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Abstract

More than ten years have elapsed since the publication of a comprehensive review on the quassinoids, the bitter principles of the Simaroubaceae family (80). Interest in these terpenoids has increased enormously in recent years due in part to the finding of the American National Cancer Institute in the early 1970s that these compounds display marked antileukemic activity. Furthermore, a wide spectrum of other biological properties for the quassinoids has been discovered and studies on chemical modifications of inactive members to yield biologically active ones were undertaken. New structures have been established also and numerous synthetic approaches have been developed which include the total synthesis of the parent compound, quassin (p. 250) and also that of castelanolide (p. 253).

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References

  1. Arisawa, M., A. D. Kinghorn, G. A. Cordell, and N. R. Farnsworth: Plant Anticancer Agents. XXIII. 6α-Senecioyloxy Chaparrin, a New Antileukemic Quassinoid from Simaba multiflora. J. Nat. Prod. 46, 218 (1983).

    Article  CAS  Google Scholar 

  2. Baldwin, M. A., D. M. Carter, F. A. Darwish, and J. D. Phillipson: The Mass Spectral Behaviour of Bruceolides. Biomed. Mass Spectrom. 8, 362 (1981).

    Article  CAS  Google Scholar 

  3. Batt, D. G., N. Takamura, and B. Ganem: General Synthesis of Pentacyclic Quassinoids. J. Amer. Chem. Soc. 106, 3353 (1984).

    Article  CAS  Google Scholar 

  4. Bedikian, A. Y., M. Valdivieso, G. P. Bodey, W. K. Murphy, and E. J. Freireich: Initial Clinical Studies with Bruceantin. Cancer Treat. Rep. 63, 1843 (1979).

    CAS  Google Scholar 

  5. Bhatnagar, S., and J. Polonsky: Conversion of Chaparrin into Quassinoid Analogs. Unpublished results.

    Google Scholar 

  6. Bhatnagar, S., J. Polonsky, T. Prangé, and C. Pascard: New Toxic Quassinoid Glucosides from Simarouba Glauca (X-Ray Analysis). Tetrahedron Lett. 25, 299 (1984).

    Article  CAS  Google Scholar 

  7. Caruso, A. J., J. Polonsky, and B. Soto Rodriguez: Synthetic Studies in the Quassinoid Series. Conversion of Chaparrin into Castelanone and Quassinoid Analogs. Tetrahedron Lett. 23, 2567 (1982).

    Article  Google Scholar 

  8. Casinovi, C. G., P. Ceccherelli, G. Fardella, and G. Grandiloni: Isolation and Structure of a Quassinoid from Ailanthus glandulosa. Phytochemistry 22, 2871 (1983).

    Article  CAS  Google Scholar 

  9. Cassady, J. M., and M. Suffness: Terpenoid Antitumor Agents. In: Anticancer Agents Based on Natural Product Models, p. 254. New York: Academic Press, Inc. 1980.

    Google Scholar 

  10. Chien, M. M., and J. P. Rosazza: Microbial Transformation of Natural Antitumour Agents. Part 15. Metabolism of Bruceantin by Streptomyces griseus. J. C. S. Perkin I, 1352 (1981).

    Google Scholar 

  11. Corey, E. J., and A. Venkateswarlu: Protection of Hydroxyl Groups as tert-Butyldimethylsilyl Derivatives. J. Am. Chem. Soc. 94, 6190 (1972).

    Article  CAS  Google Scholar 

  12. Cuckler, A. C., S. Kuna, C. W. Mushett, R. H. Silber, R. B. Stebbins, H. C. Stoerk, R. N. Arison, F. Cuchie, and C. M. Malanga: Chemotherapeutic and pharmacological studies on glaucarubin, a specific amebacide. Arch. Int. Pharmacodyn. 114, 307 (1958).

    CAS  Google Scholar 

  13. Darise, M., H. Kohda, K. Mizutani, and O. Tanaka: Eurycomanone and Eurycomanol, Quassinoids from the Roots of Eurycoma Longifolia. Phytochemistry 21, 2091 (1982).

