Download PDF
CC BY-NC-ND 4.0 · Planta Medica International Open 2021; 8(01): e34-e42
DOI: 10.1055/a-1375-6456
Original Article

Extraction and Fractionation Effects on Antiplasmodial Activity and Phytochemical Composition of Palicourea hoffmannseggiana

Leticia Hiromi Ohashi
1   Programa de Pós-graduação em Ciências Farmacêuticas, Universidade Federal do Pará, Guamá, Belém, PA, Brazil
2   Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Pampulha, Belo Horizonte, MG, Brazil
,
Douglas Costa Gontijo
2   Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Pampulha, Belo Horizonte, MG, Brazil
,
Maria Fernanda Alves do Nascimento
2   Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Pampulha, Belo Horizonte, MG, Brazil
,
Luciano Ferreira Margalho
3   Instituto Federal do Pará, Icuí-Guajará, Ananindeua, PA, Brazil
,
Geraldo Célio Brandão
4   Escola de Farmácia, Universidade Federal de Ouro Preto, Ouro Preto, MG, Brazil
,
Alaíde Braga de Oliveira
1   Programa de Pós-graduação em Ciências Farmacêuticas, Universidade Federal do Pará, Guamá, Belém, PA, Brazil
2   Departamento de Produtos Farmacêuticos, Faculdade de Farmácia, Universidade Federal de Minas Gerais, Pampulha, Belo Horizonte, MG, Brazil
› Author Affiliations
› Further Information
   Permissions and Reprints

Abstract

The present study on Palicourea hoffmannseggiana, which was collected at Marapanim, state of Pará, Brazil, comprises the preparation of different stem and leaf extracts and fractions. Ethanol, hydroethanol, and water extracts were prepared by several methods and evaluated for in vitro activity against resistant Plasmodium falciparum (W2 strain), disclosing a low parasite growth inhibition effect (< 50%). Dereplication by UPLC-DAD-ESI−MS of the leaf ethanol extract showed the presence of two known alkaloids, lyalosidic and strictosidinic acids, along with a sinapoyl ester of lyalosidic acid, with m/z 719.33 [M+H]+, which is possibly a new monoterpene indole alkaloid representative. Sequential liquid-liquid acid-base alkaloid separations from the leaf ethanol extract as well as directly from leaf powder afforded fractions of increased parasite growth inhibition, reaching up to 92.5±0.7%. The most bioactive fractions were shown to contain the β-carboline alkaloids harmane and 4-methyl-β-carboline, along with N-methyl-tryptamine and N-acetyl-tryptamine, while monoterpene indole alkaloids were detected in inactive fractions of these processes. The present results demonstrate that these preliminary fractionation methods can lead to significantly active fractions supporting an adequate scale-up to carrying out the isolation of anti-plasmodial compounds.

Key words

Palicourea hoffmannseggiana - Rubiaceae - monoterpene indole alkaloids - β-carboline alkaloids - Plasmodium falciparum

Supplementary Material



Publication History

Received: 18 October 2020
Received: 19 January 2021

Accepted: 25 January 2021

Article published online:
19 April 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/).

