Skip to main content
SpringerLink
Log in

Biosynthesis of Iridoids and Secoiridoids

  • Chapter
Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

Abstract

Research on iridoids began with the discovery of asperuloside (1) (an iridoid glucoside) in 1848 and gentiopicroside (2) (a secoiridoid glucoside) in 1862. However, it was only in the late 1950’s that the structures of the compounds of this series began to be elucidated. Thus structure elucidation of the non-glycosidic iridoids iridomyrmecin (3) (1, 2, 2a) isoiridomyrmecin (4) (3, 3a, 4) and nepetalactone (5) (5) and that of the iridoid glucoside plumieride (6) (6) gradually led to the unravelling of the structures of other then unknown iridoids. Since then, large numbers of diverse new iridoids have been found and their structures have been elucidated as time progressed.

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 39.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 54.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. Pavan, M.: The Extraction and Crystallization of Iridomyrmecin. Chim. et Ind. 37, 625 (1955).

    CAS  Google Scholar 

  2. Fusco, R., R. Trave, and A. Vercellone: Constitution of Iridomyrmecin, a Natural Insecticide. Chim. et Ind. 37, 251 (1955).

    CAS  Google Scholar 

  3. Fusco, R., R. Trave, and A. Vercellone: Structure of Iridomyrmexin. ibid. 37, 958 (1955).

    CAS  Google Scholar 

  4. Cavill, G.W.K., D.L. Ford, and H.D. Locksley: Iridodial and Iridolactone. Chem. & Ind. 1956, 465.

    Google Scholar 

  5. Cavill, G.W.K., D.L. Ford, and H.D. Locksley: The Chemistry of Ants I. Terpenoid Constituents of Some Australian Iridomyrmex Species. Austral. J. Chem. 9, 288 (1956).

    Article  CAS  Google Scholar 

  6. Cavill, G.W.K., and H.D. Locksley: The Chemistry of Ants II. Structure and Configuration of Iridolactone (Isoiridomyrmecin). Austral. J. Chem. 10, 352 (1957).

    Article  CAS  Google Scholar 

  7. Bates, R.B., E.J. Eisenbraun, and S.M. Mcelvain: The Configurations of the Nepetalactones and Related Compounds. J. Amer. Chem. Soc. 80, 3420 (1958).

    Article  CAS  Google Scholar 

  8. Halpern, O., and H. Schmid: Zur Kenntnis des Plumierids. Hely. Chim. Acta 41, 1109 (1958).

    Article  CAS  Google Scholar 

  9. El-Naggar, L.J., and J.L. Beal: Iridoids, a Review. J. Natl. Prod. 43, 649 (1980).

    Article  CAS  Google Scholar 

  10. Barger, G., and C. Scholz: Über Yohimbin. Heiv. Chim. Acta 16, 1343 (1933).

    Article  CAS  Google Scholar 

  11. Hahn, G., and H. Werner: Synthese von Tetrahydroharman(4-Carbolin)-Systemen unter physiologischen Bedingungen. III. Mitteilung. Synthese des Yohimbin-Geriístes. Liebig’s Ann. Chem. 520, 123 (1935).

    CAS  Google Scholar 

  12. Wenkert, E., and N.V. Biungi: A Stereochemical Interpretation of the Biosynthesis of Indole Alkaloids. J. Amer. Chem. Soc. 81, 1474 (1959).

    Article  CAS  Google Scholar 

  13. Wenkert, E.: Alkaloid Biosynthesis. Experientia 15, 165 (1959).

    Article  CAS  Google Scholar 

  14. Thomas, R.: A Possible Biosynthetic Relationship between the Cyclopentanoid Monoterpenes and the Indole Alkaloids. Tetrahedron Letters 1961, 544.

    Google Scholar 

  15. Wenkert, E.: Biosynthesis of Indole Alkaloids. The Aspidosperma and Iboga Bases. J. Amer. Chem. Soc. 84, 98 (1962).

    Article  CAS  Google Scholar 

  16. Leete, E., and S. Ghosal: Further Studies on the Biosynthesis of the Non-Tryptophan Derived Portion of Ajmaline and Related Alkaloids. Tetrahedron Letters 1962, 1179.

    Google Scholar 

  17. Leete, E., S. Ghosal, and P.N. Edwards: Biosynthesis of the Non-Tryptophan Derived Portion of Ajmaline. J. Amer. Chem. Soc. 84, 1068 (1962).

    Article  CAS  Google Scholar 

  18. Money, T., I.G. Wright, F. Mccapra, and A.I. Scott: Biosynthesis of the Indole Alkaloids. Proc. Natl. Acad. Sci. U.S. 53, 901 (1965).

    Article  CAS  Google Scholar 

  19. Mccapra, F., T. Money, A.I. Scurf., and I.G. Wright: Biosynthesis of the Indole Alkaloids: Vindoline. Chem. Commun. 1965, 537.

    Google Scholar 

  20. Money, T., I.G. Wright, F. Mccapra, E.S. Hall, and A.I. Scott: Biosynthesis of Indole Alkaloids. Vindoline. J. Amer. Chem. Soc. 90, 4144 (1968).

    Article  CAS  Google Scholar 

  21. Goeggel, H., and D. Arigoni: The Mevalonoid Nature of Vindoline and Reserpinine. Chem. Commun. 1965, 538.

    Google Scholar 

  22. Battersby, A.R., R.T. Brown, R.S. Kapil, A.D. Plunkett, and J.B. Taylor: Biosynthesis of the Indole Alkaloids. Chem. Commun. 1966, 46.

