Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 58, Issue 2, Pages 1121-1128Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jf903733e
Keywords
Allium siculum; Nectaroscordum; Allium cepa; Petiveria alliacea; DART mass spectrometry; butanethial S-oxide; S-(1-butenyl)cysteine S-oxide; structure elucidation; homoisoalliin; lachrymatory sulfines
Funding
- NSF [CHE-0744578]
- Ministry of Education of the Czech Republic [MSM16007665806]
- Grant Agency of CAS [IAA 400720706]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [0744578] Funding Source: National Science Foundation
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Lachrymatory (Z)-butanethial S-oxide along with several 1-butenyl thiosulfinates was detected by DART mass spectrometry upon cutting Allium siculum, a popular ornamental Allium species used in some cultures as a spice. (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, Petiveria alliacea.
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