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Synthesis and Detailed Examination of Spectral Properties of (S) and (R)-Higenamine 4'-O-beta-D-Glucoside and HPLC Analytical Conditions to Distinguish the Diastereomers

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Title: Synthesis and Detailed Examination of Spectral Properties of (S) and (R)-Higenamine 4'-O-beta-D-Glucoside and HPLC Analytical Conditions to Distinguish the Diastereomers
Authors: Kato, Eisuke Browse this author →KAKEN DB
Iwata, Ryohei Browse this author
Kawabata, Jun Browse this author →KAKEN DB
Keywords: higenamine
tetrahydroisoquinoline
β-adrenergic receptor agonist
diastereomer separation
Issue Date: 1-Sep-2017
Publisher: MDPI
Journal Title: Molecules
Volume: 22
Issue: 9
Start Page: 1450
Publisher DOI: 10.3390/molecules22091450
PMID: 28858255
Abstract: Higenamine is a tetrahydroisoquinoline present in several plants that has beta-adrenergic receptor agonist activity. Study of the biosynthesis of higenamine has shown the participation of norcoclaurine synthase, which controls the stereochemistry to construct the (S)-isomer. However, when isolated from nature, higenamine is found as the racemate, or even the (R)-isomer. We recently reported the isolation of higenamine 4'-O-beta-D-glucoside. Herein, its (R)- and (S)-isomers were synthesized and compared to precisely determine the stereochemistry of the isolate. Owing to their similar spectral properties, determination of the stereochemistry based on NMR data was considered inappropriate. Therefore, a high-performance liquid chromatography method was established to separate the isomers, and natural higenamine 4'-O-beta-D-glucoside was determined to be a mixture of isomers.
Rights: https://creativecommons.org/licenses/by/4.0/
Type: article
URI: http://hdl.handle.net/2115/67529
Appears in Collections:農学院・農学研究院 (Graduate School of Agriculture / Faculty of Agriculture) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 加藤 英介

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