Macleaya microcarpa (Maxim.) Fedde belongs to the genus Macleaya, family Papaveraceae. Together with the better known and more frequently studied species M. cordata (Willd.) R. Br. it is a main source of quaternary benzo[c]phenanthridine alkaloids. Using HPLC we determined the content of eight isoquinoline alkaloids in the aerial and underground parts of 1-, 2-, 12- and 13-year old plants and followed their changes during the vegetative period. The dominant alkaloid of all samples collected in the end of this period was allocryptopine (3.8-13.6 mg/g for aerial parts, 24.2-48.9 mg/g for underground parts). Chelerythrine, sanguinarine and protopine were also present in both parts of the plant. Additionally, measurable concentrations of chelilutine (CL), chelirubine (CR), macarpine (MA) and sanguirubine (SR) were detected in underground parts. The most important finding was that contents of CR, CL, SR and MA in the 12- and 13-year old plant roots were significantly higher (approximately 3-fold for CR, 6-fold for CL, 5-fold for SR, and at least 14-fold for MA) than in 1- or 2-year old plants. The proportion of individual alkaloids in aerial and underground parts thus changed significantly during the vegetative period.

Department of Biochemistry Faculty of Medicine Masaryk University Brno Czech Republic

Zobrazit více v PubMed

Slavík J., Slavíková L. Papaveraceae alkaloids VI. On alkaloids of Macleaya microcarpa (Maxim) Fedde. Chem. Listy. 1954;48:106–110. in Czech.

Zhang M., Grey-Wilson C. Bo Lu Hui Shu (in Chinese) [(Accessed: December,2010)];Flora China. 2008 7:287–288. Available online: http://flora.huh.harvard.edu/china/PDF/PDF07/Macleaya.pdf.

Katz A.W. Perennials for Midwestern Gardens: Proven Plants for the Heartland. Timber Press; Portland, Oregon: 2008.

Kosina P., Gregorova J., Gruz J., Vacek J., Kolard M., Vogele M., Roose W., Naumannf K., Simaneka V., Ulrichovaa J. Phytochemical and antimicrobial characterization of Macleaya cordata herb. Fitoterapia. 2010;81:1006–1012. doi: 10.1016/j.fitote.2010.06.020. PubMed DOI

Liu Q., Liu Y., Guo M., Lou X., Yao S. A simple and sensitive Metod of nonaqueouscapillary electrophoresis with laser-induced native fluorescence detection for the analysisof chelerythrine and sanguinarine in Chinese herbal medicines. Talanta. 2006;70:202–207. doi: 10.1016/j.talanta.2006.02.049. PubMed DOI

Pi G., Ren P., Yu J., Shi R., Yuan Z., Wang C. Separation of sanguinarine and chelerythrine in Macleaya cordata (Willd) R. Br. based on methyl acrylate-co-divinylbenzen macroporous adsorbents. J. Chromatogr. A. 2008;1192:17–24. PubMed

Zhang F., Chen B., Xiao S., Yao S. Optimatization and comparsion of different extraction techniques for sanguinarine and chelerythrine in fruits of Macleaya cordata (Willd) R. Br. Sep. Purif. Technol. 2005;42:283–290. doi: 10.1016/j.seppur.2004.09.002. DOI

Faddeieva M.D., Beliaeva T.N. Sanguinarine and ellipticine: cytotoxic alkaloids isolated from well-known antitumor plants. Intracellular targets of their action. Tsitologiya. 1997;39:181–208. PubMed

Zdarilova A., Vrablova E., Vostalova J., Klejdus B., Stejskal D., Proskova J., Kosina P., Svobodova A., Vecera R., Hrbac J., Cernochova D., Vicar J., Ulrichova J., Šimánek V. Natural feed additive of Macleaya cordata: Safety assessment in rats a 90-day Frediny experiment. Food Chem. Toxicol. 2008;46:3721–3726. PubMed

Zdunczyk Z., Gruzauskas R., Juskiewicz J., Semaskaite A., Jankowski J., Godycka I., Klos J., Jarule V., Miezeliene A., Alencikiene G. Growth performance, gastrointestinal tractresponses, and meat characteristics of broiler chickens fed a diet containing the naturalalkaloid sanguinarine from Macleaya cordata. J. Appl. Poult. Res. 2010;19:393–400. doi: 10.3382/japr.2009-00114. DOI

Rawling M.D., Merrifield D.L., Davies S.J. Preliminary assessment of dietary supplementation of Sangrovit (R) on red tilapia (Oreochromis niloticus) growth performance and health. Aquaculture. 2009;294:118–122. doi: 10.1016/j.aquaculture.2009.05.005. DOI

Newman S.E., Roll M.J., Harkrader R.J. A naturally occuring compound for controllingpowdery mildew of greenhouse roses. Hort Sci. 1999;34:686–689.

Kosina P., Walterová D., Ulrichová J., Lichnovský V., Stiborová M., Rýdlová H., Vicar J., Krecman V., Brabec M.J., Simánek V. Sanguinarine and chelerythrine: assessment of safety on pigs in ninety days feeding experiment. Food Chem. Toxicol. 2004;42:85–91. doi: 10.1016/j.fct.2003.08.007. PubMed DOI

Deng A.-J., Hai-Lin Q. Cytotoxic dihydrobenzophenanthridine alkaloids from the roots of Macleaya microcarpa. Phytochemistry. 2010;71:816–822. doi: 10.1016/j.phytochem.2010.02.007. PubMed DOI

Feng G., Zhang J., Li X.W., Feng J.T., Zhang X. Insecticidal activity of alkaloids from Macleaya microcarpa against several species of insect pests. Agric. Life Sci. 2008;34(in Chinese with English abstract.):187–192.

