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

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Abstract

Acetylation and methylation semisynthesis of oleanolic acid (OA) isolated from Syzygium aromaticum L. yielded two compounds: 3-acetoxyoleanolic acid (3-AOA) and 3-acetoxy, 28-methylester oleanolic acid (3-A,28-MOA). Anti-inflammatory properties of these compounds were assessed using the serotonin and fresh egg albumin-induced inflammatory test models in male Wistar rats weighing 250–300 g. Furthermore, erythrocyte membrane-stabilizing property of these compounds was evaluated in the heat- and hypotonicity-induced in vitro hemolysis test models. The two semisynthetic compounds significantly (p < 0.05) inhibited albumin-induced inflammation better than OA and indomethacin from 1–5 h post administration. Both compounds were membrane stabilizing in heat-induced hemolysis test while only 3-AOA showed membrane-stabilizing effects in a hypotonic milieu. Semisynthesis of OA yielded two compounds which had better in vivo anti-inflammatory and in vitro membrane-stabilizing properties.

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Acknowledgments

This work was supported by the Walter Sisulu University Institutional Research Grant, the Govan Mbeki Research and Development Center, University of Fort Hare, and the National Research Foundation (NRF).

Conflict of Interest

All authors declare that they have no conflict of interest.

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Authors and Affiliations

  1. Department of Zoology, Faculty of Science, Engineering & Technology, PB X1, Mthatha, 5117, Eastern Cape Province, South Africa

    Benedicta N. Nkeh-Chungag

  2. Department of Chemistry, Faculty of Science and Agriculture, University of Fort Hare, PB X1314, Alice, 5700, Eastern Cape Province, South Africa

    Opeoluwa O. Oyedeji

  3. Department of Chemistry and Chemical Technology, Faculty of Science, Engineering & Technology, PB X1, Mthatha, 5117, Eastern Cape Province, South Africa

    Adebola O. Oyedeji

  4. Department of Physiology, Faculty of Health Science, PB X1, Mthatha, 5117, Eastern Cape Province, South Africa

    Eugene J. Ndebia

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  1. Benedicta N. Nkeh-Chungag
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  2. Opeoluwa O. Oyedeji
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  4. Eugene J. Ndebia
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Correspondence to Benedicta N. Nkeh-Chungag.

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Nkeh-Chungag, B.N., Oyedeji, O.O., Oyedeji, A.O. et al. Anti-Inflammatory and Membrane-Stabilizing Properties of Two Semisynthetic Derivatives of Oleanolic Acid. Inflammation 38, 61–69 (2015). https://doi.org/10.1007/s10753-014-0007-y

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  • DOI: https://doi.org/10.1007/s10753-014-0007-y

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