Semisynthesis of Derivatives of Oleanolic Acid from Syzygium aromaticum and Their Antinociceptive and Anti-Inflammatory Properties

Oleanolic acid is a pentacyclic triterpenoid compound widely found in plants and well known for its medicinal properties. Oleanolic acid (OA) was isolated from the ethyl acetate extract of Syzygium aromaticum flower buds. Semisynthesis afforded both acetate and ester derivatives. The derived compoun...

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Bibliographic Details
Published in:Mediators of inflammation 2016-01, Vol.2016 (2016), p.1-9
Main Authors: Oyedeji, Adebola O., Aremu, Olukayode O., Oyedeji, Opeoluwa O., Rali, Sibusiso, Nkeh-Chungag, Benedicta N.
Format: Article
Language:English
Subjects:
Acids
Analgesics
Analgesics - chemistry
Animals
Anti-Inflammatory Agents - chemistry
Anti-inflammatory drugs
Biological Assay
Chromatography
Cloves
Female
Flowers - chemistry
Health aspects
Inflammation
Magnetic Resonance Spectroscopy
Male
Mass Spectrometry
Medicinal plants
Mice
Oleanolic Acid - chemical synthesis
Oleanolic Acid - chemistry
Pain
Pharmacology, Experimental
Plant Extracts - chemical synthesis
Plant Extracts - chemistry
R&D
Rats
Rats, Wistar
Research & development
Solubility
Solvents
Spectroscopy, Fourier Transform Infrared
Syzygium - chemistry
Temperature
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Summary:Oleanolic acid is a pentacyclic triterpenoid compound widely found in plants and well known for its medicinal properties. Oleanolic acid (OA) was isolated from the ethyl acetate extract of Syzygium aromaticum flower buds. Semisynthesis afforded both acetate and ester derivatives. The derived compounds were monitored with thin layer chromatography and confirmed with nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), Fourier infrared (FT-IR) spectroscopy, and melting point (Mp). All these compounds were evaluated for their analgesic and anti-inflammatory properties at a dose of 40 mg/kg. Significant analgesic and anti-inflammatory effects were noted for all OA-derived compounds. In the formalin-induced pain test, the derivatives showed better analgesic effects compared to their precursor, whereas, in the tale flick test, oleanolic acid proved to be superior in analgesic effects compared to all its derivatives with the exception of the acetyl derivative. Acute inflammatory tests showed that acetyl derivatives possessed better anti-inflammatory activity compared to the other compounds. In conclusion, semisynthesis of oleanolic acid yielded several derivatives with improved solubility and enhanced analgesic and anti-inflammatory properties.
ISSN:0962-9351
1466-1861
DOI:10.1155/2016/8401843