Wang G.-X., Zhou Z., Jiang D.-X., Han J., Wang J.-F. In vivo anthelmintic activity of five alkaloids from Macleaya microcarpa. Vet. Parasitol. 2010;171:305–313. doi: 10.1016/j.vetpar.2010.03.032. PubMed DOI

Dostál J., Slavík J. Novější poznatky o sanguinarinu a přbuzných alkaloidech. Chem. Listy. 2000;94:15–20.

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. doi: 10.1016/j.jpba.2007.02.005. PubMed DOI

Slaninová I., Slanina J., Táborská E. Quaternary benzo[c]phenanthridine alkaloids-novel cell permeant and red fluorescing DNA probes. Cytom. Part A. 2007;71A:700–708. doi: 10.1002/cyto.a.20423. PubMed DOI

Zdarilova A., Malikova J., Dvorak Z., Ulrichova J., Šimánek V. Quaternary isoquinoline alkaloids sanguinarine and chelerythrine. In vitro and in vivo effects. Chem. Listy. 2006;100:30–41.

Colombo M.L., Bosisio E. Pharmacological activities of Chelidonium majus L. (Papaveraceae) Pharmacol. Res. 1996;33:127–134. PubMed

Ahmad N., Gupta S., Husain M.M., Heiskanen K.M., Mukhtar H. Differential Antiproliferative and Apoptotic Response of Sanguinarine for Cancer Cells versus Normal Cells. Clin. Cancer Res. 2000;6:1524–1528. PubMed

Barreto M.C., Pinto R.E., Arrabaça J.D., Pavlo M.L. Inhibition of mouse liver respiration by Chelidonium majus isoquinoline alkaloids. Toxicol. Lett. 2003;146:37–47. doi: 10.1016/j.toxlet.2003.09.007. PubMed DOI

Lopus M., Panda D. The benzophenanthridine alkaloid sanguinarine perturbsmicrotubule assembly dynamics through tubulin binding. FEBS J. 2006;273:2139–2150. doi: 10.1111/j.1742-4658.2006.05227.x. PubMed DOI

Kaminskyy V.O., Lootsik M.D., Stoika R.S. 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. Centr. Eur. J. Biol. 2006;1:2–15. doi: 10.2478/s11535-006-0001-y. DOI

Adhami V.M., Aziz M.H., Mukhtar H., Ahmad N. Activation of prodeath Bcl-2 family proteins and mitochondrial apoptosis pathway by sanguinarine in immortalized human HaCaT keratinocytes. Clin. Cancer Res. 2003;9:3176–3182. PubMed

Ishikawa T. Benzo[c]phenanthridine bases and their antituberculosis activity. Med. Res. Rev. 2001;21:61–72. doi: 10.1002/1098-1128(200101)21:1<61::AID-MED2>3.0.CO;2-F. PubMed DOI

Slaninová I., Slunská Z., Sinkora J., Vlková M., Táborská E. Screening of minorbenzo(c)phenanthridine alkaloids for antiproliferative and apoptotic activities. Cell Biol. Toxicol. 2007;45:131–139.

Slaninová I., Táborská, Bochořáková H., Slanina J. Interaction of benzo[c]phenanthridine and protoberberine alkaloids with animal and yeast cells. Cell Biol. Toxicol. 2001;17:51–63. doi: 10.1023/A:1010907231602. PubMed DOI

Urbanová J., Lubal P., Slaninová I., Táborská E., Táborský P. Fluorescence proparties ofselected benzo[c]phenanthridine alkaloids and studies of their interaction with CT DNA. Anal. Bioanal. Chem. 2009;394:997–1002. doi: 10.1007/s00216-009-2601-7. PubMed DOI

Slunská Z., Gelnarová E., Hammerová J., Táborská E., Slaninová I. Effect of quaternarybenzophenanthridine alkaloids sanguilutine and chelilutine on normal and cancer cells. Toxicol. In Vitro. 2010;24:697–706. doi: 10.1016/j.tiv.2010.01.012. PubMed DOI

Zenk M.H. The formation of benzophenanthridine alkaloids. Pure Appl. Chem. 1994;66:2023–2028. doi: 10.1351/pac199466102023. DOI

Abizov E.A., Tolkachev O.N., Kopylova I.E., Luferov A.N. Distribution of the sum of sanguinarine and chelerythrine in the above-ground part of Macleaya microcarpa. Pharm. Chem. J. 2003;37:413–414. doi: 10.1023/A:1027303929278. DOI

Dostál J., Slavik J. Some aspects of the chemistry of quaternary benzo[c]phenanthridine alkaloids. In: Atta-ur-Rahman, editor. Studies in Natural Products Chemistry. Vol. 27. Elsevier Science B.V.; Oxford, UK: 2002. pp. 155–184.

Gregorova J., Babica J., Marek R., Paulova H., Táborská E., Dostal J. Extraction ofisoquinoline alkaloids with butanol and octanol. Fitoterapia. 2010;81:565–568. doi: 10.1016/j.fitote.2010.01.020. PubMed DOI

Influence of Solvent Polarity and DNA-Binding on Spectral Properties of Quaternary Benzo[c]phenanthridine Alkaloids