Licarin A, a neolignan isolated from Nectandra oppositifolia Nees & Mart. (Lauraceae), exhibited moderate preclinical efficacy against Schistosoma mansoni infection.
Nectandra oppositifolia
antischistosomal activity
licarin A
lignan
schistosoma
schistosomiasis
Journal
Phytotherapy research : PTR
ISSN: 1099-1573
Titre abrégé: Phytother Res
Pays: England
ID NLM: 8904486
Informations de publication
Date de publication:
Sep 2021
Sep 2021
Historique:
revised:
03
05
2021
received:
12
02
2021
accepted:
18
05
2021
pubmed:
6
6
2021
medline:
30
9
2021
entrez:
5
6
2021
Statut:
ppublish
Résumé
Schistosomiasis is a widespread human parasitic disease currently affecting over 200 million people, particularly in poor communities. Chemotherapy for schistosomiasis relies exclusively on praziquantel (PZQ). Previous studies have shown that licarin A (LIC-A), a dihydrobenzofuran neolignan, exhibited in vitro antiparasitic activity against Schistosoma mansoni adult worms. This study aimed to investigate the potential of LIC-A, isolated as main metabolite from leaves of Nectandra oppositifolia Nees & Mart. (Lauraceae), as an antischistosomal agent orally active in schistosomiasis animal model. PZQ was used as a reference compound. As result, LIC-A showed, at a single dose of 400 mg/kg, to be able to partially cure infected mice (worm burden reductions of ~50%). Parasite eggs, that are responsible for a variety of pathologies and transmission of schistosomiasis, were also moderately inhibited by LIC-A (egg burden reductions of ~50%-60%). Furthermore, it was observed that LIC-A achieved a slight reduction of hepatomegaly and splenomegaly. Collectively, although LIC-A was partially active when administered orally, these results give support for the antiparasitic potential LIC-A as lead compound for novel antischistosomal agent.
Substances chimiques
Lignans
0
licarin A
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
5154-5162Subventions
Organisme : Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)
Organisme : Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES/PNPD)
ID : 88887.351532/2019-00
Organisme : Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
ID : 2016/22488-3
Organisme : Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
ID : 2018/07885-1
Organisme : Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
ID : 2019/25289-0
Organisme : Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)
ID : 2019/25905-2
Informations de copyright
© 2021 John Wiley & Sons Ltd.
Références
Aires, A. L., Ximenes, E. C., Barbosa, V. X., Góes, A. J., Souza, V. M., & Albuquerque, M. C. (2014). Beta-Lapachone: A naphthoquinone with promising antischistosomal properties in mice. Phytomedicine, 21(3), 261-267.
Alvarenga, D. J., Matias, L. M. F., Oliveira, L. M., Leão, L. P. M. O., Hawkes, J. A., Raimundo, B. V. B., … Carvalho, D. T. (2020). Exploring how structural changes to new Licarin A derivatives effects their bioactive properties against rapid growing mycobacteria and biofilm formation. Microbial Pathogenesis, 144, 104203.
Amorim, C. R., Pavani, T. F. A., Lopes, A. F. S., Duque, M. D., Mengarda, A. C. A., Silva, M. P., … Rando, D. G. G. (2020). Schiff bases of 4-phenyl-2-aminothiazoles as hits to new antischistosomals: Synthesis, in vitro, in vivo and in silico studies. European Journal of Pharmaceutical Sciences, 150, 105371-105380.
Barbosa-Filho, J. M., Cunha, E. V. L., & Silva, M. S. (1998). Complete assignment of the 1H and 13C NMR spectra of some lignoids from Lauraceae. Magnetic Resonance in Chemistry, 36, 929-935.
