Abstract
Isoflavonoids differ from other flavonoid compounds in having as a basic structural feature the branched C6C3C6 skeleton shown in (1). Within this group are included many classes of natural products. Isoflavones, isoflavanones, rotenoids, pterocarpans and coumestans are well established members of this group (Ollis, 1962), while others such as isoflavans, 3-aryl-4-hydroxycoumarins, coumaronochromones, and hydroxy- and dehydro-variants of pterocarpans and rotenoids have only recently been reported as natural products. The skeletal structures of the various classes of isoflavonoid, arranged in order of their oxidation level, are given in Fig. 14.1. The structural variety displayed in the isoflavonoids is, in fact, greater than existing in the normal flavonoid series.
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References
Adams, D. L., Crombie, L. and Whiting, D. A. (1966), J. chem. Soc. (C) 542.
Adinarayana, D., Radhakrishniah, M., Rao, J. R., Campbell, R. and Crombie, L. (1971), J. chem. Soc. (C) 29.
Adinarayana, D. and Rao, J. R. (1972a), Tetrahedron 28, 5377.
Adinarayana, D. and Rao, J. R. (1972b), 8th Internatl. Symposium on the Chemistry of Natural Products (1UPAC) Abstracts, p. 96.
Adityachaudhury, N. and Gupta, P. K. (1973), Phyto chemistry 12, 425.
Ahluwalia, V. K., Sachdev, G. P. and Seshadri, T. R. (1965), Indian J. Chem.3, 474.
Akisanya, A., Bevan, C. E. L. and Hirst, J. (1959), J. chem. Soc. 2679.
Alencar, R. D., Braz Filho, R. and Gottlieb, O. R. (1972), Phytochemistry 11, 1517.
Almeida, M. E. L. and Gottlieb, O. R. (1974), Phytochemistry 13, 751.
Assumpcao, R. M. V. and Gottlieb, O. R. (1973), Phytochemistry 12, 1184.
Balakrishna, S., Ramanathan, J. D., Seshadri, T. R. and Venkataramani, B. (1962), Proa Roy. Soc. (1ondon) A268, 1.
Banerji, A., Murti, V. V. S. and Seshadri, T. R. (1965), Curr. Sci.34, 431.
Banerji, A., Murti, V. V. S. and Seshadri, T. R. (1966), Indian J. Chem.4, 70.
Banerji, A., Murti, V. V. S., Seshadri, T. R. and Thakur, R. S. (1963) Indian J. Chem.1, 25.
Batterham, T. J., Shutt, D. A., Hart, N. K., Braden, A. W. H. and Tweeddale, H. J. (1971), AustJ. agric. Res.22, 131.
Beck, A. B. (1964), Aust. J. Chem.15, 223.
Beck, A. B. and Knox, J. R. (1971), Aust. J. Chem.24, 1509.
Bevan, C. W. L., Birch, A. J., Moore, B. and Mukerjee, S. K. (1964), J. chem. Soc. 5991.
Bevan, C. W. L., Ekong, D. E. U., Obasi, M. E. and Powell, J. W. (1966), J. chem. Soc. (C) 509.
Bhargava, K. K., Krishnaswamy, N. R. and Seshadri, T. R. (1972), Indian J. Chem.10, 810.
Bhutani, S. P., Chibber, S. S. and Seshadri, T. R. (1969), Indian J. Chem.7, 210.
Bickoff, E. M. (1968), Rev. Ser. 1/1968, Commonwealth Bur. of Pastures and Field Crops, pp. 1–39. Hurley, Berkshire, England.
Bickoff, E. M., Livingston, A. L., Witts, S. C., Lundin, R. E. and Spencer, R. R. (1965), J. agric. Fd. Chem 13, 597.
Bickoff, E. M., Loper, G. M., Hanson, C. H., Graham, J. H., Witts, S. C. and Spencer, R. R. (1967), Crop Sci.7, 259.
Bickoff, E. M., Spencer, R. R., Knuckles, B. E. and Lundin, R. E. (1966), J. agric. Fd. Chem. 14, 444.
Bickoff, E. M., Spencer, R. R., Witt, S. C. and Knuckles, B. E. (1969), ‘Studies on the Chemical and Biological Properties of Coumestrol and Related Compounds’. Tech. Bull. No. 1408, U.S.D.A.
Biggers, J. D. (1959), In The Pharmacology of Plant Phenolics (J. W. Fairbairn, ed.), pp. 51–69. Academic Press, London.
