Secochiliolide ester derivatives: Preparation and evaluation of their antitrypanosomal and antimalarial efficacy

  title={Secochiliolide ester derivatives: Preparation and evaluation of their antitrypanosomal and antimalarial efficacy},
  author={Romina J Ronchi and Claire Beaufay and Joanne Bero and Juan B Robirosa and Marcia Mazzuca and Jorge A. Palermo and Jo{\"e}lle Quetin-Leclercq and Marianela S{\'a}nchez},
  journal={Chemical Biology \& Drug Design},
  pages={147 - 153}
In the present study, a series of new esters of secochiliolide acid (SA), a diterpene isolated from Nardophyllum bryoides, were synthesized in good yield. All compounds were evaluated for their in vitro antiparasitic properties (on Plasmodium falciparum and Trypanosoma brucei brucei) and cytotoxicity (on WI38, normal mammalian cells). They displayed moderate antitrypanosomal activity with IC50 values between 2.55 and 18.14 μm, with selectivity indices >10, and low antiplasmodial effects with… 


Preparation and antitrypanosomal activity of secochiliolide acid derivatives.
The results indicate that the carboxyl group is not essential for the bioactivity of 1, while the presence of the tetrasubstituted exocyclic double bond seems to be important.
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Further investigation of the aerial parts of Alomia myriadenia revealed an halimane diterpene identified as ent-8S,12S-epoxy-7R,16-dihydroxyhalima-5(10),13-dien-15-16-olide, which was evaluated in a panel of human cancer cell lines and caused lysis of 100% of the parasites at 250 mug/ml.
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Data indicate that synthetically-modified natural products comprise valuable tools in antiparasitic chemotherapy and that electron microscopy may be useful not only in determining the mechanisms of action but also in directing such modifications for rational drug design.
Structure Elucidation, Antimicrobial and Cytotoxic Activities of a Halimane Isolated from Vellozia kolbekii Alves (Velloziaceae)
In the mechanism of cytotoxic action, halimane 1 interferes in two major phases of the cell cycle: in S phase, in which DNA synthesis occurs and where it is very sensitive to damage, and G2M phase which is the phase of preparation for mitosis and mitosis itself, showing apoptosis‐inducing properties.
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The established link between erythrocyte membrane modifications and antiplasmodial activity may provide a novel target for potential antimalarial drugs.