Analysis of benzo[c]phenanthridine alkaloids in Eschscholtzia californica cell culture using HPLC-DAD and HPLC-ESI-MS/MS

References

• Schmeller T, Latz-Bruning B, Wink M. Biochemical activities of berberine, palmatine and sanguinarine mediating chemical defence against microorganisms and herbivores. Phytochemistry. 1997;44(2):257–266.10.1016/S0031-9422(96)00545-6
   PubMed Web of Science ®Google Scholar
• Muller-Jakic B, Muller M, Probstle A, Johns TA, Bauer R. Anti-inflammatory activity of Zanthoxylum chalybeum extracts and identification of protoberberine and benzophenanthridine alkaloids by GC-MS and HPLC. Planta Med. 1993;59:A664.10.1055/s-2006-959934
   Google Scholar
• Sacchetti B, Bielavska E. Chelerythrine, a specific PKC inhibitor, blocks acquisition but not consolidation and retrieval of conditioned taste aversion in rat. Brain Res. 1998;799:84–90.10.1016/S0006-8993(98)00460-0
   PubMed Web of Science ®Google Scholar
• Vrba J, Doležel P, Vičar J, Modrianský M, Ulrichová J. Chelerythrine and dihydrochelerythrine induce G1 phase arrest and bimodal cell death in human leukemia HL-60 cells. Toxicol. in Vitro. 2008;22:1008–1017.10.1016/j.tiv.2008.02.007
   PubMed Web of Science ®Google Scholar
• Tanahashi T, Zenk MH. New hydroxylated benzo[c]phenanthridine alkaloids from Eschscholtzia californica cell suspension cultures. J. Nat. Prod. 1990;53:579–586.10.1021/np50069a007
   PubMed Web of Science ®Google Scholar
• Schumacher HM, Gundlach H, Fiedler F, Zenk MH. Elicitation of benzophenanthridine alkaloid synthesis in Eschscholtzia cell cultures. Plant Cell Rep. 1987;6(6):410–413.
   PubMed Web of Science ®Google Scholar
• Kolewe ME, Gaurav V, Roberts SC. Pharmaceutically active natural product synthesis and supply via plant cell culture technology. Mol. Pharm. 2008;5:243–256.10.1021/mp7001494
   PubMed Web of Science ®Google Scholar
• Chen Y-Z, Liu G-Z, Shen Y, Chen B, Zeng J-G. Analysis of alkaloids in Macleaya cordata (Willd.) R. Br. using high-performance liquid chromatography with diode array detection and electrospray ionization mass spectrometry. J Chromatogr A. 2009;1216:2104–2110.10.1016/j.chroma.2008.08.066
   PubMed Web of Science ®Google Scholar
• Fabre N, Claparols C, Richelme S, Angelin M-L, Fourasté I, Moulis C. Direct characterization of isoquinoline alkaloids in a crude plant extract by ion-pair liquid chromatography–electrospray ionization tandem mass spectrometry: example of Eschscholtzia californica. J. Chromatogr. A. 2000;904:35–46.10.1016/S0021-9673(00)00919-5
   PubMed Web of Science ®Google Scholar
• Suchomelová J, Bochořáková H, Paulová H, Musil P, Táborská E. HPLC quantification of seven quaternary benzo[c]phenanthridine alkaloids in six species of the family Papaveraceae. J. Pharm. Biomed. Anal. 2007;44:283–287.10.1016/j.jpba.2007.02.005
   PubMed Web of Science ®Google Scholar
• A-j Deng, H-l Qin. Cytotoxic dihydrobenzophenanthridine alkaloids from the roots of Macleaya microcarpa. Phytochemistry. 2010;71:816–822.
