Advertisement

Abstract

According to Haworth (73, 74), lignans are plant products based on carbon skeleta having two n-propylbenzene residues linked by the β-carbon atoms of the side chains. Around 1940, when this definition was published, practically all known bis-phenylpropanoids were derivatives of structural variants of only 1 and 2 (Table 1). Since then, the additional skeleta 315 were recognized and the restriction imposed on the mode of union of the two units seems now unprofitable. It was therefore proposed that the term lignan be extended to cover all natural products of low molecular weight that arise primarily from the oxidative coupling of p-hydroxyphenylpropene units (106), a concept which implicitly also refers to variants of skeleta such as 15 in which the two units are linked by an oxygen bridge. This is, of course, fundamentally a biogenetic definition and implies knowledge of the monomeric precursor units.

Keywords

Absolute Configuration Oxidative Coupling Aryl Group Cinnamyl Alcohol Tetrahedron Letter 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Adjangba, M. S.: Recherches sur les Lignanes. IV. Condensation d’un Ether Phenolique avec une Lactone en présence de Chlorure Stannique. Bull. soc. chim. France 1963, 1007.Google Scholar
  2. 2.
    Adjangba, M. S.: Recherches sur les Lignanes. V. Synthèses Totales de quelques Lignanes Naturels et de leurs Dérivés. Bull. soc. chim. France 1963, 1942.Google Scholar
  3. 3.
    Adjangba, M. S.: Progrès Récents dans la Chimie des Lignanes. Bull. soc. chim. France 1963, 2344.Google Scholar
  4. 4.
    Adjangba, M. S., and D. Billet: Recherches sur les Lignanes. III. Confirmation par Synthèse Totale de la Structure de la Galcatine. Bull. soc. chim. France 1962, 1970.Google Scholar
  5. 5.
    Adjangba, M. S., D. Billet, and C. Mentzer: Recherches sur les Lignanes. II. Sur une Nouvelle Synthèse des Diaryl-2,5-diméthyl-3,4-furanes. Bull. soc. chim. France 1962, 132.Google Scholar
  6. 6.
    Ahmed, R., and R. Stevenson: Synthesis of Eupomatenoid-7 and Eupomatenoid-12. Phytochem. 14, 2710 (1975).CrossRefGoogle Scholar
  7. 7.
    Aiba, C. J., R. Braz F-., and O. R. Gottlieb: The Chemistry of Brazilian Lauraceae. XX. Porosin: a Neolignan from Ocotea porosa. Phytochem. 12, 413 (1973).CrossRefGoogle Scholar
  8. 8.
    Aiba, C. J., R. G. C. Corrêa, and O. R. Gottlieb: The Chemistry of Brazilian Lauraceae. XXII. Natural Occurrence of Erdtman’s Dehydrodiisoeugenol. Phyto­chem. 12, 1163 (1973).CrossRefGoogle Scholar
  9. 9.
    Aiba, C. J., J. B. Fernandes, O. R. Gottlieb, and J. G. S. Maia: The Chemistry of Brazilian Lauraceae. XXX. Neolignans from an Aniba Species (later classified A. simulons). Phytochem. 14, 1597 (1975).CrossRefGoogle Scholar
  10. 10.
    Aiba, C. J., A. M. Giesbrecht, O. R. Gottlieb, and F. M. Pagliosa: Unpublished work (1976).Google Scholar
  11. 11.
    Aiba, C. J., A. M. Giesbrecht, O. R. Gottlieb, and M. Yoshida: A Revision of the Structure of the Neolignan Canellin-B. Communication presented at the XXVIII Annual Meeting of Sociedade Brasileira para o Progresso da Ciencia, Brasilia (1976).Google Scholar
  12. 12.
    Aiba, C. J., and O. R. Gottlieb: The Chemistry of Brazilian Lauraceae. XXVIII. Synthesis of (±)-Licarin-B. Phytochem. 14, 253 (1975).CrossRefGoogle Scholar
  13. 13.
    Aiba, C. J., O. R. Gottlieb, U. Kamphausen, M. T. Magalhàes, and M. Yoshida: Unpublished work (1976).Google Scholar
  14. 14.
    Aiba, C. J., O. R. Gottlieb, and M. T. Magalhàes: Unpublished work (1976).Google Scholar
  15. 15.
    Aiba, C. J., O. R. Gottlieb, and J. G. S. Maia: Neolignans from Duguetia surinamensis. Communication presented at the XXVII Annual Meeting of Sociedade Brasileira para o Progresso da Ciencia, Belo Horizonte (1975).Google Scholar
  16. 16.
    Aiba, C. J., O. R. Gottlieb, F. M. Pagliosa, and M. T. Magalhaes: Unpublished work (1976).Google Scholar
  17. 17.
    Aiba, C. J., O. R. Gottlieb, F. M. Pagliosa, and M. Yoshida: Unpublished work (1976).Google Scholar
  18. 18.
    Aiba, C. J., O. R. Gottlieb, M. Yoshida, J. C. Mourào, and H. E. Gottlieb: The Chemistry of Brazilian Lauraceae. XXXV. The Structure of Porosin. Phyto­chem. 15, 1031 (1976).CrossRefGoogle Scholar
  19. 19.
