Rothmanniamide and other constituents from the leaves of Rothmannia hispida (K.Schum.) fagerl. (Rubiaceae) and their chemophenetic significance.

The chemical investigation of the CH 2 Cl 2 /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 -2 α, 3 β -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 IC 50 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. Image 1 • New secondary metabolites in Rothmannia hispida (K. Schum.) Fagerl. (Rubiaceae). • Three compounds were isolated for the first time from the Rubiaceae family. • Antileishmanial compounds from R. hispida. • The chemophenetic significance of the isolated compounds was discussed. [ABSTRACT FROM AUTHOR]