (Pubitemid 36609396)
85. Bendini A, Bonoli M, Cerretani L et al (2003) Liquid-liquid and solid-phase extractions of phenols from virgin olive oil and their separation by chromatographic and electrophoretic methods. J Chromatogr A 985:425-433 (Pubitemid 36164832)
86. Poole CF (2003) New trends in solid-phase extraction. Trends Anal Chem 22:362-373 (Pubitemid 36694982)
87. Fontanals N, Marce RM, Borrull F (2005) New hydrophilic materials for solid-phase extraction. Trends Anal Chem 24:394-406 (Pubitemid 40615868)
88. Ferreres F, Tomas-Barberan FA, Soler C et al (1994) A simple extractive technique for honey flavonoid HPLC analysis. Apidologie 25:21-30
89. Pérez-Magariño S, Ortega-Heras M, Cano-Mozo E (2008) Optimization of a solid-phase extraction method using copolymer sorbents for isolation of phenolic compounds in red wines and quantifi cation by HPLC. J Agric Food Chem 56:11560-11570
90. Michalkiewicz A, Biesaga M, Pyrzynska K (2008) Solid-phase extraction procedure for determination of phenolic acids and some flavonols in honey. J Chromatogr A 1187:18-24
91. Jeffery DW, Mercurio MD, Herderich MJ et al (2008) Rapid isolation of red wine polymeric polyphenols by solid-phase extraction. J Agric Food Chem 56:2571-2580 (Pubitemid 351685194)
92. Waksmundzka-Hajnos M, Wianowska D, Oniszczuk A et al (2008) Effect of samplepreparation methods on the quantifi cation of selected flavonoids in plant materials by HPLC. Acta Chromatogr 20:475-488
93. Xing J, Xie CF, Lou HX (2007) Recent applications of liquid chromatography-mass spectrometry in natural products bioanalysis. J Pharm Biomed Anal 44:368-378 (Pubitemid 46880088)
94. Lu Y, Shen Q, Dai Z (2011) Multiwalled carbon nanotubes as sorbent for online solidphase extraction of resveratrol in red wines prior to fused-core C18-based ultrahigh-performance liquid chromatography-tandem mass spectrometry quantifi cation. J Agric Food Chem 59:70-77
95. Lam SH, Wang CY, Chen CK et al (2007) Chemical investigation of Phyllanthus reticulatus by HPLC-SPE-NMR and conventional methods. Phytochem Anal 18:251-255
96. Miliauskas G, van Beek TA, de Waard P et al (2006) Comparison of analytical and semi-preparative columns for high-performance liquid chromatography-solid-phase extraction-nuclear magnetic resonance. J Chromatogr A 1112: 276-284
97. Tatsis EC, Boeren S, Exarchou V et al (2007) Identifi cation of the major constituents of Hypericum perforatum by LC/SPE/NMR and/or LC/MS. Phytochemistry 68:383-393 (Pubitemid 46108047)
98. Kumar A, Malika AK, Tewary DK (2009) A new method for determination of myricetin and quercetin using solid phase microextractionhigh performance liquid chromatography-ultra violet/visible system in grapes, vegetables and red wine samples. Anal Chim Acta 631:177-181
99. Mitani K, Narimatsu S, Kataoka H (2003) Determination of daidzein and genistein in soybean foods by automated on-line in-tube solid-phase microextraction coupled to highperformance liquid chromatography. J Chromatogr A 986:169-177 (Pubitemid 36126457)
100. Viñas P, Campillo N, Hernández-Pérez M (2008) A comparison of solid-phase microextraction and stir bar sorptive extraction coupled to liquid chromatography for the rapid analysis of resveratrol isomers in wines, musts and fruit juices. Anal Chim Acta 611:119-125
101. Ziakova A, Brandstecerova E, Blahova E (2003) Matrix solid-phase dispersion for the liquid chromatographic determination of phenolic acids in Melissa offi cinalis . J Chromatogr A 983:271-275 (Pubitemid 35461883)
102. Barfi B, Hadjmohammadi MR, Kasaai MR (2009) Determination of daidzein and genistein in soybean and its waste by matrix solid-phase dispersion extraction and HPLC. Monatsh Chem 140:1143-1148
103. Lahoutifard N, Dawes P, Wynne P. (2010) Micro extraction packed sorbent (MEPS): analysis of food and beverage. http://www. sisweb.com/lc/sge/meps.pdf Accessed 28 January 2011.