Bouwer, D., Brink, C. v. d. M., Engelbrecht, J. P. and Rail, G. J. H. (1968), J. S. African chem. Inst.21, 159.
Bowyer, W. J., Chatterjea, J. N., Dhoubhadel, S. P., Handford, B. O. and Whalley, W. B. (1964), J. chem. Soc. 4212.
Braden, A. H., Hart, N. K. and Lamberton, J. A. (1967), Aust. J. agric. Res.18, 335.
Braden, A. H. and McDonald, I. W. (1970). In Australian Grasslands (R. M. Moore, ed.), pp. 38–392. Australian National University Press, Canberra.
Braz Filho, R., Almeida, M. E. L. and Gottlieb, O. R. (1973b), Phytochemistry 12, 1187.
Braz Filho, R. and Gottlieb, O. R. (1971), Phytochemistry 10, 2433.
Braz Filho, R., Gottlieb, O. R. and Assumpcao, R. M. V. (1971), Phytochemistry 10, 2835.
Braz Filho, R., Gottlieb, O. R., Pinho, S. L. V., Monte, F. J. Q. and Rocha, A. I. D. (1973a), Phytochemistry 12, 1184.
Bredenberg, J. B-Son. and Hietala, P. K. (1961), Acta, chem. scand.15, 696.
Brink, C. v. d. M., Dekker, J. J., Hanekom, E. C., Meiring, D. H. and Rail, G. J. H. (1965), J. S. African chem Inst.18, 21.
Brink, C. v. d. M., Nel, W., Rail, G. J. H., Weitz, J. C., Pachler, K. G. R. (1966), J. S. African chem. Inst.19, 24.
Brink, C. v. d. M., Engelbrecht, J. P. and Graham, D. Z. (1970), J. S. African chem. Inst.23, 24.
Buchi, G., Crombie, L., Godin, P. J., Kaltenbronn, J. S., Siddalingaiah, K. S. and Whiting, D. A. (1961), J. chem. Soc. 2843.
Burden, R. S., Bailey, J. A. and Dawson, G. W. (1972), Tetrahedron Letters 4175.
Campbell, R. V. M., Harper, S. H. and Kemp, A. D. (1969), J. chem. Soc. (C) 1787.
Claisse, J., Crombie, L. and Pearce, R. (1964), J. chem. Soc. 6023.
Clark-Lewis, J. W. (1962), Rev. pure appl Chem.12, 96.
Cocker, W., Dahl, T., Dempsey, C. and McMurray, T. B. H. (1962), J. chem. Soc. 4906.
Cocker, W., McMurray, T. B. H. and Staniland, P. A. (1965), J. chem. Soc. 1034.
Craveiro, A. A. and Gottlieb, O. R. (1974), Phytochemistry 13, 1629.
Crombie, L. (1963), Fortschr. Chem. organ. Naturst.21, 275.
Crombie, L. and Godin, P. J. (1961), J. chem. Soc. 2861.
Crombie, L. and Lown, J. W. (1962), J. chem. Soc. 775.
Crombie, L. and Whiting, D. A. (1963), J. chem. Soc. 1569.
Cruickshank, I. A. M. and Perrin, D. R. (1971), J. Indian bot. Soc. Golden Jubilee, Vol 50A, 1.
Dean, F. M. (1963), Naturally Occurring Oxygen Ring Compounds, Butter-worths, London.
De Lake, G. and Tiemann, F. (1893), Chem. Ber.26, 2010.
Dement, W. A. and Mabry, T. J. (1972), Phytochemistry 11, 1089.
Deverall, B. J. (1972), Proc. Roy. Soc. B. 181, 233.
Dewick, P. M., Barz, W. and Grisebach, H. (1969), Chem. Commun. 466.
Dhar, K. L. and Kalla, K. (1972), Phytochemistry 11, 3097.
Donnelly, D. M. X. and Fitzgerald, M. A. (1971), Phytochemistry 10, 3147.
Dyke, S. F., Ollis, W. D. and Sainsbury, M. (1963), Proc. chem. Soc. 179.
Eade, R. A., Hinterberger, H. and Simes, J. J. H. (1963), Aust. J. Chem.16, 188.
East, A. J., Ollis, W. D. and Wheeler, R. E. (1969), J. chem. Soc. (C) 365.
Elgamal, M. H. A. and Fayez, M. B. E. (1972), Indian J. Chem.10, 128.
Falshaw, C. P., Harmer, R. A., Ollis, W. D., Wheeler, R. E., Lalitha, V. R. and Subba Rao, N. V. (1969), J. chem. Soc. (C) 374.
