Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)

Silva, Ellen Cristina Costa; Coelho Cavalcanti, Bruno; Amorim, Rodrigo C.N.; Lucena, Jorcilene F.; Quadros, Dulcimar S.; Tadei, Wanderli Pedro; Montenegro, Raquel Carvalho; Costa-Lotufo, Leticia Veras; Pessoa, Cláudia do Ó.; Moraes, Manœl Odorico de; Nunomura, Rita de Cássia Saraiva; Nunomura, Sergio Massayoshi; Melo, Márcia R.S.; Andrade Neto, Valter Ferreira de; Silva, Luis Francisco Rocha; Vieira, Pedro Paulo Ribeiro; Pohlit, Adrian Martin

Artigo

Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)

In the present study, in vitro techniques were used to investigate a range of biological activities of known natural quassinoids isobrucein B (1) and neosergeolide (2), known semi-synthetic derivative 1,12-diacetylisobrucein B (3), and a new semi-synthetic derivative, 12-acetylneosergeolide (4). The...

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Autor principal:	Silva, Ellen Cristina Costa
Outros Autores:	Coelho Cavalcanti, Bruno, Amorim, Rodrigo C.N., Lucena, Jorcilene F., Quadros, Dulcimar S., Tadei, Wanderli Pedro, Montenegro, Raquel Carvalho, Costa-Lotufo, Leticia Veras, Pessoa, Cláudia do Ó., Moraes, Manœl Odorico de, Nunomura, Rita de Cássia Saraiva, Nunomura, Sergio Massayoshi, Melo, Márcia R.S., Andrade Neto, Valter Ferreira de, Silva, Luis Francisco Rocha, Vieira, Pedro Paulo Ribeiro, Pohlit, Adrian Martin
Grau:	Artigo
Idioma:	English
Publicado em:	Memórias do Instituto Oswaldo Cruz 2020
Assuntos:	Isobrucein B Neosergeolide Quassinoid Derivative Aedes Animals Artemia Cell Strain Hl 60 Chemistry Drug Effect Erythrocyte Hemolysis Human Isolation And Purification Ld 50 Medicinal Plant Mouse Plasmodium Falciparum Simaroubaceae Aedes Animal Artemia Erythrocytes Hemolysis Hl-60 Cells Humans Lethal Dose 50 Mice Plants, Medicinal Plasmodium Falciparum Quassins Simaroubaceae Aedes Aegypti Artemia Artemia Franciscana Picrolemma Plasmodium Falciparum Simaroubaceae
Acesso em linha:	https://repositorio.inpa.gov.br/handle/1/14515

