Synthesis of deuterium-labeled cinnamic acids: Understanding the volatile benzenoid pathway in the flowers of the Japanese loquat Eriobotrya japonica.
Synthesis of deuterium-labeled cinnamic acids: Understanding the volatile benzenoid pathway in the flowers of the Japanese loquat Eriobotrya japonica.
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DOI：
10.1002/jlcr.3933
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发表时间：
2021-07
影响因子：
1.8
通讯作者：
Bunta Watanabe;Shiori Nishitani;T. Koeduka
中科院分区：
文献类型：
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作者：
Bunta Watanabe;Shiori Nishitani;T. Koeduka
肉桂酸广泛分布于植物中，包括供人类使用的作物，并表现出多种有益于人类健康的活性。它们还在苯丙素类如木质素、花青素、类黄酮和香豆素的生物合成中占据关键地位。在这方面，氘标记的肉桂酸已被用作食品和药物化学以及植物生物化学中的示踪剂和内标。因此，非常需要简洁地合成氘标记的肉桂酸。在这项研究中，我们合成了氘标记的肉桂酸使用容易获得的氘源。我们还研究了乙醇-d1/Et 3 N体系中的氢-氘交换反应。该方法可以在酚羟基的邻位和帕拉以及肉桂酸烷基酯的C-2位引入氘原子，适用于各种酚类化合物。使用合成的标记化合物，我们证明，苯型挥发物，如4-甲氧基苯甲醛，在日本枇杷花的气味是生物合成苯丙氨酸通过肉桂酸和4-香豆酸。这项研究提供了容易获得的各种氘标记的（聚）酚，以及有用的工具，研究肉桂酸在生活系统中的代谢。
Cinnamic acids are widely distributed in plants, including crops for human use, and exhibit a variety of activities that are beneficial to human health. They also occupy a pivotal position in the biosynthesis of phenylpropanoids such as lignins, anthocyanins, flavonoids, and coumarins. In this context, deuterium-labeled cinnamic acids have been used as tracers and internal standards in food and medicinal chemistry as well as plant biochemistry. Therefore, a concise synthesis of deuterium-labeled cinnamic acids would be highly desirable. In this study, we synthesized deuterium-labeled cinnamic acids using readily available deuterium sources. We also investigated a hydrogen-deuterium exchange reaction in an ethanol-d1 /Et3 N system. This method can introduce deuterium atoms at the ortho and para positions of the phenolic hydroxy groups as well as at the C-2 position of alkyl cinnamates, and is applicable to various phenolic compounds. Using the synthesized labeled compounds, we demonstrated that the benzenoid volatiles, such as 4-methoxybenzaldehyde, in the scent of the flowers of the Japanese loquat Eriobotrya japonica are biosynthesized from phenylalanine via cinnamic and 4-coumaric acids. This study provides easy access to a variety of deuterium-labeled (poly)phenols, as well as to useful tools for studies of the metabolism of cinnamic acids in living systems.