Anticancer lignans-from discovery to biotechnology

Mini-Reviews in Medicinal Chemistry

Volumn 11, Issue 10, 2011, Pages 843-856

  Ionkova, I ^a  

^a MEDICAL UNIVERSITY OF SOFIA   (Bulgaria)

Author keywords

Anticancer aryltetralin and arylnaphthalene lignans; Biotechnology; In vitro production; Linum; Podophillum; Podophyllotoxin and derivatives

Indexed keywords

2,3 DIHYDRO 2 (4 HYDROXY 3 METOXYPHENYL) 3 HYDROXYMETHYL 5 (OMEGA HYDROXYPROPYL) 7 MTOXYBENZOFURAN; 4' DEMETHYLLPODOPHYLLOTOXIN; 6 METHOXYPODOPHYLLOTOXIN; ALPHA PELTATIN; ANTINEOPLASTIC AGENT; ARCTIGENIN; ARYLNAPHTHALENE LIGNAN; ARYLTETRALIN LIGNAN; BETA PELTATIN; CONIFERIN; DIPROPHYLLINE; EPIPINORESINOL; EPIPODOPHYLLOTOXIN; ETOPOFOS; ETOPOSIDE; ISOJUSTICIDIN B; ISOLARICIRESINOL; JUSTICIDIN B; LARICIRESINOL; LIGNAN; MATAIRESINOL; PHILLYRIN; PINORESINOL; PODOPHYLLOTOXIN; POSALFILIN; SECOISOLARICIRESINOL; TENIPOSIDE; TRACHELOGENIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; WIKSTROMOL;

ANGIOSPERM; ANTINEOPLASTIC ACTIVITY; ARTICLE; BERBERIDACEAE; CARBON NUCLEAR MAGNETIC RESONANCE; CONDYLOMA ACUMINATUM; DRUG ISOLATION; DRUG MANUFACTURE; DRUG STRUCTURE; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR MULTIPLE QUANTUM COHERENCE; HUMAN; HYDROXYLATION; HYPTIS; IN VITRO STUDY; JUNIPERUS; LEUKEMIA; LUNG CANCER; MICROTUBULE ASSEMBLY; PLANT BIOTECHNOLOGY; PLANT CELL; RHEUMATOID ARTHRITIS; TESTIS CANCER;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BIOTECHNOLOGY; CELL SURVIVAL; HUMANS; LIGNANS; PLANT CELLS; PODOPHYLLOTOXIN;

EID: 79960996154     PISSN: 13895575     EISSN: 18755607     Source Type: Journal    
DOI: 10.2174/138955711796575425     Document Type: Article

References (49)

