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Abstract

The homoisoflavanones belong to a small family of natural products whose first member was isolated by Boehler and Tamm in 1967 from bulbs of Eucomis bicolor Bak. (9). Their discovery resulted from a systematic chemical analysis of Liliaceae for cardiac glycosides. However, unlike the botanically closely related Urginea maritima (L.) Bak. (Squill) and some species of Scilla, Ornithogalum and Dipcadi (33), Eucomis plants did not contain even traces of these compounds.

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References

  1. Andermatt, P.: Beitrag zur Kenntnis der Biogenese der Spirostanole und Untersuchungen über die Biogenese der Homo-Isoflavone. Ph. D. Thesis, Basel 1971.

    Google Scholar 

  2. Andrieux, J., D. H. R. Barton, and H. Patin: Rhodium-catalyzed Isomerization of Some Unsaturated Organic Substrates. J. C. S. Perkin I, 1977, 359.

    Google Scholar 

  3. Antenuis, M., and D. TA Vernier: New Models for Conformational Analysis by Nuclear Magnetic Resonance. Tetrahedron Letters 1964, 3949.

    Google Scholar 

  4. Audier, H.: Etude des Composés Flavoniques par Spectrométrie de masse. Bull. Soc. Chim. France 1966, 2892.

    Google Scholar 

  5. Baldwin, R. M., C. D. Snyder, and H. Rapoport: Biosynthesis of Menaquinones. Dissymmetry in the Napththalenic Intermediate. J. Amer. Chem. Soc. 95, 276 (1973).

    Article  CAS  Google Scholar 

  6. Barker, S. A., J. Homer, M. C. Keith, and L. F. Thomas: Proton Resonance Studies of Methoxy and Acetoxy Derivatives of Pyranose Molecules Applied to the Conformation of Methyl 3-O-Carbamoyl-a- and -ß-L-novioside. J. Chem. Soc. 1963, 1538.

    Google Scholar 

  7. Bass, R. J.: Synthesis of Chromones by Cyclization of 2-Hydroxyphenyl Ketones with Boron Trifluoride-Diethyl Ether and Methanesulphonyl Chloride. J. C. S. Chem. Commun. 1976, 78.

    Google Scholar 

  8. Boehler, P.: Isolierung und Strukturaufklärung der Homo-Isoflavone Eucomol und Eucomin. Ph. D. Thesis, Basel 1967.

    Google Scholar 

  9. Boehler, P., and CH. Tamm: The Homo-Isoflavones: A New Class of Natural Products. Isolation and Structure of Eucomin and Eucomol. Tetrahedron Letters 1967, 3479.

    Google Scholar 

  10. Budzikiewicz, H., C. Djerassi, and D. H. Williams: “Mass Spectrometry of Organic Compounds”, p. 470. San Francisco, Cambridge, London, Amsterdam: Holden-Day. 1967.

    Google Scholar 

  11. Caldicott, A. B., and G. Eglinton: Surface Waxes in “Phytochemistry” (ed. L. P. Miller), Vol. 3, p. 162. New York, Cincinnati, Toronto, London, Melbourne: Van Nostrand Reinhold. 1973.

    Google Scholar 

  12. Chari, V. M., and H. Wagner: Advances in the Spectroscopy of Plant Phenolics. Recent Adv. Phytochemistry 12, 29 (1979).

    Google Scholar 

  13. Chatterjea, J. N., S. C. Shaw, and J. N. Singh: A Synthesis of Anhydrobrazilic Acid. Isomerization of Arylidenechroman-4-ones to Homoisoflavones. J. Indian Chem. Soc. 51, 281 (1974).

    CAS  Google Scholar 

  14. Craig, J. C., A. R. Naik, R. Pratt, E. Johnson, and N. S. Bhacca: Nuclear Magnetic Resonance Spectra and Stereochemistry of the Antibacterial Principle from Haematoxylon braziletto. J. Org. Chemistry 30, 1573 (1965).

