New Cytotoxic Tetrahydroprotoberberine-Aporphine Dimeric and Aporphine Alkaloids from<i>Corydalis turtschaninovii</i>

Kim, Ki‐Hyun; Piao, Cheng Jie; Choi, Sang Un; Son, Miwon; Lee, Kang Ro

doi:10.1055/s-0030-1249972

Cited by 20 publications

(9 citation statements)

References 24 publications

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“…The chemical shifts and the coupling patterns in the 1 H‐ and 13 C–NMR data corresponded to those of a protoberberine‐type alkaloid, dehydrocorydaline as shown in Fig. A (Kim et al ., ; Yhsw X, ), which has been previously isolated from Corydalis bulbosa (Kurahashi and Fujiwara, ).…”

Section: Methodsmentioning

confidence: 99%

Anti-Metastatic Effect of Dehydrocorydaline on H1299 Non-Small Cell Lung Carcinoma Cells via Inhibition of Matrix Metalloproteinases and B Cell Lymphoma 2

et al. 2017

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Though Dehydrocorydaline, an alkaloid isolated from Corydalis turtschaninovii tuber, was known to have anti-coronary artery disease, anti-inflammatory, apoptotic, anti-allergic, anti-acetylcholinesterase, and antitumor effects, the underlying anti-metastatic mechanism of Dehydrocorydalin was never elucidated in lung cancer cells so far. Thus, in the present study, the anti-metastatic effect of Dehydrocorydaline was examined in non-small cell lung carcinoma (NSCLC) cells, mainly targeting matrix metalloproteinases (MMPs) and B cell lymphoma-2 (Bcl-2) signaling. Here, Dehydrocorydaline exerted weak cytotoxicity and attenuated the protein expression of Bcl-2 and activated Bax in a concentration-dependent manner in NSCLC cells, such as A549, H460, H1299, and H596 cells. Also, Dehydrocorydaline suppressed the migration of H1299 cells by wound healing assay and transwell migration assay. Consistently, Dehydrocorydaline attenuated mRNA and protein levels of MMP7 and MMP9 as metastasis biomarkers in H1299 cells by quantitative reverse transcription polymerase chain reaction. Of note, Bcl-2 overexpression reduced the cytotoxic and anti-metastatic effects of Dehydrocorydaline on pCDNA-Bcl-2 transfected H1299 cells. Overall, our findings provide scientific evidence that Dehydrocorydaline exerts anti-metastatic potential via suppression of MMPs and Bcl-2 signaling in NSCLC cells. Copyright © 2017 John Wiley & Sons, Ltd.

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Section: Methodsmentioning

confidence: 99%

Anti-Metastatic Effect of Dehydrocorydaline on H1299 Non-Small Cell Lung Carcinoma Cells via Inhibition of Matrix Metalloproteinases and B Cell Lymphoma 2

et al. 2017

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“…Corydaline (>98%) was obtained from Wako Pure Chemical Industries, Ltd. (Osaka, Japan). Corybulbine, isocorybulbine, and yuanhunine were isolated from the tubers of Corydalis turtschaninovii using our previous method []. Nicotinamide adenine dinucleotide phosphate (NADP + ), glucose‐6‐phosphate, and glucose‐6‐phosphate dehydrogenase were obtained from Sigma Chemical Co. (St. Louis, MO, USA).…”

Section: Methodsmentioning

confidence: 99%

In vitro metabolism of corydaline in human liver microsomes and hepatocytes using liquid chromatography‐ion trap mass spectrometry

Lee

Kim

et al. 2012

J of Separation Science

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Corydaline is a pharmacologically active isoquinoline alkaloid isolated from Corydalis tubers. It exhibits the antiacetylcholinesterase, antiallergic, antinociceptive, and gastric emptying activities. The purposes of this study were to establish in vitro metabolic pathways of corydaline in human liver microsomes and hepatocytes by identification of their metabolites using liquid chromatography-ion trap mass spectrometry. Human liver microsomal incubation of corydaline in the presence of an NADPH-generating system resulted in the formation of nine metabolites, namely, four O-desmethylcorydaline [M1 (yuanhunine), M2 (9-O-desmethylcorydaline), M3 (isocorybulbine), and M4 (corybulbine)], three di-O-desmethylcorydaline [M5 (9,10-di-O-desmethylcorydaline), M6 (2,10-di-O-desmethylcorydaline), and M7 (3,10-di-O-desmethylcorydaline)], M8 (hydroxyyuanhunine), and M9 (hydroxycorydaline). Incubation of corydaline in human hepatocytes produced four metabolites including M1, M5, M6, and M9. O-Demethylation and hydroxylation were the major metabolic pathways for the metabolism of corydaline in human liver microsomes and hepatocytes.

