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Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles pp 83–166Cite as

The Chemistry of Podophyllum

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Abstract

Podophyllum is the dried roots and rhizomes of species of Podophyllum (Fam. Berberidaceae). It is derived commercially from two species of plants, namely, Podophyllum peltatum L., the American species, and P. emodi Wall. (P. hexandrum Royle), the Indian. Both are herbaceous perennials. The species do not have an ancient history compared with that of many other medicinal plants. P. peltatum is indigenous to the United States and Canada and grows commonly in eastern North America from Quebec through Florida and westward to Minnesota and Texas. It is usually called in the United States “May apple” or “American mandrake”; older names are “Indian apple”, “wild lemon”, “duck’s foot”, “vegetable calomel”, etc.

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References

  1. Algire, G. H, F.Y. Legallais and B.F. Anderson: Vascular Reactions of Normal and Malignant Tissues in vivo. VI. Components of Podophyllin on Transplanted Sarcomas. J. Nat. Cancer Inst. 14, 879 (1954).

    CAS  Google Scholar 

  2. Barter, J., H. Potěšilova, V. Masinová und F. Šantavy: Isolierung einiger Substanzen aus Résina podophylli (Podophyllum peltatum L.) und Beitrag zu ihrer Konstitution. Chem. Listy 49, 1550 (1955)

    Google Scholar 

  3. Barter, J., H. Potěšilova, V. Masinová und F. Šantavy: Isolierung einiger Substanzen aus Résina podophylli (Podophyllum peltatum L.) und Beitrag zu ihrer Konstitution. Collect. Czech. Chem. Communs. 21, 392 (1956).

    Google Scholar 

  4. Barter, J. und F. Šantavý: Vorläufige Mitteilung. Konstitutionsfrage von α- und β-Peltatin. Chem. Listy 48, 917 (1954).

    Google Scholar 

  5. Bass, C.C.: Private communication.

    Google Scholar 

  6. Belrin, M.: Effect of Podophyllin on Transplanted Mouse Tumors. Fédérat. Proc. (Amer. Soc. exp. Biol.) 6, 308 (1947).

    Google Scholar 

  7. Belkin, M., A. Perrault and M.J. Shear: Tumor-Necrotizing Polysaccharides from Plant Tissues. Proc. Amer. Assoc. Cancer Res. 2(No. 1), 4 (1955).

    Google Scholar 

  8. Bergius, P.J.: Materia Medica e Regno Vegetabili. Stockholm: P. Hesselberg. 1778.

    Google Scholar 

  9. Bohn, W.: Die Heilwerte heimischer Pflanzen, 5. Aufl. Leipzig: Ronniger. 1935.

    Google Scholar 

  10. Borsche, W. und J. Niemann: Über Podophyllin. Liebigs Ann. Chem. 494, 126 (1932).

    CAS  Google Scholar 

  11. — Über Podophyllin. II. Liebigs Ann. Chem. 499, 59 (1932).

    CAS  Google Scholar 

  12. — Über Podophyllin. Ber. dtsch. chem. Ges. 65, 1633 (1932).

    Google Scholar 

  13. — Zur Konstitution des Podophyllotoxins und Pikro-podophyllins. Ber. dtsch. chem. Ges. 65, 1846 (1932).

    Google Scholar 

  14. — Über Podophyllin. III. Liebigs Ann. Chem. 502, 264 (1933).

    CAS  Google Scholar 

  15. Bostock, J. and H.T. Riley: Plinius Secundus, C. (Pliny the Elder) “Natural History”. London: Bohn. 1855.

    Google Scholar 

  16. Bougault, J.: Action de l’acide hypoiodeux naissant sur les acides non saturés. Lactones iodées. Ann. Chim. Phys. [8], 14, 145 (1908).

    Google Scholar 

  17. — Action de l’acide hypoiodeux naissant sur les acides non saturés. Acide oc-cyclogéranique. Ann. Chim. Phys. [8], 22, 125 (1911).

    CAS  Google Scholar 

  18. — British Pharmacopoeia. London: The Pharmaceutical Press. 1948; 1953.

    Google Scholar 

  19. Campbell, K.N., J.A. Cella and B.K. Campbell: Chemotherapy of Cancer. III. The Synthesis of Dihydroxytetrahydronaphthoic Acids Related to Podophyllotoxin. J. Amer. Chem. Soc. 75, 4681 (1953).

    CAS  Google Scholar 

  20. Catesby, M.: Natural History of Carolina, Florida and the Bahama Islands, Vol. I, p. 24. London. 1731.

    Google Scholar 

  21. Charravarti, S.C. and D.P. Charraborty: Chemical Examination of Podophyllum emodi WALL. var. hexandrum (ROYLE). J. Amer. Pharmaceut. Assoc., Sci. Ed. 43, 614 (1954).

    Google Scholar 

  22. Champlain, S. de: The Works of Samuel de Champlain (H.P. Biggar, ed.), Vol. III, p. 50; Vol. IV, p. 241. Quebec: Champlain Soc. 1929.

    Google Scholar 

  23. Chatterjee, R.: Indian Podophyllum. Econ. Botany (New York) 6, 342 (1952) [Chem. Abstr. 47, 705 (1953)].

    CAS  Google Scholar 

  24. — Private communication.

    Google Scholar 

  25. Chatterjee, R. and S.C. Charravarti: A Revision of the Structure of Podophyllotoxin and Picropodophyllin. Science and Culture (India) 17, 136 (1951) [Chem Abstr. 47, 8711 (1953)].

    CAS  Google Scholar 

  26. — Structures of Epipodophyllotoxin and Epipicropodophyllin. Science and Culture (India) 18, 197 (1952) [Chem. Abstr. 47, 9315 (1953)].

    CAS  Google Scholar 

  27. Chatterje, R. and S.C. Chakravarti: Resin sikkimensis. I. Sikkimotoxin: a Lactone from Podophyllum sikkimensis R. Chatterjee et Mukerjee. J. Amer. Pharmaceut. Assoc, Sci. Ed. 41, 415 (1952).

    Google Scholar 

  28. Chatterjee, R. and D.K. Datta: Podophyllum. II. The Colouring Matters of P. sikkimensis R. Chatterjee et S.K. Mukerjee. Indian J. Physiol. Allied Sci. 4, 61 (1950).