    Article  CAS  Google Scholar 

  14. Revision of Configuration of the 12-Hydroxyl Group of Eurycomanone and Eurycomanol, Quassinoids from Eurycoma Longifolia. Phytochemistry 22, 1514 (1983).

    Article  Google Scholar 

  15. Dailey, O. D., and P. L. Fuchs: Synthesis of a Model for the BCE Ring System of Bruceantin. A Caveat on the Cyclohexene→Trans Diaxial Diol Conversion. J. Org. Chem. 45, 216 (1980).

    Article  CAS  Google Scholar 

  16. DE Carneri, I., and C.G. Casinovi: Un potente antiamebico d’origine vegetale: l’ailantone, principio attivo di Ailanthus glandulosa. Parasitologia 10, 215 (1968).

    Google Scholar 

  17. Dias, J. R., and R. Ramachandra: Studies Directed toward Synthesis of Quassinoids. 2. D-Ring cleavage of Cholic Acid Derivatives. J. Org. Chem. 42, 1613 (1977).

    Article  CAS  Google Scholar 

  18. Dias, J. R., and R. Ramachandra: Studies Directed toward Synthesis of Quassinoids. 5. Conversion of D-Ring Seco Derivatives of Cholic Acid to 5-Lactones. J. Org. Chem. 42, 3584 (1977).

    Article  CAS  Google Scholar 

  19. Feuillet, C.: Etudes sur les Simaroubaceae. IL Un Simaba nouveau de Guyane française dans la section Floribundae Engl.: S. morettii. Candollea 38, 745 (1983).

    Google Scholar 

  20. Fong, K. L. L., D. H. W. Ho, R. S. Benjamin, N. S. Brown, A. Y. Bedikian, B. S. Yap, C. L. Wiseman, W. Kramer, and G. P. Bodey: Clinical Pharmacology of Bruceantin by Radioimmunoassay. Cancer Chemother. Pharmacol. 9, 169 (1982).

    Article  CAS  Google Scholar 

  21. Fukumoto, K., M. Chihiro, Y. Shiratori, M. Ihara, T. Kametani, and T. Honda: An Intramolecular Diels-Alder Approach to Quassinoids — A Stereoselective Construction of A Aromatic Klaineanone. Tetrahedron Lett. 23, 2973 (1982).

    Article  CAS  Google Scholar 

  22. Fukumoto, K., M. Chihiro, M. Ihara, T. Kamet Ani, and T. Honda: A New Synthetic Approach to Quassinoids via an Intramolecular Diels-Alder Reaction: A Stereoselective Construction of the Klaineanone Ring System. J. Chem. Soc. (London). Perkin Trans. I, 2569 (1983).

    Article  Google Scholar 

  23. Furuno, T., H. Naora, T. Murae, H. Hirota, T. Tsuyuki, T. Takahashi, A. Itai, Y. Iitaka, and K. Matsushita: Structure of Shinjulactone B, A New Bitter Principle from Ailanthus altissima. Chemistry Lett. 1797 (1981).

    Google Scholar 

  24. Gillin, F. D., and D. S. Reiner: In vitro Activity of Certain Quassinoid Antitumor Agents against Entamoeba histolytica. Arch. Invest. Med. 13 (Suppl. 3), 43 (1982).

    CAS  Google Scholar 

  25. Gillin, F. D., D. S. Reiner, and M. Suffness: Bruceantin, a Potent Amebicide from a Plant, Brucea antidysenterica. Antimicrob. Agents Chemother. 22(2), 342 (1982).

    CAS  Google Scholar 

  26. Grieco, P. A., S. Ferriño, and G. Vidari: Total Synthesis of dl-Quassin. J. Amer. Chem. Soc. 102, 7586 (1980).

    Article  CAS  Google Scholar 

  27. Grieco, P. A., R. Lis, S. Ferrino, and J. Y. Jaw: Synthetic Studies on Quassinoids: Total Synthesis of dl-Castelanolide. J. Org. Chem. 47, 601 (1982).

    Article  CAS  Google Scholar 

  28. Hall, I. H., Y. F. Liou, M. Okano, and K. H. Lee: Antitumor Agents Xlvi: In vitro Effects of Esters of Brusatol, Bisbrusatol, and Related Compounds on Nucleic Acid and Protein Synthesis of P-388 Lymphocytic Leukemia Cells. J. Pharm. Sci. 71, 345 (1982).