104. Wirth HJ, Lahoutifard N, Wynne P (2010) Measuring fruit juice adulteration by changes in flavonoid content using MEPS and HPLC. http://www.cromlab.es/Artículos/SGE/MEPS/TP-0199-M-RevB.pdf . Accessed 28 January 2011
105. Haginaka J (2009) Molecularly imprinted polymers as affi nity-based separation media for sample preparation. J Sep Sci 32:1548-1565
106. Stalikas CD (2007) Extraction, separation, and detection methods for phenolic acids and flavonoids. J Sep Sci 30:3268-3295
107. Xie JC, Zhu L, Luo H et al (2001) Direct extraction of specifi c pharmacophoric flavonoids from gingko leaves using a molecularly imprinted polymer for quercetin. J Chromatogr A 934:1-11 (Pubitemid 33043724)
108. Weiss R, Molinelli A, Lakusch M, Mizaikoff B (2002) Molecular imprinting and solid phase extraction of flavonoid compounds. Bioseparation 10:379-387
109. Theodoridis G, Lasakova M, Skerikova V et al (2006) Molecular imprinting of natural flavonoid antioxidants: Application in solidphase extraction for the sample pretreatment of natural products prior to HPLC analysis. J Sep Sci 29:2310-2321 (Pubitemid 44649645)
110. Xia YQ, Guo TY, Song MD et al (2006) Selective separation of quercetin by molecular imprinting using chitosan beads as functional matrix. React Funct Polym 66:1734-1740
111. Molinelli A, Weiss R, Mizaikoff B (2002) Advanced solid phase extraction using molecularly imprinted polymers for the determination of quercetin in red wine. J Agric Food Chem 50:1804-1808 (Pubitemid 34259970)
112. O'Mahony J, Wei S, Molinelli A, Mizaikoff B (2006) Imprinted polymeric materials. Insight into the nature of prepolymerization complexes of quercetin imprinted polymers. Anal Chem 78:6187-6190 (Pubitemid 44360132)
113. Zhang Y, Li SF, Wu XW et al (2007) Macroporous resin adsorption for purifi cation of flavonoids in Houttuynia cordata Thunb. Chinese J Chem Eng 15:872-876
114. Blahova E, Lehotay J, Skacani I (2004) The use of molecularly imprinted polymer for selective extraction of catechin. J Liq Chromatog Rel Techn 27:2715-2731 (Pubitemid 39346650)
115. Ding L, Li H, Tang F, Yao S (2006) Molecularly imprinted solid-phase extraction of epicatechin from tea beverage. Anal Let 39:2373-2385 (Pubitemid 44433206)
116. Haginaka J, Tabo H, Ichitani M et al (2007) Uniformly-sized, molecularly imprinted polymers for (-)-epigallocatechin gallate,-epicatechin gallate and-gallocatechin gallate by multi-step swelling and polymerization method. J Chromatogr A 1156:45-50 (Pubitemid 46935709)
117. Cao H, Xiao JB, Xu M (2006) Evaluation of new selective molecularly imprinted polymers for the extraction of resveratrol from Polygonum cuspidatum . Macromol Res 14:324-330 (Pubitemid 44032884)
118. Zhang Z, Liu L, Li H, Yao SZ (2009) Synthesis, characterization and evaluation of uniformly sized core-shell imprinted microspheres for the separation trans-resveratrol from giant knotweed. Appl Surf Sci 255:9327-9332
119. Ma SJ, Zhuang X, Wang H et al (2007) Preparation and characterization of trans-resveratrol imprinted polymers. Anal Let 40:321-333 (Pubitemid 47250586)
120. Sun BW, Li YZ, Chang WB (2001) Molecularly imprinted polymer using p-hydroxybenzoic acid, p-hydroxyphenylacetic acid and p-hydroxyphenylpropionic acid as templates. J Mol Recognit 14:388-392 (Pubitemid 34085334)
121. Huang X, Kong L, Li X et al (2003) Molecular imprinting of nitrophenol and hydroxybenzoic acid isomers: effect of molecular structure and acidity on imprinting. J Mol Recognit 16:406-411 (Pubitemid 38161968)
122. Liu ZS, Xu LY, Yan C, Gao RY (2004) Preparation and characterization of molecularly imprinted monolithic column based on 4-hydroxybenzoic acid for the molecular recognition in capillary electrochromatography. J Chromatogr A 523:243-250 (Pubitemid 39221447)
