Ethnopharmacological review, phytochemistry and bioactivity of the genus Geissospermum (Apocynaceae)
DOI:
https://doi.org/10.33448/rsd-v12i2.40047Keywords:
Indole alkaloids; Quina-quina; Geissospermum; Geissospermum reticulatum; Malaria.Abstract
This narrative review aims to update the ethnopharmacology, phytochemistry and biological activities of Geissospermum species described in the literature, in order to contribute to the knowledge of bioactive compounds of therapeutic interest and establish directions for future research with this genus. The term “Geissospermum” was used to perform searches in different databases such as NDLTD (Digital Library Network of Theses and Dissertations), Google Scholar, PubChem, Scifinder, Web of Science, SciELO, PubMed and Science Direct. Google's National Institute of Industrial Property and Patents (INPI) was also consulted. The keywords indole alkaloids, quina-quina, Geissospermum, Geissospermum reticulatum and malaria were used in the search. Publications in Portuguese, French, Spanish and English published between 1950 and 2022 were included. Indole alkaloids are the main secondary metabolites found in this genus, and several molecules have already been isolated, which may be related to the described pharmacological activities. Extracts and isolated compounds showed antitumor, antimalarial, antinociceptive, anti-inflammatory, anticholinesterase, anti-HIV, antimicrobial and antioxidant activity. Plants of the genus Geissospermum are used in Brazil mainly by the Amazonian peoples to treat various pathologies. Biological activities reported for extracts and isolated compounds are consistent with etonopharmacological use against malaria, cancer and other diseases. Future work with Geissospermum species is needed to elucidate the mechanism of action of the isolated alkaloids, as well as their toxicological profile.
References
Almeida, M. R., Lima, J. A., Santos, N. P. dos., & Pinto, A. C. (2009). Pereirina: o primeiro alcaloide isolado no Brasil? Revista Brasileira de Farmacognosia 19, 942–952. https://doi.org/10.1590/S0102-695X2009000600026
Araújo, J. Q., Lima, J. A., Pinto, A. C., de Alencastro, R. B., & Albuquerque, M. G. (2011). Docking of the alkaloid geissospermine into acetylcholinesterase: a natural scaffold targeting the treatment of Alzheimer’s disease. J Mol Model 17, 1401–1412. https://doi.org/10.1007/s00894-010-0841-2
Barbosa, C. V. O. (2016). Revisão taxonomica de Geissospermum Allemão (APOCYNACEAE) (Dissertação). Universidade Federal Rural da Amazônia, Belém, Brasil.
Bardin, L. (2010). Análise de conteúdo. Lisboa, Portugal.
Bastos, M. L. C. (2017). Avaliação da citotoxicidade e seletividade do extrato, frações e alcaloide de Geissospermum sericeum (Apocynaceae) em linhagens celulares ACP02, HepG2 e VERO (Dissertação). Universidade Federal do Pará, Belém, Brasil.
Beljanski, M. (2005). Flavopereirine-based pharmaceutical composition and use thereof for treating HIV. 1994/002146.
Bemis, D. L., Capodice, J. L., Desai, M., Katz, A. E., & Buttyan, R. (2009). Beta-carboline alkaloid-enriched extract from the amazonian rain forest tree pao pereira suppresses prostate cancer cells. J Soc Integr Oncol 7, 59–65.
