Podophyllotoxin, a medicinal agent of plant origin: Past, present and future

Chinese Journal of Natural Medicines

Volumn 10, Issue 3, 2012, Pages 161-169

  Guerram, Mounia ^a   Jiang, Zhen Zhou ^a   Zhang, Lu Yong ^a  

^a CHINA PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Antineoplastic; Etoposide; Lignans; Podophyllotoxin; Podophyllum; Teniposide; Tubulin

Indexed keywords

AZATOXIN; ETOPOFOS; ETOPOSIDE; F14512; GL331; NK611; PODOPHYLLOTOXIN; PODOPHYLLOTOXIN DERIVATIVE; TAFLUPOSIDE; TENIPOSIDE; TOP 53; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ANTIVIRAL ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; CONDYLOMA ACUMINATUM; DRUG MECHANISM; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; NONHUMAN; PODOPHYLLUM HEXANDRUM;

EID: 84861476929     PISSN: 20956975     EISSN: 18755364     Source Type: Journal    
DOI: 10.3724/SP.J.1009.2012.00161     Document Type: Article

References (83)

1. Koulman A Podophyllotoxin: A study of the biosynthesis, evolution, function and use of podophyllotoxin and related lignans. Faculty of Mathematics and Natural Sciences [M] 2003, 188. University of Groningen, Groningen. Edition.
2. Jardine I Podophyllotoxins. Anticancer Agents Based on Natural Product Models [M] 1980, Academic Press, New York.
3. Ayres DC, Loike JD Lignans: chemical, biological and clinical properties. Chemistry and Pharmacology of Natural Products [M] 1990, Cambridge University Press, Cambridge.
4. Castro M, Miguel del Corral JM, et al. Chemoinduction of cytotoxic selectivity in podophyllotoxin-related lignans [J]. Phytochemistry Rev 2003, 2:219-233.
5. Canel C, Moraes RM, Dayan FE, et al. Molecules of interest: podophyllotoxin [J]. Phytochemistry 2000, 54(2):115-120.
6. Borsche W, Niemann J über Podophyllin [J]. Justus Liebids Ann Chem 1932, 494:126-142.
7. Arora R Medicinal plant biotechnology [M] 2010, CAB International, Wallingford, United Kingdom.
8. You Y Podophyllotoxin derivatives: current synthetic approaches for new anticancer agents [J]. Curr Pharm Des 2005, 11(13):1695-1717.
9. Srivastava V, Negi AS, Kumar JK, et al. Plant-based anticancer molecules: a chemical and biological profile of some important leads [J]. Bioorg Med Chem 2005, 13(21):5892-5908.
10. Beers SA, Imakura Y, Dai HJ, et al. Antitumor agents, 99. Synthetic ring C aromatized podophyllotoxin analogues as potential inhibitors of human DNA topoisomerase II [J]. J Nat Prod 1988, 51(5):901-905.
11. Liu YQ, Yang L, Zhao YL, et al. Evaluation of insecticidal activity of podophyllotoxin derivatives against Brontispa longissima [J]. Pest Biochem Physiol 2010, 99(1):39-44.
12. Gao R, Gao C, Tian X, et al. Insecticidal activity of deoxypodophyllotoxin, isolated from Juniperus sabina L., and related lignans against larvae of Pieris rapae L. [J]. Pest Manag Sci 2004, 60(11):1131-21136.
13. Damayanthi Y, Lown JW Podophyllotoxins: current status and recent developments [J]. Curr Med chem 1998, 5(3):205-252.
14. Newman DJ, Cragg GM, Snader KM Natural products as sources of new drugs over the period 1981-2002 [J]. J Nat Prod 2003, 66:1022-1037.
15. Feher M, Schmidt JM Property distributions: Differences between drugs, natural products, and molecules from combinatorial chemistry [J]. J Chem Inf Comput Sci 2003, 43:218-227.
16. Giri A, Narasu ML Production of podophyllotoxin from Podophyllum hexandrum: a potential natural product for clinically useful anticancer drugs [J]. Cytotechnology 2000, 34:17-26.
17. Hartwell JL, Schrecker AW Components of podophyllin. V. The constitution of podophyllotoxin [J]. J Am Chem Soc 1951, 73(6):2909-2916.
