Absolute Configuration and Antileishmanial Activity of (–)-Cyclocolorenone Isolated from Duguetia lanceolata (Annonaceae)
Autor(a) principal: | |
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Data de Publicação: | 2022 |
Outros Autores: | , , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Institucional da UNESP |
Texto Completo: | http://dx.doi.org/10.2174/1568026622666220707095718 http://hdl.handle.net/11449/240688 |
Resumo: | Background: The fractionation of the n-hexane phase of the EtOH extract from the leaves of Duguetia lanceolata (Annonaceae) led to the identification of the sesquiterpene (–)-cyclocolorenone. Objectives: Chemical characterization, including determination of the absolute stereochemistry, and in vitro evaluation of antileishmanial activity of the sesquiterpene (–)-cyclocolorenone, isolated from D. lanceolata, were carried out. Methods: (–)-Cyclocolorenone was isolated from D. lanceolata leaves using different chromato-graphic steps and its structure was defined by analysis of NMR and ESI-HRMS data. Additionally, the absolute configuration of (–)-cyclocolorenone was ambiguously assigned by means of vibrational circular dichroism (VCD). Antileishmanial activity of (–)-cyclocolorenone was evaluated on promastigote and amastigote forms of Leishmania (Leishmania) amazonensis. The integrity of the cell membrane of L. (L.) amazonensis was analyzed using the SYTOX green probe. Results: (–)-(1R,6S,7R,10R)-Cyclocolorenone displayed activity against promastigotes and amastigotes forms of L. (L.) amazonensis with IC50 of 4.54 and 28.44 μM, respectively. Furthermore, this compound was non-toxic in J774 macrophage cells (CC50 > 458.71 μM) with a selectivity index > 100 (promastigotes) and > 32.2 (amastigotes). Additionally, (–)-cyclocolorenone was observed to target the parasite cell membrane. Conclusion: Obtained data suggested that (–)-cyclocolorenone, in which absolute configuration was determined, can be considered as a scaffold for the development of new drugs for the treatment of leishmaniasis. |
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Absolute Configuration and Antileishmanial Activity of (–)-Cyclocolorenone Isolated from Duguetia lanceolata (Annonaceae)(–)-CyclocolorenoneAntileishmanial activityCell membraneDuguetia lanceolataMacrophage cellsVCDBackground: The fractionation of the n-hexane phase of the EtOH extract from the leaves of Duguetia lanceolata (Annonaceae) led to the identification of the sesquiterpene (–)-cyclocolorenone. Objectives: Chemical characterization, including determination of the absolute stereochemistry, and in vitro evaluation of antileishmanial activity of the sesquiterpene (–)-cyclocolorenone, isolated from D. lanceolata, were carried out. Methods: (–)-Cyclocolorenone was isolated from D. lanceolata leaves using different chromato-graphic steps and its structure was defined by analysis of NMR and ESI-HRMS data. Additionally, the absolute configuration of (–)-cyclocolorenone was ambiguously assigned by means of vibrational circular dichroism (VCD). Antileishmanial activity of (–)-cyclocolorenone was evaluated on promastigote and amastigote forms of Leishmania (Leishmania) amazonensis. The integrity of the cell membrane of L. (L.) amazonensis was analyzed using the SYTOX green probe. Results: (–)-(1R,6S,7R,10R)-Cyclocolorenone displayed activity against promastigotes and amastigotes forms of L. (L.) amazonensis with IC50 of 4.54 and 28.44 μM, respectively. Furthermore, this compound was non-toxic in J774 macrophage cells (CC50 > 458.71 μM) with a selectivity index > 100 (promastigotes) and > 32.2 (amastigotes). Additionally, (–)-cyclocolorenone was observed to target the parasite cell membrane. Conclusion: Obtained data suggested that (–)-cyclocolorenone, in which