Recent Experimental and Clinical Data Concerning Antitumor and Cytotoxic Agents from Plants

  • G. A. Cordell
Part of the Proceedings in Life Sciences book series (LIFE SCIENCES)

Abstract

Plants have been used in the treatment of cancer for over 3500 years (Hartwell, 1967), but it is only since 1959 that a concerted systematic effort has been made to screen crude plant extracts for their inhibitory activity against animal tumor systems. In this period, in-excess of 180,000 plant extracts from 2500 genera of plants have been screened by a program conducted under the auspices of the National Cancer Institute.

Keywords

Vinblastine Arginase Sesquiterpene Enamine Diterpenes 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Abraham, D.J., Rosenstein, R.D., McCandy, E.L.: Single crystal X-ray structures of chemotherapeutic agents. II. The structure of cephalotaxine methiodide. Tetrahedron Lett. 4085–4086 (1969)Google Scholar
  2. Ando, M., Büchi, G., Ohnuma, T.: The total synthesis of vindoline. J. Am. Chem. Soc. 97, 6880–6881 (1975)CrossRefGoogle Scholar
  3. Anon: Antitumor effect and toxicity of the alkaloid of Crotalaria assamioa. Chung-Hua I Hsueh Tsa Chih 104, 472–477 (1973).Google Scholar
  4. Anon: Antitumor effect and toxicity of the alkaloid of Crotalaria assamioa Through Chem. Abstr. 83, 11176f (1973)Google Scholar
  5. Anon: Crotalaria assamioa. Resource plant of monocrotaline. Chih. Wu Hsueh Pao 16, 380–381 (1974a).Google Scholar
  6. Anon: Crotalaria assamioa. Resource plant of monocrotaline. Through Chem. Abstr. 83, 25024 (1974a).Google Scholar
  7. Anon: Semisynthetic preparation of vincristine. Fr. Demande 2, 210, 393 (1974b). Through Chem. Abstr. 82, 73294bGoogle Scholar
  8. Anon: Partial synthesis of harringtonine. K’O Hsueh T’ung Pao 20, 437 (1975a).Google Scholar
  9. Anon: Partial synthesis of harringtonine. Through Chem. Abstr. 84, 105859z (1975a).Google Scholar
  10. Anon: N-Formyl bisindole alkaloids. Belg. Pat. 823, 560 (1975b). Through Chem. Abstr. 84, 59835pGoogle Scholar
  11. Anon: 9-Hydroxyellipticine. Ger. Offen. 2, 451, 360 (1975c). Through Chem. Abstr. 83, 126493yGoogle Scholar
  12. Anon: Total synthesis of dl-camptothecine. K’O Hsueh T’ung Pao 21, 40–44 (1976).Google Scholar
  13. Anon: Total synthesis of dl-camptothecine. Through Chem. Abstr. 84, 122100n (1976).Google Scholar
  14. Arora, S.K., Bates, R.B., Grady, R.A., Germain, G., Declerco, J.P., Powell, R.G.: Crystal and molecular structure of cephalotaxine. J. Org. Chem. 41, 551–554 (1976)PubMedCrossRefGoogle Scholar
  15. Arora, S.K., Bates, R.B., Grady, R.A., Powell, R.G.: Crystal and molecular structure of cephalotaxine p-bromo benzoate. J. Org. Chem. 39, 1269–1271 (1974)PubMedCrossRefGoogle Scholar
  16. Atta-ur-Rahman, Basha, A., Ghazala, M.: Synthetic studies of antileukemic alkaloids. VII. The partial synthesis of vinblastine. Tetrahedron Lett. 2351–2354 (1976)Google Scholar
  17. Besselievere, R., Thai, C., Husson, H.-P., Potier, P.: Novel synthesis of the indole alkaloid ellipticine. J. Chem. Soc., Chem. Commun. 90–91 (1975)Google Scholar
  18. Bradley, J.C., Büchi, G.: A short synthesis of camptothecin. J. Org. Chem. 41, 699–701 (1976)PubMedCrossRefGoogle Scholar
  19. Brändange, S., Josephson, S., Valién, S., Powell, R.G.: Absolute configuration of 2,3-dihydroxy-2-isopentylbutanedioic acid, a component of the alkaloid isoharringtonine. Acta Chem. Scand. 28B, 1237–1248 (1974)CrossRefGoogle Scholar
  20. Brannon, D.R., Neuss, N.: Microbial N-demethylation of vindoline and vinblastine. Ger. Offen. 2,440,931 (1975). Through Chem. Abstr. 83, 7184kGoogle Scholar
  21. Bryan, R.F., Smith, P.M.: X-Ray determination of the structure of podolide, an antileukemic norditerpene dilactone. J. Chem. Soc. Perkin Trans. II. 1482–1486 (1975)Google Scholar