18. Jackson DE, Dewick PM Aryltetralin lignans from Podophyllum hexandrum and Podophyllum peltatum [J]. Phytochemistry Rev 1984, 23:1147-1152.
19. Chattopadhyay S, Srivastava AK, Bhojwani SS, et al. Production of podophyllotoxin by plant cell cultures of Podophyllum hexandrum in bioreactor [J]. J Biosci Bioenerg 2002, 93:215-220.
20. Weiss SG, Tin-Wa M, Perdue RE, et al. Potential anticancer agents II. Antitumor and cytotoxic lignans from Linum album (Linaceae) [J]. J Pharm Sci 1975, 64:95-98.
21. Konuklugil B Aryltetralin lignans from genus Linum [J]. Fitoterapia 1996, 67:379-381.
22. Koulman A, Bos R, Medarde M, et al. A fast and simple GC-MS method for lignan profiling in Anthriscus sylvestris and biosynthetically related plant species [J]. Planta Med 2001, 67:858-862.
23. Van Uden W, Bos JA, Boeke GM, et al. The large scale isolation of deoxypodophyllotoxin from rhizomes of Anthriscus sylvestris followed by its bioconversion into 5-methoxypodophyllotoxin b-d-glucoside by cell cultures of Linum flavum [J]. J Nat Prod 1997, 60:401-403.
24. Suh SJ, Kim JR, Jin UH, et al. Deoxypodophyllotoxin, flavolignan, from Anthriscus sylvestris Hoffm. inhibits migration and MMP-9 via MAPK pathways in TNF-α-induced HASMC [J]. Vasc Pharmacol 2009, 51:13-20.
25. Jin M, Moon TC, Quan Z, et al. The naturally occurring flavolignan, deoxypodophyllotoxin, inhibits lipopolysaccharide-induced iNOS expression through the NF-κB activation in RAW264.7 macrophage cells [J]. Biol Pharm Bull 2008, 31:1312-1315.
26. Jin M, Lee E, Yang JH, et al. Dual inhibition of cyclooxygenases-2 and 5-lipoxygenase by deoxypodophyllotoxin in mouse bone marrow-derived mast cells [J]. Biol Pharm Bull 2004, 27:786-788.
27. Federolf K, Alfermann AW, Fuss E Aryltetralin-lignan formation in two different cell suspension cultures of Linum album: deoxypodophyllotoxin 6-hydroxylase, a key enzyme for the formation of 6-methoxypodophyllotoxin [J]. Phytochemistry Rev 2007, 68:1397-1406.
28. Kondo K, Ogura M, Midorikawa Y, et al. Conversion of deoxypodophyllotoxin to podophyllotoxin-related compounds by microbes [J]. Agric Biol Chem 1989, 53:777-782.
29. Eyberger AL, Dondapati R, Porter JR Endophyte fungal isolates from Podophyllum peltatum produce podophyllotoxin [J]. J Nat Prod 2006, 69:1121-1124.
30. Kour A, Shawl AS, Rehman S, et al. Isolation and identification of an endophytic strain of Fusarium oxysporum producing podophyllotoxin from Juniperus recurva [J]. World J Microbiol Biotech 2008, 24:1115-1121.
31. Lu W, Fu C, Zhao Y Review on biosynthesis of podophyllotoxin [J]. China J Chin Mater Med 2011, 36(9):1109-1114.
32. Dewick P Biosynthesis of lignans. Studies in Natural Products Chemistry 1989, 5:459-503. Elsevier, Amsterdam. Atta-ur-Rahman (Ed.).
33. Gordaliza M, Garcia PA, Del Corral JMM, et al. Podophyllotoxin: distribution, sources, applications and new cytotoxic derivatives [J]. Toxicon 2004, 44(4):441-459.
34. Loike J, Brewer CF, Sternlicht H, et al. Structure-activity study of the inhibition of microtubule assembly in vitro by podophyllotoxin and its congeners [J]. Cancer Res 1978, 38:2688-2693.
35. Wigley DB Structure and mechanism of DNA topoisomerases. [J]. Annu Rev Biophys Biomol Struct 1995, 24:185-208.
36. Gordaliza M, Castro MA, Del Corral JM, et al. Antitumor properties of podophyllotoxin and related compounds [J]. Curr Pharm Des 2000, 6:1811-1839.
37. Fleming RA, Miller AA, Steward CF Etoposide: an update [J]. Clin Pharm 1989, 8:274-293.
38. Saitoha T, Kuramochib K, Imaia T, et al. Podophyllotoxin directly binds a hinge domain in E2 of HPV and inhibits an E2/E7 interaction in vitro [J]. Bioorg Med Chem 2008, 16(10):5815-5825.