absolute configuration was determined, can be considered as a scaffold for the development of new drugs for the treatment of leishmaniasis.Coordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)Fundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)Conselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)Instituto de Ciências Ambientais Químicas e Farmacêuticas Universidade Federal de São PauloInstituto de Biociências Universidade Estadual PaulistaInstitute for Advanced Studies of Ocean UNESPDepartamento de Patologia Faculdade de Medicina da Universidade de São PauloCentro de Ciências Naturais e Humanas Universidade Federal do ABCInstituto de Química Universidade Federal de AlfenasInstituto de Química Universidade Federal FluminenseInstituto de Ciência e Tecnologia Universidade Federal de São PauloInstituto de Biociências Universidade Estadual PaulistaInstitute for Advanced Studies of Ocean UNESPCAPES: 001FAPESP: 2016/ 24985-4FAPESP: 2018/24077-6FAPESP: 2019/22319-5FAPESP: 2021/02789-7CNPq: 431978/2018-2Universidade Federal de São Paulo (UNIFESP)Universidade Estadual Paulista (UNESP)Universidade de São Paulo (USP)Universidade Federal do ABC (UFABC)Universidade Federal de AlfenasUniversidade Federal Fluminense (UFF)Monteiro, JacksonPassero, Luiz Felipe D. [UNESP]Jesus, Jéssica A.Laurenti, Márcia D.Lago, João H. G.Soares, Marisi G.Batista, Andrea N. L.Batista, João M.Sartorelli, Patricia2023-03-01T20:28:23Z2023-03-01T20:28:23Z2022-07-01info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article1626-1633http://dx.doi.org/10.2174/1568026622666220707095718Current Topics in Medicinal Chemistry, v. 22, n. 19, p. 1626-1633, 2022.1873-42941568-0266http://hdl.handle.net/11449/24068810.2174/15680266226662207070957182-s2.0-85136303283Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengCurrent Topics in Medicinal Chemistryinfo:eu-repo/semantics/openAccess2023-03-01T20:28:23Zoai:repositorio.unesp.br:11449/240688Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T18:59:01.812829Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false |
dc.title.none.fl_str_mv |
Absolute Configuration and Antileishmanial Activity of (–)-Cyclocolorenone Isolated from Duguetia lanceolata (Annonaceae) |
title |
Absolute Configuration and Antileishmanial Activity of (–)-Cyclocolorenone Isolated from Duguetia lanceolata (Annonaceae) |
spellingShingle |
Absolute Configuration and Antileishmanial Activity of (–)-Cyclocolorenone Isolated from Duguetia lanceolata (Annonaceae) Monteiro, Jackson (–)-Cyclocolorenone Antileishmanial activity Cell membrane Duguetia lanceolata Macrophage cells VCD |
title_short |
Absolute Configuration and Antileishmanial Activity of (–)-Cyclocolorenone Isolated from Duguetia lanceolata (Annonaceae) |
title_full |
Absolute Configuration and Antileishmanial Activity of (–)-Cyclocolorenone Isolated from Duguetia lanceolata (Annonaceae) |
title_fullStr |
Absolute Configuration and Antileishmanial Activity of (–)-Cyclocolorenone Isolated from Duguetia lanceolata (Annonaceae) |
title_full_unstemmed |
Absolute Configuration and Antileishmanial Activity of (–)-Cyclocolorenone Isolated from Duguetia lanceolata (Annonaceae) |
title_sort |
Absolute Configuration and Antileishmanial Activity of (–)-Cyclocolorenone Isolated from Duguetia lanceolata (Annonaceae) |
author |
Monteiro, Jackson |
author_facet |
Monteiro, Jackson Passero, Luiz Felipe D. [UNESP] Jesus, Jéssica A. Laurenti, Márcia D. Lago, João H. G. Soares, Marisi G. Batista, Andrea N. L. Batista, João M. Sartorelli, Patricia |
author_role |
author |
author2 |
Passero, Luiz Felipe D. [UNESP] Jesus, Jéssica A. Laurenti, Márcia D. Lago, João H. G. Soares, Marisi G. Batista, Andrea N. L. Batista, João M. Sartorelli, Patricia |
author2_role |