  22. Büchi, G.H.: Synthesis of naturally occuring indole derivatives. Chimia 29, 172–173 (1975)Google Scholar
  23. Büchi, G.H., Kulsa, P., Ogasawara, K., Rosati, R.L.: Synthesis of velbanamine and catharanthine. J. Am. Chem. Soc. 92, 999–1005 (1970)PubMedCrossRefGoogle Scholar
  24. Büchi, G.H., Kulsa, P., Rosati, R.L.: The total synthesis of velbanamine. J. Am. Chem. Soc. 90, 2448–2449 (1968)PubMedCrossRefGoogle Scholar
  25. Büchi, G.H., Matsumoto, K.E., Nishimura, H.: Total synthesis of vindorosine. J. Am. Chem. Soc. 93, 3299–3301 (1971)PubMedCrossRefGoogle Scholar
  26. Corey, E.J., Bock, M.G.: Stereocontrolled route to a key intermediate for the synthesis of maytansine. Tetrahedron Lett. 2643–2646 (1975)Google Scholar
  27. Corey, E.J., Grouse, D.N., Anderson, J.E.: A total synthesis of natural 20 (S)-camptothecin. J. Org. Chem. 40, 2140–2141 (1975)PubMedCrossRefGoogle Scholar
  28. Danielli, B.: Recenti acquisizioni nel campo degli antitumorali di origine vegetale. Parte I. Fitoterapia 42, 11–39 (197la)Google Scholar
  29. Danielli, B.: Recenti acquisizioni nel campo degli antitumorali di origine vegetale. Parte II. Fitoterapia 42, 94–120 (1971b)Google Scholar
  30. Dat-Xuong, N., Adeline, M.-T., Lecointe, P., Janot, M.-M.: L’hydroxy-9-ellipticine et quelques uns de ses derives. C.R. Acad. Sci., Paris, Ser. D. 281, 623–626 (1975)Google Scholar
  31. Demuth, M.R., Garrett, P.E., White, J.D.: Synthesis of (+)-crotepoxide, (+) -epicrotepoxide, and (+) -isocrotepoxide. J. Am. Chem. Soc. 98, 634–635 (1976)PubMedCrossRefGoogle Scholar
  32. Desai, H.K., Gawad, D.H., Govindachari, T.R., Joshi, B.S., Kamat, V.N., Parthasarathy, P.C., Ramachandran, K.S., Shahbhag, M.N., Sidhaye, A.R., Viswanathan, N.: Chemical investigation of some Indian plants. Part VIII. Indian J. Chem. 13, 97–98 (1975)Google Scholar
  33. Dutschewska, H.B., Mollov, N.M.: Structure of dehydrothaiicarpine, a new aporphine benzylisoquinoline alkaloid from Thalictrum minus spp. elatum. Chem. Ind. (London) 770–771 (1966)Google Scholar
  34. Elliot, W.J., Fried, J.: Maytansinoids. Synthesis of a fragment of known absolute configuration involving chiral centers C-6 and C-7. J. Org. Chem. 41, 2469–2475 (1976)CrossRefGoogle Scholar
  35. Festy, B., Poisson, J., Paoletti, C.: A new intercalating drug: 9-methoxyellipticine. FEBS Lett. 17, 321–323 (1971)PubMedCrossRefGoogle Scholar
  36. Gillespie, J.P., Amoros, L.G., Stermitz, F.R.: Synthesis of fagaronine. An anticancer benzophenanthridine alkaloid. J. Org. Chem. 39, 3239–3241 (1974)PubMedCrossRefGoogle Scholar
  37. Gilmore, C.J., Bryan, R.F., Kupchan, S.M.: Conformation and reactivity of the macrocyclic tumor-inhibitory alkaloid tetrandrine. J. Am. Chem. Soc. 98, 1947–1952 (1976)PubMedCrossRefGoogle Scholar
  38. Gosalvez, M., Blanco, M., Hunter, J., Miko, M., Chance, B.: Effects of anticancer agents on the respiration of isolated mitochondria and tumor cells. Europ. J. Cancer 10, 567–574 (1974)Google Scholar
  39. Gralla, E.J., Coleman, G.L., Jonas, A.M.: Toxicology studies with d-tetrandrine (NSC-77037), a plant alkaloid with vascular and lymphotoxic effects in dogs and monkeys. Cancer Chemother. Repts. Pt. 3 5, 79–85 (1974)Google Scholar
  40. Grieco, P.A., Nishizawa, M., Burke, S.D., Marinovic, N.: Total synthesis of (+)- vernolepin and (+)-vernomenin. J. Am. Chem. Soc. 98, 1612–1613 (1976)PubMedCrossRefGoogle Scholar
  41. Grollman, A.P., Jarkovsky, Z.: Emetine and related alkaloids. In: Antibiotics. Mechanism of Action of Antimicrobial and Antitumor Agents. Corcoran, J.W., Hahn, F.E. (eds.). New York: Springer, 1975, Vol. III, pp. 420–435Google Scholar
  42. Hartwell, J.L.: Plants used against Cancer. A survey. Lloydia 30, 379–436 (1967)Google Scholar
  43. Hartwell, J.L.: Plants used against Cancer. A survey. Lloydia 32, 204–255 (1971)Google Scholar
