Lycopodium Alkaloids from Phlegmariurus carinatus with Cytotoxic and Neuroprotective Effects

Chem Biodivers. 2023 Dec;20(12):e202301449. doi: 10.1002/cbdv.202301449. Epub 2023 Nov 29.

Abstract

One new fawcettimine-type alkaloid, phlecarinadine A (1), and twelve known ones (2-13) were isolated from the whole plant of Phlegmariurus carinatus. Their chemical structures were unambiguously established by extensive spectroscopic analyses, including nuclear magnetic resonance (NMR) spectroscopic and high resolution electrospray ionization mass spectrometry (HR-ESI-MS). The absolute configuration of 1 was elucidated by the electronic circular dichroism (ECD) technique. These compounds were tested for their cytotoxic and neuroprotective activities. None of these compounds revealed cytotoxic activity against five tumor cells. Phlegmariurine B (2) exhibited potential neuroprotective effects against hemin-induced HT22 cell damage, with a 17.76 % increase in cell survival at 10 μM. In further study, 2 can ameliorate hemin-induced neuronal cell death via an anti-apoptotic pathway. These findings suggest that 2 might be a valuable lead compound with neuroprotective activity.

Keywords: Huperziaceae; Lycopodium alkaloids; Phlegmariurus carinatus; cytotoxicity; neuroprotective activity.

MeSH terms

  • Alkaloids* / chemistry
  • Alkaloids* / pharmacology
  • Hemin
  • Lycopodium* / chemistry
  • Molecular Structure
  • Neuroprotective Agents* / pharmacology

Substances

  • Neuroprotective Agents
  • Hemin
  • Alkaloids