    CAS  Google Scholar 

  29. Chatterjee, R. and S.K. Mukerjee: Podophyllum. I. Indian J. Physiol. Allied Sci. 4, 7 (1950).

    Google Scholar 

  30. Cisney, M.E., W.L. Shilling, W.M. Hearon and D.W. Goheen: Conidendrin. II. The Stereochemistry and Reactions of the Lactone Ring. J. Amer. Chem. Soc. 76, 5083 (1954).

    CAS  Google Scholar 

  31. Clapp, A.: A Synopsis: or Systematic Catalogue of the Indigenous and Naturalized, Flowering and Filicoid Medicinal Plants of the United States. Trans. Amer. Med. Assoc. 5, 689 (1852).

    Google Scholar 

  32. Cockayne, O.: Leech Book of Bald. In: Leechdoms, Wortcunnings, and Starcraft of Early England, Vol. II. London: Longman. 1865.

    Google Scholar 

  33. Cole, A.R.H.: Infrared Spectra of Natural Products. Fortschr. Chem. organ. Naturstoffe 13, 1 (1956).

    CAS  Google Scholar 

  34. Coles, W.: Adam in Eden, or Nature’s Paradise. The History of Plants, Fruits, Herbs, and Flowers. London: Brooke. 1657.

    Google Scholar 

  35. Cornman, I.: Inhibition of Arbacia Egg Cleavage by Podophyllotoxin and Related Substances. (Abstract.) Biol. Bull. (Marine Biol. Lab., Woods Hole, Mass.) 93, 192 (1947).

    CAS  Google Scholar 

  36. Cram, D.J.: Olefin Forming Elimination Reactions. In: M.S. Newman, Steric Effects in Organic Chemistry, p. 304. New York: John Wiley. 1956.

    Google Scholar 

  37. Culpepper, N.: The English Physitian Enlarged. London: Sawbridge. 1681.

    Google Scholar 

  38. De-Ambrosi, L.: Metodo rapido di estrazione délia podofillotossina dalla résina del “Podophyllum emody”. Il Farmaco, Ed. pratica 9, 265 (1954) [Chem. Abstr. 48, 10299 (1954)].

    CAS  Google Scholar 

  39. Dohme, A.R.L. and H. Engelhardt: The Fatty Oil of Mandrake (Podophyllum peltatum). Proc. Amer. Pharmaceut. Assoc. 52, 340 (1904).

    Google Scholar 

  40. Drake, N.L. and E.H. Price: Podophyllotoxin and Picropodophyllin. I. Their Reduction by Lithium Aluminum Hydride. J. Amer. Chem. Soc. 73, 201 (1951).

    CAS  Google Scholar 

  41. Drake, N.L. and W.B. Tuemmler: Podophyllotoxin and Picropodophyllin. II. The Synthesis of an Open-Chain Analog. J. Amer. Chem. Soc. 77, 1204 (1955).

    CAS  Google Scholar 

  42. — Podophyllotoxin and Picropodophyllin. III. The Synthesis of a Stripped Analog. J. Amer. Chem. Soc. 77, 1209 (1955).

    CAS  Google Scholar 

  43. Dunstan, W.R. and T.A. Henry: A Chemical Investigation of the Constituents of Indian and American Podophyllum (Podophyllum emodi and Podophyllum peltatum). J. Chem. Soc. (London) 73, 209 (1898).

    CAS  Google Scholar 

  44. Eder, R. und W. Schneiter: Wertbestimmung des Podophyllins. Pharmaceut. Acta Helvet. I, 15 (1926).

    Google Scholar 

  45. Eisenmann: Über die locale Wirkung der Sabina. Virchow’s Arch, pathol. Anat. Physiol. 18, 171 (1860).

    Google Scholar 

  46. Erdtman, H.: Die Konstitution der Harzphenole und ihre biogenetischen Zusammenhänge. II. Über Pinoresinol und seine Beziehungen zu Eudesmin. Liebigs Ann. Chem. 516, 162 (1935).

    CAS  Google Scholar 

  47. — Lignans. In: K. Paech und M.V. Tracey, Moderne Methoden der Pflanzenanalyse, Bd. III, S. 428. Berlin: Springer-Verlag. 1955.

    Google Scholar 

  48. Fenton, W.N.: Contacts Between Iroquois Herbalism and Colonial Medicine. Smithsonian Report for 1941, Publ. 3670, 503 (1942).

    Google Scholar 

  49. Fitzgerald, D.B., J.L. Hartwell and J. Leiter: Distribution of Tumor-Damaging Lignans among Conifers. J. Nat. Cancer Inst. 18, 83 (1957).

    CAS  Google Scholar 

  50. Friedel, R.A. and M. Orchin: Ultraviolet Spectra of Aromatic Compounds, p. 17. New York: John Wiley. 1951.

    Google Scholar 

  51. Geissman, T.A.: Anthocyanins, Chalcones, Aurones, Flavones and Related Water-Soluble Plant Pigments. In: K. Paech und M.V. Tracey, Moderne Methoden der Pflanzenanalyse, Bd. III, S. 450. Berlin: Springer-Verlag. 1955.

    Google Scholar 

  52. Gensler, W.J.: Private communication.

    Google Scholar 

  53. Gensler, W.J. and F. Johnson: Podophyllotoxone, Picropodophyllone, and Dehydropodophyllotoxin. J. Amer. Chem. Soc. 77, 3674 (1955).

    CAS  Google Scholar 

  54. — Private communication.

    Google Scholar 

  55. Gensler, W.J. and C.M. Samour: Synthesis of a Degradation Product from Picropodophyllin. J. Amer. Chem. Soc. 72, 3318 (1950).

    CAS  Google Scholar 

  56. — The Single-Stage Conversion of I-(3′, 4′, 5′-Trimethoxypheny1-6, 7-methylenedioxy-3,4-dihydroisoquinoline to 2-(3′,4′,5′-Trimethoxybenzoyl)-4,5-methylenedioxystyrene. J. Amer. Chem. Soc. 74, 2959 (1952).

    CAS  Google Scholar 

  57. — A Dimer of Methylenedioxybenzene. J. Organ. Chem. (USA) 18, 9 (1953).

