Estudo químico e avaliação da atividade antimalárica dos galhos de Piranhea trifoliata

Laila da Silva Pedroza; Marcos Gabriel Maciel Salazar; Maria Izabel Correia Osorio; Maria Tereza Fachin-Espinar; Renata Cristina de Paula; Maria Fernanda Alves de  Nascimento; Alaide Braga de Oliveira; Cecilia Veronica Nunez

doi:10.32712/2446-4775.2020.905

Chemical study and antimalarial activity evaluation of branches of Piranhea trifoliata

Vol. 14 No. 4 (2020)
476-491
15/11/2019
18/12/2020
https://doi.org/10.32712/2446-4775.2020.905

Laila da Silva Pedroza
Marcos Gabriel Maciel Salazar
Maria Izabel Correia Osorio
Maria Tereza Fachin-Espinar
Renata Cristina de Paula
Maria Fernanda Alves de Nascimento
Alaide Braga de Oliveira
Cecilia Veronica Nunez

National Institute of Amazonian Research (INPA), Coordination of Technology and Innovation, Laboratory of Bioprospecting and Biotechnology. Avenida André Araújo, 2936. Petrópolis, CEP 69067-375, Manaus, AM, Brazil.

holds a degree in Chemistry from Universidade Mackenzie (1993), a master's degree in Organic Chemistry (Natural Products) from the University of São Paulo (1996), a PhD in Organic Chemistry (Natural Products) from the University of São Paulo (2000), post-doctorate in Chemistry Organic (Natural Products) from the University of São Paulo - São Carlos (2000-2001) and post-doctorate in Pharmacognosy from the Université de Lille-2, Droit et Santé, France (2009-2010). Currently, he is a Senior Technologist at the National Institute of Research in the Amazon and a permanent professor / advisor of the Postgraduate Programs in Biotechnology-UFAM / INPA, Biotechnology-UEA / INPA and Botany-INPA and collaborating professor / advisor of the Postgraduate Program in Chemistry-UFAM / INPA. She has a level 2 productivity scholarship since 2014. She is the editor of Fitos and Vittalle magazines. He is a referee of Acta Amazonica, Química Nova, Revista Brasileira de Farmacognosia, Revista de Ciências Farmacêuticas Básicas e Aplicadas, International Research Journal of Biotechnology and Journal of Agricultural and Food Chemistry, among others. He has experience in the areas of Plant Biotechnology and Chemistry of Natural Products, acting mainly on the following topics: bioprospecting of plants and endophytic microorganisms, plant biotechnology (obtaining calluses / plant cell culture / cell suspensions), biomonitored fractionation, antioxidant activity , antimicrobial activity, cytotoxic activity, chromatographic separation methodology, identification / structural elucidation of molecules by NMR, analysis of mixtures by NMR and photoionization of natural products. He is a member of the Interdisciplinary Committee for the Evaluation of Books and Academic and Professional Graduate Programs of the Coordination for the Improvement of Higher Education Personnel - CAPES.

Keywords

Abstract

The objective of this work was to carry out the chemical study of Piranhea trifoliata (Picrodendraceae) branches and to evaluate their antimalarial potential. Two collections were performed in the State of Pará. The material was dried, ground and extracted with dichloromethane (DCM), methanol (MeOH) and water (H₂O). The DCM and MeOH extracts were subjected to comparative thin layer chromatography (TLC) analysis and showed characteristics mainly of terpenes. From the phytochemical study of the second collection DCM extract, it was isolated: friedelan-3-one and the second collection MeOH extract was isolated: the squalene triterpene, and the mixture of the stigmasterol and β-sitosterol steroids. Regarding antimalarial activity, MeOH extracts and phases were evaluated in vitro against Plasmodium falciparum, and MeOH extracts from the 1st and 2nd collections were considered active (IC₅₀ = 13.7 µg/mL; IC₅₀ = 5.8 µg/mL, respectively). This work contributed to the biological and chemical knowledge of the species Piranhea trifoliata and Picrodendraceae family, this being the first report of biological activities for the species under study.

