Hyperforin production in Hypericum perforatum root cultures

Journal of Biotechnology - Tập 222 - Trang 47-55 - 2016
Mariam Gaid1,2, Paul Haas3,2, Till Beuerle1,2, Stephan Scholl3,2, Ludger Beerhues1,2
1Institute of Pharmaceutical Biology, Technische Universität Braunschweig, Braunschweig, Germany
2Center of Pharmaceutical Engineering, Technische Universität Braunschweig, Braunschweig, Germany
3Institute of Chemical and Thermal Process Engineering, Technische Universität Braunschweig, Braunschweig, Germany

Tài liệu tham khảo

Bruni, 2009, Factors affecting polyphenol biosynthesis in wild and field grown St. John’s Wort (Hypericum perforatum L., Hypericaceae/Guttiferae), Molecules, 14, 682, 10.3390/molecules14020682 Charchoglyan, 2007, Differential accumulation of hyperforin and secohyperforin in Hypericum perforatum tissue cultures, Phytochemistry, 68, 2670, 10.1016/j.phytochem.2007.06.004 Chatterjee, S.S., Erdelmeier, C., Klessing, K., Marme, D., Schachtele, C., 2002. Stable hyperforin salts, method for producing same and their use in the treatment of Alzheimer's disease. United States Patent 6,444,662 B1, 2002. Cui, 2010, Production of adventitious roots and secondary metabolites by Hypericum perforatum L. in a bioreactor, Bioresour. Technol., 101, 4708, 10.1016/j.biortech.2010.01.115 Cui, 2011, Production of adventitious root biomass and secondary metabolites of Hypericum perforatum L. in a balloon type airlift reactor, Bioresour. Technol., 102, 10072, 10.1016/j.biortech.2011.08.044 Cui, 2014, Pilot-scale culture of Hypericum perforatum L. adventitious roots in airlift bioreactors for the production of bioactive compounds, Appl. Biochem. Biotechnol., 174, 784, 10.1007/s12010-014-1123-8 Dias, 2003, The potential of in vitro cultures of Hypericum perforatum and of Hypericum androsaemum to produce interesting pharmaceutical compounds, 137 Erdelmeier, 1999, New hyperforin analogues from Hypericum perforatum and a stable dicyclohexylammonium salt of hyperforin, 432 Fukuyama, 1997, Garsubellin A, a novel polyprenylated phloroglucin derivative, increasing choline acetyltransferase (ChAT) activity in postnatal rat septal neuron cultures, Chem. Pharm. Bull., 45, 947, 10.1248/cpb.45.947 Fuzzati, 2001, High-performance liquid chromatography–electrospray ionisation mass spectrometry and multiple mass spectrometry studies of hyperforin degradation products, J. Chromatogr. A, 926, 187, 10.1016/S0021-9673(01)01000-7 Gamborg, 1968, Nutrient requirements of suspension cultures of soybean root cells, Exp. Cell Res., 50, 151, 10.1016/0014-4827(68)90403-5 Hölscher, 2009, Matrix-free UV-laser desorption/ionization (LDI) mass spectrometric imaging at the single-cell level: distribution of secondary metabolites in Arabidopsis thaliana and Hypericum species, Plant J., 60, 907, 10.1111/j.1365-313X.2009.04012.x Hofrichter, 2013, Reduced Alzheimer’s disease pathology by St. John’s Wort treatment is independent of hyperforin and facilitated by ABCC1 and microglia activation in mice, Curr. Alzheimer Res., 10, 1057, 10.2174/15672050113106660171 Karioti, 2010, Hypericins as potential leads for new therapeutics, Int. J. Mol. Sci., 11, 562, 10.3390/ijms11020562 Karppinen, 2007, Biosynthesis of hyperforin and adhyperforin from amino acid precursors in shoot cultures of Hypericum perforatum, Phytochemistry, 68, 1038, 10.1016/j.phytochem.2007.01.001 Klingauf, 2005, Biosynthesis of the hyperforin skeleton in Hypericum calycinum cell cultures, Phytochemistry, 66, 139, 10.1016/j.phytochem.2004.11.003 Košuth, 2003, The content of hypericins and phloroglucinols in Hypericum perforatum L. seedlings at early stage of development, Plant Sci., 165, 515, 10.1016/S0168-9452(03)00210-3 Leuner, 2007, Hyperforin–a key constituent of St. John’s Wort specifically activates TRPC6 channels, FASEB J., 21, 4101, 10.1096/fj.07-8110com Liu, 2005, Liquid chromatography–mass spectrometry studies of St. John’s Wort methanol extraction: active constituents and their transformation, J. Pharm. Biomed. Anal., 37, 303, 10.1016/j.jpba.2004.10.034 Müller, 2008, Specific TRPC6 channel activation, a novel approach to stimulate keratinocyte