    CAS  Google Scholar 

  58. Gensler, W.J., C.M. Samour and S.Y. Wang: Synthesis of a DL-Stereoisomer of Podophyllic Acid. J. Amer. Chem. Soc. 76, 315 (1954).

    CAS  Google Scholar 

  59. Gensler, W.J. and S.Y. Wang: Synthesis of Picropodophyllin. J. Amer. Chem. Soc. 76, 5890 (1954).

    CAS  Google Scholar 

  60. Good, P.P.: The Family Flora and Materia Medica Botanica. 2 Vols. Elizabethtown, N.J. 1845.

    Google Scholar 

  61. Greenspan, E.M., J. Colsky, E.B. Schoenbach and M.J. Shear: Response of Patients with Advanced Neoplasms to the Intravenous Administration of Alpha-Peltatin. J. Nat. Cancer Inst. 14, 1257 (1954).

    CAS  Google Scholar 

  62. Griffith, R.E.: Medical Botany. Philadelphia: Lea and Blanchard. 1847.

    Google Scholar 

  63. Gronovius, J.F.: Flora Virginica. Leiden. 1762. [The 1739 edition was unavailable].

    Google Scholar 

  64. Guareschi, I.: Ricerche intorno alla podofillina. Gazz. chim. ital. 10, 16 (1880)

    Google Scholar 

  65. Guareschi, I.: Ricerche intorno alla podofillina. Ber. dtsch. chem. Ges. 12, 683 (1879).

    Google Scholar 

  66. Hartwell, J.L.: α-Peltatin, a New Compound Isolated from Podophyllum peltatum. J. Amer. Chem. Soc. 69, 2918 (1947).

    CAS  Google Scholar 

  67. Hartwell, J.L. and W.E. Detty: ß-Peltatin, a New Component of Podophyllin. J. Amer. Chem. Soc. 70, 2833 (1948).

    CAS  Google Scholar 

  68. — Components of Podophyllin. III. Isolation of α - and β-Peltatin. Structure Studies. J. Amer. Chem. Soc. 72, 246 (1950).

    CAS  Google Scholar 

  69. Hartwell, J.L., J.M. Johnson, D.B. Fitzgerald and M. Belkin: Silicicolin, a New Compound Isolated from Juniperus silicicola. J. Amer. Chem. Soc. 74, 4470 (1952).

    CAS  Google Scholar 

  70. D.B. Fitzgerald and M. Belkin — Podophyllotoxin from Juniperus Species; Savinin. J. Amer. Chem. Soc. 75, 235 (1935).

    Google Scholar 

  71. Hartwell, J.L. and A.W. Schrecker: Components of Podophyllin. IV. The Constitution of Podophyllotoxin. J. Amer. Chem. Soc. 72, 3320 (1950).

    CAS  Google Scholar 

  72. — Components of Podophyllin. V. The Constitution of Podophyllotoxin. J. Amer. Chem. Soc. 73, 2909 (1951).

    CAS  Google Scholar 

  73. — Relationship of Anthricin, Hernandion and Cicutin to Desoxypodophyllotoxin. J. Amer. Chem. Soc. 76, 4034 (1954).

    CAS  Google Scholar 

  74. Hartwell, J.L., A.W. Schrecker and G.Y. Greenberg: Components of Podophyllin. X. Relation of α-Peltatin to β-Peltatin. J. Amer. Chem. Soc. 74, 6285 (1952).

    CAS  Google Scholar 

  75. Hartwell, J.L., A.W. Schrecker and J.M. Johnson: The Structure of Silicicolin. J. Amer. Chem. Soc. 75, 2138 (1953).

    CAS  Google Scholar 

  76. Hartwell, J.L., A.W. Schrecker and J. Leiter: Relationship of the Steric Configuration of Podophyllotoxin and Related Lignans to Potency in Damaging Sarcoma 37. Proc. Amer. Assoc. Cancer Res. 1(No. 2), 19 (1954).

    Google Scholar 

  77. Hartwell, J.L. and M.J. Shear: Chemotherapy of Cancer: Classes of Compounds Under Investigation and Active Components of Podophyllin. Cancer Res. 7, 716 (1947).

    CAS  Google Scholar 

  78. Hata, C.: Studies on Formosan Plant Seed Oils. XIX. Components of the Seed Oil of Hernandia ovigera LINN. J. Chem. Soc. Japan 63, 1540 (1942) [Chem. Abstr. 47, 10872 (1953)].

    Google Scholar 

  79. Haworth, R.D.: Natural Resins. Annu. Rep. Chem. Soc. (London) 33, 266 (1936).

    Google Scholar 

  80. — The Chemistry of the Lignan Group of Natural Products. J. Chem. Soc. (London) 1942, 448.

    Google Scholar 

  81. Haworth, R.D. and J.R. Atkinson: The Constituents of Natural Phenolic Resins. Part X. Structure of l-Matairesinol Dimethyl Ether and Observations on the Condensation of Reactive Methylene Groups with O-Methyleugenol Oxide. J. Chem. Soc. (London) 1938, 797.

    Google Scholar 

  82. Haworth, R.D. and W. Kelly: The Constituents of Natural Phenolic Resins. Part VIII. Lariciresinol, Cubebin, and Some Stereochemical Relationships. J. Chem. Soc. (London) 1937, 384.

    Google Scholar 

  83. Haworth, R.D. and T. Richardson: The Constituents of Natural Phenolic Resins. Part. IV. Synthesis of Dehydroanhydropicropodophyllin. J. Chem. Soc. (London) 1936, 348.

    Google Scholar 

  84. Haworth, R.D. and G. Sheldrick: The Constituents of Natural Phenolic Resins. Part II. “Sulphite-liquors Lactone”. J. Chem. Soc. (London) 1935, 636.

    Google Scholar 

  85. Haworth, R.D. and L. Wilson: The Constituents of Natural Phenolic Resins. Part XXII. Reduction of Some Lactonic Lignans with Lithium Aluminium Hydride. J. Chem. Soc. (London) 1950, 71.

    Google Scholar 

  86. Haworth, R.D. and D. Woodcock: The Constituents of Natural Phenolic Resins. Part XV. The Stereochemical Relationship of Lariciresinol and Pinoresinol. J. Chem. Soc. (London) 1939, 1054.

