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Camptotheca acuminata Decne

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Chinese Drugs of Plant Origin

Abstract

Camptotheca acuminata Decne (Nyssaceae) is a tree native to and widely distrubuted in the southern part of China. The alkaloid component, camptotheein, with a new structural feature and an antileukemic activity, was isolated by Wall et al. in 1966 [1]. Since then, the chemical and biological properties of camptothecin and related alkaloids isolated from C. acuminata or synthesized have been investigated in great detail [2–5].

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References

  1. Wall ME, Wani MC, Cook CE, Palmer KH, McPhail AT, Sim GA (1966) Plant antitumor agents. I. The isolation and structure of camptothecin, a novel alkaloidal leukemia and tumor inhibitor from Camptotheca acuminata. J Am Chem Soc 88:3888–3890

    Article  CAS  Google Scholar 

  2. Wall ME, Wani MC (1980) Camptothecin. In: Cassady JM, Douros JD (eds) Anticancer Agents Based on Natural Product Models. Academic, New York, pp. 417–436

    Google Scholar 

  3. Cai JC, Hutchinson CR (1983) Camptothecin. Chem Heterocycl Comp 25:753–781

    Article  CAS  Google Scholar 

  4. Schultz AG (1973) Camptothecin. Chem Rev 73:385–405

    Article  PubMed  CAS  Google Scholar 

  5. Hutchinson CR (1981) Camptothecin: chemistry, biogenesis and medicinal chemistry. Tetrahedron 37:1047–1065

    Article  CAS  Google Scholar 

  6. McPhail AT, Sim GA (1969) The structure of camptothecin. X-ray analysis of camptothecin iodoacetate. J Chem Soc [B] 923–928

    Google Scholar 

  7. Adavovics JA, Cina JA, Hutchinson CR (1979) Minor alkaloids of Camptotheca acuminata. Phytochemistry 18:1085–1086

    Article  Google Scholar 

  8. Wani MC, Wall ME (1969) Plant antitumor agents. II. The structure of two new alkaloids from Camptotheca acuminata. J Org Chem 34:1364–1367

    Article  CAS  Google Scholar 

  9. Wall ME, Wani MC, Natschke SM, Nicholas AW (1986) Plant antitumor agents. XXII. Isolation of 11-hydroxycamptothecin from Camptotheca acuminata Decne: total synthesis and biological activity. J Med Chem 29:1553–1555

    Article  PubMed  CAS  Google Scholar 

  10. Tien HJ, Tien JM, Yeh MY, Wu TS, Huang CM (1977) Studies on the constituents of Camptotheca acuminata Decne. I. Constituents of leaves. Chemistry 51–4 (CA 92:37766e)

    Google Scholar 

  11. Lin LT, Chao TY, Hsu JS (1977) Chemical constituents of the anticancer plant Camptotheca acuminata Decne. I. Chemical constituents of the roots of Camptotheca acuminata. Acta Chim Sin 35:227–231

    CAS  Google Scholar 

  12. Hsu JS, Chao TY, Lin LT, Hsu CF (1977) Chemical constituents of the anticancer plant Camptotheca acuminata Decne. II. Chemical constituents of the fruits of Camptotheca acuminata Decne. Acta Chim Sin 35:193–200

    CAS  Google Scholar 

  13. Lin LZ, Song CQ, Xu RS (1982) Chemical constituents of the anticancer plant Camptotheca acuminata Decne. IV. Isolation and identification of 11-hydroxycamptothecin and four other compounds. Acta Chim Sin 40:85–89

    CAS  Google Scholar 

  14. Lin LT, Sung CC, Hsu JS (1978) Chemical constituents of the anticancer plant Camptotheca acuminata Decne. V. Other constituents of its fruits. Chemistry 327–328

    Google Scholar 

  15. Lin LT, Sung CC, Hsu JS (1979) A new anticancer alkaloid 11-hydroxycamptothecin. Kexue Tongbao 24:478–479

    CAS  Google Scholar 

  16. Ku KY, Tang TC (1980) Several botanical sources of camptothecin — an antitumor alkaloid. Chin Trad Herb Drugs 11:476–479

