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Characterization of Glucocerebrosides and the Active Metabolite 4,8-Sphingadienine from Arisaema amurense and Pinellia ternata by NMR and CD Spectroscopy and ESI-MS/CID-MS

Author:
Rozema, Evelien, Popescu, Ruxandra, Sonderegger, Harald, Huck, Christian W., Winkler, Johannes, Krupitza, Georg, Urban, Ernst, Kopp, Brigitte
Source:
Journal of agricultural and food chemistry 2012 v.60 no.29 pp. 7204-7210
ISSN:
1520-5118
Subject:
Arisaema, Pinellia ternata, apoptosis, cell proliferation, cytotoxicity, digestive system, dissociation, eggplants, foods, hydrolysis, mass spectrometry, metabolites, nuclear magnetic resonance spectroscopy, rhizomes, silica gel, sphingolipids, spinach
Abstract:
Sphingolipid metabolites regulate cellular processes such as cell proliferation, differentiation, and apoptosis. In this study, glucocerebrosides (GluCer) from rhizomes of Arisaema amurense and Pinellia ternata were fully characterized using 1- and 2-dimensional nuclear magnetic spin resonance (NMR) and circular dichroism (CD) spectroscopy and tandem collision-induced dissociation mass spectrometry (ESI-MS/CID-MS). Three new acylated and seven known GluCer were elucidated with 4,8-sphingadienine (4,8-SD, d18:2) as backbone. 4,8-SD is a metabolite after enzymatical hydrolysis of GluCer in the gut lumen. In this study, 4,8-SD was hydrolyzed from GluCer and chromatographically purified on silica gel. In contrast to the GluCer, 4,8-SD showed cytotoxic effects in the WST-1 assay. GluCer with 4,8-SD as sphingoid backbone are present in plants consumed as food, such as spinach, soy, and eggplant.
Agid:
314588