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References

  • 1 Flora do Brasil. Available at http://floradobrasil.jbrj.gov.br/reflora/floradobrasil/FB609534. Accessed December 1, 2020
    PubMed
  • 2 Borhidi A. Transfer of the Mexican species of Psychotria subgen. Heteropsychotria to Palicourea based on morphological and molecular evidences. Acta Bot Hung 2011; 53: 245-250
    CrossrefPubMedGoogle Scholar
  • 3 Tropicos. Available at: http://www.tropicos.org/Name/100408987 Accessed December 1, 2020
    PubMed
  • 4 Delprete PG, Jardim JG. Systematics, taxonomy and floristics of Brazilian Rubiaceae: an overview about the current status and future challenges. Rodriguésia 2012; 63: 121-128
    CrossrefPubMedGoogle Scholar
  • 5 Martins D, Nunez CV. Secondary metabolites from Rubiaceae species. Molecules 2015; 20: 13422-13495
    CrossrefPubMedGoogle Scholar
  • 6 Berger A, Tanuhadi E, Brecker L, Schinnerl J, Valant-Vetschera K. Chemodiversity of tryptamine-derived alkaloids in six Costa Rican Palicourea species (Rubiaceae – Palicoureeae). Phytochemistry 2017; 143: 124-131
    CrossrefPubMedGoogle Scholar
  • 7 Calixto N, Pinto M, Ramalho S, Burguer M, Bobey A, Zoung M, Bolzani V, Pinto A. The genus Psychotria: phytochemistry, chemotaxonomy, ethnopharmacology and biological properties. J Braz Chem Soc 2016; 27: 1355-1378
    PubMedGoogle Scholar
  • 8 Ohashi LH, Oliveira AB. Palicourea hoffmannseggiana (Schult.) Borhidi (Rubiaceae): a revision on botanical taxonomy, phytochemistry, biological activities and antimalarial activity. Elec J Collect Health 2020; 43: e3027
    PubMedGoogle Scholar
  • 9 World Health Organization. Available at: https://www.who.int/news-room/feature-stories/detail/world-malaria-report-2019. Accessed May 29, 2020
    PubMed
  • 10 World Health Organization. Available at: https://www.who.int/publications/i/item/9789240012813. Accessed December 23, 2020
    PubMed
  • 11 Maji AK. Drug susceptibility testing methods of antimalarial agents. Trop Parasitol 2018; 8: 70-76
    CrossrefPubMedGoogle Scholar
  • 12 Baniecki ML, Wirth DF, Clardy J. High-Throughput Plasmodium falciparum Growth Assay for Malaria Drug Discovery. Antimicrob Agents Chemother 2007; 51: 716-723
    CrossrefPubMedGoogle Scholar
  • 13 Fidock DA, Rosenthal PJ, Croft SL, Brun R, Nwaka S. Antimalarial drug discovery: efficacy models for compound screening. Nat Rev Drug Discov 2004; 3: 509-520
    CrossrefPubMedGoogle Scholar
  • 14 Merk D, Friedrich L, Grisoni F, Schneider G. De Novo Design of Bioactive Small Molecules by Artificial Intelligence. Mol Inform 2018; 37: 1700153
    CrossrefPubMedGoogle Scholar
  • 15 Dirar AI, Alsaadi DHM, Wada M, Mohamed MA, Watanabe T, Devkota PH. Effects of extraction solvents on total phenolic and flavonoid contents and biological activities of extracts from Sudanese medicinal plants. South African J Bot 2019; 120: 261-267
    CrossrefPubMedGoogle Scholar
  • 16 Belwal T, Ezzat SM, Rastrelli L, Bhatt ID, Daglia M, Baldi A, Devkota HP, Orhan IE, Patra JK, Das G. A critical analysis of extraction techniques used for botanicals: Trends, priorities, industrial uses and optimization strategies. Trends Anal Chem 2018; 100: 82-102
    CrossrefPubMedGoogle Scholar
  • 17 Gontijo DC, Leite JPV, Nascimento MFA, Brandão GC, Oliveira AB. Bioprospection for antiplasmodial activity, and identification of bioactive metabolites of native plants species from the Mata Atlântica biome, Brazil. Nat Prod Res, advance online publication 24 June 2019; DOI: 10.1080/14786419.2019.1633645.
    CrossrefPubMedGoogle Scholar
  • 18 Berger A, Kostyan MK, Klose SI, Gastegger M, Lorbeer E, Brecker L, Schinnerl J. Loganin and secologanin derived tryptamine-iridoid alkaloids from Palicourea crocea and Palicourea padifolia (Rubiaceae). Phytochemistry 2015; 116: 162-169
    CrossrefPubMedGoogle Scholar
  • 19 Klein-Junior L, Cretton S, Allard P, Genta-Jouve G, Passos C, Salton J, Bertelli P, Pupier M, Jeannerat D, Vander Y, Gasper A, Wolfender J, Christen P, Henriques A. Targeted isolation of monoterpene indole alkaloids from Palicourea sessilis . J Nat Prod 2017; 80: 3032-3037
