Abstract
The isoflavonoids are natural phenolic compounds having in common the 1,2-diphenylpropane skeleton (1). Structurally and biogenetically they are closely related to the flavonoid compounds which are derivatives of 1,3-diphenylpropane (2).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
Similar content being viewed by others
References
Aghoramurthy, K., A.S. Kukla and T.R. Seshadri: Synthesis of a Racemate of Homopterocarpin. Current Sci. (India) 30, 218 (1961).
Ahluwalia, V.K., G.P. Sachdev and T.R. Seshadri: Chemical Components of Immature Green Pods of Dalbergia sissoo. Indian J. Chem. 3, 474 (1965).
Ahluwalia, V.K., G.P. Sachdev and T.R. Seshadri: Chemical Investigation of the Leaves of Ougeinia dalbergioides. Indian J. Chem. 4, 250 (1966).
Anirudhan, C.A. and W.B. Whalley: The Synthesis of “Maxima Substance C”. J. Chem. Soc. (London) 1963, 6049.
Arora, S.K., A.C. Jain and T.R. Seshadri: A New Synthesis of Afromosin. J. Indian Chem. Soc. 38, 61 (1961).
Arora, S.K., A.C. Jain and T.R. Seshadri: Synthesis of Tlatlancuayin. Tetrahedron 18, 559 (1962).
Audier, H.: Études des Composés Flavoniques par Spectrométrie de masse. Bull. Soc. Chim. France 1966, 2892.
Balakrishna, S., J.D. Ramanathan, T.R. Seshadri and B. Venkataramani: Special Chemical Components of the Heartwood of Ougeinia dalbergioides Linn. Proc. Roy. Soc. (London) A 268, 1 (1962).
Banerji, A., V.V.S. Murti and T.R. Seshadri: Occurrence of 7,4′-Dimethyltectorigenin in the Flowers of Dalbergia sissoo. Current Sci. (India) 34, 431 (1965).
Banerji, A., V.V.S. Murti and T.R. Seshadri: Isolation of Sissotrin. A New Isoflavone Glycoside from the Leaves of Dalbergia sissoo. Indian J. Chem. 4, 70 (1966).
Banerji, A., V.V.S. Murti, T.R. Seshadri and R.S. Thakur: Chemical Components of the Flowers of Dalbergia sissoo. Isolation of 7-Methyltectorigenin, a New Isoflavone. Indian J. Chem. 1, 25 (1963).
Barnes, C.S. and J.L. Occolowitz: The Mass Spectra of Some Naturally Occurring Oxygen Heterocycles and Related Compounds. Austral. J. Chem. 17, 975 (1964).
Barz, W. und H. Grisebach: Über die Bedeutung von 3,5,7,4′-Tetrahydroxyflavanon (Dihydrokaempferol) für die Biosynthese von Isoflavonen. Z. Naturforsch. 21b, 47 (1966).
Barz, W. und H. Grisebach: Über die Umwandlung von Daidzein in die Isoflavonoide der Luzerne. Z. Naturforsch. 21b, 1113 (1966).
Barz, W., L. Patschke and H. Grisebach: The Role of Dihydroflavonols in Flavonoid Biosynthesis. Chem. Commun. 1965, 400.
Batterham, T.J. and R.J. Highet: Nuclear Magnetic Resonance Spectra of Flavonoids. Austral. J. Chem. 17, 428 (1964).
Beck, A.B.: The Oestrogenic Isoflavones of Subterranean Clover. Austral. J. Chem. 15, 223 (1964).
Bentley, R.: private communication to H. Grisebach.
Bevan, C.W.L., A.J. Birch, B. Moore, S.K. Mukerjee: A Partial Synthesis of (±)-Pisatin. Some Remarks on the Structure and Reactions of Pterocarpin. J. Chem. Soc. (London) 1964, 5991.
Bevan, C.W.L., D.E.U. Ekong, M.E. Obasi and J.W. Powell: West African Timbers XIII. Extracts from the Heartwood of Amphimas pterocarpoides and Pterocarpus erinaceus. J. Chem. Soc. (London) C.1966, 509.
Bhrara, S.C., A.C. Jain and T.R. Seshadri: A New Examination of the Special Components of Pterocarpus indicus Heartwood. Current Sci. (India) 33, 303 (1964).
Bhrara, S.C., C. Jain and T.R. Seshadri: Some Reactions of Substituted 2′-Benzyloxychalkone Epoxides. Tetrahedron 20, 1141 (1964).
Bhrara, S.C., A.C. Jain and T.R. Seshadri: Scope of Isoflavone Synthesis Using 2′-Benzyloxychalkone Epoxides. Tetrahedron 21, 963 (1965).
Bhutani, S.P., S.S. Chibber and T.R. Seshadri: Components of the Roots of Pueraria tuberosa: Isolation of a New Isoflavone-C-glycoside (Di-O-acetylpuerarin). Indian J. Chem. 7, 210 (1969).
Bickoff, E.M., A.L. Livingston, S.C. Witt, R.E. Lundin and R.R. Spencer: Isolation of 4′-O-Methylcoumestrol from Alfalfa. J. Agric. Food Chem. 13, 597 (1965).
Bickoff, E.M., R.R. Spencer, B.E. Knuckles and R.E. Lundin: 3′-Methoxycoumestrol from Alfalfa. Isolation and Characterisation. J. Agric. Food Chem. 14, 444 (1966).
