Research advances for the extraction, analysis and uses of anthraquinones: A review

Industrial Crops and Products

Volumn 94, Issue , 2016, Pages 812-833

  Duval, Johanna ^a   Pecher, Virginie ^b   Poujol, Marion ^b   Lesellier, Eric ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

^b Parfums Christian Dior   (France)

Author keywords

Analysis; Anthraquinones; Bioactive properties; Dyes; Extraction

Indexed keywords

ACIDITY; AROMATIC COMPOUNDS; CAPILLARY ELECTROPHORESIS; CHEMICAL ANALYSIS; CHROMATOGRAPHY; DYES; EFFLUENT TREATMENT; GAS CHROMATOGRAPHY; INDUSTRIAL CHEMICALS; KETONES; LIQUID CHROMATOGRAPHY; PLANTS (BOTANY); SUPERCRITICAL FLUID EXTRACTION; SUPERCRITICAL FLUIDS; ULTRASONIC APPLICATIONS;

ANALYSIS; ANTHRAQUINONE DERIVATIVES; ANTHRAQUINONES; BIOACTIVE PROPERTIES; BIOLOGICAL PROPERTIES; PHYSICOCHEMICAL PROPERTY; SUPER CRITICAL FLUID CHROMATOGRAPHY; SYNTHETIC CHEMICALS;

EXTRACTION;

BACTERIUM; BIOACTIVITY; CHEMICAL ANALYSIS; DICOTYLEDON; DYE; EXTRACTION METHOD; FUNGUS; GROWTH REGULATOR; LITERATURE REVIEW; PHYSICOCHEMICAL PROPERTY; RESEARCH WORK; RESOURCE ASSESSMENT;

CHINA;

ALOE; BACTERIA (MICROORGANISMS); FABACEAE; POLYGONACEAE; RUBIACEAE;

EID: 84991447745     PISSN: 09266690     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.indcrop.2016.09.056     Document Type: Review

References (127)

