Electrospray Tandem Mass Spectrometric Study of a Furo-Furan Lactone in Heliotropium eichwaldi

Abstract

Detailed gas phase fragmentation behavior of a furo-furan lactone 1 with a novel skeleton of three fused furan rings isolated from medicinally important Heliotropium eichwaldi plant was studied. Elucidation of the major fragmentation routes was performed using CID-MS/MS analysis, insource-MSn fragmentation, parent ion scan analysis and exact mass measurements using electrospray ionization quadropole time-of-flight mass spectrometry (ESI-QqTOF-MS/ MS) hybrid instrument in negative and positive ion modes. Analysis showed the presence of [M+H]+ and [M-H]- at m/z 275 and m/z 273, respectively. Low-energy collision induced dissociation tandem mass spectrometric analysis (CIDMS/ MS) in both ion modes showed several characteristics losses of carbon monoxide and water molecules along with characteristic losses of acetaldehyde, formaldehyde, formic acid and carbondioxide. Moreover, compound 1 showed significant insource-MSn behavior during in-source fragmentation studies. LC-MS identification of 1 was performed in crude extract of H. eichwaldi. The knowledge of the fragmentation pattern and key fragment ions of furo-furan lactone, will be useful for further exploration of new members of this class of compounds in the H. eichwaldi and related species of family Boraginaceae utilizing very limited plant material.