    Article  CAS  Google Scholar 

  29. Hall, I. H., K. H. Lee, Y. Imakura, M. Okano, and A. Johnson: Anti-Inflammatory Agents III: Structure-Activity Relationships of Brusatol and Related Quassinoids. J. Pharm. Sci. 72, 1282 (1983).

    Article  CAS  Google Scholar 

  30. Handa, S. S., A. D. Kinghorn, G. A. Cordell, and N. R. Farnsworth: Plant Anticancer Agents XXV. Constituents of Soulamea Soulameoides. J. Nat. Prod. 46, 359 (1983).

    Article  CAS  Google Scholar 

  31. Hikino, H., T. Ohta, and T. Takemoto: Picrasins, Simaroubolides of Japanese Quassia Tree Picrasma Quassinoides. Phythochemistry 14, 2473 (1975).

    Article  CAS  Google Scholar 

  32. Honda, T., T. Murae, S. Ohta, Y. Kurata, H. Kawai, T. Takahashi, A. Itai, and Y. Iitaka: Synthesis of (±)-3,3-Ethylenedioxy-14α-Hydroxy-5-Picrasene-11,16-Dione, A 14α-H-Picrasane Derivative. Chemistry Lett. 299 (1981).

    Google Scholar 

  33. Ishibashi, M., T. Murae, H. Hirota, H. Naora, T. Tsuyuki, T. Takahashi, A. Itai, and Y. Iitaka: Shinjudilactone, a New Bitter Principle from Ailanthus Altissima Swingle. Chemistry Lett. 1597 (1981).

    Google Scholar 

  34. Ishibashi, M., T. Murae, H. Hirota, T. Tsuyuki, T. Takahashi, A. Itai, and Y. Iitaka: Shinjulactone C, a New Quassinoid with a lα,12α:5α,13α-Dicyclo-9β H-Picrasane Skeleton from Ailanthus Altissima Swingle. Tetrahedron Lett. 1205 (1982).

    Google Scholar 

  35. Ishibashi, M., T. Tsuyuki, T. Murae, and T. Takahashi: Conversion of Ailanthone into Shinjudilactone, a Backbone-Rearranged Picrasane. Chem. Pharm. Bull. 30 (5), 1917 (1982).

    Article  Google Scholar 

  36. Ishibashi, M., T. Tsuyuki, and T. Takahashi: Conversion of Ailanthone into Shinjulactone C through an Ionic (4+2) Cycloaddition Reaction. Tetrahedron Lett. 4843 (1983).

    Google Scholar 

  37. Ishibashi, M., T. Tsuyuki, T. Murae, H. Hirota, T. Takahashi, A. Itai, and Y. Iitaka: Constituents of the Root Bark of Ailanthus altissima Swingle. Isolation and X-Ray Crystal Structures of Shinjudilactone and Shinjulactone C and Conversion of Ailanthone into Shinjudilactone. Bull. Chem. Soc. Jpn. 56, 3683 (1983).

    Article  CAS  Google Scholar 

  38. Ishibashi, M., S. Yoshimura, T. Tsuyuki, T. Takahashi, A. Itai, Y. Iitaka, and K. Matsushita: Shinjulactone F, a New Bitter Principle with a 5βH-Picrasane Skeleton from Ailanthus Altissima Swingle. Chemistry Lett. 555 (1984).

    Google Scholar 

  39. Keshavamurthy, K. S., Y. D. Vankar, and D. N. Dhar: Preparation of Acid Anhydrides, Amides and Esters Using Chlorosulfonyl Isocyanate as a Dehydrating Agent. Synthesis 506 (1982).

    Google Scholar 

  40. Khan, S. A., B. I. Fozdar, and K. M. Shamsuddin: Quassinoids from Ailanthus malabarica. Indian J. Chem. Sect. B 21B(12), 1133 (1982).

    CAS  Google Scholar 

  41. Khan, S. A., S. S. Zuberi, and K. M. Shamsuddin: Isolation and Structure of Excelsin, a New Quassinoid from Ailanthus excelsa. Indian J. Chem. 19B, 183 (1980).

