berberine alkaloids

Summary

Summary: A group of related plant alkaloids that contain the BERBERINE heterocyclic ring structure.

Top Publications

  1. Halbsguth C, Meissner O, Häberlein H. Positive cooperation of protoberberine type 2 alkaloids from Corydalis cava on the GABA(A) binding site. Planta Med. 2003;69:305-9 pubmed
    ..5 nM Mu-Alexa and 7.5 nM scoulerine showed a maximal increase of the specific Mu-Alexa binding of approximately 27 % by selectively modulating the amount of receptor-ligand complexes with a hindered mobility (9 % to 27 %)...
  2. Li Y, Fu L, Yao W, Xia G, Jiang M. Effects of benzyltetrahydropalmatine on two components of the delayed rectifier K+ current in Guinea pig ventricular myocytes. Cardiovasc Drugs Ther. 2002;16:317-25 pubmed
    ..It is concluded that BTHP prolonged the action potential duration with respect to its non-selective action on I(Kr) and I(Ks) in single guinea pig ventricular cell in a frequency-dependent fashion. ..
  3. Xing F, Song G, Ren J, Chaires J, Qu X. Molecular recognition of nucleic acids: coralyne binds strongly to poly(A). FEBS Lett. 2005;579:5035-9 pubmed
    ..Poly(A) forms a coralyne dependent secondary structure with a melting temperature of 60 degrees C, for the conditions of our study. ..
  4. Islam M, Pandya P, KUMAR S, Kumar G. RNA targeting through binding of small molecules: Studies on t-RNA binding by the cytotoxic protoberberine alkaloid coralyne. Mol Biosyst. 2009;5:244-54 pubmed publisher
    ..Docking studies provided further insights into the partially intercalated state of coralyne inside the t-RNA structure. This study presents a complete binding and thermodynamic profile of coralyne interaction to t-RNA. ..
  5. García B, Ibeas S, Ruiz R, Leal J, Biver T, Boggioni A, et al. Solvent effects on the thermodynamics and kinetics of coralyne self-aggregation. J Phys Chem B. 2009;113:188-96 pubmed publisher
    ..All of the results concur in elucidating the relevant role of the hydrophobic interaction process of coralyne stack formation. ..
  6. Maiti M, Kumar G. Molecular aspects on the interaction of protoberberine, benzophenanthridine, and aristolochia group of alkaloids with nucleic acid structures and biological perspectives. Med Res Rev. 2007;27:649-95 pubmed
    ..Nucleic acids binding properties of these alkaloids are interpreted in relation to their biological activity. ..
  7. Grycova L, Dostal J, Marek R. Quaternary protoberberine alkaloids. Phytochemistry. 2007;68:150-75 pubmed
    ..Currently, investigations in many laboratories worldwide are focused on the antibacterial and antimalarial activity, cytotoxicity, and potential genotoxicity of QPA. ..
  8. Kemeny Beke A, Aradi J, Damjanovich J, Beck Z, Facsko A, Berta A, et al. Apoptotic response of uveal melanoma cells upon treatment with chelidonine, sanguinarine and chelerythrine. Cancer Lett. 2006;237:67-75 pubmed
    ..This study is the first implication for the possible use of these alkaloids in the therapy of uveal melanomas, for which no really efficient therapeutic regimen is available so far. ..
  9. Giri P, Hossain M, Kumar G. Molecular aspects on the specific interaction of cytotoxic plant alkaloid palmatine to poly(A). Int J Biol Macromol. 2006;39:210-21 pubmed

More Information

Publications62

  1. Boudou M, Enders D. Asymmetric synthesis of tetrahydropalmatine via tandem 1,2-addition/cyclization. J Org Chem. 2005;70:9486-94 pubmed
    ..Finally, Pomeranz-Fritsch-type cyclization afforded the desired title compound (R)-(+)-2 in excellent enantioselectivity in 9% overall yield over seven steps and after optimization of the last step (S)-(-)-2 in 17% overall yield. ..
  2. Ihmels H, Faulhaber K, Vedaldi D, Dall Acqua F, Viola G. Intercalation of organic dye molecules into double-stranded DNA. Part 2: the annelated quinolizinium ion as a structural motif in DNA intercalators. Photochem Photobiol. 2005;81:1107-15 pubmed
    ..In addition, studies on the biological activities of annelated quinolizinium derivatives, such as topoisomerase poisoning or cell toxicity, are highlighted. ..