References

Valdés AF, Martínez JM, Lizama RS, Gaitén YG, Rodríguez DA. Payrol JA. In vitro antimalarial activity and cytotoxicity of some selected cuban medicinal plants. Rev Inst Med Trop São Paulo. 2010; 52(4): 197-201. ISSN 1678-9946. [CrossRef].
Lenta BN, Ngouela S, Boyom FF, Tantangmo F, Tchouya GRF, Tsamo E et al. Anti-plasmodial Activity of Some Constituents of the Root Bark of Harungana madagascariensis Lam. (Hypericaceae). Chem Pharmac Bul. 2007; 55(3): 464-467. ISSN 1347-5223. [CrossRef] [PubMed].
Hu YQ, Gao C, Zhang S, Xu L, Xu Z, Feng LS et al. Quinoline hybrids and their antiplasmodial and antimalarial activities. Eur J Med Chem. 2017; 20(139): 22-47. ISSN 0223-5234. [CrossRef] [PubMed].
Aditya NP, Vathsala PG, Vieira V, Murthy RSR, Souto EB. Advances in nanomedicines for malaria treatment. Adv Colloid Inter Sci. 2013; 1(17): 201-202. ISSN 0001-8686. [CrossRef] [PubMed].
World Health Organization - WHO, 2018. Global Priority List of Antibiotic-Resistant Bacteria to Guide Research, Discovery and Development of New Antibiotics. [Link].
Santos-Magalhaes NS, Mosqueira VCF. Nanotechnology applied to the treatment of malaria. Adv Drug Deliv Rev. 2010; 62(4-5): 560-575. ISSN 0169-409X. [CrossRef] [PubMed].
Soares IS; Rodrigues MM. Malaria vaccine: roadblocks and possible solutions. Braz J Med Biol Res. 1998; 31(3): 317-332. ISSN 0100-879X. [CrossRef].
Olliaro P. Mode of action and mechanisms resistance for antimalarical drug. Pharmacol Therap. 2001; 89(2): 207-219. ISSN 01637258. [CrossRef] [PubMed].
Guerin PJ, Olliaro P, Nosten F, Druilhe P, Laxminarayan R, Binka F et al. Malaria: current status of control, diagnosis, treatment, and a proposed agenda for research and development. The Lancet Infect Dis. 2002; 2(9): 564-573. ISSN 1476 3099. [CrossRef] [PubMed].
Rai M, Ingle AP, Paralikar P, Gupta I, Medici S, Santos CA. Recent advances in use of silver nanoparticles as antimalarial agentes. Inter J Pharmac. 2017; 526(1): 254-270. ISSN 0378-5173. [CrossRef].
Gomes AR, Ravenhall M, Benavente ED, Talman A, Sutherland C, Roper C et al. Genetic diversity of next generation antimalarial targets: A baseline for drug resistance surveillance programmes. Inter J Paras: Drugs Drug Resist. 2017; 7(2):174-180. ISSN 2211-3207. [CrossRef] [PubMed].
Saifi MA, Beg T, Harrath AM, Altayalan FSH, Al-Quraishy S. Antimalarial drugs: mode of action and status of resistance. Afr J Pharm Pharmacol. 2013; 7(5):148-156. ISSN 1996-0816. [CrossRef].
Hu YQ, Zhang S, Xu Z, Sheng Z, Liu ML, Feng LS. 4-Quinolone hybrids and their antibacterial activities. Eur J Med Chem. 2017; 141(1): 335-345. ISSN 0223-5234. [CrossRef] [PubMed].
Kaur K, Jain M, Kaur T, Jain T. Review antimalarials from nature. Bioorg Med Chem. 2009; 17(9): 3229-3256. ISSN 0968-0896. [CrossRef].
Castañeda PMR, Alma B, Garcia E, Chávez D, Mata R. Secondary metabolites from the stem bark Celaenodendron mexicanum. J Nat Prod. 1993; 56(9): 1575-1579. ISSN 0163-3864. [CrossRef].
Camacho MDR, Phillipson JD, Croft SL, Solis PN, Marshall SJ, Ghazanfar SA. Screening of plant extracts for antiprotozoal and cytotoxic activities. J Ethnopharmacol. 2003, 89(2-3): 185-191.ISSN:0378-8741 [CrossRef]
Secco R, Cordeiro I. Picrodendraceae: In: Lista de Espécies da Flora do Brasil. Jardim Botânico do Rio de Janeiro-IPJBRJ. Disponível em: [Link]. Acesso em: 25 Mar. 2014.
Forzza RC. (Org). Catálogo de plantas e fungos do Brasil. v.1, Rio de Janeiro – Instituto de Pesquisas Jardim Botânico do Rio de Janeiro-IPJBRJ. 2010. ISBN: 978-85-88742-42-0.
Filho EMC. Plante as árvores do Xingu e Araguaia. São Paulo: Edição Revista e Ampliada, 2012. 260 p. ISBN: 978-85-8226-00 v5-0.
Worbes M, Klinger H, Revilla JD, Martins C. On dynamics, floristic subdivision and geographical distribution of varzea forest in Central Amazonia. J Veget Sci.1992; 3(4): 553-564. ISSN 1654-1103. [CrossRef].
Jeffreys MF, Nunez CV. Triterpenos das folhas de Piranhea trifoliata (Picrodendraceae). Acta Amaz. 2016; 46(2): 189-194. ISSN 1809-4392. [CrossRef].
Makler MT, Ries JM, Williams JA, Bancroft JE, Piper RC, Gibbins BL et al. Parasite lactate dehydrogenase as an assay for Plasmodium falciparum drug sensitivity. The Amer J Trop Med Hyg. 1993; 48(6): 739-741. ISSN 0002-9637. [CrossRef].
Mahato SB, Kundu AP. 13C NMR Spectra of Pentacyclic Triterpenoids Compilation and some Salient Features. Phytochemistry. 1994; 37(6): 1517-1575. ISSN 0031-9422. [CrossRef].
França VC, Vieira KVM, Lima EO, Barbosa-Filho JM, Cunha VL, Silva MS. Estudo fitoquímico das partes aéreas de Aristolocha birostris Ducht. (Aristolochiaceae). Rev Bras Farmacog. 2005; 15(4): 326- 330. ISSN 0102-696X. [CrossRef].
Cursino LMC, Mesquita ASS, Mesquita DWO, Fernandes CC, Pereira Junior OL, Amaral IL et al. Triterpenos das folhas de Minquartia guianensis Aubl. (Olacaceae). Acta Amaz. 2009; 39(1): 181-186. ISSN 1809-4392. [ CrossRef].
Lenta BN, Ngouela S, Boyom FF, Tantangmo F, Tchouya GRF, Tsamo E et al. Anti-plasmodial Activity of Some Constituents of the Root Bark of Harungana madagascariensis Lam. (Hypericaceae). Chem Pharm Bul. 2007; 55(3): 464-467. ISSN 1347-5223. [CrossRef] [PubMed].