    Google Scholar 

  87. Hearon, W.M., H.B. Lackey and W.W. Moyer: Conidendrin. I. Its Isomerization and Demethylation. J. Amer. Chem. Soc. 73, 4005 (1951).

    CAS  Google Scholar 

  88. Hearon, W.M. and W.S. MacGregor: The Naturally Occurring Lignans. Chem. Rev. 55, 957 (1955).

    CAS  Google Scholar 

  89. Henry, S.: A New and Complete American Medical Family Herbal. New York: S. Henry. 1814.

    Google Scholar 

  90. Hill, J.: The Useful Family Herbal. 2nd Ed. London: Johnston and Owen. 1755.

    Google Scholar 

  91. Hirsch, B.: Universal-Pharmakopöe. 2 Vols. Göttingen: Vandenhoeck und Ruprecht. 1902.

    Google Scholar 

  92. Hodgson, W.: On the Bitter Principle of Podophyllum Peltatum. Amer. J. Pharm. 3, 273 (1832).

    Google Scholar 

  93. Holmberg, B. und M. SjÕberg: Lignin-Untersuchungen. IL: Dimethyl-sulfitlaugen-Lactone. Ber. dtsch. chem. Ges. 54, 2406 (1921).

    Google Scholar 

  94. IBN El-Beïthar: Traité des simples (traduit par L. LECLERC). Notices et extraits des manuscrits de la Bibliothèque Nationale 23, I (1877), 25, I (1881), 26, I (1883). Paris: Imprimerie Nationale.

    Google Scholar 

  95. Jerzmanowska, Z.: Über Hyperin, ein Glucosid von Hypericum perforatum L. WiadomoŠci farmac. 64, 527 (1937) [Chem. Zbl. 1938, I, 333].

    CAS  Google Scholar 

  96. Joncquet, D.: Joncquet Dionysii Hortus. Paris: Clouzier. 1659.

    Google Scholar 

  97. Jørgensen, C and H. Kofod: Paper Chromatography of Podophyliin. Acta Chem. Scand. 8, 941 (1954).

    Google Scholar 

  98. Kaplan, I.W.: Condylomata Acuminata. New Orleans Med. Surg. J. 94, 388 (1942).

    Google Scholar 

  99. Kelly, M.G. and J.L. Hartwell: The Biological Effects and the Chemical Composition of Podophyllin. A Review. J. Nat. Cancer Inst. 14, 967 (1954).

    CAS  Google Scholar 

  100. King, F.E.: The Chemistry of Wood Extractives. Chem. and Ind. 1953, 1325.

    Google Scholar 

  101. King, J.: New York Philos. Med. J. 1, 159 (1844).

    Google Scholar 

  102. — Western Med. Reformer (Cincinnati) 5, 175 (1846).

    Google Scholar 

  103. — The American Eclectic Dispensatory. Cincinnati: Moore, Wilstach and Keys. 1854.

    Google Scholar 

  104. — Discovery of Podophyllin. College J. Med. Sci. (Cincinnati) 2, 557 (1857).

    Google Scholar 

  105. King, L.S. and M. Sullivan: The Similarity of the Effect of Podophyllin and Colchicine and Their Use in the Treatment of Condylomata Acuminata. Science (Washington) 104, 244 (1946).

    CAS  Google Scholar 

  106. Kofod, H. and C. Jørgensen: Bromopodophyllotoxin. Acta Chem. Scand. 8, 1294 (1954).

    CAS  Google Scholar 

  107. — Dehydropodophyllotoxin, a New Compound Isolated from Podophyllum peltatum L. Acta Chem. Scand. 8, 1296 (1954).

    CAS  Google Scholar 

  108. — Desoxypodophyllotoxin, Isolated from Podophyllin. Acta Chem. Scand. 9, 346 (1955).

    CAS  Google Scholar 

  109. — A Note on the Melting Point of Podophyllotoxin. Acta Chem. Scand. 9, 347 (1955).

    CAS  Google Scholar 

  110. — The Action of Bromine on Podophyllotoxin and Picropodophyllin. Acta Chem. Scand. 9, 1327 (1955).

    CAS  Google Scholar 

  111. Kursten, R.: Über die Bestandteile von Rhizoma Podophylli. Arch. Pharmaz. 229, 220 (1891).

    Google Scholar 

  112. Kuester, H.L.: A Chemical Study of the Rhizome and Roots of Podophyllum Peltatum L. J. Amer. Pharmaceut. Assoc. 15, 259 (1926).

    CAS  Google Scholar 

  113. Leighton, J., I. Kline, M. Belkin and H.C. Orr: Effects of a Podophyllotoxin Derivative on Tissue Culture Systems in Which Human Cancer Invades Normal Tissue. Cancer Res. 17, 336 (1957).

    CAS  Google Scholar 

  114. Leiter, J., V. Downing, J.L. Hartwell and M.J. Shear: Damage Induced in Sarcoma 37 with Podophyllin, Podophyllotoxin, Alpha-Peltatin, Beta-Peltatin, and Quercetin. J. Nat. Cancer Inst. 10, 1273 (1950).

    CAS  Google Scholar 

  115. Leiter, J., A.D. Paradis and V.S. Waravdekar: Enzyme Changes Induced in Normal and Malignant Tissues with Chemical Agents. II. Effect of Various Compounds on the Cytochrome Oxidase Activity of Transplanted Tumors. J. Nat. Cancer Inst. 14, 177 (1953).

    CAS  Google Scholar 

  116. Leiter, J., A. Perrault et al.: Unpublished results.

    Google Scholar 

  117. Lewis, J.R.: Observations on Podophyllum Peltatum. Amer. J. Pharm. 19, 165 (1847).

    Google Scholar 

  118. Lewis, W.: An Experimental History of the Materia Medica. 4th Ed. London: J. Johnson. 1791.

    Google Scholar 

  119. Lindley, J.: Flora Medica. London: Longman. 1838.

    Google Scholar 

  120. Linnaeus, C.: Hortus Cliffortianus. Amsterdam. 1737.

    Google Scholar 

  121. — Hortus Upsaliensis. Stockholm: Salvius. 1748.

    Google Scholar 

  122. — Species Plantarum, p. 505. Stockholm: Salvius. 1753.

