TY - JOUR
T1 - Pseudouridine, an antimutagenic substance in beer towards N-methyl-N′-nitro-N-nitrosoguanidine (MNNG)
AU - Yoshikawa, T.
AU - Kimura, S.
AU - Hatano, Tsutomu
AU - Okamoto, Keinosuke
AU - Hayatsu, H.
AU - Arimoto-Kobayashi, S.
N1 - Funding Information:
This work was supported in part by the Grant-in-Aid for Cancer Research (8-5) from the Ministry of Health, Labour and Welfare (for S.A.-K.).
PY - 2002
Y1 - 2002
N2 - Previously we reported that beer is antimutagenic against several food-derived mutagens including heterocyclic amines. We describe here the isolation and identification of pseudouridine from beer as an antimutagenic substance against N-methyl-N′-nitro-N-nitrosoguanidine (MNNG). All of the 17 samples of beer tested showed inhibition of the MNNG mutagenicity in Salmonella. Extensive fractionation through chromatography of the active components from a freeze-dried beer sample gave six antimutagenic fractions. One contained pseudouridine, as characterized by the UV spectra, nuclear magnetic resonance, and co-chromatography in HPLC. Pure pseudouridine inhibited the mutagenicity of MNNG in a dose-dependent manner. The amount of pseudouridine in the beer sample, estimated at about 0.4 mg/100 ml beer, can account for 3% of the total antimutagenicity of beer. Thus, the major active components in beer remain to be identified. The role of pseudouridine in inhibiting the mutagenicity of MNNG is to be studied further. Among analogs of pseudouridine, spongouridine, but not uridine, was antimutagenic against MNNG. The bacterial mutagenicity of another methylating agent N-methyl-N-nitrosourea was also inhibited by pseudouridine. Pseudouridine is the first example among nucleosides to be shown to possess an antimutagenic property.
AB - Previously we reported that beer is antimutagenic against several food-derived mutagens including heterocyclic amines. We describe here the isolation and identification of pseudouridine from beer as an antimutagenic substance against N-methyl-N′-nitro-N-nitrosoguanidine (MNNG). All of the 17 samples of beer tested showed inhibition of the MNNG mutagenicity in Salmonella. Extensive fractionation through chromatography of the active components from a freeze-dried beer sample gave six antimutagenic fractions. One contained pseudouridine, as characterized by the UV spectra, nuclear magnetic resonance, and co-chromatography in HPLC. Pure pseudouridine inhibited the mutagenicity of MNNG in a dose-dependent manner. The amount of pseudouridine in the beer sample, estimated at about 0.4 mg/100 ml beer, can account for 3% of the total antimutagenicity of beer. Thus, the major active components in beer remain to be identified. The role of pseudouridine in inhibiting the mutagenicity of MNNG is to be studied further. Among analogs of pseudouridine, spongouridine, but not uridine, was antimutagenic against MNNG. The bacterial mutagenicity of another methylating agent N-methyl-N-nitrosourea was also inhibited by pseudouridine. Pseudouridine is the first example among nucleosides to be shown to possess an antimutagenic property.
KW - Alkylating agents
KW - Antimutagen
KW - Beer
KW - Pseudouridine
KW - Spongouridine
UR - http://www.scopus.com/inward/record.url?scp=0036283199&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0036283199&partnerID=8YFLogxK
U2 - 10.1016/S0278-6915(02)00060-1
DO - 10.1016/S0278-6915(02)00060-1
M3 - Article
C2 - 12067579
AN - SCOPUS:0036283199
VL - 40
SP - 1165
EP - 1170
JO - Food and Chemical Toxicology
JF - Food and Chemical Toxicology
SN - 0278-6915
IS - 8
ER -