Mass spectrometry of Sauroxine, a Lycopodium alkaloid with AChE inhibitory activity

CIFUENTE D; M VALLEJO; ORTEGA M,; CABRERA J,; TONN C; AGNESE A.M.,; ARDANAZ C

Khartoum

Simposio; The 15th Symposium of the Natural Products Research Network for Eastern and Central Africa (NAPRECA); 2013

During recent years, Lycopodium alkaloids have gained great interest due to their important pharmacological properties as well
as for their complex molecular architectures. Un important series of Lycopodium alkaloids isolated from Huperzia saururus
(Lam.) Trevis have been reported possessing important medicinal effects which can act either as potent inhibitors of
acetylcholinesterase (AChE) and/or on memory-related phenomena.
H. saururus (Lam.) Trevis. (Lycopodiaceae) ("cola de quirquincho", "piyiyay" or "piyijay") is a native Argentine species used in
the ethnomedicine as aphrodisiac and memory improver. Its habitat spreads from the northwest region of the country to the
sierras of the center (Cordoba) and south of Buenos Aires.
In previous investigations ten alkaloids were isolated from H. saururus. Also it was demonstrated by us that sauroine, the main
alkaloid present in the species, strongly enhances hippocampal Long Term Potentiation (LTP) as well as memory retention
demonstrated in vivo. At the same time it was not an inhibitor of the acetylcholinesterase enzyme. On contrary, sauroxine (other
majority alkaloid) was an acetylcholinesterase inhibitor but had no effect on LTP.
In the present work, using quadrupole ion trap (QIT)-MS instrument, we report and discuss the gas chromatography/electron
ionization mass spectrometry (GC/EIMS)
(low resolution) and collision-induced dissociation tandem
mass spectrometry (CIDMS/
MS) fragmentation of sauroxine (MS in time) a Likopodium alkaloids isolated from Huperzia
saururus (Lam.) Trevi. The
mass spectrometry studies presented in this rationale has been very useful to support the structural determination
of sauroxine and
Likopodium alkaloids analoges.