Статті в журналах: "Coptisine"

1

Zhou, Yan, Chunxiu Zhou, Xutao Zhang, Chi Teng Vong, Yitao Wang, and Wai San Cheang. "Coptisine Attenuates Diabetes—Associated Endothelial Dysfunction through Inhibition of Endoplasmic Reticulum Stress and Oxidative Stress." Molecules 26, no. 14 (July 11, 2021): 4210. http://dx.doi.org/10.3390/molecules26144210.

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Coptisine is the major bioactive protoberberine alkaloid found in Rhizoma Coptidis. Coptisine reduces inflammatory responses and improves glucose tolerance; nevertheless, whether coptisine has vasoprotective effect in diabetes is not fully characterized. Conduit arteries including aortas and carotid arteries were obtained from male C57BL/6J mice for ex vivo treatment with risk factors (high glucose or tunicamycin) and coptisine. Some arterial rings were obtained from diabetic mice, which were induced by high-fat diet (45% kcal% fat) feeding for 6 weeks combined with a low-dose intraperitoneal injection of streptozotocin (120 mg/kg). Functional studies showed that coptisine protected endothelium-dependent relaxation in aortas against risk factors and from diabetic mice. Coptisine increased phosphorylations of AMPK and eNOS and downregulated the endoplasmic reticulum (ER) stress markers as determined by Western blotting. Coptisine elevates NO bioavailability and decreases reactive oxygen species level. The results indicate that coptisine improves vascular function in diabetes through suppression of ER stress and oxidative stress, implying the therapeutic potential of coptisine to treat diabetic vasculopathy.

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2

Fu, Shuilian, Saihong Ni, Danni Wang, and Tie Hong. "Coptisine Suppresses Mast Cell Degranulation and Ovalbumin-Induced Allergic Rhinitis." Molecules 23, no. 11 (November 21, 2018): 3039. http://dx.doi.org/10.3390/molecules23113039.

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Coptisine is one of the main components of isoquinoline alkaloids in the coptidis rhizome. The effect of coptisine on allergic rhinitis has not been investigated. In this study, we report the effects and mechanisms of coptisine using monoclonal anti-2,4,6-dinitrophenyl-immunoglobulin (Ig) E/human serum albumin (DNP-IgE/HSA)-stimulated rat basophilic leukemia cells (RBL-2H3 cells) in vitro and an ovalbumin (OVA)-induced allergic rhinitis (AR) in mice. The results showed that coptisine markedly decreased the levels of β-hexosaminidase, histamine, interleukin (IL)-4, and tumor necrosis factor (TNF)-α. Coptisine also prevented morphological changes, such as restoring an elongated shape, inhibiting granule release on toluidine blue staining, and reorganizing inhibited filamentous actins (F-actin). Additionally, coptisine blocked the phosphorylation of phosphoinositide3-kinase (PI3K)/Akt (as known as protein kinase B(PKB)) in RBL-2H3 cell. Furthermore, the results showed that coptisine suppressed OVA-induced allergic rhinitis symptoms, such as nasal rubbing and OVA-specific IgE, and histamine, IL-4 and TNF-α levels in the serum of AR mice. These data suggested that coptisine should have inhibitory effects on the inflammatory responses of mast cells, and may be beneficial for the development of coptisine as a potential anti-allergic drug.

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3

Nguyen, Ly Thi Huong, Min-Jin Choi, Heung-Mook Shin, and In-Jun Yang. "Coptisine Alleviates Imiquimod-Induced Psoriasis-like Skin Lesions and Anxiety-like Behavior in Mice." Molecules 27, no. 4 (February 19, 2022): 1412. http://dx.doi.org/10.3390/molecules27041412.

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Psoriasis is a common inflammatory skin disorder, which can be associated with psychological disorders, such as anxiety and depression. This study investigated the efficacy and the mechanism of action of a natural compound coptisine using imiquimod (IMQ)-induced psoriasis mice. Coptisine reduced the severity of psoriasis-like skin lesions, decreased epidermal hyperplasia and the levels of inflammatory cytokines TNF-α, IL-17, and IL-22. Furthermore, coptisine improved IMQ-induced anxiety in mice by increasing the number of entries and time in open arms in the elevated plus maze (EPM) test. Coptisine also lowered the levels of inflammatory cytokines TNF-α and IL-1β in the prefrontal cortex of psoriasis mice. HaCaT keratinocytes and BV2 microglial cells were used to investigate the effects of coptisine in vitro. In M5-treated HaCaT cells, coptisine decreased the production of IL-6, MIP-3α/CCL20, IP-10/CXCL10, and ICAM-1 and suppressed the NF-κB signaling pathway. In LPS-stimulated BV2 cells, coptisine reduced the secretion of TNF-α and IL-1β. These findings suggest that coptisine might be a potential candidate for psoriasis treatment by improving both disease severity and psychological comorbidities.

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4

Gong, Li-Li, Lian-Hua Fang, Hai-Lin Qin, Yang Lv, and Guan-Hua Du. "Analysis of the Mechanisms Underlying the Vasorelaxant Action of Coptisine in Rat Aortic Rings." American Journal of Chinese Medicine 40, no. 02 (January 2012): 309–20. http://dx.doi.org/10.1142/s0192415x12500243.

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The aim of the present study was to evaluate the vasorelaxant effects of coptisine and its possible mechanisms in isolated rat aortic rings. Coptisine was evaluated on isolated rat aortic rings precontracted with norepinephrine (NE) and KCl. The mechanisms were evaluated in the presence or absence of specific pharmacological inhibitors. Coptisine (1 ~ 200 μM) relaxed NE (1 μM) or KCl (60 mM) induced sustained contraction with pEC50 values of 4.49 ± 0.48 and 4.85 ± 0.57 in a concentration dependent manner. Pretreatment with coptisine (10, 50 or 100 μM) also inhibited concentration-response curves to NE and KCl. The vasorelaxant effect of coptisine was attenuated significantly by endothelium removal, and incubation with Nω-nitro-L-arginine methyl ester (L-NAME, 100 μM), methylene blue (10 μM) and indomethacin (5 μM) partially reduced the vasorelaxant effect of coptisine. In endothelium-denuded rings, the vasorelaxant effect of coptisine was reduced significantly by 4-aminopyridine (4-AP, 100 μM), but not glibenclamide (10 μM) ortetraethylammonium (TEA, 5 mM). Coptisine also reduced NE-induced transient contraction in Ca2+ -free solution, and inhibited contraction induced by increasing external calcium in Ca2+ -free medium plus 60 mM KCl. It was concluded that coptisine induced both endothelium-dependent and -independent relaxation in rat aortic rings. The NO-cGMP mediated pathway may be involved in the endothelium-dependent relaxation and in the activation of voltage-dependent K+ channels, contributing in part to the endothelium-independent relaxation bycoptisine. Coptisine also blocks extracellular Ca2+ influx by interacting with both voltage- and receptor-operated Ca2+ channels.

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5

Rao, Poorna Chandra, Sajeli Begum, Mahendra Sahai, and D. Saketh Sriram. "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." Tumor Biology 39, no. 3 (March 2017): 101042831769456. http://dx.doi.org/10.1177/1010428317694565.

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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 IC50 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 apoptosis-induced 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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6

Kim, So Young, Hyun Hwangbo, Hyesook Lee, Cheol Park, Gi-Young Kim, Sung-Kwon Moon, Seok Joong Yun, Wun-Jae Kim, Jaehun Cheong, and Yung Hyun Choi. "Induction of Apoptosis by Coptisine in Hep3B Hepatocellular Carcinoma Cells through Activation of the ROS-Mediated JNK Signaling Pathway." International Journal of Molecular Sciences 21, no. 15 (July 31, 2020): 5502. http://dx.doi.org/10.3390/ijms21155502.