    Google Scholar 

  123. Linstead, R.P., W.E. Doering, S.B. Davis, P. Levine and R.R. Whetstone: The Stereochemistry of Catalytic Hydrogénation. I. The Stereochemistry of the Hydrogénation of Aromatic Rings. J. Amer. Chem. Soc. 64, 1985 (1942).

    CAS  Google Scholar 

  124. Lombard, L.H.: Medicinal Plants of our Maine Indians. In: The Maine Writers Research Club. Maine Indians in History and Legends. Portland: Severn-Wylie-Jewett. 1952.

    Google Scholar 

  125. Loran, M.R. and E.P. Guth: Preliminary Report of Lysis of Mouse Sarcoma 37 by a Component Isolated from Resin of Podophyllum. J. Amer. Pharmaceut. Assoc, Sci. Ed. 40, 254 (1951).

    CAS  Google Scholar 

  126. Loran, M.R. and A. Towbin: Chemistry, Pharmacology and Oncolytic Effect of the High Molecular Weight Fraction Isolated from Podophyllin. Federat. Proc. (Amer. Soc. exp. Biol.) II, 370 (1952).

    Google Scholar 

  127. — The Tumor-Depressant Effect of the Nondialyzable Buffer-Soluble Fraction of Podophyllin. (Abstract.) Cancer Res. 12. 279 (1952).

    Google Scholar 

  128. Maisch, J.M.: Remarks on Resin of Podophyllum. Amer. J. Pharm. 46, 231 (1874).

    Google Scholar 

  129. Marion, L.: The Isolation of Cicutin from Cicuta maculata L. Canad. J. Res. 20B, 157 (1942).

    Google Scholar 

  130. Martin, G.J., A. Szent-Györgyi et al.: Conference on Bioflavonoids and the Capillary. Ann. New York Acad. Sci. 61, Art. 3, 637 (1955).

    Google Scholar 

  131. Mayer, F.F.: Note on the Proximate Principles of Some Berberidaceae and Ranunculaceae. Amer. J. Pharm. 35, 97 (1863).

    Google Scholar 

  132. Mellanoff, I.S. and H.J. Schaeffer: A Study of the Resins of Podophyllum Peltatum L. Amer. J. Pharm. 99, 323 (1927).

    CAS  Google Scholar 

  133. Mentzel, C.: Index nominum plantarum universalis. Berlin: Runge. 1682.

    Google Scholar 

  134. Merrell, W.S.: Eclectic Pharmacy. Eclectic Med. J. (Cincinnati) 9, 297 (1850).

    Google Scholar 

  135. Meyerhof, M. and G.P. Sobhy: The Abridged Version of “The Book of Simple Drugs” of Ahmad ibn Muhammad al-Ghafiqi, by Gregorius abu’l-Farag (Barhebraeus). Public. No. 4. Cairo: The Egyptian Univ., Fac. of Med. 1932-1938.

    Google Scholar 

  136. Molbech, C.: Henrik Harpestrengs Danske Laegebog. Copenhagen: Thiele. 1826.

    Google Scholar 

  137. Nadkarni, M.V., P.B. Maury and J.L. Hartwell: Components of Podophyllin. VI. Isolation of Two New Compounds from Podophyllum emodi WALL. J. Amer. Chem. Soc. 74, 280 (1952).

    CAS  Google Scholar 

  138. Nadkarni, M.V., J.L. Hartwell, P.B. Maury and J. Leiter: Components of Podophyllin. XL Isolation of Two New Compounds from Podophyllum emodi WALL. J. Amer. Chem. Soc. 75, 1308 (1953).

    CAS  Google Scholar 

  139. National Formulary, The. 9th Ed. (1950); 10th Ed. (1955). Washington: Amer. Pharmaceut. Assoc.

    Google Scholar 

  140. Noguchi, K. and M. Kawanami: Study of the Active Components of the Umbelliferae. X. Study of the Components of Anthriscus sylvestris HOFFM. J. pharmac. Soc. Japan 60, 629 (1940) [Chem. Abstr. 47, 6386 (1953)].

    CAS  Google Scholar 

  141. Oribasius, D.: Oeuvres d’Oribase (trad, par U.C. Bussemaker et C. Daremberg). Paris: Imprimerie Nationale. 1851-1876.

    Google Scholar 

  142. Padawer, J.: Studies on Mammalian Mast Cells. Trans. New York Acad. Sci. (2) 19, 690 (1957).

    CAS  Google Scholar 

  143. Pankajamani, K.S. and T.R. Seshadri: Survey of Anthoxanthins — Part I. Proc. Indian Acad. Sei. 36A, 157 (1952) [Chem. Abstr. 48, 2702 (1954)].

    CAS  Google Scholar 

  144. Patterson, R.F. and H. Hibbert: Studies on Lignin and Related Compounds. LXXIL The Ultraviolet Absorption Spectra of Compounds Related to Lignin. J. Amer. Chem. Soc. 65, 1862 (1943).

    CAS  Google Scholar 

  145. Pharmacopoeia of the United States of America, ist Ed. (1820); 4th Revision (1863); 12th Revision (1942); 15th Revision (1955). New York: U.S.-Pharmacopeial Convention.

    Google Scholar 

  146. Podwyssotzki, V.: Pharmakologische Studien über Podophyllun peltaium. Arch. exp. Pathol. Pharmakol. 13, 29 (1880).

    Google Scholar 

  147. — Über die wirksamen Bestandtheile des Podophyllins. Pharm. Z. Rußl. 20, 49, 777, 793, 809 (1881) [Ber. dtsch. chem. Ges. 15, 377 (1882)].

    Google Scholar 

  148. Potter, S.O.L. and R.J.E. Scott: Therapeutics, Materia Medica and Pharmacy. Philadelphia: Blakiston. 1931.

    Google Scholar 

  149. Power, F.B.: Resina podophylli. Amer. J. Pharm. 46, 227 (1874).

    Google Scholar 

  150. — On the Resin of the Rhizome of Podophyllum Peltaium LINN. Proc. Amer. Pharmaceut. Assoc. 25, 420 (1877).

