Advertisement

Chemistry and Sources of Mono- and Bicyclic Sesquiterpenes from Ferula Species

  • A. G. González
  • J. Bermejo Barrera
Part of the Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products book series (FORTCHEMIE (closed), volume 64)

Abstract

The exclusively Old World genus Ferula belongs to the family Umbelliferae (tribe Peucedaneae, subtribe Peucedaninae) (1) with some 130 species distributed throughout the Mediterranean area and Central Asia. The highest concentration of species is in the former USSR and neighbouring countries where nearly 100 species have been described, about 60 of them endemic. More than twenty species have been reported in Iran and three in the Canary Islands off the Atlantic coast of Africa (Figs. 1, 2 and 3).

Keywords

Hydroxy Group Sesquiterpene Lactone Isopropyl Group Oxirane Ring Secondary Hydroxy Group 
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.
    Korovin, E.P.: Illustrated Monograph of the Genus Ferula. Tashkent: 1947. See ref. 28.Google Scholar
  2. 2.
    Saidkhodzhaev, A.I.: Sesquiterpene Derivatives of the Genus Ferula. Khim Chem Abstr. 4, 437 (1979); Chem. Abstr., 92, 76670p (1980).Google Scholar
  3. 3.
    Kir’yalov, N.P.: Coumarins from Plants of the Genus Ferula. Tr. Botan. Inst., Akad. Nauk SSSR, Ser. 5, Rast. Syr’e, 12, 82 (1965)Google Scholar
  4. Kir’yalov, N.P.: Coumarins from Plants of the Genus Ferula. Tr. Botan. Inst., Akad. Chem. Abstr., 59, 5255h (1966).Google Scholar
  5. 4.
    Kir’yalov, N.P., and V.Yu. Bagirov: Structure of Karatavikin. Khim. Prir. Soedin., 3, 223 (1967)Google Scholar
  6. Kir’yalov, N.P., and V.Yu. Bagirov: Structure of Karatavikin. Chem. Abstr., 68, 68829m (1968).Google Scholar
  7. 5.
    Kir’yalov, N.P., and V.Yu. Bagirov: Structure of Karatavic Acid. Khim. Prir. Soedin., 4, 283 (1968)Google Scholar
  8. Kir’yalov, N.P., and V.Yu. Bagirov: Structure of Karatavic Acid. Chem. Abstr., 70, 77715q (1969).Google Scholar
  9. 6.
    Kir’yalov, N.P., and S.D. Movchan: Structure of Samarkandine and Samarkandone, Coumarin Compounds of Ferula samarkandica. Khim. Prir. Soedin., 4, 73 (1968)Google Scholar
  10. Kir’yalov, N.P., and S.D. Movchan: Structure of Samarkandine and Samarkandone, Coumarin Compounds of Ferula samarkandica. Chem. Abstr., 69, 59040r (1968).Google Scholar
  11. 7.
    Kir’yalov, N.P.: The Coumarin, Badrakemin, from the Roots of Ferula badrakema. Khim. Prir. Soedin., 3, 363 (1967)Google Scholar
  12. Kir’yalov, N.P.: The Coumarin, Badrakemin, from the Roots of Ferula badrakema. Chem. Abstr., 69, 35865n (1968).Google Scholar
  13. 8.
    Kir’yalov, N.P., and S.D. Movchan: Structure of Gummosine. Khim. Prir. Soedin., 2, 383 (1966)Google Scholar
  14. Kir’yalov, N.P., and S.D. Movchan: Structure of Gummosine. Chem. Abstr., 67, 11394r (1967).Google Scholar
  15. 9.
    Kir’yalov, N.P., and S.V. Serkerov: Structure of Badkhysin. Khim. Prir. Soedin., 4, 341 (1968)Google Scholar
  16. Kir’yalov, N.P., and S.V. Serkerov: Structure of Badkhysin. Chem. Abstr., 70, 78177c (1969).Google Scholar
  17. 10.
    Kir’yalov, N.P.: Species of the Genus Ferula as Sources of New Biologically Active Compounds. Tr. Bot. Inst., Akad. Nauk. SSSR, Ser. 5, 15, 129 (1968)Google Scholar
  18. Kir’yalov, N.P.: Species of the Genus Ferula as Sources of New Biologically Active Compounds. Tr. Bot. Inst., Akad.Chem. Abstr., 27, 3185r (1969).Google Scholar
  19. 11.
    Pimenov, M.G., Yu.E. Sklyar, A.A. Savina, and Yu.V. Baranova: Chemosystematics of Section Palaeonarthex of the Genus Ferula. Biochem. Syst. Ecol., 10, 133 (1982).CrossRefGoogle Scholar
  20. 12.
    Ashraf, M., R. Ahmad, S. Mahamood, and M.K. Bhatty: Studies on the Essential Oils of the Pakistani Species of the Family Umbelliferae, XLV: Ferula assafoetida, Linn (Herra Hing) Gum Oil. Pak. J. Sci. Ind. Res., 23, 68 (1980)Google Scholar
  21. Ashraf, M., R. Ahmad, S. Mahamood, and M.K. Bhatty: Studies on the Essential Oils of the Pakistani Species of the Family Umbelliferae, XLV: Ferula assafoetida, Linn (Herra Hing) Chem. Abstr., 94, 127135u (1981).Google Scholar
  22. 13.
    Courchet, L.: Les Ombellifères en Général et les Espèces Usitées en Pharmacie en Particulier. Montpellier: Imprimerie Cristin, Serre and Ricome. 1982.Google Scholar
  23. 14.
    Uphof, J.C.TH.: Dictionary of Economic Plants, 2nd Ed. Verlag von J. Cramer. 1968.Google Scholar
  24. 15.
    Culbreth, D.M.R.: A Manual of Materia Medica and Pharmacology, 6th Ed. Philadelphia and New York: Lea and Febiger. 1917.Google Scholar
  25. 16.
    Alhazini, H.M.G.: Sesquiterpenoids of Ferula Species. J. Chem. Soc. Pak., 10, 482 (1988)Google Scholar
  26. 17.
    Haagen-Smith, A.J.: The Essential Oils. New York: Van Nostrand. 1948.Google Scholar
  27. 18.
    Ruzicka, L.: The Isoprene Rule and Biogenesis of Terpenic Compounds. Experientia, 9, 357 (1953).CrossRefGoogle Scholar
  28. 19.
    Hendrickson, J.B.: Stereochemical Implications in Sesquiterpene Biogenesis. Tetrahedron, 7, 82 (1959).CrossRefGoogle Scholar
  29. 20.
    Agvanoff, B.W., H. Eggeren, U. Henning, and F. Lynen: Isopentenol PyIophosphate Isomerase. J. Amer. Chem. Soc., 81, 1254 (1959).CrossRefGoogle Scholar
  30. 21.
    Woodward, R.B.: Structure and the Absorption Spectra of a,O-Unsaturated Ketones. J. Amer. Chem. Soc., 63, 1123 (1941).CrossRefGoogle Scholar
  31. 22.
    Golovina, L.A., and A.I. Saidkhodzhaev: Esters of Ferula rubroarenosa. Khim. Prir. Soedin., 6, 712 (1978)Google Scholar
  32. Golovina, L.A., and A.I. Saidkhodzhaev: Esters of Ferula rubroarenosa. Chem. Abstr., 91, 2498w (1979).Google Scholar
  33. 23.
    Miski, M., T.J. Mabry, and O. Saya: New Daucane and Germacrane Esters from Ferula orientalis var. orientalis. J. Nat. Prod., 50, 829 (1987).CrossRefGoogle Scholar
  34. 24.
    Karavaeva, O.V., V.V. Kiseleva, G.K. Nikonov, and M.O. Karryev: Esters of Ferula ovina (Boiss). Izv. Akad. Nauk Kaz. SSR, Ser. Khim., 1, 80 (1989)Google Scholar
  35. Karavaeva, O.V., V.V. Kiseleva, G.K. Nikonov, and M.O. Karryev: Esters of Ferula ovina (Boiss). Izv. Akad. Chem. Abstr., 111, 4208g (1989).Google Scholar
  36. 25.
    Cordell, G.A.: Biosynthesis of Sesquiterpenes. Chem. Rev., 76, 425 (1976).CrossRefGoogle Scholar
  37. 26.
    Soucek, M.: On Terpenes, CXLVIII: Biosynthesis of Carotol in Daucus carota L. A Contribution to Configuration of Carotol and Daucol. Collect. Czech. Chem. Commun., 27, 2929 (1962).Google Scholar
  38. 27.
    Sagitdinova, G.V., A.I. Saidkhodzhaev, and V.M. Malikov: Structure of Fertinidine and Fertinicine. Khim. Prir. Soedin., 1, 42 (1980)Google Scholar
  39. Sagitdinova, G.V., A.I. Saidkhodzhaev, and V.M. Malikov: Structure of Fertinidine and Fertinicine. Chem. Abstr., 93, 46865j (1980).Google Scholar
  40. 28.
    Korovin, E.: Genesis Ferula (Tourn) L. Monographia Illustrata, pp. 9, 59. Tashkent: Editio Academia Scientarum USSR. 1947.Google Scholar
  41. 29.