123. Karasova G, Lehotay J, Sadecka J et al (2005) Selective extraction of derivates of p-hydroxybenzoic acid from plant material by using a molecularly imprinted polymer. J Sep Sci 28:2468-2476 (Pubitemid 43055946)
124. Michailof C, Manesiotis P, Panayiotou C (2008) Synthesis of caffeic acid and p-hydroxybenzoic acid molecularly imprinted polymers and their application for the selective extraction of polyphenols from olive mill waste waters. J Chromatogr A 1182:25-33
125. Li H, Nie L, Yao S (2004) Adsorption isotherms and sites distribution of caffeic acid-imprinted polymer monolith from frontal analysis. Chromatographia 60:425-431 (Pubitemid 39462873)
126. Li H, Liu YG, Zhang Z et al (2005) Separation and purifi cation of chlorogenic acid by molecularly imprinted polymer monolithic stationary phase. J Chromatogr A 1098:66-74 (Pubitemid 41682410)
127. Pereira CG, Meireles MAA (2010) Supercritical fluid extraction of bioactive compounds: fundamentals, applications and economic perspectives. Food Bioprocess Technol 3:340-372
128. Liu EH, Qi LW, Cao J et al (2008) Advances of modern chromatographic and electrophoretic methods in separation and analysis of flavonoids. Molecules 13:2521-2544
129. Zuo YB, Zeng AW, Yuan XG et al (2008) Extraction of soybean isofl avones from soybean meal with aqueous methanol modifi ed supercritical carbon dioxide. J Food Eng 89:384-389
130. Lin MC, Tsai MJ, Wen KC (1999) Supercritical fluid extraction of flavonoids from Scutellariae Radix. J Chromatogr A 830:387-395
131. Araujo JMA, Silva MV, Chaves JBP (2007) Supercritical fluid extraction of daidzein and genistein isofl avones from soybean hypocotyl after hydrolysis with endogenous betaglucosidases. Food Chem 105:266-272 (Pubitemid 47016785)
132. Cavero S, Garcia-Risco MR, Marin FR et al (2006) Supercritical fluid extraction of antioxidant compounds from oregano-Chemical and functional characterization via LC-MS and in vitro assays. J Superc Fluid 38:62-69 (Pubitemid 44093192)
133. Liza MS, Rahman RA, Mandana B et al (2010) Supercritical carbon dioxide extraction of bioactive flavonoid from Strobilanthes crispus (Pecah Kaca). Food Bioprod Proc 88:319-326
134. Miao SF, Yu JP, Du Z et al (2010) Supercritical fluid extraction and micronization of ginkgo flavonoids from Ginkgo biloba leaves. Ind Eng Chem Res 49:5461-5466
135. Ghafoor K, Park J, Choi YH (2010) Optimization of supercritical fluid extraction of bioactive compounds from grape ( Vitis labrusca B.) peel by using response surface methodology. Inn Food Sci Emerg Technol 11:485-490
136. Takeuchi TM, Rubano ML, Meireles MAA (2010) Characterization and functional properties of macela ( Achyrocline satureioides ) extracts obtained by supercritical fluid extraction using mixtures of CO 2 plus ethanol. Food Bioprocess Technol 3:804-812
137. Pinelo M, Ruiz-Rodriguez A, Sineiro J et al (2007) Supercritical fluid and solid-liquid extraction of phenolic antioxidants from grape pomace: a comparative study. Eur Food Res Technol 226:199-205 (Pubitemid 47460733)
138. Bergeron C, Gafner S, Clausen E et al (2005) Comparison of the chemical composition of extracts from Scutellaria laterifl ora using accelerated solvent extraction and supercritical fluid extraction versus standard hot water or 70% ethanol extraction. J Agric Food Chem 53:3076-3080 (Pubitemid 40525272)
139. Ligor M, Kornysova O, Maruska A et al (2008) Determination of flavonoids in tea and Rooibos extracts by TLC and HPLC. J Planar Chromatog-Modern TLC 21:355-360
140. Scalia S, Giuffreda L, Pallado P (1999) Analytical and preparative supercritical fluid extraction of Chamomile flowers and its comparison with conventional methods. J Pharm Biomed Anal 21:549-558 (Pubitemid 29512220)
141. Klejdus B, Lojkova L, Lapcik O et al (2005) Supercritical fluid extraction of isofl avones from biological samples with ultra-fast highperformance liquid chromatography/mass spectrometry. J Sep Sci 28:1334-1346 (Pubitemid 41195342)
