Chemodiversity and Anti-Leukemia Effect of Metabolites from <i>Penicillium setosum</i> CMLD 18

<i>Penicillium setosum</i> represents a <i>Penicillium</i> species recently described, with little up-to-date information about its metabolic and biological potential. Due to this scenario, we performed chemical and biological studies of <i>P. setosum</i> CMLD18,...

Full description

Bibliographic Details
Main Authors: Ana Calheiros de Carvalho, Cauê Santos Lima, Heron Fernandes Vieira Torquato, André Tarsis Domiciano, Sebastião da Cruz Silva, Lucas Magalhães de Abreu, Miriam Uemi, Edgar Julian Paredes-Gamero, Paulo Cezar Vieira, Thiago André Moura Veiga, Lívia Soman de Medeiros
Format: Article
Language:English
Published: MDPI AG 2022-12-01
Series:Metabolites
Subjects:
Online Access:https://www.mdpi.com/2218-1989/13/1/23
_version_ 1797438833415946240
author Ana Calheiros de Carvalho
Cauê Santos Lima
Heron Fernandes Vieira Torquato
André Tarsis Domiciano
Sebastião da Cruz Silva
Lucas Magalhães de Abreu
Miriam Uemi
Edgar Julian Paredes-Gamero
Paulo Cezar Vieira
Thiago André Moura Veiga
Lívia Soman de Medeiros
author_facet Ana Calheiros de Carvalho
Cauê Santos Lima
Heron Fernandes Vieira Torquato
André Tarsis Domiciano
Sebastião da Cruz Silva
Lucas Magalhães de Abreu
Miriam Uemi
Edgar Julian Paredes-Gamero
Paulo Cezar Vieira
Thiago André Moura Veiga
Lívia Soman de Medeiros
author_sort Ana Calheiros de Carvalho
collection DOAJ
description <i>Penicillium setosum</i> represents a <i>Penicillium</i> species recently described, with little up-to-date information about its metabolic and biological potential. Due to this scenario, we performed chemical and biological studies of <i>P. setosum</i> CMLD18, a strain isolated from <i>Swinglea glutinosa</i> (Rutaceae). HRMS-MS guided dereplication strategies and anti-leukemia assays conducted the isolation and characterization of six compounds after several chromatographic procedures: 2-chloroemodic acid (<b>2</b>), 2-chloro-1,3,8-trihydroxy-6- (hydroxymethyl)-anthraquinone (<b>7</b>), 7-chloroemodin (<b>8</b>), bisdethiobis(methylthio)acetylaranotine (<b>9</b>), fellutanine C (<b>10</b>), and 4-methyl-5,6-diihydro-2H-pyran-2-one (<b>15</b>). From the assayed metabolites, (<b>10</b>) induced cellular death against Kasumi-1, a human leukemia cell line, as well as good selectivity for it, displaying promising cytotoxic activity. Here, the correct NMR signal assignments for (<b>9</b>) are also described. Therefore, this work highlights more detailed knowledge about the <i>P. setosum</i> chemical profile as well as its biological potential, offering prospects for obtaining natural products with anti-leukemia capabilities.
first_indexed 2024-03-09T11:44:00Z
format Article
id doaj.art-f0c070b74cb14d2fa967a61c21604444
institution Directory Open Access Journal
issn 2218-1989
language English
last_indexed 2024-03-09T11:44:00Z
publishDate 2022-12-01
publisher MDPI AG
record_format Article
series Metabolites
spelling doaj.art-f0c070b74cb14d2fa967a61c216044442023-11-30T23:27:46ZengMDPI AGMetabolites2218-19892022-12-011312310.3390/metabo13010023Chemodiversity and Anti-Leukemia Effect of Metabolites from <i>Penicillium setosum</i> CMLD 18Ana Calheiros de Carvalho0Cauê Santos Lima1Heron Fernandes Vieira Torquato2André Tarsis Domiciano3Sebastião da Cruz Silva4Lucas Magalhães de Abreu5Miriam Uemi6Edgar Julian Paredes-Gamero7Paulo Cezar Vieira8Thiago André Moura Veiga9Lívia Soman de Medeiros10Programa de Pós-Graduação em Biologia Química, Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Diadema 09972-270, BrazilDepartamento de Bioquímica, Universidade Federal de São Paulo, São Paulo 04044-020, BrazilFaculdade de Farmácia, Centro Universitário Braz Cubas, Mogi das Cruzes 08773-380, BrazilDepartamento de Bioquímica, Universidade Federal de São Paulo, São Paulo 04044-020, BrazilInstituto de Ciências Exatas, Universidade Federal do Sul e Sudeste do Pará, Marabá 68505-080, BrazilDepartamento de Fitopatologia, Universidade Federal de Viçosa, Viçosa 36570-900, BrazilDepartamento de Química, Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Diadema 09972-270, BrazilFaculdade de Ciências Farmacêuticas, Alimentos e