    Alvarenga, M. A. de, O. Castro C., O. R. Gottlieb, and J. G. S. Maia: Un­published work (1976).Google Scholar
  20. 20.
    Andrade, C. H. S., O. R. Gottlieb, and J. G. S. Maia: Unpublished work (1974).Google Scholar
  21. 21.
    Araújo Lima, O., O. R. Gottlieb, and M. T. Magalhàes: The Chemistry of Brazilian Lauraceae. XX. Burchellin, a Neolignan from Aniba burchellii. Phytochem. 11, 2031 (1972).CrossRefGoogle Scholar
  22. 22.
    Atkinson, J. R., and R. D. Haworth: The Constituents of Natural Phenolic Resins. XII. The Action of Selenium on Lignans. J. Chem. Soc. ( London ) 1938, 1681.Google Scholar
  23. 23.
    Aulin-Erdtman, G., Y. Tomita, and S. Forsén: Studies on the Degradation of Lignin and Model Compounds. I. The Configuration of Dehydrodi-isoeugenol. Acta Chem. Scand. 17, 535 (1963).CrossRefGoogle Scholar
  24. 24.
    Baker, P. M., and L. E. S. Barata: Chemical Study of Amazonian Plants with Biological Action: The Structure of a New Lignan. Communication presented at the XXVI Annual Meeting of Sociedade Brasileira para o Progresso da Ciencia, Recife (1974).Google Scholar
  25. 25.
    Barata, L. E. S., P. M. Baker, O. R. Gottlieb, and E. Ruveda: Syntheses of Neolignans. Communication presented at the XXVIII Annual Meeting of Sociedade Brasileira para o Progresso da Ciencia, Brasilia (1976).Google Scholar
  26. 26.
    Bhacca, N. S., and R. Stevenson: The Constitution of Otobain. J. Organ. Chem. (USA) 28, 1638 (1963).CrossRefGoogle Scholar
  27. 27.
    Birch, A. J.: Biosynthetic Pathways. In Chemical Plant Taxonomy (Ed. T. Swain ), p. 141. London: Academic Press. 1963.Google Scholar
  28. 28.
    Birch, A. J., B. Milligan, E. Smith, and R. N. Speake: Some Stereochemical Studies of Lignans. J. Chem. Soc. ( London ) 1958, 4471.Google Scholar
  29. 29.
    Blair, G. E., J. M. Cassady, J. E. Robbers, V. E. Tyler, and R. F. Raffauf: Chemical Investigation of Virola Species. I. Isolation of 3,4’,5-Trimethoxy-trans- stilbene, Otobaene and Hydroxyotobain from Virola cuspidata. Phytochem. 8, 497 (1969).CrossRefGoogle Scholar
  30. 30.
    Blears, J. G., and R. D. Haworth: The Constituents of Natural Phenolic Resines. XXIV. A Synthesis of Galgravin. J. Chem. Soc. ( London ) 1958, 1985.Google Scholar
  31. 31.
    Bowden, B. F., E. Ritchie, and W. C. Taylor: Constituents of Eupomatia Species. II. Isolation and Structure Determination of Further Eupomatenoid Lignans from the Bark of Eupomatia laurina. Austral. J. Chem. 25, 2659 (1972).CrossRefGoogle Scholar
  32. 32.
    Braz Fº-., R., R. Figliuolo, O. R. Gottlieb, and J. G. S. Maia: Neolignans from Endlicheria verticillata (later classified as a Nectandra sp). Communication presented at the XXVIII Annual Meeting of Sociedade Brasileira para o Progresso da Ciencia, Brasilia (1976).Google Scholar
  33. 33.
    Braz Fº-., R., J. C. Mourão, O. R. Gottlieb, and J. G. S. Maia: Lanthanide Induced Shifts as Aid in the Structural Determination of Eusiderins. Tetrahedron Letters 1976, 1157.Google Scholar
  34. 34.
    Brophy, G. C., J. Mohandas, M. Slaytor, S. Sternhell, T. R. Watson, and L. A. Wilson: Novel Lignans from a Cinnamomum Sp. from Bougainville. Tetra­hedron Letters 1969, 5159.Google Scholar
  35. 35.
    Brown, D., and R. Stevenson: Synthesis of Dehydrootobain. J. Organ. Chem. (USA) 30, 1759 (1965).CrossRefGoogle Scholar
  36. 36.
    Bülow, M. V. von, N. C. Franca, O. R. Gottlieb, and A. M. Puentes Suarez: The Chemistry of Brazilian Lauraceae. XXIV. Guianin: a Neolignan from Aniba guianensis. Phytochem. 12, 1805 (1973).CrossRefGoogle Scholar
  37. 37.
    Burk, D., and M. Woods: Hydrogen Peroxide, Catalase, Glutathione Peroxidase, Quinones, Nor-dihydroguaiaretic Acid, and Phosphopyridine Nucleotides in Rela­tion to X-Ray Action on Cancer Cells. Radiation Res. Suppl. 3, 212 (1963); apud Chem. Abstr. 59, 1934 (1963).Google Scholar
  38. 38.
