Hydroxystilbene glucosides are incorporated into Norway spruce bark lignin

Detalhes bibliográficos
Autor(a) principal: Rencoret, Jorge
Data de Publicação: 2019
Outros Autores: Neiva, Duarte M., Marques, Gisela, Gutiérrez, Ana, Kim, Hoon, Gominho, Jorge, Pereira, H., Ralph, John, Rio, José C. del
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10400.5/18209
Resumo: Recent investigations have revealed that, in addition to monolignols, some phenolic compounds derived from the flavonoid and hydroxystilbene biosynthetic pathways can also function as true lignin monomers in some plants. In this study, we found that the hydroxystilbene glucosides isorhapontin (isorhapontigenin-O-glucoside) and, at lower levels, astringin (piceatannol- O-glucoside) and piceid (resveratrol-O-glucoside) are incorporated into the lignin polymer in Norway spruce (Picea abies) bark. The corresponding aglycones isorhapontigenin, piceatannol, and resveratrol, along with glucose, were released by derivatization followed by reductive cleavage, a chemical degradative method that cleaves b-ether bonds in lignin, indicating that the hydroxystilbene glucosides are (partially) incorporated into the lignin structure through b-ether bonds. Twodimensional NMR analysis confirmed the occurrence of hydroxystilbene glucosides in this lignin, and provided additional information regarding their modes of incorporation into the polymer. The hydroxystilbene glucosides, particularly isorhapontin and astringin, can therefore be considered genuine lignin monomers that participate in coupling and crosscoupling reactions during lignification in Norway spruce bark
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spelling Hydroxystilbene glucosides are incorporated into Norway spruce bark ligninNorway sprucebarkligninhydroxystilbene glucosidesRecent investigations have revealed that, in addition to monolignols, some phenolic compounds derived from the flavonoid and hydroxystilbene biosynthetic pathways can also function as true lignin monomers in some plants. In this study, we found that the hydroxystilbene glucosides isorhapontin (isorhapontigenin-O-glucoside) and, at lower levels, astringin (piceatannol- O-glucoside) and piceid (resveratrol-O-glucoside) are incorporated into the lignin polymer in Norway spruce (Picea abies) bark. The corresponding aglycones isorhapontigenin, piceatannol, and resveratrol, along with glucose, were released by derivatization followed by reductive cleavage, a chemical degradative method that cleaves b-ether bonds in lignin, indicating that the hydroxystilbene glucosides are (partially) incorporated into the lignin structure through b-ether bonds. Twodimensional NMR analysis confirmed the occurrence of hydroxystilbene glucosides in this lignin, and provided additional information regarding their modes of incorporation into the polymer. The hydroxystilbene glucosides, particularly isorhapontin and astringin, can therefore be considered genuine lignin monomers that participate in coupling and crosscoupling reactions during lignification in Norway spruce barkAmerican Society of Plant BiologistsRepositório da Universidade de LisboaRencoret, JorgeNeiva, Duarte M.Marques, GiselaGutiérrez, AnaKim, HoonGominho, JorgePereira, H.Ralph, JohnRio, José C. del2019-08-01T12:59:56Z20192019-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10400.5/18209engPlant Physiology, July 2019 , Vol. 180, pp. 1310–1321info:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2024-11-20T19:03:57Zoai:repositorio.ul.pt:10400.5/18209Portal AgregadorONGhttps://www.rcaap.pt/oai/openairemluisa.alvim@gmail.comopendoar:71602024-11-20T19:03:57Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Hydroxystilbene glucosides are incorporated into Norway spruce bark lignin
title Hydroxystilbene glucosides are incorporated into Norway spruce bark lignin
spellingShingle Hydroxystilbene glucosides are incorporated into Norway spruce bark lignin
Rencoret, Jorge
Norway spruce
bark
lignin
hydroxystilbene glucosides
title_short Hydroxystilbene glucosides are incorporated into Norway spruce bark lignin
title_full Hydroxystilbene glucosides are incorporated into Norway spruce bark lignin
title_fullStr Hydroxystilbene glucosides are incorporated into Norway spruce bark lignin
title_full_unstemmed Hydroxystilbene glucosides are incorporated into Norway spruce bark lignin
title_sort Hydroxystilbene glucosides are incorporated into Norway spruce bark lignin
author Rencoret, Jorge
author_facet Rencoret, Jorge
Neiva, Duarte M.
Marques, Gisela
Gutiérrez, Ana
Kim, Hoon
Gominho, Jorge
Pereira, H.
Ralph, John
Rio, José C. del
author_role author
author2 Neiva, Duarte M.
Marques, Gisela
Gutiérrez, Ana
Kim, Hoon
Gominho, Jorge
Pereira, H.
Ralph, John
Rio, José C. del
author2_role author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Repositório da Universidade de Lisboa
dc.contributor.author.fl_str_mv Rencoret, Jorge
Neiva, Duarte M.
Marques, Gisela
Gutiérrez, Ana
Kim, Hoon
Gominho, Jorge
Pereira, H.
Ralph, John
Rio, José C. del
dc.subject.por.fl_str_mv Norway spruce
bark
lignin
hydroxystilbene glucosides
topic Norway spruce
bark
lignin
hydroxystilbene glucosides
description Recent investigations have revealed that, in addition to monolignols, some phenolic compounds derived from the flavonoid and hydroxystilbene biosynthetic pathways can also function as true lignin monomers in some plants. In this study, we found that the hydroxystilbene glucosides isorhapontin (isorhapontigenin-O-glucoside) and, at lower levels, astringin (piceatannol- O-glucoside) and piceid (resveratrol-O-glucoside) are incorporated into the lignin polymer in Norway spruce (Picea abies) bark. The corresponding aglycones isorhapontigenin, piceatannol, and resveratrol, along with glucose, were released by derivatization followed by reductive cleavage, a chemical degradative method that cleaves b-ether bonds in lignin, indicating that the hydroxystilbene glucosides are (partially) incorporated into the lignin structure through b-ether bonds. Twodimensional NMR analysis confirmed the occurrence of hydroxystilbene glucosides in this lignin, and provided additional information regarding their modes of incorporation into the polymer. The hydroxystilbene glucosides, particularly isorhapontin and astringin, can therefore be considered genuine lignin monomers that participate in coupling and crosscoupling reactions during lignification in Norway spruce bark
publishDate 2019
dc.date.none.fl_str_mv 2019-08-01T12:59:56Z
2019
2019-01-01T00:00:00Z
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://hdl.handle.net/10400.5/18209
url http://hdl.handle.net/10400.5/18209
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Plant Physiology, July 2019 , Vol. 180, pp. 1310–1321
dc.rights.driver.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 Society of Plant Biologists
publisher.none.fl_str_mv American Society of Plant Biologists
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
repository.mail.fl_str_mv mluisa.alvim@gmail.com
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