    Google Scholar 

  151. Pradhan, S.N., B. Achinstein and M.J. Shear: Effect of Various Drugs on the Tumor-necrotizing Activity of Several Chemical Agents in Mice. Cancer Res. 16, 1062 (1956).

    CAS  Google Scholar 

  152. Press, J. and R. Brun: Sur quelques constituants de la podophylline et sur la structure de la podophyllotoxine, de l’α-peltatine et de la βÖ-peltatine. Helv. Chim. Acta 37, 190 (1954).

    CAS  Google Scholar 

  153. — Sur la structure de la podophyllotoxine et des peltatines. Helv. Chim. Acta 37, 1543 (1954).

    CAS  Google Scholar 

  154. Price, E.H.: Thesis. Univ. of Maryland. 1949.

    Google Scholar 

  155. Rafinesque, C.S.: Medical Flora; or Medical Botany of the United States of North America. Philadelphia: Atkinson and Alexander. 1828-1830.

    Google Scholar 

  156. Reeve, W. and W.M. Eareckson, III: Synthesis of Some Isoquinoline Derivatives Related to Podophyllotoxin. J. Amer. Chem. Soc. 72, 5195 (1950).

    CAS  Google Scholar 

  157. Reeve, W. and H. Myers: Synthesis of a Substituted Phenylnaphthalene Related to Podophyllotoxin. J. Amer. Chem. Soc. 75, 4957 (1953).

    CAS  Google Scholar 

  158. Reeve, W. and J.D. Sterling, Jr.: Synthesis of Some Compounds Related to Podophyllotoxin. J. Amer. Chem. Soc. 71, 3657 (1949).

    CAS  Google Scholar 

  159. Ricci, J.V.: Aetios of Amida. The Gynaecology and Obstetrics of the VI Century, A.D. Philadelphia: Blakiston. 1950.

    Google Scholar 

  160. Rinne, F.: Das Receptbuch des Scribonius Largus. In: E.R. Robert, Historische Studien aus dem Pharmakologischen Institute der Kaiserlichen Universität Dorpat, Bd. V, S.I. Halle: Tausch und Grosse. 1896.

    Google Scholar 

  161. Robertson, A. and R.B. Waters: Podophyllotoxin. J. Chem. Soc. (London) 1933, 83.

    Google Scholar 

  162. Rosenthal, D.A.: Synopsis plantarum diaphoricarum. Erlangen: Enke. 1861.

    Google Scholar 

  163. Royle, J.F.: Illustrations of the Botany and Other Branches of Natural History of the Himalayan Mountains and the Flora of Cashmere. London: W.H. Allen. 1839.

    Google Scholar 

  164. Salomon, K. and A.F. Bina: Ultraviolet Absorption Spectra of Mescaline Sulfate and β-Phenethylamine Sulfate. J. Amer. Chem. Soc. 68, 2403 (1946).

    CAS  Google Scholar 

  165. Sando, C.E.: Coloring Matters of Grimes Golden, Jonathan, and Stayman Winesap Apples. J. Biol. Chem. 117, 45 (1937).

    CAS  Google Scholar 

  166. Schmidt, O. Th. und W. Mayer: Die Konstitution der Spaltsäure C14H12O11 aus Chebulin-und Chebulagsäure. V. Mitt, über natürliche Gerbstoffe. Liebigs Ann. Chem. 571, 1 (1951).

    CAS  Google Scholar 

  167. Schrecker, A.W., G.Y. Greenberg and J.L. Hartwell: Components of Podophyllin. VII. Absorption Spectra and Reaction with Iodine of the Dihydro-ß-naphthoic Acids. J. Amer. Chem. Soc. 74, 5669 (1952).

    CAS  Google Scholar 

  168. J.L. Hartwell — Components of Podophyllin. XV. Pyrolysis of Podophyllotoxin Halides. J. Amer. Chem. Soc. 76, 1182 (1954).

    CAS  Google Scholar 

  169. J.L. Hartwell — Components of Podophyllin. XVI. Podophyllotoxin Haloacetates and Quaternary Derivatives. J. Amer. Chem. Soc. 76, 1184 (1954).

    CAS  Google Scholar 

  170. Schrecker, A.W. and J.L. Hartwell: Components of Podophyllin. VIII. Study of Intermediates in the Synthesis of Dehydroanhydropicropodophyllin. J. Amer. Chem. Soc. 74, 5672 (1952).

    CAS  Google Scholar 

  171. — Components of Podophyllin. IX. The Structure of the Apopicropodophyllins. J. Amer. Chem. Soc. 74, 5676 (1952); correction, p. 6321.

    CAS  Google Scholar 

  172. — Components of Podophyllin. XII. The Configuration of Podophyllotoxin. J. Amer. Chem. Soc. 75, 5916 (1953).

    CAS  Google Scholar 

  173. — Components of Podophyllin. XIII. The Structure of the Peltatins. J. Amer. Chem. Soc. 75, 5924 (1953).

    CAS  Google Scholar 

  174. — Components of Podophyllin. XIV. Acid-catalyzed Reactions of Podophyllotoxin and its Stereoiso mers. J. Amer. Chem. Soc. 76, 752 (1954)

    CAS  Google Scholar 

  175. — On the Structure of Podophyllotoxin and the Peltatins. Helv. Chim. Acta 37, 1541 (1954).

    CAS  Google Scholar 

  176. — Application of Tosylate Reductions and Molecular Rotations to the Stereochemistry of Lignans. J. Amer. Chem. Soc. 77, 432 (1955); correction p. 6725.

    CAS  Google Scholar 

  177. — Components of Podophyllin. XX. The Absolute Configuration of Podophyllotoxin and Related Lignans. J. Organ. Chem. (USA) 21, 381 (1956).

    CAS  Google Scholar 

  178. — The Absolute Configuration of Lignans. J. Amer. Chem. Soc. 79, 3827 (1957).

    CAS  Google Scholar 

  179. Schrecker, A.W., J.L. Hartwell and W.C. Alford: Components of Podophyllin. XVIII. Polymorphic Modifications of Podophyllotoxin. J. Organ. Chem. (USA) 21, 288 (1956).

    CAS  Google Scholar 

  180. Schrecker, A.W., P.B. Maury, J.L. Hartwell and J. Leiter: Component of Podophyllin. XVII. Ionic Derivatives of Podophyllotoxin and of the Peltatins. J. Amer. Chem. Soc. 77, 6565 (1955).

