CN: 32-1845/R
ISSN: 2095-6975
引用本文:
0
GUERRAM Mounia, 江振洲, 张陆勇. 天然来源的鬼臼毒素研究进展[J]. 中国天然药物英文, 2012, 10(3): 161-169

天然来源的鬼臼毒素研究进展

GUERRAM Mounia1, 江振洲1,2, 张陆勇1,3
1 中国药科大学江苏省新药筛选中心, 南京 210009;
2 中国药科大学药物质量与安全预警教育部重点实验室, 南京 210009;
3 中国药科大学江苏省药效研究与评价服务中心, 南京 210009
摘要:
芳基萘满木脂素鬼臼毒素,是从不同鬼臼属植物根茎中提取的树脂中的主要成分,具有显著的抗肿瘤和抗病毒活性,自古以来被多个国家广泛用于相关疾病的治疗。目前,鬼臼毒素主要作为细胞毒类药物合成的母体结构而受到广泛关注。例如依托泊苷和替尼泊苷,这些药物常与其他药物合并使用治疗一系列肿瘤疾病。本文对鬼臼毒素予以综述,对其结构特征、药用来源、生物活性、衍生物和应用方面进行了总结。
关键词:    鬼臼毒素    抗肿瘤活性    微管蛋白    依托泊苷    替尼泊苷   
收稿日期: 2012-03-30
JIANG Zhen-Zhou: Assitant Prof., Tel: 86-25-83271043, E-mail: jiangcpu@yahoo.com.cn; ZHANG Lu-Yong: Prof., Tel: 86-25-83271500, E-mail: lyzhangchina@hotmail.com
相关功能
PDF(426 KB) Free
打印本文
把本文推荐给朋友
作者相关文章
GUERRAM Mounia 在本刊中的所有文章
江振洲 在本刊中的所有文章
张陆勇 在本刊中的所有文章
参考文献:
[1] Koulman A. Podophyllotoxin:A study of the biosynthesis, evolution, function and use of podophyllotoxin and related lignans. In:Faculty of Mathematics and Natural Sciences[M]. Edition Groningen:University of Groningen, 2003:188.
[2] Jardine I. Podophyllotoxins. In:Anticancer Agents Based on Natural Product Models[M]. New York:Academic Press, 1980.
[3] Ayres DC, Loike JD. Lignans:chemical, biological and clinical properties. In:Chemistry and Pharmacology of Natural Products[M]. Cambridge:Cambridge University Press, 1990.
[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]. Wallingford, United Kingdom:CAB International, 2010.
[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 fl avolignan, deoxypodophyllotoxin, inhibits lipopolysaccharide-induced iNOS expression through the NF-КB 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[M]. In:Studies in Natural Products Chemistry (ed. Atta-ur-Rahman). Amsterdam:Elsevier, 1989, 5:459-503.
[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 podophyllotoxinderived 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 productderived 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]. Publication & Information Directorate, New Delhi:CSIR Publication, 1995.
[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.