Birch, A.J.: Biosynthetic Pathways. In: T. SWAIN, Chemical Plant Taxonomy, p. 141. London: Academic Press. 1963.
Boehler, P. and Ch. Tamm: The Homo-isoflavones, A New Class of Natural Product. Isolation and Structure of Eucomin and Eucomol. Tetrahedron Letters 1967, 3479.
Bouwer, D.C. v.d.M. Brink, J.P. Englebrecht and G.J.H. Rall: Neorautanenia Isoflavonoids Part III. 4-Methoxypterocarpin. A New Pterocarpan from Neorautanenia ficifolia. J.S. African Chem. Inst. 21, 159 (1968).
Bowyer, W.J., J.N. Chatterjea, S.P. Dhoubhadel, B.O. Handford and W.B. Whalley: The Chemistry of the “Insoluble Red Woods”. Part IX Homopterocarpin and Pterocarpin. J. Chem. Soc. (London) 1964, 4212.
Braden, A.W.H., N.K. Hart and J.A. Lamberton: The Oestrogenic Activity and Metabolism of Certain Isoflavones in Sheep. Austral. J. Agric. Research 18, 335 (1967).
Bredenberg, J. B-Son and P.K. Hietala: Investigation of the Structure of Trifolirhzin, an Antifungal Compound from Trifolium pratense L. Acta Chem. Scand. 15, 696 (1961).
Bredenberg, J. B-Son and J.N. Shoolery: A Revised Structure for Pterocarpin. Tetrahedron Letters 1961, 285.
Briggs, L.H. and T. Cebalo: Podocarpaceae X. Synthesis of Podospicatin and its Trimethyl Ether. Tetrahedron 19, 2301 (1963).
Brink, C.v.d.M., J.J. Dekker, E.C. Hanekom, D.H. Meiring and G.J.H. Rall: Neorautanenia Isoflavonoids I. Interconversion of Neodulin and Dehydroneotenone. J.S. African Chem. Inst. 18, 21 (1965).
Büchi, G., L. Crombie, P.J. Godin, J.S. Kaltenbronn, K.S. Siddalingaiah and D.A. Whiting: The Absolute Configuration of Rotenone. J. Chem. Soc. (London) 1961, 2843.
Campbell, N. In: E.H. Rodd, Chemistry of Carbon Compounds, Vol. IVB, p. 921. Amsterdam: Elsevier. 1959.
Cayen, M.N., G. Tang and R.H. Common: Urinary Conversion Products of Biochanin A and Formononetin in the Fowl. Biochim. Biophys. Acta 111, 349 (1965).
Chopin, J., M.-L. Bouillant et P. Lebreton: Sur la méthyl-5 génistéine, nouvelle isoflavone naturelle extraite du Cytise (Cytisus laburnum L.). C.R. hebd. Séances Acad. Sci. 251, 736 (1960).
Claisse, J., L. Crombie and R. Pearce: Structure and Stereochemistry of the Vicianoside Amorphin, the First Rotenoid Glycoside. J. Chem. Soc. (London) 1964, 6023.
Clark-Lewis, J.W.: Configurations of Optically Active Flavonoid Compounds. Rev. Pure Appl. Chem. 12, 96 (1962).
Clark-Lewis, J.W., I. Dainis and G.C. Ramsay: Flavan Derivatives XIV. The Absolute Configurations of Some 1,2-Diarylpropane Derivatives and of Some Isoflavans. Austral. J. Chem. 18, 1035 (1965).
Clark-Lewis, J.W., and R.W. Jemison: The Absolute Configurations of (—)-Angolensin and Some Related 1,2-Diarylpropanes. Austral. J. Chem. 18, 1791 (1965).
Cocker, W., T. Dahl, C. Dempsey and T.B.H. McMurray: Extractives from Woods I. Extractives from Andira inermis. J. Chem. Soc (London) 1962, 4906.
Cocker, W., T.B.H. McMurray and P.A. Staniland: A Synthesis of Demethylhomopterocarpin. J. Chem. Soc. (London) 1965, 1034.
Cooke, R.G. and I.D. Rae: Isoflavonoids. I. Some New Constituents of Pterocarpus indicus Heartwood. Austral. J. Chem. 17, 379 (1964).
Crombie, L.: Chemistry of the Natural Rotenoids. Fortschr. Chem. organ. Naturstoffe 21, 275 (1963).
Crombie, L. and P.J. Godin: Structure and Stereochemistry of the Rotenolones, Rotenolols, Isorotenolones and Isorotenolols. J. Chem. Soc. (London) 1961, 2861.
Crombie, L., C.L. Green and D.A. Whiting: Biosynthesis of Rotenoids. The Origin of C-6 and C-6a. J. Chem. Soc. (London) C.1968, 3029.
Crombie, L. and J.W. Lown: Proton Magnetic Studies of Rotenone and Related Compounds. J. Chem. Soc. (London) 1962, 775.
Crombie, L. and M.B. Thomas: Biosynthesis of Rotenoids. Evidence for 1,2-Aryl Migration and the Isoflavonoid Construction of Rings A, C.and D in Rotenone and Amorphigenin. J. Chem. Soc. (London) C.1967, 1796.
