Cynaratriol, a sesquiterpene lactone from Centaurea musimomum

The title compound [systematic name: 3,8-dihydr­oxy-3-(hydroxy­meth­yl)-9-methyl-6-methyl­enedeca­hydro­azuleno[4,5-b]furan-2(3H)-one], C(15)H(22)O(5), is a sesquiterpene lactone showing the typical tricyclic guaianolide skeleton which has been isolated, together with other related metabolites, from...

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Autores principales: López-Rodríguez, Matías, P. García, Victor, Zater, Hanêne, Benayache, Samir, Benayache, Fadila
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977309/
https://www.ncbi.nlm.nih.gov/pubmed/21583563
http://dx.doi.org/10.1107/S1600536809026701
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author López-Rodríguez, Matías
P. García, Victor
Zater, Hanêne
Benayache, Samir
Benayache, Fadila
author_facet López-Rodríguez, Matías
P. García, Victor
Zater, Hanêne
Benayache, Samir
Benayache, Fadila
author_sort López-Rodríguez, Matías
collection PubMed
description The title compound [systematic name: 3,8-dihydr­oxy-3-(hydroxy­meth­yl)-9-methyl-6-methyl­enedeca­hydro­azuleno[4,5-b]furan-2(3H)-one], C(15)H(22)O(5), is a sesquiterpene lactone showing the typical tricyclic guaianolide skeleton which has been isolated, together with other related metabolites, from the plant Centaurea musimomum. The present study confirms the mol­ecular structure, assigned by (1)H NMR and MS spectroscopy, as well as the the 11β-hydroxy­methyl, 3β-hydr­oxy and 4α-methyl stereochemistry. The crystal structure is built through a network of O—H⋯O hydrogen bonds involving the three hydroxyl groups that are present in the mol­ecular skeleton.
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spelling pubmed-29773092010-12-30 Cynaratriol, a sesquiterpene lactone from Centaurea musimomum López-Rodríguez, Matías P. García, Victor Zater, Hanêne Benayache, Samir Benayache, Fadila Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound [systematic name: 3,8-dihydr­oxy-3-(hydroxy­meth­yl)-9-methyl-6-methyl­enedeca­hydro­azuleno[4,5-b]furan-2(3H)-one], C(15)H(22)O(5), is a sesquiterpene lactone showing the typical tricyclic guaianolide skeleton which has been isolated, together with other related metabolites, from the plant Centaurea musimomum. The present study confirms the mol­ecular structure, assigned by (1)H NMR and MS spectroscopy, as well as the the 11β-hydroxy­methyl, 3β-hydr­oxy and 4α-methyl stereochemistry. The crystal structure is built through a network of O—H⋯O hydrogen bonds involving the three hydroxyl groups that are present in the mol­ecular skeleton. International Union of Crystallography 2009-07-15 /pmc/articles/PMC2977309/ /pubmed/21583563 http://dx.doi.org/10.1107/S1600536809026701 Text en © López-Rodríguez et al. 2009 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
López-Rodríguez, Matías
P. García, Victor
Zater, Hanêne
Benayache, Samir
Benayache, Fadila
Cynaratriol, a sesquiterpene lactone from Centaurea musimomum
title Cynaratriol, a sesquiterpene lactone from Centaurea musimomum
title_full Cynaratriol, a sesquiterpene lactone from Centaurea musimomum
title_fullStr Cynaratriol, a sesquiterpene lactone from Centaurea musimomum
title_full_unstemmed Cynaratriol, a sesquiterpene lactone from Centaurea musimomum
title_short Cynaratriol, a sesquiterpene lactone from Centaurea musimomum
title_sort cynaratriol, a sesquiterpene lactone from centaurea musimomum
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977309/
https://www.ncbi.nlm.nih.gov/pubmed/21583563
http://dx.doi.org/10.1107/S1600536809026701
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