Hydroxychavicol: a new anti-nitrosating phenolic compound from betel leaf.
Hydroxychavicol and eugenol are the phenolic compounds isolated from betel leaf (piper betel). The modulation of nitrosation of methylurea by sodium nitrite at pH 3.6 and 30 degrees C was studied. The formation of mutagenic N-nitrosomethylurea was monitored by checking the mutagenicity of reaction mixture in Salmonella typhimurium strain TA100 and TA1535 without S9 mix. Hydroxychavicol and eugenol exhibit dose-dependent suppression of nitrosation in vitro without affecting the survival of the bacteria. Pre- or post-treatment of bacterial cells from S. typhimurium strains TA100 and TA1535 with phenolics did not modify the mutagenicity of nitrosomethylurea. The blocking of hydroxy group(s) in the benzene ring by acetylation abolishes the anti-nitrosating activity of the molecule(s). The nitrosation inhibition by hydroxychavicol is through scavenging of nitrite ions in the media, thus making them non-available for the nitrosation of methylurea.
Nagabhushan
M
M
Carcinogenesis Division, Tata Memorial Centre, Parel, Bombay, India.
Amonkar
A J
AJ
Nair
U J
UJ
D'Souza
A V
AV
Bhide
S V
SV
D001114:Areca / Q000032:analysis*; D005054:Eugenol / Q000031:analogs & derivatives* / Q000302:isolation & purification / Q000494:pharmacology; D008770:Methylnitrosourea / Q000037:antagonists & inhibitors / Q000378:metabolism; D015394:Molecular Structure; D009152:Mutagenicity Tests; D009153:Mutagens; D009603:Nitroso Compounds / Q000378:metabolism*; D010946:Plants, Medicinal / Q000032:analysis*
D009153:Mutagens; D009603:Nitroso Compounds; C051268:2-hydroxychavicol; D005054:Eugenol; D008770:Methylnitrosourea