    Google Scholar 

  23. Battersby, A.R., R.T. Brown, J.A. Knight, J.A. Martin, and A.O. Plunkett: Biosynthesis of the Indole Alkaloids from a Monoterpene. Chem. Comun. 1966, 346.

    Google Scholar 

  24. Battersby, A.R., R.T. Brown, R.S. Kapil, J.A. Knight, J.A. Martin, and A.O. Plunkett. Further Evidence Concerning the Biosynthesis of Indole Alkaloids and Quinine. Chem. Commun. 1966, 810.

    Google Scholar 

  25. Loew, P., H. Goeggel, and D. Arigoni: A Monoterpene Precursor in the Biosynthesis of Indole Alkaloids. Chem. Commun. 1966, 347.

    Google Scholar 

  26. Hall, E.S., F. Maccapra, T. Money, K. Fukumoto, J.R. Hanson, B.S. Mootoo, G.T. Phillips, and A.I. Scott: Concerning the Terpenoid Origin of Indole Alkaloids: Biosynthetic Mapping by Direct Mass Spectrometry. Chem. Commun. 1966, 348.

    Google Scholar 

  27. Leete, E., and S. Ueda: Biosynthesis of the Vinca Alkaloids. The Incorporation of Geraniol-3–14C into Catharanthine and Vindoline. Tetrahedron Letters 1966, 4915.

    Google Scholar 

  28. Battersby, A.R., R.T. Brown, R.S. Kapil, J.A. Martin, and A.O. Plunkett: Role of Loganin in the Biosynthesis of Indole Alkaloids. Chem. Commun. 1966, 812.

    Google Scholar 

  29. Battersby, A.R., R.T. Brown, R.S. Kapil, J.A. Martin, and A.O. Plunkett: Role of Loganin in the Biosynthesis of Indole Alkaloids. ibid. 1966, 890.

    Google Scholar 

  30. Battersby, A.R., R.S. Kapil, J.A. Martin, and L. Mo: Loganinas Precursor of the Indole Alkaloids. Chem. Commun. 1968, 133.

    Google Scholar 

  31. Loew, P., and D. Arigoni: The Biological Conversion of Loganin into Indole Alkaloids. Chem. Commun. 1968, 137.

    Google Scholar 

  32. Bobbitt, J.M., and K.P. Segebarmh: Iridoid Glycosides and Similar Substances. In: Cyclopentanoid Terpene Derivatives. p. 1. Edited by Taylor, W.I., and A.R. Battersby. New York: Marcel Dekker, Inc. 1969.

    Google Scholar 

  33. Inouye, H.: Biosynthesis of Iridoid-and Secoiridoid Glucosides. In: Pharmacognosy and Phytochemistry 1970, p. 290. Edited by Wagner, H., and L. Hörhammer. Springer, Berlin-Heidelberg-New York:1970.

    Google Scholar 

  34. Gross, D.: Die Biosynthese Iridoider Naturstoffe. Fortschritte der Botanik 32, 93 (1970).

    Google Scholar 

  35. Plouvier, V., and J. Favre-Bonvin: Phytochemistry 10, 1697 (1971).

    Article  CAS  Google Scholar 

  36. Cordell, G.A.: The Biosynthesis of Indole Alkaloids. Lloydia 37, 219 (1974).

    CAS  Google Scholar 

  37. Inouye, H., S. Ueda, and Y. Takeda: Biosynthesis of Secoiridoid Glucosides. Heterocycles 4, 527 (1976).

    Article  CAS  Google Scholar 

  38. Inouye, H.: Neuere Ergebnisse über die Biosynthese der Glucoside der Iridoidreihe. Planta Med. 33, 193 (1978).

    Article  CAS  Google Scholar 

  39. Tietze, L.-F.: Secologanin, a Biogenetic Key Compound - Synthesis and Biogenesis of the Iridoid and Secoiridoid Glycosides. Angew. Chem. Int. Ed. 22, 828 (1983).

    Google Scholar 

  40. Inouye, H., S. Ueda, Y. Aoki, and Y. Takeda: Studies on Monoterpene Glucosides and Related Natural Products. XVII. The Intermediacy of 7-Desoxyloganic Acid and Loganin in the Biosynthesis of Several Iridoid Glucosides. Chem. Pharm. Bull. (Japan) 20, 1287 (1972).

    Article  CAS  Google Scholar 

  41. Inouye, H., S. Ueda, and Y. Takeda: Studies on Monoterpene Glucosides and Related Natural Products. XVIII. Formation Sequences of Iridoid Glucosides in Highly Oxidized Levels. Chem. Pharm. Bull. (Japan) 20, 1305 (1972).

    Article  CAS  Google Scholar 

  42. Inouye, H., S. Ueda, and S. Uesato: Zuni Mechanismus der MethylcyclopentanGerüstbildung bei der Biosynthese einiger Iridoidglucoside. Tetrahedron Letters 1977, 709.

    Google Scholar 

  43. Inouye, H., S. Ueda, and S. Uesato: Über die Biosynthese des Deutziosids. Tetrahedron Letters 1977, 713.

    Google Scholar 

  44. Inouye, H., S. Ueda, and S. Uesato: Intermediacy of Iridodial in the Biosynthesis of Some Iridoid Glucosides. Phytochem. 16, 1669 (1977).

