Department of Pharmacognosy, Graduate School of Pharmaceutical Science, Kyoto University, 46-29 Yoshida-Shimo-Adachi-cho, Sakyo-ku, Kyoto, 606-8501, Japan.
J Nat Med. 2020 Jan;74(1):189-199. doi: 10.1007/s11418-019-01363-y. Epub 2019 Oct 1.
The essential oil of perilla (Perilla frutescens) contains volatile low molecular weight compounds such as monoterpenes and phenylpropenes. The composition of the essential oil is classified into about ten chemotypes. The biosynthesis of these constituents is strictly controlled genetically. Among the compounds contained in perilla essential oil, the bioconversion of pure compounds such as perillaldehyde, limonene, and citral has been reported, but that of many other components has not. In addition, changes in the volatile components of raw plant material during brewing have also been investigated for wine and beer. In this study, we examined the bioconversion of perilla essential oil components by Saccharomyces cerevisiae during the brewing of liquor with perilla leaves. S. cerevisiae was added to the ethanol-water extract of dried leaves of P. frutescens and P. citriodora for seven essential oil types: perillaldehyde type, piperitenone type, perillene type, perillaketone type, elsholtziaketone type, citral type, and phenylpropanoid type. Volatile compounds in the reaction mixtures were analyzed by solid-phase microextraction (SPME)-GC-MS, revealing bioconversion of perillaldehyde, isoegomaketone, neral, and geranial by S. cerevisiae. Analysis of the conversion products suggests that they were formed by the reduction of C=C bonds and aldehydes, as well as by esterification and dehydration reactions.
紫苏（Perilla frutescens）精油含有挥发性低分子量化合物，如单萜类和苯丙素类。精油的组成可分为约十种化学型。这些成分的生物合成受到严格的遗传控制。在紫苏精油中含有的化合物中，已报道了纯化合物如紫苏醛、柠檬烯和柠檬醛的生物转化，但许多其他成分的生物转化尚未报道。此外，还研究了在酿造葡萄酒和啤酒过程中，原料植物挥发性成分的变化。在这项研究中，我们研究了在紫苏叶酿造白酒过程中，酿酒酵母对紫苏精油成分的生物转化。向紫苏（P. frutescens）和柠檬香蜂草（P. citriodora）干叶的乙醇-水提取物中添加酿酒酵母，对 7 种精油类型：紫苏醛型、胡椒酮型、紫苏烯型、紫苏酮型、埃尔舒尔茨酮型、柠檬醛型和苯丙素型进行了研究。通过固相微萃取（SPME）-GC-MS 分析反应混合物中的挥发性化合物，发现酿酒酵母可以将紫苏醛、异胡薄荷酮、橙花醛和牻牛儿醛进行生物转化。转化产物的分析表明，它们是通过 C=C 键和醛的还原以及酯化和脱水反应形成的。
