Identification, formation, and occurrence of perlolyrine: A β-carboline alkaloid with a furan moiety in foods

β-Carbolines are naturally occurring bioactive alkaloids found in foods and in vivo. This research reports the identification, characterization, mechanism of formation, and occurrence of perlolyrine (1-(5-(hydroxymethyl)furan-2-yl)-9H-pyrido[3,4-b]indole), a β-carboline with a furan moiety. Perlolyr...

Descripción completa

Detalles Bibliográficos
Autores: Herraiz Tomico, Tomás, Peña, Adriana, Salgado, Antonio
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2023
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/341184
Acceso en línea:http://hdl.handle.net/10261/341184
Access Level:acceso abierto
Palabra clave:Perlolyrine
Foods
β-carboline alkaloids
Maillard reaction
Tryptophan 3-deoxyglucosone
Sucrose
Fructose
Glucose
id ES_ebf382facbf424c5cb10cb0b52b7ebec
oai_identifier_str oai:digital.csic.es:10261/341184
network_acronym_str ES
network_name_str España
repository_id_str
spelling Identification, formation, and occurrence of perlolyrine: A β-carboline alkaloid with a furan moiety in foodsHerraiz Tomico, TomásPeña, AdrianaSalgado, AntonioPerlolyrineFoodsβ-carboline alkaloidsMaillard reactionTryptophan 3-deoxyglucosoneSucroseFructoseGlucoseβ-Carbolines are naturally occurring bioactive alkaloids found in foods and in vivo. This research reports the identification, characterization, mechanism of formation, and occurrence of perlolyrine (1-(5-(hydroxymethyl)furan-2-yl)-9H-pyrido[3,4-b]indole), a β-carboline with a furan moiety. Perlolyrine did not arise from l-tryptophan and hydroxymethylfurfural but from the reaction of l-tryptophan with 3-deoxyglucosone, an intermediate of carbohydrate degradation. The mechanism of formation occurs through 3,4-dihydro-β-carboline-3-carboxylic acid intermediates (imines), followed by the oxidation of C1′-OH to ketoimine and oxidative decarboxylation at C-3, along with dehydration and cyclization to afford the β-carboline with a furan moiety. The formation of perlolyrine was favored in acidic conditions and temperatures in the range of 70–110 °C. Perlolyrine occurred in the reactions of tryptophan with carbohydrates. The formation rate from fructose was much higher than from glucose. Sucrose also gave perlolyrine under acidic conditions and heating. Perlolyrine was identified in many foods by HPLC-MS and analyzed by HPLC-fluorescence. It occurred in many processed foods such as tomato products including tomato puree, fried tomato, ketchups, tomato juices, and jams but also in soy sauce, beer, balsamic vinegar, fruit juices, dried fruits, fried onion, and honey. The concentrations ranged from an undetected amount to 3.5 μg/g with the highest average levels found in tomato concentrate (1.9 μg/g) and soy sauce (1.5 μg/mL). The results show that perlolyrine formed during the heating process of foods. It is concluded that perlolyrine is widely present in foods and it is daily ingested in the diet.The authors thank Spanish Government-Feder (projects PDC2022-133269-I00 and PID2021-127833OB-I00) and CSIC (200470E658). A.P. thanks Comunidad de Madrid (CAM) and Fondo Social Europeo-Iniciativa de Empleo Juvenil (YEI) for a Garantia Juvenil contract.Peer reviewedAmerican Chemical SocietyMinisterio de Ciencia, Innovación y Universidades (España)Agencia Estatal de Investigación (España)European CommissionComunidad de MadridConsejo Superior de Investigaciones Científicas (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202320232023info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionapplication/pdfhttp://hdl.handle.net/10261/341184reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/AEI//PDC2022-133269-I00info:eu-repo/grantAgreement/AEI//PID2021-127833OB-I00Herraiz Tomico, Tomás; Peña, Adriana; Salgado, Antonio; 2023; Supporting information: Identification, formation, and occurrence of perlolyrine: A β-carboline alkaloid with a furan moiety in foods [Dataset]; American Chemical Society; https://doi.org/10.1021/acs.jafc.3c03612https://doi.org/10.1021/acs.jafc.3c03612Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3411842026-05-22T06:33:51Z
dc.title.none.fl_str_mv Identification, formation, and occurrence of perlolyrine: A β-carboline alkaloid with a furan moiety in foods