    Article  CAS  Google Scholar 

  45. Inouye, H., S. Ueda, S. Uesato, and K. Kobayashi: Studies on Monoterpene Glucosides and Related Natural Products. XXXVII. Biosynthesis of the Iridoid Glucosides in Lamium amplexicaule, Deutzia crenata and Galium spurium var. echinospermon. Chem. Pharm. Bull. (Japan) 26, 3384 (1978)

    Article  CAS  Google Scholar 

  46. Damtoft, S.: Biosynthesis of Lamiide and Ipolamiide from 8-epi-Deoxyloganin Studied by 2H N.M.R. Spectroscopy. J.C.S. Chem Comm. 1981, 228.

    Google Scholar 

  47. Damtoft, Biosynthesis of the Iridoids Aucubin and Antirrinoside from 8-Epi-Deoxyloganic Acid. Phytochem 22, 1929 (1983).

    Article  Google Scholar 

  48. Uesato, S., S. Ueda, K. Kobayashi, and H. Inouye: Mechanism of Iridane Skeleton Formation in the Biosynthesis of Iridoid Glucosides in Gardenia jasminoides Cell Cultures. Chem. Pharm. Bull. (Japan) 31, 4185 (1983).

    Article  CAS  Google Scholar 

  49. Uesato, S., S. Ueda, K. Kobayashi, M. Miyauchi, and H. Inouye: Biosynthetic Pathway of Iridoid Glucosides in Gardenia jasminoides f. grandiflora Cell Suspension Cultures after Iridodial Cation Formation. Tetrahedron Letters 25, 573 (1984).

    Article  CAS  Google Scholar 

  50. Kobayashi, K., S. Uesato, S. Ueda, and H. Inouye: Studies on Monoterpene Glucosides and Related Natural Products. LV. Iridane Skeleton Formation from Acyclic Monoterpenes in the Biosynthesis of Iridoid Glucosides in Gardenia jasminoides f. grandiflora Cell Suspension Cultures. Chem. Pharm. Bull. (Japan) 33, 4228 (1985).

    Article  CAS  Google Scholar 

  51. Uesato, S., S. Ueda, K. Kobayashi, M. Miyauchi, H. Itox, and H. Inouye: Intermediacy of 8-Epiiridodial in the Biosynthesis of Iridoid Glucosides of Gardenia jasminoides Cell Cultures. Phytochem. 25, 2309 (1986).

    Article  CAS  Google Scholar 

  52. Uesato, S., M. Miyauchi, H. Prof, and H. Inoun: Biosynthesis of Iridoid Glucosides in Galium mollugo, Galium spurium var. echinospermon and Deutzia crenata. 25 in press (1986).

    Google Scholar 

  53. Bellesia, F., U.M. Pagnoni, A. Pinetti, and R. Trave: The Biosynthesis of Dolichodial in Teucrium marum. Phytochem. 22, 2197 (1983).

    Article  CAS  Google Scholar 

  54. Grandi, R., U.M. Pagnoni, A. Pinetn, and R. Trave: Biosynthesis of Dolicholactone in Teucrium marum. Phytochem. 22, 2723 (1983).

    Article  CAS  Google Scholar 

  55. Bellesia, F., U.M. Pagnoni, A. Pmern, and R. Trave: Teucrein, a New Iridolactol from Teucrium marum, and its Biosynthetic Relationship with Dolichodial. J. Chem Research(s) 1983, 328.

    Google Scholar 

  56. Bellesia, F., U.M. Pagnoni, A. Pmern, and R. Trave: The Intermediacy of Iridodial in the Biosynthesis of Dolicholactone in Teucrium marum. J. Chem. Research(s) 1984, 192.

    Google Scholar 

  57. Bellesia, F., R. Grandi, U.M. Pagnoni, A. Pinern, and R. Trame: Biosynthesis of Nepetalactone in Nepeta cataria. Phytochem. 23, 83 (1984).

    Article  CAS  Google Scholar 

  58. Grandi, R., U.M. Pagnoni, A. Pinerri, and R. Trave: The Possible Role of Photocitral-A in the Biosynthesis of Cyclopentane Monoterpenes. J. Chem. Research(s) 1984, 194.

    Google Scholar 

  59. Murai, F., M. Tagawa, S. Damtoft, S.R. Jensen, and B.J. Nielsen, (1R,5R,8S,9S)Deoxyloganic Acid from Nepeta cataria. Chem. Pharm. Bull. (Japan) 32, 2809 (1984).

    Article  CAS  Google Scholar 

  60. Tagawa, M., and F. Murai: A New Iridoid Glucoside from Actinidia polygama. Abstract Papers (II) of the 50th Annual Meeting of the Chemical Society of Japan, p. 918 (1985).

    Google Scholar 

  61. Jensen, S.R., B.J. Nielsen, and R. Dahlgren: Iridoid Compounds, Their Occurrence and Systematic Importance in Angiosperms. Bot. Notiser. 128, 148 (1975).

    CAS  Google Scholar 

  62. Yeowell, D.A., and H. Schmid: Zur Biosynthese des Plumierids. Experientia 20, 250 (1964).

    Article  CAS  Google Scholar 

  63. Clark, K.J., G.I. Fray, R.H. Jaeger, and R. Robinson: Synthesis of D- and LIsoiridomyrmecin and Related Compounds. Tetrahedron 6, 217 (1959).