  3. Ernst E, Schmidt K. Ukrain - a new cancer cure? A systematic review of randomised clinical trials. BMC Cancer. 2005;5:69 pubmed
    ..Numerous pre-clinical and clinical investigations seem to suggest that Ukrain is pharmacologically active and clinically effective. We wanted therefore to critically evaluate the clinical trial data in the form of a systematic review...
  4. Cetinkol O, Hud N. Molecular recognition of poly(A) by small ligands: an alternative method of analysis reveals nanomolar, cooperative and shape-selective binding. Nucleic Acids Res. 2009;37:611-21 pubmed publisher
    ..The ligands described here may also find biological or medicinal applications, owing to the 3'-polyadenylation of mRNA in living cells. ..
  5. Islam M, Chowdhury S, Kumar G. Spectroscopic and calorimetric studies on the binding of alkaloids berberine, palmatine and coralyne to double stranded RNA polynucleotides. J Phys Chem B. 2009;113:1210-24 pubmed publisher
    ..These results further advance our understanding on the binding of small molecules that are specific binders to double stranded RNA sequences. ..
  6. Han M, Lytton Jean A, Mirkin C. A gold nanoparticle based approach for screening triplex DNA binders. J Am Chem Soc. 2006;128:4954-5 pubmed
    ..The assembly process and color change do not occur in the presence of duplex DNA binders and therefore provide a significantly better screening process for triplex DNA binding molecules compared to standard methods. ..
  7. Zein A, Dawe L, Georghiou P. Enantioselective total synthesis and X-ray structures of the tetrahydroprotoberberine alkaloids (-)-(S)-tetrahydropalmatrubine and (-)-(S)-corytenchine. J Nat Prod. 2010;73:1427-30 pubmed publisher
    ..They were both derived from (S)-N-norlaudanidine, a benzyltetrahydroisoquinoline that was synthesized with high (>95% ee) enantioselectivity using a chiral auxiliary-assisted Bischler-Napieralski cyclization/reduction approach. ..
  8. Jang S, Kim B, Lee W, An S, Choi H, Jeon B, et al. Stylopine from Chelidonium majus inhibits LPS-induced inflammatory mediators in RAW 264.7 cells. Arch Pharm Res. 2004;27:923-9 pubmed
    ..These biological activities of stylopine may contribute to the anti-inflammatory activity of Chelidonium majus...
  9. Jain S, Polak M, Hud N. Controlling nucleic acid secondary structure by intercalation: effects of DNA strand length on coralyne-driven duplex disproportionation. Nucleic Acids Res. 2003;31:4608-15 pubmed
    ..Together these observations indicate that at least one secondary structure in our nucleic acid system [i.e. duplex, triplex or (dA)n self-structure] binds coralyne in a length-dependent manner. ..
  10. Giri P, Kumar G. Binding of protoberberine alkaloid coralyne with double stranded poly(A): a biophysical study. Mol Biosyst. 2008;4:341-8 pubmed publisher
  11. Li Y, Wang S, Liu Y, Li Z, Yang X, Wang H, et al. Effect of alpha-allocryptopine on transient outward potassium current in rabbit ventricular myocytes. Cardiology. 2008;111:229-36 pubmed publisher
    ..2 +/- 1.2 to 4.7 +/- 0.6 pA/pF by 30 microM allocryptopine. Allocryptopine produced a blocking effect on the I(to) in cardiac myocytes, which may be an important mechanism in its antiarrhythmic effect. ..
  12. Sinha R, Kumar G. Interaction of isoquinoline alkaloids with an RNA triplex: structural and thermodynamic studies of berberine, palmatine, and coralyne binding to poly(U).poly(A)(*)poly(U). J Phys Chem B. 2009;113:13410-20 pubmed publisher
    ..84 and TDeltaS degrees = 7.44 kcal/mol) in coralyne. These results advance our knowledge on the binding of small molecule isoquinoline alkaloids that are specific binders of RNA structures, particularly triplexes. ..
