Synthesis of poinsettifolin A |
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Authors: | Zilma Escobar Carlos Solano Rikard Larsson Martin Johansson Efrain Salamanca Alberto Gimenez Eduardo Muñoz Olov Sterner |
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Institution: | 1. Center for Analysis and Synthesis, Department of Chemistry, Lund University, P.O. Box 124, SE-22100 Lund, Sweden;2. Instituto de Investigaciones Fármaco Bioquímicas, Universidad Mayor de San Andrés, P.O. Box 2932, La Paz, Bolivia;3. Instituto Maimónides de Investigación Biomédica de Córdoba (IMIBIC), Universidad de Córdoba, Avda. de Menendez Pidal s/n 14004, Córdoba, Spain |
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Abstract: | A synthesis of poinsettifolin A (1), a prenylated flavonol isolated from Dorstenia poinsettifolia, is described. Two routes starting from quercetin were explored, and 1 could be prepared if a prenyl group first was incorporated at C-6 of the protected quercetin followed by a condensation with citral at C-8. The key synthetic steps are a Mitsunobu reaction, an europium (III)-catalysed Claisen rearrangement coupled with cross-metathesis, and a benzopyran-forming geranylation. The two geranylated 3,5,3′,4′-tetrahydroxyflavonols prepared, 1 and 3, were assayed for antileishmanial activity against Leishmania amazonensis and Leishmania braziliensis, and found to be active. Compound 3 showed cytotoxic activity against leukaemia and lung cancer cells while 1 lacked cytotoxicity. |
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Keywords: | Prenylated flavonols Poinsettifolin A Leishmania amazonensis Leishmania braziliensis Cytotoxicity |
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