Further Mulinane and Azorellane Diterpenoids Isolated from Mulinum crassifolium and Azorella compacta

The new mulinane diterpenoids 1 and 2 were isolated from the EtOAc extract of Mulinum crassifolium, while the rearranged mulinane 5, which was isolated for the first time from a natural source, was isolated from Azorella compacta. Compounds 1–2 were prepared by semi-synthesis thorough acetylation of...

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Main Authors: Jorge Bórquez, Alejandro Ardiles, Luis Alberto Loyola, Luis Manuel Peña-Rodriguez, Gloria María Molina-Salinas, Javier Vallejos, Isidro G. Collado, Mario J. Simirgiotis
Format: Article
Language:English
Published: MDPI AG 2014-03-01
Series:Molecules
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Online Access:http://www.mdpi.com/1420-3049/19/4/3898
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author Jorge Bórquez
Alejandro Ardiles
Luis Alberto Loyola
Luis Manuel Peña-Rodriguez
Gloria María Molina-Salinas
Javier Vallejos
Isidro G. Collado
Mario J. Simirgiotis
author_facet Jorge Bórquez
Alejandro Ardiles
Luis Alberto Loyola
Luis Manuel Peña-Rodriguez
Gloria María Molina-Salinas
Javier Vallejos
Isidro G. Collado
Mario J. Simirgiotis
author_sort Jorge Bórquez
collection DOAJ
description The new mulinane diterpenoids 1 and 2 were isolated from the EtOAc extract of Mulinum crassifolium, while the rearranged mulinane 5, which was isolated for the first time from a natural source, was isolated from Azorella compacta. Compounds 1–2 were prepared by semi-synthesis thorough acetylation of the diterpene 17-acetoxymulinic acid (3). A mechanism of reaction was proposed, while the structures of the new compounds were elucidated on the basis of comprehensive spectroscopic analysis and computational methods.
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spelling doaj.art-03817baeb5134e02938f675873d1d80a2022-12-22T00:48:04ZengMDPI AGMolecules1420-30492014-03-011943898390810.3390/molecules19043898molecules19043898Further Mulinane and Azorellane Diterpenoids Isolated from Mulinum crassifolium and Azorella compactaJorge Bórquez0Alejandro Ardiles1Luis Alberto Loyola2Luis Manuel Peña-Rodriguez3Gloria María Molina-Salinas4Javier Vallejos5Isidro G. Collado6Mario J. Simirgiotis7Laboratorio de Productos Naturales, Departamento de Química, Universidad de Antofagasta, Av. Coloso S-N, Antofagasta 1240000, ChileLaboratorio de Productos Naturales, Departamento de Química, Universidad de Antofagasta, Av. Coloso S-N, Antofagasta 1240000, ChileLaboratorio de Productos Naturales, Departamento de Química, Universidad de Antofagasta, Av. Coloso S-N, Antofagasta 1240000, ChileGrupo de Química Orgánica, Unidad de Biotecnología, Centro de Investigación Científica de Yucatán, Calle 43 No 130, Colonia Chuburná, Mérida, Yucatán 97200, MexicoDivisión de Biología Celular y Molecular, Centro de Investigación Biomédica del Noreste, Instituto Mexicano del Seguro Social, San Luis Potosí y Dos de Abril, Colonia Independencia, Monterrey, Nuevo León 64720, MexicoDepartamento de Química, Universidad Católica del Norte, Av. Angamos 610, Antofagasta 1240000, ChileDepartamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Apartado Postal 40, Puerto Real 11510, SpainLaboratorio de Productos Naturales, Departamento de Química, Universidad de Antofagasta, Av. Coloso S-N, Antofagasta 1240000, ChileThe new mulinane diterpenoids 1 and 2 were isolated from the EtOAc extract of Mulinum crassifolium, while the rearranged mulinane 5, which was isolated for the first time from a natural source, was isolated from Azorella compacta. Compounds 1–2 were prepared by semi-synthesis thorough acetylation of the diterpene 17-acetoxymulinic acid (3). A mechanism of reaction was proposed, while the structures of the new compounds were elucidated on the basis of comprehensive spectroscopic analysis and computational methods.http://www.mdpi.com/1420-3049/19/4/3898mulinanesazorellanesnew diterpenoidsChilean native plantssemisynthesis
spellingShingle Jorge Bórquez
Alejandro Ardiles
Luis Alberto Loyola
Luis Manuel Peña-Rodriguez
Gloria María Molina-Salinas
Javier Vallejos
Isidro G. Collado
Mario J. Simirgiotis
Further Mulinane and Azorellane Diterpenoids Isolated from Mulinum crassifolium and Azorella compacta
Molecules
mulinanes
azorellanes
new diterpenoids
Chilean native plants
semisynthesis
title Further Mulinane and Azorellane Diterpenoids Isolated from Mulinum crassifolium and Azorella compacta
title_full Further Mulinane and Azorellane Diterpenoids Isolated from Mulinum crassifolium and Azorella compacta
title_fullStr Further Mulinane and Azorellane Diterpenoids Isolated from Mulinum crassifolium and Azorella compacta
title_full_unstemmed Further Mulinane and Azorellane Diterpenoids Isolated from Mulinum crassifolium and Azorella compacta
title_short Further Mulinane and Azorellane Diterpenoids Isolated from Mulinum crassifolium and Azorella compacta
title_sort further mulinane and azorellane diterpenoids isolated from mulinum crassifolium and azorella compacta
topic mulinanes
azorellanes
new diterpenoids
Chilean native plants
semisynthesis
url http://www.mdpi.com/1420-3049/19/4/3898
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