  13. Cordes N, Blaese M, Plasswilm L, Rodemann H, Van Beuningen D. Fibronectin and laminin increase resistance to ionizing radiation and the cytotoxic drug Ukrain in human tumour and normal cells in vitro. Int J Radiat Biol. 2003;79:709-20 pubmed
    ..The data give the first mechanistic insights into specific FN- and LA-modulated cellular resistance mechanisms as well as into the important role for beta1-integrins using the unique cytotoxic and radiosensitivity-modifying drug Ukrain. ..
  14. Persil O, Santai C, Jain S, Hud N. Assembly of an antiparallel homo-adenine DNA duplex by small-molecule binding. J Am Chem Soc. 2004;126:8644-5 pubmed
    ..These observations illustrate that the helical structure of the homo-adenine-coralyne duplex is compatible with the B-form DNA helix. ..
  15. Lee D, Kang Y, Park M, Lee Y, Seo H, Kim T, et al. Effects of 13-alkyl-substituted berberine alkaloids on the expression of COX-II, TNF-alpha, iNOS, and IL-12 production in LPS-stimulated macrophages. Life Sci. 2003;73:1401-12 pubmed
  16. Grinevich Y, Shalimov S, Bendyuh G, Zahriychuk O, Hodysh Y. Effect of Ukrain on the growth and metastasizing of Lewis carcinoma in C57BL/6 mice. Drugs Exp Clin Res. 2005;31:59-70 pubmed
    ..Natural killer (NK) activity is one part of this resistance. NK cells are able to recognize and eliminate from the circulation cells with the potential to form metastases. ..
  17. Minami H, Kim J, Ikezawa N, Takemura T, Katayama T, Kumagai H, et al. Microbial production of plant benzylisoquinoline alkaloids. Proc Natl Acad Sci U S A. 2008;105:7393-8 pubmed publisher
  18. Winkler A, Lyskowski A, Riedl S, Puhl M, Kutchan T, Macheroux P, et al. A concerted mechanism for berberine bridge enzyme. Nat Chem Biol. 2008;4:739-41 pubmed publisher
    ..Here we propose a catalytic mechanism combining base-catalyzed proton abstraction with concerted carbon-carbon coupling accompanied by hydride transfer from the N-methyl group to the N5 atom of the FAD cofactor...
  19. Li C, Lu H, Lin C, Wu T. A rapid and simple determination of protoberberine alkaloids in cortex phellodendri by 1H NMR and its application for quality control of commercial traditional Chinese medicine prescriptions. J Pharm Biomed Anal. 2006;40:173-8 pubmed
  20. Jadhav V, Nayak S, Row T, Kulkarni M. Synthesis, structure and DNA cleavage studies of coumarin analogues of tetrahydroisoquinoline and protoberberine alkaloids. Eur J Med Chem. 2010;45:3575-80 pubmed publisher
    ..The results showed that compounds 6e, 6f, 7e and 7f were found to be very effective against DNA samples of Gram positive bacterium Staphylococcus aureus and fungus Aspergillus niger. ..
  21. Franceschin M, Rossetti L, D Ambrosio A, Schirripa S, Bianco A, Ortaggi G, et al. Natural and synthetic G-quadruplex interactive berberine derivatives. Bioorg Med Chem Lett. 2006;16:1707-11 pubmed
    ..The results show that these molecules have selectivity for G-quadruplex compared to duplex DNA, and that their aromatic moieties play a dominant role in quadruplex binding. ..
  22. Voltchek I, Kamyshentsev M, Lavinsky Y, Nowicky J, Medvedev Y, Litvinchuk L. Comparative study of the cytostatic effects of Oliphen and Ukrain. J Chemother. 1996;8:144-6 pubmed
    ..The proliferative activity of both normal cell cultures decreased in the presence of Oliphen and Ukrain concentrations of 0.1 and 0.015% and was stable at 0.0015 and 0.00015%. ..
  23. Nowicky J, Hiesmayr W, Nowicky W, Liepins A. Influence of Ukrain on DNA, RNA and protein synthesis in malignant cells. Drugs Exp Clin Res. 1996;22:81-91 pubmed
    ..YAC-1, P815 and human WiDr cells. Ukrain inhibits the DNA, RNA and protein synthesis in malignant cell lines at relatively high concentrations and to a small extent in normal cells. ..