    CAS  Google Scholar 

  17. Govindachari TR, Viswanathan N (1972) 9-Methoxycamptothecin. New alkaloid from Mappia foetida. Indian J Chem 10:453–454

    CAS  Google Scholar 

  18. Tafur S, Nelson JD, DeLong DC, Svoboda GH (1976) Antiviral components of Ophiorrhiza mungos. Isolation of camptothecin and 10-hydroxycamptothecin. Lloydia 39:261–262

    PubMed  CAS  Google Scholar 

  19. Gunasekera SP, Badawi MM, Cordell GA, Farnsworth NR, Chitnis M (1979) Plant anticancer agents. X. Isolation of camptothecin and 9-methoxycamptothecin from Ervatamia heyneana. J Nat Prod 42:475–477

    Article  PubMed  CAS  Google Scholar 

  20. Lin LZ, Song CQ, Xu RS (1979) Chemical constituents of the anticancer plant Camptotheca acuminata Decne. III. Ellagic acids from the fruits of Camptotheca acuminata Decne. Acta Chim Sin 37:207–214

    CAS  Google Scholar 

  21. Stork G, Schultz AG (1971) The total synthesis of dl-camptothecin. J Am Chem Soc 93:4074–4075

    Article  PubMed  CAS  Google Scholar 

  22. Tang CSF, Morrow CJ, Rapoport H (1975) A total synthesis of dl-camptothecin. J Am Chem Soc 97:159–167

    Article  PubMed  CAS  Google Scholar 

  23. Shanghai No. 5 Pharmaceutical Plant, Shanghai No. 12 Pharmaceutical Plant, Shanghai Institute of Pharmaceutical Industrial Research, Shanghai Institute of Materia Medica (1976) Total synthesis of dl-camptothecin. Kexue Tongbao 21:40–42

    Google Scholar 

  24. Shanghai No. 5 Pharmaceutical Plant, Shanghai No. 12 Pharmaceutical Plant, Shanghai Institute of Pharmaceutical Industrial Research, Shanghai Institute of Materia Medica (1978) The total synthesis of dl-camptothecin. Sci Sin 21:87–98

    Google Scholar 

  25. Henecke H (1949) Zur Kenntnis der -Dicarbonyl-Verbindungen. VI. Die Kondensation von α-Aminomethylen-β-dicarbonyl-Verbindungen mit Ketonen und mit β-Dicarbonyl-Verbindungen. Chem Ber 82:41–46

    Article  Google Scholar 

  26. Wani MC, Rouman PE, Lindley JT, Wall ME (1980) Plant antitumor agents. XVIII. Synthesis and biological activity of camptothecin analogs. J Med Chem 23:554–560

    Article  PubMed  CAS  Google Scholar 

  27. Corey EJ, Crouse DN, Anderson JE (1975) A total synthesis of natural 20(5)-camptothecin. J Org Chem 40:2140–2141

    Article  PubMed  CAS  Google Scholar 

  28. Wenkert E, Dave KG, Lewis RG, Spragne PW (1967) General methods of synthesis of indole alkaloids. VI. Syntheses of dl-corynantheidine and a camptothecin model. J Am Chem Soc 89:6741–6745

    Article  PubMed  CAS  Google Scholar 

  29. Winterfeldt E (1971) Reaktionen an Indolderivaten. XIII. Chinolon-Derivate durch Autoxidation. Liebigs Ann Chem 745:23–30

    Article  CAS  Google Scholar 

  30. Warneke J, Winterfeldt E (1972) Reaktionen an Indolderivaten. XVI. Die autoxydative Indol-Chinolon-Umwandlung eines Camptothecin-Modells. Chem Ber 105:2120–2125

    Article  PubMed  CAS  Google Scholar 

  31. Hutchinson CR, Heckendorf AH, Straughn JL, Daddona PE, Cane DE (1979) Biosynthesis of camptothecin. III. Definition of strictosamide as the penultimate biosynthetic precursor assisted by carbon-13 and deuterium NMR-spectroscopy. J Am Chem Soc 101:3358–3369

