Study of cytotoxic activity, podophyllotoxin, and deoxypodophyllotoxin content in selected Juniperus species cultivated in Poland

Pharmaceutical Biology

Volumn 53, Issue 6, 2015, Pages 831-837

  Och, Marek ^a   Och, Anna ^a   Cies̈la, Łukasz ^a   Kubrak, Tomasz ^a   Pecio, Łukasz ^b   Stochmal, Anna ^b   Kocki, Janusz ^a   Bogucka Kocka, Anna ^a  

^a MEDICAL UNIVERSITY OF LUBLIN   (Poland)

^b STATE RESEARCH INSTITUTE   (Poland)

Author keywords

Antitumor lignans; Cupressaceae; Leukemia cell lines; UPLC

Indexed keywords

DEOXYPODOPHYLLOTOXIN; JUNIPERUS COMMUNIS EXTRACT; JUNIPERUS SCOPULORUM EXTRACT; PLANT EXTRACT; PODOPHYLLOTOXIN; UNCLASSIFIED DRUG; ANTINEOPLASTIC AGENT; COLORING AGENT; TRYPAN BLUE;

ARTICLE; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; HUMAN; HUMAN CELL; IC50; IN VITRO STUDY; JUNIPERUS; JUNIPERUS CHINENSIS; JUNIPERUS CONFERTA; JUNIPERUS DAVURICA; JUNIPERUS DEPRESSA; JUNIPERUS HORIZONTALIS; JUNIPERUS SABINA; JUNIPERUS SCOPULORUM; JUNIPERUS SQUAMATA; JUNIPERUS VIRGINIANA; JUNIPERUS X MEDIA; LEUKEMIA CELL LINE; NONHUMAN; PLANT LEAF; POLAND; SPECIES CULTIVATION; TRYPAN BLUE ASSAY; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY; ANALOGS AND DERIVATIVES; CELL SURVIVAL; CHEMISTRY; DRUG EFFECTS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LEUKEMIA; TUMOR CELL LINE;

BERBERIDACEAE; CUPRESSACEAE; JUNIPERUS; JUNIPERUS COMMUNIS; JUNIPERUS DAVURICA; JUNIPERUS SCOPULORUM; SINOPODOPHYLLUM HEXANDRUM;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; CELL SURVIVAL; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COLORING AGENTS; HUMANS; JUNIPERUS; LEUKEMIA; PLANT LEAVES; PODOPHYLLOTOXIN; POLAND; TRYPAN BLUE;

EID: 84944443364     PISSN: 13880209     EISSN: 17445116     Source Type: Journal    
DOI: 10.3109/13880209.2014.943246     Document Type: Article

References (32)

