Abstract
A new series of 19-nor-clerodane diterpene derivatives was synthesized from the natural trans-dehydrocrotonin obtained from stem barks of Croton cajucara (Euphorbiaceae), a native medicinal plant of the Brazilian Amazon. The new derivatives were obtained by changes in the ketone moiety of trans-dehydrocrotonin leading to nitrogenated derivatives which are: three substituted hydrazine diterpenes, oxime, and methyloxime. The cytotoxic effect of the diterpene derivatives was evaluated by MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay against Ehrlich carcinoma and K562 human leukemia cells. The cytotoxic activity of the hydrazine and oxime semi-synthetic derivatives was better than the one of the natural product trans-dehydrocrotonin. Moreover, all diterpenes were tested for their DNA topoisomerase I inhibitory activity, and the most effective one, in general, was observed to the phenyl-hydrazone derivative. Results indicated that the topoisomerase I inhibitory effect is correlated with the cytotoxic activity.
Highlights
Medicinal plants are the dominant form of medicine in most countries, and the World Health Organization estimates that around 80% of the world population in developing countries relies on traditional plant medicines for primary healthcare needs.1Many Euphorbiaceae plants are well known in different parts of the world as toxic and/or medicinal, and Croton is a large genus of this family widely distributed in tropical and subtropical regions of both hemispheres
We report the synthesis of five new trans-dehydrocrotonin nitrogenated derivatives, and their in vitro evaluation of cytotoxic activity
Clerodane 1 was isolated from the stem bark of methanol extract of Croton cajucara, as previously described
Summary
Medicinal plants are the dominant form of medicine in most countries, and the World Health Organization estimates that around 80% of the world population in developing countries relies on traditional plant medicines for primary healthcare needs.1Many Euphorbiaceae plants are well known in different parts of the world as toxic and/or medicinal, and Croton is a large genus of this family widely distributed in tropical and subtropical regions of both hemispheres. We report the synthesis of five new trans-dehydrocrotonin nitrogenated derivatives, and their in vitro evaluation of cytotoxic activity.
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