Bertani, S., Bourdyb, G., Landaua, I., Robinsonc, J. C., Esterred, Ph., & Deharo, E. (2005). Evaluation of French Guiana traditional antimalarial remedies. J Ethnopharmacology 98, 45–54. https://doi.org/10.1016/j.jep.2004.12.020
Bhadane, B. S., Patil, M. P., Maheshwari, V. L., & Patil, R. H. (2018). Ethnopharmacology, phytochemistry, and biotechnological advances of family Apocynaceae: A review. Phytotherapy Research 32, 1181–1210. https://doi.org/10.1002/ptr.6066
Botsaris, A. S. (2007). Plants used traditionally to treat malaria in Brazil: the archives of Flora Medicinal. J Ethnobiology Ethnomedicine 3, 18. https://doi.org/10.1186/1746-4269-3-18
Brandão, M. G. L., Grandi, T. S. M., Rocha, E. M. M., Sawyer, D. R., & Krettli, A. U. (1992). Survey of medicinal plants used as antimalarials in the Amazon. J Ethnopharmacology 36, 175–182. https://doi.org/10.1016/0378-8741(92)90018-M
Camargo, M. R. M. (2011). Avaliação da atividade antimalárica e antimicrobiana de Geissospermum argenteum Woodson e Minquartia guianensis coletadas em Roraima. (Dissertação) Universidade Federal de Roraima, Boa Vista, Brasil.
Camargo, M. R. M., Amorim, R. C. das N., Silva, L. F. R. e, Carneiro, A. L. B., Vital, M. J. S., & Pohlit, A. M. (2013). Chemical composition, ethnopharmacology and biological activity of Geissospermum Allemão species (Apocynaceae Juss.). Revista Fitos 8. https://doi.org/10.5935/1808-9569.20130002
Chang, C., Zhao, W., Xie, B., Deng, Y., Han, T., Cui, Y., Dai, Y., Zhang, Z., Gao, J., Guo, H., & Yan, J. (2014). Pao Pereira Extract Suppresses Castration-Resistant Prostate Cancer Cell Growth, Survival, and Invasion Through Inhibition of NFκB Signaling. Integrative Cancer Therapies 13, 249–258. https://doi.org/10.1177/1534735413510557
Correia, A. F., Segovia, J. F. O., Gonsalves, M. C. A., Oliveira, V. L., Ssilveira, D., Carvalho, J. C. T., & Kanzaki, L. I. B. (2008). Amazonian plant crude extract screening for activity against multidrug-resistant bacteria. Eur Rev Med Pharmacol Sci 12, 369–380.
da Silva e Silva, J. V., Cordovil Brigido, H. P., Oliveira de Albuquerque, K. C., Miranda Carvalho, J., Ferreira Reis, J., Vinhal Faria, L., Coelho-Ferreira, M., Silveira, F. T., da Silva Carneiro, A., Percário, S., do Rosário Marinho, A. M., & Dolabela, M. F. (2019). Flavopereirine an alkaloid derived from Geissospermum vellosii Presents Leishmanicidal Activity In Vitro. Molecules 24, 785. https://doi.org/10.3390/molecules24040785
Dias, J. F. G. (2012). Fitoquímica e ensaios biológicos do extrato bruto etanólico, frações e substâncias isoladas provenientes das cascas de Geissospermum vellosii Allemão, (APOCYNACEAE) (Tese). Universidade Federal do Paraná, Curitiba, Brasil.
Fenner, R., Betti, A. H., Mentz, L. A., & Rates, S. M. K. (2006). Plantas utilizadas na medicina popular brasileira com potencial atividade antifúngica. Revista Brasileira de Ciências Farmacêuticas 42, 369–394. https://doi.org/10.1590/S1516-93322006000300007
Ferreira, A. B. (2015). Plantas utilizadas no tratamento de malária e males associados por comunidades tradicionais de xapuri, AC e Pauini, AM.(Tese). UNESP, Botucatu, Brasil.
Forzza, R. C., & Leitmam, P. (2010). Catálogo de Plantas e Fungos do Brasil, online. ed. Instituto de Pesquisa Jardim Botânico do Rio de Janeiro, Rio de Janeiro.
