Applications of Direct Analysis in Real Time-Mass Spectrometry (DART-MS) in Allium Chemistry. (Z)-Butanethial S-Oxide and 1-Butenyl Thiosulfinates and Their S-(E)-1-Butenylcysteine S-Oxide Precursor from Allium siculum

0339574 - ÚCHP 2010 RIV US eng J - Journal Article
Kubec, R. - Cody, R.B. - Dane, A.J. - Musah, R.A. - Schraml, Jan - Vattekkatte, A. - Block, E.
Applications of Direct Analysis in Real Time-Mass Spectrometry (DART-MS) in Allium Chemistry. (Z)-Butanethial S-Oxide and 1-Butenyl Thiosulfinates and Their S-(E)-1-Butenylcysteine S-Oxide Precursor from Allium siculum.
Journal of Agricultural and Food Chemistry. Roč. 58, č. 2 (2010), s. 1121-1128. ISSN 0021-8561. E-ISSN 1520-5118
R&D Projects: GA AV ČR IAA400720706
Grant - others:NSF(US) CHE-0744578
Institutional research plan: CEZ:AV0Z40720504
Keywords : allium siculum * nectaroscordum * allium cepa
Subject RIV: CF - Physical ; Theoretical Chemistry
Impact factor: 2.816, year: 2010

L(Z)-Butanethial S-oxide isolated from the plant was shown to be identical to a synthetic sample. Its likely precursor, (R-S,R-C,E)-S-(1-butenyl)cysteine S-oxide (homoisoalliin), was isolated from homogenates of A. siculum, and a closely related species Allium tripedale, and fully characterized. Through use of LC-MS, a series of related gamma-glutamyl derivatives were tentatively identified in A. sicutum and A. tripedale homogenates, including gamma-glutamyl-(E)-S-(1-butenyl)cysteine and its S-oxide, gamma-glutamyl-S-butylcysteine and its S-oxide, and gamma-glutamyl-Smethylcysteine and its S-oxide. Because compounds containing the 1-butenyl group have not been previously identified in genus Allium species, this work extends the range of known Allium sulfur compounds, The general applicability of DART mass spectrometry in identifying naturally occurring, thermally fragile thial S-oxides and thiosulfinates is illustrated with onion, Allium cepa, as well as a plant from a different genus.
Permanent Link: http://hdl.handle.net/11104/0183061