    Article  CAS  Google Scholar 

  64. Coscia, C.J., and R. Guarnaccia: Biosynthesis of Gentiopicroside, a Novel Monoterpene. J. Amer. Chem. Soc. 89, 1280 (1967).

    Article  CAS  Google Scholar 

  65. Coscia, C.J., R. Guarnaccia, and L. Botta: Monoterpene Biosynthesis. I. Occurrence and Mevalonoid Origin of Gentiopicroside and Loganic Acid in Swertia caroliniensis. Biochemistry 8, 5036 (1969).

    Article  CAS  Google Scholar 

  66. Inouye, H., S. Ueda, and Y. Nakamura: Zur Biosynthese der Bitteren Glucoside der Genzianaceen, des Gentiopicrosids, des Swertiamarins und des Swerosids. Tetrahedron Letters 1967, 3221.

    Google Scholar 

  67. Inouye, H., S. Ueda, and Y. Nakamura: Studies on Monoterpene Glucosides XII. Biosynthesis of Gentianaceous Secoiridoid glucosides. Chem. Pharm. Bull. (Japan) 18, 2043 (1970).

    Article  CAS  Google Scholar 

  68. Guarnaccia, R., L. Botta, and C.J. Coscia: Mechanism of Secoiridoid Monoterpene Biosynthesis. J. Amer. Chem. Soc. 91, 204 (1969).

    Article  CAS  Google Scholar 

  69. Coscia, C.J., L. Botta, and R. Guarnaccia: On the Mechanism of Iridoid and Secoiridoid Monoterpene Biosynthesis. Arch. Biochem. Biophys. 136, 498 (1970).

    Article  CAS  Google Scholar 

  70. Guarnaccia, R., and C.J. Coscia: Occurrence and Biosnthesis of Secologanic Acid in Vinca rosea. J. Amer. Chem. Soc. 93, 6320 (1971).

    Article  CAS  Google Scholar 

  71. Guarnaccia, R., L. Botta, and C.J. Coscia: Biosynthesis of Acidic Iridoid Monoterpene Glucosides in Vinca rosea. J. Amer. Chem. Soc. 96, 7079 (1974).

    Article  CAS  Google Scholar 

  72. Auda, H., H.R. Juneja, E.J. Eisenbraun, G.R. Waller, W.R. Kays, and H.H. Appel: Biosynthesis of Methylcyclopentane Monoterpenoids. I. Skytanthus Alkaloids. J. Amer. Chem. Soc. 89, 2476 (1967).

    CAS  Google Scholar 

  73. Auda, H., G.R. Waller, and E.J. Eisenbraun: Biosynthesis of Methylcyclopentane Monoterpenoids. III. Actinidine. J. Biol. Chem. 242, 4157 (1967).

    CAS  Google Scholar 

  74. Horodysky, A.G., G.R. Waller, and E.J. Eisenbraun: Biosynthesis of Methylcyclopentane Monoterpenoids. IV. Verbenalin. J. Biol. Chem. 244, 3110 (1969).

    CAS  Google Scholar 

  75. Hül, J.E.S., H. Hiltebrand, H. Schmid, D. Gröger, S. Johne, and K. Mothes: Zur Bioosynthese des Verbenalins und Aucubins. Experientia 22, 656 (1966).

    Article  Google Scholar 

  76. Regnier, F.E., G.R. Waller, E.J. Eisenbraun, and H. Auda: The Biosynthesis of Methylcyclopentane Monoterpenoids - II. Nepetalactone. Phytochem. 7, 221 (1968).

    Article  CAS  Google Scholar 

  77. Loew, P., CH. Von Szczepanski, C.J. Coscia, and D. Arigoni: The Structure and Biosynthesis of Foliamenthin. Chem. Commun. 1968, 1276.

    Google Scholar 

  78. Battersby, A.R., A.R. Burnett, G.D. Knowles, and P.G. Parsons: Seco-cyclopentane Glucosides from Menyanthes trifoliata: Foliamenthin, Dihydrofoliamenthin, and Menthiafolin. Chem. Commun. 1968, 1277.

    Google Scholar 

  79. Battersby, A.R., and R.J. Parry: Biosynthesis of the Ipecac Alkaloids and of Ipecoside. Chem. Commun. 1971, 901.

    Google Scholar 

  80. Coscia, C.J., and R. Guarnaccia: Natural Occurrence and Biosynthesis of a Cyclopentanoid Monoterpene Carboxylic Acid. Chem. Commun. 1968, 138.

    Google Scholar 

  81. Escher, S., P. Loew, and D. Arigoni: The Role of Hydroxygeraniol and Hydroxynerol in the Biosynthesis of Loganin and Indole Alkaloids. Chem. Commun. 1970, 823.

    Google Scholar 

  82. Battersby, A.R., S.H. Brown, and T.G. Payne: Biosynthesis of Loganin and the Indole Alkaloids from Hydroxygeraniol-Hydroxynerol. Chem. Commun. 1970, 827.

    Google Scholar 

  83. Meehan, T.D., and C.J. Coscia: Hydroxylation of Geraniol and Nerol by a Monooxygenase from Vinca rosea. Biochem. Biophys. Res. Comm. 53, 1043 (1973).

