title: The analgesic and anti-inflammatory effect of new oleanolic acid acyloxyimino derivative.
abstract: The new derivative of well-known triterpene, oleanolic acid: methyl 3-octanoyloxyiminoolean-12-en-28-oate 5, was synthesized by the action of caprylic acid on methyl oleanolate 3-oxime in the presence of dicyclohexylcarbodiimide in dioxane. The molecular structure of the obtained product 5 was confirmed by spectral methods. The acute toxicity, locomotor activity, and the dose-dependent analgesic activity were studied. In addition, the effect of compound 5 on morphine-induced analgesic activity, the dose-dependent anti-inflammatory activity and the effect of the compound on diclofenac anti-inflammatory activity study were performed. The results proved a low toxicity (LD₅₀ > 2 g/kg) of the tested product 5, which affected neither vertical nor horizontal locomotor activity in the given range of doses. The triterpene 5 also produced centrally mediated (morphine-like) analgesic action; however, only in the highest dose. The synergistic analgesic activity of 5 and morphine in the doses of 30.0 and 300.0mg/kg was found. Compound 5 expressed the anti-inflammatory action which did not affect the anti-inflammatory activity of diclofenac after their combined administration.
authors.affiliation: Department of Organic Chemistry, Faculty of Pharmacy, Poznan University of Medical Sciences, Grunwaldzka Str. 6, 60-780 Poznan, Poland. bcwynar@ump.edu.pl
authors.forename: Barbara
authors.initials: B
authors.lastname: Bednarczyk-Cwynar
authors.forename: Lucjusz
authors.initials: L
authors.lastname: Zaprutko
authors.forename: Joanna
authors.initials: J
authors.lastname: Marciniak
authors.forename: Grzegorz
authors.initials: G
authors.lastname: Lewandowski
authors.forename: Michal
authors.initials: M
authors.lastname: Szulc
authors.forename: Ewa
authors.initials: E
authors.lastname: Kaminska
authors.forename: Natalia
authors.initials: N
authors.lastname: Wachowiak
authors.forename: Przemyslaw Lukasz
authors.initials: PL
authors.lastname: Mikolajczak
mesh_terms: D000700:Analgesics / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use*; D000818:Animals; D000893:Anti-Inflammatory Agents / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use*; D002351:Carrageenan; D003875:Drug Eruptions / Q000188:drug therapy*; D004357:Drug Synergism; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D008297:Male; D051379:Mice; D009020:Morphine / Q000494:pharmacology; D009043:Motor Activity / Q000187:drug effects; D009828:Oleanolic Acid / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology / Q000627:therapeutic use; D010146:Pain / Q000188:drug therapy*; D051381:Rats; D017208:Rats, Wistar; D023382:Toxicity Tests, Acute
chemical_list: D000700:Analgesics; D000893:Anti-Inflammatory Agents; C578345:methyl 3-octanoyloxyiminoolean-12-en-28-oate; D009828:Oleanolic Acid; D009020:Morphine; D002351:Carrageenan