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Alternative extraction of alkaloid anticarcinogens from Brazilian "vinca rosea" using Ion exchange chromatography

Abstract

Extracts in ethanol and ethanol-ammonia of dried leaves from Catharanthus roseus, gathered at Rio de Janeiro state, were adsorbed in a strongly acidic cation exchange resin with sulfonic acid group, using the finite bath method, resulting in an alkaloid retained fraction and an acidic and neutral unretained fraction. High Performance Liquid Chromatography showed the isolation of the alkaloid fraction to be highly selective and with good performance, with an absence of alkaloids in the unretained fraction, while the retained fraction presented 1,54-6,35 mg/g of vindoline and 0,12-0,91 mg/g of vinblastine, common for an alkaloid-rich concentrate, usually obtained by classic extraction with several steps using solvents.


Alternative extraction of alkaloid anticarcinogens from Brazilian "vinca rosea" using Ion exchange chromatography

Sérgio Freire de CarvalhaesI, * * sfcarv@iq.ufrj.br ; Daniela Lucena CostaII; José Luiz MazzeiIII; Luiz Eduardo Martins TaddeiIII; Luiz Antonio d'AvilaIII

IDepartamento de Química Inorgânica, Instituto de Química, Centro de Tecnologia, Universidade Federal do Rio de Janeiro, 21949-900, Rio de Janeiro, RJ

IIFaculdade de Farmácia, Centro de Ciências da Saúde, Universidade Federal do Rio de Janeiro, Rio de Janeiro, RJ

IIIDepartamento de Processos Orgânicos, Escola de Química, Centro de Tecnologia, Universidade Federal do Rio de Janeiro, 21949-900, Rio de Janeiro, RJ, Brazil

ABSTRACT

Extracts in ethanol and ethanol-ammonia of dried leaves from Catharanthus roseus, gathered at Rio de Janeiro state, were adsorbed in a strongly acidic cation exchange resin with sulfonic acid group, using the finite bath method, resulting in an alkaloid retained fraction and an acidic and neutral unretained fraction. High Performance Liquid Chromatography showed the isolation of the alkaloid fraction to be highly selective and with good performance, with an absence of alkaloids in the unretained fraction, while the retained fraction presented 1,54-6,35 mg/g of vindoline and 0,12-0,91 mg/g of vinblastine, common for an alkaloid-rich concentrate, usually obtained by classic extraction with several steps using solvents.

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Acknowledgments

The authors gratefully acknowledge the support received from Fundação Universitária José Bonifácio (FUJB/UFRJ) (Processo 8012-5), Conselho Nacional para o Desenvolvimento Científico e Tecnológico (CNPq), Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES), and Bayer S.A.

References

1 Cechinel VF, Yunes RA. Estratégias para obtenção de compostos farmacologicamente ativos a partir de plantas medicinais. Conceito sobre modificação estrutural para otimização da atividade. Química Nova. 1998; 21(1): 99-105

2 Zief M Kiser R. An overview of Solid Phase Extraction for sample preparation. American Laboratory. 1990; 70-83

3 Green JB, Hoff RJ, Woodward PW, Stevens LL. Separation of liquid fossil fuels into acid, base and neutral concentrates. An improved nonaqueous ion exchange method. Fuel 1984; 63:1290-1301

4 Soares KCC, Saraiva E, Taddei LEM, Carvalhaes, SF. Caracterização da capacidade de fixação e rendimento de recuperação de bases orgânicas em resinas catiônicas macroporosas com aplicação em Peschiera affinis. 23º Reunião da Sociedade Brasileira de Química (Annual Meeting of the Brazilian Society of Chemistry). 2000 5 Potier P. Rhône-Poulenc lecture. Search and Discovery of New Antitumor Compounds. Chemical Society Reviews. 1992; 21:113-119

6 Huhtikangas A, Pennanen S, Lousnamaa M. Process for the preparation of dimeric Catharanthus alkaloids. WO 89/12056 (1989), FI 89/00104 (1989), Appl. FI 882755 (1988), Class. Int. C07D 519/04

