Structural determination Vitex cymosa Bertero active principle: Diastereoselective synthesis of (+/-)-trans-4-hydroxy-6-propyl-1-oxocyclohexan-2-one and its antinociceptive activity

Leandro S de Maris e Miranda; Bruno Guimarães Marinho; Jeronimo S Costa; Suzana G Leitão; Tereza Cristina dos Santos; Franco Delle Monache; Patricia Dias Fernandes; Mário Luiz A A Vasconcellos; Vera L Patrocinio Pereira

doi:10.1016/j.bioorg.2010.05.001

Structural determination Vitex cymosa Bertero active principle: Diastereoselective synthesis of (+/-)-trans-4-hydroxy-6-propyl-1-oxocyclohexan-2-one and its antinociceptive activity

Bioorg Chem. 2010 Oct;38(5):181-5. doi: 10.1016/j.bioorg.2010.05.001. Epub 2010 May 25.

Authors

Leandro S de Maris e Miranda¹, Bruno Guimarães Marinho, Jeronimo S Costa, Suzana G Leitão, Tereza Cristina dos Santos, Franco Delle Monache, Patricia Dias Fernandes, Mário Luiz A A Vasconcellos, Vera L Patrocinio Pereira

Affiliation

¹ Universidade Federal do Rio de Janeiro, Centro de Ciências da Saúde, Rio de Janeiro, RJ, Brazil.

PMID: 20538314
DOI: 10.1016/j.bioorg.2010.05.001

Abstract

The diastereoselective synthesis of (+/-)-trans-4-hydroxy-6-propyl-1-oxocyclohexan-2-one, as a mixture trans:cis (3:1), was accomplished using a protocol that combine the Prins cyclization and RuO(4) oxidation. The synthesis this lactone allowed the elucidation of the correct structure of the substance isolated from the barks of Vitex cymosa. The delta-lactones mixture showed significant antinociceptive properties in preliminary tests using the tail flick model assay.

Publication types

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

MeSH terms

Analgesics / chemical synthesis
Analgesics / chemistry*
Analgesics / therapeutic use*
Animals
Cyclization
Lactones / chemical synthesis
Lactones / chemistry*
Lactones / therapeutic use*
Molecular Structure
Pain / drug therapy*
Stereoisomerism
Vitex / chemistry*

Substances

Analgesics
Lactones