    Article  CAS  Google Scholar 

  15. Dann, O., and H. Hofmann: Die Epoxydation von 3-Benzylidenchromanonen-(4) zu 3,a-Oxido-3-benzyl-chromanonen-(4). Chem. Ber. 95, 1446 (1962).

    Article  CAS  Google Scholar 

  16. Dann, O.:Die Synthese von (±)-Haematoxylin. Chem. Ber. 98, 1498 (1965).

    Article  CAS  Google Scholar 

  17. Deulofeu, V., and T. J. Guerrero: N-Methyl-3.4-Dihydroxyphenylalanine. Org. Synth. Coll. Vol. 3, 586 (1955).

    Google Scholar 

  18. Dewick, P. M.: Biosynthesis of the 3-Benzylchroman-4-one Eucomin. J. C. S. Chem. Commun. 1973, 438.

    Google Scholar 

  19. Dewick, P. M.: Biosynthesis of the 3-Benzylchroman-4-one Eucomin in Eucomis bicolor. Phytochemistry 14, 983 (1975).

    Article  CAS  Google Scholar 

  20. Donnelly, D. M. X.: Neoflavonoids in “The Flavonoids” (eds. J. B. Harborne, T. J. Mabry, and H. Mabry), p. 801. London: Chapman and Hall. 1975.

    Google Scholar 

  21. Drewes, S. E.: Chroman and Related Compounds. Vol. 2 of Progress in Mass Spectroscopy (ed. H. Budzikiewicz ). Weinheim/Bergstrasse: Verlag Chemie. 1974.

    Google Scholar 

  22. Duddeck, H., G. Snatzke, and S. S. Yemul: 13C NMR and CD of Some 3,8-Bi- flavonoids from Garcinia Species and of Related Flavanones. Phytochemistry 17, 1369 (1978).

    Article  CAS  Google Scholar 

  23. Farkas, L., A. Gottsegen, and M. Nogradi: Synthesis of Eucomin and (±)- Eucomol. Tetrahedron Letters 1968, 4099.

    Google Scholar 

  24. Farkas, L., A. Gottsegen, and M. Nogradi: The Synthesis of Eucomin and (+)-Eucomol. Tetrahedron 26, 2787 (1970).

    Article  CAS  Google Scholar 

  25. Farkas, L., A. Gottsegen, M. Nogradi, and J. Strelisky: Synthesis of Homoisoflavanones-II. Constituents of Eucomis autumnalis and E. punctata. Tetrahedron 27, 5049 (1971).

    Article  CAS  Google Scholar 

  26. Finckh, R. E.: Isolierung und Strukturaufklärung homoisoflavonoider Verbindungen aus Eucomis punctata L’Herit. Ph. D. Thesis, Basel 1970.

    Google Scholar 

  27. Finckh, R. E., and CH. Tamm: The Homoisoflavones III. Isolation and Structure of Punctatin, 3,9-Dihydropunctatin, 4-0-Methyl-3,9-dihydropunctatin, 4-Demethyl- eucomin, and 4-Demethyl-5-0-methyl-3,9-dihydroeucomin. Experientia 26, 472 (1970).

    Article  CAS  Google Scholar 

  28. Friend, J.: Phenolic Substances and Plant Disease. Recent Adv. Phytochemistry 12, 557 (1979).

    Google Scholar 

  29. Grisebach, H.: Personal communication.

    Google Scholar 

  30. Grisebach, H., and J. Ebel: Phytoalexine, chemische Abwehrstoffe höherer Pflanzen? Angew. Chem. 90, 668 (1978).

    CAS  Google Scholar 

  31. Grisebach, H., and W. D. Ollis: Biogenetic Relationship Between Coumarins, Flavonoids, Isoflavonoids, and Rotenoids. Experientia 17, 4 (1961).

    Article  CAS  Google Scholar 

  32. a. Gross, D.: Phytoalexine und verwandte Pflanzenstoffe. Fortschr. Chem. Org. Naturst. 34, 187 (1977). Wien, New York: Springer.

    Google Scholar 

  33. Hahlbrock, K., and H. Grisebach: Biosynthesis of Flavonoids in “The Flavonoids” (eds. J. B. Harborne, T. J. Mabry, and H. Mabry), p. 905. London: Chapman and Hall. 1975.

