Anti-Inflammatory and Membrane-Stabilizing Properties of Two Semisynthetic Derivatives of Oleanolic Acid

Nkeh-Chungag, Benedicta N.; Oyedeji, Opeoluwa O.; Oyedeji, Adebola O.; Ndebia, Eugene Jamot

doi:10.1007/s10753-014-0007-y

Cited by 27 publications

(20 citation statements)

References 23 publications

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“…Recently, OA was documented as a promising lead compound for new drug formulation [ 21 ]. Indeed, Habila et al [ 22 ] demonstrate the improvement of antibacterial effect of OA by decorating C 3 position hydroxy group with an acetyl group while Nkeh-Chungag et al [ 14 ] demonstrated improved analgesic and anti-inflammatory properties by semisynthesis of OA. The present study corroborates the fact that modification of OA in C 3 and C 28 positions results in enhancement of biological properties.…”

Section: Discussionmentioning

confidence: 99%

“…Hence, several studies have been designed to modify the structure of OA with the hope of improving its physical properties for better bioavailability to enhance its bioactivity. Moreover, it is clearly demonstrated that the chemical structure of oleanolic acid has three “active” sites, the C 3 hydroxy, the C 12 to C 13 double bond, and the C 28 carboxylic acid [ 7 , 13 , 14 ], which may be chemically modified and thus change its physical and pharmacological effects.…”

Section: Introductionmentioning

confidence: 99%

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Semisynthesis of Derivatives of Oleanolic Acid fromSyzygium aromaticumand Their Antinociceptive and Anti-Inflammatory Properties

Rali

Oyedeji

Aremu

et al. 2016

Mediators of Inflammation

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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.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Semisynthesis of Derivatives of Oleanolic Acid fromSyzygium aromaticumand Their Antinociceptive and Anti-Inflammatory Properties

Rali

Oyedeji

Aremu

et al. 2016

Mediators of Inflammation

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“…Liu et al showed that OA could inhibit the generation of the inflammatory factors TNF- α and IL-6 [ 31 ]. Nkeh-Chungag et al found that OA exerted potent anti-inflammatory effects by inhibiting NO and PGE2 in RAW 264.7 cells [ 32 ]. Our results showed that OA decreased the levels of IL-6 and TNF- α in insulin-resistant HepG2 cells ( Figure 3 ).…”

Section: Discussionmentioning

confidence: 99%

Oleanolic Acid Attenuates Insulin Resistance via NF-κB to Regulate the IRS1-GLUT4 Pathway in HepG2 Cells

Han

Bei

et al. 2015

Evidence-Based Complementary and Alternative Medicine

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The aim of our study is to elucidate the mechanisms of oleanolic acid (OA) on insulin resistance (IR) in HepG2 cells. HepG2 cells were induced with FFA as the insulin resistance model and were treated with OA. Then the glucose content and the levels of tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) were analyzed. Moreover, protein expression of nuclear factor kappa B (NF-κB), insulin receptor substrate 1(IRS1), and glucose transporter 4 (GLUT4) in cells treated with OA were measured by Western blot analysis. Additionally, IRS1 protein expression exposed to OA was detected after using pyrrolidine dithiocarbamate (PDTC).Our results revealed that OA decreased the glucose content in HepG2 cells in vitro. Moreover, OA reduced the levels of TNF-α and IL-6 and upregulated IRS1 and GLUT4 protein expression. Furthermore, OA also reduced NF-κB protein expression in insulin-resistant HepG2 cells. After blocking NF-κB, the expression of IRS1 protein had no obvious changes when treated with OA. OA attenuated insulin resistance and decreased the levels of TNF-α and IL-6. Meanwhile, OA decreased NF-κB protein expression and upregulated IRS1 and GLUT4 protein expression. Therefore, regulating the IRS1-GLUT4 pathway via NF-κB was the underlying mechanism of OA on insulin resistance.

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“…In the past three decades, OA has been used in Chinese medicine for the treatment of liver disorders, including viral hepatitis. In vitro and in vivo studies have demonstrated that OA possesses potent antioxidant activities (15,16), and anti-inflammatory effects (17), which contribute toward its potential protective effects. However, whether OA exerts protective effects against renal I/R injury, and the possible underlying mechanism, Attenuation of renal ischemia/reperfusion injury by oleanolic acid preconditioning via its antioxidant, anti-inflammatory, and anti-apoptotic activities remain unclear.…”

Section: Introductionmentioning

confidence: 99%

Attenuation of renal ischemia/reperfusion injury by oleanolic acid preconditioning via its antioxidant, anti-inflammatory, and anti-apoptotic activities

Long

Yang

et al. 2016

Molecular Medicine Reports

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Ischemia/reperfusion (I/R)‑associated acute kidney injury is a major clinical problem in both native and transplanted kidneys. Renal I/R, and subsequent renal injury, may be attributed to oxidative stress, inflammation, and apoptosis. Oleanolic acid (OA) is a natural product, which possesses antioxidant, anti‑inflammatory, and anti‑apoptotic activities. The present study aimed to examine the effects of OA preconditioning on renal I/R and the possible underlying mechanisms. In a renal I/R model, rats were administered OA (12.5, 25 and 50 mg/kg) for 15 consecutive days prior to bilateral renal I/R induction. Serum samples and kidneys were then collected and stored for subsequent determination. The results of the present study demonstrated that OA significantly and dose‑dependently attenuated I/R‑induced renal damage. OA prevented renal I/R injury, as evidenced by decreased levels of blood urea nitrogen, creatinine, kidney injury molecule‑1 and lactate dehydrogenase. In addition, OA defended against oxidative stress, as reflected by decreased levels of methane dicarboxylic aldehyde, increased activities of superoxide dismutase, catalase and glutathione peroxidase, and increased glutathione (GSH) levels. Levels of proinflammatory cytokines, interferon‑γ, interleukin (IL)‑6) and myeloperoxidase, were also reduced by OA, whereas the anti‑inflammatory cytokine IL‑10 was increased. Furthermore, OA prevented I/R‑induced apoptotic cell death, and prevented decreases in the mRNA expression levels of nuclear factor erythroid 2‑related factor 2 (Nrf2) and γ‑glutamylcysteine ligase (GCLc). Conversely, buthionine sulphoximine attenuated the protective effects of OA on renal I/R injury. These results indicated that OA preconditioning may prevent I/R‑induced renal damage via antioxidant, anti‑inflammatory, and anti‑apoptotic activities. Stabilization of Nrf2/GCLc signaling and subsequent maintenance of the GSH pool is critical for the protective effects of OA against renal I/R injury. The present study reported a novel therapeutic strategy for the treatment of renal I/R injury.

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Anti-Inflammatory and Membrane-Stabilizing Properties of Two Semisynthetic Derivatives of Oleanolic Acid

Cited by 27 publications

References 23 publications

Semisynthesis of Derivatives of Oleanolic Acid fromSyzygium aromaticumand Their Antinociceptive and Anti-Inflammatory Properties

Semisynthesis of Derivatives of Oleanolic Acid fromSyzygium aromaticumand Their Antinociceptive and Anti-Inflammatory Properties

Oleanolic Acid Attenuates Insulin Resistance via NF-κB to Regulate the IRS1-GLUT4 Pathway in HepG2 Cells

Attenuation of renal ischemia/reperfusion injury by oleanolic acid preconditioning via its antioxidant, anti-inflammatory, and anti-apoptotic activities

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