Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4

Detalhes bibliográficos
Autor(a) principal: César, Thaïs B.
Data de Publicação: 2009
Outros Autores: Manthey, John A., Myung, Kyung
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Institucional da UNESP
Texto Completo: http://dx.doi.org/10.1021/np900266m
http://hdl.handle.net/11449/219526
Resumo: A new cyclic acetal (1) of marmin (6′,7′-dihydroxy-7- geranyloxycoumarin), two new cyclic acetals (5, 6) of 6′,7′- dihydroxybergamottin, and the known compounds marmin (2), 7-geranyloxycoumarin (3), bergamottin (4), and 6′,7′-dihydroxybergamottin (7) were isolated from grapefruit peel oil. All compounds were tested for inhibitory activity against intestinal cytochrome P450 3A4, an enzyme involved in the grapefruit/drug interactions in humans. Coumarins (1-3) exhibited negligible inhibitory activity, while the furanocoumarins (4-7) showed potent in vitro inhibitory activity with IC50 values of 2.42, 0.13, 0.27, and 1.58 μM, respectively.
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spelling Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4A new cyclic acetal (1) of marmin (6′,7′-dihydroxy-7- geranyloxycoumarin), two new cyclic acetals (5, 6) of 6′,7′- dihydroxybergamottin, and the known compounds marmin (2), 7-geranyloxycoumarin (3), bergamottin (4), and 6′,7′-dihydroxybergamottin (7) were isolated from grapefruit peel oil. All compounds were tested for inhibitory activity against intestinal cytochrome P450 3A4, an enzyme involved in the grapefruit/drug interactions in humans. Coumarins (1-3) exhibited negligible inhibitory activity, while the furanocoumarins (4-7) showed potent in vitro inhibitory activity with IC50 values of 2.42, 0.13, 0.27, and 1.58 μM, respectively.School of Pharmaceutical Sciences University of São Paulo State, AraraquaraU.S. Citrus and Subtropical Products Laboratory USDA-Agricultural Research Service-South Atlantic Area, Winter Haven, FL 33881Universidade de São Paulo (USP)USDA-Agricultural Research Service-South Atlantic AreaCésar, Thaïs B.Manthey, John A.Myung, Kyung2022-04-28T18:56:07Z2022-04-28T18:56:07Z2009-09-25info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article1702-1704http://dx.doi.org/10.1021/np900266mJournal of Natural Products, v. 72, n. 9, p. 1702-1704, 2009.0163-3864http://hdl.handle.net/11449/21952610.1021/np900266m2-s2.0-70349518908Scopusreponame:Repositório Institucional da UNESPinstname:Universidade Estadual Paulista (UNESP)instacron:UNESPengJournal of Natural Productsinfo:eu-repo/semantics/openAccess2022-04-28T18:56:07Zoai:repositorio.unesp.br:11449/219526Repositório InstitucionalPUBhttp://repositorio.unesp.br/oai/requestopendoar:29462024-08-05T17:20:18.585206Repositório Institucional da UNESP - Universidade Estadual Paulista (UNESP)false
dc.title.none.fl_str_mv Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4
title Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4
spellingShingle Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4
César, Thaïs B.
title_short Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4
title_full Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4
title_fullStr Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4
title_full_unstemmed Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4
title_sort Minor furanocoumarins and coumarins in grapefruit peel oil as inhibitors of human cytochrome P450 3A4
author César, Thaïs B.
author_facet César, Thaïs B.
Manthey, John A.
Myung, Kyung
author_role author
author2 Manthey, John A.
Myung, Kyung
author2_role author
author
dc.contributor.none.fl_str_mv Universidade de São Paulo (USP)
USDA-Agricultural Research Service-South Atlantic Area
dc.contributor.author.fl_str_mv César, Thaïs B.
Manthey, John A.
Myung, Kyung
description A new cyclic acetal (1) of marmin (6′,7′-dihydroxy-7- geranyloxycoumarin), two new cyclic acetals (5, 6) of 6′,7′- dihydroxybergamottin, and the known compounds marmin (2), 7-geranyloxycoumarin (3), bergamottin (4), and 6′,7′-dihydroxybergamottin (7) were isolated from grapefruit peel oil. All compounds were tested for inhibitory activity against intestinal cytochrome P450 3A4, an enzyme involved in the grapefruit/drug interactions in humans. Coumarins (1-3) exhibited negligible inhibitory activity, while the furanocoumarins (4-7) showed potent in vitro inhibitory activity with IC50 values of 2.42, 0.13, 0.27, and 1.58 μM, respectively.
publishDate 2009
dc.date.none.fl_str_mv 2009-09-25
2022-04-28T18:56:07Z
2022-04-28T18:56:07Z
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/10.1021/np900266m
Journal of Natural Products, v. 72, n. 9, p. 1702-1704, 2009.
0163-3864
http://hdl.handle.net/11449/219526
10.1021/np900266m
2-s2.0-70349518908
url http://dx.doi.org/10.1021/np900266m
http://hdl.handle.net/11449/219526
identifier_str_mv Journal of Natural Products, v. 72, n. 9, p. 1702-1704, 2009.
0163-3864
10.1021/np900266m
2-s2.0-70349518908
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Journal of Natural Products
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 1702-1704
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_ 1808128793493110784

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