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Natural Product Research
Formerly Natural Product Letters
Volume 29, 2015 - Issue 3
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Articles

Synthesis and biological evaluation of ( − )-13,14-dihydroxy-8,11,13-podocarpatrien-7-one and derivatives from (+)-manool

María L. NovoaCentro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Apartado 21827, Caracas1020-A, VenezuelaView further author information
,
Yelisbeth EscalanteCentro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Apartado 21827, Caracas1020-A, VenezuelaView further author information
,
Liliana MaldonadoCentro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Apartado 21827, Caracas1020-A, VenezuelaView further author information
,
Iván Galindo-CastroLaboratorio de Genómica y Proteómica, Fundación IDEA, Caracas, VenezuelaView further author information
,
Annamil ÁlvarezLaboratorio de Genómica y Proteómica, Fundación IDEA, Caracas, VenezuelaView further author information
,
Katherine FigarellaLaboratorio de Genómica y Proteómica, Fundación IDEA, Caracas, VenezuelaView further author information
,
Sabrina MarsiccobetreLaboratorio de Genómica y Proteómica, Fundación IDEA, Caracas, VenezuelaView further author information
,
Irina ArochaLaboratorio de Genómica y Proteómica, Fundación IDEA, Caracas, VenezuelaView further author information
,
Jais NievesLaboratorio de Genómica y Proteómica, Fundación IDEA, Caracas, VenezuelaView further author information
,
Franklin SalazarCentro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Apartado 21827, Caracas1020-A, VenezuelaView further author information
,
Carlos GámezCentro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Apartado 21827, Caracas1020-A, Venezuela;Departamento de Química, Universidad Simón Bolívar, Apartado 89000, Caracas1080-A, VenezuelaView further author information
,
Nieves CanudasDepartamento de Química, Universidad Simón Bolívar, Apartado 89000, Caracas1080-A, VenezuelaView further author information
,
Eleonora TropperCentro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Apartado 21827, Caracas1020-A, VenezuelaView further author information
,
Teresa GonzálezCentro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Apartado 21827, Caracas1020-A, VenezuelaView further author information
&
José E. VillamizarCentro de Química, Instituto Venezolano de Investigaciones Científicas (I.V.I.C.), Apartado 21827, Caracas1020-A, VenezuelaCorrespondence[email protected]
View further author information
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Pages 207-212 | Received 10 Mar 2014, Accepted 03 Jul 2014, Published online: 30 Jul 2014
 
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Abstract

13,14-Dihydroxy-8,11,13-podocarpatrien-7-one (1) and a series of ring C aromatic diterpene derivatives were synthesised from (+)-manool (4) and evaluated for their cytotoxic, leishmanicidal and trypanocidal activities. Our results indicated that compound 1 and other podocarpane-type intermediates are cytotoxic. Cleavage of C6–C7 bond of compound 7 improved cytotoxic activity, indicating that, in particular, the 6,7-seco-podocarpane-type compound 20 might serve as a lead compound for further development.

Acknowledgements

The authors thank the laboratories of Mass Spectrometry (Ana Angarita and Matilde Gómez), NMR (Sara Pekerar, Alberto Fuentes, Liz Cubillan and Ligia Llovera) and Elemental Analyses (EleinneSeverino) of IVIC for the research support.

Additional information

Funding

This research was supported by FONACIT [grand number 2007000960], [grand number 2007001522], Foundation IDEA (POA-2012), and FONDEN.

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