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Hepatocellular carcinoma (HCC) has a high mortality rate worldwide, and treatment is very limited due to its high recurrence and low diagnosis rate, and therefore there is an increasing need to develop more effective drugs to treat HCC. Coptisine is one of the isoquinoline alkaloids, and it has various pharmacological effects. However, the evidence for the molecular mechanism of the anticancer efficacy is still insufficient. Therefore, this study investigated the antiproliferative effect of coptisine on human HCC Hep3B cells and identified the action mechanism. Our results showed that coptisine markedly increased DNA damage and apoptotic cell death, which was associated with induction of death receptor proteins. Coptisine also significantly upregulated expression of proapoptotic Bax protein, downregulated expression of anti-apoptotic Bcl-2 protein, and activated caspase-3, -8, and -9. In addition, coptisine remarkably increased the generation of reactive oxygen species (ROS), loss of mitochondrial membrane potential (MMP), and release of cytochrome c into the cytoplasm. However, N-acetylcysteine (NAC), a ROS scavenger, significantly attenuated the apoptosis-inducing effect of coptisine. It is worth noting that coptisine significantly upregulated phosphorylation of ROS-dependent c-Jun N-terminal kinase (JNK), whereas treatment with JNK inhibitor could suppress an apoptosis-related series event. Taken together, our results suggest that coptisine has an anticancer effect in Hep3B cells through ROS-mediated activation of the JNK signaling pathway.

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7

Liu, Songcan, Xinfeng Zhang, Furong Qiu, Ping Miao, Shujiao Shen, Leilei Zhu, Jin Zeng, and Jian Jiang. "Metabolic Interaction of the Active Constituents ofCoptis chinensisin Human Liver Microsomes." Evidence-Based Complementary and Alternative Medicine 2015 (2015): 1–5. http://dx.doi.org/10.1155/2015/802903.

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Coptis chinensisis commonly used in traditional Chinese medicine. The study investigated metabolic interaction of the active constituents (berberine, coptisine, palmatine, and jatrorrhizine) ofCoptis chinensisin human liver microsomes. After incubation of the four constituents ofCoptis chinensisin HLMs, the metabolism of the four constituents was observed by HPLC. Thein vitroinhibition experiment between the active constituents was conducted, and IC50value was estimated. Coptisine exhibited inhibitions against the formation of the two metabolites of berberine with IC50values of 6.5 and 8.3 μM, respectively. Palmatine and jatrorrhizine showed the weaker inhibitory effect on the formation of the metabolites of berberine. Berberine showed a weak inhibitory effect on the production of coptisine metabolite with an IC50value of 115 μM, and palmatine and jatrorrhizine had little inhibitory effect on the formation of coptisine metabolite. Berberine, coptisine, and jatrorrhizine showed no inhibitory effect on the generation of palmatine metabolite (IC50> 200 μM). The findings suggested that there are different degrees of metabolic interaction between the four components. Coptisine showed the strongest inhibition toward berberine metabolism.

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8

Zhao, Yaping, and Xia Gao. "Coptisine Reduces the Progression of Cervical Cancer Through Induction of Autophagy." Current Topics in Nutraceutical Research 21, no. 1 (August 10, 2022): 18–24. http://dx.doi.org/10.37290/ctnr2641-452x.21:18-24.

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The regulatory role of coptisine on autophagy in cervical cancer cells (in HcerEpic, HeLa, and SiHa) was examined by assessment of cell viability, colony formation, and apoptosis. Coptisine, in a dose-dependent fashion, significantly inhibited cervical cancer cell viability as measured by cell proliferation, transwell, and TUNEL assays. Coptisine inhibited the levels of p62 and Bcl-2, whilst it promoted the accumulation of Atg5, LC3Ⅱ/LC3Ⅰ and Bax. These data taken together suggest that coptisine inhibits the progression of cervical cancer cells by enhancing autophagy through suppression of the PI3K/AKT/mTOR pathway. This represents a theoretical foundation for developing novel cervical cancer treatments.

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9

Colombo, Maria Laura, Carlo Bugatti, Andrea Mossa, Nicoletta Pescalli, Laura Piazzoni, Gabriella Pezzoni, Ernesto Menta, et al. "Cytotoxicity evaluation of natural coptisine and synthesis of coptisine from berberine." Il Farmaco 56, no. 5-7 (July 2001): 403–9. http://dx.doi.org/10.1016/s0014-827x(01)01121-1.

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10

Friedemann, Thomas, Udo Schumacher, Yi Tao, Alexander Kai-Man Leung, and Sven Schröder. "Neuroprotective Activity of Coptisine fromCoptis chinensis(Franch)." Evidence-Based Complementary and Alternative Medicine 2015 (2015): 1–9. http://dx.doi.org/10.1155/2015/827308.

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Coptis chinensisrhizomes (CR) are one important ingredient of traditional Chinese herbal formulas such as San-Huang-Xie-Xin-Tang which is used for treatment of cardiovascular and neurodegenerative diseases. Recent studies suggest that the extract of CR might be a potential therapeutic agent for amelioration of neurological disorders associated with oxidative stress. In the present study we aimed at revealing the main active compound(s) of the CR extract and at investigating the mechanism of action. Four main alkaloids of the CR extract (berberine, coptisine, jatrorrhizine, and palmatine) were selected for this study. Results showed that out of those alkaloids only pretreatment with coptisine significantly attenuated tert-butylhydroperoxide induced reduction of cell viability, increased rate of apoptosis, and declined mitochondrial membrane potential. Elisa assay and quantitative real-time PCR analyses revealed that thioredoxin-interacting protein (TXNIP) gene expression was downregulated by coptisine, which could explain the neuroprotective effect, hypothetically, by strengthening the thioredoxin defense system against oxidative stress and attenuation of apoptosis signal-regulating kinase (Ask1) mediated apoptotic signaling. A comparison between coptisine and CR extract identified coptisine as the main single component responsible for the neuroprotective effect. Based on the results the CR extract and coptisine are promising candidate agents for prevention or improvement of diabetic neuropathy and neurodegenerative disorders.

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11

Xie, Lan, Shanshan Feng, Xiaoling Zhang, Wenlong Zhao, Juan Feng, Chengmei Ma, Ruijun Wang, Weifang Song, and Jing Cheng. "Biological Response Profiling Reveals the Functional Differences of Main Alkaloids in Rhizoma Coptidis." Molecules 26, no. 23 (December 6, 2021): 7389. http://dx.doi.org/10.3390/molecules26237389.

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Rhizoma Coptidis (RC) is a widely used traditional Chinese medicine. Although modern research has found that some alkaloids from RC are the pharmacologically active constituents, the differences in their biological effects are not completely clear. This study analyzed the differences in the typical alkaloids in RC at a systematic level and provided comprehensive information on the pharmaceutical mechanisms of the different alkaloids. The ethanol RC extract (RCE) was characterized using HPLC assay. HepG2, 3T3-L1, and RAW264.7 cells were used to detect the cytotoxicity of alkaloids. Transcriptome analyses were performed to elucidate the cellular pathways affected by RCE and alkaloids. HPLC analysis revealed that the typical alkaloids of RCE were berberine, coptisine, and palmatine. Coptisine and berberine displayed a stronger inhibitory effect on cell proliferation than palmatine. The overlapping ratios of differentially expressed genes between RCE and berberine, coptisine, and palmatine were 70.8%, 52.6%, and 42.1%, respectively. Pathway clustering analysis indicated that berberine and coptisine possessed a certain similarity to RCE, and both compounds affected the cell cycle pathway; moreover, some pathways were uniquely enriched by berberine or coptisine. Berberine and coptisine had different regulatory effects on genes involved in lipid metabolism. These results provide comprehensive information on the pharmaceutical mechanisms of the different RC alkaloids and insights into their better combinatory use for the treatment of diseases.

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12

He, Yanfei, Siyu Chen, Hai Yu, Long Zhu, Yayun Liu, Chunyang Han, and Cuiyan Liu. "Effect of Catnip Charcoal on theIn VivoPharmacokinetics of the Main Alkaloids of Rhizoma Coptidis." Evidence-Based Complementary and Alternative Medicine 2016 (2016): 1–9. http://dx.doi.org/10.1155/2016/3532159.

