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The recent advances made in nitrofuran derivatives for use as antibacterial agents, especially as food preservatives, are reviewed. Antibacterial activity, in vitro, of nitrofuran derivatives newly synthesized in the past several years has been found to be comparatively large, although few new chemotherapeutic developments were found among these new nitrofuran derivatives.The nitrofuran derivatives having high antibacterial activity have such a tendency in their chemical structures that the vinyl group is connected at the 2 position of 5-nitrofuran rings. Examples of these nitrofuran derivatives and their antibacterial activity are show in Table 1.Nitrofurazone (F) and 5-nitro-2-furyl acryl amide (Z) which had been designated by the Welfare Ministry of Japan as food preservatives for fish sausage, fish ham, meat sausage, meat ham, kamaboko (fish cake), tofu (bean curd), an (bean jam), dried fish and fresh fish, and was effective until January 5,1966,after which 2-(2-furyl)-3-(5-nitro-2-furyl) acryl amide (AF-2) was designated as the preservative for fish sausage, fish ham, meat sausage, meat ham, barcon, kamaboko, tofu and an. AF-2 is one of the nitrofuryl vinyl substituted compounds.The antibacterial activity and preservative effects of AF-2 on various foods are reviewed briefly (Table 1,Fig. 1 and 2.).This recent investigation of nitrofuran as a food preservative has been made to clarify the changes of nitrofuran in food or foodstuffs, to find out the cause of these changes and to protect the nitrofuran from these changes. The decomposition of AF-2 and F in fish meat and in tofu are shown in Fig. 3,4,5 and 6. It was found that the cause of the decomposition was mainly from reduction caused by reducing materials such as the sulfhydryl group. (Table 3,4,5 and Fig. 7) The decomposition of nitrofuran derivatives by reducing agents also affected the pH value (Fig. 8 and Table 9), temperature (Fig. 9), meat pigment (Table 6,7 and 8), ferrous ion (Fig. 12) and chemical structures on nitrofuran derivatives.The interesting relationship between decomposition and chemical structure of nitrofuran derivatives is shown in Table 10. The stability of nitrofuran derivatives in cysteine solution is shown to depend upon meat protein.Finally, it was concluded that the preservative effect of nitrofuran derivatives in packaged and boiled food, such as fish sausage, was a product of its antibacterial activity and the remaining quantity of nitrofuran in that food.
社団法人日本生物工学会の論文
1966-08-25

防腐剤としてのニトロフラン誘導体に関する最近の知見

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