Crombie, L. and D.A. Whiting: The Extractives of Neorautanenia pseudopachyrrhiza. The Isolation and Structure of a New Rotenoid and Two New Isoflavanones. J. Chem. Soc. (London) 1963, 1569.
Dean, F.M.: Naturally Occurring Oxygen Ring Compounds. London: Butterworth. 1963.
Dean, F.M. and V. Podimuang: The Course of the Algar-Flynn-Oyamada (A.F. O.) Reaction. J. Chem. Soc. (London) 1965, 3978.
Deschamps-Vallet, C. et C. Mentzer: Sur une nouvelle voie d’accès à la série du «coumestane». C.R. hebd. Seances Acad. Sci. 251, 736 (1960).
Dewick, P.M., W. Barz and H. Grisebach: A Possible Chemical Analogy for Coumestan Biosynthesis. Chem. Commun. 1969, 466.
Dewick, P.M., W. Barz and H. Grisebach: Biosynthesis of Coumestrol in Phaseolus Auveus Roxb. Phytochem. 9, 775 (1970).
Djerassi, C., W.D. Ollis and R.C. Russell: The Relative Stereochemistry of the Rotenoids. J. Chem. Soc. (London) 1961, 1448.
Dutta, N.L.: Chemical Investigations of Mundulea suberose II. Constitution of Munetone, the Principal Crystalline Product of the Root Bark. J. Indian Chem. Soc. 36, 165 (1959).
Dyke, S.F., W.D. Ollis and M. Sainsbury: Synthesis of Isoflavones III. Caviunin. J. Org. Chem. (USA) 26, 2453 (1961).
Dyke, S.F., W.D. Ollis and M. Sainsbury: The Constitution of Munetone. Proc. Chem. Soc. (London) 1963, 179.
Dyke, S.F., W.D. Ollis and M. Sainsbury: Synthetis of Isoflavones IV. Munetone J. Chem. Soc. (London) C.1966, 749.
Dyke, S.F., W.D. Ollis, M. Sainsbury and J.S.P. Schwarz: The Extractives of Piscidia erythrina L — II. Synthetical Evidence Concerning the Structure of Ichthynone. Tetrahedron 20, 1331 (1964).
Eade, R.A., H. Hinterberger and J.J.H. Simes: Extractives of Australian Timbers III Afromosin (Castanin, 6,4′-Dimethoxy-7-hydroxyisoflavone) from Castanospermum australe. Austral. J. Chem. 16, 188 (1963).
East, A.J., W.D. Ollis and R.E. Wheeler: Natural Occurrence of 3-Aryl-4-hydroxycoumarins. Part 1. Phytochemical Examination of Derris robusta (Roxb.) Benth. J. Chem. Soc. (London), C.1969, 365.
Emerson, O.H. and E.M. Bickoff: Synthesis of Coumestrol, 3,9-Dihydroxy-6H-benzofuro[3,2-c][1]benzopyran-6-one. J. Amer. Chem. Soc. 80, 4381 (1958).
Erdtman, H. and T. Norin: Heartwood Constituents of Laburnum alpinum Bercht. and Presl. Acta Chem. Scand. 17, 1781 (1963).
Falshaw, C.P., R.A. Harmer, W.D. Ollis, R.E. Wheeler, V.R. Lalitha and N.V. Subba Rao: Natural Occurrence of 3-Aryl-4-hydroxycoumarins. Part II. Phytochemical Examination of Derris scandens (Roxb.) Benth. J. Chem. Soc. (London) C.1969, 374.
Falshaw, C.P., W.D. Ollis, J.A. Moore and K. Magnus: The Extractives of Piscidia erythrina L — III. The Constitutions of Lisetin, Piscidone and Piscerythrone. Tetrahedron, Supplement No. 7, 333 (1966).
Farkas, L.: Natural Isoflavones and their Glycosides. In: T.S. Gore, B.S. Joshi, S.V. Sunthanker and B.D. Tilak, Recent Progress in the Chemistry of Natural and Synthetic Colouring Matters and Related Fields, p. 279. London: Academic Press. 1962.
Farkas, L. and M. Nogradi: The Structure of Sophorabiose. Tetrahedron Letters 1964, 3919.
Farkas, L., J. Varady und A. Gottsegen: Untersuchung der Glykoside der Baptisia tinctoria R. Br., II. Synthèse des 7,3′,4′,5′-Tetrahydroxyisoflavons (Baptigenin). Chem. Ber. 96, 1865 (1963).
Fukui, K. and T. Matsumoto: Synthetic Studies of Sesamol Derivatives VI. The Synthesis of 6,7,3′,4′-bis(methylenedioxy)isoflavone. An Isomer of the Maxima Substance A, and Related Compounds. Bull. Chem. Soc. Japan 38, 612 (1965).
Fukui, K. and T. Matsumoto: The Synthesis of Trisolone. Bull. Chem. Soc Japan 38, 887 (1965).
Fukui, K. and M. Nakatama: Total Synthesis of (±)-Pterocarpin and (±)-Pisatin. Tetrahedron Letters 1966, 1805.
Fukui, K. and M. Nakayama: Total Synthesis of Nepseudin. Bull. Chem. Soc. Japan 41, 1385 (1968).
Fukui, K., M. Nakayama and M. Hatanaka: Synthesis of Maxima Substance B. Bull. Chem. Soc. Japan 35, 1929 (1962).