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This study aims to explore the effect of catnipNepeta cataria(CNC) charcoal on the pharmacokinetics of the main alkaloids of Rhizoma Coptidisin vivo. Twenty-four rabbits were randomly divided into four groups and given oral administration of an aqueous extract of Rhizoma Coptidis (RCAE), RCAE plus CNC, RCAE plus activated carbon (AC), or distilled water, respectively. Plasma samples were collected after administration. The concentrations of berberine, coptisine, palmatine, and epiberberine in plasma were measured by high-performance liquid chromatography (HPLC). The pharmacokinetics data were calculated using pharmacokinetic DAS 2.0 software. The results showed that the area under the concentration-time curve (AUC) of berberine increased, while the AUC of coptisine, palmatine, and epiberberine decreased in the rabbits that received RCAE plus CNC. Meanwhile, the AUC of berberine, coptisine, palmatine, and epiberberine decreased in the group given RCAE plus AC. The difference of main pharmacokinetics parameters among the four groups was significant (P<0.05). This study showed that CNC improved the bioavailability of berberine in comparison to AC and prolonged its release in comparison to RCAE alone. However, it decreased the bioavailability of coptisine, palmatine, and epiberberine. In comparison, AC uniformly declined the bioavailability of berberine, coptisine, palmatine, and epiberberine.

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13

Colombo, Maria Laura, and et al et al. "ChemInform Abstract: Cytotoxicity Evaluation of Natural Coptisine and Synthesis of Coptisine from Berberine." ChemInform 32, no. 43 (May 24, 2010): no. http://dx.doi.org/10.1002/chin.200143224.

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14

Dostál, Jiřı́, Stanislav Man, Pavlı́na Sečkářová, Dagmar Hulová, Marek Nečas, Milan Potáček, Jaromı́r Toušek, Roger Dommisse, Walter Van Dongen, and Radek Marek. "Berberine and coptisine free bases." Journal of Molecular Structure 687, no. 1-3 (January 2004): 135–42. http://dx.doi.org/10.1016/j.molstruc.2003.09.018.

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15

Gu, Minwei, та Xinlian Wang. "Pseudogene MSTO2P Interacts with miR-128-3p to Regulate Coptisine Sensitivity of Non-Small-Cell Lung Cancer (NSCLC) through TGF-β Signaling and VEGFC". Journal of Oncology 2022 (26 червня 2022): 1–9. http://dx.doi.org/10.1155/2022/9864411.

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Background. Coptisine has been widely used for treating a variety of cancer types. To date, whether pseudogene is implicated in coptisine resistance of NSCLC remains unknown. Methods. We performed MTT to assess the cell viability of A549 and Calu-1 cells. The transwell assay was used to examine the invasion of cells. TUNEL was used to determine apoptosis. Results. Our data showed that coptisine treatment suppressed cell viability and invasion of NSCLC cells while contributing to apoptosis. MiR-128-3p negatively regulated MSTO2P. miR-128-3p reverted MSTO2P knockdown-attenuated cell viability and invasion, as well as promoted cell apoptosis of A549 cells. Moreover, we identified TGF-β signaling and VEGFC as key downstream effectors for MSTO2P and miR-128-3p in A549 cells. MiR-128-3p mimic inhibited TGF-β pathway-associated genes (TGFBR1, Smad2, Smad5, and Smad9), whereas miR-128-3p inhibitor exerted opposite effect. MSTO2P knockdown led to attenuated expression levels of TGFBR1, Smad2, Smad5 and Smad9. VEGFC overexpression greatly rescued miR-128-3p-modulated cell viability, invasion, and apoptosis of A549 cells. Conclusion. MSTO2P plays a role in coptisine therapy of NSCLC through miR-128-3p. The findings will advance our understanding of NSCLC treatment.

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16

Qiao, Yan-Ling, Yu-Xin Sheng, Li-Qun Wang, and Jin-Lan Zhang. "Development of a Rapid Resolution Liquid Chromatographic Method for Simultaneous Analysis of Four Alkaloids in Rhizoma coptidis Under Different Cultivation Conditions." Journal of AOAC INTERNATIONAL 92, no. 2 (March 1, 2009): 663–71. http://dx.doi.org/10.1093/jaoac/92.2.663.

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Abstract A sensitive and specific method using rapid resolution liquid chromatography coupled with UV-Vis detection was developed for fingerprint analysis of Rhizoma coptidis and simultaneous determination of 4 alkaloids: jatrorrhizine, coptisine, palmatine, and berberine. Samples of R. coptidis grown under different cultivation conditions and from different habitats were analyzed. The analysis was performed using a reversed-phase octylsilyl (C8) column and gradient elution. The mobile phase consisted of acetonitrile and 20 mmol/L KH2PO4. Each analysis was completed within 3.5 min. The method showed good linearity within test ranges of 4.7547.50 g/mL for jatrorrhizine, 20.60164.80 g/mL for coptisine, 18.07180.73 g/mL for palmatine, and 89.70717.57 g/mL for berberine. The method showed good precision, repeatability, and stability for quantification of the 4 alkaloids. The lower limit of detection was 0.19 ng for jatrorrhizine, 0.21 ng for coptisine, 0.15 ng for palmatine, and 0.14 ng for berberine. The lower limit of quantification was 0.57 ng for jatrorrhizine, 0.82 ng for coptisine, 0.55 ng for palmatine, and 0.27 ng for berberine. The overall recovery ranged from 96.30 to 104.10 for the 4 alkaloids. The method is accurate, rapid, and convenient, and it is suitable for routine quality control of R. coptidis.

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17

Nakonieczna, Sylwia, Aneta Grabarska, Kinga Gawel, Paula Wróblewska-Łuczka, Arkadiusz Czerwonka, Andrzej Stepulak, and Wirginia Kukula-Koch. "Isoquinoline Alkaloids from Coptis chinensis Franch: Focus on Coptisine as a Potential Therapeutic Candidate against Gastric Cancer Cells." International Journal of Molecular Sciences 23, no. 18 (September 7, 2022): 10330. http://dx.doi.org/10.3390/ijms231810330.

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Gastric cancer (GC) has high incidence rates and constitutes a common cause of cancer mortality. Despite advances in treatment, GC remains a challenge in cancer therapy which is why novel treatment strategies are needed. The interest in natural compounds has increased significantly in recent years because of their numerous biological activities, including anti-cancer action. The isolation of the bioactive compounds from Coptis chinensis Franch was carried out with the Centrifugal Partition Chromatography (CPC) technique, using a biphasic solvent system composed of chloroform (CHCl3)—methanol (MeOH)—water (H2O) (4:3:3, v/v) with an addition of hydrochloric acid and trietylamine. The identity of the isolated alkaloids was confirmed using a high resolution HPLC-MS chromatograph. The phytochemical constituents of Coptis chinensis such as berberine, jatrorrhizine, palmatine and coptisine significantly inhibited the viability and growth of gastric cancer cell lines ACC-201 and NCI-N87 in a dose-dependent manner, with coptisine showing the highest efficacy as revealed using MTT and BrdU assays, respectively. Flow cytometry analysis confirmed the coptisine-induced population of gastric cancer cells in sub-G1 phase and apoptosis. The combination of coptisine with cisplatin at the fixed-ratio of 1:1 exerted synergistic and additive interactions in ACC-201 and NCI-N87, respectively, as determined by means of isobolographic analysis. In in vivo assay, coptisine was safe for developing zebrafish at the dose equivalent to the highest dose active in vitro, but higher doses (greater than 10 times) caused morphological abnormalities in larvae. Our findings provide a theoretical foundation to further studies on more detailed mechanisms of the bioactive compounds from Coptis chinensis Franch anti-cancer action that inhibit GC cell survival in in vitro settings.