title Identification, formation, and occurrence of perlolyrine: A β-carboline alkaloid with a furan moiety in foods
spellingShingle Identification, formation, and occurrence of perlolyrine: A β-carboline alkaloid with a furan moiety in foods
Herraiz Tomico, Tomás
Perlolyrine
Foods
β-carboline alkaloids
Maillard reaction
Tryptophan 3-deoxyglucosone
Sucrose
Fructose
Glucose
title_short Identification, formation, and occurrence of perlolyrine: A β-carboline alkaloid with a furan moiety in foods
title_full Identification, formation, and occurrence of perlolyrine: A β-carboline alkaloid with a furan moiety in foods
title_fullStr Identification, formation, and occurrence of perlolyrine: A β-carboline alkaloid with a furan moiety in foods
title_full_unstemmed Identification, formation, and occurrence of perlolyrine: A β-carboline alkaloid with a furan moiety in foods
title_sort Identification, formation, and occurrence of perlolyrine: A β-carboline alkaloid with a furan moiety in foods
dc.creator.none.fl_str_mv Herraiz Tomico, Tomás
Peña, Adriana
Salgado, Antonio
author Herraiz Tomico, Tomás
author_facet Herraiz Tomico, Tomás
Peña, Adriana
Salgado, Antonio
author_role author
author2 Peña, Adriana
Salgado, Antonio
author2_role author
author
dc.contributor.none.fl_str_mv Ministerio de Ciencia, Innovación y Universidades (España)
Agencia Estatal de Investigación (España)
European Commission
Comunidad de Madrid
Consejo Superior de Investigaciones Científicas (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Perlolyrine
Foods
β-carboline alkaloids
Maillard reaction
Tryptophan 3-deoxyglucosone
Sucrose
Fructose
Glucose
topic Perlolyrine
Foods
β-carboline alkaloids
Maillard reaction
Tryptophan 3-deoxyglucosone
Sucrose
Fructose
Glucose
description β-Carbolines are naturally occurring bioactive alkaloids found in foods and in vivo. This research reports the identification, characterization, mechanism of formation, and occurrence of perlolyrine (1-(5-(hydroxymethyl)furan-2-yl)-9H-pyrido[3,4-b]indole), a β-carboline with a furan moiety. Perlolyrine did not arise from l-tryptophan and hydroxymethylfurfural but from the reaction of l-tryptophan with 3-deoxyglucosone, an intermediate of carbohydrate degradation. The mechanism of formation occurs through 3,4-dihydro-β-carboline-3-carboxylic acid intermediates (imines), followed by the oxidation of C1′-OH to ketoimine and oxidative decarboxylation at C-3, along with dehydration and cyclization to afford the β-carboline with a furan moiety. The formation of perlolyrine was favored in acidic conditions and temperatures in the range of 70–110 °C. Perlolyrine occurred in the reactions of tryptophan with carbohydrates. The formation rate from fructose was much higher than from glucose. Sucrose also gave perlolyrine under acidic conditions and heating. Perlolyrine was identified in many foods by HPLC-MS and analyzed by HPLC-fluorescence. It occurred in many processed foods such as tomato products including tomato puree, fried tomato, ketchups, tomato juices, and jams but also in soy sauce, beer, balsamic vinegar, fruit juices, dried fruits, fried onion, and honey. The concentrations ranged from an undetected amount to 3.5 μg/g with the highest average levels found in tomato concentrate (1.9 μg/g) and soy sauce (1.5 μg/mL). The results show that perlolyrine formed during the heating process of foods. It is concluded that perlolyrine is widely present in foods and it is daily ingested in the diet.
publishDate 2023
dc.date.none.fl_str_mv 2023
2023
2023
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/341184
url http://hdl.handle.net/10261/341184
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/AEI//PDC2022-133269-I00
info:eu-repo/grantAgreement/AEI//PID2021-127833OB-I00
Herraiz Tomico, Tomás; Peña, Adriana; Salgado, Antonio; 2023; Supporting information: Identification, formation, and occurrence of perlolyrine: A β-carboline alkaloid with a furan moiety in foods [Dataset]; American Chemical Society; https://doi.org/10.1021/acs.jafc.3c03612
https://doi.org/10.1021/acs.jafc.3c03612
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv American Chemical Society
publisher.none.fl_str_mv American Chemical Society
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869423272922185728
score 15.81155

Similares en LA Referencia