Selected biological activities of saraines

New Structural Insights into Saraines A, B, and C, Macrocyclic Alkaloids from the Mediterranean Sponge Reniera (Haliclona) sarai

“…[8] In our test, bioactivity was observed to be considerably lower, probably due to a different susceptibility of the used strains on penicillin G sodium salt selected as control test (Table 2).…”

“…[8] In particular, the antibacterial effects of saraines A-C has already been studied by Caprioli et al, who reported that this activity could be affected by an optimal pH value of the experiments. [8] For saraines A-C, we have now evaluated the growth inhibition against Gram positive (Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus agalactiae and Bacillus subtilis) and Gram negative (Salmonella typhimurium, Klebsiella pneumoniae and Pseudomonas aeruginosa) bacterial strain, using the classical agar diffusion method. The results indicated no effect on Gram negative bacteria, but a selective inhibition for Gram positive ones, with the higher activity shown against S. agalactiae (Table 2).…”

“…The protonated zwitterionic form is thus expected to have lower activity. [a] Values by Caprioli et al [8] : saraine A (12.5), saraine B (25.0), saraine C (25.0), control test: Penicillin G sodium salt (0.04).…”

“…They exhibit grow inhibition of the fertilized sea urchin egg development, insecticidal/acaricidal effects, toxicity to Artemia salina, and antibacterial activity against Staphylococcus aureus, whose results indicated interest in future studies under selected controlled conditions. [8] Very recently, saraine 1 (1) was shown to have good antisettlement effect towards A. amphitrite cyprids. [9] We report here on new structural evidence concerning the amine aldehyde proximity effect, based on NMR spectroscopy and electrospray mass spectrometric analysis, supported by DFT calculations and by the investigation of its chemical reactivity.…”

“…They include saraine 1 (1), saraine 2 (2), saraine 3 (3), [1] isosaraine 1 (4), isosaraine 2, (5) and isosaraine 3 (6), [1,2] resulting in stereoisomers at the C-1 and C-9 centers by absolute configuration assignments, as well as saraine A (7), saraine B (8), and saraine C (9) [3] (Figure 1). X-ray analysis on the acetate derivative of saraine A allowed the relative position of the asymmetric centers to be defined, while the absolute configuration was established by Mosher's method.…”