ABSTRACT
In the title compound, C(14)H(17)NO(3), the piperidine ring has a chair conformation and an intra-molecular C-Hâ¯O inter-action stabilizes the mol-ecular conformation. In the crystal, weak inter-molecular C-Hâ¯O inter-actions occur.
ABSTRACT
The pericarp and seeds from fruits of Garcinia brasiliensis were subjected to extraction with hexane and ethanol. The pericarp hexane extract (PHE) and seed ethanol extract (SEE) were purified by silica gel column chromatography, which permitted isolation of the prenylated benzophenones 7-epiclusianone (1) and guttiferone-A (2), respectively. The antimicrobial activity of PHE, SEE, and compounds 1 and 2 were evaluated against Candida albicans, Staphylococcus aureus, Escherichia coli, and Bacillus cereus cultures. The minimum inhibitory concentration and minimum bactericidal concentration were established. The substances presented activity against S. aureus and B. cereus as follows: PHE, 4.0 microg/mL and 2.4 microg/mL; SEE, 10.0 microg/mL and 12.6 microg/mL; 7-epiclusianone, 1.2 microg/mL and 0.6 microg/mL; and guttiferone-A, 2.4 microg/mL and 2.4 microg/mL, respectively. The direct relationship between the lipophilic character of the structure and activity in Gram-positive bacteria was specifically observed. Therefore these extracts and prenylated benzophenones represent an interesting topic for further studies and open possibilities for an alternative control of diseases associated with Gram-positive bacteria.
Subject(s)
Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Benzophenones/pharmacology , Benzoquinones/pharmacology , Garcinia , Phloroglucinol/pharmacology , Plant Extracts/pharmacology , Anti-Bacterial Agents/isolation & purification , Antifungal Agents/isolation & purification , Bacteria/drug effects , Benzophenones/isolation & purification , Benzoquinones/isolation & purification , Candida albicans/drug effects , Fruit , Garcinia/chemistry , Microbial Sensitivity Tests , Phloroglucinol/analogs & derivatives , Phloroglucinol/isolation & purification , Plant Extracts/chemistry , Plant Extracts/isolation & purification , SeedsABSTRACT
Prostaglandin-H synthase exists in two isoforms, PGHS-1 and PGHS-2. PGHS-1 is present and is constitutively expressed in most cells and tissues, whereas PGHS-2 is mainly thought to mediate inflammation. Selective prostaglandin-H synthase-2 (or cyclooxygenase-2) inhibitors have been shown to be potent antiinflammatory agents with fewer side effects than currently marketed nonsteroidal antiinflammatory drugs (NSAIDs). This review addresses the main classes of the selective PGHS-2 inhibitors whose selectivity is documented by supporting PGHS-1 and PGHS-2 enzyme data. In addition, we also describe our experience in design, synthesis and pharmacological in vivo evaluation of new 1,2-benzodioxole derivatives as candidate of the selective PGHS-2 inhibitors, with special attention to molecular dynamics simulations of these derivatives attached to the active site of PGHS-2.