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Author(s)

Laila da Silva Pedroza
National Institute for Research in the Amazon - INPA, Coordination of Research in Natural Products. Av. André Araújo, 2936, Aleixo, CEP 69060-001, Manaus, AM, Brazil.
Marcos Gabriel Maciel Salazar
National Institute for Research in the Amazon - INPA, Coordination of Research in Natural Products. Av. André Araújo, 2936, Aleixo, CEP 69060-001, Manaus, AM, Brazil.
Maria Izabel Correia Osorio
National Institute for Research in the Amazon - INPA, Coordination of Research in Natural Products. Av. André Araújo, 2936, Aleixo, CEP 69060-001, Manaus, AM, Brazil.
Maria Tereza Fachin-Espinar
National Institute of Amazonian Research (INPA), Coordination of Technology and Innovation, Laboratory of Bioprospecting and Biotechnology. Avenida André Araújo, 2936. Petrópolis, CEP 69067-375, Manaus, AM, Brazil.
Renata Cristina de Paula
Federal University of Minas Gerais, Faculty of Pharmacy, Department of Pharmaceutical Products. Av. Antônio Carlos, 6.627, Pampulha, CEP 31270-901, Belo Horizonte, MG, Brazil
Maria Fernanda Alves de Nascimento
Federal University of Minas Gerais, Faculty of Pharmacy, Department of Pharmaceutical Products. Av. Antônio Carlos, 6.627, Pampulha, CEP 31270-901, Belo Horizonte, MG, Brazil
Alaide Braga de Oliveira
Federal University of Minas Gerais, Faculty of Pharmacy, Department of Pharmaceutical Products. Av. Antônio Carlos, 6.627, Pampulha, CEP 31270-901, Belo Horizonte, MG, Brazil.
Cecilia Veronica Nunez
National Institute of Amazonian Research (INPA), Coordination of Technology and Innovation, Laboratory of Bioprospecting and Biotechnology. Avenida André Araújo, 2936. Petrópolis, CEP 69067-375, Manaus, AM, Brazil.