Fox Ramos, A. E., Alcover, C., Evanno, L., Maciuk, A., Litaudon, M., Duplais, C., Bernadat, G., Gallard, J.-F., Jullian, J.-C., Mouray, E., Grellier, P., Loiseau, P. M., Pomel, S., Poupon, E., Champy, P., & Beniddir, M. A. (2017). Revisiting previously investigated plants: A molecular networking-based study of Geissospermum laeve. Journal of Natural Products 80, 1007–1014. https://doi.org/10.1021/acs.jnatprod.6b01013
Freitas, J. C., & Fernandes, M. E.B. (2006). Uso de plantas medicinais pela comunidade de Enfarrusca, Bragança, Pará. Boletim do Museu Paraense Emílio Goeldi - Ciências Naturais 1, 11–26. https://doi.org/10.46357/bcnaturais.v1i3.724
Gordillo-Román, B., Reina, M., Ruiz-Mesia, L., Ruiz-Mesia, W., & Joseph-Nathan, P. (2013). Absolute configuration of indoline alkaloids from Geissospermum reticulatum. Tetrahedron Lett 54, 1693–1696. https://doi.org/10.1016/j.tetlet.2013.01.055
Hall, J. L., & Beljanski, S. P. (2008). Flavopereirine and alstonine combinations in the treatment and prevention of prostate cancer. USOO7341749B2.
Kobayashi, J., Ishiyama, H., Matsumoto, M., Sekiguchi, M., Shigemori, H., & Ohsaki, A. (2005). Two New Indole Alkaloids from Aspidosperma subincanum and Geissospermum vellosii. Heterocycles 66, 651. https://doi.org/10.3987/COM-05-S(K)63
Koch, I., Rapini, A., Simões, A. O., Kinoshita, L. S., Spina, A. P., & Castello, A. C. D. (2015) Apocynaceae in Lista de Espécies da Flora do Brasil. Jardim Botânico do Rio de Janeiro. http://floradobrasil.jbrj.gov.br/jabot/floradobrasil/FB48
Li, J.-M., Huang, Y.-C., Kuo, Y.-H., Cheng, C.-C., Kuan, F.-C., Chang, S.-F., Lee, Y.-R., Chin, C.-C., & Shi, C. S. (2019). Flavopereirine Suppresses the Growth of Colorectal Cancer Cells through P53 Signaling Dependence. Cancers (Basel) 11, 1034. https://doi.org/10.3390/cancers11071034
Lima, J. A., Costa, R. S., Epifânio, R. A., Castro, N. G., Rocha, M. S., & Pinto, A. C.(2009). Geissospermum vellosii stembark. Pharmacology Biochemistry and Behavior 92, 508–513. https://doi.org/10.1016/j.pbb.2009.01.024
Lima, J. A., Costa, T. W. R., Silva, L. L., Miranda, A. L. P., & Pinto, A. C. (2016). Antinociceptive and anti-inflammatory effects of a Geissospermum vellosii stem bark fraction. Anais da Academia Brasileira de Ciências 88, 237–248. https://doi.org/10.1590/0001-3765201520140374
Lima, J. A., R. Costa, T. W., da Fonseca, A. C. C., do Amaral, R. F., Nascimento, M. do D. S. B., Santos-Filho, O. A., de Miranda, A. L. P., Ferreira Neto, D. C., Lima, F. R. S., Hamerski, L., & Tinoco, L. W. (2020). Geissoschizoline, a promising alkaloid for Alzheimer’s disease: Inhibition of human cholinesterases, anti-inflammatory effects and molecular docking. Bioorganic Chemistry 104, 104215. https://doi.org/10.1016/j.bioorg.2020.104215
Liu, J., Fang, T., Li, M., Song, Y., Li, Junzun, Xue, Z., Li, Jiaxuan, Bu, D., Liu, W., Zeng, Q., Zhang, Y., Yun, S., Huang, R., & Yan, J. (2019). Pao Pereira Extract Attenuates Testosterone-Induced Benign Prostatic Hyperplasia in Rats by inhibiting 5α-Reductase. Scientific Reports 9, 19703. https://doi.org/10.1038/s41598-019-56145-z
Lorenzi, H. (1992). Manual de identificação e cultivo de plantas arbóreas nativas no Brasil, Plantarum. ed. São Paulo.
