An Interesting Backbone Rearrangement and Novel Derivatives from the Biotransformation of Trachyloban-19-oic Acid by Rhizopus stolonifer
Autor(a) principal: | |
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Data de Publicação: | 2002 |
Outros Autores: | , |
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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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 |
format |
article |
status_str |
publishedVersion |
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) |
repository.mail.fl_str_mv |
||office@jbcs.sbq.org.br |
_version_ |
1750318164591247360 |