NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462

Autores
Li, Chun Shun; Sarotti, Ariel Marcelo; Huang, Peng; Dang, Uyen T.; Hurdle, Julian G.; Kondratyuk, Tamara P.; Pezzuto, J. M.; Turkson, James Turkson; Cao, Shugeng
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
LC-UV/MS-based metabolomic analysis of the Hawaiian endophytic fungus Paraphaeosphaeria neglecta FT462 led to the identification of four unique mercaptolactated γ-pyranol-γ-lactams, paraphaeosphaerides E-H (1-4) together with one γ-lactone (5) and the methyl ester of compound 2 (11). The structures of the new compounds (1-5 and 11) were elucidated through the analysis of HRMS and NMR spectroscopic data. The absolute configuration was determined by chemical reactions with sodium borohydride, hydrogen peroxide, α-methoxy-α-(trifluoromethyl)phenylacetyl chlorides (Mosher reagents), and DP4 + NMR calculations. All the compounds were tested against STAT3, A2780 and A2780cisR cancer cell lines, E. coli JW2496, and NF-κB. Compounds 1 and 3 strongly inhibited NF-κB with IC50 values of 7.1 and 1.5 μM, respectively.
Fil: Li, Chun Shun. University of Hawai'i at Hilo; Estados Unidos
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Huang, Peng. University of Hawai'i at Hilo; Estados Unidos. Anhui University of Chinese Medicine; China
Fil: Dang, Uyen T.. Texas A&M University; Estados Unidos
Fil: Hurdle, Julian G.. Texas A&M University; Estados Unidos
Fil: Kondratyuk, Tamara P.. University of Hawai'i at Hilo; Estados Unidos
Fil: Pezzuto, J. M.. University of Hawai'i at Hilo; Estados Unidos. Arnold & Marie Schwartz College of Pharmacy and Health Sciences; Estados Unidos
Fil: Turkson, James Turkson. University of Hawai'i; Estados Unidos
Fil: Cao, Shugeng. University of Hawai'i at Hilo; Estados Unidos
Materia
NF-KB Inhibitors
Pyranol lactams
DP4+
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/63876
Acceder
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repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462Li, Chun ShunSarotti, Ariel MarceloHuang, PengDang, Uyen T.Hurdle, Julian G.Kondratyuk, Tamara P.Pezzuto, J. M.Turkson, James TurksonCao, ShugengNF-KB InhibitorsPyranol lactamsDP4+https://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1LC-UV/MS-based metabolomic analysis of the Hawaiian endophytic fungus Paraphaeosphaeria neglecta FT462 led to the identification of four unique mercaptolactated γ-pyranol-γ-lactams, paraphaeosphaerides E-H (1-4) together with one γ-lactone (5) and the methyl ester of compound 2 (11). The structures of the new compounds (1-5 and 11) were elucidated through the analysis of HRMS and NMR spectroscopic data. The absolute configuration was determined by chemical reactions with sodium borohydride, hydrogen peroxide, α-methoxy-α-(trifluoromethyl)phenylacetyl chlorides (Mosher reagents), and DP4 + NMR calculations. All the compounds were tested against STAT3, A2780 and A2780cisR cancer cell lines, E. coli JW2496, and NF-κB. Compounds 1 and 3 strongly inhibited NF-κB with IC50 values of 7.1 and 1.5 μM, respectively.Fil: Li, Chun Shun. University of Hawai'i at Hilo; Estados UnidosFil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; ArgentinaFil: Huang, Peng. University of Hawai'i at Hilo; Estados Unidos. Anhui University of Chinese Medicine; ChinaFil: Dang, Uyen T.. Texas A&M University; Estados UnidosFil: Hurdle, Julian G.. Texas A&M University; Estados UnidosFil: Kondratyuk, Tamara P.. University of Hawai'i at Hilo; Estados UnidosFil: Pezzuto, J. M.. University of Hawai'i at Hilo; Estados Unidos. Arnold & Marie Schwartz College of Pharmacy and Health Sciences; Estados UnidosFil: Turkson, James Turkson. University of Hawai'i; Estados UnidosFil: Cao, Shugeng. University of Hawai'i at Hilo; Estados UnidosNature Publishing Group2017-12info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/63876Li, Chun Shun; Sarotti, Ariel Marcelo; Huang, Peng; Dang, Uyen T.; Hurdle, Julian G.; et al.; NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462; Nature Publishing Group; Scientific Reports; 7; 1; 12-2017; 1-102045-2322CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1038/s41598-017-10537-1info:eu-repo/semantics/altIdentifier/url/https://www.nature.com/articles/s41598-017-10537-1info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:08:38Zoai:ri.conicet.gov.ar:11336/63876instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-03 10:08:38.754CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462
title NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462
spellingShingle NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462
Li, Chun Shun
NF-KB Inhibitors
Pyranol lactams
DP4+
title_short NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462
title_full NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462
title_fullStr NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462
title_full_unstemmed NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462
title_sort NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462
dc.creator.none.fl_str_mv Li, Chun Shun
Sarotti, Ariel Marcelo
Huang, Peng
Dang, Uyen T.