Falshaw, C. P., Ollis, W. D., Moore, J. A. and Magnus, K. (1966), Tetrahedron, Suppl. No. 7 333.
Farkas, L. (1973), personal communication.
Farkas, L. and Nogradi, M. (1964), Tetrahedron Letters 3919.
Farkas, L., Varady, J. and Gottsegen, A. (1963), Chem. Ber.96, 1865.
Francis, C. M., Millington, A. J. and Bailey, E. T. (1961), Aust.J. argic. Res.18, 47.
Friedlander, A. and Sklarz, B. (1971), Experientia 27, 762.
Fukami, H. and Nakajima, M. (1971). In Naturally Occurring Insecticides (M. Jacobsen and D. G. Crosby, eds.), pp. 71–97. Marcel Dekker Inc, New York.
Geoffroy, J. (1892), J. pharm. Chim.26, 454.
Geoghegan, M., O’Sullivan, W. I. and Philbin, E. M. (1966), Tetrahedron 22, 3209.
Gopinath, K. W., Kidwai, A. R. and Prakash, L. (1961), Tetrahedron 16, 201.
Gottlieb, O. R. (1973), personal communication.
Gottlieb, O. R. and Rocha, A. I. (1972), Phytochemistry 11, 1183.
Govindachari, T. R., Nagarajan, K., Pai, B. R. and Parthasarthy, P. C. (1957), J. chem. Soc. 545.
Grisebach, H. and Zilg, H. (1968), Ztsch. Naturf. 23b, 494.
Guggolz, J., Livingston, A. L. and Bickoff, E. M. (1961), J. agric Fd. Chem 9, 330.
Gyorgy, P., Murata, K. and Ikehata, H. (1964), Nature 203, 870.
Harborne, J. B. (1967), Comparative Biochemistry of the Flavonoids, Academic Press, London.
Harborne, J. B. (1969), Phytochemistry 8, 1449.
Harborne, J. B. (1971). In Chemotaxonomy of the Leguminosae (J. B. Harborne, D. Boulter and B. L. Turner), pp. 31–71. Academic Press, London.
Harborne, J. B., Gottlieb, 0. R. and Magalhaes, M. (1963), J. org. Chem. 28, 881.
Harborne, J. B., Gottlieb, O. R. and Magalhães, M. (1963), J. org. Chem.28, 881.
Harper, S. H., Kemp, A. D., Underwood, W. G. E. and Campbell, R. V. M. (1969), J. chem. Soc. (C) 1109.
Harper, S. H. and Underwood, W. G. E. (1965), J. chem. Soc. 4203.
Higgins, V. T. and Smith, D. G. (1972), Phytopathol.62, 235.
Highet, R. J. and Highet, P. F. (1967), J. org. Chem.32, 1055.
Imamura, H., Hibino, Y. and Ohashi, H. (1972), Mokuzai Gakkaishi 18, 6; (Chem. Abstr.77, 85677).
Imamura, H., Tanno, Y. and Takahashi, T. (1968), Mokuzai Gakkaishi 14, 295; (Chem. Abstr. 70, 44835). Ito, S., Fujise, Y. and Mori, A. (1965), Chem. Commun. 595.
Jackson, B., Owen, P. J. and Scheinmann, F. (1971), J. chem. Soc. (C) 3389.
Jain, A. C., Rohatgi, V. K. and Seshadri, T. R. (1967), Tetrahedron 23, 2499.
Jay, M., Lebreton, P. and Letoublon, R. (1971), Boissiera 19, 219.
Johnson, A. P. and Pelter, A. (1966), J. chem. Soc. 606.
Johnson, A. P., Pelter, A. and Stainton, P. (1966), J. chem. Soc. 192.
Jurd, L., Stevens, K. and Manners, G. (1972), Phyto chemistry 11, 2535.
Kasymov, A. U., Kondratenko, E. S. and Abubakirov, N. K. (1972), Khim Prir. Soedin. 8, 115; [Chem. Abstr. 77, 85584].
Keen, N. T., Sims, J. J., Erwin, D. C., Rice, E. and Partridge, J. E. (1971), Phytopathology 61, 1084.
King, F. E., Grundon, M. F. and Neil, K. Q. (1952), J. chem. Soc. 4580.
Krishnaswamy, N. R. and Prasanna, S. (1970), Indian J. Chem.8, 761.
Kukla, A. S. and Seshadri, T. R. (1962), Tetrahedron 18, 1443.
