Bioassay-Guided Fractionation of Siparuna glycycarpa n-Butanol Extract with Inhibitory Activity against Influenza A(H1N1)pdm09 Virus by Centrifugal Partition Chromatography (CPC)

Abstract

Siparuna glycycarpa occurs in the Amazon region, and some species of this genus are used in Brazilian folk medicine. A recent study showed the inhibitory effect of this species against influenza A(H1N1)pdm09 virus, and in order to acquire active fractions, a polar solvent system n-butanol-methanol-water (9:1:10, v/v) was selected and used for bioassay-guided fractionation of n-butanol extract by centrifugal partition chromatography (CPC). The upper phase was used as stationary phase and the lower phase as mobile (descending mode). Among the collected fractions, the ones coded SGA, SGC, SGD, and SGO showed the highest antiviral inhibition levels (above 74%) at 100 µg·mL−1 after 24 h of infection. The bioactive fractions chemical profiles were investigated by LC-HRMS/MS data in positive and negative ionization modes exploring the Global Natural Products Social Molecular Networking (GNPS) platform to build a molecular network. Benzylisoquinoline alkaloids were annotated in the fractions coded SGA, SGC, and SGD collected during elution step. Aporphine alkaloids, O-glycosylated flavonoids, and dihydrochalcones in SGO were acquired with the change of mobile phase from lower aqueous to upper organic. Benzylisoquinolinic and aporphine alkaloids as well as glycosylated flavonoids were annotated in the most bioactive fractions suggesting this group of compounds as responsible for antiviral activity.

In Vitro and in Vivo Antimalarial Activity, Cytotoxicity and Phytochemical HRMS2 Profile of Plants from the Western Pará State, Brazilian Amazonia

“…Fragment ions detected in positive LC-HRMS 2 support the proposed structures of reticuline, coclaurine, isocorypalmine and anonaine (Figure 3) putatively identified as the major compounds in S. krukovii extract. This finding corroborates reports on LC-MS analyses applied to the aforementioned species, [24,25] as shown in Table S1.…”

Magnoflorine from Berberis vulgaris Roots—Impact on Hippocampal Neurons in Mice after Short-Term Exposure

“…Previously, the scientific literature delivered several examples of alkaloid purification. Nakonieczna et al [ 19 ] succeeded in the purification of isoquinoline alkaloids from Coptis chinensis ; benzylisoquinoline and aporphine alkaloids were recovered from Spirauna glycycarpa [ 20 ] using a polar solvent system composed of n-butanol-methanol-water (9:1:10, v / v ); O -tigloylcyclovirobuxeine-B was obtained via CPC fractionation of Buxus sempervirens extract with a hexane:EtOAc:MeOH:H2O (7:3:7:3) ( v/v/v/v ) solvent system [ 21 ], whereas aconitine was purified from Aconitum karacolicum by Tarbe et al [ 22 ]. In the case of this study, a composition of the following solvents: chloroform:methanol:water (4:3:3 v / v ), provided high purity MAG directly from the crude methanolic root extract of Berberis vulgaris .…”