Planta Med 2015; 81(17): 1609-1613
DOI: 10.1055/s-0035-1546116
Original Papers
Georg Thieme Verlag KG Stuttgart · New York

Gradient x Isocratic Elution CCC on the Isolation of Verbascoside and Other Phenylethanoids: Influence of the Complexity of the Matrix

Gilda Guimarães Leitão
1   Universidade Federal do Rio de Janeiro, Instituto de Pesquisas de Produtos Naturais, Rio de Janeiro, Brazil
,
Shaft Correa Pinto
2   Universidade Federal do Rio de Janeiro, Curso de Farmácia/Campus-Macaé, Rio de Janeiro, Brazil
3   Universidade Federal do Rio de Janeiro, Departamento de Produtos Naturais e Alimentos, Faculdade de Farmácia, Rio de Janeiro, Brazil
,
Danilo Ribeiro de Oliveira
3   Universidade Federal do Rio de Janeiro, Departamento de Produtos Naturais e Alimentos, Faculdade de Farmácia, Rio de Janeiro, Brazil
,
Patrícia Timoteo
3   Universidade Federal do Rio de Janeiro, Departamento de Produtos Naturais e Alimentos, Faculdade de Farmácia, Rio de Janeiro, Brazil
,
Michelle Guedes Guimarães
3   Universidade Federal do Rio de Janeiro, Departamento de Produtos Naturais e Alimentos, Faculdade de Farmácia, Rio de Janeiro, Brazil
,
Wilmer H. Perera Cordova
3   Universidade Federal do Rio de Janeiro, Departamento de Produtos Naturais e Alimentos, Faculdade de Farmácia, Rio de Janeiro, Brazil
,
Suzana Guimarães Leitão
3   Universidade Federal do Rio de Janeiro, Departamento de Produtos Naturais e Alimentos, Faculdade de Farmácia, Rio de Janeiro, Brazil
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Weitere Informationen

Publikationsverlauf

received 03. Oktober 2014
revised 03. März 2015

accepted 20. April 2015

Publikationsdatum:
01. Juli 2015 (online)

Abstract

Verbascoside is a phenylethanoid glycoside widely distributed in nature, especially among the order Lamiales, occurring in numerous plants that are constituents of folk medicine preparations. This natural compound, previously isolated by our group from the ethyl acetate extract of Lantana trifolia using the gradient approach in countercurrent chromatography, was now isolated from the butanol extract of the same plant and from Lippia alba f. intermedia (Verbenaceae) using countercurrent chromatography in either gradient or isocratic elution modes. The ethyl acetate extract of L. alba, rich in phenylethanoids and flavonoids, was fractionated using countercurrent chromatography in the step-gradient elution approach. The four-step solvent system was composed of n-hexane-ethyl acetate-n-butanol-water (4 : 10 : X : 10), where X = 1 (solvent system A), 3 (solvent system B), 5 (solvent system C), and 7 (solvent system D), and allowed for the isolation of verbascoside along with other phenylethanoids and flavonoids from both plants. Verbascoside and 2′-O-β-apiosylverbascoside were further isolated from the n-butanol extract of L. trifolia using the solvent system ethyl acetate-n-butanol-water 10 : 2 : 10 on an isocratic run. The difference in the complexity of the two plant extracts demanded different purification steps, which included a second high-speed countercurrent chromatography purification using the isocratic elution mode.