Costa, P. D. S., Zuza da Silva, O. O., Costa, D. S., Silva, L. A. O., de Faria Pinto, P., da Silva, M. P. N., … Da Silva Filho, A. A. (2020). Assessment of the in vitro antischistosomal activities of the extracts and compounds from Solidago Microglossa DC (Asteraceae) and Aristolochia Cymbifera Mart. & Zucc. (Aristolochiaceae). Evidence-based Complementary and Alternative Medicine, 2020, 1726365.
de Almeida, L. M., de Carvalho, L. S., Gazolla, M. C., Silva Pinto, P. L., da Silva, M. P., de Moraes, J., & Da Silva Filho, A. A. (2016). Flavonoids and sesquiterpene lactones from Artemisia absinthium and Tanacetum parthenium against Schistosoma mansoni worms. Evidence-based Complementary and Alternative Medicine, 2016, 9521349.
de Brito, M. G., Mengarda, A. C., Oliveira, G. L., Cirino, M. E., Silva, T. C., de Oliveira, R. N., … de Moraes, J. (2020). Therapeutic effect of diminazene aceturate on parasitic blood fluke Schistosoma mansoni infection. Antimicrobial Agents and Chemotherapy, 64(11), e01372-e01320.
de Brito, M. R. M., Peláez, W. J., Faillace, M. S., Militão, G. C. G., Almeida, J. R. G. S., Arguello, G. A., … de Moraes, J. (2017). Cyclohexene-fused 1,3-oxazines with selective antibacterial and antiparasitic action and low cytotoxic effects. Toxicology In Vitro, 44, 273-279.
de Castro Oliveira, L. G., Brito, L. M., de Moraes Alves, M. M., Amorim, L. V., Sobrinho-Júnior, E. P., de Carvalho, C. E., … de Amorim Carvalho, F. A. (2017). In vitro effects of the neolignan 2,3-dihydrobenzofuran against Leishmania amazonensis. Basic & Clinical Pharmacology & Toxicology, 120, 52-58.
de Moraes, J. (2015). Natural products with antischistosomal activity. Future Medicinal Chemistry, 7, 801-820.
de Moraes, J., Dario, B. S., Couto, R. A. A., Pinto, P. L. S., & Ferreira, A. M. C. (2015). Antischistosomal activity of oxindolimine-metal complexes. Antimicrobial Agents and Chemotherapy, 59(10), 6648-6652.
de Moraes, J., de Oliveira, R. N., Costa, J. P., Junior, A. L., de Sousa, D. P., Freitas, R. M., … Pinto, P. L. (2014). Phytol, a diterpene alcohol from chlorophyll, as a drug against neglected tropical disease schistosomiasis mansoni. PLoS Neglected Tropical Diseases, 8(1), e2617.
de Moraes, J., & Geary, T. G. (2020). FDA-approved Antiparasitic drugs in the 21st century: A success for helminthiasis? Trends in Parasitology, 36(7), 573-575.
Dias, M. M., Zuza, O., Riani, L. R., de Faria Pinto, P., Pinto, P. L. S., Silva, M. P., … Da Silva Filho, A. A. (2017). In vitro schistosomicidal and antiviral activities of Arctium lappa L. (Asteraceae) against Schistosoma mansoni and herpes simplex virus-1. Biomedicine & Pharmacotherapy, 94, 489-498.
Eraky, M. A., El-Kholy, A. A., Rashed, G. A., Hammam, O. A., Moharam, A. F., Abou-Ouf, E. A., … Hamdan, D. I. (2016). Dose-response relationship in Schistosoma mansoni juvenile and adult stages following limonin treatment in experimentally infected mice. Parasitology Research, 115(10), 4045-4054.
Guerra, R. A., Silva, M. P., Silva, T. C., Salvadori, M. C., Teixeira, F. S., Oliveira, R. N., … de Moraes, J. (2019). In vitro and in vivo studies of spironolactone as an antischistosomal drug capable of clinical repurposing. Antimicrobial Agents and Chemotherapy, 63(3), e01722-e01718.
Guimarães, M. A., de Oliveira, R. N., de Almeida, R. L., Mafud, A. C., Sarkis, A. L. V., Ganassin, R., … Leite, J. R. S. A. (2018). Epiisopilosine alkaloid has activity against Schistosoma mansoni in mice without acute toxicity. PLoS One, 13(5), e0196667.
Guimarães, M. A., de Oliveira, R. N., Véras, L. M., Lima, D. F., Campelo, Y. D., Campos, S. A., … Leite, J. R. (2015). Anthelmintic activity in vivo of epiisopiloturine against juvenile and adult worms of Schistosoma mansoni. PLoS Neglected Tropical Diseases, 9(3), e0003656.