    CAS  Google Scholar 

  181. J.L. Hartwell and J. Leiter — Soluble Derivatives of Podophyllotoxin and of the Peltatins. Résumés communications (3e Congrès Internat. Biochimie, Bruxelles, 1955) p. 2, No. 1-11.

    Google Scholar 

  182. Schrecker, A.W. and M.M. Trail: Methyl Desoxypodophyllate and its Methyl Ether. J. Organ. Chem. (USA) 23, 767 (1958).

    CAS  Google Scholar 

  183. Schrecker, A.W., M.M. Trail and J.L. Hartwell: Components of Podophyllin. XIX. Isomorphism in the Podophyllotoxin Series. J. Organ. Chem (USA) 21, 292 (1956).

    CAS  Google Scholar 

  184. Schroeter, G., L. Lichtenstadt und D. Ireneu: Über die Konstitution de Guaiacharz-Substanzen. (I.) Ber. dtsch. chem. Ges. 51, 1587 (1918).

    CAS  Google Scholar 

  185. Scotti, G.: Flora medica della provincia di Como. Como: C. Franchi. 1872.

    Google Scholar 

  186. SeidlovÁ-MaŠinovÁ, V., J. Malinsky and F. Àantavyý: The Biological Effects of Some Podophyllin Compounds and Their Dependence on Chemicc Structure. J. Nat. Cancer Inst. 18, 359 (1957).

    Google Scholar 

  187. Seshadri, T.R. and S.S. Subramanian: Components of Indian Podophyllun J. Sci. Industr. Res. (India) 9B, 137 (1950) [Chem. Abstr. 44, 9633 (1950)]

    CAS  Google Scholar 

  188. Shear, M.J.: Polysaccharides in Biology. Trans. First Conf. Josiah Mac Jr. Found. (New York) 1956, 134.

    Google Scholar 

  189. Späth, E., F. Wessely und L. Kornfeld: Über die Konstitution von Podophyllotoxin und Pikro-podophyllin. Ber. dtsch. chem. Ges. 65, 1536 (1932).

    Google Scholar 

  190. Späth, E., F. Wessely und E. Nadler: Zur Konstitution des Podophyllc toxins und Pikro-podophyllins. Ber. dtsch. chem. Ges. 65, 1773 (1932).

    Google Scholar 

  191. E. Nadler — Zur Konstitution des Podophyllotoxins und Pikro-podophyllins Ber. dtsch. chem. Ges. 66, 125 (1933).

    Google Scholar 

  192. Stoll, A., J. Renz and A.V. Wartburg: The Isolation of Podophyllotoxin Glucoside. J. Amer. Chem. Soc. 76, 3103 (1954).

    CAS  Google Scholar 

  193. Stoll, A., J. Renz und A.V. Wartburg: Die Isolierung von Podophyllotoxin-glucosid aus dem indischen Podophyllum emodi WALL. 2. Mitt, über mitosehemmende Naturstoffe. Helv. Chim. Acta 37, 1747 (1954).

    CAS  Google Scholar 

  194. Stoll, A., J. Rutschmann, A. V. Wartburg und J. Renz: Über die Partialsynthese von 14C-Podophyllotoxin-β-glucosid und zur Darstellung von 14C-Diazomethan. 6. Mitt. über mitosehemmende Naturstoffe. Helv. Chim. Acta 39, 993 (1956).

    CAS  Google Scholar 

  195. Stoll, A., A.V. Wartburg, E. Angliker and J. Renz: The Isolation of 4′-Demethyl-podophyllotoxin-glucoside from Rhizomes of Podophyllum emodi WALL. J. Amer. Chem. Soc. 76, 5004 (1954).

    CAS  Google Scholar 

  196. E. Angliker and J. Renz — Glucosides from the Rhizomes of Podophyllum peltatum LINN. J. Amer. Chern. Soc. 76, 6413 (1954).

    Google Scholar 

  197. Stoll, A., A.V. Wartburg and J. Renz: The Isolation of α-Peltatin Glucoside from the Rhizomes of Podophyllum peltatum L.J. Amer. Chem. Soc. 77, 1710 (1955).

    CAS  Google Scholar 

  198. Sullivan, M.: Podophyllotoxin. Arch. Dermatol. and Syphilol. (USA) 60, 1 (1949).

    CAS  Google Scholar 

  199. — Private communication.

    Google Scholar 

  200. Sullivan, M. and K. Blanchard: Podophyllotoxin. A Preliminary Note. Bull. Johns Hopkins Hosp. 81, 65 (1947).

    CAS  Google Scholar 

  201. Sullivan, M., M. Friedman and J.T. Hearin: Treatment of Condylomata Acuminata with Podophyllotoxin. Southern Med. J. 41, 336 (1948).

    CAS  Google Scholar 

  202. Sullivan, M. and J.T. Hearin: Treatment of Condyloma Acuminatum with Peltatins. Arch. Dermatol. and Syphilol. (USA) 66, 706 (1952).

    CAS  Google Scholar 

  203. Sullivan, M. and L.S. King: Effects of Resin of Podophyllum on Normal Skin, Condylomata Acuminata and Verrucae Vulgares. Arch. Dermatol. and Syphilol. (USA) 56, 30 (1947).

    CAS  Google Scholar 

  204. TchÚgaeff, L.: Untersuchungen über optische Activität. Ber. dtsch. chem. Ges. 31, 360 (1898).

    Google Scholar 

  205. Thompson, F.A.: Podophyllin emodi. Amer. J. Pharm. 62, 245 (1890).

    Google Scholar 

  206. Thoms, H. und E. Pupko: Beitrag zur Ermittlung der Konstitution des Podophyllotoxins. Arb. Pharm. Inst. Univ. Berlin 13, 110 (1927).

    Google Scholar 

  207. Thorndike, L.: The Herbal of Rufinus. Chicago: Univ. Chicago Press. 1946.

    Google Scholar 

  208. Tournefort, J.P. de: Institutiones rei herbariae. 2e ed. Paris: Typogr. regia. 1700.

    Google Scholar 

  209. Umney, J.C.: Podophyllum emodi. Pharmaceut. J. and Trans. (London) 23, 207 (1892).

    Google Scholar 

  210. Van Royen, A.: Florae Leidensis. Prodromus. Leiden: Luchtmans. 1740.

    Google Scholar 

  211. Viehoever, A. and H. Mack: Biochemistry of May Apple Root (Podophyllum Peltatum). I. J. Amer. Pharmaceut. Assoc. 27, 632 (1938).

