Formation of tetrahydroharman (1-methyl-1,2,3,4-tetrahydro-beta-carboline) by Helicobacter pylori in the presence of ethanol and tryptamine.
Helicobacter pylori contains alcohol dehydrogenase which oxidizes ethanol to acetaldehyde. In the present study, H. pylori cytosol was incubated in a buffered media at pH 6.0 and 7.4 in the presence of ethanol and tryptamine. Under these conditions, tetrahydroharman (1-methyl-tetrahydro-beta-carboline) was produced as a condensation product of tryptamine and acetaldehyde. At pH 6.0, 20.60 +/- 5.00% of the added tryptamine was converted to tetrahydroharman, while 27.00 +/- 4.80% (mean +/-SD) was converted at pH 7.4. Similar reactions between acetaldehyde and other dietary amines seem likely. Such biogenic alkaloids, if formed in vivo, might contribute to the dysphoric effects of alcohol.
Callaway
J C
JC
Department of Pharmaceutical Chemistry, University of Kuopio, Finland.
Airaksinen
M M
MM
Salmela
K S
KS
Salaspuro
M
M
D000079:Acetaldehyde / Q000032:analysis; D002851:Chromatography, High Pressure Liquid; D000431:Ethanol / Q000494:pharmacology*; D006246:Harmaline / Q000031:analogs & derivatives* / Q000032:analysis / Q000378:metabolism; D016480:Helicobacter pylori / Q000378:metabolism*; D013056:Spectrophotometry, Ultraviolet; D014363:Tryptamines / Q000494:pharmacology*
D014363:Tryptamines; C023426:tetrahydroharmane; D000431:Ethanol; C030820:tryptamine; D006246:Harmaline; D000079:Acetaldehyde