39. Gordaliza M, Miguel del Corral JM, Castro MA, et al. Cytotoxic cyclolignans related to podophyllotoxin [J]. II Farmaco 2001, 56:297-304.
40. Kelly MG, Hartwell JL The biological effects and chemical composition of podophyllin [J]. J Natl Cancer Inst 1954, 14:967-1010.
41. O'Dwyer PJ, Leyland-Jones B, Alonso MT, et al. Etoposide (VP-16-213). Current status of an active anticancer drug [J]. N Engl J Med 1985, 312(11):692-700.
42. Hainsworth JD, Greco FA Etoposide: twenty years later [J]. Ann Oncol 1995, 6:325-341.
43. Horwitz SB, Loike JD A comparison of the mechanism of action of VP-16-213 and podophyllotoxin [J]. J Nat Prod 1977, 40:82-89.
44. Desbène S, Giorgi-Renault S Drugs that inhibit tubulin polymerization: The particular case of podophyllotoxin and analogues [J]. Curr Med Chem 2002, 2:71-90.
45. Wang JC DNA topoisomerases [J]. Annu Rev Biochem 1996, 65:635-692.
46. Smith MA, Rubinstein L, Cazenave L, et al. Binding of etoposide to topoisomerase II in the absence of DNA [J]. J Natl Cancer Inst 1993, 85:554-558.
47. Schacter L Etoposide phosphate: what, why, where, and how? [J]. Semin Oncol Nurs 1996, 23(6 Suppl 13):1-7.
48. Hainsworth JD, Williams SD, Einhorn LH, et al. Successful treatment of resistant germinal neoplasms with VP-16 and cisplatin: results of a southeastern cancer study group trial [J]. J Clin Oncol 1985, 3:666-671.
49. Van Maanen JM, Retel J, De Vries J, et al. Mechanism of action of antitumor drug etoposide: a review [J]. J Natl Cancer Inst 1988, 80:1526-1533.
50. Shah JC, Chen JR, Chow D Preformulation study of etoposide: identification of physicochemical characteristics responsible for the low and erratic oral bioavailability of etoposide [J]. Pharm Res 1989, 6:408-412.
51. Imbert TF Discovery of podophyllotoxins [J]. Biochimie 1998, 80:207-222.
52. Hande KR Etoposide: Four decades of development of a topoisomerase II inhibitor [J]. Eur J Cancer 1998, 34:1514-1521.
53. Bohlin L, Rosen B Podophyllotoxin derivatives: Drug discovery and development [J]. Drug Discov Today 1996, 1:343-351.
54. Liu YQ, Yang L, Tian X Podophyllotoxin: current perspectives [J]. Curr Bioactive Comp 2007, 3:37-66.
55. Rassmann I, Thödtmann R, Mross M, et al. Phase I clinical and pharmacokinetic trial of the podophyllotoxin derivative NK611 administered as intravenous short infusion [J]. Invest New Drugs 1998-1999, 16(4):319-324.
56. Pagani O, Zucchetti M, Sessa C, et al. Clinical and pharmacokinetic study of oral NK611, a new podophyllotoxin derivatives [J]. Cancer Chemother Pharmacol 1996, 38:541-547.
57. Kamala A, Suresh P, Mallareddy A, et al. Synthesis of a new 4-aza-2,3-didehydropodophyllotoxin analogues as potent cytotoxic and antimitotic agents [J]. Bioorg Med Chem 2011, 19:2349-2358.
58. Chen Y, Su HY, Wang HC, et al. Induction of apoptosis and cell cycle arrest in glioma cells by GL331 (a topoisomerase II inhibitor) [J]. Anticancer Res 2005, 25(6B):4203-4208.
59. Huang ST, Shu HC, Lee CC, et al. In vitro evaluation of GL331's cancer cell killing and apoptosis- inducing activity in combination with other chemotherapeutic agents [J]. Apoptosis 2000, 5:79-85.
60. Huang ST, Lee CC, Chao Y, et al. A novel podophyllotoxin- derived compound GL331 is more potent than its congener VP-16 in killing refractory cancer cells [J]. Pharm Res 1999, 16:997-1002.
61. Lee KH Discovery and development of natural product- derived chemotherapeutic agents based on a medicinal chemistry approach [J]. J Nat Prod 2010, 73(3):500-516.
62. Cline SD, Macdonald TL, Osheroff N Azatoxin is a mechanistic hybrid of the topoisomerase II-targeted anticancer drugs etoposide and ellipticine [J]. Biochemistry 1997, 36:13095-13101.