142. Nakornriab M, Sriseadka T, Wongpornchai S (2008) Quantifi cation of carotenoid and flavonoid components in brans of some Thai black rice cultivars using supercritical fluid extraction and high-performance liquid chromatography-mass spectrometry. J Food Lipid 15:488-503
143. Petsalo A, Jalonen J, Tolonen A (2006) Identifi cation of flavonoids of Rhodiola rosea by liquid chromatography-tandem mass spectrometry. J Chromatogr A 1112:224-231
144. Vatai T, Škerget M, Knez Ž (2009) Extraction of phenolic compounds from elderberry and different grape marc varieties using organic solvents and/or supercritical carbon dioxide. J Food Eng 90:246-254
145. Magalhães PJ, Vieira JS, Gonçalvez LM (2010) Isolation of phenolic compounds from hop extracts using polyvinylpolypyrrolidone: Characterization by high-performance liquid chromatography-diode array detection-electrospray tandem mass spectrometry. J Chromatogr A 1217:3258-3268
146. Rossler KH, Goodwin RS (1983) A general use of Amberlite XAD-2 resin for the purifi-cation of flavonoids from aqueous fractions. J Nat Prod 47:188
147. Llorach R, Gil-Izquierdo A, Ferreres F, Tomas-Barberan FA (2003) HPLC-DAD-MS/MS ESI characterization of unusual highly glycosylated acylated flavonoids from caulifl ower ( Brassica oleracea L. var. botrytis ) agroindustrial byproducts. J Agric Food Chem 51:3895-3899
148. Estevinho L, Pereira AP, Moreira L et al (2008) Antioxidant and antimicrobial effects of phenolic compounds extracts of Northeast Portugal honey. Food Chem Toxicol 46:3774-3779
149. Strack D, Mansell RL (1975) Polyamide column chromatography for resolution of complex mixtures of anthocyanins. J Chromatogr A 109:325-331
150. Li MX, Zhang R, Jia ZP et al (2009) Isolation and identifi cation of hemostatic ingredients from Lamiophlomis rotata (Benth.) Kudo. Phytoter Res 23:816-822
151. Zhang J, Hayat K, Zhang X et al (2010) Separation and purifi cation of flavonoid from ginkgo extract by polyamide resin. Sep Sci Technol 45:2413-2419
152. Thompson RS, Jacques D, Haslam E, Tanner RIB (1972) Plant procyanidins. Part I. Introduction: the isolation, structure and distribution in nature of plant procyanidins. J Chem Soc Perkin Trans 1:1387
153. Lea AGH, Timberlake CF (1974) The phenolics of cider. I. Procyanidins. J Sci Food Agric 25:471-477
154. Strumeyer DH, Malin MJ (1975) Condensed tannins in grain Sorghum: isolation, fractionation, and characterization. J Agric Food Chem 23:909-914
155. Asquith TN, Izuno CC, Butler LG (1983) Characterization of the condensed tannin (proanthocyanidin) from a group II sorghum. J Agric Food Chem 31:1299-1303
156. Nonaka G, Morimoto S, Nishioka I (1983) Tannins and related compounds. Part 13. Isolation and structures of trimeric, tetrameric and pentameric proanthocyanidins from cinnamon. J Chem Soc Perkin Trans 1:2139
157. Escribano-Bailón MT, Gutiérrez-Fernández Y, Rivas-Gonzalo JC, Santos-Buelga C (1992) Characterization of procyanidins of Vitis vinifera , variety Tinta del País, grape seeds. J Agric Food Chem 40:1794-1799
158. Amarowicz R, Shahidi F (1996) A rapid chromatographic method for separation of individual catechins from green tea. Food Res Int 29:71-76 (Pubitemid 27099117)
159. Derdelinckx G, Jerumanis J (1984) Separation of malt and hop proanthocyandins on Fractogel TSK HW-40 (S). J Chromatogr 285:231-234
160. Labarbe B, Cheynier V, Brossaud F et al (1999) Quantitative fractionation of grape proanthocyanidins according to their degree of polymerization. J Agric Food Chem 47:2719-2723 (Pubitemid 29396346)
161. Yanagida A, Shoji T, Shibusawa Y (2003) Separation of proanthocyanidins by degree of polymerization by means of size-exclusion chromatography and related techniques. J Biochem Biophys Methods 56:311-322 (Pubitemid 36776610)