Nutrição, Universidade Federal de Mato Grosso do Sul, Campo Grande 79070-900, BrazilNPPNS, Department of BioMolecular Sciences, Faculty of Pharmaceutical Sciences of Ribeirao Preto, University of Sao Paulo, Ribeirao Preto 14040-903, BrazilDepartamento de Química, Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Diadema 09972-270, BrazilDepartamento de Química, Instituto de Ciências Ambientais, Químicas e Farmacêuticas, Universidade Federal de São Paulo, Diadema 09972-270, Brazil<i>Penicillium setosum</i> represents a <i>Penicillium</i> species recently described, with little up-to-date information about its metabolic and biological potential. Due to this scenario, we performed chemical and biological studies of <i>P. setosum</i> CMLD18, a strain isolated from <i>Swinglea glutinosa</i> (Rutaceae). HRMS-MS guided dereplication strategies and anti-leukemia assays conducted the isolation and characterization of six compounds after several chromatographic procedures: 2-chloroemodic acid (<b>2</b>), 2-chloro-1,3,8-trihydroxy-6- (hydroxymethyl)-anthraquinone (<b>7</b>), 7-chloroemodin (<b>8</b>), bisdethiobis(methylthio)acetylaranotine (<b>9</b>), fellutanine C (<b>10</b>), and 4-methyl-5,6-diihydro-2H-pyran-2-one (<b>15</b>). From the assayed metabolites, (<b>10</b>) induced cellular death against Kasumi-1, a human leukemia cell line, as well as good selectivity for it, displaying promising cytotoxic activity. Here, the correct NMR signal assignments for (<b>9</b>) are also described. Therefore, this work highlights more detailed knowledge about the <i>P. setosum</i> chemical profile as well as its biological potential, offering prospects for obtaining natural products with anti-leukemia capabilities.https://www.mdpi.com/2218-1989/13/1/23<i>Penicillium setosum</i><i>Swinglea glutinosa</i>dereplicationleukemia
spellingShingle Ana Calheiros de Carvalho
Cauê Santos Lima
Heron Fernandes Vieira Torquato
André Tarsis Domiciano
Sebastião da Cruz Silva
Lucas Magalhães de Abreu
Miriam Uemi
Edgar Julian Paredes-Gamero
Paulo Cezar Vieira
Thiago André Moura Veiga
Lívia Soman de Medeiros
Chemodiversity and Anti-Leukemia Effect of Metabolites from <i>Penicillium setosum</i> CMLD 18
Metabolites
<i>Penicillium setosum</i>
<i>Swinglea glutinosa</i>
dereplication
leukemia
title Chemodiversity and Anti-Leukemia Effect of Metabolites from <i>Penicillium setosum</i> CMLD 18
title_full Chemodiversity and Anti-Leukemia Effect of Metabolites from <i>Penicillium setosum</i> CMLD 18
title_fullStr Chemodiversity and Anti-Leukemia Effect of Metabolites from <i>Penicillium setosum</i> CMLD 18
title_full_unstemmed Chemodiversity and Anti-Leukemia Effect of Metabolites from <i>Penicillium setosum</i> CMLD 18
title_short Chemodiversity and Anti-Leukemia Effect of Metabolites from <i>Penicillium setosum</i> CMLD 18
title_sort chemodiversity and anti leukemia effect of metabolites from i penicillium setosum i cmld 18
topic <i>Penicillium setosum</i>
<i>Swinglea glutinosa</i>
dereplication
leukemia
url https://www.mdpi.com/2218-1989/13/1/23
work_keys_str_mv AT anacalheirosdecarvalho chemodiversityandantileukemiaeffectofmetabolitesfromipenicilliumsetosumicmld18
AT cauesantoslima chemodiversityandantileukemiaeffectofmetabolitesfromipenicilliumsetosumicmld18
AT heronfernandesvieiratorquato chemodiversityandantileukemiaeffectofmetabolitesfromipenicilliumsetosumicmld18
AT andretarsisdomiciano chemodiversityandantileukemiaeffectofmetabolitesfromipenicilliumsetosumicmld18
AT sebastiaodacruzsilva chemodiversityandantileukemiaeffectofmetabolitesfromipenicilliumsetosumicmld18
AT lucasmagalhaesdeabreu chemodiversityandantileukemiaeffectofmetabolitesfromipenicilliumsetosumicmld18
AT miriamuemi chemodiversityandantileukemiaeffectofmetabolitesfromipenicilliumsetosumicmld18
AT edgarjulianparedesgamero chemodiversityandantileukemiaeffectofmetabolitesfromipenicilliumsetosumicmld18
AT paulocezarvieira chemodiversityandantileukemiaeffectofmetabolitesfromipenicilliumsetosumicmld18
AT thiagoandremouraveiga chemodiversityandantileukemiaeffectofmetabolitesfromipenicilliumsetosumicmld18
AT liviasomandemedeiros chemodiversityandantileukemiaeffectofmetabolitesfromipenicilliumsetosumicmld18