  44. Hartwell, J.L., Abbott, B.J.: Antineoplastic principles in plants: Recent developments in the field. Advan. Pharmacol. Chemother. 7, 117–209 (1969)CrossRefGoogle Scholar
  45. Hayashi, Y., Sakan, T., Sakurai, Y., Tashiro, T.: Antitumor activity of naglactones. Gann 66, 587–588 (1975)PubMedGoogle Scholar
  46. Hayat, M., Mathe, G., Janot, M.-M., Potier, P., Dat-Xuong, N., Cave, A., Sevenet, T., Kan-Fan, C., Poisson, J., Miet, J., Le Men, J., Le Goffic, F., Go Uvette, A., Ahond, A., Dalton, L.K., Connors, T.A.: Experimental screening of three forms and nineteen derivatives or analogs of ellipticine: Oncostatic effect on L-1210 leukemia and immunosuppressive effect of four of them. Biomedicine 21, 101–106 (1974)PubMedGoogle Scholar
  47. Herman, E.H., Chadwick, D.P.: Cardiovascular effects of d-tetrandrine. Pharmacology 12, 97–109 (1974)PubMedCrossRefGoogle Scholar
  48. Herman, E.H., Chadwick, D.P., Mhatre, R.M.: Comparison of the acute hemolytic and cardiovascular actions of ellipticine (NSC-71795) and some ellipticine analogs. Cancer Chemother. Repts. Pt. 1 58, 637–643 (1974a)Google Scholar
  49. Herman, E.H., Lee, I.P., Mhatre, R.M., Chadwick, D.P.: Prevention of hemolysis induced by ellipticine (NSC-71795) in rhesus monkeys. Cancer Chemother Repts. Pt. 1 58, 171–9 (1974b)Google Scholar
  50. Hirotsu, K., Higuchi, T., Shimada, A., Hayashi, Y., Sakan, T.: Crystal and mole-cular structure of nagilactone. A diacetate. Bull. Chem. Soc. Japan 48, 1157–1162 (1975)CrossRefGoogle Scholar
  51. Horwitz, S.B.: Camptothecin. Antibiotics 3, 48–57 (1975)Google Scholar
  52. Huang, C.H., Kreilgard, B., Repta, A.J.: Formulation of a parenteral solution of acetylacronycinium Perchlorate a soluble prodrug of the antitumor agent acronycine. Bull. Parenter. Drug Assoc. 30, 1–12 (1976)PubMedGoogle Scholar
  53. Hughes, L.R., Raphael, R.A.: Synthesis of the antileukemic lignan precursor (+)-steganone. Tetrahedron Lett. 1543–1546 (1976)Google Scholar
  54. Israel, L., Depierre, A., Chahinian, P.: Dehydroemetine in 50 disseminated carcinomas unresponsive to other drugs. Proc. Am. Assoc. Cancer Res. 15, 11 (1974)Google Scholar
  55. Jewers, K., Manchanda, A.H., Rose, H.M.: Naturally-occurring antitumor agents. Progr. Med. Chem. 9, 1–63 (1973)CrossRefGoogle Scholar
  56. Jolad, S.D., Wiedhopf, R.M., Cole, J.R.: Tumor-inhibitory agent from Zaluzania robinsonii (Compositae). J. Pharm. Sci. 63, 1321–1322 (1974)PubMedCrossRefGoogle Scholar
  57. Jolad, S.D., Wiedhopf, R.M., Cole, J.R.: Tumor-inhibitory agent from Montezuma speciosissima (Malvaceae). J. Pharm. Sci. 64, 1889–1890 (1975)PubMedCrossRefGoogle Scholar
  58. Jovanovics, K., Szasz, K., Fekete, G., Bittner, E., Dezberi, E., Eles, J.: Chromic acid oxidation of vinblastine sulfate to form vincristine. U.S. Patent 3,899, 493 (1975). Through Chem. Abstr. 83, 179360fGoogle Scholar
  59. Kametani, T., Ichikawa, Y., Suzuki, T., Fukumoto, K.: Fascinating synthesis of olivacine. Heterocycles 3, 401 (1975a)CrossRefGoogle Scholar
  60. Kametani, T., Suzuki, T., Ichikawa, Y., Fukumoto, K.: Studies on the synthesis of heterocyclic compounds. Part CDXXXIV. A novel total synthesis of olivacine. (l,5-Dimethyl-6H-pyridol[4,3-b-]carbazole). J. Chem. Soc. Perkin Trans. I 2102–2104 (1975b)CrossRefGoogle Scholar
  61. Kende, A.S., Liebeskind, L.S.: Total synthesis of steganacin. J. Am. Chem. Soc. 98, 267–268 (1976)PubMedCrossRefGoogle Scholar
  62. Kotani, E., Kitazawa, M., Tobinaga, S.X.: New synthesis of the alkaloid (+)-cryptopleurine by anodic oxidation. Tetrahedron Lett. 30, 3027–3030 (1974)Google Scholar
  63. Krohn, K., Winterfeldt, E.: Alkylierung von Camptothecinvorstufen — ein neuer Weg zum Camptothecin. Chem. Ber. 108, 3030–3042 (1975)CrossRefGoogle Scholar