Kabuyaya, M., Chimbari, M. J., & Mukaratirwa, S. (2018). Efficacy of praziquantel treatment regimens in pre-school and school aged children infected with schistosomiasis in sub-Saharan Africa: A systematic review. Infectious Diseases of Poverty, 7, 73-79.
Lago, E. M., Silva, M. P., Queiroz, T. G., Mazloum, S. F., Rodrigues, V. C., Carnauba, P. U., … de Moraes, J. (2019). Phenotypic screening of nonsteroidal anti-inflammatory drugs identified mefenamic acid as a drug for the treatment of schistosomiasis. eBioMedicine, 43, 370-379.
Lago, E. M., Xavier, R. P., Teixeira, T. R., Silva, L. M., Silva-Filho, A. A., & de Moraes, J. (2018). Antischistosomal agents: State of art and perspectives. Future Medicinal Chemistry, 10(1), 89-120.
Lombardo, F. C., Pasche, V., Panic, G., Endriss, Y., & Keiser, J. (2019). Life cycle maintenance and drug-sensitivity assays for early drug discovery in Schistosoma mansoni. Nature Protocols, 14(2), 461-481.
Macías-Villamizar, V. E., Cuca-Suárez, L. E., & Coy-Barrera, E. D. (2015). Genus Nectandra: Phytochemistry and biological activity. Boletin Latinoamericano y del Caribe de Plantas Medicinales y Aromaticas, 14, 317-342.
Mafud, A. C., Ferreira, L. G., Mascarenhas, Y. P., Andricopulo, A. D., & de Moraes, J. (2016). Discovery of novel antischistosomal agents by molecular modeling approaches. Trends in Parasitology, 32, 874-886.
Mafud, A. C., Silva, M. P. N., Nunes, G. B. L., Oliveira, M. A. R., Batista, L. F., Rubio, T. I., … de Moraes, J. (2018). Antiparasitic, structural, pharmacokinetic, and toxicological properties of riparin derivatives. Toxicology In Vitro, 50, 1-10.
Maheswari, U., Ghosh, K., & Sadras, S. R. (2018). Licarin A induces cell death by activation of autophagy and apoptosis in non-small cell lung cancer cells. Apoptosis, 23(3-4), 210-225.
McManus, D. P., Dunne, D. W., Sacko, M., Utzinger, J., Vennervald, B. J., & Zhou, X. N. (2018). Schistosomiasis. Nature Reviews. Disease Primers, 4, 13-31.
Meleti, V. R., Esperandim, V. R., Flauzino, L. G. B., Prizantelli, A. H., Paula, L. A. L., Magalhães, L. G., … Silva, M. L. A. (2020). (±)-Licarin A and its semi-synthetic derivatives: In vitro and in silico evaluation of trypanocidal and schistosomicidal activities. Acta Tropica, 202, 105248.
Mengarda, A. C., Mendonça, P. S., Morais, C. S., Cogo, R. M., Mazloum, S. F., Salvadori, M. C., … Moraes, J. (2020). Antiparasitic activity of piplartine (piperlongumine) in a mouse model of schistosomiasis. Acta Tropica, 205, 105350.
Morais, T. R., Conserva, G. A. A., Varela, M. T., Costa-Silva, T. A., Thevenard, F., Ponci, V., … Lago, J. H. G. (2020). Improving the drug-likeness of inspiring natural products - Evaluation of the antiparasitic activity against Trypanosoma cruzi through semi-synthetic and simplified analogues of licarin A. Scientific Reports, 10(1), 5467.
Néris, P. L., Caldas, J. P., Rodrigues, Y. K., Amorim, F. M., Leite, J. A., Rodrigues-Mascarenhas, S., … Oliveira, M. R. (2013). Neolignan Licarin A presents effect against Leishmania (Leishmania) major associated with immunomodulation in vitro. Experimental Parasitology, 135(2), 307-313.
Pellegrino, J., Oliveira, C. A., Faria, J., & Cunha, A. S. (1962). New approach to the screening of drugs in experimental schistosomiasis mansoni in mice. The American Journal of Tropical Medicine and Hygiene, 11, 201-215.
Pereira, A. C., Magalhães, L. G., Gonçalves, U. O., Luz, P. P., Moraes, A. C., Rodrigues, V., … Silva, M. L. (2011). Schistosomicidal and trypanocidal structure-activity relationships for (±)-licarin A and its (−)- and (+)-enantiomers. Phytochemistry, 72(11-12), 1424-1430.
