open access

https://hdl.handle.net/2115/67529

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

英語

diastereomer separation

2017-09-01

MDPI

Molecules

22(9)

1450

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.

学術雑誌論文

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Creative Commons Attribution 4.0 International

1420-3049