  64. Kupchan, S.M.: Antileukemic triepoxyditerpenes from Tripterygium wilfordii. Ger. Offen. Patent 2,316,916 (1974). Through Chem. Abstr. 82, 77095kGoogle Scholar
  65. Kupchan, S.M., Baxter, R.L.: Mezerein: Antileukemic principle isolated from Daphne mezereum L. Science 187, 652–653 (1975)PubMedCrossRefGoogle Scholar
  66. Kupchan, S.M., Baxter, R.L., Ziegler, M.F., Smith, P.M., Bryan, R.F.: Podolide, a new antileukemic norditerpene dilactone from Podocarpus gracilior. Experientia 31, 137–138 (1975a)PubMedCrossRefGoogle Scholar
  67. Kupchan, S.M., Branfman, A.R., Sneden, A.T., Verma, A.K., Dailey, R.G., Jr., Komoda, Y., Nagao, Y.: Novel maytansinoids. Naturally occurring and synthetic antileu-kemic esters and maytansinol. J. Am. Chem. Soc. 97, 5294–5295 (1975b)PubMedCrossRefGoogle Scholar
  68. Kupchan, S.M., Britton, R.W., Lacadie, J.A., Ziegler, M.F., Sigel, S.W.: The isolation and structure elucidation of bruceantin and bruceantinol, new potent antileukemic quassinoids from Brucea antidysenterica. J. Org. Chem. 40, 648–656 (1975c)PubMedCrossRefGoogle Scholar
  69. Kupchan, S.M., Britton, R.W., Ziegler, M.F., Gilmore, C.J., Restivo, R.J., Bryan, R.F.: Steganacin and steganangin, novel antileukemic lignan lactones from Steganotaenia araliacea. J. Am. Chem. Soc. 95, 1335–1336 (1973a)PubMedCrossRefGoogle Scholar
  70. Kupchan, S.M., Chakravarti, K.K., Yokoryama, N.: Thalictrum Alkaloids I. Thalicarpine, a new hypotensive alkaloid from Thalictrum dasycarpum. J. Pharm. Sci. 52, 985–988 (1963)PubMedCrossRefGoogle Scholar
  71. Kupchan, S.M., Court, W.A., Dailey, R.G., Jr., Gilmore, C.J., Bryan, F.F.: Triptolide and tripdiolide, novel antileukemic diterpenoid triepoxides from Tripterygium wilfordii. J. Am. Chem. Soc. 94, 7194–7195 (1972a)PubMedCrossRefGoogle Scholar
  72. Kupchan, S.M., Dessertine, A.L., Blaylock, B.T., Bryan, R.R.: Isolation and structure elucidation of allamandin, an antileukemic iridoid lactone from Allamanda cathartica. J. Org. Chem. 39, 2477–2482 (1974a)PubMedCrossRefGoogle Scholar
  73. Kupchan, S.M., Hemingway, R.J., Smith, R.M.: Tumor inhibitors. XLV. Crotepoxide, a novel cyclohexane diepoxide tumor inhibitor from Croton macrostachys. J. Org. Chem. 34, 3898–3902 (1969)PubMedCrossRefGoogle Scholar
  74. Kupchan, S.M., Hemingway, R.J., Werner, D., Karin, A., McPhail, A.T., Sim, G.A.: Tumor inhibitors XXXI. Vernolepin, a novel elemanolide dilactone tumor inhibitor from Verononia hymenolepis. J. Am. Chem. Soc. 90, 3596–3597 (1968)PubMedCrossRefGoogle Scholar
  75. Kupchan, S.M., Komoda, Y., Branfman, A.R., Dailey, R.G., Jr., Zimmerly, V.A.: Novel maytansinoids. Structural interrelations and requirements for antileukemic activity. J. Am. Chem. Soc. 96, 3706–3708 (1974b)CrossRefGoogle Scholar
  76. Kupchan, S.M., Komoda, Y., Court, W.A., Thomas, G.J., Smith, R.M., Karim, A., Gilmore, C.J., Haltiwanger, R.C., Bryan, R.F.: Maytansine, a novel antileukemic ansa macrolide from Maytenus ovatus. J. Am. Chem. Soc. 94, 1354–1356 (1972b)PubMedCrossRefGoogle Scholar
  77. Kupchan, S.M., Komoda, Y., Thomas, G.J., Court, W.A.: Ansa macrolides. U.S. Pat. 3,896,111 (1975d). Through Chem. Abstr. 83, 209396sGoogle Scholar
  78. Kupchan, S.M., Komoda, Y., Thomas, G.J., Hintz, H.P.J.: Maytanprine and maytanbutine, new antileukemic ansa macrolides from Maytenus buchananii. J. Chem. Soc., Chem. Commun. 1065 (1972c)Google Scholar
  79. Kupchan, S.M., Lacadie, J.A.: Dehydroailanthinone, a new antileukemic quassinoid from Pierreodendron kerstingii. J. Org. Chem. 40, 654–655 (1975)PubMedCrossRefGoogle Scholar
  80. Kupchan, S.M., Liepa, A.J.: Tumor-inhibiting thalicarpines. Brit. Pat. 1,373,399. (1974a). Through Chem. Abstr. 83, 59135qGoogle Scholar
  81. Kupchan, S.M., Liepa, A.J.: Cytotoxic hernandaline. Brit. Pat. 1,373,400 (1974b). Through Chem. Abstr. 83, 79456yGoogle Scholar