    CAS  Google Scholar 

  42. Khôi, N., and J. Polonsky: Structural Modifications of Chaparrinone Using Benezeneseleninic Anhydride. Helv. Chim. Acta 64, 1540 (1981).

    Article  Google Scholar 

  43. Koch, H. J., H. Pfenninger, and W. Graf: Quassinoid Bitterstoffe I 1-Oxo-2-methoxy 4α-methyl-17β-hydroxy-Δ2-5α-androsten als Modell für den Ring A des Quassins. Helv. Chim. Acta 58, 1727 (1975).

    Article  CAS  Google Scholar 

  44. Kraus, G. A., and M. J. Taschner: Model Studies for the Synthesis of Quassinoids. 1. Construction of the BCE Ring System. J. Org. Chem. 45, 1175 (1980).

    Article  CAS  Google Scholar 

  45. Kraus, G. A., M. Tachner, and M. Shimagaki: An Approach to the BCDE Ring of Quasimarin. J. Org. Chem. 47, 4271 (1982).

    Article  CAS  Google Scholar 

  46. Kupchan, S. M., R. W. Britton, J. A. Lacadie, M. F. Ziegler, and C. W. Sigel: The Isolation and Structural Elucidation of Bruceantin and Bruceantinol, New Potent Antileukemic Quassinoids from Brucea antidysenterica. J. Org. Chem. 40, 648 (1975).

    Article  CAS  Google Scholar 

  47. Kupchan, S. M., and J. A. Lacadie: Dehydroailanthinone, a New Antileukemic Quassinoid from Pierreodendron kerstingii. J. Org. Chem. 40, 654 (1975).

    Article  CAS  Google Scholar 

  48. Kupchan, S. M., J. A. Lacadie, G. A. Howie, and B. R. Sickles: Structural Requirements for Biological Activity among Antileukemic Glaucarubolone Ester Quassinoids. J. Med. Chem. 19, 1130 (1976).

    Article  CAS  Google Scholar 

  49. Kupchan, S. M., and D. R. Streelman: Quassimarin, a New Antileukemic Quassinoid from Quassia amara. J. Org. Chem. 41, 5481 (1976).

    Google Scholar 

  50. Lee, K. H.: Bruceolides. U.S. Patent 4, 350, 638 (1982).

    Google Scholar 

  51. Lee, K. H., Y. Imakura, Y. Sumida, R. Y. Wu, J. H. Hall, and H. Ch. Huang: Antitumor Agents. 33. Isolation and Structural Elucidation of Bruceoside-A and-B, Novel Antileukemic Quassinoid Glycosides, and Brucein-D and-E from Bruceajavanica. J. Org. Chem. 44, 2180 (1979).

    Article  CAS  Google Scholar 

  52. Lee, K. H., M. Okano, I. H. Hall, D. A. Brent, and B. Soltmann: Antitumor Agents XIV: Bisbrusatolyl and Brusatolyl Esters and Related Compounds as Novel Potent Antileukemic Agents. J. Pharm. Sci. 71, 338 (1982).

    Article  CAS  Google Scholar 

  53. Leskinen, V., J. Polonsky, and S. Bhatnagar: Antifeedant Activity of Quassinoids. J. Chem. Ecol. 10, 1497 (1984).

    Article  CAS  Google Scholar 

  54. LE-Van-Thoi, and Nguyên-Ngoc-Suong: Constituents of Eurycoma longifolia Jack. J. Org. Chem. 35, 1104 (1970).

    Article  Google Scholar 

  55. Liao, L. L., S. M. Kupchan, and S. B. Horwitz: Mode of Action of the Antitumor Compound Bruceantin, an Inhibitor of Protein Synthesis. Mol. Pharmacol. 12, 167 (1976).

    CAS  Google Scholar 

  56. Liesmann, J., R. J. Belt, C. D. Haas, and B. Hoogstraten: Phase I Study on Bruceantin Administered on a Weekly Schedule. Cancer Treat. Rep. 65, 883 (1981).