id	oai:repositorio:1-14515
recordtype	dspace
spelling	oai:repositorio:1-14515 Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae) Silva, Ellen Cristina Costa Coelho Cavalcanti, Bruno Amorim, Rodrigo C.N. Lucena, Jorcilene F. Quadros, Dulcimar S. Tadei, Wanderli Pedro Montenegro, Raquel Carvalho Costa-Lotufo, Leticia Veras Pessoa, Cláudia do Ó. Moraes, Manœl Odorico de Nunomura, Rita de Cássia Saraiva Nunomura, Sergio Massayoshi Melo, Márcia R.S. Andrade Neto, Valter Ferreira de Silva, Luis Francisco Rocha Vieira, Pedro Paulo Ribeiro Pohlit, Adrian Martin Isobrucein B Neosergeolide Quassinoid Derivative Aedes Animals Artemia Cell Strain Hl 60 Chemistry Drug Effect Erythrocyte Hemolysis Human Isolation And Purification Ld 50 Medicinal Plant Mouse Plasmodium Falciparum Simaroubaceae Aedes Animal Artemia Erythrocytes Hemolysis Hl-60 Cells Humans Lethal Dose 50 Mice Plants, Medicinal Plasmodium Falciparum Quassins Simaroubaceae Aedes Aegypti Artemia Artemia Franciscana Picrolemma Plasmodium Falciparum Simaroubaceae In the present study, in vitro techniques were used to investigate a range of biological activities of known natural quassinoids isobrucein B (1) and neosergeolide (2), known semi-synthetic derivative 1,12-diacetylisobrucein B (3), and a new semi-synthetic derivative, 12-acetylneosergeolide (4). These compounds were evaluated for general toxicity toward the brine shrimp species Artemia franciscana, cytotoxicity toward human tumour cells, larvicidal activity toward the dengue fever mosquito vector Aedes aegypti, haemolytic activity in mouse erythrocytes and antimalarial activity against the human malaria parasite Plasmodium falciparum. Compounds 1 and 2 exhibited the greatest cytotoxicity against all the tumor cells tested (IC50 = 5-27 μg/L) and against multidrug-resistant P. falciparum K1 strain (IC50 = 1.0-4.0 μg/L) and 3 was only cytotoxic toward the leukaemia HL-60 strain (IC50 = 11.8 μg/L). Quassinoids 1 and 2 (LC50 = 3.2-4.4 mg/L) displayed greater lethality than derivative 4 (LC50 = 75.0 mg/L) toward A. aegypti larvae, while derivative 3 was inactive. These results suggest a novel application for these natural quassinoids as larvicides. The toxicity toward A. franciscana could be correlated with the activity in several biological models, a finding that is in agreement with the literature. Importantly, none of the studied compounds exhibited in vitro haemolytic activity, suggesting specificity of the observed cytotoxic effects. This study reveals the biological potential of quassinoids 1 and 2 and to a lesser extent their semi-synthetic derivatives for their in vitro antimalarial and cytotoxic activities. 2020-04-24T16:49:24Z 2020-04-24T16:49:24Z 2009 Artigo https://repositorio.inpa.gov.br/handle/1/14515 10.1590/S0074-02762009000100008 en Volume 104, Número 1, Pags. 48-55 Attribution-NonCommercial-NoDerivs 3.0 Brazil http://creativecommons.org/licenses/by-nc-nd/3.0/br/ application/pdf Memórias do Instituto Oswaldo Cruz
institution	Instituto Nacional de Pesquisas da Amazônia - Repositório Institucional
collection	INPA-RI
language	English
topic	Isobrucein B Neosergeolide Quassinoid Derivative Aedes Animals Artemia Cell Strain Hl 60 Chemistry Drug Effect Erythrocyte Hemolysis Human Isolation And Purification Ld 50 Medicinal Plant Mouse Plasmodium Falciparum Simaroubaceae Aedes Animal Artemia Erythrocytes Hemolysis Hl-60 Cells Humans Lethal Dose 50 Mice Plants, Medicinal Plasmodium Falciparum Quassins Simaroubaceae Aedes Aegypti Artemia Artemia Franciscana Picrolemma Plasmodium Falciparum Simaroubaceae
spellingShingle	Isobrucein B Neosergeolide Quassinoid Derivative Aedes Animals Artemia Cell Strain Hl 60 Chemistry Drug Effect Erythrocyte Hemolysis Human Isolation And Purification Ld 50 Medicinal Plant Mouse Plasmodium Falciparum Simaroubaceae Aedes Animal Artemia Erythrocytes Hemolysis Hl-60 Cells Humans Lethal Dose 50 Mice Plants, Medicinal Plasmodium Falciparum Quassins Simaroubaceae Aedes Aegypti Artemia Artemia Franciscana Picrolemma Plasmodium Falciparum Simaroubaceae Silva, Ellen Cristina Costa Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)