Kurosawa, K., Ollis, W. D., Redman, B. T., Sutherland, I. O., Gottlieb, O. R. and Alves, H. M. (1968b), Chem. Commun. 1265.
Kurosawa, K., Ollis, W. D., Redman, B. T., Sutherland, I. O., Oliveira, A. B., Gottlieb, O. R. and Alves, H. M. (1968a), Chem. Commun. 1263.
Lebreton, P., Markham, K. R., Swift, W. T., Oung-Boran and Mabry, T. J. (1967), Phytochemistry 6, 1675.
Lindsay, R. and Kelly, R. W. (1910), Aust Veter. J.46, 219.
Livingston, A. L., Bickoff, E. M., Lundin, R. E. and Jurd, L. (1964), Tetrahedron 20, 1963.
Livingston, A. L., Witt, S. C., Lundin, R. E. and Bickoff, E. M. (1965), J. org. Chem.30, 2353.
Malhotra, A., Murti, V. V. S. and Seshadri, T. R. (1967), Tetrahedron 23, 405.
Markham, K. R., Mabry, T. J. and Swift, W. T. (1968), Phytochemistry 7, 803.
Markham, K. R., Mabry, T. J. and Swift, W. T. (1970), Phytochemistry 9, 2359.
Matos, F. J. D. B., Gottlieb, O. R., Ollis, W. D. and Andrade, C. H. S. (1970), An. Acad. Brasil. Ciena 42, 61.
McGookin, A., Robertson, A. and Whalley, W. B. (1940), J. chem. Soc. 787.
McMurray, T. B. H., Martin, E., Donnelly, D. M. X. and Thompson, J. C. (1972), Phytochemistry 11, 3283.
Morgan, J. W. W. and Orsler, R. J. (1967), Chem. Ind. 1173.
Murakami, T., Nisikawa, Y. and Ando, T. (1960). Chem. pharm. Bull. (Tokyo) 8, 688.
Nairn, M., Gestetner, B., Kirson, I., Birk Y. and Bondi, A. (1973), Phytochemistry 12, 169.
Narasimhachari, N. and Seshadri, T. R. (1952), Proc. Indian Acad. Sci.35A, 202.
Narayanan, V. and Seshadri, T. R. (1971), Indian J. Chem.9, 14.
Oliveira, A. B., Gottlieb, O. R., Goncalves, T. M. M. and Ollis, W. D. (1971a), An. Acad. Brasil. Cienc.43, 129.
Oliveira, A. B., Gottlieb, O. R. and Ollis, W. D. (1968), An. Acad. Brasil Cienc.40, 147.
Oliveira, A. B., Gottlieb, O. R., Ollis, W. D. and Rizzini, C. T. (1971b), Phytochemistry 10, 1863.
Oliveira, A. B., Silva, L. G. F. and Gottlieb, O. R. (1972), Phytochemistry 11, 3515.
Ollis, W. D. (1962). In The Chemistry of Flavonoid Compounds (T. A. Geissman, ed.), p. 353–405. Pergamon Press, Oxford.
Ollis, W. D. (1966), Experientia 22, 777.
Ollis, W. D. (1968). In Recent Advances in Phytochemistry (T. J. Mabry, R. E. Alston and V. C. Runeckles, eds.), Vol. 1, pp. 329–378. Appleton-Century-Crofts, New York.
Ollis, W. D., Ramsay, M. V. J. and Sutherland, I. O. (1965), Aust. J. Chem.18, 1787.
Ollis, W. D., Rhodes, C. A. and Sutherland, I. O. (1967), Tetrahedron 23, 4741.
Pachler, K. G. R. and Underwood, W. G. E. (1967), Tetrahedron 23, 1817.
Paris, R. R. and Faugeras, G. (1963), Séances Acad. Sci.257, 1728.
Parthasarathy, M. R., Puri, R. N. and Seshadri, T. R. (1969), Indian J. Chem.7, 118.
Pelter, A. and Amenechi, P. I. (1969), J. chem. Soc. (C) 887.
Pelter, A. and Stainton, P. (1966), J. chem. Soc. (C) 701.
Pelter, A., Stainton, P. and Barber, M. (1965a), J. heterocycl Chem.2, 262.
Pelter, A., Stainton, P., Johnson, A. P. and Barber, M. (1965b), J. heterocycl. Chem.2, 256.
Perrin, D. R. (1964), Tetrahedron Letters 29.
Perrin, D. R. and Bottomley, W. (1962), J. Am. chem. Soc.84, 1919.