    CAS  Google Scholar 

  57. Lumonadio, L., and M. Vanhaelen: Canthin-6-one, Undulatone and two New Quassinoids from Hannoa klaineana Roots. Phytochemistry 23, 2121 (1984).

    Article  CAS  Google Scholar 

  58. Mandel, L., D. E. Lee, and L. F. Courtney: Toward the Total Synthesis of Quassin. J. Org. Chem. 47, 610 (1982).

    Article  Google Scholar 

  59. Mai Van Tri, J. Polonsky, C. Merienne, and T. Sevenet: Soularubinone, a New Antileukemic Quassinoid from Soulamea tomentosa. J. Nat. Products 44, 279 (1981).

    Article  Google Scholar 

  60. Monseur, X., and J. C. Motte: Quantitative high performance liquid Chromatographic analysis of the bitter quassinoid compounds from Simaruba glauca seeds. J. Chromat. 264, 469 (1983).

    Article  CAS  Google Scholar 

  61. Moretti, C., J. Polonsky, M. Vuilhorgne, and T. Prange: Isolation and Structure of Sergeolide, a Potent Cytotoxic Quassinoid from Picrolemma pseudocoffea. Tetrahedron Lett. 23, 647 (1982).

    Article  CAS  Google Scholar 

  62. Moron, J., and J. Polonsky: Sur l’origine triterpénique des constituants amers des Simarubacées. Tetrahedron Lett. 385 (1968).

    Google Scholar 

  63. Murae, T., A. Sugie, T. Tsuyuki, S. Masuda, and T. Takahashi: Bitter Principles of Picrasma ailanthoides Planchon Nigakilactones J, K, L, M, and N. Tetrahedron 29, 1515 (1973).

    Article  CAS  Google Scholar 

  64. Murae, T., and T. Takahashi: Conversion of Quassin into 15β-[(E)-3,4-Dimethyl-2-pentenoyloxy]quassin. A D-Ring Analog of Bruceantin. Bull. Chem. Soc. Jpn. 54, 941 (1981).

    Article  CAS  Google Scholar 

  65. Naora, H., T. Furuno, M. Ishibashi, T. Tsuyuki, T. Takahashi, A. Itai, Y. Iitaka, and J. Polonsky: On the Structure of Ailanthone, a Bitter Principle from Ailanthus Altissima. Chemistry Letters 661 (1982).

    Google Scholar 

  66. Naora, H., M. Ishibashi, T. Furuno, T. Tsuyuki, T. Murae, H. Hirota, T. Takahashi, A. Itai, and Y. Iitaka: Structure Determination of Bitter principles in Ailanthus altissima. Structure of Shinjulactone A and Revised Structure of Ailanthone. Bull. Chem. Soc. Jpn. 56, 3694 (1983).

    Article  CAS  Google Scholar 

  67. Nestler, T., G. Tittel, and H. Wagner: Quantitative Bestimmung der Bitter Quassinoide von Quassia amara und Picrasma excelsa. Planta Medica 38, 204 (1980).

    Article  CAS  Google Scholar 

  68. Nguyên-Ngoc-Suong, S. Bhatnagar, J. Polonsky, M. Vuilhorgne, T. Prange, and C. Pascard: Structure of Laurycolactone A and B, New C18-Quassinoids from Eurycoma Longifolia and revised Structure of Eurycomalactone (X-Ray analysis). Tetrahedron Lett. 5159 (1982).

    Google Scholar 

  69. Nicolaou, K. C., and Z. Lysenko: Phenylselenolactonization. An Extremely Mild and Synthetically Useful Cyclization Process. J. Am. Chem. Soc. 99, 3185 (1977).

    Article  CAS  Google Scholar 

  70. Odjo, A., J. Piart, J. Polonsky, and M. Roth: Etude de l’effet insecticide de deux quassinoïdes sur des larves de Locusta migratoria migratorioides R et F (Orthoptera, Acrididae). C. R. Acad. Sci. Paris 293, Série III, 241 (1981).

    CAS  Google Scholar 

  71. Oei-Koch, A., and LJ. Kraus: Inhaltsstoffe von Eurycoma Longifolia JACK III. Bitterstoff (Eurycomalacton). Sci. Pharm. 48, 110 (1980).