    Canonica, L., P. M. Manitto, P. Monti, and M. Sanchez A.: Biosynthesis of Allylphenols in Ocimum basilicum L. Chem. Commun. 1971, 1108.Google Scholar
  39. 39.
    Carnmalm, B.: The Absolute Configuration of Dihydroguaiaretic Acid. Chem. and Ind. 1956, 1093.Google Scholar
  40. 40.
    Carnmalm, B.: Absolute Configuration in the Lignan Series. Ark. Kemi 15, 215 (1960); apud Chem. Abstr. 55, 5367 (1961).Google Scholar
  41. 41.
    Chapman, O. L., M. R. Engel, J. P. Springer, and J. C. Clardy: The Total Synthesis of Carpanone. J. Amer. Chem. Soc. 93, 6696 (1971).CrossRefGoogle Scholar
  42. 42.
    Chen, Y.-P., M. Hong, H.-Y. Hsu, S. Yamamura, and Y. Hirata: Isolation and Struc­ture of Asatone. Tetrahedron Letters 1972, 1607.Google Scholar
  43. 43.
    Chen, Y.-P., R. Liu, and H.-Y. Hsu: The Structures and Conformations of Two New Lignans, Kadsurin and Kadsurarin. Tetrahedron Letters 1973, 4257.Google Scholar
  44. 44.
    Cousin, H., and H. Hérissey: Oxidation of Eugenol by Oxidizing Enzyme of Mushrooms and by Ferric Chloride; Obtention of Dehydrodi-eugenol. Bull. soc. chim. France Ser. 4, 3, 1066 (1908).Google Scholar
  45. 45.
    Cousin, H., and H. Hérissey: Oxidation of Isoeugenol. On Dehydrodi-isoeugenol. Bull. soc. chim. France Ser. 4, 3, 1070 (1908).Google Scholar
  46. 46.
    Cronquist, A.: The Evolution and Classification of Flowering Plants. London: Nelson. 1968.Google Scholar
  47. 47.
    Crosley, N. S., and C. Djerassi: Naturally Occurring Oxygen Heterocyclics. XI. Veraguensin. J. Chem. Soc. ( London ) 1962, 1459.Google Scholar
  48. 48.
    Dean, F. M.: Naturally Occurring Oxygen Ring Compounds, p. 41. London: Butterworths. 1963.Google Scholar
  49. 49.
    Dias, S. M., J. B. Fernandes, O. R. Gottlieb, and J. G. S. Maia: Neolignans from a Species of the Genus Aniba. Communication presented at the XXVII Annual Meeting of Sociedade Brasileira para o Progresso da Ciencia, Belo Horizonte (1975).Google Scholar
  50. 50.
    Donnelly, B. J., D. M. X. Donnelly, A. M. O’Sullivan, and J. P. Prendergast: Dalbergia Species. VII. The Isolation and Structure of Melanoxin, a New Dihydro- benzofuran from Dalbergia melanoxylon Guill. and Perr. (Leguminosae). Tetrahedron 25, 4409 (1969).CrossRefGoogle Scholar
  51. 51.
    Doskotch, R. W., and M. S. Flom: Acuminatin, a New Bis-Phenylpropide from Magnolia acuminata L. Tetrahedron 28, 4711 (1972).CrossRefGoogle Scholar
  52. 52.
    Erdtman, H.: Dehydrierungen in der Coniferylreihe. II. Dehydro-di-isoeugenol. Liebigs Ann. Chem. 503, 283 (1933).Google Scholar
  53. 53.
    Erdtman, H., and J. Runeberg: Phenol Dehydrogenations. VII. Dehydrogenation of Chavicol to Magnolol. Acta Chem. Scand. 11, 1060 (1957).CrossRefGoogle Scholar
  54. 54.
    Eskins, K., C. Glass, W. Rohwedder, R. Kleiman, and J. Sloneker: Dimers of Isoeugenol by Dye-Sensitized Photooxidation. Tetrahedron Letteis 1972, 861.Google Scholar
  55. 55.
    Fernandes, J. B., O. R. Gottlieb, and J. G. S. Maia: The Chemistry of Brazilian Lauraceae. XXXIV. Neolignans from an Aniba Species (later classified A. affinis). Phytochem. 15, 1033 (1976).CrossRefGoogle Scholar
  56. 56.
    Franca, N. C., O. R. Gottlieb, and J. G. S. Maia: The Chemistry of Brazilian Lauraceae. XXVII. Macrophyllin, a Neolignan from Licaria macrophylla. Phytochem. 13, 2839 (1974).CrossRefGoogle Scholar
  57. 57.
    Freudenberg, K., and K. Weinges: Systematik und Nomenklatur der Lignane. Tetrahedron 15, 115 (1961).CrossRefGoogle Scholar
  58. 58.
    Fujita, Y., and J. Shigenoi: Oxidation of Eugenol with Hydrogen Peroxide. Nippon Kagaku Zasshi 87, 1002 (1966); apud Chem. Abstr. 65, 18450 (1966).Google Scholar
  59. 59.
    Geissman, T. A., and D. H. Crout: Organic Chemistry of Secondary Plant Metabolism, p. 378. San Francisco: Freeman, Cooper & Co. 1969.Google Scholar
  60. 60.
