Graduate School of Engineering, Kitami Institute of Technology.
Graduate School of Science and Technology, Meiji University.
J Oleo Sci. 2023;72(11):1037-1048. doi: 10.5650/jos.ess23098.
Six optically active (Z)-7-decen-4-olide derivatives (1a-1f) were synthesized in 99% enantiomeric excess using diastereomeric resolution. The odour properties of the racemic and optically active 1a-1f were evaluated in terms of their orthonasal aromas. All of the stereoisomers had different odour characteristics and thresholds. Decen-4-olides (1a-1c) had a strong fruity note, whereas undecen-4-olide (1d and 1e) and dodecen-4-olide (1f) had a strong green note. For 7-alken-4-olides (1a, 1d, and 1f), the (R)-enantiomer had a lower odour threshold than the (S)-enantiomer. In contrast, no difference in the odour threshold was observed for the enantiomers of the 8-alken-4-olides (1b and 1e). Furthermore, the antimicrobial activity against Escherichia coli (E. coli; ATCC 25922) and Staphylococcus aureus (S. aureus; ATCC 29213) were investigated. Although the no differences in the antimicrobial activity of the stereoisomers was observed, 1d and 1e showed slight antimicrobial activity against E. coli, whereas only 1f showed antimicrobial activity against S. aureus. No antimicrobial activity was exhibited by (R)-1f, whereas (S)-1f exhibited strong antimicrobial activity.
使用非对映体拆分的方法，合成了 6 种光学活性（Z）-7-癸烯-4-内酯衍生物（1a-1f），其对映体过量值均为 99%。通过嗅闻评估了外消旋体和光学活性 1a-1f 的气味特性。所有立体异构体都具有不同的气味特征和阈值。癸烯-4-内酯（1a-1c）具有强烈的水果香气，而十一烯-4-内酯（1d 和 1e）和十二烯-4-内酯（1f）具有强烈的绿色调。对于 7-链烯-4-内酯（1a、1d 和 1f），（R）-对映异构体的气味阈值低于（S）-对映异构体。相比之下，8-链烯-4-内酯（1b 和 1e）的对映异构体的气味阈值没有差异。此外，还研究了它们对大肠杆菌（E. coli；ATCC 25922）和金黄色葡萄球菌（S. aureus；ATCC 29213）的抗菌活性。尽管立体异构体的抗菌活性没有差异，但 1d 和 1e 对大肠杆菌表现出轻微的抗菌活性，而只有 1f 对金黄色葡萄球菌表现出抗菌活性。（R）-1f 没有表现出抗菌活性，而（S）-1f 表现出很强的抗菌活性。
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