Elucidation of Absolute Configuration of Ophiorrhiside A by Comparison of ECD Spectra with That of Model Chiral Compound Having a 1,2,3,4-Tetrahydro-β-carbolin-3-one Skeleton

Kitajima, Mariko; Onozawa, Tadayoshi; Kogure, Noriyuki; Takayama, Hiromitsu

doi:10.3987/com-20-14351

HETEROCYCLES

2021

DOI: 10.3987/com-20-14351

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Elucidation of Absolute Configuration of Ophiorrhiside A by Comparison of ECD Spectra with That of Model Chiral Compound Having a 1,2,3,4-Tetrahydro-β-carbolin-3-one Skeleton

Mariko Kitajima¹,

Tadayoshi Onozawa²,

Noriyuki Kogure³

et al.

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Cited by 3 publications

References 26 publications

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Recent studies on chemical constituents of Ophiorrhiza plants

Kitajima

2022

J Nat Med

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Ophiorrhiza plants (Family Rubiaceae) are known to produce diverse monoterpenoid indole alkaloids including camptothecin with potent antitumor activity. This review contains a summary of recent chemical studies reported over the past 10 years regarding alkaloids (monoterpenoid indole and tetrahydroisoquinoline alkaloids, and cyclopeptide) in Ophiorrhiza plants. In addition, the alkaloid biosynthetic pathways based on their reported structures were proposed.

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Recent studies on chemical constituents of Ophiorrhiza plants

Kitajima

2022

J Nat Med

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New monoterpenoid indole alkaloids from Gelsemium elegans seeds

et al. 2022

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Resolution of Halogenated Mandelic Acids through Enantiospecific Co-Crystallization with Levetiracetam

Wang

Peng

2021

Molecules

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The resolution of halogenated mandelic acids using levetiracetam (LEV) as a resolving agent via forming enantiospecific co-crystal was presented. Five halogenated mandelic acids, 2-chloromandelic acid (2-ClMA), 3-chloromandelic acid (3-ClMA), 4-chloromandelic acid (4-ClMA), 4-bromomandelic acid (4-BrMA), and 4-fluoromandelic acid (4-FMA), were selected as racemic compounds. The effects of the equilibrium time, molar ratio of the resolving agent to racemate, amount of solvent, and crystallization temperature on resolution performance were investigated. Under the optimal conditions, the resolution efficiency reached up to 94% and the enantiomeric excess (%e.e.) of (R)-3-chloromandelic acid was 63%e.e.. All five halogenated mandelic acids of interest in this study can be successfully separated by LEV via forming enantiospecific co-crystal, but the resolution performance is significantly different. The results showed that LEV selectively co-crystallized with S enantiomers of 2-ClMA, 3-ClMA, 4-ClMA, and 4-BrMA, while it co-crystallized with R enantiomers of 4-FMA. This indicates that the position and type of substituents of racemic compounds not only affect the co-crystal configuration, but also greatly affect the efficiency of co-crystal resolution.

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Elucidation of Absolute Configuration of Ophiorrhiside A by Comparison of ECD Spectra with That of Model Chiral Compound Having a 1,2,3,4-Tetrahydro-β-carbolin-3-one Skeleton

Cited by 3 publications

References 26 publications

Recent studies on chemical constituents of Ophiorrhiza plants

Recent studies on chemical constituents of Ophiorrhiza plants

New monoterpenoid indole alkaloids from Gelsemium elegans seeds

Resolution of Halogenated Mandelic Acids through Enantiospecific Co-Crystallization with Levetiracetam

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