    Miski, M., T.J. Mabry, and O. Saya: Apiene Esters from Ferula haussknechtii. Phytochem., 26, 1733 (1987).CrossRefGoogle Scholar
  42. 30.
    Bohlmann, F., C. Zdero, and M. Grenz: Neue Sesquiterpene der Gattung Othonna. Chem. Ber., 107, 3928 (1974).CrossRefGoogle Scholar
  43. 31.
    Bohlmann, F., C. Zdero, R.M. King, and H. Robinson: Humulene Derivatives from Acritoppapus prunifolius. Phytochem., 21, 147 (1982).CrossRefGoogle Scholar
  44. 32.
    Eldahmy, S., J. Jakupovic, F. Bohlmann, and T.M. Sarg: New Humulene Derivatives from Asteriscus graveolens. Tetrahedron, 41, 309 (1985).CrossRefGoogle Scholar
  45. 33.
    Gonzalez, A.G, J. Bermejo, J.G. Diaz, and L. Arancibia: Humulenes and Other Constituents of Ferula latipinna. J. Nat. Prod., 51, 1140 (1988).CrossRefGoogle Scholar
  46. 34.
    Itokawa, H., H. Matsumoto, S. Mishashi, and Y. Iitaka: Two Novel Humulenoids from Torilis scabra D.C.. Chem. Lett., 1581 (1983).Google Scholar
  47. 35.
    Alan, F.T., M. Ozainne, R. Decorzant, and F. Naf: lO-Epijunenol, a New Cis Eudesmane Sesquiterpenoid. Tetrahedron, 32, 2261 (1976).CrossRefGoogle Scholar
  48. 36.
    Senda, I., and S. Imaizumi: 13C Pulse Fourier Transform NMR of Menthol Stereo-isomers and Related Compounds. Tetrahedron, 31 2905 (1975).Google Scholar
  49. 37.
    Feltkamp, H., and N.C. Franklin: Conformational Analysis by Nuclear Magnetic Resonance, VI: The Conformations of Sixteen Stereomeric 2,5-Dialkyl Cyclohexanols of the Menthol Type. Tetrahedron, 21 1541 (1965).Google Scholar
  50. 38.
    Brown, H.C., C.P. Garg, and K.T. Liu: The Oxidation of Secondary Alcohols in Diethyl Ether with Aqueous Chromic Acid. A Convenient Procedure for the Preparation of Ketones in High Epimeric Purity. J. Org. Chem., 36, 387 (1971).CrossRefGoogle Scholar
  51. 39.
    Asakawa, Y., G. Ourisson, and T. Aratani: New Sesquiterpene Lactone and Aldehyde of Frullania tamarisci subsp. oscura (Hepatieae). Tetrahedron Letters, 45, 3957 (1975).CrossRefGoogle Scholar
  52. 40.
    Niwa, M., A. Nishiyama, M. Iguchi, and S. Yamamura: SesquiterpeneS from Acorus calamus. Bull. Chem. Soc. Japan, 48, 2930 (1975).CrossRefGoogle Scholar
  53. 41.
    Naf, F., R. Decorzant, and W. Thommen: Regiospecific Intramolecular Aldol Condensation Induced by Conjugate Addition of Lithium Dimethylcuprate to C-oxoa,ß-Enones. HeIv. Chim. Acta, 58, 1808 (1975).CrossRefGoogle Scholar
  54. 42.
    Bizhanova, K., and A.I. Saidkhodzhaev: The Structure of Xeroferin. Khim. Prir. Soedin., 5, 581 (1978); Chem. Abstr., 90, 104150y (1979).Google Scholar
  55. 43.
    Sriramanan, M.C., B.A. Nagasampagi, R.C. Pandey, and S. Dev: Studies in Sesquiterpenes, XLIX: Sesquiterpenes from Ferula jaeschkeana Vatke (Part I): Jaeschkeanadiol-Structure, Stereochemistry. Tetrahedron, 29, 985 (1973).CrossRefGoogle Scholar
  56. 44.
    Chiurdoglu, G., and M. Descamps: Contribution a l’Etude des Composes Sesquiterpeniques, IV: Etude de la Structure du Carotol, Alcool C15H26O de l’Essence de Daucus carota. Tetrahedron, 8, 271 (1960).CrossRefGoogle Scholar
  57. 45.
    Holub, M., J. Tax, P. Sedmera, and F. Sorm: On Terpenes, CCVIL: Contribution to the Stereochemistry of Substances with Daucane Skeleton and the Determination of Absolute Configuration of Laserpitine. Coll. Czech. Chem. Comm., 35, 3597 (1970).Google Scholar
  58. 46.
    Budzikiewicz, H., C. Djerassi, and D.N. Williams: Mass Spectrometry of Organic Compounds, p. 94. San Francisco: Holden-Day. 1967.Google Scholar
  59. 47.
    Curtis, R.G., I. Heilbron, E.R.H. Jones, and G.F. Woods: The Chemistry of Triterpenes, XIII: The Further Characterization of Polyporenic Acid A. J. Chem. Soc., 457 (1953).Google Scholar
  60. 48.
    Hotus, M., Z. Samek, V. Herout, and F. Sorm: On Terpenes, CLXXXIII: The Constitution of Laserpitine. A Sesquiterpenic Compound from Laserpitium latifolium L. Root. Coll. Czech. Chem. Comm., 32, 591 (1967).Google Scholar
  61. 49.
    Takeda, K., and H. Minato: Sesquiterpenoids, I: Absolute Configuration of Guaiol. Chem. Pharm. Bull., 9, 619 (1961)CrossRefGoogle Scholar
  62. Takeda, K., and H. Minato: Sesquiterpenoids, I: Absolute Configuration of Guaiol. Chem. Abstr., 56, 10193d (1962).Google Scholar
  63. 50.
    Bhacca, N.S., and D.H. Williams: Applications of NMR Spectroscopy in Organic Chemistry, pp. 82–83. San Francisco: Holden-Day. 1964.Google Scholar
  64. 51.
    Garg, S.N., S.K. Agarwal, V.P. Mahajan, and S.N. Rastogi: Feruginidin and Ferugin, Two New Sesquiterpenoids Based on the Carotane Skeleton from Ferula jaeschkeana. J. Nat. Prod., 50, 253 (1987).CrossRefGoogle Scholar
  65. 52.
    Garg, S.N., and S.K. Agarwal: Further New Sesquiterpenes from Ferula jaeschkeana. J. Nat. Prod., 51, 771 (1988).CrossRefGoogle Scholar
  66. 53.
    Garg, S.N., VishwapaulS. N. Rastogi: Isocarotane and Carotane Derivatives from Ferula jaeschkeana. Phytochem., 29, 531 (1990).CrossRefGoogle Scholar
  67. 54.
    Miski, M., A. Ulubelen, and T.J. Mabry: Six Sesquiterpene Alcohol Esters from Ferula elaeochytris. Phytochem., 22, 2231 (1983).CrossRefGoogle Scholar
  68. 55.
    Diaz, J.G., B.M. Fraga, A.G. Gonzalez, P. Gonzalez, and M.G. Hernandez: Eight Carotane Sesquiterpenes from Ferula linkii. Phytochem., 23, 2541 (1984).CrossRefGoogle Scholar
  69. 56.
    Diaz, J.G., B.M. Fraga, A.G. Gonzalez, M.G. Hernandez, and A. Perales: Carotane Sesquiterpenes from Ferula linkii. Phytochem., 25, 1161 (1986).CrossRefGoogle Scholar
  70. 57.
    Garg, S.N., and K. Agarwal: New Sesquiterpenes from Ferula jaeschkeana. Planta Med., 53, 341 (1987).CrossRefGoogle Scholar
  71. 58.
    Bizhanova, K.B., A.I. Saidkhodzaev, and V.M. Malikov: Structure Of Jaeschferin. Khim. Prir. Soedin., 7, 127 (1980)Google Scholar
  72. Bizhanova, K.B., A.I. Saidkhodzaev, and V.M. Malikov: Structure Of Jaeschferin. Chem. Abstr., 93, 71992f (1980).Google Scholar
  73. 59.
    Ahmed, A.A.: New Sesquiterpenes from Ferula sinaica. J. Nat. Prod., 53, 483 (1990).CrossRefGoogle Scholar
  74. 60.
    Miski, M., A. Ulubelen, T.J. Mabry, W.H. Watson, I. Vickovic, and M. Holub: A New Sesquiterpene Ester from Ferula tingitana. Tetrahedron, 40, 5197 (1984).CrossRefGoogle Scholar
  75. 61.
    Holub, M., Z. Samek, V. Herout, and F. Sorm: Terpenes, Clxxxvii: Constitution of Isolaserpitin, Deoxodehydrolaserpitin and Laserpitinol. Monatsh. Chemie, 98, 1138 (1967).CrossRefGoogle Scholar
  76. 62.
    Miski, M., and T.J. Mabry: New Daucane Esters from Ferula tingitana. J. Nat. Prod., 49, 657 (1986).CrossRefGoogle Scholar
  77. 63.