  24. Panzer A, Joubert A, Bianchi P, Seegers J. The antimitotic effects of Ukrain, a Chelidonium majus alkaloid derivative, are reversible in vitro. Cancer Lett. 2000;150:85-92 pubmed
    ..We hypothesize that the lack of side-effects found in vivo may be due to the lack of therapeutically effective dosages being administered, therefore enabling cells to overcome the metaphase arrest and survive. ..
  25. Li Y, Fu L, Yao W, Xia G, Jiang M. Effects of benzyltetrahydropalmatine on potassium currents in guinea pig and rat ventricular myocytes. Acta Pharmacol Sin. 2002;23:612-6 pubmed
    ..9-4.3 micromol/L). (3) BTHP 200 micromol/L did not affect I(K1). BTHP inhibited I(Kr), I(Ks), and I(to), but not I(K1). The antiarrhythmic effects of BTHP may be mainly due to its blockade on potassium channels. ..
  26. Orfila L, Rodriguez M, Colman T, Hasegawa M, Merentes E, Arvelo F. Structural modification of berberine alkaloids in relation to cytotoxic activity in vitro. J Ethnopharmacol. 2000;71:449-56 pubmed
    ..On the other hand, these compounds showed a low selectivity for the different human cancer cell lines tested. ..
  27. Panzer A, Joubert A, Bianchi P, Hamel E, Seegers J. The effects of chelidonine on tubulin polymerisation, cell cycle progression and selected signal transmission pathways. Eur J Cell Biol. 2001;80:111-8 pubmed
    ..Exposure of all cell lines examined to chelidonine leads to activation of the stress-activated protein kinase/jun kinase pathway (SAPK/JNK). ..
  28. Gansauge F, Ramadani M, Pressmar J, Gansauge S, Muehling B, Stecker K, et al. NSC-631570 (Ukrain) in the palliative treatment of pancreatic cancer. Results of a phase II trial. Langenbecks Arch Surg. 2002;386:570-4 pubmed
    ..01). We could show that in unresectable advanced pancreatic cancer, NSC-631570 alone and in combination with gemcitabine nearly doubled the median survival times in patients suffering from advanced pancreatic cancer. ..
  29. Polak M, Hud N. Complete disproportionation of duplex poly(dT)*poly(dA) into triplex poly(dT)*poly(dA)*poly(dT) and poly(dA) by coralyne. Nucleic Acids Res. 2002;30:983-92 pubmed
    ..We propose that duplex disproportionation by coralyne is promoted by both the triplex and the poly(dA) self-structure having binding constants for coralyne that are greater than that of duplex poly(dT)*poly(dA). ..
  30. Kuznetsova L, Nikol skaia E, Sochilina E, Faddeeva M. [The inhibition enzymatic hydrolysis of acetylthiocholine by acetylcholinesterase using principal alkaloids isolated from celandine and macleya and their derivatives]. Tsitologiia. 2001;43:1046-50 pubmed
  31. Keppler M, Neidle S, Fox K. Stabilisation of TG- and AG-containing antiparallel DNA triplexes by triplex-binding ligands. Nucleic Acids Res. 2001;29:1935-42 pubmed
    ..The polycyclic compound BePI strongly stabilises TG- but not AG-containing triplexes, while a substituted naphthylquinoline interacts with both antiparallel triplex motifs. ..
  32. Voltchek I, Sologub T, Nowicky J, Grigoryeva T, Belozyorova L, Belopolskaya M, et al. Preliminary results of individual therapy of chronic hepatitis C by Ukrain and interferon-alpha. Drugs Exp Clin Res. 2000;26:261-6 pubmed
    ..5-fold in comparison with standard monotherapy with the same preparations, significantly decreased the number of side effects and dramatically improved cost-effectiveness. ..
  33. Cordes N, Plasswilm L, Bamberg M, Rodemann H. Ukrain, an alkaloid thiophosphoric acid derivative of Chelidonium majus L. protects human fibroblasts but not human tumour cells in vitro against ionizing radiation. Int J Radiat Biol. 2002;78:17-27 pubmed
    ..The effects of the drug on cell survival, alteration of the cell cycle and induction of apoptosis were examined without and in combination with ionizing radiation (IR). The TP53 status of the cell lines used was also investigated...