1. Agnely, M., Thiebaut, D., Dual-mode high-speed counter-current chromatography: retention, resolution and examples. J. Chromatogr. A 790 (1997), 17–30.
2. Ahmed, S., Kishikawa, N., Ohyama, K., Maki, T., Kurosaki, H., Nakashima, K., Kuroda, N., An ultrasensitive and highly selective determination method for quinones by high-performance liquid chromatography with photochemically initiated luminol chemiluminescence. J. Chromatogr. A 1216 (2009), 3977–3984, 10.1016/j.chroma.2009.03.016.
3. Ahmad, W., Zaidi, S.M.A., Mujeeb, M., Ansari, S.H., Ahmad, S., HPLC and HPTLC methods by design for quantitative characterization and in vitro anti-oxidant activity of polyherbal formulation containing Rheum emodi. J. Chromatogr. Sci. 52 (2014), 911–918.
4. Aichner, D., Ganzera, M., Analysis of anthraquinones in rhubarb (Rheum palmatum and Rheum officinale) by supercritical fluid chromatography. Talanta 144 (2015), 1239–1244, 10.1016/j.talanta.2015.08.011.
5. Arvindekar, A.U., Laddha, K.S., An efficient microwave-assisted extraction of anthraquinones from Rheum emodi: optimisation using RSM, UV and HPLC analysis and antioxidant studies. Ind. Crops Prod. 83 (2016), 587–595, 10.1016/j.indcrop.2015.12.066.
6. Ayo, R., Amupitan, J., Zhao, Y., Cytotoxicity and antimicrobial studies of 1,6,8- trihydroxy-3-methyl-anthraquinone (emodin) isolated from the leaves of Cassia nigricans Vahl. Afr. J. Biotechnol. 6 (2007), 1276–1279.
7. Azmir, J., Zaidul, I.S.M., Rahman, M.M., Sharif, K.M., Mohamed, A., Sahena, F., Jahurul, M.H.A., Ghafoor, K., Norulaini, N.A.N., Omar, A.K.M., Techniques for extraction of bioactive compounds from plant materials: a review. SI Extr. Encapsulation 117 (2013), 426–436, 10.1016/j.jfoodeng.2013.01.014.
8. Bakola-Christianopoulou, M.N., Papageorgiou, V.P., Apazidou, K.K., Gas chromatographic-mass spectrometric study of the reductive silylation of hydroxyquinones. J. Chromatogr. A 645 (1993), 293–301, 10.1016/0021-9673(93)83389-A.
9. Barrera Vázquez, M.F., Comini, L.R., Martini, R.E., Núñez Montoya, S.C., Bottini, S., Cabrera, J.L., Comparisons between conventional, ultrasound-assisted and microwave-assisted methods for extraction of anthraquinones from Heterophyllaea pustulata Hook f (Rubiaceae). Ultrason. Sonochem. 21 (2014), 478–484, 10.1016/j.ultsonch.2013.08.023.
10. Barros, I.B., de S. Daniel, J.F., Pinto, J.P., Rezende, M.I., Braz Filho, R., Ferreira, D.T., Phytochemical and antifungal activity of anthraquinones and root and leaf extracts of Coccoloba mollis on phytopathogens. Braz. Arch. Biol. Technol. 54 (2011), 535–541.
11. Bechtold, T., Mussak, R., Handbook of Natural Colorants Wiley Series in Renewable Resource. 2009, Wiley.
12. Berthod, A., Countercurrent Chromatography Comprehensive Analytical Chemistry. 2002, Elsevier Science.
13. Boldizsár, I., Szűcs, Z., Füzfai, Z., Molnár-Perl, I., Identification and quantification of the constituents of madder root by gas chromatography and high-performance liquid chromatography. J. Chromatogr. A 1133 (2006), 259–274, 10.1016/j.chroma.2006.08.021.
14. Cardon, D., Le monde des teintures naturelles. 2003, Belin.
15. Chen, T., Liu, Y., Zou, D., Chen, C., You, J., Zhou, G., Sun, J., Li, Y., Application of an efficient strategy based on liquid-liquid extraction, high-speed counter-current chromatography, and preparative HPLC for the rapid enrichment, separation, and purification of four anthraquinones from Rheum tanguticum. J. Sep. Sci. 37 (2014), 165–170, 10.1002/jssc.201300648.
16. Chien, S.-C., Wu, Y.-C., Chen, Z.-W., Yang, W.-C., Naturally occurring anthraquinones: chemistry and therapeutic potential in autoimmune diabetes. Evid. Based Complement. Alternat. Med., 13, 2015.
17. Choi, S.Z., Lee, S.O., Jang, K.U., Chung, S.H., Park, S.H., Kang, H.C., Yang, E.Y., Cho, H.J., Lee, K.R., Antidiabetic stilbene and anthraquinone derivatives fromRheum undulatum. Arch. Pharm. Res. 28 (2005), 1027–1030.