1. Adams RP. (2011). Juniperus of the World: The Genus Juniperus. Bloomington: Trafford Publishing Co.
2. Avula B, Wang YH, Moraes RM, Khan IA. (2011). Rapid analysis of lignans from leaves of Podophyllum peltatum L. samples using UPLCUV-MS. Biomed Chromatogr 25:1230-6.
3. Ayres DC, Loike JD. (1990). Chemistry and Pharmacology of Natural Products. Lignans. Chemical, Biological and Clinical Properties. Cambridge: University Press.
4. Bogucka-Kocka A, Smolarz HD, Kocki J. (2008). Apoptotic activities of ethanol extracts from some Apiaceae on human leukaemia cell lines. Fitoterapia 79:487-97.
5. Cairnes DA, Ekundayo O, Kingston DGI. (1980). Plant anticancer agents X. Lignans from Juniperus phoenicea. J Nat Prod 43:495-7.
6. Canel C, Moraes RM, Dayan FE, Ferreira D. (2000). Podophyllotoxin. Phytochemistry 54:115-20.
7. Cantrell LC, Zheljazkov VD, Osbrink WLA, et al. (2013). Podophyllotoxin and essential oil profile of Juniperus and related species. Ind Crop Prod 43:668-76.
8. Chia-Jen T, Ying-Jan W, Yu-Chih L, et al. (2002). Microtubule damaging agents induce apoptosis in HL-60 cells and G2/M cell cycle arrest in HT 29 cells. Toxicology 175:123-42.
9. CITES. Convention on International Trade in Endangered Species of Wild Fauna and Flora. Washington. Available from: http://www.cites. org/eng/app/appendices.php [last accessed 5 Jun 2014].
10. Cushman KE, Maqbool M, Gerard PD, et al. (2003). Variation of podophyllotoxin in leaves of Eastern red cedar (Juniperus virginiana L.). Planta Med 69:477-8.
11. Gawde AJ, Zheljazkov VD, Maddox V, Cantrell CL. (2009). Bioprospection of Eastern red cedar from nine physiographic regions in Mississippi. Ind Crop Prod 30:59-64.
12. Gordaliza M, Garcia PA, Miguel del Corral JM, et al. (2004). Podophyllotoxin: Distribution, sources, applications and new cytotoxic derivatives. Toxicon 44:441-59.
13. Hartwell JL, Johnson JM, Fitzgerald DB, Belkin M. (1953). Podophyllotoxin from Juniperus species; savinin. J Am Chem Soc 75:235-6.
14. Holthius JJM. (1988). Etoposideandteniposide: Bioanalysis, metabolism and clinical pharmokinetics. Pharmaceutisch Weekblad 10:101-16.
15. ICH Harmonised Tripartite Guideline. Validation of Analytical Procedures: Text and Methodology, Q2 (R1), Geneva, 2005. http://www.ich.org/fileadmin/Public-Web-Site/ ICH-Products/Guidelines/Quality/Q2-R1/Step4/Q2-R1-Guideline. pdf [last accessed 7 Jan 2014].
16. Ikeda R, Nagao T, Okabe H, et al. (1998). Antiproliferative constituents in Umbellifereae plants. III. Constituents in the root and the ground part of Anthriscus sylvestris Hoffm. Chem Pharm Bull (Tokyo) 46: 871-4.
17. Imbert TF. (1998). Discovery of podophyllotoxins. Biochimie 80: 207-22.
18. Julsing MK, Vasilev NP, Schneidman-Duhovny D, et al. (2008). Metabolic stereoselectivity of cytochrome P450 3A4 towards deoxypodophyllotoxin: In silico predictions and experimental validation. Eur J Med Chem 43:1171-9.
19. Kim Y, Kim SB, You YJ, Ahn BZ. (2002). Deoxypodophyllotoxin; The cytotoxic and antiangiogenic component from Pulsatillakoreana. Planta Med 68:271-4.
20. Koulman A. (2003). Podophyllotoxin: A Study of the Biosynthesis, Evolution, Function and Use of Podophyllotoxin and Related Lignans. Doctoral thesis. Rijksuniversiteit Groningen, Netherlands. Available from: http://irs.ub.rug.nl/ppn/252657888 [last accessed 7 Jan 2014].
21. Kusari S, Zühlke S, Spiteller M. (2011). Chemometric evaluation of the anti-cancer pro-drug podophyllotoxin and potential therapeutic analogues in Juniperus and Podophyllum species. Phytochem Anal 22: 128-43.
22. Majumder A, Jha S. (2009). Biotechnological approaches for the production of potential anticancer leads podophyllotoxin and paclitaxel: An overview. J Biol Sci 1:46-69.
23. Masuda T, Oyama Y, Yonemori S, et al. (2002). Flow cytometric estimation on cytotoxic activity of leaf extracts from seashore plants in subtropical Japan: Isolation, quantification and cytotoxic action of deoxypodophyllotoxin. Phytother Res 16:353-8.
24. Muranaka T, Miyata M, Ito K, Tachibana S. (1998). Production of podophyllotoxin in Juniperus chinensis callus cultures treated with oligosaccharides and a biogenetic precursor. Phytochemistry 49: 491-6.
25. Muto N, Tomokuni T, Haramoto M, et al. (2008). Isolation of apoptosis and differentiation-inducing substances to ward human promyelocytic leukemia HL-60 cells from leaves of Juniperus taxifolia. Biosci Biotechnol Biochem 72:477-84.
26. Neung-Ju L, In-Cheol J, Moo-Youn C, et al. (2006). Synthesis and in vitro antitumor activity of phthalimide polymers containing podophyllotoxin. Eur Polym J 42:3352-9.
27. Renouard S, Lopez T, Hendrawati O, et al. (2011). Podophyllotoxin and deoxypodophyllotoxin in Juniperus bermudiana and 12 other Juniperus species: Optimization of extraction, method validation, and quantification. J Agric Food Chem 59:8101-7.
28. Stahelin HF, Wartburg AV. (1991). The chemical and biological route from podophyllotoxin glucoside to etoposide. Cancer Res 51:5-15.
29. Vasilev NP, Julsing MK, Koulman A, et al. (2006). Bioconversion of deoxypodophyllotoxin into epipodophyllotoxin in E. coli using human cytochrome P450 3A4. J Biotechnol 126:383-93.
30. Xu P, Sun Q, Wang X, et al. (2010). Pharmacological effect of deoxypodophyllotoxin: A medicinal agent of plant origin, on mammalian neurons. Neurotoxicology 31:680-6.
31. Yousefzadi M, Sharifi M, Behmanesh M, et al. (2010). Podophyllotoxin: Current approaches to its biotechnological production and future challenges. Eng Life Sci 10:281-92.
32. Zheljazkov VD, Cantrell CL, Donega MA, Astatkie T. (2013). Bioprospecting for podophyllotoxin in the Big Horn Mountains, Wyoming. Ind Crop Prod 43:787-90.