Biocatalyzed Generation of Molecular Diversity: Selective Modification of the Saponin Asiaticoside
Autor(a) principal: | |
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Data de Publicação: | 2005 |
Outros Autores: | , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/10316/8379 https://doi.org/10.1002/adsc.200505047 |
Resumo: | An array of different derivatives of the complex ursane-type triterpene glycoside asiaticoside (1), a saponin component isolated from the perennial herb Centella asiatica, was generated by exploiting the stereo-, regio- and site-selectivity of four groups of enzymes (glycosidases, glycosyltransferases, lipases and laccases). A library of extracellular alpha-L-rhamnosidases (31 different items) was obtained by screening 16 different fungal strains under different cultivation conditions, and several of these preparations catalyzed the derhamnosylation of asiaticoside. Specifically, the enzymes produced by Fusarium oxysporum were selected for the synthesis of derhamno-degluco-asiaticoside (2) and also of derhamno-asiaticoside (3), by in situ glucose-inhibition of contaminating beta-D-glucosidases. beta-1,4-Galactosyltransferase from bovine milk was subsequently used for the galactosylation of the two asiaticoside derivatives 2 and 3, using 20% v/v DMSO as a cosolvent in order to increase substrate solubility. Finally, new acylated and oxidized derivatives of asiaticoside were also prepared by exploiting the lipase from Candida antarctica (Novozym 435) and the laccase from Trametes pubescens, respectively. |
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Biocatalyzed Generation of Molecular Diversity: Selective Modification of the Saponin AsiaticosideAn array of different derivatives of the complex ursane-type triterpene glycoside asiaticoside (1), a saponin component isolated from the perennial herb Centella asiatica, was generated by exploiting the stereo-, regio- and site-selectivity of four groups of enzymes (glycosidases, glycosyltransferases, lipases and laccases). A library of extracellular alpha-L-rhamnosidases (31 different items) was obtained by screening 16 different fungal strains under different cultivation conditions, and several of these preparations catalyzed the derhamnosylation of asiaticoside. Specifically, the enzymes produced by Fusarium oxysporum were selected for the synthesis of derhamno-degluco-asiaticoside (2) and also of derhamno-asiaticoside (3), by in situ glucose-inhibition of contaminating beta-D-glucosidases. beta-1,4-Galactosyltransferase from bovine milk was subsequently used for the galactosylation of the two asiaticoside derivatives 2 and 3, using 20% v/v DMSO as a cosolvent in order to increase substrate solubility. Finally, new acylated and oxidized derivatives of asiaticoside were also prepared by exploiting the lipase from Candida antarctica (Novozym 435) and the laccase from Trametes pubescens, respectively.2005info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/8379http://hdl.handle.net/10316/8379https://doi.org/10.1002/adsc.200505047engAdvanced Synthesis & Catalysis. 347:7-8 (2005) 1168-1174Monti, DanielaCandido, AndreaCruz Silva, M. ManuelKren, VladimirRiva, SergioDanieli, Brunoinfo: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:RCAAP2020-05-25T02:17:54Zoai:estudogeral.uc.pt:10316/8379Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T20:47:21.118487Repositório 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 |
Biocatalyzed Generation of Molecular Diversity: Selective Modification of the Saponin Asiaticoside |
title |
Biocatalyzed Generation of Molecular Diversity: Selective Modification of the Saponin Asiaticoside |
spellingShingle |
Biocatalyzed Generation of Molecular Diversity: Selective Modification of the Saponin Asiaticoside Monti, Daniela |
title_short |
Biocatalyzed Generation of Molecular Diversity: Selective Modification of the Saponin Asiaticoside |
title_full |
Biocatalyzed Generation of Molecular Diversity: Selective Modification of the Saponin Asiaticoside |
title_fullStr |
Biocatalyzed Generation of Molecular Diversity: Selective Modification of the Saponin Asiaticoside |
title_full_unstemmed |
Biocatalyzed Generation of Molecular Diversity: Selective Modification of the Saponin Asiaticoside |
title_sort |
Biocatalyzed Generation of Molecular Diversity: Selective Modification of the Saponin Asiaticoside |
author |
Monti, Daniela |
author_facet |
Monti, Daniela Candido, Andrea Cruz Silva, M. Manuel Kren, Vladimir Riva, Sergio Danieli, Bruno |
author_role |
author |
author2 |
Candido, Andrea Cruz Silva, M. Manuel Kren, Vladimir Riva, Sergio Danieli, Bruno |
author2_role |
author author author author author |
dc.contributor.author.fl_str_mv |
Monti, Daniela Candido, Andrea Cruz Silva, M. Manuel Kren, Vladimir Riva, Sergio Danieli, Bruno |
description |
An array of different derivatives of the complex ursane-type triterpene glycoside asiaticoside (1), a saponin component isolated from the perennial herb Centella asiatica, was generated by exploiting the stereo-, regio- and site-selectivity of four groups of enzymes (glycosidases, glycosyltransferases, lipases and laccases). A library of extracellular alpha-L-rhamnosidases (31 different items) was obtained by screening 16 different fungal strains under different cultivation conditions, and several of these preparations catalyzed the derhamnosylation of asiaticoside. Specifically, the enzymes produced by Fusarium oxysporum were selected for the synthesis of derhamno-degluco-asiaticoside (2) and also of derhamno-asiaticoside (3), by in situ glucose-inhibition of contaminating beta-D-glucosidases. beta-1,4-Galactosyltransferase from bovine milk was subsequently used for the galactosylation of the two asiaticoside derivatives 2 and 3, using 20% v/v DMSO as a cosolvent in order to increase substrate solubility. Finally, new acylated and oxidized derivatives of asiaticoside were also prepared by exploiting the lipase from Candida antarctica (Novozym 435) and the laccase from Trametes pubescens, respectively. |
publishDate |
2005 |
dc.date.none.fl_str_mv |
2005 |
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/10316/8379 http://hdl.handle.net/10316/8379 https://doi.org/10.1002/adsc.200505047 |
url |
http://hdl.handle.net/10316/8379 https://doi.org/10.1002/adsc.200505047 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Advanced Synthesis & Catalysis. 347:7-8 (2005) 1168-1174 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
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 |
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1799133750632644608 |