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Cycloartanes from Krameria pauciflora and Their In Vitro PLA2, COX-1, and COX-2 Enzyme Inhibitory Activities

2012; Thieme Medical Publishers (Germany); Volume: 78; Issue: 18 Linguagem: Inglês

10.1055/s-0032-1327882

1439-0221

M. Ángeles Ramírez‐Cisneros, Marı́a Yolanda Rios, Ramiro Ríos-Gómez, A. Berenice Aguilar‐Guadarrama,

Cholinesterase and Neurodegenerative Diseases

Krameria pauciflora is a species belonging to the Krameriaceae family. It has been used to treat inflammatory disorders in folkloric Mexican medicine; however, chemistry and pharmacological studies have not been carried out on this species. In this work, from the dichloromethane root extract of K. pauciflora, five cycloartane-type triterpenoids were isolated: cyclomargenyl-3- O - β -caffeoyl ester ( 1 ), cyclomargenyl-3- O - β -feruloyl ester ( 2 ), cyclomargenyl-3- O - β -coumaroyl ester ( 3 ), cyclomargenol ( 4 , polysthicol), and cyclomargenone ( 5 ). Additionally, the lignane 6′-methoxyrataniaphenol was isolated. To the best of our knowledge, compounds 1 – 3 are new natural products, whereas compounds 4 and 5 are isolated for the first time in the Krameria genus and the Krameriaceae family. The structures of all of these compounds were established by 1D and 2D NMR spectroscopy including 1 H, 13 C, DEPT, COSY, HSQC, and HMBC experiments, as well as by EI mass spectrometry. There is an incomplete previous report about the spectroscopic data of compounds 4 and 5 . However, in this work, a complete and unambiguous assignation has been realized. Due to the traditional use of this plant and other species from this genus, such as K. lappacea , cycloartanes isolated herein were evaluated by their inhibition of phospholipase A 2 , cyclooxygenase-1, and cyclooxygenase-2 enzymes. Cyclomargenyl-3- O - β -caffeoyl ester ( 1 ) showed inhibition of phospholipase A 2 , cyclooxygenase-1, and cyclooxygenase-2 target enzymes for nonsteroidal anti-inflammatory drugs. Both cyclooxygenases were inhibited by cyclomargenol ( 4 ); however, cyclomargenyl-3- O - β -feruloyl ester ( 2 ) showed inhibition only on cyclooxygenase-1.