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“…The molecular formula was determined to be C 18 C NMR data of 1 implied that compound 1 may be a trioxygenated aporphine-type alkaloid by the aforementioned evidence and reported literatures. [15][16][17][18] The structure of the aporphine-type skeleton was ultimately elucidated by the interpretation of the 1 H-1 H correlated spectroscopy (COSY), heteronuclear multiple quantum correlation (HMQC), and heteronuclear multiple bond correlation (HMBC) data. The HMQC spectrum permitted the correlation of all protonated carbons.…”

Section: Resultsmentioning

confidence: 67%

Alkaloids from Acorus gramineus rhizomes and their biological activity

Kang

Eom

et al. 2015

Planta Med

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Como parte de nossa pesquisa em andamento por constituintes bioativos de fontes medicinais coreanas, um fracionamento biomonitorado e uma investigação química de extrato metanólico de rizomas de Acorus gramineus resultaram no isolamento e identificação de dois alcaloides, incluindo um novo alcaloide do tipo aporfina, chamado gramichunosina e um alcaloide pirrol conhecido. Suas estruturas foram determinadas por uma combinação de análises espectroscópicas de ressonância magnética nuclear (NMR) 1D e 2D e espectrometria de massas de alta resolução (HRMS). Este é o primeiro relato de alcaloides de A. gramineus. Os compostos isolados apresentaram atividade antiproliferativa contra as linhagens de células A549, SK-OV-3, SK-MEL-2, e HCT-15 com EC 50 na faixa de 7,46-45,23 μM. Ademais, as atividades antineuroinflamatórias desses compostos foram determinadas através da medida dos níveis de óxido nítrico (NO) meio utilizando células de microglia murina BV-2. O composto gramichunosina inibiu a produção de NO em células BV-2 estimuladas com lipopolisacarídeo com valores de IC 50 de 7,83 μM.As part of our ongoing search for bioactive constituents from natural Korean medicinal resources, a bioassay-guided fractionation and a chemical investigation of the methanolic extract from the rhizomes of Acorus gramineus resulted in the isolation and identification of two alkaloids, including a new aporphine-type alkaloid, named gramichunosin, and a known pyrrole alkaloid. Their structures were determined by a combination of 1D and 2D nuclear magnetic resonance (NMR) spectroscopic analysis and high resolution mass spectrometry (HRMS). This is the first report of alkaloids from A. gramineus. The compounds isolated showed antiproliferative activities against A549, SK-OV-3, SK-MEL-2 and HCT-15 cell lines with EC 50 values in the range of 7.46-45.23 μM. Moreover, the anti-neuroinflammatory activities of these compounds were determined by measuring the nitric oxide (NO) levels in the medium using murine microglia BV-2 cells. Compound named gramichunosin inhibited NO production in lipopolysaccharide-stimulated BV-2 with IC 50 values of 7.83 μM.

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New Cytotoxic Tetrahydroprotoberberine-Aporphine Dimeric and Aporphine Alkaloids fromCorydalis turtschaninovii

Cited by 20 publications

References 24 publications

Anti-Metastatic Effect of Dehydrocorydaline on H1299 Non-Small Cell Lung Carcinoma Cells via Inhibition of Matrix Metalloproteinases and B Cell Lymphoma 2

Anti-Metastatic Effect of Dehydrocorydaline on H1299 Non-Small Cell Lung Carcinoma Cells via Inhibition of Matrix Metalloproteinases and B Cell Lymphoma 2

In vitro metabolism of corydaline in human liver microsomes and hepatocytes using liquid chromatography‐ion trap mass spectrometry

Alkaloids from Acorus gramineus rhizomes and their biological activity

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