    Miski, M., and T.J. Mabry: Daucane Esters from Ferula communis subsp. communis. Phytochem., 24, 1735 (1985).CrossRefGoogle Scholar
  78. 64.
    Miski, M., and T.J. Mabry: Fercolide, A Type of Sesquiterpene Lactone from Ferula communis subsp. communis and the Correct Structure of Vaginatin. Phytochem., 25, 1673 (1986).CrossRefGoogle Scholar
  79. 65.
    Holub, M., R. DE Groote, V. Herout, and F. Sorm: Plant Substances, XXVIII: Oxygen-Containing Components of Light Petroleum Extract of Laser trilobum (L.) Borkh Root. Structure of Laserine. Coll. Czech. Chem. Comm., 33, 2911 (1968).Google Scholar
  80. 66.
    Pinar, M., M. Rico, and B. Rodriguez: Laserine Oxide, an Epoxide from Guillonea scraba. Phytochem., 21, 735 (1982).CrossRefGoogle Scholar
  81. 67.
    Fraga, B.M., A.G. Gonzalez, P. Gonzalez, M.G. Hernandez, and C.L. Larruga: Carotane Sesquiterpenes from Ferula lancerottensis. Phytochem., 24, 501 (1985).CrossRefGoogle Scholar
  82. 68.
    Hassan, A., and G. Alhazimi: More Sesquiterpenes from Ferula sinaica. Oriental. J. Chem., 4, 200 (1988).Google Scholar
  83. 69.
    Ahmed, A.A.: Daucanes and Other Constituents from Ferula sinaica. Phytochem., 30, 1207 (1991).CrossRefGoogle Scholar
  84. 70.
    Fraga, B.M., M.G. Hernandez, J.G. Diaz, A.G. Gonzalez, and P. Gonzalez: Carotane Sesquiterpenes from Ferula linkii. Phytochem., 25, 2883 (1986).CrossRefGoogle Scholar
  85. 71.
    Lamnaouer, D., M. Martin, D. Malho, and B. Bodo: Isolation of Daucane Esters from Ferula communis var. berivifolia. Phytochem., 28, 2711 (1989).CrossRefGoogle Scholar
  86. 72.
    Razdan, T.K., B. Qadri, M.A. Qurishi, M.A. Khuroo, and P.K. Kachroo: Sesquiterpene Esters and Sesquiterpene-Coumarin Ethers from Ferula jaeschkeana. Phytochem., 28, 3389 (1989).CrossRefGoogle Scholar
  87. 73.
    Zalkow, L.H., M.G. Clower, M.M. Gordon, and L.T. Gelbaum: Chemistry of the Carotane Sesquiterpenes, V: Biosimulated Conversions. J. Nat. Prod., 43, 382 (1980).CrossRefGoogle Scholar
  88. 74.
    Zalkow, L.H., M.G. ClowerJR., M. Gordon, J. Smith, D. Van Der Veer, and J. A. Bertrand: Formic Acid-Catalysed Rearrangement of Carotol. X-Ray Crystal Structure of the p-Iodobenzoate of One of the Alcohols Formed. J. Chem. Soc. Chem. Commun., 374 (1976).Google Scholar
  89. 75.
    Yamasaki, M.: Total Synthesis of the Sesquiterpene-Daucene. J. Chem. Soc. Commun., 606 (1972).Google Scholar
  90. 76.
    De Broissia, H., J. Levisalles, and H. Rudler: Total Synthesis of the Sesquiterpenes (+)-Daucene, (+)-Carotol, and (-)-Daucol. J. Chem. Soc. Chem. Commun., 855 (1972).Google Scholar
  91. 77.
    Mahmoud, Z.F., N.A. AbdelSalam, T.M. Sarg, and F. Bohlmann: A Carotane Derivative and a Eudesmanolide from Inula crithmoides. Phytochem., 20, 735 (1981).CrossRefGoogle Scholar
  92. 78.
    Ulubelen, A., N. Gören, F. Bohlmann, J. Jakupovic, M. Grenz, and N. Tanker: Sesquiterpene Lactones from Smyrnium cordifolium. Phytochem., 24, 1305 (1985).CrossRefGoogle Scholar
  93. 79.
    Gonzalez, A.G., J.G. Diaz, L.A. Lopez, P.P. De Paz, E. Valencia, and J. Bermejo: Sesquiterpene Alcohol Esters and Sesquiterpene-Coumarin Ethers from Ferula linkiiTF (to be published).Google Scholar
  94. 80.
    Gonzalez, A.G., J.G. Diaz, L.A. Lopez, P.P. De Paz, and J. Bermejo: Distribution of Secondary Metabolites in Ferula from the Canary Islands (to be published).Google Scholar
  95. 81.
    Santos, A.: Vegetación y flora de La Palma. Santa Cruz de Tenerife: Int. Canar. 1983.Google Scholar
  96. 82.
    P. De Paz, P.: Personal communication.Google Scholar
  97. 83.
    Gonzalez, A.G., B.M. Fraga, M.G. Hernandez, J.G. Luis, R. Estevez, J.L. Baez, and M. Rivero: Linkiol, a New Sesquiterpene from Ferula linkii. Phytochem., 16, 265 (1977).CrossRefGoogle Scholar
  98. 84.
    De Broissia, H., J. Levisalles, and H. Rudler: Terpénoides-V, Carotol-IV. Synthèse du (+) Daucène, du (+) Carotol et du (-) Daucol. Bull. Soc. Chim. France, 11, 4314 (1972).Google Scholar
  99. 85.
    Fraga, B.M., M.G. Hernandez, and J.G. Diaz: Carotdiol Esters from Ferula linkii. Phytochem., 28, 1649 (1989).CrossRefGoogle Scholar
  100. 86.
    Levisalles, J., and H. Rudler: Terpénoïdes-II, Carotol-I: Stéréochimie du Carotol. Bull. Soc. Chim. France, 6, 2059 (1967).Google Scholar
  101. 87.
    Appendino, G., M.G. Valle, and P. Gariboldi: Structural and Conformational Studies on Sesquiterpenoid Esters from Laserpitium halleri Crantz subsp. halleri. J. Chem. Soc. Perkin Trans. I, 1363 (1986).Google Scholar
  102. 88.
    Saidkhodzhaev, A.I., and G.R. Nikonov: Esters in Ferula kuhistanica Roots. Khim. Prir. Soedin., 4, 525 (1974)Google Scholar
  103. Saidkhodzhaev, A.I., and G.R. Nikonov: Esters in Ferula kuhistanica Roots. Chem. Abstr., 82, 54180v (1975).Google Scholar
  104. 89.
    Sykora, V., L. Novotny, M. Holub, V. Herout, and F. Sorm: Terpenes, CXVII: The Proof of Structure of Carotol and Daucol. Coll. Czech. Chem. Commun., 26, 788 (1961)Google Scholar
  105. Sykora, V., L. Novotny, M. Holub, V. Herout, and F. Sorm: Terpenes, CXVII: The Proof of Structure of Carotol and Daucol. Coll. Czech. Chem. Abstr., 55, 16588a (1962).Google Scholar
  106. 90.
    Corey, E.J., and G. Schmidt: Useful Procedures for the Oxidation of Alcohols Involving Pyridinium Dichromate in Aprotic Media. Tetrahedron Letters, 399 (1979).Google Scholar
  107. 91.
    Sundararaman, P., and Herz, W.: Oxidative Rearrangements of Tertiary and Some Secondary Allylic Alcohols with Chromium (VI) Reagents. A New Method for 1,3 Functional Group Transposition and Forming Mixed Aldol Products. J. Org. Chem., 42, 813 (1977).CrossRefGoogle Scholar
  108. 92.
    Golovina, L.A., and A.I. Saidkhodzhaev: Structure and Stereochemistry of Lapidin. Khim. Prir. Soedin., 3, 318 (1981)Google Scholar
  109. Golovina, L.A., and A.I. Saidkhodzhaev: Structure and Stereochemistry of Lapidin. Chem. Abstr., 95, 204188p (1981).Google Scholar
  110. 93.
    Gonzalez, A.G.: Personal communication.Google Scholar
  111. 94.
    Sagitdinova, G.V., A.I. Saidkhodzhaev, V.M. Malikov, and S. Melibaev: Esters from Ferula angrenii. Khim. Prir. Soedin., 6, 808 (1978)Google Scholar
  112. Sagitdinova, G.V., A.I. Saidkhodzhaev, V.M. Malikov, and S. Melibaev: Esters from Ferula angrenii. Chem. Abstr., 91, 16666m (1979).Google Scholar
  113. 95.
    Kerimov, S.SH., A.I. Saidkhodzhaev, and V.M. Malikov: Esters of Ferula calcarea. Khim. Prir. Soedin., 5, 765 (1987)Google Scholar
  114. Kerimov, S.SH., A.I. Saidkhodzhaev, and V.M. Malikov: Esters of Ferula calcarea. Chem. Abstr., 108, 91725c (1988).Google Scholar
  115. 96.