162. Mateus N, Pascual-Teresa SDE, Rivas-Gonzalo S et al (2002) Structural
163. Alcalde-Eon C, Escribano-Bailón MT, Santos-Buelga C, Rivas-Gonzalo JC (2004) Separation of pyranoanthocyanins from red wine by column chromatography. Anal Chim Acta 513:305-318 (Pubitemid 38624498)
164. Jordheim M, Fossen T, Andersen OM (2006) Preparative isolation and NMR characterization of carboxypyranoanthocyanins. J Agric Food Chem 54:3572-3577 (Pubitemid 43852830)
165. Li R, Zhao R, Zhang H et al (2010) A novel medium poly(vinyl acetate-triallyl isocyanurate-divinylbenzene) coupled with oligo-bcyclodextrin for the isolation of puerarin from pueraria flavones. Chromatographia 72:47-54
166. Berthod A, Berthod L, Armstrong DW (2005) Selectivity of a native b-cyclodextrin column in the separation of catechin. J Liq Chromatog Rel Techn 28:1669-1678 (Pubitemid 40981441)
167. Xu J, Zhang G, Tan T, Janson JC (2005) One-step purifi cation of epigallocatechin gallate from crude green tea extracts by isocratic hydrogen bond adsorption chromatography on b-cyclodextrin substituted agarose gel media. J Chromatogr B 824:323-326 (Pubitemid 41215614)
168. Si-Ahmed K, Tazerouti F, Badjah-Hadj-Ahmed AY et al (2010) Optical isomer separation of flavanones and flavanone glycosides by nano-liquid chromatography using a phenyl-carbamate-propyl-b-cyclodextrin chiral stationary phase. J Chromatogr A 1217: 1175-1182
169. Dueñas M, Mingo-Chornet H, Perez-Alonso JJ et al (2008) Preparation of quercetin glucuronides and characterization by HPLCDAD-ESI/MS. Eur Food Res Technol 227:1069-1076
170. Gonzalez-Manzano S, Gonzalez-Paramas AM, Santos-Buelga C, Dueñas M (2009) Preparation and characterization of catechin sulfates, glucuronides, and methylethers with metabolic interest. J Agric Food Chem 57:1231-1238
171. Valls J, Millan S, Marti MP et al (2009) Advanced separation methods of food anthocyanins, isofl avones and flavanols. J Chromatogr A 1216:7143-7172
172. Liu X, Tang YH, Wei SL et al (2010) Isolation and purifi cation of phenolic compounds from Magnolia officinalis by preparative high performance liquid chromatography. J Liq Chromat Rel Techn 33:431-440
173. Lv J, Liang H, Yuan QP et al (2010) Preparative purifi cation of the major flavonoid glabridin from licorice roots by solid phase extraction and preparative high performance liquid chromatography. Sep Sci Technol 45:1104-1111
174. Han S, Kim HM, Lee JM et al (2010) Isolation and identifi cation of polymethoxyfl avones from the hybrid Citrus, Hallabong. J Agric Food Chem 58:9488-9491
175. Lazarus SA, Adamson GE, Hammerstone JF, Schmitz HH (1999) High performance liquid chromatography/mass spectrometry analysis of proanthocyanidins in foods and beverages. J Agric Food Chem 47:3693-3701 (Pubitemid 29449491)
176. Rigaud J, Escribano-Bailon MT, Prieur C et al (1993) Normal-phase high-performance liquid chromatographic separation of procyanidins from cacao beans and grape seeds. J Chromatogr A 654:255
177. Hammerstone JF, Lazarus SL, Mitchell AE et al (1999) Identifi cation of procyanidins in cocoa ( Theobroma cacao ) and chocolate using high-performance liquid chromatography/mass spectrometry. J Agric Food Chem 47:490-496 (Pubitemid 29185214)
178. Waterhouse AL, Ignelzi S, Shirley JR (2000) A comparison of methods for quantifying oligomeric proanthocyanidins from grape seed extracts. Am J Enol Vitic 51:383-389 (Pubitemid 32116880)
179. Lazarus SL, Kelm MA, Hammerstone JF et al (2003) Analysis and purifi cation of proanthocyanidin oligomers. In: Santos-Buelga C, Williamson G (eds) Methods in polyphenol analysis. The Royal Society of Chemistry, Cambridge, pp 266-283
180. Hellstrom JK, Mattila PH (2008) HPLC determination of extractable and unextractable proanthocyanidins in plant materials. J Agric Food Chem 56:7617-7624