Supporting Information

 
  • References

  • 1 Alipieva K, Korkina L, Orhan IL, Georgiev MI. Verbascoside–a review of its occurrence, (bio)synthesis and pharmacological significance. Biotechnol Adv 2014; 32: 1065-1076
  • 2 Funes L, Laporta O, Cerdán-Calero M, Micol V. Effects of verbascoside, a phenylpropanoid glycoside from lemon verbena, on phospholipid model membranes. Chem Phys Lipids 2010; 163: 190-199
  • 3 Funari CS, Gulo FP, Napolitano A, Carneiro RL, Mendes-Giannini MJS, Fusco-Almeida AM, Silva DHS. Chemical and antifungal investigation of six Lippia species (Vrebenaceae) from Brazil. Food Chem 2012; 135: 2086-2094
  • 4 Filho AG, Morel AF, Adolpho L, Ilha V, Giralt E, Tarrago T, Dalcol II. Inhibitory effect of verbascoside isolated from Budleja brasiliensis Jack ex Spreng on prolyl oligopeptodase activity. Phytother Res 2012; 26: 1472-1475
  • 5 Troncoso NS. Los Géneros de Verbenáceas de Sudamérica extratropical. Darwiniana 1974; 18: 295-412
  • 6 Ghisalberti EL. Lantana camara Linn (Rev.). Fitoterapia 2000; 71: 467-485
  • 7 Pascual ME, Slowing K, Carretero E, Mata DS, Villar A. Lippia: traditional uses, chemistry and pharmacology: a review. J Ethnopharmacol 2001; 76: 201-214
  • 8 Oliveira DR, Leitão GG, Santos SS, Bizzo HR, Lopes D, Alviano CS, Alviano DS, Leitão SG. Ethnopharmacological study of two Lippia species from Oriximiná, Brazil. J Ethnopharmacol 2006; 108: 103-108
  • 9 Julião LS, Leitão SG, Lotti C, Picinelli AL, Rastrelli L, Fernandes PD, Noël F, Thibaudt JPB, Leitão GG. Flavones and phenylpropanoids from a sedative extract of Lantana trifolia L. Phytochemistry 2010; 71: 294-300
  • 10 Hostettmann K, Hosttemann-Kaldas M, Sticher O. Application of droplet counter-current chromatography to the isolation of natural products. J Chromatogr 1979; 186: 529-534
  • 11 Cooper R, Solomon PH, Kubo I, Nakanishi K, Shoolery JN, Occolowitz JL. Myricoside, an African armyworm antifeedant: separation by droplet countercurrent chromatography. J Am Chem Soc 1980; 102: 7953-7955
  • 12 Hostettmann K, Hostettmann M, Marston A. Isolation of natural products by droplet counter-current chromatography and related methods. Nat Prod Rep 1984; 1: 471-481
  • 13 Li L, Wang J, Gui Y, Zong X, Liu C. Isolation and purification of phenylethanoid glycosides from plant extract of Cistanche deserticola by high performance centrifugal partition chromatography. Shizhen Guoyi Guoyao 2011; 22: 1549-1551
  • 14 Li L, Tsao R, Liu Z, Liu S, Yang R, Young JC, Zhu H, Deng Z, Xie M, Fu Z. Isolation and purification of acteoside and isoacteoside from Plantago psyllium L. by high-speed counter-current chromatography. J Chromatogr A 2005; 1063: 161-169
  • 15 Lei L, Yang F, Zhang T, Tu P, Wu L, Chen F, Ito Y. Preparative isolation and purification of phenylethanoid glycosides from the extract of faeces of beagle dogs by high-speed countercurrent chromatography. J Liq Chrom Rel Technol 2001; 24: 2187-2195
  • 16 Viron C, Lhermite S, André P, Lafosse M. Isolation of phenylpropanoid glycosides from Orobanche rapum by high speed countercurrent chromatography. Phytochem Anal 1998; 9: 39-43
  • 17 Lei L, Yang F, Zhang T, Tu P, Wu L, Ito Y. Preparative isolation and purification of acteoside and 2′-acetylacteoside from Cistanches salsa (C.A. Mey.) G. Beck by highspeed counter-current chromatography. J Chromatogr A 2001; 912: 181-185
  • 18 Leitão GG, de Souza PA, Moraes AA, Brown L. Step-gradient CCC separation of phenylpropanoid and iridoid glycosides from roots of Stachytarpheta cayennensis (Rich.) Vahl. J Liq Chrom Rel Technol 2005; 28: 2053-2060
  • 19 Han L, Ji L, Boakye-Yiadom M, Li W, Song X, Gao X. Preparative isolation and purification of four compounds from Cistanche deserticola Y.C. Ma by high-speed counter-current chromatography. Molecules 2012; 17: 8276-8284
  • 20 Xie C, Xu X, Liu Q, Xie Z, Yang M, Huang J, Yang D. Isolation and purification of echinacoside and acteoside from Cistanche tubulosa (Schrenk) Wight by high-speed counter-current chromatography. J Liq Chrom Rel Technol 2012; 35: 2602-2609
  • 21 Duan WJ, Zheng ZJ, Geng YL, Liu JH, Wang X. Preparative isolation and purification of C6–C2 natural alcohol and benzyl ethanol from Forsythia suspensa by high-speed countercurrent chromatography. Acta Chromatogr 2011; 23: 499-507
  • 22 Li L, Rong T, Yang R, Liu C, Young JC, Zhu H. Isolation and purification of phenylethanoid glycosides from Cistanche deserticola by high-speed counter-current chromatography. Food Chem 2008; 108: 702-710
  • 23 Li L, Tsao R, Liu Z, Liu S, Yang R, Young JC, Zhu H, Deng Z, Xie M, Fu Z. Isolation and purification of acteoside and isoacteoside from Plantago psyllium L. by high-speed counter-current chromatography. J Chromatogr A 2005; 1063: 161-169
  • 24 Mei LH, Kyu KJ, Man JJ, Bi CC, Sung LS. Analysis of the inhibitory activity of Abeliophyllum distichum leaf constituents against aldose reductase by using high-speed counter current chromatography. Arch Pharm Res 2013; 36: 1104-1112
  • 25 Jun X, Feng T, Jing Z, Caibo Y, Qi L. Separation, purification and quantification of verbascoside from Penstemon barbatus (Cav.) Roth. Food Chem 2012; 135: 2536-2541
  • 26 Berthod A, Brown L, Leitão GG, Leitão SG. Solvent systems in centrifugal partition chromatography. In: Barceló D, Berthod A, editors Countercurrent chromatography: the support free liquid stationary phase (Comprehensive analytical chemistry), Vol. XXXVIII. NewYork: Elsevier; 2002: 37
  • 27 Wu S, Wu D, Liang J, Berthod A. Modelling gradient elution in countercurrent chromatography: efficient separation of tanshinones from Salvia miltiorriza Bunge. J Sep Sci 2012; 35: 964-976
  • 28 Foucault AP. In. Foucault AP, editor. Centrifugal partition chromatography. Chromatographic science series, Vol. 68. New York: Marcel Dekker, Inc.; 1995: 90