    Article  CAS  Google Scholar 

  32. Cordeil GA (1974) Biosynthesis of indole alkaloids. Lloydia 37:219–298

    Google Scholar 

  33. Winterfeldt E, Korth T, Pike D, Boch M (1972) Biogenetically oriented total synthesis of camptothecin and 7-chlorocamptothecine. Angew Chem Int Ed Engl 11:289–290

    Article  PubMed  CAS  Google Scholar 

  34. Boch M, Korth T, Nelke JM, Pike D, Radunz H, Winterfeldt E (1972) Reaktionen an Indolderivaten. XVII. Die biogenetisch orientierte Totalsynthese von dl-Camptothecin and 7-Chlorcamptothecin. Chem Ber 105:2126–2142

    Article  PubMed  CAS  Google Scholar 

  35. Recher L, Chan H, Briggs L, Parry N (1972) Ultrastructural changes inducible with the plant alkaloid camptothecin. Cancer Res 32:2495–2501

    PubMed  CAS  Google Scholar 

  36. Horwith SB (1975) Camptothecin. In: Corcoran JW, Hahn FE (eds) Mechanism of Action of Antimicrobial and Antitumor Agents. Springer, Berlin Heidelberg New York, pp 48–57 (Antibiotics III)

    Google Scholar 

  37. Horwith SB, Chang CK, Grollman AP (1971) Camptothecin. I. Effects on nucleic acid and protein synthesis. Mol Pharmacol 7:632–644

    Google Scholar 

  38. Bosmann HB (1970) Camptothecin inhibits macromolecular synthesis in mammalian cells but not in isolated mitochondria or Escherichia coli. Biochem Biophys Res Commun 41:1412–1420

    Article  PubMed  CAS  Google Scholar 

  39. Horwith MS, Horwith SB (1971) Intracellular degradation of HeLa and adenovirus type 2 DNA induced by camptothecin. Biochem Biophys Res Commun 45:723–727

    Article  Google Scholar 

  40. Abelson HT, Penman S (1973) Induction of alkali labile links in cellular DNA by camptothecin. Biochem Biophys Res Commun 50:1048–1054

    Article  PubMed  CAS  Google Scholar 

  41. Spataro A, Kessel D (1972) Camptothecin-induced degradation and apparent reaggregation of DNA from L1210 cells. Biochem Biophys Res Commun 48:643–648

    Article  PubMed  CAS  Google Scholar 

  42. Li LH, Fraser TJ, Olin EJ, Buhyan BK (1972) Action of camptothecin on mammalian cells in culture. Cancer Res 32:2643–2650

    PubMed  CAS  Google Scholar 

  43. Lown JW, Chen HH (1980) Studies related to antitumor antibiotics. XIX. Studies on the effects of the antitumor agent camptothecin and derivatives on deoxyribonucleic acid. Mechanism of the scission of deoxyribonucleic acid by photoactivated camptothecin. Biochem Pharmacol 29:905–915

    Article  PubMed  CAS  Google Scholar 

  44. Kuwahara J, Suzuki T, Funakoshi K, Sugiura Y (1986) Photosensitive DNA cleavage and phage inactivation by copper (II)-camptothecin. Biochemistry 25:1216–1221

    Article  PubMed  CAS  Google Scholar 

  45. Horwith SB, Chang CK, Grollman AP (1972) Antiviral action of camptothecin. Antimicrob Agents Chemother 2:395–401

    Google Scholar 

  46. Becker Y, Asher Y (1975) In vitro synthesis of DNA in nuclei isolated from herpes simplex virus-infected cells, untreated and treated with metabolic inhibitors. Virology 63:209–220

    Article  PubMed  CAS  Google Scholar 

  47. Kelly DC, Avery RJ, Dimmock NJ (1974) Camptothecin. Inhibitor of influenza virus replication. J Gen Virol 25:427–432

    Article  PubMed  CAS  Google Scholar 

  48. Minor PD, Dimmock NJ (1975) Inhibition of synthesis of influenza virus proteins. Evidence for two host-cell-dependent events during multiplication. Virology 67:114–123

    Article  PubMed  CAS  Google Scholar 

  49. Minor PD, Dirnmock NJ (1977) Selective inhibition of influenza virus protein synthesis by inhibitors of DNA function. Virology 78:393–406