    CAS  Google Scholar 

  72. Okano, M., T. Fujita, N. Fukamiya, and T. Aratani: New Quassinoid Glycosides and Hemiacetals from Picrasma Ailanthoides Planchon. Picrasinoside-B,-C,-D,-E,-F, and-G, and Picrasinol-A and-B. Chemistry Lett. 221 1984).

    Google Scholar 

  73. Okano, M., N. Fukamiya, K. Kondo, T. Fujita, and T. Aratani: Picrasinoside-A, A Novel Quassinoid Glucoside from Picrasma Ailanthoides Planchon. Chemistry Lett. 1425 (1982).

    Google Scholar 

  74. Okano, M., and K. H. Lee: Antitumor Agents. 43. Conversion of Bruceoside-A into Bruceantin. J. Org. Chem. 46, 1138 (1981).

    Article  CAS  Google Scholar 

  75. Okano, M., K. H. Lee, I. H. Hall, and F. E. Boettner: Antitumor Agents. 39. Bruceantinoside-A and-B, Novel Antileukemic Quassinoid Glucosides from Brucea Antidysenterica. J. Nat. Prod. 44, 470 (1981).

    Article  CAS  Google Scholar 

  76. Pascard, C., T. Prangé, and J. Polonsky: Crystal and Molecular Structure of the Quassinoid 6-Hydroxypicrasin B. J. Chem. Res. (S) 324 (1977).

    Google Scholar 

  77. Pfenninger, J., and W. Graf: Quassinoide Bitterstoffe II Partialsynthetischer Zugang zu Quassin: Überführung von Testosteron in eine Schlüsselverbindung mit angularer 8β-Methylgruppe. Helv. Chim. Acta 63, 1562 (1980).

    Article  CAS  Google Scholar 

  78. Phillipson, J. D., and F. A. Darwish: TLX-5 Lymphoma Cells in Rapid Screening for Cytotoxicity in Brucea Extracts. Planta Med. 35, 308 (1979).

    Article  CAS  Google Scholar 

  79. Phillipson, J. D., and F. A. Darwish: Bruceolides from Fijian Brucea Javanica. Planta Med. 41, 209 (1981).

    Article  CAS  Google Scholar 

  80. Pierré, A., M. Robert-Gero, C. Tempete, and J. Polonsky: Structural Requirements of Quassinoids for the Inhibition of Cell Transformation. Biochem. Biophys. Res. Comm. 93, 675 (1980).

    Article  Google Scholar 

  81. Polonsky, J.: Quassinoid Bitter Principles. In: Fortschr. Chem. Organ. Naturstoffe Vol.30 (L. Zechmeister, ed.), p. 101. Wien-New York: Springer. 1973.

    Google Scholar 

  82. —Chemistry and Biological Activity of the Quassinoids. In: The Chemistry and Chemical Taxonomy of the Rutales (P. G. Waterman and M. F. Grundon, ed.), p. 247. New York: Academic Press. 1983.

    Google Scholar 

  83. Polonsky, J., Z. Baskevitch, A. Gaudemer, and B.C. Das: Constituants amers de Brucea amarissima: structures des brucéines A, B, et C. Experientia 23, 427 (1967).

    Article  Google Scholar 

  84. Polonsky, J., Z. Baskevitch, H. E. Gottlieb, E. W. Hagaman, and E. Wenkert: Carbon-13 Nuclear Magnetic Resonance Spectral Analysis of Quassinoid Bitter Principles. J. Org. Chem. 40, 2499 (1975).

    Article  CAS  Google Scholar 

  85. Polonsky, J., Z. Baskevitch, Z. Varon, and T. Sevenet: Constituants amers de Soulamea foment osa (Simaroubaceae). Structure d’un nouveau quassinoide, l’isobrucéine A. Experientia 31, 1113 (1975).

    CAS  Google Scholar 

  86. Polonsky, J., S. Bhatnagar, and C. Moretti: 15-Deacetylsergeolide, a Potent Antileukemic Quassinoid. J. Nat. Prod. 47, 994 (1984).

    Article  CAS  Google Scholar 

  87. Polonsky, J., S. Bhatnagar, and C. Moretti: Deacetylsimarolide, a new C25 quassinoid from Simaba morettii. Unpublished results.