differentiation, J. Biol. Chem., 283, 33942, 10.1074/jbc.M801844200 Murashige, 1962, A revised medium for rapid growth and bioassays with tobacco tissue cultures, Physiol. Plant., 15, 473, 10.1111/j.1399-3054.1962.tb08052.x Murthy, 2014, Hypericins: biotechnological production from cell and organ cultures, Appl. Microbiol. Biotechnol., 98, 9187, 10.1007/s00253-014-6119-3 Nahrstedt, 2010, Lessons learned from herbal medicinal products: the example of St. John’s Wort, J. Nat. Prod., 73, 1015, 10.1021/np1000329 Orth, 1999, Isolation, purity analysis and stability of hyperforin as a standard material from Hypericum perforatum L, J. Pharm. Pharmacol., 51, 193, 10.1211/0022357991772132 Piovan, 2004, Detection of hypericins in the red glands of Hypericum elodes by ESI–MS/MS, Phytochemistry, 65, 411, 10.1016/j.phytochem.2003.11.003 Pirker, 2002, Simultaneous determination of hypericin and hyperforin in human plasma and serum using liquid–liquid extraction, high-performance liquid chromatography and liquid chromatography–tandem mass spectrometry, J. Chromatogr. B, 777, 147, 10.1016/S1570-0232(02)00080-6 Ritz, 2012, In vitro comparison of hypericin and 5-aminolevulinic acid-derived protoporphyrin IX for photodynamic inactivation of medulloblastoma cells, PLoS One, 7, e51974, 10.1371/journal.pone.0051974 Russo, 2014, Hypericum perforatum: pharmacokinetic, mechanism of action, tolerability, and clinical drug–drug interactions, Phytother. Res., 28, 643, 10.1002/ptr.5050 Schiavone, 2013, Biological evaluation of hyperforin and its hydrogenated analogue on bacterial growth and biofilm production, J. Nat. Prod., 76, 1819, 10.1021/np400394c Schiavone, 2014, Anticancer and antibacterial activity of hyperforin and its derivatives, Anti-Cancer Agents Med. Chem., 14, 1397, 10.2174/1871520614999140829122803 Schmidt, 2008, Combining PARAFAC analysis of HPLC-PDA profiles and structural characterization using HPLC-PDA-SPE-NMR-MS experiments: commercial preparations of St. John’s Wort, Anal. Chem., 80, 1978, 10.1021/ac702064p Sirvent, 2003, Induction of hypericins and hyperforins in Hypericum perforatum in response to damage by herbivores, J. Chem. Ecol., 29, 2667, 10.1023/B:JOEC.0000008011.77213.64 Smelcerovic, 2006, Comparison of methods for the exhaustive extraction of hypericins, flavonoids, and hyperforin from Hypericum perforatum L/, J. Agric. Food Chem., 54, 2750, 10.1021/jf0527246 Soelberg, 2007, Hyperforin accumulates in the translucent glands of Hypericum perforatum, Ann. Bot., 99, 1097, 10.1093/aob/mcm057 Stojanović, 2013, Do other Hypericum species have medical potential as St. John's Wort (Hypericum perforatum)?, Curr. Med. Chem., 20, 2273, 10.2174/0929867311320180001 Tatsis, 2007, Identification of the major constituents of Hypericum perforatum by LC/SPE/NMR and/or LC/MS, Phytochemistry, 68, 383, 10.1016/j.phytochem.2006.11.026 Teotico, 2008, Structural basis of human pregnane X receptor activation by the hops constituent colupulone, Mol. Pharmacol., 74, 1512, 10.1124/mol.108.050732 Ting, 2015, Total synthesis of hyperforin, J. Am. Chem. Soc., 137, 10516, 10.1021/jacs.5b06939 Verotta, 2002, Synthesis and biological evaluation of hyperforin analogues. Part I. Modification of the enolized cyclohexanedione moiety, J. Nat. Prod., 65, 433, 10.1021/np0105681 Wölfle, 2014, Topical application of St. John’s Wort (Hypericum perforatum), Planta Med., 80, 109 Wolfender, 2003, Structural investigations of isomeric oxidised forms of hyperforin by HPLC-NMR and HPLC-MS, Phytochem. Anal., 14, 290, 10.1002/pca.718 Wu, 2014, Several factors affecting hypericin production of Hypericum perforatum during adventitious root culture in airlift bioreactors, Acta Physiol. Plant., 36, 975, 10.1007/s11738-013-1476-6 Zhang, 2004, Direct characterization of bitter acids in a crude hop extract by liquid chromatography-atmospheric pressure chemical ionization mass spectrometry, J. Am. Soc. Mass Spectrom., 15, 180, 10.1016/j.jasms.2003.09.014 Zobayed, 2003, Elevated carbon supply altered hypericin and hyperforin contents of St. John’s Wort (Hypericum perforatum) grown in bioreactors, Plant Cell Tiss. Org. Cult., 75, 143, 10.1023/A:1025053427371