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Chemical study and antimalarial activity evaluation of branches of Piranhea trifoliata. Rev Fitos [Internet]. 2020 Dec. 18 [cited 2026 Jan. 16];14(4):476-91. Available from: https://revistafitos.far.fiocruz.br/index.php/revista-fitos/article/view/905

This work is licensed under a Creative Commons Attribution 4.0 International License.

[1] Valdés AF, Martínez JM, Lizama RS, Gaitén YG, Rodríguez DA. Payrol JA. In vitro antimalarial activity and cytotoxicity of some selected cuban medicinal plants. Rev Inst Med Trop São Paulo. 2010; 52(4): 197-201. ISSN 1678-9946. [CrossRef].

[2] Lenta BN, Ngouela S, Boyom FF, Tantangmo F, Tchouya GRF, Tsamo E et al. Anti-plasmodial Activity of Some Constituents of the Root Bark of Harungana madagascariensis Lam. (Hypericaceae). Chem Pharmac Bul. 2007; 55(3): 464-467. ISSN 1347-5223. [CrossRef] [PubMed].

[3] Hu YQ, Gao C, Zhang S, Xu L, Xu Z, Feng LS et al. Quinoline hybrids and their antiplasmodial and antimalarial activities. Eur J Med Chem. 2017; 20(139): 22-47. ISSN 0223-5234. [CrossRef] [PubMed].

[4] Aditya NP, Vathsala PG, Vieira V, Murthy RSR, Souto EB. Advances in nanomedicines for malaria treatment. Adv Colloid Inter Sci. 2013; 1(17): 201-202. ISSN 0001-8686. [CrossRef] [PubMed].

[5] World Health Organization - WHO, 2018. Global Priority List of Antibiotic-Resistant Bacteria to Guide Research, Discovery and Development of New Antibiotics. [Link].

[6] Santos-Magalhaes NS, Mosqueira VCF. Nanotechnology applied to the treatment of malaria. Adv Drug Deliv Rev. 2010; 62(4-5): 560-575. ISSN 0169-409X. [CrossRef] [PubMed].

[7] Soares IS; Rodrigues MM. Malaria vaccine: roadblocks and possible solutions. Braz J Med Biol Res. 1998; 31(3): 317-332. ISSN 0100-879X. [CrossRef].

[8] Olliaro P. Mode of action and mechanisms resistance for antimalarical drug. Pharmacol Therap. 2001; 89(2): 207-219. ISSN 01637258. [CrossRef] [PubMed].

[9] Guerin PJ, Olliaro P, Nosten F, Druilhe P, Laxminarayan R, Binka F et al. Malaria: current status of control, diagnosis, treatment, and a proposed agenda for research and development. The Lancet Infect Dis. 2002; 2(9): 564-573. ISSN 1476 3099. [CrossRef] [PubMed].

[10] Rai M, Ingle AP, Paralikar P, Gupta I, Medici S, Santos CA. Recent advances in use of silver nanoparticles as antimalarial agentes. Inter J Pharmac. 2017; 526(1): 254-270. ISSN 0378-5173. [CrossRef].

[11] Gomes AR, Ravenhall M, Benavente ED, Talman A, Sutherland C, Roper C et al. Genetic diversity of next generation antimalarial targets: A baseline for drug resistance surveillance programmes. Inter J Paras: Drugs Drug Resist. 2017; 7(2):174-180. ISSN 2211-3207. [CrossRef] [PubMed].