    Saidkhodzhaev, A.I., KH.M. Kamilov, and M.G. Pimenov: Esters of Ferula kopetdaghensis. Khim. Prir. Soedin., 5, 764 (1987)Google Scholar
  116. Saidkhodzhaev, A.I., KH.M. Kamilov, and M.G. Pimenov: Esters of Ferula kopetdaghensis. Chem. Abstr., 108, 91724b (1988).Google Scholar
  117. 97.
    Sagitdinova, G.V., A.I. Saidkhodzhaev, G.K. Nikonov, and M. Rakhmankulov: Esters from Ferula lapidosa Roots. Khim. Prir. Soedin., 11, 115 (1975)Google Scholar
  118. Sagitdinova, G.V., A.I. Saidkhodzhaev, G.K. Nikonov, and M. Rakhmankulov: Esters from Ferula lapidosa Roots. Chem. Abstr., 83, 111086r (1975).Google Scholar
  119. 98.
    Khasanov, T.KH., A.I. Saidkhodzhaev, and G.K. Nikonov: Components Of Ferula pallida Roots. Khim. Prir. Soedin., 6, 807 (1972)Google Scholar
  120. Khasanov, T.KH., A.I. Saidkhodzhaev, and G.K. Nikonov: Components Of Ferula pallida Roots. Chem. Abstr., 78, 94809f (1973).Google Scholar
  121. 99.
    Potapov, V.M., and G.K. Nixonov: Chemical Study of Ferula tenuisecta Eug. Izv. Akad. Nauk Kaz. SSR, Ser. Khim., 69 (1980)Google Scholar
  122. Potapov, V.M., and G.K. Nixonov: Chemical Study of Ferula tenuisecta Eug. Izv. Akad. Chem. Abstr., 93, 110550g (1980).Google Scholar
  123. 100.
    Kadyrov, A.SH., T.KH. Khasanov, A.I. Saidkhodzaev, and G.K. Nikonov: New Phenol Compounds of Ferula tschimganica Roots. Khim. Prir. Soedin., 6, 808 (1972)Google Scholar
  124. Kadyrov, A.SH., T.KH. Khasanov, A.I. Saidkhodzaev, and G.K. Nikonov: New Phenol Compounds of Ferula tschimganica Roots. Chem. Abstr., 78, 108207x (1973).Google Scholar
  125. 101.
    Kamilov, KH.M., G.K. Nixonov, and N.N. Sharakhimov: Esters in Ferula fedtschenkoana Roots. Khim. Prir. Soedin., 4, 527 (1974)Google Scholar
  126. Kamilov, KH.M., G.K. Nixonov, and N.N. Sharakhimov: Esters in Ferula fedtschenkoana Roots. Chem. Abstr., 82, 14012k (1975).Google Scholar
  127. 102.
    Saidkhodzhaev, A.I., L.A. Golovina, V.M. Malikov, S. Malibaev, and M. Rakhmankulov: Esters from Three Ferula Species. Khim. Prir. Soedin., 3, 412 (1985)Google Scholar
  128. Saidkhodzhaev, A.I., L.A. Golovina, V.M. Malikov, S. Malibaev, and M. Rakhmankulov: Esters from Three Ferula Species. Chem. Abstr., 103, 51224d (1985).Google Scholar
  129. 103.
    Golovina, L.A., and G.K. Nixonov: Esters of Ferula ceratophylla. Khim. Prir. Soedin., 5, 707 (1977)Google Scholar
  130. Golovina, L.A., and G.K. Nixonov: Esters of Ferula ceratophylla. Chem. Abstr., 88, 85988t (1978).Google Scholar
  131. 104.
    Golovina, L.A., A.I. Saidkhodzhaev, V.M. Malikov, and M.G. Pimenov: Esters of Ferula soonganica and Ferula subtilis. Khim. Prir. Soedin., 5, 763 (1987)Google Scholar
  132. Golovina, L.A., A.I. Saidkhodzhaev, V.M. Malikov, and M.G. Pimenov: Esters of Ferula soonganica and Ferula subtilis. Chem. Abstr., 108, 91723a (1988).Google Scholar
  133. 105.
    Sagitdinova, G.V., A.I. Saidkhodzhaev, V.M. Malikov: Components of Ferula tschatcalensis Roots. Khim. Prir. Soedin., 6, 721 (1983)Google Scholar
  134. Sagitdinova, G.V., A.I. Saidkhodzhaev, V.M. Malikov: Components of Ferula tschatcalensis Roots. Chem. Abstr., 100, 171546v (1984).Google Scholar
  135. 106.
    Makhmudov, M.K., B. Tashkhodzhaev, G.V. Sagitdinova, and A.I. Saidkhodzhaev: X-Ray Analysis of Sesquiterpene Esters from Plants of the Genus Ferula, II: Crystalline and Molecular Structures of the Humulan Alcohol Fekserol. Khim. Prir. Soedin., 1, 42 (1986)Google Scholar
  136. Makhmudov, M.K., B. Tashkhodzhaev, G.V. Sagitdinova, and A.I. Saidkhodzhaev: X-Ray Analysis of Sesquiterpene Esters from Plants of the Genus Ferula, II: Crystalline and Molecular Structures of the Humulan Alcohol Fekserol. Chem. Abstr., 105, 24111z (1986).Google Scholar
  137. 107.
    Saidkhodzhaev, A.I., G.V. Sagitdinova, L.A. Golovina, and A.SH. Kadyrov: Structure of Novel Esters from the Ferula Genus of Plants. Tezisy Dokl. Sov. Indiiskii Simp. Khim. Prir. Soedin., 5, 80 (1978)Google Scholar
  138. Saidkhodzhaev, A.I., G.V. Sagitdinova, L.A. Golovina, and A.SH. Kadyrov: Structure of Novel Esters from the Ferula Genus of Plants. Tezisy Dokl. Sov. Indiiskii Simp. Chem. Abstr., 93, 146293q (1980).Google Scholar
  139. 108.
    Sagitdinova, G.V., A.I. Saidkhodzhaev, and G.K. Nikonov: Phenolic Components of Ferula juniperina. Khim. Prir. Soedin., 4, 547 (1976)Google Scholar
  140. Sagitdinova, G.V., A.I. Saidkhodzhaev, and G.K. Nikonov: Phenolic Components of Ferula juniperina. Chem. Abstr., 85, 189198q (1976).Google Scholar
  141. 109.
    Saidkhodzhaev, A.I., N.D. Abdullaev, T.KH. Khasanov, G.K. Nikonov, and M.R. Yagudaev: Structure of Angrendiol, Ferolin, and Tschimganidin. Khim. Prir. Soedin., 4, 519 (1977)Google Scholar
  142. Saidkhodzhaev, A.I., N.D. Abdullaev, T.KH. Khasanov, G.K. Nikonov, and M.R. Yagudaev: Structure of Angrendiol, Ferolin, and Tschimganidin. Chem. Abstr., 88, 3049a (1978).Google Scholar
  143. 110.
    Kadyrov, A.SH., A.I. Saidkhodzhaev, and G.K. Nikonov: Structure of Fecorine, a New Ester from Ferula korshinskyi Roots. Khim. Prir. Soedin., 11 (2), 152 (1975)Google Scholar
  144. Kadyrov, A.SH., A.I. Saidkhodzhaev, and G.K. Nikonov: Structure of Fecorine, a New Ester from Ferula korshinskyi Roots. Chem. Abstr., 83, 111106x (1975).Google Scholar
  145. 111.
    Potapov, V.M., KH.M. Kamilov, and G.K. Nikonov: Phytochemistry Study of Ferula involucrata. Nek. Probl. Farm. Nauki Prakt., Mater. S’ezda Farm. Kas., 1, 112 (1975)Google Scholar
  146. Potapov, V.M., KH.M. Kamilov, and G.K. Nikonov: Phytochemistry Study of Ferula involucrata. Nek. Probl. Farm. Nauki Prakt., Mater. hem. Abstr., 87, 2357s (1977).Google Scholar
  147. 112.
    Potapov, V.M., and G.K. Nikonov: Esters of Ferula leucographa and Ferula ugamica. Izv. Akad. Nauk Kaz. SSR, Ser. Khim., 64 (1981)Google Scholar
  148. Potapov, V.M., and G.K. Nikonov: Esters of Ferula leucographa and Ferula ugamica. Izv. Akad. Chem. Abstr., 95, 21286z (1981).Google Scholar
  149. 113.
    Bagirov, V.Yu., R.Yu. Gasanova, F.A. Rasulov, and M.G. Pimenov: Ester from Ferula leucographa. Khim. Prir. Soedin., 3, 422 (1980)Google Scholar
  150. Bagirov, V.Yu., R.Yu. Gasanova, F.A. Rasulov, and M.G. Pimenov: Ester from Ferula leucographa. Chem. Abstr., 93, 164328j (1980).Google Scholar
  151. 114.
    Sagitdinova, G.V., A.I. Saidkhodzhaev, and V.M. Malikov: Structure of Fertenin. Khim. Prir. Soedin., 2, 161 (1979)Google Scholar
  152. Sagitdinova, G.V., A.I. Saidkhodzhaev, and V.M. Malikov: Structure of Fertenin. Chem. Abstr., 92, 6723j (1980).Google Scholar
  153. 115.