Fukui, K., M. Nakayama and M. Hatanaka: Synthesis of Cabreuvin. Nippon Kagaku Zasshi 84, 189 (1963). [Chem. Abstr. 59, 13926 (1963)].
Fukui, K., M. Nakayama, H. Tsuge and K. Tsuzuki: The Synthesis of (±)-Maackiain. Experientia 24, 536 (1968).
Fukui, K., M. Nakayama and K. Tsuzuki: The Synthesis of (±)-4-Methoxypterocarpin. Experientia 25, 122 (1969).
Geissman, T.A. and E. Hinreiner: Theories of the Biogenesis of Flavonoid Compounds. I and II. Botan. Rev. 18, 77, 165 (1952).
Geoghegan, M., W.I. O’Sullivan and E.M. Philbin: Flavonoid Epoxides II. A New Synthesis of 4-Hydroxy-3-phenylcoumarins. Tetrahedron 22, 3209 (1966).
Ghanim, A., A. Zaman and A.R. Kidwai: Synthesis of 7-Methyltectorigenin. Tetrahedron Letters 1964, 185.
Gilbert, A H., A. Mcgookin and A. Robertson: Isoshekkangenin and the Synthesis of 4-hydroxycoumarins. J. Chem. Soc. 1957, 3740.
Gopinath, K.W., A.R. Kidwai and L. Prakash: The Chemical Examination of Iris Nepalensis — I Structure of Irisolone. Tetrahedron 16, 201 (1961).
Gottlieb, O.R.: Private Communication.
Govindachari, T.R., K. Nagarajan, B.R. Pai and P.C. Parthasarthy: Chemical Investigations of Wedelia calendulacea. II. The Position of the Methoxyl group in Wedelolactone. J. Chem. Soc. (London) 1957, 545.
Grisebach, H.: The Biosynthesis of Isoflavones. In: W.D. Ollis, Chemistry of Natural Phenolic Compounds, p. 59. Oxford: Pergamon Press. 1961.
Grisebach, H.: Biosynthesis of Flavonoids. In: T.W. Goodwin, Chemistry and Biochemistry of Plant Pigments, p. 279. London: Academic Press. 1965.
Grisebach, H.: Recent Investigations on the Biosynthesis of Flavonoids. In: T.J. Mabry, R.E. Alston and V.C. Runeckles, Recent Advances in Phytochemistry, Vol. I., p. 379. New York: Appleton-Century-Crofts. 1968.
Grisebach, H. und W. Barz: Zur Biogenese der Isoflavone VIII. Mitt.: 4,2′,4′-Trihydroxy-chalkon-4′-glucosid als Vorstufe fur Coumoestrol, Formononetin und Daidzein in der Luzerne (Medicago sativa L.). Z. Naturforsch. 19b, 569 (1964).
Grisebach, H. und G. Brandner: Über die Biogenese von Biochanin A und Formononetin in der Kichererbse. Z. Naturforsch. 16b, 2 (1961).
Grisebach, H. und G. Brandner: Einbau des 2′,4,4′,6′-Tetrahydroxychalkon-2′-glucosid-[β-14C] in Isoflavone. Experientia 18, 400 (1962).
Grisebach, H. and W.D. Ollis: Biogenetic Relationships between Coumarins, Flavonoids, Isoflavonoids, and Rotenoids. Experientia 11, 4 (1961).
Grisebach, H. und H. Zilg: Über die Bedeutung der Isoflavanone bei der Isoflavonbiosynthese. Z. Naturforsch. 23b, 494 (1968).
Grover, S.K., A.C. Jain and T.R. Seshadri: A Convenient Synthesis of Isoflavones and Di-O-Methylangolensin Using Aryl Migration. Indian J. Chem. 1, 517 (1963).
György, P., K. Murata and H. Ikehata: Antioxidants Isolated from fermented Soybeans (Tempeh). Nature 203, 870 (1964).
Haller, H.L., L.D. Goodhue and H.A. Jones: The Constituents of Derris and Other Rotenone-bearing Plants. Chem. Rev. 30, 33 (1942).
Harborne, J.B.: Phenolic Glycosides and their Natural Distribution. In: J.B. Harborne, Biochemistry of Phenolic Compounds, p. 129. London: Academic Press. 1964.
Harborne, J.B.: Comparative Biochemistry of the Flavonoids. London: Academic Press. 1967.
Harborne, J.B., O.R. Gottlieb and M. Magalhaes: Occurrence of the Isoflavone Afromosin in Cabreuva Wood. J. Org. Chem. (USA) 28, 881 (1963).
Harper, S.H.: The Active Principles of Leguminous Fish-Poison Plants. Part V. Derris malaccensis and Tephrosia toxicaria. J. Chem. Soc. (London) 1940, 1178.
Harper, S.H., A.D. Kemp and W.G.E. Underwood: Heartwood Constituents of Swartzia madagascariensis. Chem. and Ind. 1965, 562.
Harper, S.H., A.D. Kemp and W.G.E. Underwood: Heartwood Constituents of Swartzia madagascariensis. Chem. Commun. 1965, 309.
Harper, S.H., A.D. Kemp, W.G.E. Underwood and R.V.M. Campbell: Pterocarpanoid Constituents of the Heartwoods of Pericopsis angolensis and Swartzia madagascariensis. J. Chem. Soc. (London) C.1969, 1109.