1. Raskin, I. Plants and pharmaceuticals in the 21st century. In: Proceedings of the 10th IAPTC&B Congress-Plant Biotechnology 2002 and Beyond., I. Vassil (ed.) Kluwer Academic Publishers, Dordrecht, Boston, London pp. 83-95, 2002.
2. Dechamp, J. Herbal medicinal products and patents need in Europe. Drug Inf. J., 1999, 33, 309-313.
3. Wink, M.; Alfermann, W.; Franke, R.; Wetterauer, B.; Distl, M.; Windhövel, J.; Krohn, O.; Fuss, E.; Garden, H.; Mohagheghzadeh, A.; Wildi, E.; Ripplinger, P. Sustainable bioproduction of phytochemicals by plant in vitro cultures: anticancer agents. Plant Gen. Resources, 2005, 3, 90-100.
4. Ionkova, I. Anticancer compounds from in vitro cultures of rare medicinal plants. Pharmacogn. Rev., 2009, 2(4), 206-218.
5. Moss, G. P. Nomenclature of lignans and neolignans (IUPAC Recommendations 2000). Pure Appl. Chem., 2000, 72, 1493-1523.
6. Van Uden, W.; Pras, N.; Malingré, T.M. On the improvement of podophyllotoxin production by phenylpropanoid precursor feeding to cell cultures of Podophyllum hexandrum Royle. Plant Cell Tiss. Org. Cult., 1990, 23, 217-224.
7. Ionkova, I. Biotechnological approaches for the production of lignans. Phcog. Rev., 2007, 1, 57-68.
8. Vasilev, N.; Ionkova, I. Isolation and structure Elucidation of Aryltetralin Lignans from Linum tauricum ssp. Bulgaricum. Pharmacogn. Mag., 2006, 2(7), 169-174.
9. Konuklugil, B.; Ionkova, I.; Vasilev, N.; Schmidt, T.; Windhövec, J.; Fuss, E.; Alfermann, A. Lignans from Linum species of sections Syllinum and Linum. Nat. Prod. Res., 2007, 21, 1-6.
10. Ionkova, I. Biotechnology and modern production of plant made pharmaceuticals: anticancer compounds. Int. J. Curr. Chem., 2010, 1(4), 199-209.
11. Kour, A.; Shawl, A. S.; Rehman, S.; Sultan, P.; Qazi, P. H.; Suden, P.; Khajuria, R. K.; Verma, V. Isolation and identification of an endophytic strain of Fusarium oxysporum producing podophyllotoxin from Juniperus recurva. World J. Microbiol. Biotechnol., 2008, 24, 1115-1121.
12. Vasilev, N.; Ebel, R.; Edrada, R.A.; Fuss, E.; Alfermann, A.W.; Ionkova, I.; Petrova, A.; Repplinger, M.; Schmidt, T.J. Metabolic profiling of lignan variability in Linum species of section Syllinum native to Bulgaria. Planta Med. 2008, 74, 273-280.
13. Vasilev, N.; Momekov, G.; Zaharieva, M.; Konstantinov, S.; Bremner, P.; Heinrich, M.; Ionkova, I. Cytotoxic activity of podophyllotoxin-like lignan from Linum tauricum Willd. Neoplasma, 2005, 52, 425-429.
14. Schmidt, T. J.; Hemmati, S.; Fuss, E.; Alfermann, A. W. A combined HPLC-UV and HPLC-MS method fort he identification of lignans and ist application to the lignans of Linum usitatissimum L. and L. bienne Mill. Phytochem. Anal., 2006, 17, 299-311.
15. Fuss, E. Lignans in plant cell and organ cultures: An overview. Phytochem. Rev., 2003, 2(3), 307-320.
16. Gu, Z-M.; Zhou, D.; Lewis, N.J.; Wu, J.; Johnson, H.A.; McLaughlin, J.L.; Gordon, J. Quantitative evaluation of annonaceous acetogenins in monthly samples of paw paw (Asimina triloba) twigs by liquid chromatography/electrospray ionization/tandem mass spectrometry. Phytochem. Anal., 1999, 10, 32-38.
17. Canel, C.; Moraes, R. M.; Dayan, F. E.; Ferreira, D. Molecules of interest 'Podophyllotoxin'. Phytochemistry, 2000, 54, 115-120.
18. Hadimani, S. B.; Tanpure, R. P.; Bhat S.V. Asymetric total synthesis of podophyllotoxin. Tetrahedron Lett. 1996, 27, 4791-4794.
19. Medarde, M.; Ramos, A. C.; Caballero, E.; Lopez, J. L.; Lamamié de Clairac, R. P.; San Feliciano, A. A new approach to the synthesis of podophyllotoxin based on epimerization reactions. Tetrahedron Lett., 1996, 15, 2663-2666.
20. Canel, C.; Dayan, F. E.; Ganzera, M.; Khan, I. A.; Rimando, A.; Burandt, C. L.; Moraes, R. M. High yield of podophyllotoxin from leaves of Podophyllum peltatum by in situ conversion of podophyllotoxin 4-O-β-D-glucopyranoside. Planta Med., 2001, 67,
21. 9E7m-p9t9,.U.; Alfermann, A.W.; Pras, N.; Petersen, M. The use of plant cell cultures for the production of podophyllotoxin and related lignans. J. Appl. Bot., 2000, 74, 145-150.
22. Mohagheghzadeh, A.; Schmidt, T.J.; Alfermann, A.W. Arylnaphthalene lignans from in vitro cultures of Linum austriacum. J. Nat. Prod., 2002, 65, 69-71.
23. Vasilev, N.; Ionkova I. Lignan production by cell cultures of Linum setaceum and Linum campanulatum. Pharm. Biol., 2005, 43(6), 509-511.
24. Vasilev, N.; Ionkova, I. Cytotoxic activity of extracts from Linum cell cultures. Fitoterapia, 2005, 76, 50-53.
