Abstract
This review, which covers the literature up to 1989, generalizes advances in the field of the study of the photochemical isomers of colchicine and tropolone alkaloids related to it. Information is given on their natural sources, methods of isolation, structure, and configuration, and photochemical and thermal interconversions. Characteristics distinguishing them from the topolone alkaloids in their UV, IR, mass, and2H and13C NMR spectra of the photochemical isomers are pointed out.
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Literature cited
M. K. Yusupov and A. S. Sadykov, Khim. Prir. Soedin., 3 (1978).
H. J. Kuhn, O. A. Neumuller, and G. O. Schenck, Photochemische und thermische Umwandlungen einiger Colchicum-Alkaloide und ihrer Lumiverbindungen. Westdeutscherverlag, Köln-Opladen, No. 1624 (1966).
F. Šantavý, in: The Chemistry of Plant Substances [in Russian], Fan, Tashkent (1972), p. 7.
M. K. Yusupov, in: The Chemistry of Plant Substances [in Russian], Fan, Tashkent (1972), p. 19.
D. J. Pasto, in: Organic Photochemistry (ed. O. L. Chapman), Marcel Dekker, New York Vol. 1 (1967), p. 155.
H. F. Koch, Adv. Alicyclic Chem.,1, 268 (1966).
I. A. Alov, Advances in Science and Technology, Cytology. Vol. 2, Mitotic Cell Division [in Russian], Moscow (1965), p. 173.
A. A. Kraevskii, Bioorg. Khim.,4, 853 (1978).
L. Wilson and I. Meza, J. Cell Biol.,58, 709 (1973).
H. F. Linskens and W. Wulf, Naturwissenschaften,40, 487 (1953).
D. Flanagan and J. R. Warr, FEBS Lett.,80, 14 (1977).
S. B. Mizel and L. Wilson, Biochemistry,11, 2573 (1972).
F. Šantavý, Alkaloidy Ocunovitych Rostlin a Jejich Derivaty. [Alkaloids of Plants of the GenusColchicum and Their Derivatives], Stat. Zdrav. nakl. Prague (1958).