18. Dave, H., Ledwani, L., A review on anthraquinones isolated from Cassia species and their applications. Indian J. Nat. Prod. Resour. 3 (2012), 291–319.
19. Dayan, N., Kromidas, L., Formulating, Packaging, and Marketing of Natural Cosmetic Products. 2011, Wiley.
20. Derksen, G.C., Niederländer, H.A., van Beek, T.A., Analysis of anthraquinones in Rubia tinctorum L. by liquid chromatography coupled with diode-array UV and mass spectrometric detection. J. Chromatogr. A 978 (2002), 119–127.
21. Derksen, G.C.H., van Beek, T.A., de Groot, Æ., Capelle, A., High-performance liquid chromatographic method for the analysis of anthraquinone glycosides and aglycones in madder root (Rubia tinctorum L.). J. Chromatogr. A 816 (1998), 277–281.
22. Donfack, A.R.N., Tala, M.F., Wabo, H.K., Jerz, G., Zeng, G.-Z., Winterhalter, P., Tan, N.-H., Tane, P., Two new anthraquinone dimers from the stem bark of Pentas schimperi (Rubiaceae). Phytochem. Lett. 8 (2014), 55–58, 10.1016/j.phytol.2014.01.012.
23. Duval, J., Destandau, E., Pecher, V., Poujol, M., Tranchant, J.-F., Lesellier, E., Selective enrichment in bioactive compound from Kniphofia uvaria by super/subcritical fluid extraction and centrifugal partition chromatography. J. Chromatogr. A 1447 (2016), 26–38.
24. Fabbri, D., Chiavari, G., Ling, H., Analysis of anthraquinoid and indigoid dyes used in ancient artistic works by thermally assisted hydrolysis and methylation in the presence of tetramethylammonium hydroxide. J. Anal. Appl. Pyrolysis 56 (2000), 167–178, 10.1016/S0165-2370(00)00092-9.
25. Fahmy, T.M., Paulaitis, M.E., Johnson, D.M., McNally, M.E.P., Modifier effects in the supercritical fluid extraction of solutes from clay, soil, and plant materials. Anal. Chem. 65 (1993), 1462–1469, 10.1021/ac00058a026.
26. Farooq, U., Pandith, S.A., Singh Saggoo, M.I., Lattoo, S.K., Altitudinal variability in anthraquinone constituents from novel cytotypes of Rumex nepalensis Spreng—a high value medicinal herb of North Western Himalayas. Ind. Crops Prod. 50 (2013), 112–117, 10.1016/j.indcrop.2013.06.044.
27. Gao, X.-Y., Jiang, Y., Lu, J., Tu, P.-F., One single standard substance for the determination of multiple anthraquinone derivatives in rhubarb using high-performance liquid chromatography-diode array detection. Qual. Control Tradit. Chin. Med. 1216 (2009), 2118–2123.
28. Genovese, S., Tammaro, F., Menghini, L., Carlucci, G., Epifano, F., Locatelli, M., Comparison of three different extraction methods and HPLC determination of the anthraquinones aloe-emodine, emodine, rheine, chrysophanol and physcione in the bark of Rhamnus alpinus L. (Rhamnaceae). Phytochem. Anal. 21 (2010), 261–267, 10.1002/pca.1195.
29. Gong, Y.X., Li, S.P., Wang, Y.T., Li, P., Yang, F.Q., Simultaneous determination of anthraquinones in Rhubarb by pressurized liquid extraction and capillary zone electrophoresis. Electrophoresis 26 (2005), 1778–1782, 10.1002/elps.200400001.
30. Guo, S., Feng, B., Zhu, R., Ma, J., Wang, W., Preparative isolation of three anthraquinones from rumex japonicus by high-Speed counter-Current chromatography. Molecules, 16, 2011, 1201, 10.3390/molecules16021201.
31. Gupta, V.K., Tuohy, M.G., O'Donovan, A., Lohani, M., Biotechnology of bioactive compounds: sources and applications. Wiley, 2015.
32. He, D., Chen, B., Tian, Q., Yao, S., Simultaneous determination of five anthraquinones in medicinal plants and pharmaceutical preparations by HPLC with fluorescence detection. J. Pharm. Biomed. Anal. 49 (2009), 1123–1127, 10.1016/j.jpba.2009.02.014.
33. Hemwimol, S., Pavasant, P., Shotipruk, A., Ultrasound-assisted extraction of anthraquinones from roots of Morinda citrifolia. Ultrason. Sonochem. 13 (2006), 543–548, 10.1016/j.ultsonch.2005.09.009.
34. Hemwimon, S., Pavasant, P., Shotipruk, A., Microwave-assisted extraction of antioxidative anthraquinones from roots of Morinda citrifolia. Sep. Purif. Technol. 54 (2007), 44–50, 10.1016/j.seppur.2006.08.014.
