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Molecules 2017, 22(9), 1450; doi:10.3390/molecules22091450

Synthesis and Detailed Examination of Spectral Properties of (S) and (R)-Higenamine 4′-O-β-d-Glucoside and HPLC Analytical Conditions to Distinguish the Diastereomers

Laboratory of Food Biochemistry, Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita-ku, Sapporo, Hokkaido 060-8589, Japan
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Received: 17 August 2017 / Revised: 30 August 2017 / Accepted: 31 August 2017 / Published: 31 August 2017
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Abstract

Higenamine is a tetrahydroisoquinoline present in several plants that has β-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-β-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-β-d-glucoside was determined to be a mixture of isomers. View Full-Text
Keywords: higenamine; tetrahydroisoquinoline; β-adrenergic receptor agonist; diastereomer separation higenamine; tetrahydroisoquinoline; β-adrenergic receptor agonist; diastereomer separation
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Kato, E.; Iwata, R.; Kawabata, J. Synthesis and Detailed Examination of Spectral Properties of (S) and (R)-Higenamine 4′-O-β-d-Glucoside and HPLC Analytical Conditions to Distinguish the Diastereomers. Molecules 2017, 22, 1450.

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