    Potapov, V.M., and G.K. Nlxoxov: Esters of Ferula tenuisecta. Eug. Kor. from the Aksu-Dzhabagli Wildlife Refuge. Izv. Akad. Nauk Kaz. SSR, Ser. Khim., 2, 63 (1980)Google Scholar
  154. Potapov, V.M., and G.K. Nlxoxov: Esters of Ferula tenuisecta. Eug. Kor. from the Aksu-Dzhabagli Wildlife Refuge. Izv. Akad. Chem. Abstr., 93, 110549p (1980).Google Scholar
  155. 116.
    Bizhanova, K., A.I. Saidkhodzhaev, and V.M. Malikov: Fecseridin and Fecserinin-New Esters from Ferula xeromorpha. Khim. Prir. Soedin., 5, 576 (1978)Google Scholar
  156. Bizhanova, K., A.I. Saidkhodzhaev, and V.M. Malikov: Fecseridin and Fecserinin-New Esters from Ferula xeromorpha. Chem. Abstr., 90, 83600c (1979).Google Scholar
  157. 117.
    Bizhanova, K., A.I. Saidkhodzhaev, and V.M. Malikov: Structure of Fekserine. Khim. Prir. Soedin., 3, 407 (1978)Google Scholar
  158. Bizhanova, K., A.I. Saidkhodzhaev, and V.M. Malikov: Structure of Fekserine. Chem. Abstr., 89, 147091b (1978).Google Scholar
  159. 118.
    Kadyrov, A., A.I. Saidkhodzhaev, and G.K. Nlxoxov: Structure of Akitschenol and Akitschenin. Khim. Prir. Soedin., 1, 102 (1976)Google Scholar
  160. Kadyrov, A., A.I. Saidkhodzhaev, and G.K. Nlxoxov: Structure of Akitschenol and Akitschenin. Chem. Abstr., 85, 59565w (1976).Google Scholar
  161. 119.
    Saidkhodzhaev, A.I., D. Batsuren, and V.M. Malikov: Esters from Ferula akitschensis. Khim. Prir. Soedin., 5, 709 (1985)Google Scholar
  162. Saidkhodzhaev, A.I., D. Batsuren, and V.M. Malikov: Esters from Ferula akitschensis. Chem. Abstr., 104, 85436k (1986).Google Scholar
  163. 120.
    Saidkhodzhaev, A.I., and G.K. Nikonov: Components of Ferula ovina Roots. Khim. Prir. Soedin., 4, 526 (1974)Google Scholar
  164. Saidkhodzhaev, A.I., and G.K. Nikonov: Components of Ferula ovina Roots. Chem. Abstr., 82, 14011j (1975).Google Scholar
  165. 121.
    Potapov, V.M., and G.K. Nikonov: Esters of Ferula pallida Roots. Khim. Prir. Soedin., 6, 819 (1976)Google Scholar
  166. Potapov, V.M., and G.K. Nikonov: Esters of Ferula pallida Roots. Chem. Abstr., 86, 136306n (1977).Google Scholar
  167. 122.
    Ahmed, A.A.: New Sesquiterpenes from Ferula sinaica. J. Nat. Prod., 53, 483 (1990).CrossRefGoogle Scholar
  168. 123.
    Eidler, YA.I., G.L. Genikina, and T.T. Shakirov: Chromatospectrophotomeric Method for Determination of Ferutinin, Teferin and Ferutin. Khim. Prir. Soedin., 5, 616 (1976)Google Scholar
  169. Eidler, YA.I., G.L. Genikina, and T.T. Shakirov: Chromatospectrophotomeric Method for Determination of Ferutinin, Teferin and Ferutin. Chem. Abstr., 86, 85646p (1977).Google Scholar
  170. 124.
    Melibaev, S., U. Rakhmankulov, and A.I. Saidkhodzhaev: IntraSpeCieS Chemical Variability in Ferula tenuisecta. Korov. Rastit. Resur., 431 (1980)Google Scholar
  171. Melibaev, S., U. Rakhmankulov, and A.I. Saidkhodzhaev: IntraSpeCieS Chemical Variability in Ferula tenuisecta. Chem. Abstr., 93, 182807u (1980).Google Scholar
  172. 125.
    Kazdan, T.K., B. Qadri, M.A. Qurishi, M.A. Khuroo, and P.K. Kachroo: Sesquiterpene Esters and Sesquiterpene-Coumarin Ethers from Ferula jaeschkeana. Phytochem., 28, 3389 (1989).CrossRefGoogle Scholar
  173. 126.
    Garg, S.N., L.N. Misra, S.K. Agarwal, V.P. Mahajan, and S.N. Rastogi: Carotane Derivatives from Ferula jaeschkeana. Phytochem., 25, 449 (1987).CrossRefGoogle Scholar
  174. 127.
    Singh, M.M., A. Agnihotri, S.N. Garg, S.K. Agarwal, D.N. Gupta, G. Keshri, and V.P. Kamboj: Antifertility and Hormonal Properties of Certain Carotane Sesquiterpenes of Ferula jaeschkeana. Planta Med., 54 (6), 492 (1988).CrossRefGoogle Scholar
  175. 128.
    Kadyrov, A.SH., A.I. Saidkhodzhaev, G.K. Nikonov, and U.R. Kulov: Esters of Ferula akitschensis. Khim. Prir. Soedin., 2, 284 (1977)Google Scholar
  176. Kadyrov, A.SH., A.I. Saidkhodzhaev, G.K. Nikonov, and U.R. Kulov: Esters of Ferula akitschensis. hem. Abstr., 87, 98862b (1977).Google Scholar
  177. 129.
    Kadyrov, A.SH., and A.I. Saidkhodzhaev: Structure of Akiferinin. Khim. Prir. Soedin., 1, 137 (1978)Google Scholar
  178. Kadyrov, A.SH., and A.I. Saidkhodzhaev: Structure of Akiferinin.Chem. Abstr., 88, 191130s (1978).Google Scholar
  179. 130.
    Saidkhodzhaev, A.I.: Structure of Tenuferin, Tenuferinin and Tenuferidin. Khim. Prir. Soedin., 1, 70 (1978)Google Scholar
  180. Saidkhodzhaev, A.I.: Structure of Tenuferin, Tenuferinin and Tenuferidin. Chem. Abstr., 89, 6437g (1978).Google Scholar
  181. 131.
    Watson, W.H., R.P. Kashyap, and I. Tavanaiepour: rel-(3R,3aR,8S,8aR)-3ahydroxyl-1-oxo-6-daucen-8-yl p-anisate(1) and rel-(1S,3R,3aS,4S,8S,8aR)-1,8-diacetoxy-3-hydroxy-6-daucen-4-yl p-anisate(2). Acta Crystallogr., Sect. C: Cryst. Struct. Commun., 1050 (1985)Google Scholar
  182. Watson, W.H., R.P. Kashyap, and I. Tavanaiepour: rel-(3R,3aR,8S,8aR)-3ahydroxyl-1-oxo-6-daucen-8-yl p-anisate(1) and rel-(1S,3R,3aS,4S,8S,8aR)-1,8-diacetoxy-3-hydroxy-6-daucen-4-yl p-anisate(2). Acta Crystallogr., Sect. C: Chem. Abstr., 104, 6038j (1986).Google Scholar
  183. 132.
    Valle, M.G., A. Giovanni, N.M. Gian, and P. Vicenzo: Prenylated Coumarins and Sesquiterpenoids from Ferula communis. Phytochem., 26, 253 (1987).CrossRefGoogle Scholar
  184. 133.
    Saidkhodzhaev, A.I., and G. Nlxoxov: Structure of Teferidine, a New Ester from Ferula tenuisecta Fruit. Khim. Prir. Soedin., 1, 105 (1976)Google Scholar
  185. Saidkhodzhaev, A.I., and G. Nlxoxov: Structure of Teferidine, a New Ester from Ferula tenuisecta Fruit. hem. Abstr., 85, 59567y (1976).Google Scholar
  186. 134.
    Miski, M., and J. Jakupovic: Daucane Esters from Ferula rigidula. Phytochem., 29, 173 (1990).CrossRefGoogle Scholar
  187. 135.
    Saidkhodzhaev, A.I., and G.K. Nikonov: Esters in Ferula kuhistanica Roots. Khim. Prir. Soedin., 4, 525 (1974)Google Scholar
  188. Saidkhodzhaev, A.I., and G.K. Nikonov: Esters in Ferula kuhistanica Roots. Chem. Abstr., 82, 54180v (1975).Google Scholar
  189. 136.
    Khasanov, T.KH., A.I. Saidkhodzhaev, and G.K. Nikonov: Structure of Teferin, a New Ester from Ferula tenuisecta Root. Khim. Prir. Soedin., 4, 528 (1974)Google Scholar
  190. Khasanov, T.KH., A.I. Saidkhodzhaev, and G.K. Nikonov: Structure of Teferin, a New Ester from Ferula tenuisecta Root. Chem. Abstr., 82, 82954u (1975).Google Scholar
  191. 137.