   PubMed Web of Science ®Google Scholar
• Ahn MJ, Lee MK, Kim YC, Sung SH. The simultaneous determination of coumarins in Angelica gigas root by high performance liquid chromatography–diode array detector coupled with electrospray ionization/mass spectrometry. J Pharmaceut Biomed. 2008;46(2):258–266.10.1016/j.jpba.2007.09.020
   PubMed Web of Science ®Google Scholar
• Sun Z, Song C, Xia L, Wang X, Suo Y, You J. Comprehensive comparisons between 1-Phenyl-3-methyl-5-pyrazolones, 1-(4-Methoxyphenyl)-3-methyl-5-pyrazolones and 1-(2-Naphthyl)-3-methyl-5- pyrazolones as labeling reagents used in LC-DAD-ESI-MS-MS analysis of neutral aldoses and uronic acids. Chromatographia. 2010;71:789–797.10.1365/s10337-010-1570-5
   Web of Science ®Google Scholar
• Cho HY, Son SY, Rhee HS, Yoon SYH, Lee-Parsons CWT, Park JM. Synergistic effects of sequential treatment with methyl jasmonate, salicylic acid and yeast extract on benzophenanthridine alkaloid accumulation and protein expression in Eschscholtzia californica suspension cultures. J. Biotechnol. 2008;135:117–122.10.1016/j.jbiotec.2008.02.020
   PubMed Web of Science ®Google Scholar
• Weiss D, Baumert A, Vogel M, Roos W. Sanguinarine reductase, a key enzyme of benzophenanthridine detoxification. Plant Cell Environ. 2006;29:291–302.10.1111/pce.2006.29.issue-2
   PubMed Web of Science ®Google Scholar
• Park JJ, Yoon SYH, Cho HY, Son SY, Rhee HS, Park JM. Patterns of protein expression upon adding sugar and elicitor to the cell culture of Eschscholtzia californica. Plant Cell Tiss. Org. Cult. 2006;86:257–269.10.1007/s11240-006-9115-1
   Web of Science ®Google Scholar
• Psotova J, Klejdus B, Vecera R, Kosina P, Kuban V, Vicar J, Simanek V, Ulrichova J. A liquid chromatographic–mass spectrometric evidence of dihydrosanguinarine as a first metabolite of sanguinarine transformation in rat. J Chromatogr B. 2006;830:165–172.10.1016/j.jchromb.2005.10.030
   PubMed Web of Science ®Google Scholar
• Howell CR, Stipanovic RD, Bell AA. Dihydrosanguinarine, a product of sanguinarine detoxification by Verticillium dahliae. Pestic Biochem Physiol. 1972;2:364–370.10.1016/0048-3575(72)90041-7
   Web of Science ®Google Scholar
• Das A, Nandi R, Maiti M. Photophysical property of sanguinarine in the excited singlet state. Photochem. Photobiol. 1992;56:311–317.10.1111/php.1992.56.issue-3
   PubMed Web of Science ®Google Scholar
• Oldham JT, Hincapie M, Rejtar T, Wall PK, Carlson JE, Lee-Parsons CWT. Shotgun proteomic analysis of yeast-elicited California poppy (Eschscholzia californica) suspension cultures producing enhanced levels of benzophenanthridine alkaloids. J. Proteome Res. 2010;9:4337–4345.10.1021/pr1000412
   PubMed Web of Science ®Google Scholar
• Han L-F, Nowicky W, Gutmann V. Reversed-phase high-performance liquid chromatographic separation of tertiary and quaternary alkaloids from Chelidonium majus L. J. Chromatogr. A. 1991;543:123–128.10.1016/S0021-9673(01)95760-7
   Web of Science ®Google Scholar
• Gathungu RM, Oldham JT, Bird SS, Lee-Parsons CWT, Vouros P, Kautz R. Application of an integrated LC-UV-MS-NMR platform to the identification of secondary metabolites from cell cultures: benzophenanthridine alkaloids from elicited Eschscholzia californica (california poppy) cell cultures. Anal. Methods. 2012;4:1315–1325.10.1039/c2ay05803k
   PubMed Web of Science ®Google Scholar
• Archambault J, Williams RD, Bédard C, Chavarie C. Production of sanguinarine by elicited plant cell culture I. Shake flask suspension cultures. J. Biotechnol. 1996;46:95–105.10.1016/0168-1656(95)00184-0
   Web of Science ®Google Scholar
• Rho D, Chauret N, Laberge N, Archambault J. Growth characteristics of Sanguinaria canadensis L. Cell suspensions and immobilized cultures for production of benzophenanthridine alkaloids. Appl. Microbiol. Biot. 1992;36(5):611–617.
   PubMed Web of Science ®Google Scholar