    Article  CAS  Google Scholar 

  84. Bowman, R.M., and E. Leete: Observations on the Administration of Iridodial-714C to Vinca rosea. Phytochem. 8, 1003 (1969).

    Article  CAS  Google Scholar 

  85. Ueda, S., K. Kobayashi, T. Muramatsu, and H. Inouye: Studies on Monoterpene Glucosides and related Natural Products. Part XL. Iridoid Glucosides of Cultured Cells of Gardenia jasminoides f. grandiflora. Planta Med. 41, 186 (1981).

    Article  CAS  Google Scholar 

  86. Uesato, S., K. Kobayashi, and H. Inouye: Studies on Monoterpene Glucosides and Related Natural Products. XLV. Synthesis of 13C-Labeled Acyclic Monoterpenes for Studies on the Mechanism of the Iridane Skeleton Formation in the Biosynthesis of Iridoid Glucosides. Chem. Pharm. Bull. (Japan) 30, 927 (1982).

    Article  CAS  Google Scholar 

  87. Battersby, A.R., M. Thompson, K.-H. Gldsenkamp, and L.-F. Tietze: Untersuchungen zur Biogenese der Indolalkaloide. Synthese und Verfütterung radioaktiv markierter Monoterpenaldehyde. Chem. Ber. 114, 3430 (1981).

    Article  CAS  Google Scholar 

  88. Balsevich, J., and W.G.W. Kurz: The Role of 9- and/or 10-Oxygenated Derivatives of Geraniol, Geranial, Nerol, and Neral in the Biosynthesis of Loganin and Ajmalicine. Planta Med. 49, 79 (1983).

    Article  CAS  Google Scholar 

  89. Uesato, S., S. Matsuda, and H. Inouye: Mechanism for Iridane Skeleton Formation from Acyclic Monoterpenes in the Biosynthesis of Secologanin and Vindoline in Catharanthus roseus and Lonicera morrowii. Chem. Pharm. Bull. (Japan) 32, 1671 (1984).

    Article  CAS  Google Scholar 

  90. Uesato, S., S. Matsuda, and H. Inouye: Studies on Monoterpene Glucosides and Related Natural Products. LII. Mechanism for Iridane Skeleton Formation from Acyclic Monoterpenes in the Biosynthesis of Secoiridoid Glucosides and Indole Alkaloids. Yakugaku Zasshi 104, 1232 (1984).

    CAS  Google Scholar 

  91. Stöckigt, J., A. Pfitzner, and J. Full: Indole Alkaloids from Cell Suspension Cultures of Rauwolfia serpentine Benth. Plant Cell Reports 1, 36 (1981).

    Article  Google Scholar 

  92. Uesato, S., S. Matsuda, A. Iida, H. Inouye, and M.H. Zenk: Intermediacy of 10-Hydroxygeraniol, 10-Hydroxynerol and Iridodial in the Biosynthesis of Ajmaline and Vomilenine in Rauwolfia serpentine Suspension Cultures. Chem. Pharm. Bull. (Japan) 32, 3764 (1984).

    Article  CAS  Google Scholar 

  93. Uesato, S., S. Kanomi, A. Iida, H. Inouye, and M.H. Zenk: Mechanism for Iridane Skeleton Formation in the Biosynthesis of Secologanin and Indole Alkaloids in Plants of Lonicera tatarica and Catharanthus roseus and Suspension Cultures of Rauwolfia serpentin. Phytochem. 25, 839 (1986).

    Article  CAS  Google Scholar 

  94. Uesato, S., Y. Ogawa, H. Inouye, K. Saiiu, and M.H. Zenk: Synthesis of Iridodial by Cell Free Extracts from Rauwolfia serpentina Cell Suspension Cultures. Tetrahedron Letters 27, 2893 (1986).

    Article  CAS  Google Scholar 

  95. Cooicson, R.C., J. Hudec, S.A. Knight, and B.R.D. Whitear: The Photochemistry of Citral. Tetrahedron 19, 1995 (1963).

    Google Scholar 

  96. Cookson, R.C.: The Photochemistry of Some Allylic Compounds. Quart. Rev. 22, 423 (1968).

    Article  CAS  Google Scholar 

  97. Uesato, S., H. Itoh, S. Xie, and H. Inouye: unpublished results.

    Google Scholar 

  98. Inouye, H., S. Ueda, Y. Amu, and Y. Takeda: Zur Biosynthese der Iridoidglucoside. Tetrahedron Letter 1969, 2351.

    Google Scholar 

  99. Inouye, H., S. Ueda, Y. Amu, and Y. Takeda: Studies on Monoterpene Glucosides and Related Natural Products. XVII. The Intermediacy of 7-Desoxyloganic Acid and Loganin in the Biosynthesis of Several Iridoid Glucosides. Chem. Pharm. Bull. (Japan) 20, 1287 (1972).

    Article  CAS  Google Scholar 

  100. Rimpler, H., and B. Von Lehmann: Bisdesoxydihydromonotropein aus Physostegia virginiana. Phytochem. 9, 641 (1970).

    Article  CAS  Google Scholar 

  101. Battersby, A.R., A.R. Burnett, and P.G. Parsons: Preparation and Isolation of Deoxyloganin: Its Role as Precursor of Loganin and the Indole Alkaloids. Chem. Commun. 1970, 826.

