An Interesting Backbone Rearrangement and Novel Derivatives from the Biotransformation of Trachyloban-19-oic Acid by Rhizopus stolonifer

Detalhes bibliográficos
Autor(a) principal: Silva,Eliane A.
Data de Publicação: 2002
Outros Autores: Takahashi,Jacqueline A., Oliveira,Alaíde B.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532002000100016
Resumo: A biotransformation experiment of trachyloban-19-oic acid (2) was carried out with Rhizopus stolonifer. After twenty days of reaction, four metabolites were extracted, isolated and characterized: two trachylobane type compounds, the 7beta (3) and the 17 (5) hydroxyl derivatives, and two rearranged ent-kaur-11-en-19-oic acids, the 16beta (4) and the 9alpha,16beta (6) hydroxylated compounds. Products 4 and 5 were isolated as their methyl esters (4a and 5a) after esterification of a mixture containing their corresponding acids. The rearrangement of a trachylobane diterpene leading to ent-16beta-hydroxy-kaur-11-ene derivatives gives support to the biogenetic proposal based on the occurrence of this rare group of kaurenes only in plants containing trachylobane representatives. By the best of our knowledge, this is the first report on the isolation of compounds 5 and 6.
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spelling An Interesting Backbone Rearrangement and Novel Derivatives from the Biotransformation of Trachyloban-19-oic Acid by Rhizopus stoloniferbiotransformationRhizopus stolonifertrachyloban-19-oic acidrearrangementA biotransformation experiment of trachyloban-19-oic acid (2) was carried out with Rhizopus stolonifer. After twenty days of reaction, four metabolites were extracted, isolated and characterized: two trachylobane type compounds, the 7beta (3) and the 17 (5) hydroxyl derivatives, and two rearranged ent-kaur-11-en-19-oic acids, the 16beta (4) and the 9alpha,16beta (6) hydroxylated compounds. Products 4 and 5 were isolated as their methyl esters (4a and 5a) after esterification of a mixture containing their corresponding acids. The rearrangement of a trachylobane diterpene leading to ent-16beta-hydroxy-kaur-11-ene derivatives gives support to the biogenetic proposal based on the occurrence of this rare group of kaurenes only in plants containing trachylobane representatives. By the best of our knowledge, this is the first report on the isolation of compounds 5 and 6.Sociedade Brasileira de Química2002-02-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532002000100016Journal of the Brazilian Chemical Society v.13 n.1 2002reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532002000100016info:eu-repo/semantics/openAccessSilva,Eliane A.Takahashi,Jacqueline A.Oliveira,Alaíde B.eng2002-06-20T00:00:00Zoai:scielo:S0103-50532002000100016Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2002-06-20T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv An Interesting Backbone Rearrangement and Novel Derivatives from the Biotransformation of Trachyloban-19-oic Acid by Rhizopus stolonifer
title An Interesting Backbone Rearrangement and Novel Derivatives from the Biotransformation of Trachyloban-19-oic Acid by Rhizopus stolonifer
spellingShingle An Interesting Backbone Rearrangement and Novel Derivatives from the Biotransformation of Trachyloban-19-oic Acid by Rhizopus stolonifer
Silva,Eliane A.
biotransformation
Rhizopus stolonifer
trachyloban-19-oic acid
rearrangement
title_short An Interesting Backbone Rearrangement and Novel Derivatives from the Biotransformation of Trachyloban-19-oic Acid by Rhizopus stolonifer
title_full An Interesting Backbone Rearrangement and Novel Derivatives from the Biotransformation of Trachyloban-19-oic Acid by Rhizopus stolonifer
title_fullStr An Interesting Backbone Rearrangement and Novel Derivatives from the Biotransformation of Trachyloban-19-oic Acid by Rhizopus stolonifer
title_full_unstemmed An Interesting Backbone Rearrangement and Novel Derivatives from the Biotransformation of Trachyloban-19-oic Acid by Rhizopus stolonifer
title_sort An Interesting Backbone Rearrangement and Novel Derivatives from the Biotransformation of Trachyloban-19-oic Acid by Rhizopus stolonifer
author Silva,Eliane A.
author_facet Silva,Eliane A.
Takahashi,Jacqueline A.
Oliveira,Alaíde B.
author_role author
author2 Takahashi,Jacqueline A.
Oliveira,Alaíde B.
author2_role author
author
dc.contributor.author.fl_str_mv Silva,Eliane A.
Takahashi,Jacqueline A.
Oliveira,Alaíde B.
dc.subject.por.fl_str_mv biotransformation
Rhizopus stolonifer
trachyloban-19-oic acid
rearrangement
topic biotransformation
Rhizopus stolonifer
trachyloban-19-oic acid
rearrangement
description A biotransformation experiment of trachyloban-19-oic acid (2) was carried out with Rhizopus stolonifer. After twenty days of reaction, four metabolites were extracted, isolated and characterized: two trachylobane type compounds, the 7beta (3) and the 17 (5) hydroxyl derivatives, and two rearranged ent-kaur-11-en-19-oic acids, the 16beta (4) and the 9alpha,16beta (6) hydroxylated compounds. Products 4 and 5 were isolated as their methyl esters (4a and 5a) after esterification of a mixture containing their corresponding acids. The rearrangement of a trachylobane diterpene leading to ent-16beta-hydroxy-kaur-11-ene derivatives gives support to the biogenetic proposal based on the occurrence of this rare group of kaurenes only in plants containing trachylobane representatives. By the best of our knowledge, this is the first report on the isolation of compounds 5 and 6.
publishDate 2002
dc.date.none.fl_str_mv 2002-02-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532002000100016
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532002000100016
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532002000100016
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.13 n.1 2002
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
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