35. Henriksen, L.M., Kjøsen, H., Derivatization of natural anthraquinones by reductive silylation for gas chromatographic and gas chromatographic—mass spectrometric analysis. J. Chromatogr. A 258 (1983), 252–257, 10.1016/S0021-9673(00)96420-3.
36. Husain, S., Sarma, P.N., Rao, K.S.R., Lakshmi, V.V.S., Separation and determination of reaction mixtures of anthraquinone by gas chromatography. J. Chromatogr. A 685 (1994), 356–359, 10.1016/0021-9673(94)00703-9.
37. Ibrahim, H., Mdau, B., Ahmed, A., Ilyas, M., Anthraquinones of Cissus populnea Guill & Perr (Amplidaceae). Altern. Med., 2011, 8.
38. Itoh, N., Tao, H., Ibusuki, T., In-tube silylation in combination with thermal desorption gas chromatography-mass spectrometry for the determination of hydroxy polycyclic aromatic hydrocarbons in water. Anal. Chim. Acta 555 (2006), 201–209, 10.1016/j.aca.2005.09.027.
39. Itokawa, Mihara, Takeya, Studies on a novel anthraquinone and its glycosides isolated from Rubia cordifolia and R. akane. Chem. Pharm. Bull. (Tokyo) 31 (1983), 2353–2358.
40. Jawade, N.R., Chavan, A.R., 2013. Ultrasonic-Assisted Extraction of Aloin from Aloe Vera Gel. Chem. Civ. Mech. Eng. Tracks 3rd Nirma Univ. Int. Conf. Eng. NUiCONE2012 51, 487–493. http://dx.doi.org/10.1016/j.proeng.2013.01.069.
41. Jean, B., Pharmacognosy, Phytochemistry, Medicinal Plants. 2e ed. − retirage broch, 2008, Lavoisier.
42. Khatoon, S., Role of anthraquinones as a marker and maturity in response to adventitious rooting of Tectona grandis. J. Plant Physiol., 2012.
43. Kim, Y.-M., Lee, C.-H., Kim, H.-G., Lee, H.-S., Anthraquinones isolated from Cassia tora (Leguminosae) seed show an antifungal property against phytopathogenic fungi. J. Agric. Food Chem. 52 (2004), 6096–6100.
44. Kishikawa, N., Kuroda, N., Analytical techniques for the determination of biologically active quinones in biological and environmental samples. Rev. Pap. Pharm. Biomed. Anal. 2013:87 (2014), 261–270, 10.1016/j.jpba.2013.05.035.
45. Koyama, J., Morita, I., Kobayashi, N., Simultaneous determination of anthraquinones in rhubarb by high-performance liquid chromatography and capillary electrophoresis. J. Chromatogr. A 1145 (2007), 183–189, 10.1016/j.chroma.2007.01.076.
46. Krichnavaruk, S., Shotipruk, A., Goto, M., Pavasant, P., Supercritical carbon dioxide extraction of astaxanthin from Haematococcus pluvialis with vegetable oils as co-solvent. Bioresour. Technol. 99 (2008), 5556–5560, 10.1016/j.biortech.2007.10.049.
47. Kumar, S., Srinivas, P., Rao, J., A new and convenient method for quantitative estimation of chrysophanol, an antioxidant in the rhizomes of Rheum emodi (Roxb). JPC-J. Planar Chromatogr. – Mod. TLC 15 (2002), 128–131.
48. Kuo, C.-H., Sun, S.-W., Analysis of nine rhubarb anthraquinones and bianthrones by micellar electrokinetic chromatography using experimental design. Anal. Chim. Acta 482 (2003), 47–58.
49. Lee, M.S., Sohn, C.B., Anti-diabetic properties of chrysophanol and its glucoside from rhubarb rhizome. Biol. Pharm. Bull. 31 (2008), 2154–2157.
50. Leeke, G., Gaspar, F., Santos, R., Influence of water on the extraction of essential oils from a model herb using supercritical carbon dioxide. Ind. Eng. Chem. Res. 41 (2002), 2033–2039, 10.1021/ie010845z.
51. Lesellier, E., West, C., 2015. The many faces of packed column supercritical fluid chromatography −A critical review. Ed. Choice IX 1382, 2–46. http://dx.doi.org/10.1016/j.chroma.2014.12.083.
52. Lesellier, E., Retention mechanisms in super/subcritical fluid chromatography on packed columns. Retent. Mech. Chromatogr. Electrophor. 1216 (2009), 1881–1890, 10.1016/j.chroma.2008.10.081.
53. Lin, C., Wu, C., Lin, T., Sheu, S., Determination of 19 rhubarb constituents by high-performance liquid chromatography–ultraviolet–mass spectrometry. J. Sep. Sci. 29 (2006), 2584–2593.