    Google Scholar 

  102. Madyastha, K.M., R. Guarnaccia, and C.J. Coscia: Enzymic Synthesis of Loganin by Carboxyl Group Methylation of Loganic Acid. FEBS Letters 14, 175 (1971).

    Article  CAS  Google Scholar 

  103. Madyastha, K.M., R. Guarnaccia, C. Baxter, and C.J. Coscia: S-Adenosyl-Lmethionine: Loganic Acid Methyltransferase. J. Biol. Chem. 248, 2497 (1973).

    CAS  Google Scholar 

  104. Battersby, A.R., A.R. Burnett, E.S. Hall, and P.G. Parsons: The Rearrangement Process in Indole Alkaloid Biosynthesis. Chem Commun. 1968, 1582.

    Google Scholar 

  105. Inouye, H., S. Ueda, K. Inoue, and Y. Takeda: Studies on Monoterpene Glucosides and Related Natural Products. XXIII. Biosynthesis of the Secoiridoid Glucosides, Gentiopicroside, Morroniside, Oleuropein, and Jasminin. Chem. Pharm. Bull. (Japan) 22, 676 (1974).

    Article  CAS  Google Scholar 

  106. Gröger, D., and P. Simchen: Über den Einbau von Loganin in Gentiopicrosid. Naturforsch. 241), 356 (1969).

    Google Scholar 

  107. Inouye, H., S. Ueda, and Y. Takeda: Zur Biosynthese des Morronisids. Tetrahedron Letters 1971, 4069.

    Google Scholar 

  108. Bairersby, A.R., A.R. Burnett, and P.G. Parsons: Alkaloid Biosynthesis. Part XIV. Secologanin Its Conversion into Ipecoside and Its Role as Biological Precursor of the Indole Alkaloids. J. Chem. Soc. (C) 1969, 1187.

    Google Scholar 

  109. Inouye, H., S. Ueda, and Y. Takeda: Loganin als precursor in der Biosynthese des Asperulosids. Naturforsch. 24b, 1666 (1969).

    CAS  Google Scholar 

  110. Damtoft, S., S.R. Jensen, and B.J. Nielsen: Application of 2H N.M.R. Spectroscopy to a Study of the Biosynthesis of the Iridoid Glucosides Comin in Verbena officinalis. J. C. S. Chem. Commun. 1980, 42.

    Google Scholar 

  111. Inouye, H., S. Ueda, and Y. Takeda: Loganin als precursor in der Biosynthese des Asperulosids. Naturforsch. 24b, 1666 (1969).

    CAS  Google Scholar 

  112. Damtofr, S., M.U. Jars, S.R. Jensen, O. Kirk, and B.J. Nieisen, The Effect of Metabolic Period, Dose and Application Method on the Incorporation of Deoxyloganin into Comin in Verbena officinalis. Phytochemistry 22, 695 (1983).

    Article  Google Scholar 

  113. Jensen, S.R., and B.J. Nielsen private communication.

    Google Scholar 

  114. Damtoft, S., S.R. Jensen, and B.J. Nielsen, The Biosynthesis of Iridoid Glucosides from 8-epi-Deoxyloganic Acid. Biochem. Soc. Transactions 11, 593 (1983).

    CAS  Google Scholar 

  115. Uesato, S., H. Iron, and H. Inouye: unpublished results.

    Google Scholar 

  116. Uesato, S., E. Au, H. Nishimura, I. Kawamuaa, and H. Inouye: Four Iridoids from Randia canthioides. Phytochem. 21, 353 (1982).

    Article  CAS  Google Scholar 

  117. Indue, K., Y. Takeda, H. Nishimura, and H. Inouye: Studies on Monoterpene Glucosides and Related Natural Products. XXXIX. Biogenetic-type Transformation of Geniposide into Plumieride. Chem. Pharm. Bull. (Japan) 27, 3115 (1979).

    Article  Google Scholar 

  118. Kupchan, S.M., A.L. Dessertine, B.T. Blaylock, and R.F. Bryan: Isolation and Structural Elucidation of Allamandin, an Antileukemic Iridoid Lactone from Alla-manda cathartica. J. Org. Chem. 39, 2477 (1974).

    CAS  Google Scholar 

  119. Adesogan, E.K.: Oruwacin, A New Iridoid Ferulate from Morinda lucida. Phytochem. 18, 175 (1979).

    Article  CAS  Google Scholar 

  120. Jensen, S.R., B.J. Nielsen, C.B. Mikkelsen, J.J. Hoffmann, S.D. Jolad, and J.R. Cole: The Revised Structure of Penstemide. Tetrahedron Letters 1979, 3261.

    Google Scholar 

  121. Djerassi, C., T. Nakano, A.N. James, L.H. Zalkow, E.J. Eisenbraun, and J.N. Shoolery: Terpenoids. XLVII. The Structure of Genipin. J. Org. Chem. 26, 1192 (1961).

    Article  CAS  Google Scholar 

  122. Miles, D.H., U. Kokpol, J. Bhattacharyya, J.L. Atwood, K.E. Stone, T.A. Bryson, and C. Wilson: Structure of Sarracenin. An unusual Enol Diacetal Monoterpene from the Insectivorous Plant Sarracenia flava. J. Amer. Chem. Soc. 98, 1569 (1976).

    Article  CAS  Google Scholar 

  123. Kubo, I., I. Miura, and K. Nakanishi: The Structure of Xylomollin, a Secoiridoid Hemiacetal Acetal. J. Amer. Chem. Soc. 98, 6704 (1976).