  82. Kupchan, S.M., Liepa, A.J.: Synthesis of thalicarpine. U.S. Pat. 3,875,167 (1975). Through Chem. Abstr. 83, 28433fGoogle Scholar
  83. Kupchan, S.M., Liepa, A.J., Baxter, R.L., Hintz, H.P.J.: New alkaloids and related artifacts from Cyclea pettata. J. Org. Chem. 38, 1846–1852 (1973b)PubMedCrossRefGoogle Scholar
  84. Kupchan, S.M., Schubert, R.M.: Selective alkylation. A biomimetic reaction of the antileukemic triptolides. Science 185, 791–793 (1974)PubMedCrossRefGoogle Scholar
  85. Kupchan, S.M., Sweeny, J.G., Baxter, R.L., Murae, T., Zimmerly, V.A., Sickles, B.: Gnididin, gniditrin, and gnidicin, novel potent antileukemic diterpenoid esters from Gnidia lamprantha. J. Am. Chem. Soc. 92, 672–673 (1975e)CrossRefGoogle Scholar
  86. Kupchan, S.M., Uchida, I., Branfman, A.R., Dailey, R.G., Jr., Fei, B.Y.: Antileukemic principles isolated from Euphorbiaceae plants. Science 191, 571–572 (1976)PubMedCrossRefGoogle Scholar
  87. Kutney, J.P.: Studies on the total synthesis of bisindole alkaloids in the vinblastine-vincristine series. American Society of Pharmacognosy Meeting, Cable, Wisconsin, July 11–16th, 1976Google Scholar
  88. Kutney, J.P., Balsevich, J., Bokelman, G.H., Hibino, T., Itoh, I., Ratcliffe, A.H.: Studies on the synthesis of bisindole alkaloids. III. The synthesis of leurosine and 3’-hydroxyvinblastine. Heterocycles 4, 997–1005 (1976)CrossRefGoogle Scholar
  89. Kutney, J.P., Beck, J., Bylsma, F., Cook, J., Cretney, W.J., Fuji, K., Imhof, R., Treasurywala, A.M.: Total synthesis of indole and dihydroindole alkaloids. VIII. Studies on the synthesis of bisindole alkaloids in the vinblastine-vincristine series. The chloroindolenine approach. Helv. Chem. Acta 58, 1690–1719 (1975a)CrossRefGoogle Scholar
  90. Kutney, J.P., Bylsma, F.: Studies on the synthesis of monomeric and dimeric Vinca alkaloids. The total synthesis of isovelbanamine, velbanamine, cleavamine, 18β-carbomethoxycleavamine and catharanthine. J. Am. Chem. Soc. 92, 6090–6092 (1970)PubMedCrossRefGoogle Scholar
  91. Kutney, J.P., Bylsma, F.: Total synthesis of indole and dihydroindole alkaloids. VII. The total synthesis of isovelbanamine, velbanamine, cleavamine, 18β-carbomethoxylcleavamine and catharanthine. Helv. Chim. Acta 58, 1672–1689 (1975)PubMedCrossRefGoogle Scholar
  92. Kutney, J.P., Cook, J., Fuji, K., Treasurywala, A.M., Clardy, J., Fayos, J., Wright, H.: Synthesis of bisindole alkaloids. Synthesis, structure, and absolute configuration of 18’-epi-4’-deoxo-4’-epivinblastine, 18’-decarbomethoxy-18’-epi-4-epivinblastine, and 18’-epi-3’,4’-dehydrovinblastine. Heterocycles 3, 205–212 (1975b)CrossRefGoogle Scholar
  93. Kutney, J.P., Gregonis, D.E., Imhof, R., Itoh, I., Jahngen, E., Scott, A.I., Chan, W.K.: Absolute stereochemistry of the bisindole alkaloids of the vinblastine type. Circular dichroism studies. J. Am. Chem. Soc. 97, 5013–5015 (1975c)PubMedCrossRefGoogle Scholar
  94. Kutney, J.P., Grierson, D.S.: Improved synthesis of the pyrido-carbazole indole alkaloid olivacine. Heterocycles 3, 171–177 (1975)CrossRefGoogle Scholar
  95. Kutney, J.P., Ratcliffe, A.H., Treasurywala, A.M., Wunderly, S.: Synthesis of bisindole alkaloids. II. Synthesis of 3’ 4’-dehydrovinblastine, 4’-deoxyvin-blastine, and related analogs. Biogenetic approach. Heterocyles 3, 639–649 (1975d)CrossRefGoogle Scholar
  96. Langlois, Y., Langlois, N., Potier, P.: Application d’un schéma biogénétique en synthèse totale: 1’ellipticine. Tetrahedron Lett. 955–958 (1975)Google Scholar
  97. Langlois, N., Potier, P.: Hemisynthese de la leurosidine, alkaloide antitumoral isolé de Catharanthus roseus G. Don (Apocynacêes) Tetrahedron Lett. 1099–1102 (1976)Google Scholar
  98. Lee, K.-H., Cowherd, C.M., Wolo, M.T.: Antitumor agents XV: Deoxyelephantopin, an antitumor principle from Elephantopus carolinianus Willd. J. Pharm. Sci. 64, 1572–1573 (1975a)PubMedCrossRefGoogle Scholar