63. Solary E, Leteurtre F, Paull KD, et al. Dual inhibition of topoisomerase II and tubulin polymerization by azatoxin, a novel cytotoxic agent [J]. Biochem Pharmacol 1993, 45(12):2449-2456.
64. Terada T, Fujimoto K, Nomura MA, et al. Antitumor agents. 3. Synthesis and biological activity of 4β-alky1 derivatives containing hydroxy, amino, and amido groups of 4'-O-demethyl-4-desoxypodophyllotoxin as antitumor agents [J]. J Med Chem 1993, 36(12):1689-1699.
65. Yoshida M, Kobunai T, Aoyagi K, et al. Specific distribution of TOP-53 to the lung and lung-localized tumor is determined by its interaction with phospholipids [J]. Clin Cancer Res 2000, 6(11):4396-4401.
66. Cragg GM, Newman DJ A tale of two tumour targets: topoisomerase I and tubulin. The wall and wani contribution to cancer chemotherapy [J]. J Nat Prod 2004, 67:232-244.
67. Barret JM, Kruczynski A, Vispé S, et al. F14512, a potent antitumor agent targeting topoisomerase II vectored into cancer cells via the polyamine transport system [J]. Cancer Res 2008, 68:9845-9853.
68. Kruczynski A, Vandenberghe I, Pillon A, et al. Preclinical activity of F14512, designed to target tumors expressing an active polyamine transport system [J]. Invest New Drugs 2011, 29:9-21.
69. Long BH, Musial ST, Brattain MG Comparison of cytotoxicity and DNA breakage activity of congeners of podophyllotoxin including VP16-213 and VM26: a quantitative structure-activity relationship [J]. Biochemistry 1984, 23:1183-1188.
70. Markkanen T, Mäkinen ML, Maunuksela E, et al. Podophyllotoxin lignans under experimental antiviral research [J]. Drugs Exptl Clin Res 1981, 7:711-718.
71. Chatterjee A, Prakashi SC The treatise on indian medicinal plants [M] 1995, Publication & Information Directorate, CSIR Publication, New Delhi.
72. Goel HC, Prasad J, Sharma A Antitumor and radioprotective action of Podophyllum hexandrum [J]. Indian J Exp Biol 1998, 36:583-587.
73. Arora R, Gupta D, Chawla R, et al. Radioprotection by plant products: present status and future prospects [J]. Phytother Res 2005, 19:1-22.
74. Frega A, Stentella P, DiRenzi F, et al. Assessment of self application of four topical agents on genital warts in women [J]. J Eur Acad Dermatol Venereol 1997, 8:112-115.
75. Gross G Clinical diagnosis and management of anogenital warts and papillomavirus-associated lesions [J]. Hautarzt 2001, 52:6-17.
76. Von Krogh G, Lacey CJ, Gross G, et al. European course on HPV associated pathology: guidelines for primary care physicians for the diagnosis and management of anogenital warts [J]. Sex Transm Infect 2000, 76:162-168.
77. Wiley D, Douglas J, Beutner K, et al. External genital warts: diagnosis, treatment, and prevention [J]. Clin Infect Dis 2002, 35:S210-S224.
78. Syed TA, Cheema KM, Khayyami M, et al. Human leukocyte interferon-a versus podophyllotoxin in cream for the treatment of genital warts in males. A placebo-controlled, double-blind, comparative study [J]. Dermatology 1995, 191:129-132.
79. Wilson J Treatment of genital warts-what's the evidence? [J]. Int J STD AIDS 2002, 13:216-222.
80. Schwartz J, Norton SA Useful plants of dermatology. VI. The mayapple (Podophyllum) [J]. J Am Acad Dermatol 2002, 47:774-775.
81. Subrahmanyam D, Renuka B, Rao CV, et al. Novel D-ring analogues of podophyllotoxin as potent anti-cancer agents [J]. Bioorg Med Chem Lett 1998, 8:1391-1396.
82. Pugh NI, Khan I, Moraes RM, et al. Podophyllotoxin lignans enhance IL-1E but suppress TNF-a mRNA expression in LPS-treated monocytes. Immunopharmacol [J]. Immunotoxicol 2001, 23:83-95.
83. Botta B, Monache GD, Misiti D, et al. Aryltetralin lignans: chemistry, pharmacology and biotrans-formations [J]. Curr Med Chem 2001, 8:1363-1381.