181. Sutherland IA, Fisher D (2009) Role of counter-current chromatography in the modernisation of Chinese herbal medicines. J Chromatogr A 1216:740-753
182. Ito Y (1980) New horizontal flow-through coil planet centrifuge for counter-current chromatography. I Principle of design and analysis of acceleration. J Chromatogr 188:33-42
183. Ito Y (1980) New horizontal flow-through coil planet centrifuge for counter-current chromatography. II. The apparatus and its partition capabilities. J Chromatogr 188:43-60
184. Pauli GF, Pro SM, Friesen JB (2008) Countercurrent separation of natural products. J Nat Prod 71:1489-1508
185. Tsao R, Deng Z (2004) Separation procedures for naturally occurring antioxidant phytochemicals. J Chromatogr B 812:85-99 (Pubitemid 39535403)
186. Guzlek H, Wood PL, Janaway L (2009) Performance comparison using the GUESS mixture to evaluate counter-current chromatography instruments. J Chromatogr A 1216: 4181-4418
187. Renault JH, Thepenier P, Zeches-Hanrot M et al (1997) Preparative separation of anthocyanins by gradient elution centrifugal partition chromatography. J Chromatogr A 763:345-352 (Pubitemid 27150005)
188. Degenhardt A, Hofmann S, Knapp HP et al (2000) Preparative isolation of anthocyanins by high-speed countercurrent chromatography and application of the color activity concept to red wine. J Agric Food Chem 48:5812-5818 (Pubitemid 32063077)
189. Degenhardt A, Knapp H, Winterhalter P (2000) Rapid isolation of malvidin 3-glucoside from red wine by high speed countercurrent chromatography (HSCCC). Vitis 39:43-44 (Pubitemid 30213521)
190. Degenhardt A, Knapp H, Winterhalter P (2000) Separation and purifi cation of anthocyanins by high-speed countercurrent chromatography and screening for antioxidant activity. J Agric Food Chem 48:338-343 (Pubitemid 30120364)
191. Schwarz M, Hillebrand S, Habben S et al (2003) Application of high-speed countercurrent chromatography to the large-scale isolation of anthocyanins. Biochem Eng J 14:179-189 (Pubitemid 36569229)
192. Du Q, Jerz G, Winterhalter P (2004) Isolation of two anthocyanin sambubiosides from bilberry ( Vaccinium myrtillus ) by high-speed counter-current chromatography. J Chromatogr A 1045:59-63 (Pubitemid 39069326)
193. Du Q, Zheng J, Xu Y (2008) Composition of anthocyanins in mulberry and their antioxidant activity. J Food Compos Anal 21:390-395
194. Vidal S, Hayasaka Y, Meudec E et al (2004) Fractionation of grape anthocyanin classes using multilayer coil countercurrent chromatography with step gradient elution. J Agric Food Chem 52:713-719
195. Salas E, Dueñas M, Schwarz M et al (2005) Characterization of pigments from different high speed countercurrent chromatography wine fractions. J Agric Food Chem 53:4536-4546 (Pubitemid 40855484)
196. Rentzsch M, Quast P, Hillebrand S et al (2007) Isolation and identifi cation of 5-carboxy-pyranoanthocyanins in beverages from cherry ( Prunus cerasus L.). Innovative Food Sci Emerg Technol 8:333-338 (Pubitemid 47059025)
197. Delaunay JC, Castagnino C, Cheze C et al (2002) Preparative isolation of polyphenolic compounds from Vitis vinifera by centrifugal partition chromatography. J Chromatogr A 964:123-128 (Pubitemid 34718009)
198. Kumar NS, Rajapaksha M (2005) Separation of catechin constituents from fi ve tea cultivars using high-speed counter-current chromatography. J Chromatogr A 1083:223-228 (Pubitemid 40922690)
199. Kumar N, Maduwantha WMA, Wijekoon B et al (2009) Separation of proanthocyanidins isolated from tea leaves using high-speed countercurrent chromatography. J Chromatogr A 1216:4295-4302
200. Yanagida A, Shoji A, Shibusawa Y et al (2006) Analytical separation of tea catechins and food-related polyphenols by high-speed counter-current chromatography. J Chromatogr A 1112:195-201
