Reaction of acetaldehyde with 5-aminolevulinic acid via dihydropyrazine derivative.
When a solution of 5-aminolevulinic acid (ALA) was incubated with acetaldehyde at neutral pH, a product was generated. This product was identified as 3-ethylpyrazine-2,5-dipropanoic acid (ETPY). ETPY was stable at neutral pH. It has been reported that ALA dimerizes at neutral pH generating 3,6-dihydropyrazine-2,5-dipropanoic acid (DHPY), and subsequently resulting in pyrazine-2,5-dipropanoic acid (PY) by autoxidation. In the present reaction, DHPY generated from ALA reacted with acetaldehyde, resulting in ETPY. Preadministration of ALA 3 min prior to acetaldehyde injection supressed the toxicity of acetaldehyde in male mice. These results suggest that ALA may be useful as a scavenger for acetaldehyde.
School of Pharmacy, Shujitsu University.
Toshinori
T
Suzuki
Naoki
N
Yasuhara
Takashi
T
Ueda
Michiyo
M
Inukai
Mitsunobu
M
Mio
D000079:Acetaldehyde / Q000737:chemistry* / Q000633:toxicity; D000622:Aminolevulinic Acid / Q000737:chemistry* / Q000494:pharmacology; D000818:Animals; D002851:Chromatography, High Pressure Liquid; D019281:Dimerization; D004347:Drug Interactions; D064420:Drug-Related Side Effects and Adverse Reactions / Q000517:prevention & control; D006863:Hydrogen-Ion Concentration; D007928:Lethal Dose 50; D008297:Male; D013058:Mass Spectrometry; D051379:Mice; D008813:Mice, Inbred ICR; D011422:Propionates / Q000032:analysis* / Q000737:chemistry* / Q000378:metabolism; D011719:Pyrazines / Q000032:analysis* / Q000737:chemistry* / Q000378:metabolism
C449779:3,6-dihydropyrazine-2,5-dipropanoic acid; C000603225:3-ethylpyrazine-2,5-dipropanoic acid; D011422:Propionates; D011719:Pyrazines; D000622:Aminolevulinic Acid; D000079:Acetaldehyde