- Synthesis of deuterium-labeled cinnamic acids: Understanding the volatile benzenoid pathway in the flowers of the Japanese loquat Eriobotrya japonica
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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/Et3N 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.
- Koeduka, Takao,Nishitani, Shiori,Watanabe, Bunta
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p. 403 - 416
(2021/08/09)
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- Metabolic analysis of the cinnamate/monolignol pathway in Carthamus tinctorius seeds by a stable-isotope-dilution method
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The present study established a system for comprehensive metabolic analysis of the cinnamate/monolignol and lignan pathways by the use of a stable-isotope-dilution method. The system was successfully applied to characterization of the pathways in Carthamu
- Sakakibara, Norikazu,Nakatsubo, Tomoyuki,Suzuki, Shiro,Shibata, Daisuke,Shimada, Mikio,Umezawa, Toshiaki
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p. 802 - 815
(2008/03/27)
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- Identification of dehydro-ferulic acid-tyrosine in rye and wheat: Evidence for a covalent cross-link between arabinoxylans and proteins
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To monitor chemical reactions between ferulate and proteins during breadmaking, 8-14C-(E)-ferulic acid-(D-galactopyranose-6′-yl) ester was synthesized as a radiotracer and added to wheat and rye flour prior to breadmaking. Breads were lyophiliz
- Piber, Michael,Koehler, Peter
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p. 5276 - 5284
(2007/10/03)
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