Mass spectrometry of sauroxine, a Lycopodium alkaloid with AChE activity

D.A. CIFUENTE; M.G. VALLEJO; M.G. ORTEGA; J.L. CABRERA; C.E. TONN; A. M. AGNESE; C. ARDANAZ

Khartoum

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

NAPRECA

During the last years Lycopodium alkaloids have
gained a significant interest due to their unique skeletal characteristics as
well as due to their acetylcholinesterase activity. Is known that drugs that
inhibit acetylcholinesterase, can be used to treat early stages of Alzheimer
disease. Sauroxine was isolated from aerial
parts of Huperzia saururus (Lam.) Trevis. Electron ionization mass
spectrometry (EI-MS) (Low Resolution) and collision-induced dissociation
tandem mass spectrometry in time (CID-MS/MS) fragmentation was
conducted by an ion trap, GCQ Plus mass spectrometry with MS/MS. EIhigh-
resolution mass spectrometry (EI-HRMS) was performed in a
magnetic sector mass spectrometer Micromass VG. Using GC/EI-CID-MS/MS we obtained the different fragmentation routes that connect all the ionic populations. In addition, the
use of EI-HRMS allowed us to measure the exact masses of all the
fragment ions, and, with all this information gathered, we tried to establish
a fragmentation scheme concordant with the ascendant and descendant
species. The mass spectrometry study presented in this work
complete our mass studies of Lycopodium alkaloids. The mass
spectrometry work presented, has been very useful to confirm the
structural determination as well to support as the biogenetic relationships
between Lycopodium alkaloid lycodine-type: sauroxine.