Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities

Autores
Cai, You-Sheng; Sarotti, Ariel Marcelo; Gündisch, Daniela; Kondratyuk, Tamara P.; Pezzuto, John; Turkson, James; Cao, Shugeng
Año de publicación
2017
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Two new compounds heliotropiumides A (1) and B (2), phenolamides each with an uncommon carbamoyl putrescine moiety, were isolated from the seeds of a naturalized Hawaiian higher plant, Heliotropium foertherianum Diane & Hilger in the borage family, which is widely used for the treatment of ciguatera fish poisoning. The structures of compounds 1 and 2 were characterized based on MS spectroscopic and NMR analysis, and DP4+ calculations. The absolute configuration (AC) of compound 1 was determined by comparison of its optical rotation with those reported in literature. Compound 2 showed inhibition against NF-κB with an IC50 value of 36 μM.
Fil: Cai, You-Sheng. University of Hawaii at Hilo; Estados Unidos. Wuhan University; China
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: Gündisch, Daniela. University of Hawaii at Hilo; Estados Unidos
Fil: Kondratyuk, Tamara P.. University of Hawaii at Hilo; Estados Unidos
Fil: Pezzuto, John. Long Island University; Estados Unidos. University of Hawaii Cancer Center; Estados Unidos
Fil: Turkson, James. University of Hawaii Cancer Center; Estados Unidos
Fil: Cao, Shugeng. University of Hawaii at Hilo; Estados Unidos
Materia
Heliotropium Foertherianum
Heliotropiumides
Nf-ΚB
Nmr Dp4+ Calculation
Optical Rotation
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:11336/53189
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/53189
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activitiesCai, You-ShengSarotti, Ariel MarceloGündisch, DanielaKondratyuk, Tamara P.Pezzuto, JohnTurkson, JamesCao, ShugengHeliotropium FoertherianumHeliotropiumidesNf-ΚBNmr Dp4+ CalculationOptical Rotationhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Two new compounds heliotropiumides A (1) and B (2), phenolamides each with an uncommon carbamoyl putrescine moiety, were isolated from the seeds of a naturalized Hawaiian higher plant, Heliotropium foertherianum Diane & Hilger in the borage family, which is widely used for the treatment of ciguatera fish poisoning. The structures of compounds 1 and 2 were characterized based on MS spectroscopic and NMR analysis, and DP4+ calculations. The absolute configuration (AC) of compound 1 was determined by comparison of its optical rotation with those reported in literature. Compound 2 showed inhibition against NF-κB with an IC50 value of 36 μM.Fil: Cai, You-Sheng. University of Hawaii at Hilo; Estados Unidos. Wuhan University; ChinaFil: 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: Gündisch, Daniela. University of Hawaii at Hilo; Estados UnidosFil: Kondratyuk, Tamara P.. University of Hawaii at Hilo; Estados UnidosFil: Pezzuto, John. Long Island University; Estados Unidos. University of Hawaii Cancer Center; Estados UnidosFil: Turkson, James. University of Hawaii Cancer Center; Estados UnidosFil: Cao, Shugeng. University of Hawaii at Hilo; Estados UnidosPergamon-Elsevier Science Ltd2017-09info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/53189Cai, You-Sheng; Sarotti, Ariel Marcelo; Gündisch, Daniela; Kondratyuk, Tamara P.; Pezzuto, John; et al.; Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities; Pergamon-Elsevier Science Ltd; Biorganic and Medicinal Chemistry Letters; 27; 20; 9-2017; 4630-46340960-894XCONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2017.09.021info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0960894X17309162info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T09:53:15Zoai:ri.conicet.gov.ar:11336/53189instacron: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 09:53:15.78CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities
title Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities
spellingShingle Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities
Cai, You-Sheng
Heliotropium Foertherianum
Heliotropiumides
Nf-ΚB
Nmr Dp4+ Calculation
Optical Rotation
title_short Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities
title_full Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities
title_fullStr Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities
title_full_unstemmed Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities
title_sort Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities
dc.creator.none.fl_str_mv Cai, You-Sheng
Sarotti, Ariel Marcelo
Gündisch, Daniela
Kondratyuk, Tamara P.