    Google Scholar 

  34. Hegnauer, R.: Chemotaxonomie der Pflanzen, Vol. 2, p. 329. Basel und Stuttgart: Birkhäuser. 1963.

    Google Scholar 

  35. Heller, W.: Über einige Inhaltsstoffe von Eucomis punctata L’Herit. Isolierung, Konstitution und Synthese von (-)-R-Eucominsäure. Ph. D. Thesis, Basel 1973.

    Google Scholar 

  36. Heller, W., and CH. TAMM: Unpublished results.

    Google Scholar 

  37. Heller, W., and CH. TAMM: Isolierung, Konstitution und Synthese der (R)-(-)-Eucominsäure. Helv. Chim. Acta 57, 1766 (1974).

    Article  CAS  Google Scholar 

  38. 5,7-Dihydroxy-8-methoxychroman-4-on aus dem Zwiebelwachs von Eucomis comosa. Helv. Chim. Acta 61, 1257 (1978).

    Article  Google Scholar 

  39. Heller, W., P. Andermatt, W. A. Schaad, and CH. Tamm: Homoisoflavanone IV. Neue Inhaltsstoffe der Eucomin-Reihe von Eucomis bicolor. Helv. Chim. Acta 59, 2048 (1976).

    Article  CAS  Google Scholar 

  40. Jay, M., J.-F. Gönnet, E. Wollenweber, and B. Voirin: Sur L’Analyse Qualitative des Aglycones Flavoniques dans une Optique Chimitaxonomique. Phytochemistry 14, 1605 (1975).

    Article  CAS  Google Scholar 

  41. Kirby, G. W., and L. Ogunkoya: Deuterium and Tritium Exchange Reactions of Phenols and the Synthesis of Labelled 3,4-Dihydrophenylalanines. J. Chem. Soc. 1965, 6914.

    Google Scholar 

  42. Kirkiacharian, B. S.: Sur une Nouvelle Synthèse de la (+)-Triméthylbraziline. C. R. Acad. Sei. Ser. C 274, 2096 (1972).

    CAS  Google Scholar 

  43. Kirkiacharian, B. S.: Hydroborations: New Routes to Isoflavanones and Homoisoflavanones. J. C. S. Chem. Commun. 1975, 162.

    Google Scholar 

  44. Kirkiacharian, B. S., and M. Garnier: Hydroborations. Sur une Nouvelle Synthèse de la (±)-Tétraméthylhématoxyline. C. R. H. Acad. Sei. Ser. C 277, 1037 (1973).

    CAS  Google Scholar 

  45. Kouno, I., T. Komori, and T. Kawasaki: Zur Struktur der neuen Typen Homo-isoflavanone aus Bulben von Scilla scilloides Druce. Tetrahedron Letters 1973, 4569.

    Google Scholar 

  46. Krishnamurty, H. G., B. Parkash, and I. R. Seshadri: Synthesis of Eucomin, 4,-Demethyleucomin and 5,7-Di-O-methyleucomol. Indian J. Chemistry 12, 554 (1974).

    CAS  Google Scholar 

  47. Mcomie, J. F. W., M. L. Watts, and D. D. West: Demethylation of Aryl Methyl Ethers by Boron Tribromide. Tetrahedron 24, 2289 (1968).

    Article  CAS  Google Scholar 

  48. Markham, K. R.: Gentian Pigments-II. Xanthones from Gentiana bellidifolia. Tetra-hedron 21, 1449 (1965).

    Article  CAS  Google Scholar 

  49. Markham, K. R., and T. J. Mabry: Ultraviolet-Visible and Proton Magnetic Resonance Spectroscopy of Flavonoids in “The Flavonoids” (eds. J. B. Harborne, T. J. Mabry, and H. Mabry), p. 45. London: Chapman and Hall. 1975.

    Google Scholar 

  50. Martin, J. T.: Studies on the Natural Protective Covering of Plants: I. Plant Wax in Relation to Resistance to Infection by Fungi. Ann. Rep. Long Ashton Res. Sta. for 1956. 1957, 94.

