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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| Format: | Article |
| Language: | English |
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Wiley
2016-01-01
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| Series: | Mediators of Inflammation |
| Online Access: | http://dx.doi.org/10.1155/2016/8401843 |
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| author | Sibusiso Rali Opeoluwa O. Oyedeji Olukayode O. Aremu Adebola O. Oyedeji Benedicta N. Nkeh-Chungag |
| author_facet | Sibusiso Rali Opeoluwa O. Oyedeji Olukayode O. Aremu Adebola O. Oyedeji Benedicta N. Nkeh-Chungag |
| author_sort | Sibusiso Rali |
| collection | DOAJ |
| description | 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. |
| format | Article |
| id | doaj-art-d3ed82e5a70d4febaf96bd1590100d1a |
| institution | Kabale University |
| issn | 0962-9351 1466-1861 |
| language | English |
| publishDate | 2016-01-01 |
| publisher | Wiley |
| record_format | Article |
| series | Mediators of Inflammation |
| spelling | doaj-art-d3ed82e5a70d4febaf96bd1590100d1a2025-02-03T06:12:55ZengWileyMediators of Inflammation0962-93511466-18612016-01-01201610.1155/2016/84018438401843Semisynthesis of Derivatives of Oleanolic Acid from Syzygium aromaticum and Their Antinociceptive and Anti-Inflammatory PropertiesSibusiso Rali0Opeoluwa O. Oyedeji1Olukayode O. Aremu2Adebola O. Oyedeji3Benedicta N. Nkeh-Chungag4Department of Chemistry, Faculty of Science and Agriculture, University of Fort Hare, Private Bag X1314, Alice 5700, South AfricaDepartment of Chemistry, Faculty of Science and Agriculture, University of Fort Hare, Private Bag X1314, Alice 5700, South AfricaDepartment of Human Biology, Faculty of Health Sciences, Walter Sisulu University, Private Bag X1, Mthatha 5117, South AfricaDepartment of Chemical and Physical Sciences, Faculty of Natural Sciences, Walter Sisulu University, Private Bag X1, Mthatha 5117, South AfricaDepartment of Biological and Environmental Science, Faculty of Natural Sciences, Walter Sisulu University, Private Bag X1, Mthatha 5117, South AfricaOleanolic 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.http://dx.doi.org/10.1155/2016/8401843 |
| spellingShingle | Sibusiso Rali Opeoluwa O. Oyedeji Olukayode O. Aremu Adebola O. Oyedeji Benedicta N. Nkeh-Chungag Semisynthesis of Derivatives of Oleanolic Acid from Syzygium aromaticum and Their Antinociceptive and Anti-Inflammatory Properties Mediators of Inflammation |
| title | Semisynthesis of Derivatives of Oleanolic Acid from Syzygium aromaticum and Their Antinociceptive and Anti-Inflammatory Properties |
| title_full | Semisynthesis of Derivatives of Oleanolic Acid from Syzygium aromaticum and Their Antinociceptive and Anti-Inflammatory Properties |
| title_fullStr | Semisynthesis of Derivatives of Oleanolic Acid from Syzygium aromaticum and Their Antinociceptive and Anti-Inflammatory Properties |
| title_full_unstemmed | Semisynthesis of Derivatives of Oleanolic Acid from Syzygium aromaticum and Their Antinociceptive and Anti-Inflammatory Properties |
| title_short | Semisynthesis of Derivatives of Oleanolic Acid from Syzygium aromaticum and Their Antinociceptive and Anti-Inflammatory Properties |
| title_sort | semisynthesis of derivatives of oleanolic acid from syzygium aromaticum and their antinociceptive and anti inflammatory properties |
| url | http://dx.doi.org/10.1155/2016/8401843 |
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