  99. Lee, K.-H., Ibuka, T., Huang, H.-C., Harris, D.L.: Antitumor agents XIV: Molephantinin, a new potent antitumor sesquiterpene lactone from Elephantopus mollis. J. Pharm. Sci. 64, 1077–1078 (1975b)PubMedCrossRefGoogle Scholar
  100. Lee, K.-H., Imakura, Y., Sims, D., McPhail, A.T., Onan, K.D.: Structure and stereo-chemistry of microlenin, a novel antitumor dimeric sesquiterpene lactone from Uelenium mievooephalum; X-Ray crystal structure. Chem. Commun. 341–342 (1976a)Google Scholar
  101. Lee, K.-H., Kim, S.-H., Furukawa, H., Pianthdosi, C., Huang, E.-S.: Antitumor agents. II. Synthesis and cytotoxic activity of helenalin related derivatives. J. Med. Chem. 18, 59–63 (1975c)PubMedCrossRefGoogle Scholar
  102. Lee, L.-H., Kimura, T., Okamoto, M., Cowherd, C.M., McPhail, A.T., Onan, K.D.: The structure and stereochemistry of eupahyssopin, a new antitumor germacranolide from Eupatorium hyssopifolium. Tetrahedron Lett. 1051–1054 (1976b)Google Scholar
  103. LePecq, J.B., Gosse, C., Dat-Xuong, N., Paoletti, C.: Two new antitumoral compounds: 9-hydroxy-2-methyl ellipticinium and 9-hydroxy-2,6-dimethyl ellipticinium. Action on L1210 mouse leukemia. CR. Acad. Sci., Paris, Ser. D. 281, 1365–1367 (1975)Google Scholar
  104. Li, S.-W., Dai, J.-Y.: A study on deoxyharringtonine and its analogs. Hua Hsueh Hsueh Pao 33, 75–78 (1975)Google Scholar
  105. Maleev, A., Stoichkov, J., Todorov, D., Mikhalaeva, K., Mollov, N.M., Duchevska, Kh.: Antitumor effect of the alkaloid thalibalstine. Dokl. Bolg. Akad. Nauk 28, 713–715 (1975). Through Chem. Abstr. 83, 172576xGoogle Scholar
  106. Messmer, W.M., Tin-Wa, M., Fong, H.H.S., Bevelle, C., Farnsworth, N.R., Abraham, D.J., Trojánek, J.: Fargaronine, a new tumor inhibitor isolated from Fagava zanthoxyloides Lam. (Rutaceae). J. Pharm. Sci. 61, 1858 (1972)PubMedCrossRefGoogle Scholar
  107. Meyers, A.I., Brinkmeyer, R.S.: Progress toward the total synthesis of maytansine. A model system containing the C-7 to C-16 moiety (southern and eastern zone). Tetrahedron Lett. 1749–1752 (1975)Google Scholar
  108. Meyers, A.I., Home, D., Shaw, C.C., Trefonas, L.M., Majeste, R.J.: Progress toward the total synthesis of maytansine. A stereoselective synthesis of the C-1 to C-7 moiety (northern zone). Tetrahedron Lett. 1745–1748 (1975)Google Scholar
  109. Meyers, A.I., Shaw, C.-C: Studies directed toward the total synthesis of maytansine. The preparation and properties of the carbinolamide moiety. Tetrahedron Lett. 717–720 (1974)Google Scholar
  110. Mikolajczak, K.L., Powell, R.G., Smith, C.R., Jr.: Deoxyharringtonine, a new antitumor alkaloid from Cephalotaxus: structure and synthetic studies. Tetrahedron Lett. 28, 1995–2001 (1972)Google Scholar
  111. Mikolajczak, K.L., Powell, R.G., Smith, C.R., Jr.: Preparation and antitumor activity of a rearranged ester of cephalotaxine. J. Med. Chem. 18, 63–66 (1975)PubMedCrossRefGoogle Scholar
  112. Mikolajczak, K.L., Smith, C.R., Jr., Powell, R.G.: Partial synthesis of harring-tonine analogs. J. Pharm. Sci. 63, 1280–1283 (1974a)PubMedCrossRefGoogle Scholar
  113. Mikolajczak, K.L., Smith, C.R., Jr., Weisleder, D., Kelly, T.R., McKerma, J.C., Christenson, P.A.: Synthesis of Deoxyharringtonine. Tetrahedron Lett. 283–286 (1974b)Google Scholar
  114. Moertel, G.G., Schutt, A.J., Hahn, R.G., Reitemeier, R.J.: Treatment of advanced gastrointestinal cancer with emetine (NSC-33669). Cancer Chemother. Rep., Pt. 1 58, 229–232 (1974)Google Scholar
  115. Mohn, K.W., Waring, M.J., Glaubiger, D., Friedman, C.A.: Intercalative binding of ellipticine to DNA. Cancer Res. 35, 71–76 (1975)Google Scholar