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18

Slavík, Jiří, and Leonora Slavíková. "Quaternary Alkaloids from Thalictrum minus subsp. elatum (JACQ.) STOY. et STEFANOV." Collection of Czechoslovak Chemical Communications 57, no. 3 (1992): 573–78. http://dx.doi.org/10.1135/cccc19920573.

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Quaternary alkaloids berberine (chloride, 0.18%) and, after transformation into the iodides, magnoflorine (iodide, 1.06%), jatrorrhizine (iodide, 0.066%), thalphenine (iodide, 0.040%) and thalifendine (iodide, 0.021%) were isolated, after separation of the tertiary bases (0.38%) from the root of Thalictrum minus subsp. elatum (JACQ.) STOJ. et STEFANOV of Czechoslovak origin (1.8% alkaloid content). The aerial parts (0.013% alkaloids) in their quaternary fraction contain only negligible amounts of magnoflorine, berberine, and coptisine (which is the first time coptisine was found in the Thalictrum genus).

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Kong, Xiang-Peng, Etta Y. L. Liu, Zhi-Cong Chen, Miranda Li Xu, Anna X. D. Yu, Qi-Yun Wu, Ying-Jie Xia, Ran Duan, Tina T. X. Dong, and Karl W. K. Tsim. "Synergistic Inhibition of Acetylcholinesterase by Alkaloids Derived from Stephaniae Tetrandrae Radix, Coptidis Rhizoma and Phellodendri Chinensis Cortex." Molecules 24, no. 24 (December 13, 2019): 4567. http://dx.doi.org/10.3390/molecules24244567.

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Alkaloids having acetylcholinesterase (AChE) inhibitory activity are commonly found in traditional Chinese medicine (TCM); for example, berberine from Coptis chinensis, galantamine from Lycoris radiata, and huperzine A from Huperzia serrata. In practice of TCM, Stephaniae Tetrandrae Radix (STR) is often combined with Coptidis Rhizoma (CR) or Phellodendri Chinensis Cortex (PCC) as paired herbs during clinical application. Fangchinoline from STR and coptisine and/or berberine from CR and/or PCC are active alkaloids in inhibiting AChE. The traditional usage of paired herbs suggests the synergistic effect of fangchinoline–coptisine or fangchinoline–berberine pairing in AChE inhibition. HPLC was applied to identify the main components in herbal extracts of STR, CR, and PCC, and the AChE inhibition of their main components was determined by Ellman assay. The synergism of herb combination and active component combination was calculated by median-effect principle. Molecular docking was applied to investigate the underlying binding mechanisms of the active components with the AChE protein. It was found that fangchinoline showed AChE inhibitory potency; furthermore, fangchinoline–coptisine/berberine pairs (at ratios of 1:5, 1:2, 1:1, and 2:1) synergistically inhibited AChE; the combination index (CI) at different ratios was less than one when Fa = 0.5, suggesting synergistic inhibition of AChE. Furthermore, the molecular docking simulation supported this enzymatic inhibition. Therefore, fangchinoline–coptisine/berberine pairs, or their parental herbal mixtures, may potentially be developed as a possible therapeutic strategy for Alzheimer’s patients.

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Slavík, Jiří, and Leonora Slavíková. "Alkaloids from Corydalis nobilis (L.) PERS. and C. intermedia (L.) MÉRAT." Collection of Czechoslovak Chemical Communications 54, no. 7 (1989): 2009–20. http://dx.doi.org/10.1135/cccc19892009.

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Rhizomes of Corydalis nobilis (L.) PERS. (3% of alkaloids) contain (+)-tetrahydropalmatine, (+)-bicuculline and (+)-corytuberine as the main constituents of the tertiary alkaloid fraction. Protopine, (+)-corypalmine and (+)-stylopine, which also belong to the dominant alkaloids, were isolated in lesser amounts. As minor alkaloids were isolated (±)-tetrahydropalmatine, (+)-corydaline, allocryptopine, cryptopine, (-)-scoulerine, (+)-adlumidine, (+)-sinactine, (±)-corlumine, isoboldine, (+)-corybulbine, (±)-stylopine and (-)-isocorypalmine. The fraction of quaternary protoberberine alkaloids afforded coptisine dehydrocorydaline, palmatine, corysamine jatrorrhizine and cis-N-methylstylopinium hydroxide. Aobamidine (Z-adlumidiceine enol lactone), isolated as the principal alkaloid of aerial parts (0.3% of alkaloids), is obviously an artifact arising from bicuculline N-metho salt during the isolation process. Further dominant alkaloids of the tertiary fraction were adlumidine, bicuculline, protopine, (±)-tetrahydropalmatine and (±)-corlumine; as minor alkaloids were isolated corytuberine, scoulerine, corypalmine, cryptopine, isocorypalmine, corybulbine, (+)-corydalizine, and unidentified alkaloids CN 1 (C23H25NO5, m.p. 211 °C) and CN 2 (m.p. 261 °C). Quaternary protoberberine fraction afforded coptisine and palmatine. Nineteen of the mentioned alkaloids were isolated from this species for the first time. Tubers of C. intermedia (L.) MÉRAT (0.70% of alkaloids) afforded protopine, tetrahydropalmatine and corydaline as the main alkaloids and allocryptopine, canadine stylopine, palmatine, dehydrocorydaline, berberine, coptisine as minor alkaloids, together with traces of bicuculline and magnoflorine. Dominant alkaloids of the aerial part (0.73% of alkaloids) were bicuculline, bulbocapnine, protopine, stylopine and an unidentified phenolic base, m.p. 258 °C. Isoboldine, scoulerine, allocryptopine, corydaline, canadine, coptisine, palmatine and berberine were identified as the minor alkaloids.

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21

Kaminskyy, Vitaliy, Maxim Lootsik, and Rostyslav Stoika. "Correlation of the cytotoxic activity of four different alkaloids, from Chelidonium majus (greater celandine), with their DNA intercalating properties and ability to induce breaks in the DNA of NK/Ly murine lymphoma cells." Open Life Sciences 1, no. 1 (March 1, 2006): 2–15. http://dx.doi.org/10.2478/s11535-006-0001-y.

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AbstractThe purpose of this study was to examine the relationship between the DNA intercalating characteristics and the DNA damaging capacity of four alkaloids extracted from Chelidonium majus L, as well as their toxicity towards murine NK/Ly lymphoma cells. Chelerythrine, sanguinarine and coptisine were found to be intercalated into the DNA isolated from NK/Ly cells, meanwhile, chelidonine exhibited no affinity to DNA. Sanguinarine exhibited the greatest toxicity toward NK/Ly cells, and the toxicity of the other three decreased in descending order: chelerythrine, coptisine and chelidonine. Chelerythrine and sanguinarine caused DNA damage, illustrated by the formation of comets of the third class. Coptisine was less toxic than chelerythrine and sanguinarine, and affected the formation the same class of comets in higher concentration. The quantity of comets induced by chelidonine were negligible, a finding consistent with its inability to intercalate into DNA structure. The ability of four main alkaloids of Chelidonium majus L., to intercalate into DNA isolated from murine NK/Ly lymphoma cells, correlated with their ability to induce breaks in cellular DNA and with their toxic effect towards those cells.

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22

Slavík, Jiří, and Leonora Slavíková. "Alkaloids from Papaver bracteatum LINDL." Collection of Czechoslovak Chemical Communications 50, no. 5 (1985): 1216–26. http://dx.doi.org/10.1135/cccc19851216.

