Bis-indole alkaloid caulerpin from a new source : isolation, characterization, anticancer activity, binding with nucleobases by DFT calculations and MD simulation.

Caulerpin, a bis-indole alkaloid is isolated from a new source , brown alga (family Sargassaceae) for the first time. The structure of caulerpin was characterized by IR, HNMR, C NMR, HSQC, HMBC, EI-MS spectroscopy. Antifungal results suggest that caulerpin has been inhibited (12 mm) and (7 mm) than other microbes. anticancer activity of caulerpin has been explored by cell viability assay against new human cancer cell line (liver-HepG2). The results show that caulerpin has low IC value (24.6 ± 2.1 µg/mL) against HepG-2. Based on the least toxic activity of caulerpin, these results encourage for future anticancer study. The binding of caulerpin molecule with the two nucleobases (T/U) bases has been studied by DFT methods. According to the AIM analysis, there are two types of interactions between caulerpin and T/U bases partially covalent partially electrostatic and electrostatic in gas and water phases. Based on NBO analysis, the charges were transferred from the lone-pair (n) in orbitals of O atoms of caulerpin to the σ* orbitals of T/U bases atoms. ΔE in the state of caulerpin-T bases complexes are lower than those in the caulerpin-U bases complexes in both gas and water phase. MD simulation supported that caulerpin-T/U bases complexes are stable in presence of explicit water phase. Thus, the findings of our study will be useful for giving an insight into the caulerpin/bases complexes that could be helpful in future experimental studies to develop the performance of caulerpin molecules as natural candidate drug. Communicated by Ramaswamy H. Sarma.