54. Liu, R., Li, A., Sun, A., Preparative isolation and purification of hydroxyanthraquinones and cinnamic acid from the Chinese medicinal herb Rheum officinale Baill. by high-speed counter-current chromatography. J. Chromatogr. A 1052 (2004), 217–221, 10.1016/j.chroma.2004.08.101.
55. Lo, T.C.-T., Nian, H.-C., Chiu, K.-H., Wang, A.-Y., Wu, B.-Z., Rapid and efficient purification of chrysophanol in Rheum Palmatum LINN by supercritical fluid extraction coupled with preparative liquid chromatography in tandem. J. Chromatogr. B 893–894 (2012), 101–106, 10.1016/j.jchromb.2012.02.040.
56. Locatelli, M., Genovese, S., Carlucci, G., Kremer, D., Randic, M., Epifano, F., Development and application of high-performance liquid chromatography for the study of two new oxyprenylated anthraquinones produced by Rhamnus species. J. Chromatogr. A 1225 (2012), 113–120.
57. Locatelli, M., Anthraquinones: analytical techniques as a novel tool to investigate on the triggering of biological targets. Curr. Drug Targets 12 (2011), 366–380.
58. Luthriaa, D., Vinjamoorib, D., Noelc, K., Ezzelld, J., 2004. Accelerated solvent extraction.
59. Malik, S., Sharma, N., Sharma, U.K., Singh, N.P., Bhushan, S., Sharma, M., Sinha, A.K., Ahuja, P.S., Qualitative and quantitative analysis of anthraquinone derivatives in rhizomes of tissue culture-raised Rheum emodi Wall. plants. J. Plant Physiol. 167 (2010), 749–756, 10.1016/j.jplph.2009.12.007.
60. Mehta, J., Separation and characterization of anthraquinone derivatives from Cassia fistula using chromatographic and spectral techniques. Int. J. Chem. Sci., 306, 2012.
61. Mellado, M., Madrid, A., Pena-Cortes, H., Lopez, R., Jara, C., Espinoza, L., Antioxidant activity of anthraquinones isolated from leaves of muehlenbeckia hastulata (je sm.) johnst. (polygonaceae). J. Chil. Chem. Soc. 58 (2013), 1767–1770.
62. Mester, Z., Sturgeon, R.E., Sample Preparation for Trace Element Analysis Comprehensive Analytical Chemistry. 2003, Elsevier Science.
63. Mishra, B.B., Kishore, N., Tiwari, V.K., Singh, D.D., Tripathi, V., A novel antifungal anthraquinone from seeds of Aegle marmelos Correa (family Rutaceae). Fitoterapia 81 (2010), 104–107, 10.1016/j.fitote.2009.08.009.
64. Mohammed, M., El-Souda, S.S., El-Hallouty, S.M., Kobayashi, N., Antiviral and cytotoxic activities of anthraquinones isolated from Cassia roxburghii Linn leaves. Herba Pol. 59 (2013), 33–44.
65. Moldoveanu, S.C., David, V., Modern Sample Preparation for Chromatography. 2014, Elsevier Science.
66. Pandith, S.A., Hussain, A., Bhat, W.W., Dhar, N., Qazi, A.K., Rana, S., Razdan, S., Wani, T.A., Shah, M.A., Bedi, Y.S., Hamid, A., Lattoo, S.K., Evaluation of anthraquinones from Himalayan rhubarb (Rheum emodi Wall. ex Meissn.) as antiproliferative agents. South Afr. J. Bot. 95 (2014), 1–8, 10.1016/j.sajb.2014.07.012.
67. Pereira, C.G., Meireles, M.A.A., Supercritical fluid extraction of bioactive compounds: fundamentals, applications and economic perspectives. Food Bioprocess Technol. 3 (2009), 340–372, 10.1007/s11947-009-0263-2.
68. Pongnaravane, B., Goto, M., Sasaki, M., Anekpankul, T., Pavasant, P., Shotipruk, A., 2006. Extraction of anthraquinones from roots of Morinda citrifolia by pressurized hot water: Antioxidant activity of extracts. ISSF 2005 7th Int. Symp. Supercrit. Fluids Orlando FloridaISSF 2005 7th Int. Symp. Supercrit. Fluids Orlando Fla. 37, 390–396. http://dx.doi.org/10.1016/j.supflu.2005.12.013.
69. Priya, E.S., Selvan, P.S., Prakash, P., HPTLC method development and validation for simultaneous analysis of Emodin and Chrysophanol in Cassia tora Linn methanolic extract. J. Liq. Chromatogr. Relat. Technol. 36 (2013), 2525–2533.
70. Qi, S., Cui, S., Chen, X., Hu, Z., Rapid and sensitive determination of anthraquinones in Chinese herb using 1-butyl-3-methylimidazolium-based ionic liquid with β-cyclodextrin as modifier in capillary zone electrophoresis. J. Chromatogr. A 1059 (2004), 191–198, 10.1016/j.chroma.2004.09.090.
