HPLC-based activity profiling for pharmacologically and toxicologically relevant natural products – principles and recent examples

References

• Allard P-M, Genta-Jouve G, Wolfender J-L. 2017. Deep metabolome annotation in natural products research: towards a virtuous cycle in metabolite identification. Curr Opin Chem Biol. 236:40–49.
   Web of Science ®Google Scholar
• Baburin I, Varkevisser R, Schramm A, Saxena P, Linder T, Stary-Weinzinger A, van der Heyden MAG, Houtman M, Takanari H, Jonsson M, et al. 2018. Dehydroevodiamine and hortiamine, alkaloids from the traditional Chinese herbal drug Evodia rutaecarpa, are IKr blockers with proarrhythmic effects in vitro and in vivo. Pharmacol Res. 131:150–163.
   PubMed Web of Science ®Google Scholar
• Barrera NP, Edwardson JM. 2008. The subunit arrangement and assembly of ionotropic receptors. Trends Neurosci. 31:569–576.
   PubMed Web of Science ®Google Scholar
• Bolton JL, Pisha E, Shen L, Krol ES, Iverson SL, Huang Z, van Breemen RB, Pezzuto JM. 1997. The reactivity of o-quinones which do not isomerize to quinone methides correlates with alkylcatechol-induced toxicity in human melanoma cells. Chem Biol Interact. 106:133–148.
   PubMed Web of Science ®Google Scholar
• Camp D, Davis RA, Campitelli M, Ebdon J, Quinn RJ. 2012. Drug-like properties: guiding principles for the design of natural product libraries. J Nat Prod. 75:72–81.
   PubMed Web of Science ®Google Scholar
• Chiou WF, Liao JF, Shum AYC, Chen CF. 1996. Mechanisms of vasorelaxant effect of dehydroevodiamine: a bioactive isoquinazolinocarboline alkaloid of plant origin. J Cardiovasc Pharm. 27:845–853.
   PubMed Web of Science ®Google Scholar
• da Silva RR, Wang M, Nothias L-F, van der Hooft JJJ, Caraballo-Rodríguez AM, Fox E, Balunas MJ, Klassen JL, Lopes NP, Dorrestein PC. 2018. Propagating annotations of molecular networks using in silico fragmentation. PLOS Comput Biol. 14:e1006089.
   PubMed Web of Science ®Google Scholar
• Dennis A, Wang L, Wan X, Ficker E. 2007. hERG channel trafficking: novel targets in drug-induced long QT syndrome. Biochem Soc Trans. 35:1060–1063.
   PubMed Web of Science ®Google Scholar
• Eigenmann DE, Dürig C, Jähne EA, Smiesko M, Culot M, Gosselet F, Cecchelli R, Helms HCC, Brodin B, Wimmer L, et al. 2016. In vitro blood–brain barrier permeability predictions for GABAA receptor modulating piperine analogs. Eur J Pharm Biopharm. 103:118–126.
   PubMed Web of Science ®Google Scholar
• Gintant G. 2011. An evaluation of hERG current assay performance: translating preclinical safety studies to clinical QT prolongation. Pharmacol Ther. 129:109–119.
   PubMed Web of Science ®Google Scholar
• Grabher P, Durieu E, Kouloura E, Halabaki M, Skaltsounis LA, Meijer L, Hamburger M, Potterat O. 2012. Library-based discovery of DYRK1A/CLK1 inhibitors from natural product extracts. Planta Med. 78:951–956.
   PubMed Web of Science ®Google Scholar
• Hancox JC, McPate MJ, El Harchi A, Zhang YH. 2008. The hERG potassium channel and hERG screening for drug-induced torsades de pointes. Pharmacol Ther. 119:118–132.
   PubMed Web of Science ®Google Scholar
• Harmati G, Papp F, Szentandrássy N, Bárándi L, Ruzsnavszky F, Horváth B, Bányász T, Magyar J, Panyi G, Krasznai Z, et al. 2011. Effects of the PKC inhibitors chelerythrine and bisindolylmaleimide I (GF 109203X) on delayed rectifier K+ currents. Naunyn-Schmiedeberg’s Arch Pharmacol. 383:141–148.
   Google Scholar
• Hu CW, Sheng Y, Zhang Q, Liu HB, Xie X, Ma WC, Huo R, Dong DL. 2012. Curcumin inhibits hERG potassium channels in vitro. Toxicol Lett. 208:192–196.
   PubMed Web of Science ®Google Scholar
• Huang X, Li W, Yang XW. 2012. New cytotoxic quinolone alkaloids from fruits of Evodia rutaecarpa. Fitoterapia. 83:709–714.