Martins, S. S. O. (2010). Efeitos dos alcalóides de Geissospermum urceolatum A. H. GENTRY (acariquara-branca) na pressão arterial e na contração do músculo liso de ratos. (Dissertação). Universidade Federal do Amazonas, Manaus, Brasil.
Mbeunkui, F., Grace, M. H., Lategan, C., Smith, P. J., Raskin, I., & Lila, M. A. (2012). In vitro antiplasmodial activity of indole alkaloids from the stem bark of Geissospermum vellosii. J Ethnopharmacology 139, 471–477. https://doi.org/10.1016/j.jep.2011.11.036
Milliken, W. (1997). Medicina Tradicional Antimalárica em Roraima, Brasil. Botânica Econômica 53, 212–237.
Moore, R. E., & Rapoport, H. (1973). Geissovelline, a new alkaloid from Geissospermum vellossi. Journal of Organic Chemistry 38, 215–230. https://doi.org/10.1021/jo00942a007
Morais, J. A. (2012). Estudo das ações cardiovasculares da fração alcaloídica obtida da espécie nativa amazônica Geissospermum argenteum WOODSON. (Dissertação). Universidade Federal do Amazonas, Manaus, Brasil.
Muñoz, V., Sauvain, M., Bourdy, G., Callapa, J., Bergeron, S., Rojas, I., Bravo, J. A., Balderrama, L., Ortiz, B., Gimenez, A., & Deharo, E. (2000). A search for natural bioactive compounds in Bolivia through a multidisciplinary approach. J Ethnopharmacology 69, 127–137. https://doi.org/10.1016/S0378-8741(99)00148-8
Oliveira, B. (2018). Composição química e atividade antimalárica de Geissospermum urceolatum A. H. Gentry (Apocynaceae). (Tese). Universidade Federal do Amazonas, Manaus, Brasil.
Paccioni, J. P., & Husson, H. P. (1978). Alcaloides de Geissospermum argetum (APOCYNACEAE). Phytochemistry 17, 2146–2147.
Rapoport, H., & Moore, R. E. (1962). Alkaloids of Geissospermum vellosii. Isolation and Structure Determinations of Vellosimine, Vellosiminol, and Geissolosimine. Journal of Organic Chemistry 27, 2981–2985. https://doi.org/10.1021/jo01056a004
Rapoport, H., Onak, T. P., Hughes, N. A., & Reinecke, M. G. (1958). Alkaloids of Geissospermum vellosii. Journal of the American Chemical Society 80, 1601–1604. https://doi.org/10.1021/ja01540a023
Reina, M., Ruiz-Mesia, W., López-Rodríguez, M., Ruiz-Mesia, L., González-Coloma, A., & Martínez-Díaz, R. (2012). Indole Alkaloids from Geissospermum reticulatum. Journal of Natural Products 75, 928–934. https://doi.org/10.1021/np300067m
Ribeiro, J. E. L. S., Hopkins, M. J. G., Vicentini, A., Sothers, C. A., Costa, M. A. S., Brito, J. M., Souza, M. A. D., Martins, L. H. P., Lohmann, L. G., Assunção, P. A. C. L., Pereira, E. C., Silva, C. F., Mesquita, M. R., & Procópio, L. C. (1999). Flora da Reserva Ducke Guia de identificação das plantas vasculares de uma floresta de terra-firme na Amazônia Central. INPA-DFID, Manaus.800p
Sajkowska-Kozielewicz, J. J., Kozielewicz, P., Barnes, N. M., Wawer, I., & Paradowska, K. (2016). Antioxidant, Cytotoxic, and Antiproliferative Activities and Total Polyphenol Contents of the Extracts of Geissospermum reticulatum Bark. Oxidative Medicine and Cellular Longevity 2016, 1–8. https://doi.org/10.1155/2016/2573580
Sajkowska-Kozielewicz, J. J., Kozielewicz, P., Makarova, K., Stocki, M., Barnes, N. M., & Paradowska, K. (2020). Geissospermiculatine, a New Alkaloid from Geissospermum reticulatum Bark. Molecules 26, 143. https://doi.org/10.3390/molecules26010143
Santos, N. P. dos. (2007). Passando da doutrina à prática: Ezequiel Corrêa dos Santos e a farmácia nacional. Quimica Nova 30, 1038–1045. https://doi.org/10.1590/S0100-40422007000400049
Saraiva, R. M. C. (2012). Atividade antibacteriana de plantas medicinais frente á bactérias multirresistentes e a sua interação com drogas antimicrobianas. (Dissertação). Universidade Federal do Pará, Belém, Brasil.