    Gerchuk, M. P., and V. M. Ivanova: Synthesis of Nordihydroguaiaretic Acid and its Use as a Preservative of Edible Fats. Khim. Nauka i Prom. 3, 685 (1958); apud Chem. Abstr. 53, 7094 (1958).Google Scholar
  61. 61.
    Giesbrecht, A. M., N. C. Franca, O. R. Gottlieb, and A. I. da Rocha: The Chemistry of Brazilian Lauraceae. XXVI. The Neolignans of Licaria cartella. Phytochem. 13, 2285 (1974).CrossRefGoogle Scholar
  62. 62.
    Gilchrist, T., R. Hodges, and A. L. Porte: The Structure of Otobain. J. Chem. Soc. ( London ) 1962, 1780.Google Scholar
  63. 63.
    Gisvold, O., and E. Thaker: Lignans from Larrea divaricata. J. Pharm. Sci. 63, 1905 (1974).CrossRefGoogle Scholar
  64. 64.
    Gottlieb, O. R.: Chemosystematics of the Lauraceae. Phytochem. 11, 1537 (1972).CrossRefGoogle Scholar
  65. 65.
    Gottlieb, O. R.: Lignans and Neolignans. Revista Latinoamericana de Quimica 5, 1 (1974).Google Scholar
  66. 66.
    Gottlieb, O. R., J. G. S. Maia, and J. C. MourÄo: The Chemistry of Brazilian Lauraceae. XXXVI. Neolignans from a Licaria species. Phytochem. 15, 1289 (1976).CrossRefGoogle Scholar
  67. 67.
    Gottlieb, O. R., J. G. S. Maia, and M. N. de S. Ribeiro: The Chemistry of Brazilian Myristicaceae. VII. Neolignans from Virola cannata. Phytochem. 15, 773 (1976).CrossRefGoogle Scholar
  68. 68.
    Gottlieb, O. R., M. C. Marx, and C. M. A. da M. Rezende: Proposals concerning the Biosynthesis of Phenylpropanoids. Communication presented at the XXVII Annual Meeting of Sociedade Brasileira para o Progresso da Ciència, Belo Horizonte (1975).Google Scholar
  69. 69.
    Gottlieb, O. R., M. L. da Silva, and Z. S. Ferreira: The Chemistry of Brazilian Lauraceae. XXXI. Neolignans from Aniba terminalis. Phytochem. 14, 1825 (1975).CrossRefGoogle Scholar
  70. 70.
    Gottlieb, O. R., J. C. Mourao, M. Yoshida, R. D. Rosenstein, and K. Tomita: Unpublished work (1976).Google Scholar
  71. 71.
    Govindachari, T. R., K. Nagarajan, N. Viswanathan, and H. Fuhrer: Non- equivalence of Methylenedioxy Protons in Cyclolignans. Indian J. Chem. 9, 546 (1971).Google Scholar
  72. 72.
    Gregson, M., W. D. Ollis, B. T. Redman, I. O. Sutherland, and H. H. Dietrichs: The Constitution and Stereochemistry of Obtusafuran. Chem. Commun. 1968, 1394.Google Scholar
  73. 73.
    Haworth, R. D.: Natural Resins. Annu. Rep. Progr. Chem. 33, 266 (1937).Google Scholar
  74. 74.
    Haworth, R. D.: The Chemistry of the Lignan Group of Natural Products. J. Chem. Soc. ( London ) 1942, 448.Google Scholar
  75. 75.
    Haworth, R. D., C. R. Mavin, and G. Sheldrick: The Constituents of Guaiacum Resin. II. Synthesis of dl-Guaiaretic Acid Dimethyl Ether. J. Chem. Soc. ( London ) 1934, 1423.Google Scholar
  76. 76.
    Hayashi, T., and R. H. Thomson: New Lignans in Conocarpus erectus. Phytochem. 14, 1085 (1975).CrossRefGoogle Scholar
  77. 77.
    Haynes, C. G., A. H. Turner, and W. A. Waters: The Oxidation of Monohydric Phenols by Alkaline Ferricyanide. J. Chem. Soc. ( London ) 1956, 2823.Google Scholar
  78. 78.
    Hearon, W. M., and W. S. Macgregor: The Naturally Occurring Lignans. Chem. Rev. 55, 958 (1955).CrossRefGoogle Scholar
  79. 79.
    Herrmann, K.: The Lignans and their Practical Significance. Pharmazie 12, 147 (1957).Google Scholar
  80. 80.
    Hobbs, J. J., and F. E. King: The Chemistry of Extractives from Hardwoods. XXIX. Eusiderin, a Possible By-product of Lignin Synthesis in Eusideroxylon zwageri. J. Chem. Soc. ( London ) 1960, 4732.Google Scholar
  81. 81.
    Holloway, D. M., and F. Scheinmann: Co-occurrence of Aporphine and Biphenyl Constituents in Litsea turfosa. Phytochem. 12, 1503 (1973).CrossRefGoogle Scholar
  82. 82.
    Holloway, D. M., and F. Scheinmann: Two Lignans from Litsea grandis and L. gracilipes. Phytochem. 13, 1233 (1974).CrossRefGoogle Scholar
  83. 83.