25. Mohagheghzadeh, A.; Dehshahri, S.; Hemmati, S. Accumulation of lignans by in vitro cultures of three Linum species. Z. Naturforsch., 2009, 64c, 73-76.
26. Schmidt, T.J.; Vößing, S.; Klaes, M., Grimme, S. An aryldihydronaphthalene lignan with a novel type of ring system and further new lignans from Linum perenne L. Planta Med., 2007, 73, 1574-1580.
27. Schmidt, T.S.; Hemmati, M.; Klaes, B.; Konuklugil, A.; Mohagheghzadeh, I.; Ionkova, E.; Fuss, A.W. Alfermann, (2010), Lignans in Linum species - Chemodiversity in the light of systematics and phylogeny. Phytochemistry, 2010, 71(14-15), 1714-28.
28. Kelly, M.G.; Hartwell, J. L. The biological effects and the chemical composition of podophyllin: a review. J. Natl. Cancer Inst., 1954, 14, 967-1010.
29. Cockayne, T.O., Leech book of Bald, in: Leechdom, Wortcunnings and Starcraft of Early England (T.O. Cockayne ed.) The Holland Press, London, 1961.
30. Ayres, D. C. and Loike, J. D., Lignans, chemical, biological and clinical properties, Cambridge University Press, Oxford, 1990.
31. Tu, G. (ed.), Pharmacopoeia of the Peoples Republic of China, Beijing, Guangdong Science and Technology Press Vol.1, 1977.
32. Moraes, R.M.; Hemant, L.; Ebru, B.; Muhammad, M.; Cushman, K. The American Mayapple and its Potential for Podophyllotoxin Production, In: Trends in new crops and new uses. J. Janick and A. Whipkey (eds.). ASHS Press, Alexandria, VA, 2002.
33. Imbert, F. Discovery of podophyllotoxins, Biochimie, 1998, 80, 207-222.
34. Xu, H.; Lv, M.; Tian, X. A review on hemisynthesis, biosynthesis, biological activities, mode of action and structure activity relationship of podophyllotoxin: 2003-2007. Curr. Med. Chem., 2009, 16, 327-349.
35. Hande, K. R. Topoisomerase II inhibitors. Update Can. Therap., 2008, 3, 13-26.
36. Vasilev, N.; Elfahmi Boss, R.; Kaiser, O.; Momekov, G.; Konstantinov, S.; Ionkova, I. Production of Justicidine B, a Cytotoxic Arylnaphthalene Lignan from Genetically Transformed Root Cultures of Linum leonii. J. Nat. Prod., 2006, 69(7), 1014-1017.
37. Lautié, E.; Fliniaux, M.; Villarreal, M. Updated biotechnological approaches developed for 2,7'-cyclolignan production. Biotechnol. Appl. Biochem., 2010, 55(3), 139-153.
38. Yousefzadi, M.; Sharifi, M.; Behmanesh, M.; Moyano, E.; Bonfill, M.; Cusido, R.; Palazon, J. Podophyllotoxin: Current approaches to its biotechnological production and future challenges. Eng. Life Sci., 2010, 10(4), 281-292.
39. Ionkova, I. Podophyllotpxin and related lignans: Biotechnological Production by in vitro plant cell cultuers, In: Medicinal plant biotechnology, (Editor: Rajesh Arora), CABI Publishing, Wallingford, Oxon, United Kingdom, 2010, Chapter 9, 138-155.
40. Kuhlmann, S.; Kranz, K.; Lücking, B.; Alfermann, A.W.; Petersen, M. Aspects of cytotoxic lignan biosynthesis in suspension cultures of Linum nodiflorum. Phytochem. Rev., 2002, 1, 37-43.
41. Ionkova, I.; Antonova, I.; Momekov, G.; Fuss, E. Production of podophyllotoxin in Linum linearifolium in vitro cultures. Pharmacogn. Mag., 2010, 6(23), 180-185.
42. Ionkova, I.; Fuss, E. Influence of different strains of Agrobacterium rhizogenes on induction of hairy roots and lignan production in Linum tauricum ssp. Tauricum. Pharmacogn. Mag., 2009, 4(17), 14-18.
43. Ionkova, I. Effect of methyl jasmonate on production of ariltetralin lignans in hairy root cultures of Linum tauricum. Pharmacogn. Res., 2009, 2(2), 102-105.
44. Schmitt, J.; Petersen, M. Influence of methyl jasmonate and conyferyl alcohol on pinoresinol and matairesinol accumulation in a Forsythia x intermedia cell suspension culture. Plant Cell Report, 2002, 20, 885-889.
45. Kamal, A.; Damayanthi, Y. A novel enzymatic dehydrogenation of podophyllotoxin congeners by yeast cells. Bioorg. Med. Chem. Lett., 1997, 7(6), 657-662.
46. Vasilev, N.; Julsing, M.; Koulman, A.; Clarkson, C.; Woenderbag, H.; Ionkova, I.; Boss, R.; Jaroszewski, J.; Kaiser, O. Bioconversion of deoxypodophyllotoxin into epipodophyllotoxin in E. coli using human cytochrome P450 3A4. J. Biotechnol., 2006, 126, 383-393.
47. Chattopadhyay, S.; Bisaria, V. S.; Bhojwani, S. S.; Srivastava, A. K. Enhanced production of podophyllotoxin by Podophyllum hexandrum using in situ cell retention bioreactor. Biotechnol. Prog., 2003, 19, 1026-1028.
48. Garden H. Biotechnological production of podophyllotoxin by Linum album suspension cultures, Doctoral Thesis, Heinrich-Heine Universität, Düsseldorf, 2003.
49. Georgiev, M.I.; Pavlov, A.I.; Bley, T. Hairy root type plant in vitro systems as sources of bioactive substances. Appl. Microbiol. Biotechnol., 2007, 74(6), 1175-1185.