Harper, S.H. and W.G.E. Underwood: The Active Principles of Leguminous Fish Poison Plants. Part X. Toxicarol Isoflavone. J. Chem. Soc. (London) 1965, 4203.
Highet, R.J. and P.F. Highet: The Structure of Two Isoflavones from the Abyssinian Berebera Tree. J. Org. Chem. (USA) 32, 1055 (1967).
Hillis, W.E. and N. Ishikura: An Enzyme from Eucalyptus which Converts Cinnamoyl Triacetic Acid into Pinosylvin. Phytochem. 8, 1079 (1969).
Hudson, A.T. and R. Bentley: The Isolation of Isoflavonoids from Bacteria. Chem. Commun. 1969, 830.
Imamura, H., Y. Tanno, T. Takahashi: Isolation and Identification of Four Isoflavone Derivatives from Eurasian teak Pericopsis: Mikuzai Gakkaishi 14, 295 (1968) [Chem. Abstr. 70, 44835 (1969)].
Itahaki, Y., T. Kurokawa, S. Sasaki, C.T. Chang and F.C. Chen: The Mass Spectra of Chalcones, Flavones and Isoflavones. Bull. Chem. Soc. Japan 39, 538 (1966).
Ito, S., Y. Fujise and A. Mori: Absolute Configuration of Pterocarpinoids. Chem. Commun. 1965, 595.
Jackman, L.M.: Some Applications of Nuclear Magnetic Resonance Spectroscopy in Natural Product Chemistry. Fortsch. Chem. org. Naturstoffe 23, 315 (1965).
Jain, A.C., P. Lal and T.R. Seshadri: Synthesis of (±)-Ougenin. Indian J. Chem. 7, 61 (1969).
Jain, A.C., V.K. Rohatgi and T.R. Seshadri: A Novel Synthesis of 3-Phenyl-4-hydroxycoumarins. Tetrahedron 23, 2499 (1967).
Jain, A.C., P.D. Sarpal and T.R. Seshadri: Synthesis of Afromosin Using the Chalcone Epoxide Method. Indian J. Chem. 3, 369 (1965).
Johnson, A.P. and A. Pelter: The Structure of Robustic Acid, A New 4-Hydroxy-3-phenylcoumarin. J. Chem. Soc. (London) 1966, 606.
Johnson, A.P., A. Pelter and P. Stainton: Extractives from Derris scandens. Part I. The Structures of Scandenin and Lonchocarpic Acid. J. Chem. Soc. (London) 1966, 192.
Jurd, L.: Anthocyanins and Related Compounds IV. The Synthesis of Coumestrol and related Coumarinobenzofurans from Flavylium Salts. J. Org. Chem. (USA) 29, 3036 (1964).
Jurd, L.: Synthesis of 7-Hydroxy-5′,6′-methylenedioxybenzofurano(3′,2′: 3,4)-coumarin (Medicagol). J. Pharm. Sci. 54, 1221 (1965).
Kalra, V.K., Kukla and T.R. Seshadri: Synthesis of Lucernol and Sativol Dimethyl Ether. Tetrahedron Letters 1967, 2153.
Kalra, V.K., A.S. Kukla and T.R. Seshadri: Synthesis of (±)-7,8,4′-Trimethoxypterocarpan and (′)-7-Hydroxy-8,4′-Dimethoxypterocarpan. Tetrahedron 23, 3221 (1967).
Kondratenko, E.S., A.U. Kasymov and N.K. Abubakirov: The Structure of Amorphygenine. Khim. Prir. Soedin 3, 307 (1967). [Chem. Abstr. 68, 21865 (1968)].
Kukla, A.S. and T.R. Seshadri: Synthesis of Maxima Substance B. J. Sci. Ind. Res. (India) 21B, 97 (1962).
Kukla, A.S. and T.R. Seshadri: Constitution and Synthesis of Maxima Isoflavones — A and — B. Tetrahedron 18, 1443 (1962).
Kurosawa, K., W.D. Ollis, B.T. Redman, I.O. Sutherland, O.R. Gottlieb and H.M. Alves: The Absolute Configurations of the Animal Metabolite. Equol, Three Narurally Occurring Isoflavans, and One Natural Isoflavanquinone. Chem. Commun. 1968, 1265.
Kurosawa, K., W.D. Ollis, B.T. Redman, I.O. Sutherland, A.B. de Oliveira, O.R. Gottlieb and H.M. Alves: The Natural Occurrence of Isoflavans and an Isoflavanquinone. Chem. Commun. 1968, 1263.
Lebreton, P., K.R. Markham, W.T. Swift, Oung-Boran and T.J. Mabry: Flavonoids of Baptisia australis (Leguminosae). Phytochem. 6, 1675 (1967).
Livingston, A.L., E.M. Bickoff, R.E. Lundin and L. Jurd: Trifoliol, a New Coumestan from Ladino Clover. Tetrahedron 20, 1963 (1964).
Livingston, A.L., S.C. Witt, R.E. Lundin and E.M. Bickoff: Medicagol, a New Coumestan from Alfalfa. J. Org. Chem. (USA) 30, 2353 (1965).
Mabry, T.J., J. Kagan and H. Roesler: Nuclear Magnetic Resonance Analysis of Flavonoids. The University of Texas Publication No 6418. Austin. 1964.