    Hughes, G. K., and E. Ritchie: The Chemical Constituents of Himantandra Species. I. The Lignans of Himantandra baccata and H. belgraveana. Austral. J. Chem. 7, 104 (1954).Google Scholar
  84. 84.
    Jewers, K., A. H. Manchanda, and H. M. Rose: Naturally-occurring Antitumour Agents. In Progress in Medicinal Chemistry (Edited by G. P. Ellis and G. B. West), Vol.9, p. 33. London: Butterworths. 1971.Google Scholar
  85. 85.
    King, F. E., and J. G. Wilson: The Chemistry of Extractives from Hardwoods. XXXVI. The Lignans of Guaiacum officinale L. J. Chem. Soc. ( London ) 1964, 4011.Google Scholar
  86. 86.
    King, F. E., and J. G. Wilson: The Chemistry of Extractives from Hardwoods. XXXVII. The Synthesis of Furoguaiacin Ethers. J. Chem. Soc. ( London ) 1965, 1572.Google Scholar
  87. 87.
    Klyne, W., R. Stevenson, and R. J. Swan: Optical Rotatory Dispersion. XXVIII. Absolute Configuration of Otobain and Derivatives. J. Chem. Soc. ( C) (London ) 1966, 893.Google Scholar
  88. 88.
    Kohen, F., I. Maclean, and R. Stevenson: The Constitution of Otobaphenol. J. Chem. Soc. ( C) (London ) 1966, 1775.Google Scholar
  89. 89.
    Kotchetkov, N. K., A. Ya. Khorlin, and O. S. Chizhov: Chemical Study of Schizandra chinensis. I. Schizandrin and Related Compounds. Zhurn. Obshchei Khimii (USSR) 31, 3454 (1961); apud Chem. Abstr. 57, 3334 (1962).Google Scholar
  90. 90.
    Kotchetkov, N. K., A. Ya. Khorlin, O. S. Chizhov, and V. I. Sheichenko: Chemical Study of Schizandra chinensis. II. The Structure of Schizandrine. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 850 (1962); apud Chem. Abstr. 57, 13704 (1962).Google Scholar
  91. 91.
    Kotchetkov, N. K., A. Ya. Khorlin, and O. S. Chizhov: Chemical Study of Schizandra chinensis. III. Synthesis and Ultraviolet Spectra of Some Derivatives of 2,3,4,2’, 3’,4’-hexamethoxybipheny 1. Izv. Akad. Nauk SSSR, Otd. Khim. Nauk 856 (1962); apud Chem. Abstr. 57, 13704 (1962).Google Scholar
  92. 92.
    Kotchetkov, N. K., A. Ya. Khorlin, and O. S. Chizhov: Chemical Study of Schizandra chinensis. IV. Isolation, Structure and Synthesis of Deoxyschizandrine and the Structure of γ-Schizandrine. Izv. Akad. Nauk SSSR, Ser. Khim. [6], 1036 (1964); apud Chem. Abstr. 61, 8250 (1964).Google Scholar
  93. 93.
    Kotchetkov, N. K., A. Ya. Khorlin, and O. S. Chizhov: Deoxyschizandrin — Structure and Total Synthesis. Tetrahedron Letters 1962, 361.Google Scholar
  94. 94.
    Kotchetkov, N. K., A. Ya. Khorlin, O. S. Chizhov, and V. I. Sheichenko: Schizandrin — Lignan of Unusual Structure. Tetrahedron Letters 1961, 730.Google Scholar
  95. 95.
    Krukoff, B. A.: American Species of Strychnos. Lloydia 35, 197 (1972).Google Scholar
  96. 96.
    Labán, E. A.: Extraction and Assay of Nordihydroguaretic Acid in Larrea nitida. Tesis quim. Univ. Chile 2, 17 (1950); apud Chem. Abstr. 47, 7126 (1953).Google Scholar
  97. 97.
    Lebedev, A. A., and I. K. Kamilov: Schizandrin Pharmacology. Med. Zh. Uzb. 1966 (9), 60; apud Chem. Abstr. 66, 74744 (1967).Google Scholar
  98. 98.
    Lindberg, B.: Dehydrogenation of Phenols. VII. Dehydroguaiaretic Acid by Dehydrogenation of Isoeugenol. Svensk Papperstidn. 56, 6 (1953); apud Chem. Abstr. 49, 6866 (1955).Google Scholar
  99. 99.
    Maclean, I., and R. Stevenson: Synthesis of (±)-Otobain. J. Chem. Soc. ( C) (London ) 1966, 1717.Google Scholar
  100. 100.
    Majumder, P. L., and M. Bhattacharyya: Structure of Furoguaiacidin: a New Furanoid Lignan of the Heartwood of Guaiacum officinale L. Chem. and Ind. 1974, 77.Google Scholar
  101. 101.
    Majumder, P. L., A. Chatterjee, and G. C. Sengupta: Lignans from Machilus edulis. Phytochem. 11, 811 (1972).CrossRefGoogle Scholar
  102. 102.
