Experimentation with a physiomimic system and kinetic analysis exhibited four distinct reaction phases in LDL glycation despite of the type of inducer: glucose or glyoxal. LDL glycation was more sensitive to a status of hyperglycemia (such as 400 mg glucose/100 mL) as evidenced by the reaction order of 0.53. Glucose reacted intensively in the Initial Phase (reaction period 0-2h) which was identified to result from a parallel mechanism involving both the direct Schiff's product formation and the auto-oxidative cleavages. In contrast, a physiological level of glyoxal revealed merely a reaction order of only 0.09, implicitly indicating a far less sensitive glycation which can be attributed to a mechanism proceeding simply through a molecular Schiff's reaction. On treatment with Psidium guajava L. aqueous extract (PE) (0.01-0.625 mg/mL), a rather unique and significant inhibitory characteristic on LDL glycation was observed with a dose-dependent manner. We attributed such an effect of PE to its distinct abundance of polyphenolic content (165.61+/-10.39 mggallic acid equivalent (GAE)/g). Conclusively, PE is an excellent anti-LDL glycative agent whose potential therapeutic uses can be extended to the prevention of a variety of cardiovascular and neurodegenerative diseases associated with glycations.