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Rothmanniamide and other constituents from the leaves of Rothmannia hispida (K.Schum.) fagerl. (Rubiaceae) and their chemophenetic significance
Affiliation:1. Department of Chemistry, Faculty of Science, University of Douala, P.O. Box 24157, Douala, Cameroon;2. Department of Organic Chemistry, Faculty of Science, University of Yaoundé I, P.O. Box 812, Yaoundé, Cameroon;3. Department of Chemistry, Higher Teacher Training College, University of Bamenda, P. O. Box 39, Bambili, Cameroon;4. Jodrell Laboratory, Natural Capital and Plant Health Department, Royal Botanic Gardens, Kew, Richmond, Surrey, TW9 3DS, United Kingdom;5. Department of Chemistry, Organic and Bioorganic Chemistry, Bielefeld University, D-33501 Bielefeld, Germany;6. Department of Chemistry, Inorganic and Structural Chemistry, Bielefeld University, D-33501 Bielefeld, Germany;7. Departmentof Chemistry, Higher Teacher Training College, University of Yaoundé I, P. O. Box 47, Yaoundé, Cameroon
Abstract:The chemical investigation of the CH2Cl2/MeOH (1:1) extract of the leaves of Rothmannia hispida (K. Schum.) Fagerl. (Rubiaceae) led to the isolation of a new ceramide rothmanniamide (1) and a naturally isolated alkyl cinnamate derivative n-heptadecyl-4-hydroxy-trans-cinnamate (2), along with fifteen known compounds including lupeol palmitate (3), lupeol (4), a mixture of uvaol (5) and erythrodiol (6), ursolic acid (7), 30-nor-2α,3β-dihydroxyurs-12-ene (8), hederagenin (9), stigmast-22-en-3-ol (10), a mixture of β-sitosterol (11) and stigmasterol (12), stigmast-4,22-dien-3-ol (13), stigmasterol 3-O-β-D-glucoside (14), triacontan-1-ol (15), kaempferol 3-O-β-D-glucopyranoside (16) and D-mannitol (17). Their structures were elucidated with the help of MS and NMR data. Compounds 8, 10 and 15 were isolated for the first time from the Rubiaceae family. The crude extract and the isolates were assessed in vitro for their antileishmanial activity against Leishmania donovani 1 S (MHOM/SD/62/1 S) promastigotes and cytotoxicity on RAW 264.7 macrophage cells. Compounds 7 and 8 exhibited a highly potent antileishmanial activity with IC50 values of 0.88 and 1.75 μg/mL, respectively, with good selectivity indexes (SI > 57). The chemophenetic significance of these compounds is also discussed.
Keywords:Rubiaceae  Chemophenetic significance  Rothmanniamide  Alkyl cinnamate  Antileishmanial
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