Mabry, T.J., J. Kagan and H. Roesler: N.M.R. Spectra of the Trimethylsilyl Ethers of Flavonoid Glycosides. Phytochem. 4, 177 (1965).
Malhotra, A., V.V.S. Murti and T.R. Seshadri: Lanceolarin, A New Isoflavone Glycoside of Dalbergia Lanceolaria. Tetrahedron 23, 405 (1967).
Malleswar, D., G. Srimannarayana, V. Sundaramurty and N.V. Subba Rao: Synthesis of 7-Hydroxy-11,12-dimethoxycoumestan. A Component of Alfalfa. Current Sci. (India) 36, 346 (1967).
Markham, K.R. and T.J. Mabry: The Identification of Twenty-three 5-Deoxyand Ten 5-Hydroxyflavonoids from Baptisia lecontei (Leguminosae): Phytochem. 7, 791 (1968).
Markham, K.R., T.J. Mabry and T.W. Swift: New Isoflavones from the Genus Baptisia (Leguminosae). Phytochem. 7, 803 (1968).
Markham, K.R., W. Rahman, S. Jehan and T.J. Mabry: NMR Analysis and Synthesis of 6-and 8-C-Methylisoflavones. J. Heterocyclic Chem. 4, 61 (1967).
Markham, K.R., W.T. Swift and T.J. Mabry: A New Isoflavone Glycoside from Baptisia australis. J. Org. Chem. (USA) 33, 462 (1968).
Morgan, J.W.W. and R.J. Orsler: Isolation of 7-Methyltectorigenin from the Heartwood of Muninga (Pterocarpus angolensis). Chem. and Ind. 1967, 1173.
Moustafa, E. and E. Wong: Purification and Properties of Chalcone-Flavanone Isomerase from Soya Bean Seed. Phytochem. 6, 625 (1967).
Murakami, T., Y. Nishikawa and T. Ando: Constituents of Japanese and Chinese Crude Drugs IV. Constituents of Pueraria root. Chem. Pharm. Bull. (Tokyo) 8, 688 (1960).
Oliveira, A.B., O.R. Gottlieb and W.D. Ollis: Chemsitry of Brazilian Leguminosae XVII — Constituents of Machaerium villosum. An Acad. Brasil. Cienc. 40, 147 (1968). [Chem. Abstr. 70, 44797 (1969)].
Ollis, W.D.: The Isoflavonoids. In: T.A. Geissman, The Chemistry of Flavonoid Compounds, p. 353. Oxford: Pergamon Press. 1962.
Ollis, W.D.: Structural Relationships Involving the Rotenoids. In: H.R. Arthur, Symposium on Phytochemistry, Hong Kong 1961, p. 128. Hong Kong University Press. 1964.
Ollis, W.D.: The Neoflavanoids, a New Class of Natural Products. Experientia 22, 777 (1966).
Ollis, W.D.: New Structural Variants Among the Isoflavonoid and Neoflavonoid Classes. In: T.J. Mabry, R.E. Alston and V.C. Runeckles, Recent Advances in Phytochemistry,Vol. I, p. 329. New York: Appleton-Century-Crofts. 1968.
Ollis, W.D., K.L. Ormand and I.O. Sutherland: The Oxidative Rearrangement of Chalcones by Thallic Acetate. A Chemical Analogy for Isoflavone Biosynthesis. Chem. Commun. 1968, 1237.
Ollis, W.D., M.V.J. Ramsay and I.O. Sutherland: The Absolute Configuration of (—)-Angolensein. Austral. J. Chem. 18, 1787 (1965).
Ollis, W.D., C.A. Rhodes and I.O. Sutherland: Extractives of Millettia dura (DUNN). Constitutions of Durlettone, Durmillone, Milldurone, Millettone and Millettosin. Tetrahedron 23, 4741 (1967).
Ollis, W.D. and I.O. Sutherland: Isoprenoid units in Natural Phenolic Compounds. In: W.D. Ollis, Recent Developments in the Chemistry of Natural Phenolic Compounds, p. 74. Oxford: Pergamon Press. 1961.
Orth, H. and P. Forschner: Formononetin and Extraneous Substances in Pterocarpus vidalianus. Holzforschung 19, 111 (1965). [Chem. Abst. 64, 2325 (1966).]
Pachler, K.G.R. and W.G.E. Underwood: A Proton Magnetic Resonance Study of Some Pterocarpan Derivatives. The Conformation of the 6a,11 a-Dihydro-6H-benzofuro[3,2-c]-[1]benzopyran Ring System. Tetrahedron 23, 1817 (1967).
Paris, R.-R. et G. Faugeras: Sur les flavonoides des fleurs du Retama raetam Webb, et Berth. Isolement d’une isoflavone identifiée au génistoside. C.R. hebd. Séances Acad. Sci. 257, 1728 (1963).
Paris, R.-R. et G. Faugeras: Sur les isoflavones des Papilionacées-Génistées. Isolement du genistoside à partir de l’Ulex nanus Forst. et de l’Adenocarpus complicatus Gay et du méthyl-génisteol à partir du Genista hispanica L.C.R. hebd. Séances Acad. Sci. 261, 1761 (1965).
Parthasarathy, M.R., R.N. Puri and T.R. Seshadri: New Components of Pterocarpus dalbergioides Heartwood. Indian J. Chem. 7, 118 (1969).