author author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade Federal de São Paulo (UNIFESP) Universidade Estadual Paulista (UNESP) Universidade de São Paulo (USP) Universidade Federal do ABC (UFABC) Universidade Federal de Alfenas Universidade Federal Fluminense (UFF) |
dc.contributor.author.fl_str_mv |
Monteiro, Jackson Passero, Luiz Felipe D. [UNESP] Jesus, Jéssica A. Laurenti, Márcia D. Lago, João H. G. Soares, Marisi G. Batista, Andrea N. L. Batista, João M. Sartorelli, Patricia |
dc.subject.por.fl_str_mv |
(–)-Cyclocolorenone Antileishmanial activity Cell membrane Duguetia lanceolata Macrophage cells VCD |
topic |
(–)-Cyclocolorenone Antileishmanial activity Cell membrane Duguetia lanceolata Macrophage cells VCD |
description |
Background: The fractionation of the n-hexane phase of the EtOH extract from the leaves of Duguetia lanceolata (Annonaceae) led to the identification of the sesquiterpene (–)-cyclocolorenone. Objectives: Chemical characterization, including determination of the absolute stereochemistry, and in vitro evaluation of antileishmanial activity of the sesquiterpene (–)-cyclocolorenone, isolated from D. lanceolata, were carried out. Methods: (–)-Cyclocolorenone was isolated from D. lanceolata leaves using different chromato-graphic steps and its structure was defined by analysis of NMR and ESI-HRMS data. Additionally, the absolute configuration of (–)-cyclocolorenone was ambiguously assigned by means of vibrational circular dichroism (VCD). Antileishmanial activity of (–)-cyclocolorenone was evaluated on promastigote and amastigote forms of Leishmania (Leishmania) amazonensis. The integrity of the cell membrane of L. (L.) amazonensis was analyzed using the SYTOX green probe. Results: (–)-(1R,6S,7R,10R)-Cyclocolorenone displayed activity against promastigotes and amastigotes forms of L. (L.) amazonensis with IC50 of 4.54 and 28.44 μM, respectively. Furthermore, this compound was non-toxic in J774 macrophage cells (CC50 > 458.71 μM) with a selectivity index > 100 (promastigotes) and > 32.2 (amastigotes). Additionally, (–)-cyclocolorenone was observed to target the parasite cell membrane. Conclusion: Obtained data suggested that (–)-cyclocolorenone, in which absolute configuration was determined, can be considered as a scaffold for the development of new drugs for the treatment of leishmaniasis. |
publishDate |
2022 |
dc.date.none.fl_str_mv |
2022-07-01 2023-03-01T20:28:23Z 2023-03-01T20:28:23Z |
dc.type.status.fl_str_mv |
info:eu-repo/semantics/publishedVersion |
dc.type.driver.fl_str_mv |
info:eu-repo/semantics/article |
format |
article |
status_str |
publishedVersion |
dc.identifier.uri.fl_str_mv |
http://dx.doi.org/10.2174/1568026622666220707095718 Current Topics in Medicinal Chemistry, v. 22, n. 19, p. 1626-1633, 2022. 1873-4294 1568-0266 http://hdl.handle.net/11449/240688 10.2174/1568026622666220707095718 2-s2.0-85136303283 |
url |
http://dx.doi.org/10.2174/1568026622666220707095718 http://hdl.handle.net/11449/240688 |
identifier_str_mv |
Current Topics in Medicinal Chemistry, v. 22, n. 19, p. 1626-1633, 2022. 1873-4294 1568-0266 10.2174/1568026622666220707095718 2-s2.0-85136303283 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Current Topics in Medicinal Chemistry |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
1626-1633 |
dc.source.none.fl_str_mv |
Scopus reponame:Repositório Institucional da UNESP instname:Universidade Estadual Paulista (UNESP) instacron:UNESP |
instname_str |
Universidade Estadual Paulista (UNESP) |
instacron_str |
UNESP |
institution |
UNESP |
reponame_str |
Repositório Institucional da UNESP |
collection |
Repositório Institucional da UNESP |
repository.name.fl_str_mv |
Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP) |
repository.mail.fl_str_mv |
|
_version_ |
1808129007052390400 |