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Анотація:

N-Methylthebainium (as iodide) and corytuberine were isolated from the roots and green aerial parts of Papaver bracteatum LINDL., thebaine race Halle III, as significant alkaloids in addition to the predominant alkaloid thebaine (0.61 and 0.23% respectively), as well as the minor alkaloids isothebaine, scoulerine, protopine, epialpinine (O-methylalpinigenine), N-methylisothebainium (as iodide), isoboldine, corydine, rhoeadine, magnoflorine, a mixture of coptisine and palmatine and a new alkaloid PB 1 C18H19NO4. Bracteoline and papaverrubines G, E, D and C were detected chromatographically. From the ripe capsules of the race Halle III N-methylthebainium (as perchlorate), corytuberine and a mixture of coptisine and palmatine were isolated in addition to thebaine (0.67%). From the ripe capsules of P. bracteatum, population Demavend (Iran), thebaine (0.56%), epialpinine, alpinigenine, corytuberine, N-methylthebainium (as iodide) and a mixture of coptisine and palmatine were isolated and the presence of papaverrubines G, D and C was detected. In the latex of flowering plants salutaridine was also detected. Fourteen of the mentioned alkaloids were detected in the species P. bracteatum for the first time.

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23

Luo, Jiaoyang, Dan Yan, Meihua Yang, Xiaoping Dong, and Xiaohe Xiao. "Multicomponent Therapeutics of Berberine Alkaloids." Evidence-Based Complementary and Alternative Medicine 2013 (2013): 1–10. http://dx.doi.org/10.1155/2013/545898.

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Анотація:

Although berberine alkaloids (BAs) are reported to be with broad-spectrum antibacterial and antiviral activities, the interactions among BAs have not been elucidated. In the present study, methicillin-resistantStaphylococcus aureus(MRSA) was chosen as a model organism, and modified broth microdilution was applied for the determination of the fluorescence absorption values to calculate the anti-MRSA activity of BAs. We have initiated four steps to seek the optimal combination of BAs that are (1) determining the anti-MRSA activity of single BA, (2) investigating the two-component combination to clarify the interactions among BAs by checkerboard assay, (3) investigating the multicomponent combination to determine the optimal ratio by quadratic rotation-orthogonal combination design, and (4)in vivoandin vitrovalidation of the optimal combination. The results showed that the interactions among BAs are related to their concentrations. The synergetic combinations included “berberine and epiberberine,” “jatrorrhizine and palmatine” and “jatrorrhizine and coptisine”; the antagonistic combinations included “coptisine and epiberberine”. The optimal combination was berberine : coptisine : jatrorrhizine : palmatine : epiberberine = 0.702 : 0.863 : 1 : 0.491 : 0.526, and the potency of the optimal combination on cyclophosphamide-immunocompromised mouse model was better than the natural combinations of herbs containing BAs.

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24

Peredelcu Rodica, Gonciar Veaceslav, Scutari Corina, and Cazacu Vasile. "THE INFLUENCE OF COPTISINE BISULFATE ON THE EVOLUTION OF ACUTE TOXIC HEPATITIS." World Science 2, no. 8(36) (August 30, 2016): 42–46. http://dx.doi.org/10.31435/rsglobal_ws/30082018/6065.

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Анотація:

In the experiments made on white rats was studied the influence of coptisine bisulfate, alkaloid extracted from Chelidonium majus, in the following doses: 10 mg/kg and 20 mg/kg on acute toxic hepatitis cause by carbon tetrachloride. It was established that the researched substance reduced hepatic cytolysis and cholestasis through reestablishment of the transaminases activity and lactate dehydrogenase, while lowering the alkaline phosphatase/alanine aminotransferase ratio and modulated the deflection of the metabolic parameters of acute toxic hepatitis. Coptisine bisulfate corrected the carbon tetrachloride caused hypoproteinemia when administered for 7 days and normalized the albumin level at 14th day of treatment of acute toxic hepatitis.

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25

Táborská, Eva, Milena Mikešová, František Věžník, and Jiří Slavík. "Alkaloids of the two Hypecoum L. species." Collection of Czechoslovak Chemical Communications 52, no. 2 (1987): 508–13. http://dx.doi.org/10.1135/cccc19870508.

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Анотація:

Alkaloids from Hypecoum procumbens L. and H. leptocarpum HOOK. F. et THOMS. were investigated. Protopine was the dominant alkaloid in both species. From H. procumbens chelerythrine and corydine were newly isolated in addition to the earlier detected alkaloids allocryptopine, sanguinarine, coptisine, and isocorydine. From H. leptocarpum allocryptopine, isocorydine and corydine were isolated for the first time, in addition to the earlier described alkaloids protopine, sanguinarine, chelerythrine and coptisine. Cryptopine was detected chromatographically. From the fraction of strongly polar alkaloids of both species magnoflorine, (-)-trans-N-methyl-stylopinium hydroxide, and in small amounts a new secoberbine alkaloid of oxohypecorinine structure, procumbine (I), and two further alkaloids of unsolved structure were isolated in the form of iodides.

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26

Slavík, Jiří, and Leonora Slavíková. "Alkaloids of Meconopsis cambrica (L.) VIG. and M. robusta HOOK. f. et THOMS." Collection of Czechoslovak Chemical Communications 61, no. 12 (1996): 1815–22. http://dx.doi.org/10.1135/cccc19961815.

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Анотація:

Additional alkaloids (+)-roemerine (3b), (+)-corytuberine (3d), (-)-N-methylmecambridinium and alkaloid MC 2 (the last two as iodides) were isolated as minor alkaloidal components from Meconopsis cambrica (L.) VIG. (Papaveraceae) besides of the dominant known alkaloids (-)-mecambrine (1), (-)-mecambridine (2), (-)-flavinantine (4) and (+)-magnoflorine (5), and a small amount of (+)-mecambroline (3a). Minute quantities of protopine, allocryptopine, roemeroline, papaverrubine D and C, berberine, coptisine, corysamine and palmatine were identified by thin layer chromatography (TLC). From M. robusta HOOK. f. et THOMS., protopine, (-)-amurensinine (6) and two incompletely characterized alkaloids MRO 1 and MRO 2 were isolated, and allocryptopine, cryptopine, rhoeadine, 6-methoxy-2-methyl-1,2,3,4-tetrahydro-β-carboline, alkaloid MR 1, coptisine, corysamine, magnoflorine, corytuberine and N-methylamurensininium salt were detected on TLC.

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27

Cao, Qianyu, Shengwei Hong, Yuanyuan Li, Heng Chen, Yining Shen, Kang Shao, Mengjie Lu, Hui Dai, Shitang Ma, and Guoliang Dai. "Coptisine suppresses tumor growth and progression by down-regulating MFG-E8 in colorectal cancer." RSC Advances 8, no. 54 (2018): 30937–45. http://dx.doi.org/10.1039/c8ra05806g.

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Анотація:

Treating colorectal cancer (CRC) continues to be a clinical challenge. Coptisine, an alkaloid derived from Coptis chinensis Franch. shows toxic effects on CRC cells, but its underlying mechanism remains elusive.

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28

Mi, Ran, Xiao-Ting Bai, Bao Tu, and Yan-Jun Hu. "Unraveling the coptisine–ctDNA binding mechanism by multispectroscopic, electrochemical and molecular docking methods." RSC Advances 5, no. 59 (2015): 47367–76. http://dx.doi.org/10.1039/c5ra08790b.

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This study provides evidences of coptisine–DNA intercalation, which may help to develop new efficient, safe probes for the fluorometric detection of DNA instead of traditional toxic and carcinogenic probes.

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29

Jiao, Yanqi, Chengcheng Shi, and Yao Sun. "Unraveling the Role of Scutellaria baicalensis for the Treatment of Breast Cancer Using Network Pharmacology, Molecular Docking, and Molecular Dynamics Simulation." International Journal of Molecular Sciences 24, no. 4 (February 10, 2023): 3594. http://dx.doi.org/10.3390/ijms24043594.