R. Grewe, Naturwissenschaften,33, 187 (1946).
F. Šantavý, Collect. Czech. Chem. Commun.,16, 665 (1951).
F. Šantavý, Collect. Czech. Chem. Commun.,15, 552 (1950).
F. Šantavý and T. Reichstein, Helv. Chim. Acta,33, 1606 (1950).
R. Grewe and W. Wulf, Berichte,84, 621 (1951).
K. Bursian, Berichte,71, 245 (1938).
A. D. Kemp and D. S. Tarbell, J. Am. Chem. Soc.,72, 243 (1950).
E. Forbes, J. Chem. Soc., 3864 (1955).
H. R. Arnstein, D. S. Tarbell, N. R. Huang, and G. P. Scott, J. Am. Chem. Soc.,70, 1669 (1948).
P. D. Gardner, R. L. Brandon, and G. R. Haynes, J. Am. Chem. Soc.,79, 6334 (1957).
O. L. Chapman, H. G. Smith, and K. W. King, J. Am. Chem. Soc.,85, 803 (1963).
L. Canonica, B. Danieli, P. Manitto, and G. Russo, Tetrahedron Lett., 607 (1969).
L. Canonica, B. Danieli, P. Manitto, G. Russo, A. Bonati, and E. Bombardelli, Gazz. Chim. Ital.,99, 1059 (1969).
G. O. Schenck, H. J. Kuhn, and O. A. Neumiller, Tetrahedron Lett.,12 (1961).
O. L. Chapman and H. G. Smith, J. Am. Chem. Soc.,83, 3914 (1961).
O. L. Chapman, H. G. Smith, and R. W. King, J. Am. Chem. Soc.,85, 806 (1963).
O. L. Chapman and D. J. Pasto, J. Am. Chem. Soc.,81, 5510 (1959).
K. V. Scherer, J. Am. Chem. Soc.,90, 7352 (1968).
H. Corrodi and E. Hardegger, Helv. Chim. Acta,38, 2030 (1955).
H. Lettre and T. J. Fitzgerald, Acta Prob. Cancerol.,2, 200 (1968).
W. G. Dauben and D. A. Cox, J. Am. Chem. Soc.,85, 2130 (1963).
O. L. Chapman, G. H. Smith, and P. A. Barks, J. Am. Chem. Soc.,85, 3171 (1963).
W. G. Dauben, K. Koch, O. L. Chapman, and S. L. Smith, J. Am. Chem. Soc.,83, 1768 (1961).
S. N. Maity and B. Bhattacharyya, FEBS Lett.,218, 182 (1987).
M. K. Yusupov and A. S. Sadykov, Zh. Obshch. Khim.,34, 1672 (1969).
A. S. Sadykov and M. K. Yusupov, Nauchn. Tr. Tashkentsk Gos. Univ. im. V. I. Lenin, Estestv. Nauki, No. 203, 15 (1962).
A. S. Sadykov, M. K. Yusupov, and B. Chommadov, Rast. Res.,5, 441 (1969).
A. M. Usmanov, B. Chommadov, and M. K. Yusupov, Khim. Prir. Soedin., 81 (1985).
A. M. Usmanov, B. Chommadov, M. K. Yusupov, and Kh. A. Aslanov, Khim. Prir. Soedin., 248 (1985).
B. Chommadov, A. M. Usmanov, and M. K. Yusupov, Khim. Prir. Soedin., 808 (1985).
R. V. Alikulov, B. Chommadov, D. M. Pratova, and M. K. Yusupov, Khim. Prir. Soedin., 464 (1985).
M. K. Yusupov, D. A. Abdullaeva, Kh. A. Aslanov, A. S. Sadykov, Dokl. Akad. Nauk,208, 1123 (1973).
N. L. Mukhamed'yarova, M. K. Yusupov, M. G. Levkovich, Kh. A. Aslanov, and A. S. Sadykov, Khim. Prir. Soedin., 354 (1976).
D. A. Abdullaeva, M. K. Yusupov, Kh. A. Aslanov, Khim. Prir. Soedin., 783 (1986).
M. K. Yusupov, B. Chommadov, Kh. A. Aslanov, Khim. Prir. Soedin., 419 (1985).
H. Roigt and M. Leblanc, Can. J. Chem.,50, 1959 (1972);51, 2821 (1959).
I. L. Brunetti, E. J. H. Bechara, G. Cliento, and E. H. White, Photochem. Photobiol.,36, 245 (1982).
A. S. Sadykov, Problems of the Regulations, Synthesis, and Metabolism of Natural Compounds [in Russian], FAN, Tashkent (1978), p. 15.
F. Šantavý, Acta Univ. Palack. Olomic,90, 15 (1979).
F. Šantavý, Pharm. Acta Helv.,25, 248 (1950).
H. Potešilová, J. Wiedermannova, and F. Šantavý, Collect. Czech. Chem. Commun.,34, 3642 (1969).
L. Canonica, B. Danieli, P. Manitto, et al., Chim. Ind. (Ital.)49, 1304 (1967).
Kh. Turdikulov, M. K. Yusupov, and A. S. Sadykov, Khim. Prir. Soedin., 541 (1971).
P. Bellet and M. D. Gerard, Ann. Pharm. France,119, 587 (1961).
H. Potešilova, J. Šantavý, A. El-Hamidi, and F. Šantavý, Coll. Czech. Chem. Commun.,34, 3540 (1969).
O. A. Neumuller, H. J. Kuhn, G. O. Schenck, and F. Šantavý, Ann. Chem.,674, 122 (1964).
J. Potešilova, J. Hrbek, and F. Šantavý, Coll. Czech. Chem. Commun.,32, 141 (1967).
B. Chommadov, M. K. Yusupov, A. S. Sadykov, Khim. Prir. Soedin., 82 (1970).
Kh. Turdikulov, M. K. Yusupov, and A. S. Šadykov, Khim. Prir. Soedin., 502 (1972).