201. Koehler N, Wray V, Winterhalter P (2008) Preparative isolation of procyanidins from grape seed extracts by high-speed countercurrent chromatography. J Chromatogr A 1177: 114-125 (Pubitemid 350256754)
202. Shibusawa Y, Yanagida A, Ichihashi K et al (2000) High-speed counter-current chromatography of apple procyanidins. J Chromatogr A 886:65-75
203. Sun A, Sun Q, Liu R (2007) Preparative isolation and purifi cation of flavone compounds from Sophora japonica L. by high-speed counter-current chromatography combined with macroporous resin column separation. J Sep Sci 30:1013-1019
204. Wang X, Cheng C, Sun Q et al (2005) Isolation and purifi cation of four flavonoid constituents from the flowers of Paeonia suffruticosa by high-speed counter-current chromatography. J Chromatogr A 1075:127-132
205. Chen LJ, Games DE, Jones J (2003) Isolation and identifi cation of four flavonoid constituents from the seeds of Oroxylum indicum by high-speed counter-current chromatography. J Chromatogr A 988:95-105 (Pubitemid 36165017)
206. Zhang Q, Chen LJ, Ye HY et al (2007) Isolation and purifi cation of ginkgo flavonol glycosides from Ginkgo biloba leaves by highspeed counter-current chromatography. J Sep Sci 30:2153-2158
207. Peng J, Fan G, Wu Y (2006) Preparative isolation of four new and two known flavonoids from the leaf of Patrinia villosa Juss. by counter-current chromatography and evaluation of their anticancer activities in vitro. J Chromatogr A 1115:103-111
208. Peng JY, Xu LN, Xu H et al (2007) Separation of two new prenylated dihydrofl avonoids from Dolichos tenuicaulis (Baker) Craib by high-speed counter-current chromatography. Chin J Anal Chem 35:1444-1449
209. Xu K, Lu H, Qu B et al (2010) High-speed counter-current chromatography preparative separation and purifi cation of phloretin from apple tree bark. Sep Purif Technol 72:406-409
210. Du Q, Li Z, Ito Y (2001) Preparative separation of isofl avone components in soybeans using high-speed counter-current chromatography. J Chromatogr A 923:271-274 (Pubitemid 32706402)
211. Ma X, Tu P, Chen Y (2003) Preparative isolation and purifi cation of two isofl avones from Astragalus membranaceus Bge. var. mongholicus (Bge.) Hsiao by high-speed countercurrent chromatography. J Chromatogr A 992:193-197 (Pubitemid 36349642)
212. Stuertz M, Lander V, Schmid W et al (2006) Preparative isolation of isofl avones from soy and red clover. Mol Nutr Food Res 50:356-361
213. Yang F, Ma Y, Ito Y (2001) Separation and purifi cation of isofl avones from a crude soybean extract by high-speed counter-current chromatography. J Chromatogr A 928:163-170 (Pubitemid 32822784)
214. Cao X, Tian Y, Zhang T et al (1999) Separation and purifi cation of isofl avones from Pueraria lobata by high-speed counter-current chromatography. J Chromatogr A 855:709-713 (Pubitemid 29413083)
215. Chen L, Han Y, Yang F et al (2001) Highspeed counter-current chromatography separation and purifi cation of resveratrol and piceid from Polygonum cuspidatum . J Chromatogr A 907:343-346
216. Yang F, Zhang T, Ito Y (2001) Large-scale separation of resveratrol, anthraglycoside A and anthraglycoside B from Polygonum cuspidatum Sieb. et Zucc by high-speed countercurrent chromatography. J Chromatogr A 919:443-448 (Pubitemid 32568207)
217. Liu Z, Wang J, Shen P et al (2006) Microwaveassisted extraction and high-speed countercurrent chromatography purifi cation of ferulic acid from Radix Angelicae sinensis. Sep Purif Technol 52:18-21 (Pubitemid 44633781)
218. Lu HT, Jiang Y, Chen F (2004) Application of preparative high-speed counter-current chromatography for separation of chlorogenic acid from Flos lonicerae . J Chromatogr A 1026:185-190 (Pubitemid 38045279)
219. de Beer D, Jerz G, Joubert E (2009) Isolation of isomangiferin from honeybush ( Cyclopia subternata ) using high-speed counter-current chromatography and high-performance liquid chromatography. J Chromatogr A 1216: 4282-4289