71. Räisänen, R., Björk, H., Hynninen, P.H., Two-dimensional TLC separation and mass spectrometric identification of anthraquinones isolated from the fungus Dermocybe sanguinea. Z. Fär Naturforschung C 55 (2000), 195–202.
72. Rahman, A., Bioactive Natural Products (Part G), Studies in Natural Products Chemistry. 2002, Elsevier Science.
73. Rafaëlly, L., Héron, S., Nowik, W., Tchapla, A., Optimisation of ESI-MS detection for the HPLC of anthraquinone dyes. Dyes Pigments 77 (2008), 191–203.
74. Reynolds, T., Aloes: The genus Aloe, Medicinal and Aromatic Plants − Industrial Profiles. 2004, CRC Press.
75. Rostagno, M.A., Prado, J.M., Natural product extraction: principles and applications, RSC green chemistry series. R. Soc. Chem., 2013.
76. Ruksilp, T., Sichaem, J., Khumkratok, S., Siripong, P., Tip-pyang, S., Anthraquinones and an iridoid glycoside from the roots of Morinda pandurifolia. Biochem. Syst. Ecol. 39 (2011), 888–892, 10.1016/j.bse.2011.07.003.
77. Sakulpanich, A., Gritsanapan, W., Extraction method for high content of anthraquinones from Cassia fistula pods. J. Health Res. 22 (2008), 167–172.
78. Samia, M., El-Sayyad, R.S., Phytochemical study of some Cassia species cultivated in Egypt. J. Afr. Biotechnol., 2006, 806–809.
79. Saxena, S., Raja, A., Natural dyes: sources, chemistry, application and sustainability issues. Roadmap to Sustainable Textiles and Clothing, 2014, Springer, 37–80.
80. Schneiderman, M.A., Sharma, A.K., Locke, D.C., Determination of anthraquinone in paper and wood using supercritical fluid extraction and high-performance liquid chromatography with electrochemical detection. J. Chromatogr. A 409 (1987), 343–353, 10.1016/S0021-9673(01)86811-4.
81. Schrader, K.K., Dayan, F.E., Allen, S.N., de Regt, M.Q., Tucker, C.S., Paul, J., Rex, N., 9,10-Anthraquinone reduces the photosynthetic efficiency of oscillatoria perornata and modifies cellular inclusions. Int. J. Plant Sci. 161 (2000), 265–270, 10.1086/314255.
82. Seigler, D.S., Plant Secondary Metabolism. 2012, Springer Science & Business Media.
83. Shamsipur, M., Fasihi, J., Khanchi, A., Yamini, Y., Valinezhad, A., Sharghi, H., Solubilities of some 9,10-anthraquinone derivatives in supercritical carbon dioxide: a cubic equation of state correlation. J. Supercrit. Fluids 47 (2008), 154–160, 10.1016/j.supflu.2008.07.002.
84. Shang, X., Yuan, Z., Determination of active components in Rhubarb and study of their hydrophobicity by micellar electrokinetic chromatography. Bioorg. Med. Chem. Lett. 13 (2003), 617–622, 10.1016/S0960-894X(02)01043-0.
85. Sheu, S.-J., Chen, H.-R., Determination of five major anthraquinoids in Chinese herbal preparations by micellar electrokinetic capillary electrophoresis. Anal. Chim. Acta 309 (1995), 361–367, 10.1016/0003-2670(95)00034-W.
86. Sharma, N., Kumar, R., Sinha, A.K., Reddy, P.B., Nayeem, S.M., Deep, S., Anthraquinone derivatives based natural dye from Rheum emodi as a probe for thermal stability of proteins: spectroscopic and chromatographic studies. J. Pharm. Biomed. Anal. 62 (2012), 96–104.
87. Singh, A., Herbal Drugs as Therapeutic Agents. 2014, CRC Press.
88. Singh, R., Isolation and synthesis of anthraquinones and related compounds of Rubia cordifolia. J. Serbian Chem. Soc. 70 (2005), 937–942.
89. Singh, N.P., Gupta, A.P., Sinha, A.K., Ahuja, P.S., High-performance thin layer chromatography method for quantitative determination of four major anthraquinone derivatives in Rheum emodi. J. Chromatogr. A 1077 (2005), 202–206, 10.1016/j.chroma.2005.03.130.
90. Siva, R., Mayes, S., Behera, S.K., Rajasekaran, C., Anthraquinones dye production using root cultures of Oldenlandia umbellata L. Ind. Crops Prod. 37 (2012), 415–419.
91. Smallwood, I., Handbook of Organic Solvent Properties. 2012, Elsevier Science.
92. Spencer, C.M., Wilde, M.I., Diacerein. Drugs 53 (1997), 98–106, 10.2165/00003495-199753010-00007.