    CAS  Google Scholar 

  212. Walker, G.N.: Podophyllotoxin Studies. A Synthesis of the Carbon-Oxygen Skeleton. J. Amer. Chem. Soc. 75, 3390 (1953).

    CAS  Google Scholar 

  213. — Podophyllotoxin Studies. Reductive Methods in the Synthesis of Tetralin Lactones from α-Tetralone Derivatives. J. Amer. Chem. Soc. 75, 3393 (1953).

    CAS  Google Scholar 

  214. — Stobbe Condensation of 3, 4, 5-Trimethoxybenzaldehyde and Ethyl 3,4-Methylenedioxybenzylsuccinate. J. Amer. Chem. Soc. 76, 6205 (1954).

    CAS  Google Scholar 

  215. — Synthesis of Dehydropodophyllotoxin Acetate. J. Amer. Chem. Soc. 78, 2316 (1956).

    CAS  Google Scholar 

  216. Waravdekar, V.S., A. Domingue and J. Leiter: Effect of Podophyllotoxin, Alpha-Peltatin and Beta-Peltatin on the Cytochrome Oxidase Activity of Sarcoma 37. J. Nat. Cancer Inst. 13 393 (1952).

    CAS  Google Scholar 

  217. Waravdekar, V.S., A.D. Paradis and J. Leiter: Enzyme Changes Induced in Normal and Malignant Tissues with Chemical Agents. III. Effect of Acetylpodophyllotoxin-ω-Pyridinium Chloride on Cytochrome Oxidase, Cytochrome C, Succinoxidase, Succinic Dehydrogenase, and Respiration of Sarcoma 37. J. Nat. Cancer Inst. 14, 585 (1953).

    CAS  Google Scholar 

  218. J. Leiter — Enzyme Changes Induced in Normal and Malignant Tissues with Chemical Agents. IV. Effect of Alpha-Peltatin on Glucose Utilization by Sarcoma 37 and on the Adenosinetriphosphatase, Hexokinase, Aldolase and Pyridine Nucleotide Levels of Sarcoma 37. J. Nat. Cancer Inst. 16, 31 (1955).

    CAS  Google Scholar 

  219. J. Leiter — Enzyme Changes Induced in Normal and Malignant Tissues with Chemical Agents. V. Effect of Acetylpodophyllotoxin-ω-Pyridinium Chloride on Uricase, Adenosine Deaminase, Nucleoside Phosphorylase, and Glutamic Dehydrogenase Activities. J. Nat. Cancer Inst. 16, 99 (1955).

    CAS  Google Scholar 

  220. Waravdekar, V.S., O. Powers and J. Leiter: Enzyme Changes Induced in Normal and Malignant Tissues with Chemical Agents. VI. Effect of Acetylpodophyllotoxin-ω-Pyridinium Chloride on Malic Oxidase and on Isocitric Oxidase Systems of Sarcoma 37. J. Nat. Cancer Inst. 16, 1443 (1956).

    CAS  Google Scholar 

  221. J. Leiter — Enzyme Changes Induced in Normal and Malignant Tissues with Chemical Agents. VII. Effect on Hydrolytic and Synthetic Enzymes of Diphosphopyridine Nucleotide in Sarcoma 37. J. Nat. Cancer Inst. 17, 145 (1956).

    CAS  Google Scholar 

  222. Wartburg, A. V., E. Angliker und J. Renz: Lignanglucoside aus Podophyllum peltatum L. 7. Mitt, über mitosehemmende Naturstoffe. Helv. Chim. Acta 40, 1331 (1957).

    Google Scholar 

  223. Wawzonek, S.: Chromones, Flavones, and Isoflavones. In: R.C. Elderfield, Heterocyclic Compounds, Vol.11, p. 229. New York: J. Wiley. 1951.

    Google Scholar 

  224. Wehmer, C.: Die Pflanzenstoffe. Jena: G.Fischer. 1929-1931.

    Google Scholar 

  225. Wessely, F.: Private communication.

    Google Scholar 

  226. Willaman, J.J.: Some Biological Effects of the Flavonoids. J. Amer. Pharmaceut. Assoc, Sci. Ed. 44, 404 (1955).

    CAS  Google Scholar 

  227. Woods, M. and D. Burk: Podophyllotoxin Derivative as Inhibitor of Insulin-Sensitive Tumor Glycolysis. Proc. Amer. Assoc. Cancer Res. 2(No. 1), 54 (1955).

    Google Scholar 

  228. — Differential Metabolic and Necrotizing Responses of Tumors to Podophyllin and Colchicine Derivatives. Fédérât. Proc. (Amer. Soc. exp. Biol.) 15, 387 (1956).

    Google Scholar 

  229. Woods, M., G. Hobby and D. Burk: Synergistic Action between a Podophyllum Extract and Sex Steroids in Tumor Necrotization and Glycolysis. Proc. Amer. Assoc. Cancer Res. 2(No. 2), 158 (1956).

    Google Scholar 

  230. Woods, M., J. Hunter and D. Burk: Regulation of Glucose Utilization in Tumors by a Stress-Modified Insulin: Anti-Insulin System. J. Nat. Cancer Inst. 16, 351 (1955).

    CAS  Google Scholar 

  231. Woods, M., J. Hunter and D. Burk: A Model of Multiple Chemotherapy: Synergistic Action of a Podophyllin Derivative, 2,4-Dinitrophenol, and Oxygen. Proc. Amer. Assoc. Cancer Res. 2(No. 2), 158 (1956).

    Google Scholar 

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    J. L. Hartwell & A. W. Schrecker

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Hartwell, J.L., Schrecker, A.W. (1958). The Chemistry of Podophyllum. In: Zechmeister, L. (eds) Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles. Fortschritte der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products / Progrès dans la Chimie des Substances Organiques Naturelles, vol 15. Springer, Vienna. https://doi.org/10.1007/978-3-7091-7162-2_3

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