Silva, J. V. S. e. (2016). Estudos farmacognosticos, fitoquímicos e atividades antileishmania de espécies Geissospermun (Apocynaceae). (Dissertação) Universidade Federal do Pará, Belem, Brasil.
Simões, C. M. O., Schenkel, E. P., Mello, J. C. P., & Petrovick, P. R. (2017). Farmacognosia: do produto natural ao medicamento. Porto Alegre, Brasil.
Stalcup, M. M. (2000) Plantas de uso medicinal ou ritual numa feira livre no Rio de Janeiro. (Dissertação). Universidade Federal do Rio de Janeiro, Rio de Janeiro, Brasil.
Steele, J. C. P., Veitch, N. C., Kite, G. C., Simmonds, M. S. J., & Warhurst, D. C. (2002). Indole and β-Carboline Alkaloids from Geissospermum s ericeum. Journal of Natural Products 65, 85–88. https://doi.org/10.1021/np0101705
Veiga, J. B., & Scudeller, V. V. (2015). Etnobotânica e medicina popular no tratamento de malária e males associados na comunidade ribeirinha Julião – baixo Rio Negro (Amazônia Central). Revista Brasileira de Plantas Medicinais 17, 737–747. https://doi.org/10.1590/1983-084X/14_039
Viana, S. S., Santos, J. U. M., & Simões, A. O. (2017). Diversidade taxonômica de Apocynaceae na ilha do Marajó, PA, Brasil. Rodriguésia 68, 623–652. https://doi.org/10.1590/2175-7860201768221
Werner, J. A. T., Oliveira, S. M., Martins, D. F., Mazzardo, L., Dias, J. de F. G., Lordello, A. L. L., Miguel, O. G., Royes, L. F., Ferreira, J., & Santos, A. R. S. (2009). Evidence for a role of 5-HT1A receptor on antinociceptive action from Geissospermum vellosii. J Ethnopharmacology 125, 163–169. https://doi.org/10.1016/j.jep.2009.05.026
Yeh, H.-T., Tsai, Y.-S., Chen, M.-S., Li, Y.-Z., Lin, W.-C., Lee, Y.-R., Tseng, Y.-S., & Sheu, S.-M. (2019). Flavopereirine induces cell cycle arrest and apoptosis via the AKT/p38 MAPK/ERK1/2 signaling pathway in human breast cancer cells. European Journal of Pharmacology 863, 172658. https://doi.org/10.1016/j.ejphar.2019.172658
Yu, J., & Chen, Q. (2014). The plant extract of Pao Pereira potentiates carboplatin effects against ovarian cancer. Pharmaceutical Biology 52, 36–43. https://doi.org/10.3109/13880209.2013.808232
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2023 Dayan de Araújo Marques; Fernando Berton Zanchi; Geisa Paulino Caprini Evaristo
This work is licensed under a Creative Commons Attribution 4.0 International License.
Authors who publish with this journal agree to the following terms:
1) Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.
2) Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal.
3) Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work.