Patschke, L., W. Barz und H. Grisebach: Über den Einbau von 5,7,4′-Trihydroxyflavanon-[2,6,8,1014-C4] in Cyanidin und die Isoflavone Biochanin-A und Formononetin. Z. Naturforsch. 19b, 1110 (1964).
Patschke, L., W. Barz und H. Grisebach: Stereospezifischer Einbau von (—)5,7,4′-Trihydroxyflavanon in Flavonoide und Isoflavone. Z. Naturforsch. 21b, 201 (1966).
Pelter, A. and P.I. Amenechi: Isoflavonoid and Pterocarpinoid Extractives of Lonchocarpus laxiflorus. J. Chem. Soc. (London) C.1969, 887.
Pelter, A. and P. Stainton: Extractives from Derris scandens II. Isolation of Osajin and Two Isoflavones, Scandenone and Scandinone. J. Chem. Soc. (London) C.1966, 701.
Pelter, A., P. Stainton and M. Barber: The Mass Spectra of Oxygen Heterocycles II. The Mass Spectra of Some Flavonoids. J. Heterocyclic Chem. 2, 262 (1965).
Pelter, A., P. Stainton, A.P. Johnson and M. Barber: The Mass Spectra of Oxygen Heterocycles I. The 4-Hydroxy-3-phenylcoumarins (Isoflavonols) J. Heterocyclic Chem. 2, 271 (1965).
Perrin, D.R.: The Structure of Phaseollin. Tetrahedron Letters 1964, 29.
Perrin, D.R. and W. Bottomley: Studies on Phytoalexins. V. The structure of Pisatin from Pisum sativum L. J. Amer. Chem. Soc. 84, 1919 (1962).
Perrin, D.R., and I.A.M. Cruickshank: The Antifungal Activity of Pterocarpans towards Monilinia fructicola. Phytochem. 8, 971 (1969).
Prakash, L., A. Zaman and A.R. Kidwai: The Chemical Examination of Iris nepalensis III. Isolation and Structure of Irisolidone. J. Org. Chem. (USA) 30, 3561 (1965).
Rangaswami, S. and B.V.R. Sastry: Constitution of Maxima Substance A. Proc. Indian Acad. Sci. 44A, 279 (1956).
Reed, R.I. and J.M. Wilson: Electron Impact and Molecular Dissociation. Part XII. The Cracking Patters of Some Rotenoids and Flavones. J. Chem. Soc. (London) 1963, 5949.
Robinson, R.: The Structural Relations of Natural Products. Oxford: Clarendon Press. 1955.
Roesler, H., T.J. Mabry, M.F. Cranmer and J. Kagan: The Nuclear Magnetic Resonance Analysis of the Disaccharide in Flavonoid Rhamoglucosides. J. Org. Chem. (USA) 30, 4346 (1965).
Roesler, H., T.J. Mabry und J. Kagan: Sphaerobiosid, ein Isoflavonglykosid aus Baptisia sphaerocarpa Chem. Ber. 98, 2193 (1965).
Saitoh, T. and S. Shibata: Chemical Studies on the Oriental Plant Drugs XXII. Some New Constituents of Licorice Root. 2. Glycyrol, 5-O-Methylglycyrol and Isoglycyrol. Chem. Pharm. Bull. (Tokyo) 17, 729 (1969).
Schultz, G.: Isoflavonglucoside Formononetin-7-glucosid und Biochanin A-7-glucosid in Trifolium pratense L. Naturwiss. 52, 517 (1965).
Schwarz, J.S.P., A.I. Cohen, W.D. Ollis, E.A. Kalzka and L.M. Jackman: The Extractives of Piscidia erythrina I. The Constitution of Ichthynone. Tetrahedron 20, 1317 (1964).
Seshadri, T.R.: Advances in the Phytochemistry of Isoflavonoids. In: H.R. ARTHUR, Symposium on Phytochemistry, Hong Kong 1961, p. 145. Hong Kong University Press. 1964.
Shabbir, M., A. Zaman, L. Crombie, B. Tuck and D.A. Whiting: Structure of Auriculatin. Extractive of Millettia auriculata. J. Chem. Soc. (London) C.1968, 1899.
Shibata, S., T. Murata and M. Fujita: Studies on the Constituents of Japanese and Chinese Crude Drugs. X. Wistin, A New Isoflavone Glucoside of Wistaria spp. Chem. Pharm. Bull. (Tokyo) 11, 382 (1963).
Shibata, S. and Y. Hishikawa: Studies on the Constituents of Japanese and Chinese Crude Drugs VII. On the Constituents of the Roots of Sophora subprostrata Chun et T. Chen and Sophora japonica L. Chem. Pharm. Bull. (Tokyo) 11, 167 (1963).
Shibata, S. and T. Saitoh: The Chemical Studies on the Oriental Plant Drugs XIX. Some New Constituents of Licorice Root. The Structure of Licoricidin. Chem. Pharm. Bull. (Tokyo) 16, 1932 (1968).
Shutt, D.A. and A.W.H. Braden: The Significance of Equol in Relation to the Oestrogenic Responses in Sheep Ingesting Clover with a High Formononetin Content. Austral. J. Agric. Res. 19, 545 (1968).
Simonitsch, E., H. Frei und H. Schmid: Die Konstitution des Pachyrrhizins. Monatsh. Chem. 88, 541 (1957).