7 d'Avila LA, Mazzei JL, Carvalhaes GK, Martins HM, Anastácio CS, Carvalhaes SF, Furtado EG. Extração alternativa de alcalóides anti-cancerígenos da Vinca Rosa Brasileira. XV Simpósio de Plantas Medicinais do Brasil (Symposium on Medicinal Plants of Brazil). 1998

8 Mazzei JL, Martins HM, Carvalhaes GK. Análise de alcalóides da Vinca brasileira por CLAE. XXXV Congresso Brasileiro de Química (Brazilian Congress of Chemistry). 1995

9 Atta-ur-Rahman, Bashir M. A rapid procedure for the isolation of catharanthine, vindoline and vinblastine. Journal of Medicinal Plant. 1983; 47:246-256

10 Gunasekera SP. Method of isolation vinblastine. WO 88 03135 (1998), Appl US 922514 (1996), Class. Int. C07D 519/04

11 Naaranlahti T, Nordström M, Huhtikangas A. Determination of Catharanthus alkaloids by reversed-phase highperformance liquid chromatography. Journal of Chromatography. 1987; 410(2):488-493

  • 1 Cechinel VF, Yunes RA. Estratégias para obtençăo de compostos farmacologicamente ativos a partir de plantas medicinais. Conceito sobre modificaçăo estrutural para otimizaçăo da atividade. Química Nova. 1998; 21(1): 99-105
  • 2 Zief M Kiser R. An overview of Solid Phase Extraction for sample preparation. American Laboratory. 1990; 70-83
  • 3 Green JB, Hoff RJ, Woodward PW, Stevens LL. Separation of liquid fossil fuels into acid, base and neutral concentrates. An improved nonaqueous ion exchange method. Fuel 1984; 63:1290-1301
  • 4 Soares KCC, Saraiva E, Taddei LEM, Carvalhaes, SF. Caracterizaçăo da capacidade de fixaçăo e rendimento de recuperaçăo de bases orgânicas em resinas catiônicas macroporosas com aplicaçăo em Peschiera affinis 23º Reuniăo da Sociedade Brasileira de Química (Annual Meeting of the Brazilian Society of Chemistry). 2000 5 Potier P.
  • Rhône-Poulenc lecture. Search and Discovery of New Antitumor Compounds. Chemical Society Reviews. 1992; 21:113-119
  • 6 Huhtikangas A, Pennanen S, Lousnamaa M. Process for the preparation of dimeric Catharanthus alkaloids. WO 89/12056 (1989), FI 89/00104 (1989), Appl. FI 882755 (1988), Class. Int. C07D 519/04
  • 7 d'Avila LA, Mazzei JL, Carvalhaes GK, Martins HM, Anastácio CS, Carvalhaes SF, Furtado EG. Extraçăo alternativa de alcalóides anti-cancerígenos da Vinca Rosa Brasileira. XV Simpósio de Plantas Medicinais do Brasil (Symposium on Medicinal Plants of Brazil). 1998
  • 8 Mazzei JL, Martins HM, Carvalhaes GK. Análise de alcalóides da Vinca brasileira por CLAE. XXXV Congresso Brasileiro de Química (Brazilian Congress of Chemistry). 1995
  • 9 Atta-ur-Rahman, Bashir M. A rapid procedure for the isolation of catharanthine, vindoline and vinblastine. Journal of Medicinal Plant. 1983; 47:246-256
  • 10 Gunasekera SP. Method of isolation vinblastine. WO 88 03135 (1998), Appl US 922514 (1996), Class. Int. C07D 519/04
  • 11 Naaranlahti T, Nordström M, Huhtikangas A. Determination of Catharanthus alkaloids by reversed-phase highperformance liquid chromatography. Journal of Chromatography. 1987; 410(2):488-493
  • *
  • Publication Dates

    • Publication in this collection
      05 Oct 2009
    • Date of issue
      2002
    Sociedade Brasileira de Farmacognosia Universidade Federal do Paraná, Laboratório de Farmacognosia, Rua Pref. Lothario Meissner, 632 - Jd. Botânico, 80210-170, Curitiba, PR, Brasil, Tel/FAX (41) 3360-4062 - Curitiba - PR - Brazil
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