[12] Saifi MA, Beg T, Harrath AM, Altayalan FSH, Al-Quraishy S. Antimalarial drugs: mode of action and status of resistance. Afr J Pharm Pharmacol. 2013; 7(5):148-156. ISSN 1996-0816. [CrossRef].

[13] Hu YQ, Zhang S, Xu Z, Sheng Z, Liu ML, Feng LS. 4-Quinolone hybrids and their antibacterial activities. Eur J Med Chem. 2017; 141(1): 335-345. ISSN 0223-5234. [CrossRef] [PubMed].

[14] Kaur K, Jain M, Kaur T, Jain T. Review antimalarials from nature. Bioorg Med Chem. 2009; 17(9): 3229-3256. ISSN 0968-0896. [CrossRef].

[15] Castañeda PMR, Alma B, Garcia E, Chávez D, Mata R. Secondary metabolites from the stem bark Celaenodendron mexicanum. J Nat Prod. 1993; 56(9): 1575-1579. ISSN 0163-3864. [CrossRef].

[16] Camacho MDR, Phillipson JD, Croft SL, Solis PN, Marshall SJ, Ghazanfar SA. Screening of plant extracts for antiprotozoal and cytotoxic activities. J Ethnopharmacol. 2003, 89(2-3): 185-191.ISSN:0378-8741 [CrossRef]

[17] Secco R, Cordeiro I. Picrodendraceae: In: Lista de Espécies da Flora do Brasil. Jardim Botânico do Rio de Janeiro-IPJBRJ. Disponível em: [Link]. Acesso em: 25 Mar. 2014.

[18] Forzza RC. (Org). Catálogo de plantas e fungos do Brasil. v.1, Rio de Janeiro – Instituto de Pesquisas Jardim Botânico do Rio de Janeiro-IPJBRJ. 2010. ISBN: 978-85-88742-42-0.

[19] Filho EMC. Plante as árvores do Xingu e Araguaia. São Paulo: Edição Revista e Ampliada, 2012. 260 p. ISBN: 978-85-8226-00 v5-0.

[20] Worbes M, Klinger H, Revilla JD, Martins C. On dynamics, floristic subdivision and geographical distribution of varzea forest in Central Amazonia. J Veget Sci.1992; 3(4): 553-564. ISSN 1654-1103. [CrossRef].

[21] Jeffreys MF, Nunez CV. Triterpenos das folhas de Piranhea trifoliata (Picrodendraceae). Acta Amaz. 2016; 46(2): 189-194. ISSN 1809-4392. [CrossRef].

[22] Makler MT, Ries JM, Williams JA, Bancroft JE, Piper RC, Gibbins BL et al. Parasite lactate dehydrogenase as an assay for Plasmodium falciparum drug sensitivity. The Amer J Trop Med Hyg. 1993; 48(6): 739-741. ISSN 0002-9637. [CrossRef].

[23] Mahato SB, Kundu AP. 13C NMR Spectra of Pentacyclic Triterpenoids Compilation and some Salient Features. Phytochemistry. 1994; 37(6): 1517-1575. ISSN 0031-9422. [CrossRef].

[24] França VC, Vieira KVM, Lima EO, Barbosa-Filho JM, Cunha VL, Silva MS. Estudo fitoquímico das partes aéreas de Aristolocha birostris Ducht. (Aristolochiaceae). Rev Bras Farmacog. 2005; 15(4): 326- 330. ISSN 0102-696X. [CrossRef].

[25] Cursino LMC, Mesquita ASS, Mesquita DWO, Fernandes CC, Pereira Junior OL, Amaral IL et al. Triterpenos das folhas de Minquartia guianensis Aubl. (Olacaceae). Acta Amaz. 2009; 39(1): 181-186. ISSN 1809-4392. [ CrossRef].

[26] Lenta BN, Ngouela S, Boyom FF, Tantangmo F, Tchouya GRF, Tsamo E et al. Anti-plasmodial Activity of Some Constituents of the Root Bark of Harungana madagascariensis Lam. (Hypericaceae). Chem Pharm Bul. 2007; 55(3): 464-467. ISSN 1347-5223. [CrossRef] [PubMed].