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Scutellaria baicalensis is often used to treat breast cancer, but the molecular mechanism behind the action is unclear. In this study, network pharmacology, molecular docking, and molecular dynamics simulation are combined to reveal the most active compound in Scutellaria baicalensis and to explore the interaction between the compound molecule and the target protein in the treatment of breast cancer. In total, 25 active compounds and 91 targets were screened out, mainly enriched in lipids in atherosclerosis, the AGE–RAGE signal pathway of diabetes complications, human cytomegalovirus infection, Kaposi-sarcoma-associated herpesvirus infection, the IL-17 signaling pathway, small-cell lung cancer, measles, proteoglycans in cancer, human immunodeficiency virus 1 infection, and hepatitis B. Molecular docking shows that the two most active compounds, i.e., stigmasterol and coptisine, could bind well to the target AKT1. According to the MD simulations, the coptisine–AKT1 complex shows higher conformational stability and lower interaction energy than the stigmasterol–AKT1 complex. On the one hand, our study demonstrates that Scutellaria baicalensis has the characteristics of multicomponent and multitarget synergistic effects in the treatment of breast cancer. On the other hand, we suggest that the best effective compound is coptisine targeting AKT1, which can provide a theoretical basis for the further study of the drug-like active compounds and offer molecular mechanisms behind their roles in the treatment of breast cancer.

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30

Slavík, Jiří, and Leonora Slavíková. "Alkaloids from Papaver albiflorum PACZ. subsp. albiflorum and P. cf. stevenianum A. D. Mikheev." Collection of Czechoslovak Chemical Communications 55, no. 7 (1990): 1812–16. http://dx.doi.org/10.1135/cccc19901812.

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Анотація:

Papaver albiflorum PACZ. subsp. albiflorum (tetraploid, 2n = 28; total alkaloid content 0.001%) afforded corytuberine, protopine and allocryptopine as dominant alkaloids; in addition, small amounts of macambrine, thebaine, scoulerine, rhoeadine, papaverrubines D, C, A and E, berberine and coptisine were detected. Papaver cf. stevenianum A. D. MIKHEEV (hexaploid, 2n = 42; total alkaloid content 0.066% and 0.015%, respectively) gave berberine as the principal alkaloid (0.065% and 0.013, respectively) which was responsible for the yellow colour of latex. Corytuberine, allocryptopine, protopine and isocorydine were isolated as minor alkaloids and small amounts of corydine, mecambrine, thebaine, scoulerine, papaverrubines D, C, A and E, coptisine, cis-N-methylcanadinium hydroxide and N-methylthebainium hydroxide were detected. Alkaloid PHC 1, isolated recently as minor constituent from Papaver rhoeas var. chelidonioides O. KUNTZE, has been shown to be identical with isorhoeagenine.

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31

Slavík, Jiří, Vladimír Hanuš, and Leonora Slavíková. "Alkaloids from Stylophorum lasiocarpum (OLIV.) FEDDE." Collection of Czechoslovak Chemical Communications 56, no. 5 (1991): 1116–22. http://dx.doi.org/10.1135/cccc19911116.

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Анотація:

From the underground part of Stylophorum lasiocarpum (OLIV.) FEDDE (0.58% alkaloids) (-)-stylopine and coptisine (as chloride IIa) were isolated as the principal alkaloids. Smaller quantities of sanguinarine, macarpine, chelerythrine, chelirubine, chelilutine (as the respective chlorides IIIa, IIIb, IIIc, IIId, IIIe) protopine, corysamine (as chloride IIb), berberine (as chloride IIc) and (-)-trans-N-methylstylopinium hydroxide (as iodide IVa) were also isolated. Chromatographically were detected small amounts of chelidonine, allocryptopine, cryptopine, scoulerine, isoboldine, magnoflorine and salt of cis-N-methylstylopinium. The aerial part (0.16% alkaloids) afforded (-)-stylopine, coptisine and (+)-chelidonine as dominant alkaloids and small amounts of protopine and (-)-cis-N-methylstylopinium hydroxide (as iodide IVb).Chromatography proved negligible amounts of sanguinarine, chelirubine, cryptopine, scoulerine, isoboldine, corytuberine, corysamine, berberine, magnoflorine and trans-N-methylstylopinium iodide. The so far undescribed 8-methoxydihydromacarpine (VIb) was prepared.

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32

HIRANO, Hiroyuki, Eriko OSAWA, Yumiko YAMAOKA, and Toshio YOKOI. "Gastric-Mucous Membrane Protection Activity of Coptisine Derivatives." Biological & Pharmaceutical Bulletin 24, no. 11 (2001): 1277–81. http://dx.doi.org/10.1248/bpb.24.1277.

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33

Li, Changfeng, Jianxia Feng, and Huangxian Ju. "Supramolecular interaction of labetalol with cucurbit[7]uril for its sensitive fluorescence detection." Analyst 140, no. 1 (2015): 230–35. http://dx.doi.org/10.1039/c4an01601g.

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Анотація:

The supramolecular interaction between labetalol and cucurbit[7]uril is studied for simple and sensitive fluorescence detection of labetalol through its competitive interaction with berberine, palmatine or coptisine for occupancy of the cucurbit[7]uril cavity.

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34

Táborská, Eva, Jiří Dostál, Hana Bochořáková, and František Věžník. "Alkaloids of Papaver argemone L. and Papaver pavoninum FISCH. et MEY. From the Argemonorhoeades FEDDE section." Collection of Czechoslovak Chemical Communications 53, no. 8 (1988): 1845–50. http://dx.doi.org/10.1135/cccc19881845.

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Анотація:

Papaver argemone L. and Papaver pavoninum FISCH. et MEY. species of the Argemonorhoeades FEDDE (Papaveraceae) section were studied. A very low content of alkaloids was found in both species (less than 0·05%). P. argemone contains corytuberine and its quaternary N-methyl derivative magnoflorine as the dominant bases. As minor constituents were isolated: protopine, isocorydine, scoulerine, and alkaloids PAR 1, PAR 2, PAR 3. Chromatographic analysis detected allocryptopine, cryptopine, coptisine and traces of rhoeadine, papaverrubines C, D and E, and more than 6 unidentified bases. P. pavoninum gave N2-methyl-1,2,3,4-tetrahydro-β-carboline as the dominant alkaloid, along with minor amounts of the tertiary bases protopine, allocryptopine, corydine, isocorydine and corytuberine. Of quaternary bases, coptisine, magnoflorine and an unidentified alkaloid PP 1 were isolated. The presence of many other, considerably labile bases has been proven in both species.

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35

Wu, Cuiting, Xin Wang, Ming Xu, Youping Liu, and Xin Di. "Intracellular Accumulation as an Indicator of Cytotoxicity to Screen Hepatotoxic Components of Chelidonium majus L. by LC–MS/MS." Molecules 24, no. 13 (June 29, 2019): 2410. http://dx.doi.org/10.3390/molecules24132410.

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Анотація:

A novel strategy was developed to identify hepatotoxic compounds in traditional Chinese medicines (TCMs). It is based on the exposure of HL-7702 cells to a TCM extract, followed by the identification and further determination of potential hepatotoxic compounds accumulated in the cells by liquid chromatography–tandem mass spectrometry (LC–MS/MS). As a case study, potential hepatotoxic components in Chelidonium majus L. were screened out. Five alkaloids (sanguinarine, coptisine, chelerythrine, protopine, and chelidonine) were identified by LC–MS/MS within 10 min, and their intracellular concentrations were first simultaneously measured by LC–MS/MS with a run time of 4 min. A cell viability assay was performed to assess the cytotoxicity of each alkaloid. With their higher intracellular concentrations, sanguinarine, coptisine, and chelerythrine were identified as the main hepatotoxic constituents in Ch. majus. The study provides a powerful tool for the fast prediction of cytotoxic components in complex natural mixtures on a high-throughput basis.

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36

Věžník, František, Irgash A. Israilov, Eva Táborská, and Jiří Slavík. "On alkaloids of three Papaver species from the section Scapiflora REICHB." Collection of Czechoslovak Chemical Communications 50, no. 8 (1985): 1745–52. http://dx.doi.org/10.1135/cccc19851745.