    Google Scholar 

  88. Polonsky, J., J. Gallas, J. Varenne, T. Prangé, C. Pascard, H. Jacquemin, and C. Moretti: Isolation and Structure (X-Ray Analysis) of Karinolide, A New Quassinoid from Simaba multiflora. Tetrahedron Lett. 869 (1982).

    Google Scholar 

  89. Polonsky, J., Mai Vantri, T. Prangé, and C. Pascard: Isolation and Structure (X-Ray Analysis) of a New C25 Quassinoid Soulameolide from Soulamea tomentosa. J. C. S. Chem. Comm. 641 (1979).

    Google Scholar 

  90. Polonsky, J., Mai Van Tri, Z. Varon, T. Prangé, C. Pascard, T. Sevenet, and J. Pusset: Quassinoids. Isolation from Soulamea muelleri and Structures of 1,12-Di-O-Acetyl Soulameanone and ′2-Picrasin B, X-Ray Analysis of Soulameanone. Tetrahedron 36, 2983 (1980).

    Article  CAS  Google Scholar 

  91. Polonsky, J., J. Varenne, T. Prangé, and C. Pascard: Antileukaemic Quassinoids: Structure (X-Ray Analysis) of Bruceine C and Revised Structure of Bruceantinol. Tetrahedron Lett. 21, 1853 (1980).

    Article  CAS  Google Scholar 

  92. Polonsky, J., Z. Varon, H. Jacquemin, and G. R. Pettit: The Isolation and Structure of 13,18-Dehydroglaucarubinone, a new antineoplastic quassinoid from Simarouba amara. Experientia 34, 1122 (1978).

    Article  CAS  Google Scholar 

  93. Polonsky, J., Z. Varon, C. Moretti, G. R. Pettit, C. L. Herald, J. Rideout, S. B. Saha, and H. N. Khastgir: The Antineoplastic Quassinoids of Simaba Cuspidata Spruce and Ailanthus Grandis Prain. J. Nat. Prod. 43, 503 (1980).

    Article  CAS  Google Scholar 

  94. Polonsky, J., Z. Varon, T. Prange, C. Pascard, and C. Moretti: Structures of Simarinolide and Guanepolide (X-Ray Analysis). New Quassinoids from Simaba cf Orinocensis. Tetrahedron Lett. 22, 3605 (1981).

    Article  CAS  Google Scholar 

  95. Polonsky, J., Z. Varon, and E. Soler: Constituants amers de Castela tweedii (Simaroubaceae). Structure d’un nouveau quassinoide, la Castelanone. Compt. Rend. Acad. Sa, Série C 288, 269 (1979).

    CAS  Google Scholar 

  96. Robins, R. J., M. R. A. Morgan, M. J. C. Rhodes, and J. M. Furze: An Enzyme Linked Immunosorbent Assay for Quassin and Closely Related Metabolites. Anal. Biochem. 136, 145 (1984).

    Article  CAS  Google Scholar 

  97. Robins, R. J., and M. J. C. Rhodes: High-performance liquid Chromatographic methods for the analysis and purification of quassinoids from Quassia amara L. J. Chromat. 283, 436 (1984).

    Article  CAS  Google Scholar 

  98. Robins, R. J., M. R. A. Morgan, M. J. C. Rhodes, and J. M. Furze: Determination of Quassin in Picogram Quantities by an Enzyme-Linked Immunosorbent Assay. Phytochemistry 23, 1119 (1984).

    Article  CAS  Google Scholar 

  99. Seida, A., A. D. Kinghorn, G. A. Cordell, and N. Farnsworth: Potential Anticancer agents. IX. Isolation of a New Simaroubolide, 6α-Tigloyloxychaparrinone from Ailanthus integrifolia ssp. calcyna (Simaroubaceae). J. Nat. Prod. 41, 584 (1978).

    CAS  Google Scholar 

  100. Shishido, K., T. Saitoh, and R. Fukumoto: A New Synthetic Approach to Bruceantin via an Intramolecular Diels-Alder Reaction: Stereoselective Construction of the Pentacyclic Model System. J. Chem. Soc. Perkin Trans I, 2139 (1984).