  34. Ko F, Guh J, Yu S, Hou Y, Wu Y, Teng C. (-)-Discretamine, a selective alpha 1D-adrenoceptor antagonist, isolated from Fissistigma glaucescens. Br J Pharmacol. 1994;112:1174-80 pubmed
    ..8. In conclusion, (-)-discretamine is a selective alpha lD-adrenoceptor antagonist in vascular smooth muscle.Its selectivity among various al-adrenoceptor subtypes is alpha 1A: alpha1B: alpha1D =0.04:0.07:1.0. ..
  35. Zemskov V, Prokopchuk O, Susak Y, Zemskov S, Tkachenko O, Hodysh Y, et al. Efficacy of ukrain in the treatment of pancreatic cancer. Langenbecks Arch Surg. 2002;387:84-9 pubmed
    ..Our data demonstrate that ukrain improves quality of life in patients suffering from advanced pancreatic cancer and significantly prolongs survival time in these patients. ..
  36. Das B, Tandon V, Lyndem L, Gray A, Ferro V. Phytochemicals from Flemingia vestita (Fabaceae) and Stephania glabra (Menispermeaceae) alter cGMP concentration in the cestode Raillietina echinobothrida. Comp Biochem Physiol C Toxicol Pharmacol. 2009;149:397-403 pubmed publisher
    ..vestita and S. glabra, respectively, disturb the downstream signalling pathway of NO, as indicated by the change in cGMP concentration in the parasite tissue...
  37. Qin Y, Chen W, Pang J, Zhao Z, Liu L, Jiang Z. DNA-binding affinities and sequence specificities of protoberberine alkaloids and their demethylated derivatives: a comparative study. Chem Biodivers. 2007;4:145-53 pubmed
    ..The binding mode of these alkaloids was further confirmed by UV spectroscopic titration experiments. All the compounds bind to double-stranded DNA most probably via an intercalating mode. ..
  38. Li W, Huang H, Niu X, Fan T, Mu Q, Li H. Protective effect of tetrahydrocoptisine against ethanol-induced gastric ulcer in mice. Toxicol Appl Pharmacol. 2013;272:21-9 pubmed publisher
    ..These results suggest that the gastroprotective activity of THC is attributed to reducing NO production and adjusting the pro-inflammatory cytokine, inhibited neutrophil accumulation and NF-?B expression. ..
  39. Dong J, Xie C, Tian R, Wu R, Hu J, Zou H. Capillary electrochromatography with a neutral monolithic column for classification of analytes and determination of basic drugs in human serum. Electrophoresis. 2005;26:3452-9 pubmed
    ..9995-0.9997) in the range of 0.318-80 microg/mL were obtained with the limits of detection being below 0.15 microg/mL. The intra- and inter-day precisions, determined as relative standard deviations, were less than 4.21%. ..
  40. Li Y, Zhao W, Wang Y, Zhang C, Jiang J, Bi C, et al. Discovery, synthesis and biological evaluation of cycloprotoberberine derivatives as potential antitumor agents. Eur J Med Chem. 2013;68:463-72 pubmed publisher
    ..G2/M phase arrest and tumor cell growth reduction was observed thereafter. Thus, we consider cycloprotoberberine analogues to be a new family of promising antitumor agents with an advantage of inhibiting drug-resistant cancer cells. ..
  41. Zhou C, Li J, Tan S, Ye H. Selective extraction of berberine and palmatine from Huangbai powder. Pak J Pharm Sci. 2013;26:1023-5 pubmed
    ..In addition, dichloromethane can be recycled and reused, making it a potential candidate for large scale extraction of berberine and palmatine from Huangbai. ..
  42. Wang J, Mantsch J. l-tetrahydropalamatine: a potential new medication for the treatment of cocaine addiction. Future Med Chem. 2012;4:177-86 pubmed publisher
    ..Finally, an overview of the safety profile of l-THP is provided and challenges associated with US FDA approval of l-THP are discussed. ..