Spencer, R.R., E.M. Bickoff, R.E. Lundin and B.E. Knuckles: Lucernol and Sativol, Two New Coumestans from Alfalfa (Medicago sativa). J. Agric. Food Chem. 14, 162 (1966).
Spencer, R.R., B.E. Knuckles and E.M. Bickoff: 7-Hydroxy-11,12-dimethoxycoumestan. Characterisation and Synthesis. J. Org. Chem. (USA) 31, 988 (1966).
Suginome, H.: Oxygen Heterocycles. A New Isoflavanone from Sophora japonica L. J. Org. Chem. (USA) 24, 1655 (1959).
Suginome, H.: Maackiain. Bull. Chem. Soc. Japan 39, 1529 (1966).
Suginome, H.: The Absolute and Relative Stereochemical Correlation of Isoflavanone Sophorol and Naturally-occurring Isoflavan Derivatives. Bull. Chem. Soc. Japan 39, 1544 (1966).
Suginome, H. and T. Iwadare: Sauerstoff-Heteroringe. Die Konfiguration und Synthèse des d,l-Homopterocarpins. Experientia 18, 163 (1962).
Suginome, H. and T. Kio: The Co-occurrence of Isoflavonoids at Different Oxidation Levels. Bull. Chem. Soc. Japan 39, 1541 (1966).
Tamura, S., C.F. Chang, A. Suzuki and S. Kumai: Chemical Studies on “Clover Sickness” Parti. Isolation and Structural Elucidation of Two New Isoflavonoids in Red Clover. Agr. Biol. Chem. 33, 391 (1969).
Uchiyama, M. and M. Matsui: A New Approach to the Synthesis of Isoflavones, 2′-Hydroxyisoflavones and an Alternative Synthesis of (±)-pterocarpin. Agric. Biol. Chem. 31, 1490 (1967).
Varady, J.: A New Method for the Ring Isomerisation of Isoflavones. Direct Synthesis of Tectorigenin, 4-Methyltectoringenin, Caviunin and Other Isoflavones. Tetrahedron Letters 1965, 4273.
Vaughan, P.F. T., V.S. Butt, H. Grisebach and L. Schill: Hydroxylation of Flavonoids by a Phenolase Preparation from Leaves of Spinach Beet. Phytochem. 8, 1373 (1969).
Venkataraman, K.: Flavones and Isoflavones. Fortschr. Chem. organ. Naturstoffe 17, 1 (1959).
Verbit, L. and J.W. Clark-Lewis: Optically Active Aromatic Chromophores — VIII. Studies in the Isoflavonoid and Rotenoid Series. Tetrahedron. 24, 5519 (1968).
Waiss, A.C. and J. Corse: Photooxidative Cyclization of Quercetin Pentamethyl Ether. J. Amer. Chem. Soc. 87, 2068 (1965).
Wanzlick, H.W., R. Gritzky und H. Heiderpriem: Die Synthèse des Wedelolactons. Chem. Ber. 96, 305 (1963).
Warburton, W.K.: The Isoflavones. Quart. Rev. (Chem. Soc. London) 8, 67 (1954).
Weinges, K.: The Neighbouring Group Effect in the Conversion of Tetramethyl-(±)-catechin into 2-Chlorotetramethyl-(—)-isocatechin. Proc. Chem. Soc. (London) 1964, 138.
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 to Structure Elucidation. Tetrahedron 24, 1407 (1968).
Wong, E.: Pratensein. 5,7,3′-Trihydroxy-4′-methoxyisoflavone. J. Org. Chem. (USA) 28, 2336 (1963).
Wong, E.: Flavonoid Biosynthesis in Cicer arietinum. Biochim. Biophys. Acta 111, 358 (1965).
Wong, E.: The Role of Chalcones and Flavanones in Flavonoid Biosynthesis. Phytochem. 7, 1751 (1968).
Wong, E. and C.M. Francis: Flavonoids in Genotypes of Trifolium subterraneum — II. Mutants of the Geraldton Variety. Phytochem. 7, 2131 (1968).
Wong, E. and H. Grisebach: Further Studies on the Role of Chalcone and Flavanone in Biosynthesis of Flavonoids. Phytochem. 8, 1419 (1969).
Wong, E., P.I. Mortimer and T.A. Geissman: Flavonoid Constituents of Cicer arietinum. Phytochem. 4, 89 (1965).
Wong, E. and E. Moustafa: Flavanone Biosynthesis. Tetrahedron Letters 1966, 3021.
Zilg, H. and H. Grisebach: Biosynthesis of Isoflavones — XVII. Identification and Biosynthesis of Coumestanes in Soja hispida. Phytochem. 7, 1765 (1968).
Author information
Authors and Affiliations
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1970 Springer-Verlag/Wien
About this chapter
Cite this chapter
Wong, E. (1970). Structural and Biogenetic Relationships of Isoflavonoids. In: Herz, W., Grisebach, H., Scott, A.I. (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 28. Springer, Vienna. https://doi.org/10.1007/978-3-7091-7123-3_1
Download citation
DOI: https://doi.org/10.1007/978-3-7091-7123-3_1
Publisher Name: Springer, Vienna
Print ISBN: 978-3-7091-7125-7
Online ISBN: 978-3-7091-7123-3
eBook Packages: Springer Book Archive