    Golovina, L.A., A.I. Saidkhodzhaev, V.M. Malikov, and S. Melibaev: Structure of Lapidolin and Lapidolidin. Khim. Prir. Soedin., 6, 787 (1982)Google Scholar
  192. Golovina, L.A., A.I. Saidkhodzhaev, V.M. Malikov, and S. Melibaev: Structure of Lapidolin and Lapidolidin. Chem. Abstr., 98, 143673f (1983).Google Scholar
  193. 138.
    Tashkhodzhaev, B., M.K. Makhmudov, L.A. Golovina, A.I. Saidkhodzhaev, and M.R. Yagudaev: X-Ray Structure Characteristics of Sesquiterpene Esters from Ferula Plants, I: Crystal and Molecular Structure of the Lapidoline Carotane Ester. Khim. Prir. Soedin., 3 309 (1984)Google Scholar
  194. Tashkhodzhaev, B., M.K. Makhmudov, L.A. Golovina, A.I. Saidkhodzhaev, and M.R. Yagudaev: X-Ray Structure Characteristics of Sesquiterpene Esters from Ferula Plants, I: Crystal and Molecular Structure of the Lapidoline Carotane Ester. Chem. Abstr., 102 59336s (1985).Google Scholar
  195. 139.
    Golovina, L.A., A.I. Saidkhodzhaev, and V.M. Malikov: Structure and Stereo-chemistry of Lapiferinin. Khim. Prir. Soedin., 3, 301 (1983)Google Scholar
  196. Golovina, L.A., A.I. Saidkhodzhaev, and V.M. Malikov: Structure and Stereo-chemistry of Lapiferinin. Chem. Abstr., 99, 102267d (1983).Google Scholar
  197. 140.
    Golovina, L.A., A.I. Saidkhodzhaev, and V.M. Malikov: Structure of Lapidolidin. Khim. Prir. Soedin., 5, 713 (1985)Google Scholar
  198. Golovina, L.A., A.I. Saidkhodzhaev, and V.M. Malikov: Structure of Lapidolidin. Chem. Abstr., 104, 126521e (1986).Google Scholar
  199. 141.
    Golovina, L.A., A.I. Saidkhodzhaev, N.D. Abdullaev, V.M. Malikov, and M.R. Yagudaev: Structure and Stereochemistry of Lapiferin. Khim. Prir. Soedin., 3, 296 (1983)Google Scholar
  200. Golovina, L.A., A.I. Saidkhodzhaev, N.D. Abdullaev, V.M. Malikov, and M.R. Yagudaev: Structure and Stereochemistry of Lapiferin. Chem. Abstr., 99, 102266c (1983).Google Scholar
  201. 142.
    Golovina, L.A., T.KH. Khasanov, A.I. Saidkhodzhaev, V.M. Malikov, and U. Rakhmankulov: Coumarins am. Esters from Ferula microcarpa. Khim. Prir. Soedin., 5, 566 (1978)Google Scholar
  202. Golovina, L.A., T.KH. Khasanov, A.I. Saidkhodzhaev, V.M. Malikov, and U. Rakhmankulov: Coumarins am. Esters from Ferula microcarpa. Chem. Abstr., 90, 83598h (1979).Google Scholar
  203. 143.
    Kushmuradov, A.Yu., M.K. Makhmudov, A.I. Saidkhodzhaev, B. Tashkhodzhaev, V.M. Malikov, and M.R. Yagudaev: X-Ray Structural Analysis of Sesquiterpene Esters from Plants of the Genus Ferula, IV: Structure and Stereochemistry of the New Carotane Ester Pallidin. Khim. Prir. Soedin., 1, 42 (1990)Google Scholar
  204. Kushmuradov, A.Yu., M.K. Makhmudov, A.I. Saidkhodzhaev, B. Tashkhodzhaev, V.M. Malikov, and M.R. Yagudaev: X-Ray Structural Analysis of Sesquiterpene Esters from Plants of the Genus Ferula, IV: Structure and Stereochemistry of the New Carotane Ester Pallidin. Chem. Abstr., 113, 55865t (1990).Google Scholar
  205. 144.
    Kushmuradov, A.Yu., A.I. Saidkhodzhaev, and ASH. Kadyrov: Structure of Palliferidin from Ferula pallida. Khim. Prir. Soedin., 3, 400 (1981)Google Scholar
  206. Kushmuradov, A.Yu., A.I. Saidkhodzhaev, and ASH. Kadyrov: Structure of Palliferidin from Ferula pallida. Chem. Abstr., 95, 204189q (1981).Google Scholar
  207. 145.
    Kushmuradov, A.Yu., A.I. Saidkhodzhaev, and A.SH. Kadyrov: Structure and Stereochemistry of Palliferidin and Palliferinin. Khim. Prir. Soedin., 4, 523 (1981)Google Scholar
  208. Kushmuradov, A.Yu., A.I. Saidkhodzhaev, and A.SH. Kadyrov: Structure and Stereochemistry of Palliferidin and Palliferinin. Chem. Abstr., 96, 52525b (1982).Google Scholar
  209. 146.
    Kushmuradov, A.Yu., A.I. Saidkhodzhaev, and V.M. Malikov: Structure and Stereochemistry of Pallinin. Khim. Prir. Soedin., 1, 53 (1986)Google Scholar
  210. Kushmuradov, A.Yu., A.I. Saidkhodzhaev, and V.M. Malikov: Structure and Stereochemistry of Pallinin. Chem. Abstr., 105, 75874h (1986).Google Scholar
  211. 147.
    Alhazimi, H.M.G.: Terpenoids and Coumarins from Ferula sinaica. Phytochem., 10, 2417 (1986).CrossRefGoogle Scholar
  212. 148.
    Makhmudov, M.K., L.A. Golovina, B. Tashkodzhaev, A.I. Saidkhodzhaev, M.R. Yagudaev, and V.M. Malikov: X-Ray Structure Investigation of Sesquiterpene Esters from Plants of the Genus Ferula. Khim. Prir. Soedin., 1, 68 (1989)Google Scholar
  213. Makhmudov, M.K., L.A. Golovina, B. Tashkodzhaev, A.I. Saidkhodzhaev, M.R. Yagudaev, and V.M. Malikov: X-Ray Structure Investigation of Sesquiterpene Esters from Plants of the Genus Ferula. Chem. Abstr., 111, 74798y (1989).Google Scholar
  214. 149.
    Kushmuradov, A.Yu., A.SH. Kadyrov, A.I. Saidkhodzhaev, and V.M. Malikov: Structure of Akiferidin and Akiferidinin. Khim. Prir. Soedin., 6, 725 (1978)Google Scholar
  215. Kushmuradov, A.Yu., A.SH. Kadyrov, A.I. Saidkhodzhaev, and V.M. Malikov: Structure of Akiferidin and Akiferidinin. Chem. Abstr., 90, 200272k (1979).Google Scholar
  216. 150.
    Rajendra, K., S.K. Paknikar, G.K. Trivedi, and S.C. Bhattacharyya: Structure of Vaginatin, A Polyoxygenated Sesquiterpenoid Isolated from Selinum vaginatum. Ind. J. Chem., 16B, 4 (1978).Google Scholar
  217. 151.
    Nabiev, A.A., T.KH. Khasanov, and V.M. Malikov: New Terpenoid Coumarins from Ferula kopetdaghensis. Khim. Prir. Soedin., 4, 516 (1978)Google Scholar
  218. Nabiev, A.A., T.KH. Khasanov, and V.M. Malikov: New Terpenoid Coumarins from Ferula kopetdaghensis.Chem. Abstr., 89, 193845y (1978).Google Scholar
  219. 152.
    Kamilov, KH.M., and G.K. Nikonov: Coumarins of Ferula kopetdaghensis, Kopetdaghin and Farnesiferol B (Copeodin). Khim. Prir. Soedin., 4, 442 (1974)Google Scholar
  220. Kamilov, KH.M., and G.K. Nikonov: Coumarins of Ferula kopetdaghensis, Kopetdaghin and Farnesiferol B (Copeodin). Chem. Abstr., 82, 70266h (1974).Google Scholar
  221. 153.
    Kamilov, KH.M., and G.K. Nikonov: Coumarins of Ferula kopetdaghensis and Structure of Kopedine and Kopeoside. Khim. Prir. Soedin., 3, 308 (1973)Google Scholar
  222. Kamilov, KH.M., and G.K. Nikonov: Coumarins of Ferula kopetdaghensis and Structure of Kopedine and Kopeoside. Chem. Abstr., 79, 134321v (1973).Google Scholar
  223. 154.
    Veselovskaya, N.V., Yu.E. Sklyar, D.A. Fesenko, and M.G. Pimenov: Fekrol, A Terpenoid Coumarin from Ferula krylovii. Khim. Prir. Soedin., 6, 851 (1979)Google Scholar
  224. Veselovskaya, N.V., Yu.E. Sklyar, D.A. Fesenko, and M.G. Pimenov: Fekrol, A Terpenoid Coumarin from Ferula krylovii. Chem. Abstr., 93, 41500b (1980).Google Scholar
  225. 155.