    Manitto, P., D. Monti, and P. Gramatica: Biosynthesis of Anethole in Pimpinella anisum L. Tetrahedron Letters 1974, 1567.Google Scholar
  103. 103.
    Marx, M. C.: Arylpropanoids in Embryobionta. M. S. thesis presented to Uni- versidade Federal Rural do Rio de Janeiro (1975).Google Scholar
  104. 104.
    Matsui, K., and K. Munakata: The Structure of Piperenone, a New Antifeeding Substance from Piper futokadzura. Tetrahedron Letters 1975, 1905.Google Scholar
  105. 105.
    McAlpine, J. B., N. V. Riggs, and P. G. Gordon: Absolute Stereochemistry of Calopiptin. Austral. J. Chem. 21, 2095 (1968).CrossRefGoogle Scholar
  106. 106.
    McCredie, R. S., E. Ritchie, and W. C. Taylor: Constituents of Eupomatia Species. The Structure and Synthesis of Eupomatene. A Lignan of Novel Type from Eupomatia laurina R. Br. Austral. J. Chem. 22, 1011 (1969).CrossRefGoogle Scholar
  107. 107.
    McKechnie, J. S., and I. C. Paul: Molecular Structure of Nordihydroguaiaretic Acid. J. Chem. Soc. ( B) (London ) 1969, 699.Google Scholar
  108. 108.
    McMurry, T. B. H., and H. K. Kennedy-Skipton: A Synthesis of (±)-Otobain. Tetrahedron Letters 1966, 975.Google Scholar
  109. 109.
    Merlini, L., and A. Zanarotti: A Biogenetically Patterned Synthesis of (±)-Eusi- derin. Tetrahedron Letters 1975, 3621.Google Scholar
  110. 110.
    Meyer, W.: Podophyllum peltatum — May Apple. A Potential New Cash-Crop Plant of Eastern North America. Economic Botany 28, 68 (1974).CrossRefGoogle Scholar
  111. 111.
    Miller, I. J.: The Dimerization of Isoeugenol by Free Radicals. Tetrahedron Letters 1972, 4955.Google Scholar
  112. 112.
    Murphy, S. T., E. Ritchie, and W. C. Taylor: Some Constituents of Austrobaileya scandens (Austrobaileyaceae): Structures of Seven New Lignanes. Austral. J. Chem. 28, 81 (1975).CrossRefGoogle Scholar
  113. 113.
    Nasirov, S. Kh., A. A. Lebedev, N. A. Ishmukhamedov, and I. K. Kamilov: Electrophysiological Analysis of the Schizandrin Effect on the Central Nervous System. Med. Zh. Uzb. 1967 (5), 34; apud Chem. Abstr. 68, 20792 (1968).Google Scholar
  114. 114.
    Ogiso, A., M. Kurabayashi, H. Mishima, and M. C. Woods: The Structure of Futoenone, a Novel Spiro-cyclohexadienone Derivative. Tetrahedron Letters 1968, 2003.Google Scholar
  115. 115.
    Ogiso, A., M. Kurabayashi, S. Takahashi, H. Mishima, and M. C. Woods: The Structure and Total Synthesis of Futoenone, a Constituent of Piper futokadzura Sieb. et Zucc. Chem. Pharm. Bull. (Japan) 18, 105 (1970).CrossRefGoogle Scholar
  116. 116.
    Ohta, T., and Y. Mori: Oxidation of p-Propylphenol with Hydrogen Peroxide. Ann. Rept. Tokyo Coll. Pharm. 3, 206 (1953); apud Chem. Abstr. 49, 7513 (1955).Google Scholar
  117. 117.
    Oliveto, E. P.: Nordihydroguaiaretic Acid. A Naturally Occurring Antioxidant. Chem. and Ind. 1972, 677.Google Scholar
  118. 118.
    Pardini, R. S., J. C. Heidker, and D. C. Fletcher: Inhibition of Mitochondrial Electron Transport by Nor-Dihydroguaiaretic Acid (NDGA). Biochem. Pharmac. 19, 2695 (1970).CrossRefGoogle Scholar
  119. 119.
    Pearl, I. A.: 2,3-Bis(hydroxybenzyl)butane Derivatives. US Pat. 2,644,822 (1953); apud Chem. Abstr. 48, 6468 (1954).Google Scholar
  120. 120.
    Pelter, A., A. P. Stainton, and M. Barber: The Mass Spectra of Oxygen Heterocycles. III. An Examination of Simple Lignans. J. Heterocycl. Chem. 3, 191 (1966).CrossRefGoogle Scholar
  121. 121.
    Perry, C. W., M. V. Kalnins, and K. H. Deitcher: Synthesis of Lignans. Nordihydroguaiaretic Acid. J. Organ. Chem. (USA) 37, 4371 (1972).CrossRefGoogle Scholar
  122. 122.
    Picker, K., E. Ritchie, and W. C. Taylor: Constituents of Eupomatia Species. III. New Eupomatenoid Lignans from the Leaves and Wood of Eupomatia laurina. Austral. J. Chem. 26, 1111 (1973).CrossRefGoogle Scholar
  123. 123.
    Redman, B. T.: Phytochemical Studies in the Leguminosae and the Guttiferae Families. Ph. D. thesis, p. 86, University of Sheffield (1968).Google Scholar
  124. 124.