topic_facet	Isobrucein B Neosergeolide Quassinoid Derivative Aedes Animals Artemia Cell Strain Hl 60 Chemistry Drug Effect Erythrocyte Hemolysis Human Isolation And Purification Ld 50 Medicinal Plant Mouse Plasmodium Falciparum Simaroubaceae Aedes Animal Artemia Erythrocytes Hemolysis Hl-60 Cells Humans Lethal Dose 50 Mice Plants, Medicinal Plasmodium Falciparum Quassins Simaroubaceae Aedes Aegypti Artemia Artemia Franciscana Picrolemma Plasmodium Falciparum Simaroubaceae
description	In the present study, in vitro techniques were used to investigate a range of biological activities of known natural quassinoids isobrucein B (1) and neosergeolide (2), known semi-synthetic derivative 1,12-diacetylisobrucein B (3), and a new semi-synthetic derivative, 12-acetylneosergeolide (4). These compounds were evaluated for general toxicity toward the brine shrimp species Artemia franciscana, cytotoxicity toward human tumour cells, larvicidal activity toward the dengue fever mosquito vector Aedes aegypti, haemolytic activity in mouse erythrocytes and antimalarial activity against the human malaria parasite Plasmodium falciparum. Compounds 1 and 2 exhibited the greatest cytotoxicity against all the tumor cells tested (IC50 = 5-27 μg/L) and against multidrug-resistant P. falciparum K1 strain (IC50 = 1.0-4.0 μg/L) and 3 was only cytotoxic toward the leukaemia HL-60 strain (IC50 = 11.8 μg/L). Quassinoids 1 and 2 (LC50 = 3.2-4.4 mg/L) displayed greater lethality than derivative 4 (LC50 = 75.0 mg/L) toward A. aegypti larvae, while derivative 3 was inactive. These results suggest a novel application for these natural quassinoids as larvicides. The toxicity toward A. franciscana could be correlated with the activity in several biological models, a finding that is in agreement with the literature. Importantly, none of the studied compounds exhibited in vitro haemolytic activity, suggesting specificity of the observed cytotoxic effects. This study reveals the biological potential of quassinoids 1 and 2 and to a lesser extent their semi-synthetic derivatives for their in vitro antimalarial and cytotoxic activities.
format	Artigo
author	Silva, Ellen Cristina Costa
author2	Coelho Cavalcanti, Bruno Amorim, Rodrigo C.N. Lucena, Jorcilene F. Quadros, Dulcimar S. Tadei, Wanderli Pedro Montenegro, Raquel Carvalho Costa-Lotufo, Leticia Veras Pessoa, Cláudia do Ó. Moraes, Manœl Odorico de Nunomura, Rita de Cássia Saraiva Nunomura, Sergio Massayoshi Melo, Márcia R.S. Andrade Neto, Valter Ferreira de Silva, Luis Francisco Rocha Vieira, Pedro Paulo Ribeiro Pohlit, Adrian Martin
author2Str	Coelho Cavalcanti, Bruno Amorim, Rodrigo C.N. Lucena, Jorcilene F. Quadros, Dulcimar S. Tadei, Wanderli Pedro Montenegro, Raquel Carvalho Costa-Lotufo, Leticia Veras Pessoa, Cláudia do Ó. Moraes, Manœl Odorico de Nunomura, Rita de Cássia Saraiva Nunomura, Sergio Massayoshi Melo, Márcia R.S. Andrade Neto, Valter Ferreira de Silva, Luis Francisco Rocha Vieira, Pedro Paulo Ribeiro Pohlit, Adrian Martin
title	Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)
title_short	Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)
title_full	Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)
title_fullStr	Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)
title_full_unstemmed	Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)
title_sort	biological activity of neosergeolide and isobrucein b (and two semi-synthetic derivatives) isolated from the amazonian medicinal plant picrolemma sprucei (simaroubaceae)
publisher	Memórias do Instituto Oswaldo Cruz
publishDate	2020
url	https://repositorio.inpa.gov.br/handle/1/14515
_version_	1787144531792101376
score	11.755432

Biological activity of neosergeolide and isobrucein B (and two semi-synthetic derivatives) isolated from the Amazonian medicinal plant Picrolemma sprucei (Simaroubaceae)

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