Synthesis and biological activity of alpha-methylene-gamma-lactones as new aroma chemicals.
Seven kinds of alpha-methylene-gamma-lactones with an alkyl group at the C-4 position were synthesized according to a previously described method, with yields of 28-34%. These alpha-methylene-gamma-lactones had characteristic and unique odors. All alpha-methylene-gamma-lactones added a roast-like odor to materials. The antimicrobial effects of alpha-methylene-gamma-lactones were investigated by using a paper disk diffusion method. The results showed the alpha-methylene-gamma-lactones inhibited the growth of three bacteria (Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescens) and two fungi (Saccharomyces cerevisiae and Aspergillus niger). In particular, alpha-methylene-gamma-undecalactone and alpha-methylene-gamma-dodecalactone exhibited potent inhibition of the growth of these microorganisms compared to butyl p-hydroxybenzoate as standard antibiotic. The umu test revealed that the alpha-methylene-gamma-lactones suppressed 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 alpha-methylene-gamma-lactones had a tendency to intensify as the number of carbons in the side chain increased.
Miyazawa
M
M
Department of Applied Chemistry, Faculty of Science and Engineering, Kinki University, Kowakae, Higashiosaka-shi, Osaka 577-8502, Japan. miyazawa@apch.kindai.ac.jp
Shimabayashi
H
H
Hayashi
S
S
Hashimoto
S
S
Nakamura
S
S
Kosaka
H
H
Kameoka
H
H
D000473:Alkanes / Q000737:chemistry; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001234:Aspergillus niger / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D009812:Odorants; D011551:Pseudomonas fluorescens / Q000187:drug effects; D013014:SOS Response, Genetics / Q000187:drug effects; D012441:Saccharomyces cerevisiae / Q000187:drug effects; D013211:Staphylococcus aureus / Q000187:drug effects; D013329:Structure-Activity Relationship; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000473:Alkanes; D000900:Anti-Bacterial Agents; D000890:Anti-Infective Agents; D007783:Lactones; D013729:Terpenes