Alkaloids from the hook-bearing branch of Uncariarhynchophylla and their neuroprotective effects against glutamate-induced HT22 cell death

J Asian Nat Prod Res. 2014;16(8):876-83. doi: 10.1080/10286020.2014.918109. Epub 2014 Jun 5.

Abstract

One new alkaloid, 4-geissoschizine N-oxide methyl ether (1), was isolated from the EtOH extract of the hook-bearing branch of Uncariarhynchophylla, together with 10 known alkaloids, 3-epi-geissoschizine methyl ether (2) isolated from U.rhynchophylla for the first time, geissoschizine methyl ether (3), 4-hirsuteine N-oxide (4), hirsuteine (5), hirsutine (6), 3α-dihydro-cadambine (7), 3β-isodihydro-cadambine (8), cadambine (9), strictosamide (10), and akuammigine (11). The structures were elucidated by spectroscopic methods including UV, ESI-QTOF MS, NMR, and circular dichroism experiments. Neuroprotective effects of 1-9 were investigated against 3 mM glutamate-induced HT22 cell death. The activity assay showed that 2, 3, 5, and 6 exhibited potent neuroprotective effects against glutamate-induced HT22 cell death. However, only weak neuroprotective activities were observed for 1, 4, 7, 8, and 9.

Keywords: HT22 cells; Uncariarhynchophylla; glutamate; indole alkaloids; neuroprotection.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkaloids / chemistry
  • Alkaloids / isolation & purification
  • Alkaloids / pharmacology*
  • Cell Death / drug effects
  • Cell Survival / drug effects
  • Drugs, Chinese Herbal / chemistry
  • Drugs, Chinese Herbal / isolation & purification
  • Drugs, Chinese Herbal / pharmacology*
  • Glutamic Acid / pharmacology*
  • Indole Alkaloids / chemistry
  • Indole Alkaloids / isolation & purification*
  • Indole Alkaloids / pharmacology*
  • Molecular Structure
  • Neuroprotective Agents / chemistry
  • Neuroprotective Agents / isolation & purification*
  • Neuroprotective Agents / pharmacology*
  • Nuclear Magnetic Resonance, Biomolecular
  • Uncaria / chemistry*

Substances

  • 4-geissoschizine N-oxide methyl ether
  • Alkaloids
  • Drugs, Chinese Herbal
  • Indole Alkaloids
  • Neuroprotective Agents
  • geissoschizine methylether
  • hirsuteine
  • Glutamic Acid
  • hirsutine