1H NMR-guided isolation of hasubanan alkaloids from the alkaloidal extract of Stephania longa

1H NMR-guided fractionation led to the isolation of 16 alkaloids from the alkaloidal extract of Stephania longa, including 11 new hasubanan alkaloids (1-11) and five known alkaloids (12-16). Interestingly, compounds 2 and 11 are typically considered protonated tertiary amine compounds, whereas compounds 1 and 10 are regarded as oxidized versions of the corresponding compounds. Their gross structures were determined through an extensive analysis of spectroscopic data (NMR (nuclear magnetic resonance) and HRESIMS (high resolution electrospray ionization mass spectroscopy)), and their absolute configurations were established by comparing their experimental and calculated electronic circular dichroism (ECD) spectra. The new (3) and a known (12) compounds in all isolates displayed stronger antineuroinflammatory effects (IC50 values of 1.8 and 11.1 & mu;M, respectively) than minocycline (IC50 value of 15.5 & mu;M) against NO production on LPS-activated BV2 cells.

Automated summary

16 alkaloids, including 11 new hasubanan alkaloids and five known alkaloids, were isolated from the alkaloidal extract of Stephania longa through 1H NMR-guided fractionation. The structures were determined by spectroscopic analysis, and the absolute configurations were established by comparing experimental and calculated ECD spectra. Compound 3 and compound 12 showed stronger antineuroinflammatory effects than minocycline against NO production on LPS-activated BV2 cells.