    Riggs, N. V., and J. D. Stevens: Some Constituents of Piptocalyx moorei Oliv. Austral. J. Chem. 15, 305 (1962).CrossRefGoogle Scholar
  125. 125.
    Runeberg, J.: Phenol Dehydrogenations. VIII. Synthesis of Magnolol. Acta Chem. Scand. 12, 188 (1958).CrossRefGoogle Scholar
  126. 126.
    Ruth, E. F.: Isolation of nor-Dihydroguaiaretic Acid from Argentinian Larrea Species. Anales asoc. quim. Argentina 34, 163 (1946).Google Scholar
  127. 127.
    Sarkanen, K. V.: In: Lignins, Occurrence, Formation, Structure and Reactions (Eds. K. V. Sarkanen and C. H. Ludwig), p. 95. New York: Wiley-Interscience. 1971.Google Scholar
  128. 128.
    Sarkanen, K. V., and A. F. A. Wallis: Stereospecific Formation of trans-Phenyl- coumarans by Dehydrogenative Dimerization of trans- and cis-Isoeugenol. Chem. Commun. 298 (1969).Google Scholar
  129. 129.
    Sarkanen, K. V., and A. F. A. Wallis: Oxidative Dimerizations of (E)- and (Z)-Isoeugenol (2-Methoxy-4-propenyl-phenol) and (E)- and (Z)-2,6-Dimethoxy-4-propenylphenol. J. Chem. Soc. Perkin I (London) 1973, 1869.Google Scholar
  130. 130.
    Sarkanen, K. V., and A. F. A. Wallis: PMR Analysis and Conformation of 2,5-bis-(,34,5-Trimethoxyphenyl)-3,4-di- methyitetrahydrofuran Isomers. I. J. Heterocycl. Chem. 10, 1025 (1973).CrossRefGoogle Scholar
  131. 131.
    Sasaki, K., Y. Hirata, S. Yamamura, Y.-P. Chen, M. Hong, and H.-Y. Hsu: The Isolation and Structure of Isoasatone. Tetrahedron Letters 1973, 4881.Google Scholar
  132. 132.
    Schrecker, A. W.: Meso-Dihydroguaiaretic Acid and its Derivatives. J. Amer. Chem. Soc. 79, 3823 (1957).CrossRefGoogle Scholar
  133. 133.
    Schrecker, A. W., and J. L. Hartwell: Application of Tosylate Reductions and Molecular Rotations to the Stereochemistry of Lignans. J. Amer. Chem. Soc. 77, 432 (1955).CrossRefGoogle Scholar
  134. 134.
    Schrecker, A. W., and J. L. Hartwell: Components of Podophyllin. XX. The Absolute Configuration of Podophyllotoxin and Related Lignans. J. Organ. Chem. (USA) 21, 381 (1956).CrossRefGoogle Scholar
  135. 135.
    Schrecker, A. W., and J. L. Hartwell: The Absolute Configuration of Lignans. J. Amer. Chem. Soc. 79, 3827 (1957).CrossRefGoogle Scholar
  136. 136.
    Shipochliev, T., and St. Iilieva: Pharmacologic Study of Bulgarian Schizandra chinensis. Farmatsiya (Sofia) 17, 56 (1967); apud Chem. Abstr. 68, 1870 (1968).Google Scholar
  137. 137.
    Sugimoto, N., and K. Okumura: Nordihydroguaiaretic Resin Acid. Japan. Pat. 4626 (1954); apud Chem. Abstr. 50, 4225 (1956).Google Scholar
  138. 138.
    Sugii, Y.: Constituents of the Bark of Magnolia officinalis Rhed. et Wils, and Magnolia obovata Thumb. J. Pharmac. Soc. Japan 50, 183 (1930); apud Chem. Abstr. 24, 3505 (1930).Google Scholar
  139. 139.
    Takahashi, S., and A. Ogiso: The Structure of Futoquinol, a Constituent of Piper futokadzura Sieb, et Zucc. Chem. Pharm. Bull. (Japan) 18, 100 (1970).CrossRefGoogle Scholar
  140. 140.
    Titlyanov, A. A.: Biologically Active Substances of Chinese Magnolia Vine Fruit. Tr. Vses. Semin. Biol. Aktiv. (Lech.) Veshchestvam Plodov Yagod (Edited by L. I. Vigorov, Ural. Lesotekh. Inst., Sverdlovsk, USSR), 3rd ed., p. 363 (1966, publ. 1968); apud Chem. Abstr. 73, 91186 (1970).Google Scholar
  141. 141.
    Volicer, L., M. Sramka, I. Janku, R. Capek, R. Smetana, and V. Ditteova: Some Pharmacological Effects of Schizandra chinensis. Arch. Intern. Pharmacodyn. Ther. 163, 249 (1966); apud Chem. Abstr. 66, 1413 (1967).Google Scholar
  142. 142.
    Wallace, R., A. L. Porte, and R. Hodges: Lignans from Myristica otoba. The Structures of Hydroxyotobain and Iso-otobain. J. Chem. Soc. ( London ) 1963, 1445.Google Scholar
  143. 143.