    Article  CAS  Google Scholar 

  124. Bock, K., S.R. Jensen, B.J. Nielsen, and V. Norn: Iridoid Allosides from Viburunum opulus. Phytochem. 17, 753 (1978).

    Article  CAS  Google Scholar 

  125. S.R. Jensen, B.J. Nielsen, and V. Nom: Iridoids from Viburnum betulifolium. Phytochem. 24, 487 (1985).

    Article  CAS  Google Scholar 

  126. Taguchi, H., Y. Yokokawa, and T. Endo: Studies on the Constituents of Patrinia villosa. Yakugaku Zasshi 93, 607 (1973).

    CAS  Google Scholar 

  127. Taguchi, H., and T. Endo: Patrinoside, a New Iridoid Glycoside from Patrinia scabiosaefolia. Chem. Pharm. Bull. (Japan) 22, 1935 (1974).

    Article  CAS  Google Scholar 

  128. Bal Iursby, A.R.: Biosynthesis of the Indole and Colchicum Alkaloids. Pure and Appl. Chem. 14, 117 (1967).

    Google Scholar 

  129. Battersby, A.R., B. Gregory, H. Spencer, J.C. Turner, M.-M. Janot, P. Potier, P. Francois, and J. Levisalles, Constitution of Ipecoside: A Monoterpenoid Isoquinoline. Chem. Commun. 1967, 219.

    Google Scholar 

  130. Battersby, A.R., A.R. Burnett, and P.G. Parsons: Preparation of Secologanin its Conversion into Ipecoside and its Role in Indole Alkaloid Biosynthesis. Chem. Commun. 1968, 1280.

    Google Scholar 

  131. Battersby, A.R., A.R. Burnett, and P.G. Parsons: Partial Synthesis and Isolation of Vincoside and Isovincoside: Biosynthesis of the Three Major Classes of Indole Alkaloids from the ß-Carboline Systen. Chem. Commun. 1968, 1282.

    Google Scholar 

  132. Battersby, A.R., A.R. Burnett, and P.G. Parsons: Alkaloid Biosynthesis. Part XV. Partial Synthesis and Isolation of Vincoside and Isovincoside: Biosynthesis of the Three Major Classes of Indole Alkaloids from Vincoside. J. Chem. Soc. (C) 1969, 1193.

    Google Scholar 

  133. Souzu, I., and H. Mitsuhashi: Structures of Iridoids from Lonicera morrowii A. Gray. II. Tetrahedron Letters 1970, 191.

    Google Scholar 

  134. Popov, S., and N. Maarekov: A New Iridoid Precursor of Gentiopicroside. Phytochem. 10, 3077 (1971).

    Article  CAS  Google Scholar 

  135. Baitersby, A.R., and K.H. Gibson: Further Studies on Rearrangements during Biosynthesis of Indole Alkaloids. Chem. Commun. 1971, 902.

    Google Scholar 

  136. Takeda, Y., and H. Inouye: Studies on Monoterpene Glucosides and Related Natural Products. XXX. The Fate of the C-8 Proton of 7-Deoxyloganic Acid in the Biosynthesis of Secoiridoid Glucosides. Chem. Pharm. Bull. (Japan) 24, 79 (1976).

    Article  CAS  Google Scholar 

  137. Hutchinson, C.R., A.H. Heckendorf, and P.E. Daddona: Biosynthesis of Camptothecin. I. Definition of the Overall Pathway Assisted by Carbon-13 Nuclear Magnetic Resonance Analysis. J. Amer. Chem. Soc. 96, 5609 (1974).

    CAS  Google Scholar 

  138. Tietze, L.-F.: Totalsynthese von Hydroxyloganin und Hydroxyloganinsäure. Angew. Chem. 85, 763 (1973).

    Article  CAS  Google Scholar 

  139. Tietze, L.-F.: Iridoide, IV Totalsynthese von Hydroxyloganin und Hydroxyloganinsäure. Chem. Ber. 107, 2499 (1974).

    Article  CAS  Google Scholar 

  140. Tietze, L.-F.: Fragmentation of Hydroxyloganin Derivatives. An Assay to Secologanin Type Compounds. J. Amer. Chem. Soc. 96, 946 (1974).

    Article  CAS  Google Scholar 

  141. Tietze, L.-F.: Iridoide, V Biogenetische Synthese von Secologanin-und Swerosid-aglyconmethyläther. Chem. Ber. 109, 3626 (1976).

    Article  Google Scholar 

  142. Inoue, K., Y. Takeda, T. Tanahashi, and H. Inouye: Studies on Monoterpene Glucosides and Related Natural Products. XLI. Chemical Conversion of Geniposide into 10-Hydroxyloganin. Chem. Pharm. Bull. (Japan) 29, 970 (1981).

    Article  CAS  Google Scholar 

  143. Inoue, K., Y. Takeda, T. Tanahashi, and H. Inouye: Studies on Monoterpene Glucosides and Related Natural Products. XLII. On the Possibility of the Intermediacy of 10-Hydroxyloganin in the Biosynthesis of Secologanin Chem. Pharm. Bull. (Japan) 29, 98 (1981).

    Article  Google Scholar 

  144. Battersby, A.R., N.D. Westcott, K.-H. Glüsenkamp, and L.-F. Tietze: Untersuchungen zur Biogenese der Indolalkaloide. Synthese und Verfütterung radioaktiv markierter Hydroxyloganin-Derivate. Chem Ber. 114, 3439 (1981).