  116. Neuss, N., Mallett, G.E., Brannon, D.R., Mabe, J.A., Horton, H.R., Huckstep, L.L.: Vinca Alkaloids. XXXIII. Microbiological conversions of vincaleukoblastine, an antitumor alkaloid from Vinca rosea. L. Helv. Chim. Acta 57, 1886–1890 (1974)CrossRefGoogle Scholar
  117. Ninomiya, I., Naito, T., Ishii, H.: Synthesis of N-demethylfagaronine, Heterocyles 3, 307–309 (1975a)CrossRefGoogle Scholar
  118. Ninomiya, I., Naito, T., Ishii, H., Ishida, T., Ueda, M., Harada, K.: Syntheses of dihydroderivatives of the benzo[c]phenanthridine alkaloids avicine and nitidine by enamide photocyclization. J. Chem. Soc. Perkin Trans. 1, 762–764 (1975b)CrossRefGoogle Scholar
  119. O’Connor, T.E., Aldrich, C., Haddi, A., Lomax, N., Okano, P., Sethi, S., Wood, H.B.: Proc. 66th Ann. Mett. Am. Assoc. Cancer Res. 16, 29 (1975)Google Scholar
  120. Oda, K., Ichihara, A., Sakamura, S.: Total synthesis of DL-crotepoxide. Tetrahedron ` 3187–3190 (1975)Google Scholar
  121. Ogura, M., Cordell, G.A., Farnsworth, N.R.: Potential Anticancer agents. III. Jacaranone., a novel phytoquinoid from Jacaranda caucana. Lloydia 39, 255–257 (1976)PubMedGoogle Scholar
  122. Parry, R.J., Schwab, J.M.: Biosynthesis of Cephalotaxus alkaloids. I. Novel moden of tyrosine incorporation into cephalotaxine. J. Am. Chem. Soc. 97, 2555–2557 (1975)PubMedCrossRefGoogle Scholar
  123. Petlichnaya, L.I., Turkevich, N.M.: Some thiophosphamide derivatives of berberine and their interaction with hydrogen chloride. Farm. Zh. (Kiev) 30, 40–43 (1975)Google Scholar
  124. Pettit, G.R., Budzinski, J.C., Cragg, G.M., Brown, P., Johnston, L.D.: Antineoplastic agents 34. Helenium autunnale L. J. Med. Chem. 17, 1013–1016 (1974)PubMedCrossRefGoogle Scholar
  125. Pettit, G.R., Herald, C.L., Judd, G.F., Bolliger, G., Thayer, P.S.: Antineoplastic and cytotoxic components of desert Baileya. J. Pharm. Sci. 64, 2023–2024 (1975)PubMedCrossRefGoogle Scholar
  126. Polonsky, J.: Quassinoid bitter principles. Fortschr. Chem. Org. Naturst. 30, 101–150 (1973)Google Scholar
  127. Potier, P., Langlois, N., Langlos, Y., Gueritte, F.: Partial synthesis of vin-blastine-type alkaloids. J. Chem. Soc. Chem. Commun. 670–671 (1975)Google Scholar
  128. Powell, R.G., Weisleder, D., Smith, C.R., Jr.: Antitumor alkaloids from Cephalotaxus harringtonia: structure and activity. J. Pharm. Sci. 61, 1227–1230 (1972)PubMedCrossRefGoogle Scholar
  129. Quick, A., Rogers, D.: Crystal and molecular structure of parthenolide. J. Chem. Soc. Perkin Trans. 2, 465–469 (1976)Google Scholar
  130. Regina, M., Sampaio, P., De Oliveira, M.M., Gilbert, B.: Antineoplastic activity of olivacine. Cien. Cult. (Sao Paulo) 26, 517 (1974)Google Scholar
  131. Remillard, S., Rebun, L.I., Howe, G.A., Kupchan, S.M.: Antimitotic activity of the potent tumor inhibitor maytansine. Science 189, 1002–1004 (1975)PubMedCrossRefGoogle Scholar
  132. Richman, J.E.: Total synthesis of camptothecine. Diss. Abstr. Int. 36B, 243 (1975)Google Scholar
  133. Sawa, Y., Ikegawa, T.: 2,3-Substituted-9-hydroxy-10-methoxy-berberinium phosphates. Japan Pat. 75,19,914 (1975). Through Chem. Abstr. 83. 114717hGoogle Scholar
  134. Schaeppi, U., Fleischman, R.W., Cooney, D.A.: Toxicity of camptothecine (NSC-100880). Cancer Chemother. Rep. Pt. 3 5, 25–36 (1974)Google Scholar
  135. Schultz, A.G.: Camptothecin. Chem. Rev. 73, 385–405 (1973)CrossRefGoogle Scholar
  136. Semmelhack, M.F., Chong, B.P., Jones, L.D.: Total synthesis of Cephalotanus alkaloids. J. Am. Chem. Soc. 94, 8629–8630 (1972)PubMedCrossRefGoogle Scholar
  137. Semmelhack, M.F., Chong, B.P., Stauffer, R.D., Rogerson, T.D., Chong, A., Jones, L.D.: Total synthesis of the Cephalotaxus alkaloids. A problem in nucleophilic aromatic substitution. J. Am. Chem. Soc. 97, 2507–2516 (1975)PubMedCrossRefGoogle Scholar