    CrossrefPubMedGoogle Scholar
  • 20 Valverde J, Tamayo G, Hesse M. β-Carboline monoterpenoid glucosides from Palicourea adusta . Phytochemistry 1999; 52: 1485-1489
    CrossrefPubMedGoogle Scholar
  • 21 Sangster AW, Stuart KL. Ultraviolet spectra of alkaloids. Chem Rev 1964; 65: 69-130
    CrossrefPubMedGoogle Scholar
  • 22 Wang YH, Samoylenko V, Tekwani BL, Khan IA, Miller LS, Chaurasiya ND, Rahman MM, Tripathi L, Khan SI, Joshi VC, Wigger FT. Muhammad I. Composition, standardization and chemical profiling of Banisteriopsis caapi, a plant for the treatment of neurodegenerative disorders relevant to Parkinson’s disease. J Ethnopharmacol 2010; 128: 662-671
    CrossrefPubMedGoogle Scholar
  • 23 Shi Y, Wang R, Zhu X, Xu D, Liu W, Feng F. A self-feedback network based on liquid chromatography-quadrupole-time of flight mass spectrometry for system identification of β-carboline alkaloids in Picrasma quassioides. . Sci Rep 2017; 7: 713841
    PubMedGoogle Scholar
  • 24 Chen BH, Liu JT, Chen WX, Chen HM, Lin CH. A general approach to the screening and confirmation of tryptamines and phenethylamines by mass spectral fragmentation. Talanta 2008; 74: 512-517
    CrossrefPubMedGoogle Scholar
  • 25 Ouyang Y, Liang Y, Li S, Luo X, Zhang L, Tang Z, Wang Q, Xu X. Interpretation of the characteristic fragmentation mechanism through determining the initial ionization site by natural spin density: A study on the derivatives of tryptophan and tryptamine. Int J Mass Spectrom 2009; 286: 112-121
    CrossrefPubMedGoogle Scholar
  • 26 Li S, Liu W, Teng L, Cheng X, Wang Z, Wang C. Metabolites identification of harmane in vitro/in vivo in rats by ultra-performance liquid chromatography combined with electrospray ionization quadrupole time-of-flight tandem mass spectrometry. J Pharm Biomed Anal 2014; 91: 53-62
    CrossrefPubMedGoogle Scholar
  • 27 Astulla A, Zaima K, Matsuno Y, Hirasawa Y, Ekasari W, Widyawaruyanti A, Zaini NC, Morita H. Alkaloids from the seeds of Peganum harmala showing antiplasmodial and vasorelaxant activities. J Nat Med 2008; 62: 470-472
    CrossrefPubMedGoogle Scholar
  • 28 Ancolio C, Azas N, Mahiou V, Ollivier E, Di Giorgio C, Keita A, Timon-David P, Balansard G. Antimalarial activity of extracts and alkaloids isolated from six plants used in traditional medicine in Mali and Sao Tome. Phytother Res 2002; 16: 646-649
    CrossrefPubMedGoogle Scholar
  • 29 Fiot J, Sanon S, Azas N, Mahiou V, Jansen O, Angenot L, Ollivier E. Phytochemical and pharmacological study of roots and leaves of Guiera senegalensis J.F. Gmel (Combretaceae). J Ethnopharmacol 2006; 106: 173-178
    CrossrefPubMedGoogle Scholar
  • 30 Ashok P, Ganguly S, Murugesan S. Review on in-vitro anti-malarial activity of natural β-carboline alkaloids. Mini-Rev Med Chem 2013; 13: 1778-1791
    CrossrefPubMedGoogle Scholar
  • 31 Samulski GB, Gontijo DC, Moreira NC, Brandão GC, Oliveira AB. Dereplication of Palicourea sessilis ethanol extracts by UPLC-DAD-ESI-MS/MS discloses the presence of hydroxycinnamic acid amides and the absence of monoterpene indole alkaloids. Biochem Syst Ecol 2020; 92: 104114
    CrossrefPubMedGoogle Scholar
  • 32 Wei X, Shen H, Wang L, Meng Q, Liu W. Analyses of Total Alkaloid Extract of Corydalis yanhusuo by Comprehensive RP × RP Liquid Chromatography with pH Difference. J Anal Methods Chem 2016; 2016: 9752735
    PubMedGoogle Scholar
  • 33 Gontijo DC, Brandão GC, Gontijo PC, Oliveira AB, Diaz MAN, Fietto LG, Leite JPV. Identification of phenolics compounds and biologically related activities from Ocotea odorifera aqueous extract leaves. Food Chem 2017; 230: 618-626
    CrossrefPubMedGoogle Scholar
  • 34 Gontijo DC, Brandão GC, Nascimento MFA, Oliveira AB. Antiplasmodial activity and cytotoxicity, isolation of active alkaloids, and dereplication of Xylopia sericea leaves ethanol extract by UPLC-DAD-ESI-MS/MS. J Pharm Pharmacol 2019; 71: 260-269
    CrossrefPubMedGoogle Scholar
  • 35 Systat Software
    PubMed