Pezzuto, John
Turkson, James
Cao, Shugeng
author Cai, You-Sheng
author_facet Cai, You-Sheng
Sarotti, Ariel Marcelo
Gündisch, Daniela
Kondratyuk, Tamara P.
Pezzuto, John
Turkson, James
Cao, Shugeng
author_role author
author2 Sarotti, Ariel Marcelo
Gündisch, Daniela
Kondratyuk, Tamara P.
Pezzuto, John
Turkson, James
Cao, Shugeng
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Heliotropium Foertherianum
Heliotropiumides
Nf-ΚB
Nmr Dp4+ Calculation
Optical Rotation
topic Heliotropium Foertherianum
Heliotropiumides
Nf-ΚB
Nmr Dp4+ Calculation
Optical Rotation
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Two new compounds heliotropiumides A (1) and B (2), phenolamides each with an uncommon carbamoyl putrescine moiety, were isolated from the seeds of a naturalized Hawaiian higher plant, Heliotropium foertherianum Diane & Hilger in the borage family, which is widely used for the treatment of ciguatera fish poisoning. The structures of compounds 1 and 2 were characterized based on MS spectroscopic and NMR analysis, and DP4+ calculations. The absolute configuration (AC) of compound 1 was determined by comparison of its optical rotation with those reported in literature. Compound 2 showed inhibition against NF-κB with an IC50 value of 36 μM.
Fil: Cai, You-Sheng. University of Hawaii at Hilo; Estados Unidos. Wuhan University; China
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: Gündisch, Daniela. University of Hawaii at Hilo; Estados Unidos
Fil: Kondratyuk, Tamara P.. University of Hawaii at Hilo; Estados Unidos
Fil: Pezzuto, John. Long Island University; Estados Unidos. University of Hawaii Cancer Center; Estados Unidos
Fil: Turkson, James. University of Hawaii Cancer Center; Estados Unidos
Fil: Cao, Shugeng. University of Hawaii at Hilo; Estados Unidos
description Two new compounds heliotropiumides A (1) and B (2), phenolamides each with an uncommon carbamoyl putrescine moiety, were isolated from the seeds of a naturalized Hawaiian higher plant, Heliotropium foertherianum Diane & Hilger in the borage family, which is widely used for the treatment of ciguatera fish poisoning. The structures of compounds 1 and 2 were characterized based on MS spectroscopic and NMR analysis, and DP4+ calculations. The absolute configuration (AC) of compound 1 was determined by comparison of its optical rotation with those reported in literature. Compound 2 showed inhibition against NF-κB with an IC50 value of 36 μM.
publishDate 2017
dc.date.none.fl_str_mv 2017-09
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/11336/53189
Cai, You-Sheng; Sarotti, Ariel Marcelo; Gündisch, Daniela; Kondratyuk, Tamara P.; Pezzuto, John; et al.; Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities; Pergamon-Elsevier Science Ltd; Biorganic and Medicinal Chemistry Letters; 27; 20; 9-2017; 4630-4634
0960-894X
CONICET Digital
CONICET
url http://hdl.handle.net/11336/53189
identifier_str_mv Cai, You-Sheng; Sarotti, Ariel Marcelo; Gündisch, Daniela; Kondratyuk, Tamara P.; Pezzuto, John; et al.; Heliotropiumides A and B, new phenolamides with N-carbamoyl putrescine moiety from Heliotropium foertherianum collected in Hawaii and their biological activities; Pergamon-Elsevier Science Ltd; Biorganic and Medicinal Chemistry Letters; 27; 20; 9-2017; 4630-4634
0960-894X
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1016/j.bmcl.2017.09.021
info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0960894X17309162
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 Pergamon-Elsevier Science Ltd
publisher.none.fl_str_mv Pergamon-Elsevier Science Ltd
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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