  138. Semmelhack, M.F., Stauffer, R.D., Rogerson, T.D.: Nucleophilic aromatic substation via a new nickel-catalyzed process and via the SRN1 reaction. Improved synthesis of cephalotaxinone. Tetrahedron Lett. 4519–4522 (1973)Google Scholar
  139. Sethi, V.S., Sethi, M.L.: Inhibition of reverse transcripterase activity of RNA-tumor viruses by fagaronine. Biochem. Biophys. Res. Commun. 63, 1070–1076 (1975)PubMedCrossRefGoogle Scholar
  140. Shamma, M., Georgiev, V.St.: Camptotheoine. J. Pharm. Sci. 63, 163–183 (1974)PubMedCrossRefGoogle Scholar
  141. Siddiqui, S., Firat, D., Olshin, S.: Phase II study of emetine (NSC-33669) in the treatment of solid tumors. Cancer Chemother. Rep., Pt. 1 57, 423–428 (1973)Google Scholar
  142. Strauch, R., Hiller, K.: Cancerostatisch wirksame Naturstoffe. Pharmazie 29, 656–670 (1974)PubMedGoogle Scholar
  143. Sugasawa, T., Toyoda, T., Sasakura, K.: Camptothecine. Japan. Koaki 74,117,499 (1974). Through Chem. Abst. 82. 125513uGoogle Scholar
  144. Takahashi, S.: The presence of the tumor inhibitor crotepoxide (futoxide) in Piper futokadzura. Phytochemistry 8, 321–322 (1969)CrossRefGoogle Scholar
  145. Tang, C.S.F., Morrow, C.J., Rapoport, H.: A total synthesis of dl-camptotheeine. J. Am. Chem. Soc. 97, 159–167 (1975)PubMedCrossRefGoogle Scholar
  146. Tin-Wa, M., Bell, C.L., Bevelle, C., Fong, H.H.S., Famsworth, N.R.: Potential anticancer agents I: Confirming evidence for the structure of fagaronine. J. Pharm. ` 63, 1476–1477 (1974)Google Scholar
  147. Tobinaga, S.: Cryptopleurine. Japan. Koaki Patent 75,59,398 (1975). Through Chem. Abstr. 83, 131809gGoogle Scholar
  148. Todorov, D., Damyanova, M.: Acute toxicity of the antitumor alkaloid thaliblastine. Dokl. Bolg. Akad. Nauk 28, 709–711 (1975)Google Scholar
  149. Torrance, S.J., Wiedhopf, R.M., Cole, J.R.: Ambrosin, tumor inhibitory agent from Hymenoclea salsola (Asteraceae). J. Pharm. Sci. 64, 887–888 (1975)PubMedCrossRefGoogle Scholar
  150. Toubiana, R., Mompon, B., Ho, C.M., Toubiana, M.-J.: Isolement du vernodalin et du vernolepin a partir de Vernonia guineensis: authenticite du squellette elemane. Phytochemistry 14, 775–778 (1975)CrossRefGoogle Scholar
  151. Truhaut, R., Dophuoc, H., Cao, T.D., Gak, J.-C., Jacquignon, P., Ba, G.N.: Inhibitory effect of ellipticine on the cancerization of the rat liver induced by BT6: its incidence on the levels of cytochrome P450 and on arginase activity. C. R. Acad. Sci., Paris, Ser. D. 282, 1219–1224 (1976)Google Scholar
  152. Walraven, H.G.M., Pandit, U.K.: A facile two synthon approach to deethyldeoxy-camptothecine. Tetrahedron Lett. 4507–4510 (1975)Google Scholar
  153. Wani, M.C., Taylor, H.L., Wall, M.E.: Plant antitumor agents: colubrinol acetate and colubrinol, antileukemic ansa macrolides from Colubrina texensis. J. Chem. Soc., Chem. Commun. 390 (1973)Google Scholar
  154. Weinreb, S.M., Auerbach, J.: Total synthesis of the Cephalotaxus Alkaloids. Cephalotaxine, cephaloxtaxinone and demethycephalotaxinone. J. Am. Chem. Soc. 97, 2503–2506 (1975)CrossRefGoogle Scholar
  155. Weinreb, S.M., Semmelhack, M.F.: Synthesis of the Cephalotaxus alkaloids. Acc. Chem. Res. 8, 158–164 (1975)CrossRefGoogle Scholar
  156. Weiss, S.G., Tin-Wa, M., Perdue, R.E., Jr., Farnsworth, N.R.: Potential anticancer agents. II.: Antitumor and cytotoxic lignans from Linum album (Linaceae). J. Pharm. Sci. 64, 95–98 (1975)PubMedCrossRefGoogle Scholar
  157. Winterfeldt, E.: Approaches to camptotheeine. Recent Dev. Chem. Nat. Carbon Compd. 6, 9–34 (1975)Google Scholar
  158. Wolpert-Defilippes, M.K., Adamson, R.H., Cysyk, R.L., Johns, D.G.: Initial studies on the cytotoxic action of maytansine, a novel ansa macrolide. Biochem. Pharmaco. 24, 751–754 (1975)CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Berlin Heidelberg 1977

Authors and Affiliations

  • G. A. Cordell

There are no affiliations available

Personalised recommendations