    Article  PubMed  CAS  Google Scholar 

  50. Wall ME (1969) Plant antitumor agents. V. Alkaloids with antitumor activity. In: Mothes K, Schreiber K, Schütte HR (eds) Symposiumberichte, 4. Internationales Symposium, Biochemie und Physiologie der Alkaloide. Akademie, Berlin, pp 77–87

    Google Scholar 

  51. Wall ME, Wani MC (1985) Antineoplastic structure activity relationships of camptothecin and related analogs. In: Chang HM, Yeung HW, Tso WW, Koo A (eds) Advances in Chinese Medicinal Material Research. World Scientific, Singapore, pp 391 – 405

    Google Scholar 

  52. Pan PC, Pan SY, Tu YH, Wang SY, Owen TY (1975) Studies on the derivatives of camptothecin. Acta Chim Sin 33:71–74

    CAS  Google Scholar 

  53. Sugasawa T, Toyoda T, Uchida N, Yamaguchi K (1976) Experiments on the synthesis of d,l-camptothecin. IV Synthesis and antileukemic activity of d,l-camptothecin analogues. J Med Chem 19:675–679

    Article  PubMed  CAS  Google Scholar 

  54. Boxmann E, Winterfeldt E (1978) Totalsynthese des 7-Methoxycamptothecins. Chem Ber 111:3403–3411

    Article  Google Scholar 

  55. Adamovics JA, Hutchinson CR (1979) Prodrug analogs of the antitumor alkaloid camptothecin. J Med Chem 22:310–314

    Article  PubMed  CAS  Google Scholar 

  56. Hartwell JL, Abbott BJ (1969) Antineoplastic principles in plants: recent development in the field. Adv Pharmacol Chemother 7:117–209

    Article  PubMed  CAS  Google Scholar 

  57. Schaeppi U, Fleischman RW, Cooney DA (1974) Toxicity of camptothecin (NCS-100880). Cancer Chemother Rep Part III 5:25–36

    Google Scholar 

  58. Yang JL, Han JX, Shen ZM, Xu B (1981) Study on the detoxification by monoammonium glycyrrhetate of anticancer drugs. Chin Pharm Bull 16:8–11

    CAS  Google Scholar 

  59. Chen RT, Hua Z, Lu Zy, Xu B (1980) Distribution and excretion of camptothecin suspension and sodium camptothecin in mice. Acta Pharmacol Sin 1:109–112

    CAS  Google Scholar 

  60. Gottlieb JA, Guarino AM, Call JB, Oliverio VT, Block JB (1970) Preliminary pharmacologic and clinical evaluation of camptothecin sodium (NSC-100880). Cancer Chemother Rep 54:461–470

    PubMed  CAS  Google Scholar 

  61. Moertel CG, Schutt AJ, Reitmeier RJ, Hahn RG (1972) Phase II study of camptothecin (NSC-100880) in the treatment of advanced gastrointestinal cancer. Cancer Chemother Rep 56:95–101

    PubMed  CAS  Google Scholar 

  62. Gottlieb JA, Luce JK (1972) Treatment of malignant melanoma with camptothecin (NSC-100880). Cancer Chemother Rep 56:103–105

    PubMed  CAS  Google Scholar 

  63. Xu B, Yang JL (1985) Hydroxycamptothecin as an antitumor agent. In: Chang HM, Yeung HW, Tso WW, Koo A (eds) Advances in Chinese Medicinal Material Research. World Scientific, Singapore, pp 377–389

    Google Scholar 

  64. Shanghai Institute of Materia Medica, Academia Sinica (1979) Studies on the anticancer action of 10-hydroxycamptothecin. In: Fox BW (ed) Basis for Cancer Therapy. I. Pergamon, Oxford, pp. 105–109 (Advances in Medical Oncology, Vol 5)

    Google Scholar 

  65. Tsou KC, Xu B, Miller EE, Lo KW (1981) Antitumor effect of (S)- 10-hydroxycamptothecin on mouse hepatoma BW 7756 and its possible mode of action. Anticancer Res 1:115–119

    PubMed  CAS  Google Scholar 

  66. Xu B (1982) The influence of several anticancer agents on cell proliferation, differentiation and the cell cycle of murine erythroleukemia cells. Am J Chin Med 9:268–276

