Preparative isolation of alkaloids from <i>Corydalis bungeana</i> Turcz. by high‐speed counter‐current chromatography using stepwise elution

Niu, Lili; Xie, Zenghong; Cai, Tao; Wu, Peng; Xue, Peng; Chen, Xiu-Lan; Wu, Zhi‐Yong; Ito, Yoichiro; Li, Famei; Yang, Fuchao

doi:10.1002/jssc.201000785

Cited by 36 publications

(20 citation statements)

References 22 publications

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“…The chemical components found in Kudiding include alkaloids, steroids, and flavonoid glycosides (Yang et al, 2014). Isoquinoline alkaloids are reportedly the major components occurring in the herb (Niu et al, 2011). Corynoline ( Fig.…”

Section: Introductionmentioning

confidence: 99%

In Vitro and In Vivo Characterization of Reactive Intermediates of Corynoline

2015

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Corynoline is a 1,3-benzodioxole-containing isoquinoline alkaloid isolated from Corydalis bugeana Turcz., a traditional herbal medicine. Corynoline has reportedly demonstrated multiple pharmacologic properties. Previous studies have also shown that corynoline induced cytotoxicity and inhibited cytochrome P450 (CYP) enzymes, but the mechanisms of the adverse effects remain unknown. The major objective of the present study was to identify reactive metabolites of corynoline responsible for the cytotoxicity and enzyme inhibition. Three oxidative metabolites (M1-M3) were detected by liquid chromatography-tandem mass spectrometry in rat liver microsomal incubations after exposure to corynoline. M1 and M2 were two isomers of catechol derivatives, and M3 was a dicatechol. The M1-M3 metabolites were also observed in urine of rats given corynoline. A total of four N-acetylcysteine (NAC) conjugates (M4-M7) were detected in microsomes containing corynoline, NAC, and NADPH. Apparently, M4 and M5 were derived from M1, M6 resulted from M2, and M7 was a M3-derived NAC conjugate. This indicates that corynoline was bioactivated to ortho-quinone derivatives. No corynoline-derived NAC conjugates (M4-M7) were detected in urine of rats given corynoline; however, three corresponding cysteinylglycine conjugates (M8-M10) were observed instead. Recombinant P450 enzyme incubations demonstrated that the CYPs 2C9, 3A4, and 2C19 were mainly involved in metabolic activation of corynoline. The metabolism study facilitates the understanding of corynoline-induced cytotoxicity and P450 enzyme inhibition.

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Section: Introductionmentioning

confidence: 99%

In Vitro and In Vivo Characterization of Reactive Intermediates of Corynoline

2015

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“… 152 Table S8, Supporting Information , summarizes 22 fractionation protocols including the use of two or three polarity-adjusted step gradients. 37 , 47 , 111 , 126 , 152 , 229 , 267 , 275 , 277 , 298 − 308 …”

Section: Workflowmentioning

confidence: 99%

Countercurrent Separation of Natural Products: An Update

et al. 2015

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This work assesses the current instrumentation, method development, and applications in countercurrent chromatography (CCC) and centrifugal partition chromatography (CPC), collectively referred to as countercurrent separation (CCS). The article provides a critical review of the CCS literature from 2007 since our last review (J. Nat. Prod.2008, 71, 1489–1508), with a special emphasis on the applications of CCS in natural products research. The current state of CCS is reviewed in regard to three continuing topics (instrumentation, solvent system development, theory) and three new topics (optimization of parameters, workflow, bioactivity applications). The goals of this review are to deliver the necessary background with references for an up-to-date perspective of CCS, to point out its potential for the natural product scientist, and thereby to induce new applications in natural product chemistry, metabolome, and drug discovery research involving organisms from terrestrial and marine sources.

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“…These methods require minimal equipment and operator training, but due to poor separation and reproducibility, isoquinoline alkaloids are not easily isolated using these methods. To circumvent this issue, high‐speed CCC has been employed for isolation . However, this method involves complex partition coefficient calculations and produces low separation efficiency; thus, it is only applicable to highly abundant constituents and permits their isolation from crude samples.…”

Section: Introductionmentioning

confidence: 99%

Preparative separation of isoquinoline alkaloids from Corydalis impatiens using a middle‐pressure chromatogram isolated gel column coupled with two‐dimensional liquid chromatography

Pan

Shen²,

et al. 2019

J of Separation Science

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We established a two-dimensional strong cation exchange/reversed-phase liquid chromatography protocol to isolate and purify isoquinoline alkaloids from Corydalis impatiens. Isoquinoline alkaloids were first enriched from a C. impatiens extract in which liposoluble components were removed using a medium-pressure chromatographic tower containing middle chromatogram isolated gel. A strong cation exchange column was employed to separate and obtain 30 fractions. We chose fractions 22-29 for reversed-phase liquid chromatography purification using characteristic isoquinoline alkaloid ultraviolet absorption spectra. Several isoquinoline alkaloid fractions (22-29) were further separated, and those of low resolution were isolated via two-dimensional liquid chromatography in the orthogonal plane. A total of eight novel isoquinoline alkaloids with characteristic ultraviolet spectra were obtained from C. impatiens. We thus demonstrate the benefits of off-line two-dimensional strong cation exchange/reversed-phase liquid chromatography to isolate isoquinoline alkaloids from C. impatiens.

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Preparative isolation of alkaloids from Corydalis bungeana Turcz. by high‐speed counter‐current chromatography using stepwise elution

Cited by 36 publications

References 22 publications

In Vitro and In Vivo Characterization of Reactive Intermediates of Corynoline

In Vitro and In Vivo Characterization of Reactive Intermediates of Corynoline

Countercurrent Separation of Natural Products: An Update

Preparative separation of isoquinoline alkaloids from Corydalis impatiens using a middle‐pressure chromatogram isolated gel column coupled with two‐dimensional liquid chromatography

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