Drug Designing: Open Access
Open Access

Identification of aconitine artefact in alcoholic extracts

International Conference and Expo on Drug Discovery & Designing

August 11-13, 2015 Frankfurt, Germany

Mai Ahmed

Scientific Tracks Abstracts: Drug Des

Abstract :

Aconitum napellus is a highly poisonous plant; all of its parts are rich in toxic C19-norditerpenoid alkaloids e.g. aconitine and
mesaconitine. General extraction procedures for aconitine and diester diterpenoid alkaloids require maceration in alcohols.
Mass spectra of A. napellus seed extracts show various alkaloidal contents. HPLCcombined with mass spectrometry was used to study
the stability of aconitine in methanol, followed by separation and identification of the main artefact whose formation could follow a
synchronous fragmentation. The HRMS data from A. napellus seed extracts, from methanol and acetone, showed the same alkaloidal
profile with an extra peak in the methanolic extract at m/z MH+ = 618.3271, MH+ of O-methyl-14-O-benzoylaconinerequires
618.3278. Its semi-synthesis was carried out by refluxing aconitine in methanol (6 h at 65oC). The suggested mechanism for the
formation of thisartefact is via a Grob-type fragmentation, cleavage of the C-7-C-17 bond with the nitrogen lone pair and C-7-
C17orientatedanti-parallel to the C-8-acetate bond, and then adding methanol back. TheNMR data of the HPLC purified artefact (10
mg) were compared with those of aconitine. Assigning the new O-methyl at C-8 followed from the chemical shift data, δH 3.14, 3.28,
3.28, 3.31 and 3.74 (each 3H, s) and δC 49.9, 55.0, 58.5, 59.1 and 62.4 (respectively), while in aconitine, four methoxy singlets appear
at δH 3.16, 3.26, 3.29 and 3.75, with associated carbon signals at δC 58.1, 56.1, 59.3 and 61.3. Quaternary C-8 resonates at δC 82.4 in
8-O-methyl-14-O-benzoylaconine and atδC 92.2 in (8-acetoxy) aconitine.

Biography :

Mai Ahmed completed her Master’s degree in Pharmaceutical Sciences at the age of 28 years from Assiut University, Egypt and worked there as an assistant lecturer. In
2011, she got a fully funded scholarship (for which we thank the Egyptian Government) and now she is a final year student in the Dept. of Pharmacy and Pharmacology,
University of Bath, UK.