Identification of minor nitrosation products of the alkaloid gramine by mass spectrometry

The nitrosation of gramine, a tertiary amine alkaloid present in barley malt, was carried out by reaction with sodium nitrite in buffered acetic acid (pH 3.4) for 1 hr at room temperature. Following the previous isolation and identification of the major nitrosation products (Ahmad et al. Fd Chem. To...

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Published inFood and chemical toxicology Vol. 25; no. 11; pp. 867 - 870
Main Authors Ahmad, M.U., Libbey, L.M., Scanlan, R.A.
Format Journal Article
LanguageEnglish
Published Oxford Elsevier Ltd 01.11.1987
New York, NY Elsevier Science
Subjects
Alkaloids
Biological and medical sciences
Food toxicology
gramine
identification
Mass Spectrometry
Medical sciences
Nitrosamines
nitrosation
nitroso compounds
Sodium Nitrite
Toxicology
EI
CI
HPLC
NDMA
Barley
Alkaloid
Nitrosamine
Plant origin
Identification
Nitrosation
In vitro
Mass spectrometry
Food
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Summary:The nitrosation of gramine, a tertiary amine alkaloid present in barley malt, was carried out by reaction with sodium nitrite in buffered acetic acid (pH 3.4) for 1 hr at room temperature. Following the previous isolation and identification of the major nitrosation products (Ahmad et al. Fd Chem. Toxic. 1985, 23, 841), two minor products were isolated by HPLC and identified as indolin-3-one oxime and indole-3-aldehyde. Identification was based on mass spectrometry. The results give strong support to the hypothesis that gramine does not undergo nitrosation by nitrosative dealkylation.
Bibliography:ObjectType-Article-2
SourceType-Scholarly Journals-1
ObjectType-Feature-1
content type line 23
ISSN:0278-6915
1873-6351
DOI:10.1016/0278-6915(87)90266-3