Hurdle, Julian G.
Kondratyuk, Tamara P.
Pezzuto, J. M.
Turkson, James Turkson
Cao, Shugeng
author Li, Chun Shun
author_facet Li, Chun Shun
Sarotti, Ariel Marcelo
Huang, Peng
Dang, Uyen T.
Hurdle, Julian G.
Kondratyuk, Tamara P.
Pezzuto, J. M.
Turkson, James Turkson
Cao, Shugeng
author_role author
author2 Sarotti, Ariel Marcelo
Huang, Peng
Dang, Uyen T.
Hurdle, Julian G.
Kondratyuk, Tamara P.
Pezzuto, J. M.
Turkson, James Turkson
Cao, Shugeng
author2_role author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv NF-KB Inhibitors
Pyranol lactams
DP4+
topic NF-KB Inhibitors
Pyranol lactams
DP4+
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv LC-UV/MS-based metabolomic analysis of the Hawaiian endophytic fungus Paraphaeosphaeria neglecta FT462 led to the identification of four unique mercaptolactated γ-pyranol-γ-lactams, paraphaeosphaerides E-H (1-4) together with one γ-lactone (5) and the methyl ester of compound 2 (11). The structures of the new compounds (1-5 and 11) were elucidated through the analysis of HRMS and NMR spectroscopic data. The absolute configuration was determined by chemical reactions with sodium borohydride, hydrogen peroxide, α-methoxy-α-(trifluoromethyl)phenylacetyl chlorides (Mosher reagents), and DP4 + NMR calculations. All the compounds were tested against STAT3, A2780 and A2780cisR cancer cell lines, E. coli JW2496, and NF-κB. Compounds 1 and 3 strongly inhibited NF-κB with IC50 values of 7.1 and 1.5 μM, respectively.
Fil: Li, Chun Shun. University of Hawai'i at Hilo; Estados Unidos
Fil: Sarotti, Ariel Marcelo. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario. Instituto de Química Rosario. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Instituto de Química Rosario; Argentina
Fil: Huang, Peng. University of Hawai'i at Hilo; Estados Unidos. Anhui University of Chinese Medicine; China
Fil: Dang, Uyen T.. Texas A&M University; Estados Unidos
Fil: Hurdle, Julian G.. Texas A&M University; Estados Unidos
Fil: Kondratyuk, Tamara P.. University of Hawai'i at Hilo; Estados Unidos
Fil: Pezzuto, J. M.. University of Hawai'i at Hilo; Estados Unidos. Arnold & Marie Schwartz College of Pharmacy and Health Sciences; Estados Unidos
Fil: Turkson, James Turkson. University of Hawai'i; Estados Unidos
Fil: Cao, Shugeng. University of Hawai'i at Hilo; Estados Unidos
description LC-UV/MS-based metabolomic analysis of the Hawaiian endophytic fungus Paraphaeosphaeria neglecta FT462 led to the identification of four unique mercaptolactated γ-pyranol-γ-lactams, paraphaeosphaerides E-H (1-4) together with one γ-lactone (5) and the methyl ester of compound 2 (11). The structures of the new compounds (1-5 and 11) were elucidated through the analysis of HRMS and NMR spectroscopic data. The absolute configuration was determined by chemical reactions with sodium borohydride, hydrogen peroxide, α-methoxy-α-(trifluoromethyl)phenylacetyl chlorides (Mosher reagents), and DP4 + NMR calculations. All the compounds were tested against STAT3, A2780 and A2780cisR cancer cell lines, E. coli JW2496, and NF-κB. Compounds 1 and 3 strongly inhibited NF-κB with IC50 values of 7.1 and 1.5 μM, respectively.
publishDate 2017
dc.date.none.fl_str_mv 2017-12
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/63876
Li, Chun Shun; Sarotti, Ariel Marcelo; Huang, Peng; Dang, Uyen T.; Hurdle, Julian G.; et al.; NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462; Nature Publishing Group; Scientific Reports; 7; 1; 12-2017; 1-10
2045-2322
CONICET Digital
CONICET
url http://hdl.handle.net/11336/63876
identifier_str_mv Li, Chun Shun; Sarotti, Ariel Marcelo; Huang, Peng; Dang, Uyen T.; Hurdle, Julian G.; et al.; NF-κB inhibitors, unique γ-pyranol-γ-lactams with sulfide and sulfoxide moieties from Hawaiian plant Lycopodiella cernua derived fungus Paraphaeosphaeria neglecta FT462; Nature Publishing Group; Scientific Reports; 7; 1; 12-2017; 1-10
2045-2322
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1038/s41598-017-10537-1
info:eu-repo/semantics/altIdentifier/url/https://www.nature.com/articles/s41598-017-10537-1
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Nature Publishing Group
publisher.none.fl_str_mv Nature Publishing Group
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.13397

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