Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity

Kim, Ki‐Hyun; Lee, Il Kyun; Piao, Cheng Jie; Choi, Sang Un; Lee, Jei Hyun; Kim, Yeong Shik; Lee, Kang Ro

doi:10.1016/j.bmcl.2010.06.035

Cited by 30 publications

(20 citation statements)

References 27 publications

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“…44 Berberine, a related compound to COP, manifested inhibition of cell proliferation through apoptosis in different cell lines. 21,[45][46][47] Flow cytometric analysis delineated COP-induced apoptosis as a dose-dependent process.…”

Section: Discussionmentioning

confidence: 99%

Coptisine-induced cell cycle arrest at G2/M phase and reactive oxygen species–dependent mitochondria-mediated apoptosis in non-small-cell lung cancer A549 cells

et al. 2017

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This study aimed to explore the effect of coptisine on non-small-cell lung cancer and its mechanism through various in vitro cellular models (A549). Results claimed significant inhibition of proliferation by coptisine against A549, H460, and H2170 cells with IC 50 values of 18.09, 29.50, and 21.60 µM, respectively. Also, coptisine exhibited upregulation of pH2AX, cell cycle arrest at G2/M phase, and downregulation of the expression of cyclin B1, cdc2, and cdc25C and upregulation of p21 dose dependently. Furthermore, induction of apoptosis in A549 cells by coptisine was characterized by the activation of caspase 9, caspase 8, and caspase 3, and cleavage of poly adenosine diphosphate ribose polymerase. In addition, coptisine was found to increase reactive oxygen species generation, upregulate Bax/Bcl-2 ratio, disrupt mitochondrial membrane potential, and cause cytochrome c release into the cytosol. Besides, treatment with a reactive oxygen species inhibitor (N-acetyl cysteine) abrogated coptisine-induced growth inhibition, apoptosis, reactive oxygen species generation, and mitochondrial dysfunction. Thus, the mediation of reactive oxygen species in the apoptosisinduced effect of coptisine in A549 cells was corroborated. These findings have offered new insights into the effect and mechanisms of action of coptisine against non-small-cell lung cancer.

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Section: Discussionmentioning

confidence: 99%

Coptisine-induced cell cycle arrest at G2/M phase and reactive oxygen species–dependent mitochondria-mediated apoptosis in non-small-cell lung cancer A549 cells

et al. 2017

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“…Nine authentic alkaloids included in the major components of C . species were either purchased from various chemical companies – isocorydine, corydaline, and palmatine from Sigma Aldrich (Steinheim, Germany); berberine from Wako Chemicals (Osaka, Japan; purity, >99%); and tetrahydropalmatine from ChromaDex (Irvine, CA, USA) – or isolated by a previously reported method – glaucine, coptisine, canadine, and tetrahydrocoptisine. Purities of the authentic alkaloids were determined by HPLC/diode‐array detection (DAD) (purity, >95%).…”

Section: Methodsmentioning

confidence: 99%

“…In previous studies, the fragmentation behaviors of alkaloids have been intensively investigated using MS/MS to specify the structural patterns. To date, there have been limited studies on the specific alkaloids in Corydalis tuber . Moreover, identification of the bio‐active alkaloids in C .…”

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confidence: 99%

Identification of structurally diverse alkaloids in Corydalis species by liquid chromatography/electrospray ionization tandem mass spectrometry

Jeong

Lee

et al. 2012

Rapid Comm Mass Spectrometry

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RATIONALE Alkaloids with significant therapeutic effects are the main active constituents of Corydalis (C.) species. There are several kinds of alkaloids in C. species associated with diverse alkaloid metabolism in plants, but they are rarely identified. This study aimed to identify diverse alkaloids in C. species by liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI‐MS/MS). METHODS Several types of alkaloids were extracted from C. species using ultrasonication with 70% CH3OH, and the extract was partitioned at pH 2 and 12. Separation of alkaloids was achieved by C18 high‐performance liquid chromatography (HPLC), and MS/MS analysis was conducted by electrospray ionization triple‐quadrupole mass spectrometry. For further confirmation, LC/Fourier transform ion cyclotron resonance (FTICR)‐MS was used to obtain accurate mass data and gas chromatography (GC)/MS combined with trimethylsilyl derivatization was applied for identification of the minor alkaloids. RESULTS Thirty‐three alkaloids among three different C. species were successfully separated and identified by LC/ESI‐MS/MS and LC/FTICR‐MS. Structural assignment of individual alkaloids was performed according to MS/MS spectral patterns. For further confirmation, accurate mass data of alkaloids by LC/FTICR‐MS were obtained within 5 ppm and the GC/MS data for the trimethylsilyl alkaloids were also obtained. Among 33 alkaloids identified from this study, 13 alkaloids were reported for the first time in the investigated C. species. CONCLUSIONS The LC/ESI‐MS/MS technique was effective in obtaining structural information and yielded diagnostic ions for diverse alkaloids. Based on the identified 33 alkaloids, marker compounds were suggested for the three C. species with different geographic origins. This study may also be useful for elucidating unknown alkaloids in herbal medicines. Copyright © 2012 John Wiley & Sons, Ltd.

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“…Each subfraction was then tested for biological activity. Selected subfractions were further chromatographed on an RP-C 18 silica gel (230-400 mesh, 200 g) column as described in ( 20 ) and eluted with methanol-water (2:3 → 1:0, gradient system) to yield six fractions (A-F). Fraction D (560 mg) was subjected to silica gel column chromatography (CC) (CHCl 3 -methanol, 17:1) to yield six subfractions (D1-D6).…”

Section: Extraction and Isolationmentioning

confidence: 99%

“…Butein is a potent novel anti-adipogenic compound. A: C3H10T1/2 cells were differentiated in the presence of various concentrations (1,5,10,20, and 40 M) of butein, genistein, and resveratrol for 7 days . B: Differentiated cells were stained with Oil Red O, and lipid accumulation was quantifi ed by measuring the extracted dye at 520 nm.…”

Section: Identifi Cation Of Butein As a Novel Anti-adipogenic Compoundmentioning

confidence: 99%

Butein is a novel anti-adipogenic compound

Song

Yoon

Kim

et al. 2013

Journal of Lipid Research

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Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity

Cited by 30 publications

References 27 publications

Coptisine-induced cell cycle arrest at G2/M phase and reactive oxygen species–dependent mitochondria-mediated apoptosis in non-small-cell lung cancer A549 cells

Coptisine-induced cell cycle arrest at G2/M phase and reactive oxygen species–dependent mitochondria-mediated apoptosis in non-small-cell lung cancer A549 cells

Identification of structurally diverse alkaloids in Corydalis species by liquid chromatography/electrospray ionization tandem mass spectrometry

Butein is a novel anti-adipogenic compound

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