93. Stodůlková, E., Man, P., Kolařík, M., Flieger, M., High-performance liquid chromatography?off line mass spectrometry analysis of anthraquinones produced by Geosmithia lavendula. J. Chromatogr. A 1217 (2010), 6296–6302.
94. Strotmann, H., Brendel, K., Boos, K.S., Schlimme, E., Energy transfer inhibition in photosynthesis by anthraquinone dyes. FEBS Lett. 145 (1982), 11–15, 10.1016/0014-5793(82)81196-4.
95. Ţebrencu, C.E., Creţu, R.M., Mitroi, G.R., Iacob, E., Ionescu, E., Phytochemical evaluation and HPTLC investigation of bark and extracts of Rhamnus Frangula Linn. Phytochem. Rev., 2015, 1–9.
96. Tala, M.F., Talontsi, F.M., Wabo, H.K., Lantovololona, J.E.R., Tane, P., Laatsch, H., Anthraquinones and triterpenoids from seeds of Vismia guineensis. Biochem. Syst. Ecol. 50 (2013), 310–312.
97. Terrill, J.B., Jacobs, E.S., Application of gas-liquid chromatography to the analysis of anthraquinone dyes and intermediates. J. Chromatogr. Sci. 8 (1970), 604–607.
98. Thakur, A., Hamrapurkar, P., Quantitative densitometric HPTLC analysis of purpurin in the parts of Rubia cordifolia and in pharmaceutical dosage forms. JPC-J. Planar Chromatogr. – Mod. TLC 22 (2009), 109–113.
99. Tian, K., Wang, Y., Chen, Y., Chen, X., Hu, Z., Application of 1-alkyl-3-methylimidazolium-based ionic liquids as background electrolyte in capillary zone electrophoresis for the simultaneous determination of five anthraquinones in Rhubarb. Talanta 72 (2007), 587–593, 10.1016/j.talanta.2006.11.027.
100. Tubaon, R.M.S., Rabanes, H., Haddad, P.R., Quirino, J.P., Capillary electrophoresis of natural products: 2011–2012. Electrophoresis 35 (2014), 190–204, 10.1002/elps.201300473.
101. Urbain, A., Marston, A., Queiroz, E.F., Ndjoko, K., Hostettmann, K., Xanthones from Gentiana campestris as new acetylcholinesterase inhibitors. Planta Med. 70 (2004), 1011–1014.
102. Vázquez, M.F.B., Comini, L.R., Milanesio, J.M., Montoya, S.C.N., Cabrera, J.L., Bottini, S., Martini, R.E., Pressurized hot water extraction of anthraquinones from Heterophyllaea pustulata Hook f (Rubiaceae). J. Supercrit. Fluids 101 (2015), 170–175, 10.1016/j.supflu.2015.02.029.
103. Van Eijk, G.W., Roeijmans, H.J., Separation and identification of naturally occurring anthraquinones by capillary gas chromatography and gas chromatography—mass spectrometry. J. Chromatogr. A 295 (1984), 497–502, 10.1016/S0021-9673(01)87653-6.
104. Wang, L., Li, D., Bao, C., You, J., Wang, Z., Shi, Y., Zhang, H., Ultrasonic extraction and separation of anthraquinones from Rheum palmatum L. Ultrason. Sonochem. 15 (2008), 738–746, 10.1016/j.ultsonch.2007.12.008.
105. Wang, N., Su, M., Liang, S., Sun, H., Investigation of six bioactive anthraquinones in slimming tea by accelerated solvent extraction and high performance capillary electrophoresis with diode-array detection. Food Chem. 199 (2016), 1–7, 10.1016/j.foodchem.2015.11.083.
106. Wei, Y., Zhang, T., Ito, Y., Preparative separation of rhein from Chinese traditional herb by repeated high-speed counter-current chromatography. J. Chromatogr. A 1017 (2003), 125–130.
107. Weng, W., Sheu, S., Separation of anthraquinones by capillary electrophoresis and high‐performance liquid chromatography. J. High Resolut. Chromatogr. 23 (2000), 143–148.
108. Whatley, H., Basic principles and modes of capillary electrophoresis. Clinical and Forensic Applications of Capillary Electrophoresis, 2001, Springer, 21–58.
109. Wolfender, J.-L., Marti, G., Thomas, A., Bertrand, S., 2015. Current approaches and challenges for the metabolite profiling of complex natural extracts. Ed. Choice IX 1382, 136–164. http://dx.doi.org/10.1016/j.chroma.2014.10.091.
110. Wube, A.A., Bucar, F., Asres, K., Gibbons, S., Rattray, L., Croft, S.L., Antimalarial compounds from Kniphofia foliosa roots. Phytother. Res. 19 (2005), 472–476.
111. Xie, Y., Liang, Y., Chen, H., Zhang, T., Ito, Y., Preparative isolation and purification of anthraquinones from Cassia seed by high-speed countercurrent chromatography. J. Liq. Chromatogr. Relat. Technol. 30 (2007), 1475–1488.