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Анотація:

The main alkaloid of the aerial part of P. croceum LEDEB. was nudaurine (I), isolated for the first time. In addition to amurine, known to be present in this species, oxysanguinarine (II) and corydine (IIIa) were also newly isolated and the presence of papaverrubine D demonstrated. In the fraction of tertiary bases from P.kerneri HAYEK allocryptopine and epialpinine (IV) were isolated as further alkaloids in addition to the already known alkaloids amurensine (the main alkaloid), amurensinine, amurine, alpinigenine, muramine, protopine, mecambridine, nudaurine, cryptopine and papaverrubines B, D, and G. In the fraction of quaternary bases the presence of traces of coptisine was detected, and in addition to alborine (alkaloid PO-5) cis-N-methyltetrahydropalmatinium hydroxide (V) was isolated for the first time in the form of iodide from P. kerneri. In P. tatricum (NYÁR.) EHREND. allocryptopine, epialpinine, and amurensinine were identified as the dominant alkaloids, while among the minor components protopine, amurensine, muramine, palmatine, coptisine, corytuberine (IIIb), N-methyltetrahydropalmatinium hydroxide, and N-methylamurensinium hydroxide could be demonstrated. Corydine (IIIa) and corytuberine (IIIb) represent the first two aporphine alkaloids found in the Scapiflora section.

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37

Slavík, Jiří, Ladislav Dolejš, and Leonora Slavíková. "Alkaloids from Corydalis solida (L.) SW. mass spectrometry of quaternary benzylisoquinoline alkaloids." Collection of Czechoslovak Chemical Communications 50, no. 10 (1985): 2299–309. http://dx.doi.org/10.1135/cccc19852299.

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Анотація:

From the strongly polar fraction from the tubers of Corydalis solida (L.) SW., a new quaternary alkaloid, (+)-N-methyllaudanidinium iodide, was isolated after conversion to iodides. Mass spectrometric behaviour of this type of quaternary alkaloids is described. In the tubers (0.37% of alkaloids) the main alkaloid component is (+)- and (±)-tetrahydropalmatine; other dominant alkaloids include protopine, (+)-corydaline, allocryptopine, dehydrocorydaline and jatrorrhizine. (±)-Corybulbine, (+)-corypalmine, (-)-isocorypalmine, (-)-scoulerine, (-)-stylopine, corysamine, palmatine, (+)-N-methyllaudanidinium hydroxide, (-)-cis-N-methylcanadinium hydroxide and cis-N-methylstylopinium hydroxide represent minor alkaloids. The last three mentioned were isolated in the form of iodides. Bulbocapnine, coptisine, berberine and columbamine were detected in trace amounts. The main alkaloid of the aerial parts of the plant (0.35% of alkaloids) is berberine, accompanied by coptisine, (-)- and (±)-canadine, (-)-stylopine, isoboldine, protopine, columbamine and (-)-cis-N-methylcanadinium hydroxide (isolated in the form of iodide) as significant components. Among minor alkaloids allocryptopine, (-)-isocorypalmine, (+)-corypalmine, (±)- and (-)-tetrahydropalmatine, corysamine, dehydrothalictricavine, palmatine and cis-N-methylstylopinium hydroxide (as iodide) were isolated and trace amounts of jatrorrhizine and bulbocapnine were detected.

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38

Seo, Chang-Seob, and Hyeun-Kyoo Shin. "Development and Validation of a High-Performance Liquid Chromatographic Method for the Simultaneous Quantification of Marker Constituents in Cheonwangbosimdan." Natural Product Communications 9, no. 12 (December 2014): 1934578X1400901. http://dx.doi.org/10.1177/1934578x1400901224.

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Анотація:

A high-performance liquid chromatography–photodiode array detector method was established for the simultaneous determination of 7 components in Cheonwangbosimdan extract. The components were 5-hydroxymethyl-2-furaldehyde (1), coptisine (2), berberine (3), nodakenin (4), harpagoside (5), cinnamic acid (6), and β-asarone (7). All analytes were separated by gradient elution using two mobile phases on a Gemini C18 column and maintained at 40°C. The flow rate was 1.0 mL/min and the injection volume was 10 μL. Calibration curves of the 7 compounds showed good linearity with correlation coefficients ( r2) ≥ 0.9996. The limits of detection and quantification of the 7 analytes were 0.01–0.04 and 0.03–0.12 μg/mL, respectively. The recoveries of the 7 marker constituents were 97.6–104.2% with relative standard deviations (RSD) of less than 2.2%. The RSD values of intra- and interday precision were 0.11–1.78 and 0.19–1.92%, respectively. Among the 7 biomarker compounds, the major compounds of Cheonwangbosimdan were berberine and coptisine, which originated from Coptis japonica. The results indicate that the developed analytical method is suitable for quality control use.

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39

Yang, Xiuying, Lili Shi, Li Zhang, Guifen Qiang, and Guanhua Du. "P15 Effects of coptisine on glucose metabolism and the mechanisms." Biochemical Pharmacology 139 (September 2017): 129. http://dx.doi.org/10.1016/j.bcp.2017.06.016.

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40

Slavík, Jiří, Leonora Slavíková, and Jitka Bochořáková. "Alkaloids from Papaver rhoeas var. chelidonioides O. KUNTZE, P. confine JORD., and P. dubium L." Collection of Czechoslovak Chemical Communications 54, no. 4 (1989): 1118–25. http://dx.doi.org/10.1135/cccc19891118.

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Анотація:

Papaver rhoeas var. chelidonioides O. KUNTZE (diploid, 2n = 14) contains rhoeadine (0.027%) and coptisine (0.004%) as the dominant alkaloids, the latter being the yellow principle of the latex. As minor constituents were isolated protopine, papaverrubine A, rhoeagenine, (-)-stylopine, an unidentified alkaloid PCH 1 (m.p. 205 °C), 2-methyl-1,2,3,4-tetrahydro-β-carboline and (-)-trans-N-methylstylopinium hydroxide. Chromatographic analysis detected isorhoeadine, allocryptopine, cryptopine, papaverrubine C, D and E, scoulerine, isoboldine, berberine, corysamine, magnoflorine and corytuberine. P. confine JORD. (tetraploid, 2n = 28) was found to display a very low alkaloid content (0.003%) and afforded corytuberine and berberine as principal alkaloids, along with minor amounts of protopine rhoeadine, scoulerine and cryptopine. Chromatography identified isocorydine, corydine, allocryptopine, aporheine, stylopine, sinactine, thebaine, mecambrine, papaverrubines A, E, C and D, coptisine and corysamine. The tertiary alkaloid fraction from ripe capsules of P. dubium L. (hexaploid, 2n = 42; 0.24% of alkaloids) of domestic origin afforded (+)-roemerine (aporheine) as the main constituent (87% of total bases); mecambrine, protopine, rhoeadine and papaverrubines D and C (traces of A and E) were detected. From strongly polar bases N-methylaporheinium hydroxide (as iodide) was isolated and corytuberine detected.

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41

Zhao, Yi, J. Jason Collier, E.-Chu Huang, and Jay Whelan. "Turmeric and Chinese goldthread synergistically inhibit prostate cancer cell proliferation and NF-kB signaling." Functional Foods in Health and Disease 4, no. 7 (July 22, 2014): 312. http://dx.doi.org/10.31989/ffhd.v4i7.1.