   PubMed Web of Science ®Google Scholar
• Jeong I, Choi BH, Hahn SJ. 2010. Effects of lobeline, a nicotinic receptor ligand, on the cloned Kv1.5. Pflugers Archiv: Eur J Physiol. 460:851–862.
   PubMed Web of Science ®Google Scholar
• Khom S, Strommer B, Schöffmann A, Hintersteiner J, Baburin I, Erker T, Schwarz T, Schwarzer C, Zaugg J, Hamburger M, et al. 2013. GABAA receptor modulation by piperine and a non-TRPV1 activating derivative. Biochem Pharmacol. 85:1827–1836.
   PubMed Web of Science ®Google Scholar
• Kim HJ, Baburin I, Khom S, Hering S, Hamburger M. 2008. HPLC-based activity profiling approach for the discovery of GABAA receptor ligands using an automated two microelectrode voltage clamp assay on Xenopus oocytes. Planta Med. 74:521–526.
   PubMed Web of Science ®Google Scholar
• Kim YJ, Hong HK, Lee HS, Moh SH, Park JC, Jo SH, Choe H. 2008. Papaverine, a vasodilator, blocks the pore of the hERG channel at submicromolar concentration. J Cardiovasc Pharm. 52:485–493.
   PubMed Web of Science ®Google Scholar
• Lin C, Ke X, Ranade V, Somberg J. 2008. The additive effects of the active component of grapefruit juice (naringenin) and antiarrhythmic drugs on hERG inhibition. Cardiology. 110:145–152.
   PubMed Web of Science ®Google Scholar
• Lin CI, Loh SH, Luk HN, Lue WM, Chen CF. 1990. Electropharmacological effects of dehydroevodiamine on mammalian hearts. J Chin Med. 1:84–93.
   Google Scholar
• Liu Y, Xu XH, Liu Z, Du XL, Chen KH, Xin X, Jin ZD, Shen JZ, Hu Y, Li GR, et al. 2012. Effects of the natural flavone trimethylapigenin on cardiac potassium currents. Biochem Pharmacol. 84:498–506.
   PubMed Web of Science ®Google Scholar
• Moradi-Afrapoli F, Ebrahimi SN, Smiesko M, Hamburger M. 2017. HPLC-based activity profiling for GABAA receptor modulators in extracts: validation of an approach utilizing a larval zebrafish locomotor assay. J Nat Prod. 80:1548–1557.
   PubMed Web of Science ®Google Scholar
• Newman DJ, Cragg GM. 2012. Natural products as sources of new drugs over the 30 years from 1981 to 2010. J Nat Prod. 75:311–335.
   PubMed Web of Science ®Google Scholar
• Olsen RW, Sieghart W. 2008. International Union of Pharmacology. LXX. Subtypes of gamma-aminobutyric acid(A) receptors: classification on the basis of subunit composition, pharmacology, and function. Update. Pharmacol Rev. 60:243–260.
   PubMed Web of Science ®Google Scholar
• Piccirillo G, Magrì D, Matera S, Magnanti M, Pasquazzi E, Schifano E, Velitti S, Mitra M, Marigliano V, Paroli M, et al. 2008. Effects of pink grapefruit juice on QT variability in patients with dilated or hypertensive cardiomyopathy and in healthy subjects. Transl Res. 151:267–272.
   PubMed Web of Science ®Google Scholar
• Potterat O, Hamburger M. 2013. Concepts and technologies for tracking bioactive compounds in natural product extracts: generation of libraries, and hyphenation of analytical processes with bioassays. Nat Prod Rep. 30:546–564.
   PubMed Web of Science ®Google Scholar
• Potterat O, Hamburger M. 2014. Combined use of extract libraries and HPLC-based activity profiling for lead discovery: potential, challenges, and practical considerations. Planta Med. 80:1171–1181.
   PubMed Web of Science ®Google Scholar
• Riss J, Cloyd J, Gates J, Collins S. 2008. Benzodiazepines in epilepsy: pharmacology and pharmacokinetics. Acta Neurol Scand. 118:69–86.
   PubMed Web of Science ®Google Scholar
• Sanguinetti MC, Tristani-Firouzi M. 2006. hERG potassium channels and cardiac arrhythmia. Nature. 440:463–469.
   PubMed Web of Science ®Google Scholar
• Schöffmann A, Wimmer L, Goldmann D, Khom S, Hintersteiner J, Baburin I, Schwarz T, Hintersteininger M, Pakfeifer P, Oufir M, et al. 2014. Efficient modulation of γ-aminobutyric acid type A receptors by piperine derivatives. J Med Chem. 57:5602–5619.
   PubMed Web of Science ®Google Scholar
• Schramm A, Baburin I, Hering S, Hamburger M. 2011. hERG channel inhibitors in extracts of Coptidis rhizoma. Planta Med. 77:692–697.
