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Trypanocidal structure-activity relationship for cis- and trans-methylpluviatolide.
Phytochemistry. 2008 Jun; 69(9):1890-4.P

Abstract

The trypanocidal activity of racemic mixtures of cis- and trans-methylpluviatolides was evaluated in vitro against trypomastigote forms of two strains of Trypanosoma cruzi, and in the enzymatic assay of T. cruzi gGAPDH. The cytotoxicity of the compounds was assessed by the MTT method using LLC-MK2 cells. The effect of the compounds on peroxide and NO production were also investigated. The mixture of the trans stereoisomers displayed trypanocidal activity (IC50 approximately 89.3 microM). Therefore, it was separated by chiral HPLC, furnishing the (+) and (-)-enantiomers. Only the (-)-enantiomer was active against the parasite (IC50 approximately 18.7 microM). Despite being inactive, the (+)-enantiomer acted as an antagonistic competitor. Trans-methylpluviatolide displayed low toxicity for LLC-MK2 cells, with an IC50 of 6.53 mM. Furthermore, methylpluviatolide neither inhibited gGAPDH activity nor hindered peroxide and NO production at the evaluated concentrations.

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Authors+Show Affiliations

da Silva R
Núcleo de Ciências Exatas e Tecnológicas, Universidade de Franca, Avenida Dr. Armando Salles de Oliveira, 2001, 14404-600 Franca, SP, Brazil.
Saraiva J
No affiliation info available
de Albuquerque S
No affiliation info available
Curti C
No affiliation info available
Donate PM
No affiliation info available
Bianco TN
No affiliation info available
Bastos JK
No affiliation info available
Silva ML
No affiliation info available

MeSH

AnimalsCell LineLactonesLignansMacrophagesMiceMolecular StructureNitric OxideStructure-Activity RelationshipTrypanocidal AgentsTrypanosoma cruzi

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

18479721

Citation

da Silva, R, et al. "Trypanocidal Structure-activity Relationship for Cis- and Trans-methylpluviatolide." Phytochemistry, vol. 69, no. 9, 2008, pp. 1890-4.
da Silva R, Saraiva J, de Albuquerque S, et al. Trypanocidal structure-activity relationship for cis- and trans-methylpluviatolide. Phytochemistry. 2008;69(9):1890-4.
da Silva, R., Saraiva, J., de Albuquerque, S., Curti, C., Donate, P. M., Bianco, T. N., Bastos, J. K., & Silva, M. L. (2008). Trypanocidal structure-activity relationship for cis- and trans-methylpluviatolide. Phytochemistry, 69(9), 1890-4. https://doi.org/10.1016/j.phytochem.2008.04.002
da Silva R, et al. Trypanocidal Structure-activity Relationship for Cis- and Trans-methylpluviatolide. Phytochemistry. 2008;69(9):1890-4. PubMed PMID: 18479721.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Trypanocidal structure-activity relationship for cis- and trans-methylpluviatolide. AU - da Silva,R, AU - Saraiva,J, AU - de Albuquerque,S, AU - Curti,C, AU - Donate,P M, AU - Bianco,T N C, AU - Bastos,J K, AU - Silva,M L A, Y1 - 2008/05/12/ PY - 2007/10/25/received PY - 2008/02/08/revised PY - 2008/04/02/accepted PY - 2008/5/16/pubmed PY - 2008/9/11/medline PY - 2008/5/16/entrez SP - 1890 EP - 4 JF - Phytochemistry JO - Phytochemistry VL - 69 IS - 9 N2 - The trypanocidal activity of racemic mixtures of cis- and trans-methylpluviatolides was evaluated in vitro against trypomastigote forms of two strains of Trypanosoma cruzi, and in the enzymatic assay of T. cruzi gGAPDH. The cytotoxicity of the compounds was assessed by the MTT method using LLC-MK2 cells. The effect of the compounds on peroxide and NO production were also investigated. The mixture of the trans stereoisomers displayed trypanocidal activity (IC50 approximately 89.3 microM). Therefore, it was separated by chiral HPLC, furnishing the (+) and (-)-enantiomers. Only the (-)-enantiomer was active against the parasite (IC50 approximately 18.7 microM). Despite being inactive, the (+)-enantiomer acted as an antagonistic competitor. Trans-methylpluviatolide displayed low toxicity for LLC-MK2 cells, with an IC50 of 6.53 mM. Furthermore, methylpluviatolide neither inhibited gGAPDH activity nor hindered peroxide and NO production at the evaluated concentrations. SN - 0031-9422 UR - https://www.unboundmedicine.com/medline/citation/18479721/Trypanocidal_structure_activity_relationship_for_cis__and_trans_methylpluviatolide_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(08)00180-5 DB - PRIME DP - Unbound Medicine ER -