    Khasanov, T.KH., A.I. Saidkhodzhaev, and G.K. Nikonov: Structure of Feropolin, Feropolol, Feropolon and Feropolidin. Khim. Prir. Soedin., 1, 91 (1976)Google Scholar
  226. Khasanov, T.KH., A.I. Saidkhodzhaev, and G.K. Nikonov: Structure of Feropolin, Feropolol, Feropolon and Feropolidin. Chem. Abstr., 85, 59558w (1976).Google Scholar
  227. 156.
    Saidkhodzhaev, A.I., and V.M. Malikov: Stereochemistry of Feropolol, Feropolin, Feropolone and Feropolidin. Khim. Prir. Soedin., 6, 799 (1978)Google Scholar
  228. Saidkhodzhaev, A.I., and V.M. Malikov: Stereochemistry of Feropolol, Feropolin, Feropolone and Feropolidin. Chem. Abstr., 90, 200277r (1979).Google Scholar
  229. 157.
    Nabiev, A.A., T.KH. Khasanov, and V.M. Malikov: New Terpenoid Coumarin from Ferula kopetdaghensis. Khim. Prir. Soedin., 1, 48 (1982)Google Scholar
  230. Nabiev, A.A., T.KH. Khasanov, and V.M. Malikov: New Terpenoid Coumarin from Ferula kopetdaghensis. Chem. Abstr., 96, 214275z (1982).Google Scholar
  231. 158.
    Kadyrov, A.SH., A.I. Saidkhodzhaev, and V.M. Malikov: Structure of Foliferin. Khim. Prir. Soedin., 4, 518 (1978)Google Scholar
  232. Kadyrov, A.SH., A.I. Saidkhodzhaev, and V.M. Malikov: Structure of Foliferin. Chem. Abstr., 90, 69072a (1979).Google Scholar
  233. 159.
    Banerji, A., B. Mallick, and A. Chatterjee: Assafoetidin and Ferocolicin, Two Sesquiterpenoid Coumarins from Ferula assafoetida Regel. Tetrahedron Letters, 29, 1557 (1988).CrossRefGoogle Scholar
  234. 160.
    Kajimoto, T., K. Yahiro, and T. Nohara: Sesquiterpenoid and Disulphide Derivatives from Ferula assafoetida. Phytochem., 28, 1761 (1989).CrossRefGoogle Scholar
  235. 161.
    Serkerov, S.V.: Structure of Ferulin. Khim. Prir. Soedin., 6, 371 (1970)Google Scholar
  236. Serkerov, S.V.: Structure of Ferulin. Chem. Abstr., 73, 88041e (1970).Google Scholar
  237. 162.
    Serkerov, S.V.: Ferulin, Sesquiterpene Lactone from Ferula oopoda Roots. Khim. Prir. Soedin., 6, 134 (1970)Google Scholar
  238. Serkerov, S.V.: Ferulin, Sesquiterpene Lactone from Ferula oopoda Roots. Chem. Abstr., 73, 73111d (1970).Google Scholar
  239. 163.
    Serkerov, S.V.: Structure of Ferulidin, A New Sesquiterpenoid Lactone. Khim Prir. Soedin., 6, 428 (1970)Google Scholar
  240. Serkerov, S.V.: Structure of Ferulidin, A New Sesquiterpenoid Lactone. Chem. Abstr., 74, 17861g (1971).Google Scholar
  241. 164.
    Savina, A.A., D.A. Fesenko, L.I. Dukhovlinova, Yu.E. Sklyar, M.G. Pimenov, and Yu.V. Baranova: Lactones of Ferula gigantea. Khim. Prir. Soedin., 4, 490 (1979)Google Scholar
  242. Savina, A.A., D.A. Fesenko, L.I. Dukhovlinova, Yu.E. Sklyar, M.G. Pimenov, and Yu.V. Baranova: Lactones of Ferula gigantea. Chem. Abstr., 92, 111177g (1980).Google Scholar
  243. 165.
    Rychlewska, U., D.J. Hodson, M. Holub, M. Budesinsky, and Z. Smitalova: The Structure of 2-Oxo-8a-angeloyloxy-11a-acetoxy-53H,6aH,7aH-guai-1(10),3-dien6,12-olide, A Sesquiterpenic Lactone from Laserpitium prutenicum L. Revision of the Stereostructures of Native 2-Oxoguai-1(10),3-dien-6,12-olides from the Species of the Umbelliferae Family. Coll. Czech. Comm., 50, 2607 (1985).CrossRefGoogle Scholar
  244. 166.
    Bagirov, V.Yu., V.I. Sheichenko, N.F. Mirbabaev, and M. Pimenov: Sesquiterpene Lactones of Ferula litvinowiana. Khim. Prir. Soedin., 1, 114 (1984)Google Scholar
  245. Bagirov, V.Yu., V.I. Sheichenko, N.F. Mirbabaev, and M. Pimenov: Sesquiterpene Lactones of Ferula litvinowiana. Chem. Abstr., 100, 188795y (1984).Google Scholar
  246. 167.
    Bagirov, V.Yu., V.I. Sheichenko, R.Yu. Gasanova, and M.G. Pimenov: Study of Ferula malacophylla Lactones. Khim. Prir. Soedin., 4, 445 (1978)Google Scholar
  247. Bagirov, V.Yu., V.I. Sheichenko, R.Yu. Gasanova, and M.G. Pimenov: Study of Ferula malacophylla Lactones.Chem. Abstr., 89, 211929k (1978).Google Scholar
  248. 168.
    Konovalova, O.A., K.S. Rybalko, and V.I. Sheichenko: Sesquiterpene Lactones of Ferula olgae. Khim. Prir. Soedin., 5, 590 (1975)Google Scholar
  249. Konovalova, O.A., K.S. Rybalko, and V.I. Sheichenko: Sesquiterpene Lactones of Ferula olgae. Khim. Chem. Abstr., 84, 105802a (1976).Google Scholar
  250. 169.
    Savina, A.A., L.I. Dukhovlinova, Yu.E. Sklyar, D.A. Fesenko, and M.G. Pimenov: Fegnolide A Lactone from Ferula gigantea Roots. Khim. Prir. Soedin., 5, 733 (1979)Google Scholar
  251. Savina, A.A., L.I. Dukhovlinova, Yu.E. Sklyar, D.A. Fesenko, and M.G. Pimenov: Fegnolide A Lactone from Ferula gigantea Roots. Chem. Abstr. 94, 61703u (1981).Google Scholar
  252. 170.
    Bagirov, V.YU., V.I. Sheichenko, I.K. Abdullaeva, and M.G. Pimenov: SesquiteIpene Lactones of Ferula varia. Khim. Prir. Soedin., 6, 843 (1980)Google Scholar
  253. Bagirov, V.YU., V.I. Sheichenko, I.K. Abdullaeva, and M.G. Pimenov: SesquiteIpene Lactones of Ferula varia. Chem. Abstr., 94, 171054r (1981).Google Scholar
  254. 171.
    Bagirov, V.YU., V.I. Sheichenko, R.Yu. Gasanova, and M.G. Pimenov: Sesquiterpene Lactone from Ferula malacophylla Seeds. Khim. Prir. Soedin., 6, 810 (1978)Google Scholar
  255. Bagirov, V.YU., V.I. Sheichenko, R.Yu. Gasanova, and M.G. Pimenov: Sesquiterpene Lactone from Ferula malacophylla Seeds. Chem. Abstr., 91, 25021 (1979).Google Scholar
  256. 172.
    Kiseleva, V.V., A.I. Saidkhodzhaev, and G.K. Nikonov: Sesquiterpene Lactones from the Roots of Ferula diversivittata. Khim. Prir. Soedin., 1, 126 (1975)Google Scholar
  257. Kiseleva, V.V., A.I. Saidkhodzhaev, and G.K. Nikonov: Sesquiterpene Lactones from the Roots of Ferula diversivittata. Chem. Abstr., 84, 5166c (1976).Google Scholar
  258. 173.
    Serkerov, S.V., and V.V. Kiseleva: Structure of Diversolide. Khim. Prir. Soedin., 4, 525 (1982)Google Scholar
  259. Serkerov, S.V., and V.V. Kiseleva: Structure of Diversolide. Chem. Abstr., 98, 125719w (1983).Google Scholar
  260. 174.
    Nurmukhamedova, R.M., SH.Z. Kasymov, and S. Malibaev: Grilactone from Ferula penninervis. Khim. Prir. Soedin., 2, 261 (1982)Google Scholar
  261. Nurmukhamedova, R.M., SH.Z. Kasymov, and S. Malibaev: Grilactone from Ferula penninervis. Khim. Chem. Abstr., 97, 107075h (1982).Google Scholar
  262. 175.
    Malone, F.J., M. Parves, A. Karin, A.M. Mckervey, I. Ahmad, and K.M. Bhatty: Isolation and Crystal Structure of Grilactone, A New Guaianolide from Ferula oopoda. J. Chem. Soc. Perkin Trans. 2, 11, 1683 (1980).Google Scholar
  263. 176.