  43. Gorner H, Miskolczy Z, Megyesi M, Biczók L. Photoreduction and ketone-sensitized reduction of alkaloids. Photochem Photobiol. 2011;87:284-91 pubmed publisher
    ..The quantum yield of conversion of alkaloids to dihydroalkaloids is enhanced in the presence of triethylamine. The reaction in the presence of ketones and electron or H-atom donors has a quantum yield of close to unity. ..
  44. Garriga R, Jurewicz I, Romero E, Jarne C, Cebolla V, Dalton A, et al. Two-Dimensional, pH-Responsive Oligoglycine-Based Nanocarriers. ACS Appl Mater Interfaces. 2016;8:1913-21 pubmed publisher
    ..Additionally, our results suggest that these planar self-assembled materials can also act as phase-transfer vehicles for hydrophobic cargoes further broadening their biomedical and technological applications. ..
  45. Zhao M, Xian Y, Ip S, Fong H, Che C. A new and weakly antispasmodic protoberberine alkaloid from Rhizoma Coptidis. Phytother Res. 2010;24:1414-6 pubmed publisher
    ..The new compound displayed weak antispasmodic activity against acetylcholine-induced contraction in isolated guinea-pig ileum with an IC50 of 83.7 microm. ..
  46. Liang Y, Yu C, Song J. Electrochemiluminescence of palmatine being oxidized by electrogenerated hydroxyl radical and its analytical application. Luminescence. 2011;26:178-84 pubmed publisher
    ..0 × 10(-7) to 2.0 × 10(-5) mol l(-1) and the limit of detection (signal-to-noise = 3) was 3 × 10(-7) mol l(-1) . The proposed method was applied to the determination of palmatine in pharmaceutical preparations. ..
  47. Schulze M, Siol O, Meise W, Lehmann J, Enzensperger C. Ring expansions of tetrahydroprotoberberines and related dibenzo[c,g]azecines modulate the dopamine receptor subtype affinity and selectivity. Arch Pharm (Weinheim). 2010;343:207-14 pubmed publisher
    ..Distances in energy-minimized conformations were measured in order to explain our findings. ..
  48. Le T, Cho W. First total synthesis of the phenolic 7,8-dihydro-8-oxoprotoberberine alkaloid, cerasonine. Chem Pharm Bull (Tokyo). 2008;56:1026-9 pubmed
    ..This key step provided the 3-arylisoquinoline which was then successfully converted to 7,8-dihydro-8-oxoprotoberberine through an intramolecular S(N)2 reaction. ..
  49. Islam M, Sinha R, Kumar G. RNA binding small molecules: studies on t-RNA binding by cytotoxic plant alkaloids berberine, palmatine and the comparison to ethidium. Biophys Chem. 2007;125:508-20 pubmed
    ..These results reveal the molecular aspects on the interaction of these alkaloids to t-RNA. ..
  50. Slobodníková L, Kost álová D, Labudová D, Kotulová D, Kettmann V. Antimicrobial activity of Mahonia aquifolium crude extract and its major isolated alkaloids. Phytother Res. 2004;18:674-6 pubmed
  51. Semwal D, Rawat U, Semwal R, Singh R, Singh G. Anti-hyperglycemic effect of 11-hydroxypalmatine, a palmatine derivative from Stephania glabra tubers. J Asian Nat Prod Res. 2010;12:99-105 pubmed publisher
    ..v.). The alloxan-induced diabetic mice showed significant reduction in blood glucose after treatment with the test compound by 52% as compared to the positive control glibenclamide (54%) and the diabetic control (27%)...
  52. Wang X, Dong H, Yang B, Liu D, Duan W, Huang L. Preparative isolation of alkaloids from Dactylicapnos scandens using pH-zone-refining counter-current chromatography by changing the length of the separation column. J Chromatogr B Analyt Technol Biomed Life Sci. 2011;879:3767-70 pubmed publisher
    ..0 g of the crude extracts and each with 99.2%, 96.5%, 99.3%, 99.5% purity as determined by HPLC. The chemical structures of these compounds were confirmed by positive ESI-MS and (1)H NMR...
  53. Khan A, Hossain M, Suresh Kumar G. Investigations on the interaction of the phototoxic alkaloid coralyne with serum albumins. Chemosphere. 2012;87:775-81 pubmed publisher
    ..The secondary structure of the proteins was altered, suggesting a small but definitive partial unfolding on complexation. ..