    Waller, C. W., and O. Gisvold: A Phytochemical Investigation of Larrea divaricata Cav. J. Am. Pharm. Assoc. 34, 78 (1945).Google Scholar
  144. 144.
    Wenkert, E., H. E. Gottlieb, O. R. Gottlieb, M. O. da S. Pereira, and M. D. Formiga: Carbon-13 Nuclear Magnetic Spectroscopy of Naturally Occurring Substances. XLV. 13C NMR Spectroscopy of Neolignans. Phytochem. 15, 1547 (1976).Google Scholar
  145. 145.
    Woods, M. C., I. Miura, A. Ogiso, M. Kurabayashi, and M. Mishima: The NMR Spectra of Futoenone and Derivatives: Partial Decoupling as an Aid in the Assignment of Complex Spectra, and Further Observations of Overhauser Effects. Tetrahedron Letters 1968, 2009.Google Scholar
  146. 146.
    Yamamura, S., K. Sasaki, Y. Hirata, Y.-P. Chen, and H.-Y. Hsu: Further Studies on Isoasatone. Tetrahedron Letters 1973, 4877.Google Scholar
  147. 147.
    Yamamura, S., Y. Terada, Y.-P. Chen, H.-Y. Hsu, and Y. Hirata: Photochemical Conversion of Asatone to Isoasatone. The Revised Structure of Asatone. Tetrahedron Letters 1975, 1903.Google Scholar
  148. 148.
    Aiba, C. J., M. A. de Alvarenga, O. Castro C., A. M. Giesbrecht, O. R. Gottlieb, and F. M. Pagliosa: The Chemistry of Brazilian Lauraceae. XXXIX. Benzofuranoid Neolignans from Aniba simulans. Phytochem. 16, 741 (1977).Google Scholar
  149. 149.
    Aiba, C. J., O. R. Gottlieb, F. M. Pagliosa, M. Yoshida, and M. T. Magalhaes: The Chemistry of Brazilian Lauraceae. XXXVII. Neolignans from Nectandra miranda. Phytochem. 16, 745 (1977).CrossRefGoogle Scholar
  150. 150.
    Alvarenga, M. A. de, U. Brocksom, O. Castro C., O. R. Gottlieb, and M. T. Magalhães: The Chemistry of Brazilian Lauraceae. XLIV. Neolignans from Aniba burchellii. Phytochem. 16 (1977).Google Scholar
  151. 151.
    Alvarenga, M. A. de, O. Castro C., A. M. Giesbrecht, and O. R. Gottlieb: The Chemistry of Brazilian Lauraceae. XLV. Bicyclo [3,2,l]octanoid Neolignans from Aniba simulans. Phytochem. 16 (1977).Google Scholar
  152. 152.
    Diaz, A. M. P. de, O. R. Gottlieb, A. F. Magalhaes, E. G. Magalhaes, and J. G. S. Maia: The Chemistry of Brazilian Lauraceae. XLVI. Notes on Aniba Species. Acta Amazonica 7, 41 (1977).Google Scholar
  153. 153.
    Forrest J. E., R. A. Heacock, and J. P. Forrest: Diarylpropanoids from Nutmeg and Mace (Myristica fragrans Houtt.). J. Chem. Soc. Perkin I (London) 1974, 205.Google Scholar
  154. 154.
    Ghera, E., Y. Ben-David, and D. Becker: Desoxyschizandrin, Stereochemistry and Total Synthesis. Tetrahedron Letters 1977, 463.Google Scholar
  155. 155.
    Gottlieb, O. R., J. C. Mourão, M. Yoshida, Y. P. Mascarenhas, M. Rodrigues, R. D. Rosenstein, and K. Tomita: The Chemistry of Brazilian Lauraceae. XLIII. Absolute Configuration of the Benzofuranoid Neolignans. Phytochem. 16,1003(1977).Google Scholar
  156. 156.
    Ikeya, Y., H. Taguchi, and Y. Iitaka: The Constituents of Schizandra chinensis Baill. The Structure of a New Lignan, Gomisin D. Tetrahedron Letters 1976, 1359.Google Scholar
  157. 157.
    Taguchi, H., and Y. Ikeya: The Constituents of Schizandra chinensis Baill. I. The Structures of Gomisin A, B and C. Chem. Pharm. Bull. (Japan) 23, 3296 (1975).CrossRefGoogle Scholar
  158. 158.
    Yamamura, S., Y.-P. Chen, H.-Y. Hsu, and Y. Hirata: Asatone in Plants of the Aristolochiaceae. Phytochem. 15, 426 (1976).CrossRefGoogle Scholar
  159. 159.
    Yamamura, S., Y. Terada, Y.-P. Chen, M. Hong, H.-Y. Hsu, K. Sasaki, and Y. Hirata: The Structures of Two Novel Neolignans, Asatone and Isoasatone. Bull. Chem. Soc. Japan 49, 1940 (1976).CrossRefGoogle Scholar

Copyright information

© Springer-Verlag/Wien 1978

Authors and Affiliations

  • O. R. Gottlieb
    • 1
  1. 1.University of São PauloBrasil

Personalised recommendations