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Background: Pre-clinical studies using bioactive compounds from botanicals appear to offer some protection against cancer. Research using single bioactives contributes greatly to our understanding of their mechanism of action, but in vitro studies demand concentrations that are higher than achievable in humans (µM). However, maintaining these bioactives in the presence of other compounds originally derived from the food or extract of origin may synergistically lower the bioactive dose so translatability becomes feasible. The objective of this study was to determine if bio-efficacy of phytonutrients can be enhanced when used in combination even at doses that are ineffective for any compound when used in isolation. Methods: The anti-proliferative and molecular effects of herbs (turmeric and Chinese goldthread) and their bioactives (curcumin and ar-turmerone, berberine and coptisine, respectively) were determined in isolation and in combination. Using CWR22Rv1 and HEK293 cells, cell proliferation (as assessed by the MTT assay) and NF-κB promoter activity (using a luciferase reporter construct) were evaluated and synergy of action was assessed by the Chou-Talalay method utilizing CompuSyn® software. Results: Turmeric and Chinese goldthread act synergistically (combination index<1) when inhibiting cell proliferation with all cell lines tested. The synergy of action of combinations of companion bioactives from the same herb (i.e., curcumin/ar-turmerone and berberine/coptisine) and bioactives from different herbs (i.e., curcumin/berberine) help to explain why turmeric and Chinese goldthread are more effective than their major bioactives in isolation. At the molecule level, curcumin+ar-turmerone and curcumin+coptisine synergistically attenuated TNFα-stimulated NF-κB promoter activity. Even compounds with poor efficacy become more biologically active in the presence of companion compounds. Importantly, the effects of combining any two bioactives or herbal extracts were highly synergistic at concentrations approaching physiological significance (nanomolar). Conclusions: These results suggest that bioactives in combination (as plant extracts or isolated compounds) are highly synergistic at the cellular and molecular level at physiologically relevant concentrations. These data help to explain why complex mixtures of botanicals may be more efficacious than their bioactives in isolation.

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42

Zielińska, Sylwia, Monika Ewa Czerwińska, Magdalena Dziągwa-Becker, Andrzej Dryś, Mariusz Kucharski, Anna Jezierska-Domaradzka, Bartosz J. Płachno, and Adam Matkowski. "Modulatory Effect of Chelidonium majus Extract and Its Alkaloids on LPS-Stimulated Cytokine Secretion in Human Neutrophils." Molecules 25, no. 4 (February 14, 2020): 842. http://dx.doi.org/10.3390/molecules25040842.

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Due to certain differences in terms of molecular structure, isoquinoline alkaloids from Chelidonium majus engage in various biological activities. Apart from their well-documented antimicrobial potential, some phenanthridine and protoberberine derivatives as well as C. majus extract present with anti-inflammatory and cytotoxic effects. In this study, the LC–MS/MS method was used to determine alkaloids, phenolic acids, carboxylic acids, and hydroxybenzoic acids. We investigated five individually tested alkaloids (coptisine, berberine, chelidonine, chelerythrine, and sanguinarine) as well as C. majus root extract for their effect on the secretion of IL-1β, IL-8, and TNF-α in human polymorphonuclear leukocytes (neutrophils). Berberine, chelidonine, and chelerythrine significantly decreased the secretion of TNF-α in a concentration-dependent manner. Sanguinarine was found to be the most potent inhibitor of IL-1β secretion. However, the overproduction of IL-8 and TNF-α and a high cytotoxicity for these compounds were observed. Coptisine was highly cytotoxic and slightly decreased the secretion of the studied cytokines. The extract (1.25–12.5 μg/mL) increased cytokine secretion in a concentration-dependent manner, but an increase in cytotoxicity was also noted. The alkaloids were active at very low concentrations (0.625–2.5 μM), but their potential cytotoxic effects, except for chelidonine and chelerythrine, should not be ignored.

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43

Fan, Hui, Yuan-yuan Chen, Wei-jian Bei, Lai-you Wang, Bao-tian Chen, and Jiao Guo. "In VitroScreening for Antihepatic Steatosis Active Components within Coptidis Rhizoma Alkaloids Extract Using Liver Cell Extraction with HPLC Analysis and a Free Fatty Acid-Induced Hepatic Steatosis HepG2 Cell Assay." Evidence-Based Complementary and Alternative Medicine 2013 (2013): 1–9. http://dx.doi.org/10.1155/2013/459390.

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A high-throughput method was developed and applied to screen for the active antihepatic steatosis components within Coptidis Rhizoma Alkaloids Extract (CAE). This method was a combination of two previously described assays: HepG2 cell extraction with HPLC analysis and a free fatty acid-induced (FFA) hepatic steatosis HepG2 cell assay. Two alkaloids within CAE, berberine and coptisine, were identified by HepG2 cell extraction with HPLC analysis as high affinity components for HepG2. These alkaloids were also determined to be active and potent compounds capable of lowering triglyceride (TG) accumulation in the FFA-induced hepatic steatosis HepG2 cell assay. This remarkable inhibition of TG accumulation (P < 0.01) by berberine and coptisine occurred at concentrations of 0.2 μg/mL and 5.0μg/mL, respectively. At these concentrations, the effect seen was similar to that of a CAE at 100.0 μg/mL. Another five alkaloids within CAE, palmatine, epiberberine, jateorhizine, columbamine, and magnoline, were found to have a lower affinity for cellular components from HepG2 cells and a lower inhibition of TG accumulation. The finding of two potent and active compounds within CAE indicates that the screening method we developed is a feasible, rapid, and useful tool for studying traditional Chinese medicines (TCMs) in treating hepatic steatosis.

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44

Li, Jing, Dong-Min Qiu, Shao-Hua Chen, Su-Ping Cao, and Xue-Lan Xia. "Suppression of Human Breast Cancer Cell Metastasis by Coptisine in Vitro." Asian Pacific Journal of Cancer Prevention 15, no. 14 (July 30, 2014): 5747–51. http://dx.doi.org/10.7314/apjcp.2014.15.14.5747.

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45

Yu, Di, Shilong Fu, Zhifei Cao, Meimei Bao, Gaochuan Zhang, Yanyan Pan, Wenming Liu, and Quansheng Zhou. "Unraveling the novel anti-osteosarcoma function of coptisine and its mechanisms." Toxicology Letters 226, no. 3 (May 2014): 328–36. http://dx.doi.org/10.1016/j.toxlet.2014.02.021.

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46

Ro, Jai Seup, Sang Seon Lee, Kyong Soon Lee, and Myung Koo Lee. "Inhibition of type A monoamine oxidase by coptisine in mouse brain." Life Sciences 70, no. 6 (December 2001): 639–45. http://dx.doi.org/10.1016/s0024-3205(01)01437-0.

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47

Shi, Li-li, Wei-hua Jia, Li Zhang, Chun-yang Xu, Xi Chen, Lin Yin, Nuo-qi Wang, et al. "Glucose consumption assay discovers coptisine with beneficial effect on diabetic mice." European Journal of Pharmacology 859 (September 2019): 172523. http://dx.doi.org/10.1016/j.ejphar.2019.172523.

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48

Wu, Jiasi, Yu Luo, Donghang Deng, Siyu Su, Sheng Li, Li Xiang, Yingfan Hu, Ping Wang, and Xianli Meng. "Coptisine from Coptis chinensis exerts diverse beneficial properties: A concise review." Journal of Cellular and Molecular Medicine 23, no. 12 (October 17, 2019): 7946–60. http://dx.doi.org/10.1111/jcmm.14725.

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49

Zhou, Kai, Li Hu, Wenjun Liao, Defeng Yin та Feng Rui. "Coptisine Prevented IL-β-Induced Expression of Inflammatory Mediators in Chondrocytes". Inflammation 39, № 4 (13 червня 2016): 1558–65. http://dx.doi.org/10.1007/s10753-016-0391-6.

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50

Slavík, Jiří, and Leonora Slavíková. "Polar alkaloids from Papaver orientale L." Collection of Czechoslovak Chemical Communications 56, no. 7 (1991): 1534–38. http://dx.doi.org/10.1135/cccc19911534.

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Анотація:

Corytuberine (I) and quaternary alkaloids N-methylhebainium hydroxide (II), N-methylisothebainium hydroxide (III), and magnoflorine (IV) as iodides have been isolated for the first time from the fraction of strongly polar alkaloids obtained from aerial parts and roots of Papaver orientale L. The weakly polar fraction contains oripavine, thebaine, isothebaine, and alpinigenine as dominant components. Small amounts of bracteoline, isoboldine, scoulerine, papaverrubines G, A, B, D, and C, and traces of palmatine and coptisine have also been detected.

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