Anti-leishmanial activity of betulin derivatives

Sami Alakurtti, Pia Bergström, N. Sacerdoti-Sierra, C. L. Jaffe, J. Yli-Kauhaluoma (Corresponding Author)

    Research output: Contribution to journalArticleScientificpeer-review

    27 Citations (Scopus)

    Abstract

    Leishmanicidal activity of 24 derivatives of naturally occurring and abundant triterpenes belonging to the lupane series, betulin, betulinic acid and betulonic acid, is described in this study. The easily modified positions of the lupane skeleton, the hydroxy groups of C-3 and C-28, as well as the carbon–carbon double bond C-20–C-29 were used as a starting point to prepare a library of triterpenoid derivatives for bioactivity studies. The compounds were evaluated against Leishmania donovani axenic amastigotes on a microplate assay at 50 μM. GI50 values of the most effective compounds were evaluated, as well as their cytotoxicity on the human macrophage cell line THP-1, and anti-leishmanial activity against L. donovani-infected THP-1 macrophages was determined. Betulonic acid was the most potent derivative, yielding a GI50 value of 14.6 μM. Promising and distinct structure–activity relationships were observed, and these compounds can be regarded as significant lead molecules for further improvement and optimization.
    Original languageEnglish
    Pages (from-to)123-126
    Number of pages4
    JournalJournal of Antibiotics
    Volume63
    Issue number3
    DOIs
    Publication statusPublished - 2010
    MoE publication typeA1 Journal article-refereed

    Keywords

    • Antiprotozoal agents
    • Betulin
    • Betulinic acid
    • Leishmania sp.
    • Terpenoids

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