Absolute Configuration and Antileishmanial Activity of (–)-Cyclocolorenone Isolated from Duguetia lanceolata (Annonaceae)

Detalhes bibliográficos
Autor(a) principal: Monteiro, Jackson
Data de Publicação: 2022
Outros Autores: 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
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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spelling 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)
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