Prosojuliflavone and other constituents from Prosopis juliflora Swartz D.C (Fabaceae) and their chemotaxonomic importance

Abstract

The chemical investigation of ethyl acetate extracts of the roots and stem bark of Prosopis juliflora Swartz D.C (Fabaceae) led to the isolation of a new flavonoid, prosojuliflavone (1) and a new natural indole alkaloid dimer, N,N-Bis(2-(1H-indol-3-yl) ethyl) oxalamide (2) along with eight known compounds including three flavonoids, vitexin (3), a mixture of vitexin (3) and isovitexin (4), 4ʹ-O-methyl-ent-gallocathechin (5), two indole alkaloids, N-acetyltryptamine (6), tryptamine (7), a disaccharide, sucrose (8), two monoglycerides, hyloglyceride (9) and 1-(26-hydroxyhexacosanoyl)-glycerol (10). Their structures were elucidated by means of spectroscopic and spectrometric data, as well as by comparison with literature data. Compound 2 is described here for the first time as a natural product with complete 1H and 13C assignments. The antibacterial and antioxidant activities of the extracts and isolated compounds were evaluated. Compounds 1 and 5 (MIC = 8–64 μg/ml) were samples with most antibacterial activities while compound 1 (EC50 = 4.31 μg/mL; GEAC = 94.66 μg/mL) displayed the largest antioxidant activity. Interestingly, the tested samples showed bactericidal effects (MBC/MIC ≤4) with respect to sensitive bacteria. Compounds 1, 2, 6, 8 and 10 were isolated for the first time from the Fabaceae family. The chemotaxonomic significance of these compounds was also discussed. The overall results highlight the potential of P. juliflora as a sustainable source of antibacterial and antioxidant agents.