Pereira, A. C., Silva, M. L., Souza, J. M., Laurentiz, R. S., Rodrigues, V., Januário, A. H., … Magalhães, L. G. (2015). In vitro and in vivo anthelmintic activity of (−)-6,6′-dinitrohinokinin against schistosomula and juvenile and adult worms of Schistosoma mansoni. Acta Tropica, 149, 195-201.
Pereira, V. R. D., da Silveira, L. S., Mengarda, A. C., Alves Júnior, I. J., da Silva, O. O. Z., Miguel, F. B., … da Silva Filho, A. A. (2021). Antischistosomal properties of aurone derivatives against juvenile and adult worms of Schistosoma mansoni. Acta Tropica, 213, 105741.
Rando, D. G. G., Costa, M. O. L., Pavani, T. F. A., Oliveira, T., Santos, T. F. D., Amorim, C. R., … de Moraes, J. (2019). Vanillin-related N-acylhydrazones: Synthesis, antischistosomal properties and target fishing studies. Current Topics in Medicinal Chemistry, 19(14), 1241-1251.
Rocha, J. A., Andrade, I. M., Véras, L. M., Quelemes, P. V., Lima, D. F., Soares, M. J., … Leite, J. R. (2017). Anthelmintic, antibacterial and cytotoxicity activity of imidazole alkaloids from Pilocarpus microphyllus leaves. Phytotherapy Research, 31(4), 624-630.
Roquini, D. B., Cogo, R. M., Mengarda, A. C., Mazloum, S. F., Morais, C. S., Xavier, R. P., … de Moraes, J. (2019). Promethazine exhibits antiparasitic properties in vitro and reduces worm burden, egg production, hepato-, and splenomegaly in a schistosomiasis animal model. Antimicrobial Agents and Chemotherapy, 63(12), e01208-e01219.
Sessa, D. P., Mengarda, A. C., Simplicio, P. E., Antar, G. M., Lago, J. H. G., & de Moraes, J. (2020). 15β-Senecioyl-oxy-ent-kaur-16-en-19-oic acid, a diterpene isolated from Baccharis lateralis, as promising oral compound for the treatment of schistosomiasis. Journal of Natural Products, 83(12), 3744-3750.
Silva, M. P., Oliveira, R. N., Mengarda, A. C., Roquini, D. B., Allegretti, S. M., Salvadori, M. C., … de Moraes, J. (2017). Antiparasitic activity of nerolidol in a mouse model of schistosomiasis. International Journal of Antimicrobial Agents, 50(3), 467-472.
Silva, M. P., Silva, T. M., Mengarda, A. C., Salvadori, M. C., Teixeira, F. S., Alencar, S. M., … de Moraes, J. (2021). Brazilian red propolis exhibits antiparasitic properties in vitro and reduces worm burden and egg production in an mouse model harboring either early or chronic Schistosoma mansoni infection. Journal of Ethnopharmacology, 264, 113387.
Silva, T. C., Mengarda, A. C., Silva, B. C., Relvas-Lima, T. S., Rodrigues, V. C., Salvadori, M. C., … Moraes, J. (2021). New evidence for tamoxifen as an antischistosomal agent: In vitro, in vivo and target fishing studies. Future Medicinal Chemistry, 13, 945-957.
World Health Organization. (2020). Schistosomiasis. Geneva, Switzerland: WHO. https://www.who.int/news-room/fact-sheets/detail/schistosomiasis
Xavier, R. P., Mengarda, A. C., Silva, M. P., Roquini, D. B., Salvadori, M. C., Teixeira, F. S., … de Moraes, J. (2020). H1-antihistamines as antischistosomal drugs: In vitro and in vivo studies. Parasites & Vectors, 13, 278.
Yolles, T. K., Moore, D. V., Degiusti, D. L., Ripsom, C. A., & Meleney, H. E. (1947). A technique for the perfusion of laboratory animals for the recovery of schistosomes. Journal of Parasitology, 33, 419-426.
Zálešák, F., Bon, D. J. D., & Pospíšil, J. (2019). Lignans and Neolignans: Plant secondary metabolites as a reservoir of biologically active substances. Pharmacology Research, 246, 104284.