    Google Scholar 

  51. Martin, J. T., and R. F. Batt: Studies on Plant Cuticule. I. The Waxy Coverings of Leaves. Ann. Appl. Biol. 46, 375 (1958).

    Article  CAS  Google Scholar 

  52. Masayuki, S., D. Difeo JR., N. Nakatani, B. Timmermann, and T. J. Mabry: Flavonoid Methyl Ethers on the External Leaf Surface of Larrea tridentata and L. divaricata. Phytochemistry 15, 727 (1976).

    Google Scholar 

  53. Massicot, J., and J.-P. Marthe: Résonance magnétique nucléaire de produits naturels. III. - Etude de quelques dérivés flavoniques et substances apparentées. Bull. Soc. Chim. France 1962, 1962.

    Google Scholar 

  54. Matthews, J. S.: Steroids-CCXXIII. Color Reagent for Steroids in Thin-Layer Chromatography. Biochim. Biophys. Acta 69, 163 (1963).

    Article  CAS  Google Scholar 

  55. Morsingh, F., and R. Robinson: The Synthesis of Brazilin and Haematoxylin. Tetrahedron 26, 281 (1970).

    Article  CAS  Google Scholar 

  56. Nielsen, H., and P. Arends: Structure of the Xantholignoid Kielcorin. Phytochemistry 17, 2040 (1978).

    Article  CAS  Google Scholar 

  57. Pelter, A., P. Stainton, and M. Barber: The Mass Spectra of Oxygen Heterocycles. II. The Mass Spectra of Some Flavonoids. J. Heterocyclic Chemistry 2, 262 (1965).

    Article  CAS  Google Scholar 

  58. Pelter, A., R. S. Ward, and R. J. Bass: The Carbon-13 Nuclear Magnetic Resonance Spectra of Isoflavones. J. C. S. Perkin 1 1978, 666.

    Article  Google Scholar 

  59. Pfeiffer, P., E. Breith, and H. Hoyer: Oxy-benzyl-chromanone. 11. Mitteilung zur Brasilin- und Haematoxylinfrage. J. prakt. Chemie 237, 31 (1931).

    Article  Google Scholar 

  60. Pratt, R., and Y. Yuzuriha: Antibacterial Activity of the Heartwood of Haematoxylon braziletto. J. Amer. Pharm. Assoc. 48, 69 (1959).

    Article  CAS  Google Scholar 

  61. Ravise, A., and B. S. Kirkiacharian: Influence de la structure de composés phénoliques sur l’inhibition du Phytophthora parasitica et d’enzymes participant aux processus parasitaires. III. Homoisoflavanones. Phythopath. Z. 92, 36 (1978), and references therein.

    Google Scholar 

  62. Reyneke, W. F.: N Monografiese Studie va die Genus Eucomis L’Hérit. in Suid- Afrika. M. Sc. Thesis, Pretoria 1972.

    Google Scholar 

  63. Robinson, R.: Chemistry of Brazilin and Haematoxylin. Bull. Soc. Chim. Fr. 1958, 125.

    Google Scholar 

  64. Robinson, R.: Brazilin and Haematoxylin in “Chemistry of Carbon Compounds” (ed. E. H. Rodd), Vol. IV, part B, p. 1005. New York: Elsevier. 1959.

    Google Scholar 

  65. Schaad, W.: Isolierung und Ermittlung der Konstitution neuer Homoisoflavanone aus Eucomis bicolor Bäk., Ph. D. Thesis, Basel 1977.

    Google Scholar 

  66. Sidwell, W. T. L., and CH. Tamm: The Homo-Isoflavones II: Isolation and Structure of 4’-0-Methylpunctatin, Autumnalin and 3,9-Dihydroautumnalin. Tetrahedron Letters 1970, 475.

    Google Scholar 

  67. Speta, F.: Über Chionodoxa Boiss., ihre Gliederung und Zugehörigkeit zu Scilla L., Naturk. Jahrb. Stadt Linz 1975, 21, 9 (1976).

