title: 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.
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.
authors: Department of Pharmacognosy, University of Vienna, Althanstrasse 14, 1090 Vienna, Austria.
authors: Evelien
authors: E
authors: Rozema
authors: Ruxandra
authors: R
authors: Popescu
authors: Harald
authors: H
authors: Sonderegger
authors: Christian W
authors: CW
authors: Huck
authors: Johannes
authors: J
authors: Winkler
authors: Georg
authors: G
authors: Krupitza
authors: Ernst
authors: E
authors: Urban
authors: Brigitte
authors: B
authors: Kopp
mesh_terms: D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000494:pharmacology; D031057:Arisaema / Q000737:chemistry*; D001943:Breast Neoplasms; D045744:Cell Line, Tumor; D002942:Circular Dichroism; D004983:Ethanolamines / Q000737:chemistry* / Q000378:metabolism / Q000494:pharmacology; D005963:Glucosylceramides / Q000737:chemistry* / Q000378:metabolism; D057809:HEK293 Cells; D018922:HL-60 Cells; D006367:HeLa Cells; D006801:Humans; D006868:Hydrolysis; D008264:Macrophages; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D015394:Molecular Structure; D009753:Nutritive Value; D030021:Pinellia / Q000737:chemistry*; D027343:Rhizome / Q000737:chemistry; D021241:Spectrometry, Mass, Electrospray Ionization; D053719:Tandem Mass Spectrometry
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D004983:Ethanolamines; D005963:Glucosylceramides; C003337:sphingadienine