    Article  Google Scholar 

  101. Stojanac, N., A. Sood, Z. Stojanac, and Z. Valenta: A Synthetic Approach to Quassin. Introduction of Functionality and Stereochemistry by a Diels-Alder Reaction. Can. J. Chem. 53, 619 (1975).

    Article  CAS  Google Scholar 

  102. Stojanac, N., Z. Stojanac, P. S. White, and Z. Valenta: A Synthetic Approach to Quassin. Synthesis of a Ring A seco Derivative. Can. J. Chem. 57, 3346 (1979).

    Article  CAS  Google Scholar 

  103. Suling, W. J., C. W. Woolley and W. M. Shannon: Disposition and Metabolism of Bruceantin in the Mouse. Cancer Chemother. Pharmacol. 3, 171 (1979).

    Article  CAS  Google Scholar 

  104. Trager, W., and J. Polonsky: Antimalarial Activity of Quassinoids against Chloroquine-Resistant Plasmodium falciparum in vitro. Am. J. Trop. Med. Hyg. 30(3), 531 (1981).

    CAS  Google Scholar 

  105. Vedejs, E., D. A. Engler, and J. E. Telschow: Transition-Metal Peroxide Reactions. Synthesis of α-Hydroxycarbonyl Compounds from Enolates. J. Org. Chem. 43, 188 (1978).

    Article  CAS  Google Scholar 

  106. Veysoglu, T., and L. A. Mitcher: A Class of New Silylating Reagents. I. A Mild Method for Introduction of the Tert-Butyldimethylsilyl Group. Tetrahedron Lett. 22, 1299 (1981).

    Article  CAS  Google Scholar 

  107. Voyle, M., N. K. Dunlap, D. S. Watt, and O. P. Anderson: Quassinoids. 2. Synthesis of an ABCD Ring Precursor Involving a Lactonization Induced by lodotrimethylsilane. J. Org. Chem. 48, 3242 (1983).

    Article  CAS  Google Scholar 

  108. Voyle, M., K. S. Kyler, S. Arseniyadis, N. D. Dunlap, and D. S. Watt: Quassinoids. 1. Attempted Intramolecular Diels-Alder Approach for Assembling the ABCD Rings. J. Org. Chem. 48, 470 (1983).

    Article  CAS  Google Scholar 

  109. Wall, M. E., and M. C. Wani: Plant Antitumor Agents. 17. Structural Requirements for Antineoplastic Activity in Quassinoids. J. Med. Chem. 21, 1186 (1978).

    Article  CAS  Google Scholar 

  110. Wani, M. C., H. L. Taylor, J. B. Thompson, M. E. Wall, A. T. Mcphail, and K. D. Onan: Plant Antitumour Agents. XV. Isolation and X-Ray Crystal Structure of a New Antileukaemic Quassinoid Undulatone from Hannoa Undulata. Tetrahedron 35, 17 (1979).

    Article  CAS  Google Scholar 

  111. Wani, M. C., H. L. Taylor, J. B. Thompson, and M. E. Wall: Plant Antitumor Agents. XVI. 6α-Senecioyloxychaparrinone, a New Antileukemic Quassinoid from Simaba multiflora. J. Nat. Prod. 41, 578 (1978).

    CAS  Google Scholar 

  112. Wani, M. C., H. L. Taylor, M. E. Wall, A. T. Mcphail, and K. D. Onan: Plant Antitumour Agents: Isolation and Structure of Samaderine A (X-Ray Analysis) and a New Antileukaemic Quassinoid Samaderine E from Samadera indica. J. C. S. Chem. Comm. 295 (1977).

    Google Scholar 

  113. Waterman, P. G., S. A. Ampoho: Cytotoxic Quassinoids from Odyendyea gabonensis Stem Bark; Isolation and High-Field NMR. Planta Medica 50, 261 (1984).

    Article  CAS  Google Scholar 

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Polonsky, J. (1985). Quassinoid Bitter Principles II. In: Herz, W., Grisebach, H., Kirby, G.W., Tamm, C. (eds) Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, vol 47. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8790-6_4

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