112. Yang, F., Zhang, T., Tian, G., Cao, H., Liu, Q., Ito, Y., Preparative isolation and purification of hydroxyanthraquinones from Rheum officinale Baill by high-speed counter-current chromatography using pH-modulated stepwise elution. J. Chromatogr. A 858 (1999), 103–107, 10.1016/S0021-9673(99)00827-4.
113. Ye, M., Han, J., Chen, H., Zheng, J., Guo, D., Analysis of phenolic compounds in rhubarbs using liquid chromatography coupled with electrospray ionization mass spectrometry. J. Am. Soc. Mass Spectrom. 18 (2007), 82–91.
114. Yen, G.-C., Duh, P.-D., Chuang, D.-Y., Antioxidant activity of anthraquinones and anthrone. Food Chem. 70 (2000), 437–441.
115. Yilmaz, E.E., Özvural, E.B., Vural, H., Extraction and identification of proanthocyanidins from grape seed (Vitis Vinifera) using supercritical carbon dioxide. J. Supercrit. Fluids 55 (2011), 924–928, 10.1016/j.supflu.2010.10.046.
116. Zengin, G., Locatelli, M., Ceylan, R., Aktumsek, A., Anthraquinone profile, antioxidant and enzyme inhibitory effect of root extracts of eight Asphodeline taxa from Turkey: can Asphodeline roots be considered as a new source of natural compounds?. J. Enzyme Inhib. Med. Chem., 2015, 1–6.
117. Zengin, G., Menghini, L., Malatesta, L., De Luca, E., Bellagamba, G., Uysal, S., Aktumsek, A., Locatelli, M., Comparative study of biological activities and multicomponent pattern of two wild Turkish species: Asphodeline anatolica and Potentilla speciosa. J. Enzyme Inhib. Med. Chem., 2016, 1–6.
118. Zhang, Y.Y., Li, Z.C., Zhu, J.K., Yang, Z.Y., Wang, Q.J., He, P.G., Fang, Y.Z., Simultaneous determination of flavonoids and anthraquinones in chrysanthemum by capillary electrophoresis with amperometry detection. Chin. Chem. Lett. 21 (2010), 1231–1234, 10.1016/j.cclet.2010.04.040.
119. Zhang, T.-Y., Pannell, L.K., Pu, Q.-L., Cai, D.-G., Ito, Y., Separation of hydroxyanthraquinone derivatives extracted from rheum with analytical high-speed counter-current chromatography. J. Chromatogr. A 442 (1988), 455–458.
120. Zhao, L.-C., Liang, J., Li, W., Cheng, K.-M., Xia, X., Deng, X., Yang, G.-L., The use of response surface methodology to optimize the ultrasound-assisted extraction of five anthraquinones from Rheum palmatum L. Molecules 16 (2011), 5928–5937.
121. Zhao, F., Zhao, S., Han, J.-T., Wang, Y.-F., Wang, Y.-N., Wang, C.-H., Antiviral anthraquinones from the roots of Knoxia valerianoides. Phytochem. Lett. 11 (2015), 57–60, 10.1016/j.phytol.2014.11.015.
122. Zhou, Y., Lv, H., Wang, W., Tu, P., Jiang, Y., Flavonoids and anthraquinones from murraya tetramera C.C. Huang (Rutaceae). Biochem. Syst. Ecol. 57 (2014), 78–80, 10.1016/j.bse.2014.07.016.
123. Zou, J., Xie, Z., Jiang, X., Chen, X., Yao, M., Determination of anthraquinones in different compatibility of Dahuang Huanglian Xiexin Decoction by HPLC. World Sci. Technol. 10 (2008), 61–64.
124. Zhu, L., Li, H., Liang, Y., Wang, X., Xie, H., Zhang, T., Ito, Y., Application of high-speed counter-current chromatography and preparative high-performance liquid chromatography mode for rapid isolation of anthraquinones from Morinda officinalis How. Sep. Purif. Technol. 70 (2009), 147–152, 10.1016/j.seppur.2009.09.009.
125. de Melo, M.M.R., Silvestre, A.J.D., Silva, C.M., Supercritical fluid extraction of vegetable matrices: applications, trends and future perspectives of a convincing green technology. J. Supercrit. Fluids 92 (2014), 115–176, 10.1016/j.supflu.2014.04.007.
126. van Eijk, G.W., Roeymans, H.J., Gas-liquid chromatography of trimethylsilyl ethers of naturally occurring anthraquinones. J. Chromatogr. A 124 (1976), 66–68, 10.1016/S0021-9673(00)87839-5.
127. Zhu, L., Yu, S., Zeng, X., Fu, X., Zhao, M., Preparative separation and purification of five anthraquinones from Cassia tora L: by high-speed counter-current chromatography. Sep. Purif. Technol 63 (2008), 665–669.