F. Šantavý and V. Macak, Coll. Czech. Chem. Commun.,19, 805 (1954).
F. Šantavý, Coll. Czech. Chem. Commun.,28, 3413 (1963).
O. Gašic, H. Potešilová, and F. Šantavý, Planta Med.,30, 75 (1976).
H. Potešilová, L. Hruban, and F. Šantavý, Coll. Czech. Chem. Commun.,41, 3146 (1976).
L. Pijewska, J. L. Kaul, R. K. Joshi, and F. Šantavý, Coll. Czech. Chem. Commun.,32, 158 (1967).
B. Chommadov, M. K. Yusupov, and A. S. Sadykov, Khim. Prir. Soedin., 275 (1970).
B. Chommadov, M. K. Yusupov, F. G. Kamaev, and A. S. Sadykov, Izv. Akad. Nauk TurkmSSR. Ser. Fiz.-Tekhnol. Khim. Geol. Nauk, 111 (1970).
F. Šantavý, Coll. Czech. Chem. Commun.,35, 2857 (1970).
H. Potešilová, P. Sedmera, D. Guenard, and V. simanek, Planta Med., 344 (1985).
A. D. Gross, J. Hrbek, Jr., and F. Šantavý, Beitrage zur Biochemie und Physiologie von Naturstoffen, VEB Gustav Fischer Verlag, Jena (1965), p. 97.
A. Sangster, and K. Stuart, Chem. Rev.,65, 69 (1965).
J. Hrbek, J. P. Jennings, W. Klyne, and F. Šantavý, Coll. Czech. Chem. Commun.,29, 2822 (1964).
J. Hrbek, L. Hruban, V. Šimanek, F. Šantavý, G. Snatzke, and S. S. Yemul, Coll. Czech. Chem. Commun.,47, 2258 (1982).
N. S. Bhacca, F. Johnson, and J. N. Shoolery, High Resolution NMR Spectra Catalog. Varian Associates, Paolo Alto, Calif., Vol. 2 (1963).
G. S. Ricca and B. Danieli, Gazz. Chim. Ital.,99, 133 (1969).
D. Meksuriyen, L.-J. Lin, and G. A. Cordell, J. Nat. Prod.,51, 88 (1988).
F. G. Kamaev, M. G. Levkovich, H. L. Mukhamed'yarova, M. K. Yusupov, and A. S. Sadykov, in: Soviet-Indian Symposium on the Chemistry of Natural Compounds. Abstracts of Lectures, Erevan (1978), p. 35.
C. D. Hufford, C. C. Collins, and A. M. Clark, J. Pharm. Sci.,68, 1239 (1979).
C. D. Hufford, H. G. Capraro, and A. Brossi, Helv. Chim. Acta,63, 50 (1980).
B. Danieli, G. Palmisano, G. S. Ricca, Gazz. Chim. Ital.,110, 351 (1980).
A. Blade-Font, R. Muller, J. Elguero, R. Faure, and E.-J. Vincent, Chem. Lett., 233 (1979).
S. P. Singh, S. S. Parmar, V. I. Stenberg, and S. A. Farnum, Spectrosc. Lett.,10, 1001 (1977).
J. M. Wilson, M. Ohashi, H. Budzikiewicz, C. Djerassi, Tetrahedron,19, 2225 (1963).
E. Kh. Timbekov, A. K. Kasimov, M. K. Yusupov, Kh. A. Aslanov, and A. S. Sadykov, Izv. Akad. Nauk TurkmSSR, Ser. Fiz.-Technol. Khim. Geol. Nauk (1976).
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Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 147–165, March–April, 1990.
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Chommadov, B.C., Yusupov, M.K. & Sadykov, A.S. Photochemical isomers of tropolone alkaloids. Chem Nat Compd 26, 113–128 (1990). https://doi.org/10.1007/BF00607526
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DOI: https://doi.org/10.1007/BF00607526