    Google Scholar 

  67. Yang JL, Han JX, Shen ZM, Zhou XJ (1982) Effect of 10-hydroxycamptothecin on the cell proliferation and 3H-thymidine uptake into DNA of human gastric carcinoma cell (SGC-7901) in vitro. Tumor 2:21–23

    Google Scholar 

  68. Yang JL, Shen ZM, Sun YF, Han JX, Xu B (1985) Cultured human hepatoma cell (BEL-7404) for anticancer drug screening. Acta Pharmacol Sin 6:144–148

    CAS  Google Scholar 

  69. Ling YH, Yu WJ, Xu B (1983) Effects of 10-hydroxycamptothecin on the transport of pyrim-idine nucleosides in murine hepatoma cells. Acta Biochim Biophys Sin 15:543–548

    CAS  Google Scholar 

  70. Yang JL, Han JX, Shen ZM, Xu B (1981) Effects of 10-hydroxycamptothecin on cAMP and cGMP levels in hepatoma and liver tissue of mice. Acta Pharmacol Sin 2:248–252

    CAS  Google Scholar 

  71. Creasey WA, Richards M, Gil D, Tsou KC (1983) Action of (5)-10-hydroxycamptothecin on P388 leukemia and distribution of the drug in mice. Cancer Treat Rep 67:179–182

    PubMed  CAS  Google Scholar 

  72. Ling YH, Zhao CS, Xu B (1986) Effects of 10-hydroxycamptothecin on chromatin protein synthesis in murine hepatoma cells. Acta Pharmacol Sin 7:285–288

    CAS  Google Scholar 

  73. Huang CC, Han CS, Yue XF, Shen CM, Wang SW, Wu FG, Xu B (1983) Cytotoxicity and sister chromatid exchanges induced in vitro by six anticancer drugs developed in the People’s Republic of China. JNCI 71:841–847

    PubMed  CAS  Google Scholar 

  74. Wang XW, Shen ZM, Yang JL, Xu B (1986) Inhibitory effect of hydroxycamptothecin on colony formation of KB cells and DNA damage. Acta Pharm Sin 21:492–497

    CAS  Google Scholar 

  75. Ling YH, Yu WJ, Xu B (1984) Effect of 10-hydroxycamptothecin on nuclear RNA polymerase activity in mouse hepatoma cells. Acta Pharmacol Sin 5:211–213

    CAS  Google Scholar 

  76. Wang ZW, Shu RS, Xu B (1979) Effect of hydroxycamptothecin on the ultrastructure of ascitic hepatoma cells in mice. Chin J Oncol 1:183–185

    CAS  Google Scholar 

  77. Yang JL, Han JX, Xu B (1980) Distribution and excretion of 10-hydroxcycamptothecin and its effects on immune response. Acta Pharmacol Sin 1:44–48

    CAS  Google Scholar 

  78. Shanghai Institute of Materia Medica, Academia Sinica (1978) Studies on the anticancer action of 10-hydroxycamptothecin. Chin Med J 58:598–602

    Google Scholar 

  79. Department of Oral and Maxillo-Facial Surgery, 9th People’s Hospital, Shanghai, 2nd Medical College (1978) China made camptothecin and hydroxycamptothecin in the treatment of oral and maxillofacial malignancies. Chin J Stomatol 13:75–77

    Google Scholar 

  80. Jiang TL, Salmon SE, Liu RM (1983) Activity of camptothecin, harringtonin, cantharidin and curcumae in the human tumor stem cell assay. Eur J Cancer Clin Oncol 19:263–270

    Article  PubMed  CAS  Google Scholar 

  81. Hsiang YH, Hertzberg R, Hecht S, Liu LF (1985) Camptothecin induces protein-linked DNA breaks via mammalian DNA topoisomerase I. J Biol Chem 260:14873–14878

    PubMed  CAS  Google Scholar 

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Tang, W., Eisenbrand, G. (1992). Camptotheca acuminata Decne. In: Chinese Drugs of Plant Origin. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-73739-8_33

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  • DOI: https://doi.org/10.1007/978-3-642-73739-8_33

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