    Kir’yalov, N.P., and S.V. Serkerov: Guaianolides from Plants of the Umbelliferae Family. Mezhdumar. Kongr. Efirnym. Maslam. [Mater] (pub. 1971 ), 1, 147 (1968)Google Scholar
  264. Kir’yalov, N.P., and S.V. Serkerov: Guaianolides from Plants of the Umbelliferae Family. Mezhdumar. Kongr. Efirnym. Maslam. Chem. Abstr., 78, 159896d (1973).Google Scholar
  265. 177.
    Bagirov, V.YU., V.I. Sheichenko, R.Yu. Gasanova, and M.G. Pimenov: SeSquiterpene Lactone from Ferula malacophylla. Khim. Prir. Soedin., 6, 811 (1978)Google Scholar
  266. Bagirov, V.YU., V.I. Sheichenko, R.Yu. Gasanova, and M.G. Pimenov: SeSquiterpene Lactone from Ferula malacophylla. Khim. Chem. Abstr., 91, 2503u (1979)Google Scholar
  267. 178.
    Nurmukhamedova, M.R., SH.Z. Kasymov, and G.P. Sidyakin: Ferolide, A New Lactone from Ferula penninervis. Khim. Prir. Soedin., 4, 533 (1983)Google Scholar
  268. Nurmukhamedova, M.R., SH.Z. Kasymov, and G.P. Sidyakin: Ferolide, A New Lactone from Ferula penninervis. Chem. Abstr., 100, 3491e (1984).Google Scholar
  269. 179.
    Nurmukhamedova, M.R., SH.Z. Kasymov, N.D. Abdullaev, and G.P. Sidyakin: Structure of Fegurolide. Khim. Prir. Soedin., 3, 335 (1985)Google Scholar
  270. Nurmukhamedova, M.R., SH.Z. Kasymov, N.D. Abdullaev, and G.P. Sidyakin: Structure of Fegurolide. Khim. Chem. Abstr., 103, 85070r (1985).Google Scholar
  271. 180.
    Casinovi, C.G., L. Tomassini, and M. Nicoletti: A New Guaianolide from Ferula arrigonii Bocchieri. Gass. Chim. Ital., 11, 563 (1989)Google Scholar
  272. Casinovi, C.G., L. Tomassini, and M. Nicoletti: A New Guaianolide from Ferula arrigonii Bocchieri. Gass. Chem. Abstr., 112, 175650v (1990).Google Scholar
  273. 181.
    Serkerov, S.V.: Stereochemistry of Guaianolide from Ferula oopoda. Chem. Abstr., 94, 117786t (1981).Google Scholar
  274. Serkerov, S.V.: Stereochemistry of Guaianolide from Ferula oopoda. Chem. Abstr., 94, 117786t (1981).Google Scholar
  275. 182.
    Serkerov, S.V.: Stereochemistry of Ferula oopoda Eudesmanolides. Chem. Abstr., 94, 65869a (1981).Google Scholar
  276. Serkerov, S.V.: Stereochemistry of Ferula oopoda Eudesmanolides. Chem. Abstr., 94, 65869a (1981).Google Scholar
  277. 183.
    Holub, M., M. Budesinsky, Z. Smitlova, D. Saman, and U. Rychlewska: Structure of Isosilerolide, Relative and Absolute Configuration of Silerolide and Larolide Sesquiterpenic Lactones of New Stereoisomeric Type of Eudesmanolides. Coll. Czech. Chem. Comm., 51, 903 (1986).CrossRefGoogle Scholar
  278. 184.
    Serkerov, S.V.: Lactone Sesquiterpene of Ferula badkhysi. Khim. Prir. Soedin., 3, 393 (1976)Google Scholar
  279. Serkerov, S.V.: Lactone Sesquiterpene of Ferula badkhysi. Khim. Chem. Abstr., 85, 139718p (1976).Google Scholar
  280. 185.
    Serkerov, S.V.: New Sesquiterpene Hydroxylactone from Ferula oopoda. Khim. Prir. Soedin., 6, 838 (1971)Google Scholar
  281. Serkerov, S.V.: New Sesquiterpene Hydroxylactone from Ferula oopoda. Chem. Abstr., 76, 151049t (1972).Google Scholar
  282. 186.
    Serkerov, S.V.: Sesquiterpene Lactone, Semopodin, from Ferula oopoda Seeds. Khim. Prir. Soedin., 4, 241 (1969)Google Scholar
  283. Serkerov, S.V.: Sesquiterpene Lactone, Semopodin, from Ferula oopoda Seeds. Khim. Chem. Abstr., 72, 63626r (1970).Google Scholar
  284. 187.
    Serkerov, S.V.: Stereochemistry of Ferula oopoda. Khim. Prir. Soedin., 16, 629 (1980)Google Scholar
  285. Serkerov, S.V.: Stereochemistry of Ferula oopoda. Chem. Abstr., 94, 117786t (1981).Google Scholar
  286. 188.
    Sagitdinova, G.V., A.I. Saidkhodzhaev, V.M. Malikov, M.G. Pimenov, and S. Melibaev: Sesquiterpene Lactones of Ferula clematidifolia and Lipularia alpina. Khim. Prir. Soedin., 26, 553 (1990)Google Scholar
  287. Sagitdinova, G.V., A.I. Saidkhodzhaev, V.M. Malikov, M.G. Pimenov, and S. Melibaev: Sesquiterpene Lactones of Ferula clematidifolia and Lipularia alpina. Khim. Chem. Abstr., 114, 98274n (1991).Google Scholar
  288. 189.
    Savina, A.A., D. Ovlinova, Yu.E. Sklyar, D.A. Fesenko, and M.G. Pimenov: A Lactone from the Roots of Ferula gigantea. Khim. Prir. Soedin., 15, 733 (1980)Google Scholar
  289. Savina, A.A., D. Ovlinova, Yu.E. Sklyar, D.A. Fesenko, and M.G. Pimenov: A Lactone from the Roots of Ferula gigantea. Khim. Chem. Abstr., 94, 61703u (1981).Google Scholar
  290. 190.
    Tashkhodzhaev, B., M.K. Makhmudov, M.R. Normukhamedova, and S.A. Talipov: Crystal and Molecular Structure of the Sesquiterpene Lactone Ferulide. Khim. Prir. Soedin., 24, 55 (1988)Google Scholar
  291. Tashkhodzhaev, B., M.K. Makhmudov, M.R. Normukhamedova, and S.A. Talipov: Crystal and Molecular Structure of the Sesquiterpene Lactone Ferulide. Khim. Chem. Abstr., 109, 211243p (1988).Google Scholar
  292. 191.
    Serkerov, S.V.: Lactones of Ferula badkhysi. Khim. Prir. Soedin., 12, 393 (1976)Google Scholar
  293. Serkerov, S.V.: Lactones of Ferula badkhysi. Chem. Abstr. 85, 139718p (1976).Google Scholar
  294. 192.
    Rychlewska, U., and S.V. Serkerov: Structural Characterization of Badkhysin and Its C(5)-Epimer, Isobadkhysin. Acta Cryst., C47, 1872 (1991).Google Scholar
  295. 193.
    Serkerov, S.V.: Stereochemistry of the Eudesmanolides from Ferula oopoda. Khim. Prir. Soedin., 16, 510 (1980)Google Scholar
  296. Serkerov, S.V.: Stereochemistry of the Eudesmanolides from Ferula oopoda. Khim. Chem. Abstr., 94, 65869a (1981).Google Scholar
  297. 194.
    Rychlewska, U., B. Szczepanska, and V. Serkerov: Two Eudesmanolide Type Sesquiterpene Lactones from Umbelliferae. Acta Cryst., C48, 1543 (1992).Google Scholar
  298. 195.
    Serkerov, S.V., A.N. Aleskerova, D.M. Akhmedov, and A.M. Rasulov: A New Sesquiterpene Lactone-Opoferdin from Ferula oopoda. Khim. Prir. Soedin., 28, 284 (1992).Google Scholar
  299. 196.
    Serkerov, S.V., U. Rychlewska, A.N. Aleskerova, and N.F. Mirbabaev: A New Guaianolide, Opoferzin from the Roots of Ferula oopoda. Khim. Prir. Soedin., 3, 318 (1991)Google Scholar
  300. Serkerov, S.V., U. Rychlewska, A.N. Aleskerova, and N.F. Mirbabaev: A New Guaianolide, Chem. Abstr., 116, 211114s (1982).Google Scholar
  301. 197.
    Murray, R.D.H.: Naturally Occurring Plant Coumarins. Fortschr. Chem. Organ. Naturstoffe, 35, 199 (1978).Google Scholar
  302. 198.
    Murray, R.D.H.: Naturally Occurring Plant Coumarins. Fortschr. Chem. Organ. Naturstoffe, 58, 83 (1991).Google Scholar

Copyright information

© Springer-Verlag/Wien 1995

Authors and Affiliations

  • A. G. González
    • 1
  • J. Bermejo Barrera
    • 1
  1. 1.Instituto de Productos Naturales y Agrobiología de Canarias C.S.I.C.Centro de Productos Naturales Organicos “A. González”La Laguna, Tenerife, Canary IslandsSpain

Personalised recommendations