Synthesis and Biological Activity of -Methylene--lactones as New
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- 作者：Mitsuo Miyazawa ; Hiroshi Shimabayashi ; Shuichi Hayashi ; Seiji Hashimoto ; Sei-ichi Nakamura ; Hiroshi Kosaka ; and Hiromu Kameoka
- 刊名：Journal of Agricultural and Food Chemistry
- 出版年：2000
- 出版时间：November 2000
- 年：2000
- 卷：48
- 期：11
- 页码：5406 - 5410
- 全文大小：71K
- 年卷期：v.48,no.11(November 2000)
- ISSN：1520-5118
文摘
Seven kinds of 
-methylene-
-lactones with an alkyl group at the C-4 position were synthesizedaccording to a previously described method, with yields of 28-34%. These -methylene--lactoneshad characteristic and unique odors. All -methylene--lactones added a roast-like odor to materials.The antimicrobial effects of -methylene--lactones were investigated by using a paper disk diffusionmethod. The results showed the -methylene--lactones inhibited the growth of three bacteria(Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescens) and two fungi (Saccharomyces cerevisiae and Aspergillus niger). In particular, -methylene--undecalactone and -methylene--dodecalactone exhibited potent inhibition of the growth of these microorganisms compared to butylp-hydroxybenzoate as standard antibiotic. The umu test revealed that the -methylene--lactonessuppressed the SOS-inducing activity of three mutagens, furylfuramide, UV irradiation, and Trp-P-1, respectively. The antimicrobial effects and the suppressive effects of SOS induction by-methylene--lactones had a tendency to intensify as the number of carbons in the side chainincreased.Keywords: -Methylene--lactones; odor; antimicrobial activity; SOD-like activity; umu test
-methylene--lactones with an alkyl group at the C-4 position were synthesizedaccording to a previously described method, with yields of 28-34%. These -methylene--lactoneshad characteristic and unique odors. All -methylene--lactones added a roast-like odor to materials.The antimicrobial effects of -methylene--lactones were investigated by using a paper disk diffusionmethod. The results showed the -methylene--lactones inhibited the growth of three bacteria(Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescens) and two fungi (Saccharomyces cerevisiae and Aspergillus niger). In particular, -methylene--undecalactone and -methylene--dodecalactone exhibited potent inhibition of the growth of these microorganisms compared to butylp-hydroxybenzoate as standard antibiotic. The umu test revealed that the -methylene--lactonessuppressed the SOS-inducing activity of three mutagens, furylfuramide, UV irradiation, and Trp-P-1, respectively. The antimicrobial effects and the suppressive effects of SOS induction by-methylene--lactones had a tendency to intensify as the number of carbons in the side chainincreased.Keywords: -Methylene--lactones; odor; antimicrobial activity; SOD-like activity; umu test