| Title: | Synthesis of deuterium-labeled cinnamic acids: Understanding the volatile benzenoid pathway in the flowers of the Japanese loquat Eriobotrya japonica |
| Author(s): | Watanabe B; Nishitani S; Koeduka T; |
| Address: | "Institute for Chemical Research, Kyoto University, Kyoto, Japan. Graduate School of Sciences and Technology for Innovation, Yamaguchi University, Yamaguchi, Japan" |
| Journal Title: | J Labelled Comp Radiopharm |
| ISSN/ISBN: | 1099-1344 (Electronic) 0362-4803 (Linking) |
| Abstract: | "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-d(1) /Et(3) 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" |
| Keywords: | Cinnamates/*chemistry Deuterium/*chemistry Eriobotrya/*chemistry/metabolism Flowers/chemistry/metabolism Phenols/chemistry Volatile Organic Compounds/chemistry/*metabolism Eriobotrya japonica benzenoid volatiles biosynthesis cinnamic acids hydrogen-deuter; |
| Notes: | "MedlineWatanabe, Bunta Nishitani, Shiori Koeduka, Takao eng Research Support, Non-U.S. Gov't England 2021/07/10 J Labelled Comp Radiopharm. 2021 Aug; 64(10):403-416. doi: 10.1002/jlcr.3933. Epub 2021 Jul 20" |
