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Molecules 2014, 19(4), 3898-3908; doi:10.3390/molecules19043898

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

1 Laboratorio de Productos Naturales, Departamento de Química, Universidad de Antofagasta, Av. Coloso S-N, Antofagasta 1240000, Chile 2 Grupo de Química Orgánica, Unidad de Biotecnología, Centro de Investigación Científica de Yucatán, Calle 43 No 130, Colonia Chuburná, Mérida, Yucatán 97200, Mexico 3 División 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, Mexico 4 Unidad de Alta Especialidad Médica Yucatán Lic. Ignacio García Téllez Calle 41 No 439 x 32 y 34, Col. Industrial, CP 97150, Mérida, Yucatan 97200, Mexico 5 Departamento de Química, Universidad Católica del Norte, Av. Angamos 610, Antofagasta 1240000, Chile 6 Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Cádiz, Apartado Postal 40, Puerto Real 11510, Spain
* Author to whom correspondence should be addressed.
Received: 3 March 2014 / Revised: 19 March 2014 / Accepted: 21 March 2014 / Published: 28 March 2014
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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 12 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.
Keywords: mulinanes; azorellanes; new diterpenoids; Chilean native plants; semisynthesis mulinanes; azorellanes; new diterpenoids; Chilean native plants; semisynthesis
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Bórquez, J.; Ardiles, A.; Loyola, L.A.; Peña-Rodriguez, L.M.; Molina-Salinas, G.M.; Vallejos, J.; Collado, I.G.; Simirgiotis, M.J. Further Mulinane and Azorellane Diterpenoids Isolated from Mulinum crassifolium and Azorella compacta. Molecules 2014, 19, 3898-3908.

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