   PubMed Web of Science ®Google Scholar
• Schramm A, Hamburger M. 2014. Gram-scale purification of dehydroevodiamine from Evodia rutaecarpa fruits, and a procedure for selective removal of quaternary indoloquinazoline alkaloids from Evodia extracts. Fitoterapia. 94:127–133.
   PubMed Web of Science ®Google Scholar
• Schramm A, Jähne EA, Baburin I, Hering S, Hamburger M. 2014b. Natural products as potential hERG channel inhibitors – outcomes from a screening of widely used herbal medicines and edible plants. Planta Med. 80:1045–1050.
   PubMed Web of Science ®Google Scholar
• Schramm A, Saxena P, Chlebek J, Cahlíková L, Baburin I, Hering S, Hamburger M. 2014a. Natural products as potential hERG channel inhibitors – screening of plant-derived alkaloids. Planta Med. 80:740–746.
   PubMed Web of Science ®Google Scholar
• Sieghart W, Sperk G. 2002. Subunit composition, distribution and function of GABA(A) receptor subtypes. Curr Top Med Chem. 2:795–816.
   PubMedGoogle Scholar
• Simon J, Wakimoto H, Fujita N, Lalande M, Barnard EA. 2004. Analysis of the set of GABA(A) receptor genes in the human genome. J Biol Chem. 279:41422–41435.
   PubMed Web of Science ®Google Scholar
• Sugimoto T, Miyase T, Kuroyanagi M, Ueno A. 1988. Limonoids and quinolone alkaloids from Evodia rutaecarpa Bentham. Chem Pharm Bull. 36:4453–4461.
   Web of Science ®Google Scholar
• Wang YF, Liu YN, Hu LM, Pan GX, Gao XM. 2011. A qualitative and quantitative assessment of eight constituents in Fructus Evodiae by HPLC-DAD-ESI-MS/MS. J Liq Chromatogr Relat Technol. 34:408–420.
   Web of Science ®Google Scholar
• Wang XX, Zan K, Shi SP, Zeng KW, Jiang Y, Guan Y, Xiao CL, Gao HY, Wu LJ, Tu PF. 2013. Quinolone alkaloids with antibacterial and cytotoxic activities from the fruits of Evodia rutaecarpa. Fitoterapia. 89:1–7.
   PubMed Web of Science ®Google Scholar
• Whiting PJ. 2006. GABA-A receptors: a viable target for novel anxiolytics? Curr Opin Pharmacol. 6:24–29.
   PubMed Web of Science ®Google Scholar
• Wimmer L, Schönbauer D, Pakfeifer P, Schöffmann A, Khom S, Hering S, Mihovilovic MD. 2015. Developing piperine towards TRPV1 and GABAA receptor ligands-synthesis of piperine analogs via Heck-coupling of conjugated dienes. Org Biomol Chem. 13:990–994.
   PubMed Web of Science ®Google Scholar
• Xing JL, Ma JH, Zhang PH, Fan XR. 2010. Block effect of capsaicin on hERG potassium currents is enhanced by S6 mutation at Y652. Eur J Pharmacol. 630:1–9.
   PubMed Web of Science ®Google Scholar
• Yang HY, Li SY, Chen CF. 1988. Hypotensive effects of dehydroevodiamine, a quinazolinocarboline alkaloid isolated from Evodia rutaecarpa. Asia Pac J Pharmacol. 3:191–196.
   Google Scholar
• Yang MCM, Wu SL, Kuo JS, Chen CF. 1990. The hypotensive and negative chronotropic effects of dehydroevodiamine. Eur J Pharmacol. 182:537–542.
   PubMed Web of Science ®Google Scholar
• Zabela V, Hettich T, Schlotterbeck G, Wimmer L, Mihovilovic MD, Guillet F, Bouaita B, Shevchenko B, Hamburger M, Oufir M. 2018. GABAA receptor activity modulating piperine analogs: in vitro metabolic stability, metabolite identification, CYP450 reaction phenotyping, and protein binding. J Chromatogr B. 1072:379–389.
   PubMed Web of Science ®Google Scholar
• Zaugg J, Baburin I, Strommer B, Kim H-J, Hering S, Hamburger M. 2010. HPLC-based activity profiling: discovery of piperine as a positive GABAA receptor modulator targeting a benzodiazepine-independent binding site. J Nat Prod. 73:185–191.
   PubMed Web of Science ®Google Scholar
• Zitron E, Scholz E, Owen RW, Lück S, Kiesecker C, Thomas D, Kathöfer S, Niroomand F, Kiehn J, Kreye VAW, et al. 2005. QTc prolongation by grapefruit juice and its potential pharmacological basis: hERG channel blockade by flavonoids. Circulation. 111:835–838.
   PubMed Web of Science ®Google Scholar