    Google Scholar 

  68. Stahl, E.: Dünnschicht-Chromatographie, 2nd ed. p. 671. Berlin Heidelberg New York: Springer. 1967.

    Google Scholar 

  69. Stoessl, A.: Antifungal Compounds Produced by Higher Plants. Recent Adv. Phyto- chemistry 3, 143 (1970).

    CAS  Google Scholar 

  70. Tamm, CH.: Die Homo-isoflavone, eine neue Klasse von Naturstoffen. Arzneim. Forsch. (Drug Res.) 22, 1776 (1972).

    Google Scholar 

  71. Tronchet, J.: Flavone Derivatives of Fruits. Localization, Distribution and Evolution. Bull. Soc. Bot. Fr. 119, 25 (1972).

    CAS  Google Scholar 

  72. Tronchet, J.: Role of Protection and Control of Surface Flavonic Derivatives. First Experimental Results. Bull. Liaison, Groupe Polyphénols 48, 18 (1973).

    Google Scholar 

  73. Wagner, H., and L. Farkas: Synthesis of Flavonoids in “The Flavonoids” (eds. J. B. Harborne, T. J. Mabry, and H. Mabry), p. 202. London: Chapman and Hall. 1975.

    Google Scholar 

  74. Watt, J., and M. G. Breyer-Brandwijk: Medicinal and Poisonous Plants of Southern and Eastern Africa, 2nd edn., p. 298. Edinbourgh, London: E. S. Livingstone. 1962.

    Google Scholar 

  75. Weber, H. P., W. Heller, and CH. Tamm: Homoisoflavanones. V. Crystal and Molecular Structure of (-)-7-0-(p-Bromophenacyl)eucomol. The Absolute Configuration of (-)-Eucomol. Helv. Chim. Acta 60, 1388 (1977).

    CAS  Google Scholar 

  76. Wilson, R. G., J. H. Bowie, and D. H. Williams: Solvent Effects in NMR Spectroscopy. Solvent Shifts of Methoxyl Resonances in Flavones Induced by Benzene; an Aid in Structure Elucidation. Tetrahedron 24, 1407 (1968).

    Article  CAS  Google Scholar 

  77. Windholz, M. (ed.): The Merck Index, 9th edn. Rathway: Merck. 1976.

    Google Scholar 

  78. Wollenweber, E.: Flavonoidmuster als systematisches Merkmal in der Gattung Populus. Biochem. Syst. Ecol. 3, 35 (1975).

    Article  CAS  Google Scholar 

  79. Wollenweber, E.: Flavonoidexkret der Betulaceen. Biochem. Syst. Ecol. 3, 47 (1975).

    Article  CAS  Google Scholar 

  80. Wollenweber, E.: Einige Neufunde externer Flavonoide bei amerikanischen Farnen. Flora 168, 138 (1979).

    CAS  Google Scholar 

  81. Wollenweber, E., P. Lebreton, and M. Chandeson: Flavonoids in Bud Excretions of Prunus and Rhamnus Species. Z. Naturforsch. 27 b, 567 (1972).

    Google Scholar 

  82. Ziegler, R., and CH. Tamm: Isolation and Structure of Eucosterol and 16ß-Hydro- xyeucosterol, Two Novel Spirocyclic Nortriterpenes and of a New 24-Nor-5a-chola- 8,16-diene-23-oic Acid from Bulbs of Several Eucomis Species. Helv. Chim. Acta 59, 1997 (1976).

    Google Scholar 

  83. Recent Studies on Homoisoflavanones in “Flavonoids and Bioflavonoids”. Proc. 5th Hung. Biflavonoid Symposium, Matrafüred, Hungary, May 25–27, 1977, p. 95. Amsterdam, Oxford, New York: Elsevier Scientific Publ. Company. 1977.

    Google Scholar 

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Heller, W., Tamm, C. (1981). Homoisoflavanones and Biogenetically Related Compounds. In: Herz, W., Grisebach, H., Kirby, G.W. (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 40. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8611-4_3

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