Perrin, D. R. and Cruickshank, I. A. M. (1969), Phytochemistry 8, 971.
Perrin, D. R., Whittle, C. P. and Batterham, T. J. (1972), Tetrahedron Letters 1673.
Prakash, L., Zaman, A. and Kidwai, A. R. (1965), J. org. Chem.30, 3561.
Purushothaman, K. K., Kishore, V. M., Narayanaswami, V. and Connolly, J. D. (1971), J. chem. Soc. (C)2420.
Rail, G. J. H., Bring, A. J. and Engelbrecht, J. P. (1972), J. S. African chem. Inst.25, 25.
Rail, G. J. H., Engelbrecht, J. P. and Brink, A. J. (1970), Tetrahedron 26, 5007.
Rail, G. J. H., Engelbrecht, J. P. and Brink, A. J. (1971), J. S. African chem. Inst. 24, 56. 24, 56.
Saitoh, T. and Shibata, S. (1969), Chem. pharm. Bull. (Tokyo) 17, 729.
Schwarz, J. S. P., Cohen, A. I., Ollis, W. D., Kalzka, E. A. and Jackman, L. M. (1964), Tetrahedron 20, 1317.
Seshadri, T. R. (1964). In Symposium on Phytochemistry, Hong Kong 1961 (H. R. Arthur, ed.), pp. 145–163. Hong Kong University Press.
Seshadri, T. R. (1972), Phytochemistry 11, 881.
Shabbir, M. and Zaman, A. (1970), Tetrahedron 26, 5041.
Shabbir, M., Zaman, A., Crombie, L., Tuck, B. and Whiting, D. A. (1968), J. chem. Soc. 1899.
Shamma, M. and Stiver, L. D. (1969), Tetrahedron 25, 3887.
Shibata, S. and Hishikawa, Y. (1963), Chem. pharm. Bull. (Tokyo) 11, 167.
Shibata, S., Murata, T. and Fujita, M. (1963), Chem. pharm. Bull. (Tokyo) 11, 382.
Shibata, S. and Saitoh, T. (1968), Chem. pharm. Bull. (Tokyo) 16, 1932.
Simonitsch, E., Frei, H. and Schmid, H. (1957), Monatsh. Chem.88, 541.
Sims, J. J., Keen, N. T. and Honwad, V. K. (1972), Phytochemistry 11, 827.
Smith, D. G., Mclnnes, A. G., Higgin, V. J. and Millar, K. L. (1971), Physiol. Pl. Pathol.1, 41.
Spencer, R. R., Bickoff, E. M., Lundin, R. E. and Knuckles, B. E. (1966a) J. agric. Fd. Chem.14, 162.
Spencer, R. B., Knuckles, B. E. and Bickoff, E. M. (1966b), J. org. Chem.31, 988.
Suginome, H. (1959), J. org. Chem.24, 1655.
Suginome, H. (1966a), Bull. chem. Soc. Japan 39, 1529.
Suginome, H. (1966b), Bull. chem. Soc. Japan 39, 1544.
Suginome, H. and Iwadare, T. (1962), Experientia 18, 163.
Suginome, H. and Kio, T. (1966), Bull chem. Soc. Japan 39, 1541.
Tamura, S., Chang, C. F., Suzuki, A. and Kumai, S. (1969), Agric. biol Chem.33, 391.
Verbit, L. and Clark-Lewis, J. W. (1968), Tetrahedron 24, 5519.
Whalley, W. B. (1959). In The Pharmacology of Plant Phenolics (J. W. Fairbairn, ed.), pp. 27–37. Academic Press, London and New York.
Wong, E. (1963), J. org. Chem.28, 2336.
Wong, E. (1970), Fortschr. Chem. organ. Naturst.28, 1.
Wong, E. and Latch, G. C. M. (1971a), New Zeal J. agric. Res.14, 633.
Wong, E. and Latch, G. C. M. (1971b), Phytochemistry 10, 465.
Wong, E., Mortimer, P. I. and Geissman, T. A. (1965), Phytochemistry 4, 89.
Wood, R. K. S. (1972), Proc. Roy. Soc. B 181, 213.
Zilg, H. and Grisebach, H. (1968), Phytochemistry 7, 1765.
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Wong, E. (1975). The Isoflavonoids. In: Harborne, J.B., Mabry, T.J., Mabry, H. (eds) The Flavonoids. Springer, Boston, MA. https://doi.org/10.1007/978-1-4899-2909-9_14
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