    Article  CAS  Google Scholar 

  145. Inoue, K., H. Kuwarma, K. Takaishi, and H. Inouye: unpublished results.

    Google Scholar 

  146. Partridge, J.J., N.K. Chadha, S. Faber, and M.R. Usxoxovlc: Lead Tetraacetate Fragmentation of Loganin Aglucone 0-Methyl Ether and Its stereoisomers. Synth. Commun. 1, 233 (1971).

    Article  Google Scholar 

  147. Uesato, S., T. Hashimoto, and H. Inouye: Three New Secoiridoid Glucosides from 5- Eustoma russellianum. Phytochem. 18, 1981 (1979).

    Google Scholar 

  148. Balenovic, K., H.U. Däniker, R. Goutarel, M.M. Janot, and V. Prelog: Über Bakankosin. Heiv. Chim. Acta 35, 2519 (1952).

    Article  CAS  Google Scholar 

  149. Murai, F., M. Tagawa, S. Matsuda, T. Kikuchi, S. Uesato, and H. Inouye: Abeliosides A and B, Secoiridoid Glucosides from Abelia grandora. Phytochem. 24, 2329 (1985).

    Article  CAS  Google Scholar 

  150. Inouye, H., S. Ueda, and Y. Takeda: The Biological Conversion of Sweroside into Gentiopicroside and Vindoline. Tetrahedron Letters 1968, 3453.

    Google Scholar 

  151. Inouye, H., S. Ueda, and Y. Takeda: Studies on Monoterpene Glucosides and Related Natural Products. XIII. Incorporation of [10–14C]Sweroside into Gentiopicroside and the Alkaloids in Vinca and Cinchona Plants. Chem. Pharm. Bull. (Japan) 19, 587 (1971).

    Article  CAS  Google Scholar 

  152. Inouye, H., S. Ueda, and Y. Takeda: Zur Biosynthese der Vinca-sowie der Cinchonaalkaloide. Inkorporation des Swerosids in Reserpinin und Chinin. Tetrahedron Letters 1969, 407.

    Google Scholar 

  153. Inouye, H., S. Tobita, and M. Moriguchi: Studies on Monoterpene Glucosides and Related Natural Products. XXXIII. Structure of Bakankosin. Chem. Pharm. Bull. (Japan) 24, 1406 (1976).

    Article  CAS  Google Scholar 

  154. Tietze, L.-F.: Synthese und Strukturbeweis von Bakankosin. Tetrahedron Letters 1976, 2535.

    Google Scholar 

  155. Kitagawa, I., T. Tani, K. Akita, and I. Yosioka: On the Constituents of Linaria japonica Miq. I. The Structure of Linarioside, a New Chlorinated Iridoid Glucoside and Identification of Two Related Glucosides. Chem. Pharm. Bull. (Japan) 21, 1978 (1973).

    Google Scholar 

  156. Inouye, H., and Y. Nakamura: Zwei stark bittere Glucoside aus Swertia japonica Makino Amarogentin und Amaroswerin. Tetrahedron Letters 1968, 4919.

    Google Scholar 

  157. Inouye, H., and Y. Nakamura: Über die Monoterpenglucoside und verwandte Naturstoffe. XIV. Die Struktur der beiden stark bitter schmeckenden Glucoside Amarogentin und Amaroswerin aus Swertia japonica. Tetrahedron 27, 1951 (1971).

    Article  CAS  Google Scholar 

  158. Inouye, H., and Y. Nakamura: Studies on Monoterpene Glucosides and Related Natural Products. XVI. Occurrence of Secoiridoid Glucosides in Gentianaceous Plants especially in the Genera Gentiana and Swertia. Yakugaku Zasshi 91, 755 (1971).

    CAS  Google Scholar 

  159. Wagner, H., and K. Vasirian: Desoxyamarogentin, ein neuer Bitterstoff aus Gentiana pannonica Scop. Phytochem. 13, 615 (1974).

    Article  CAS  Google Scholar 

  160. Sakina, K., and K. Aota: Studies on the Constituents of Erythraea centaurium (Linne) Persoon. I. The Structure of Centapicrin, a New Bitter Secoiridoid Glucoside. Yakugaku Zasshi 96, 683 (1976).

    CAS  Google Scholar 

  161. Van Der Slüis, W.G., and R.P. Labadie: Secoiridoids and Xanthones in the Genus Centaurium Part III: Decentapicrins A, B and C, New m-Hydroxybenzoyl Esters of Sweroside from Centaurium littorale. Planta Med. 41, 150 (1981).

    Article  Google Scholar 

  162. Endo, T., and H. Taguchi: Study on the Constituents of Cornus officinalis Sieb. et Zucc. Yakugaku Zasshi 93, 30 (1973).

    CAS  Google Scholar 

  163. Bock, K., S.R. Jensen, and B.J. Nielsen, Secogalioside, an Iridoid Glucoside from Galium album Mill. and 13C NMR Spectra of some Seco-iridoid Glucosides. Acta Chem. Scand. B 30, 743 (1976).

    Article  Google Scholar 

  164. Uesato, S., M. Ueda, H. Inouye, H. Kuwajima, M. Yatsuzuka, and K. Takaishi. Iridoids from Galium mollugo. Phytochem. 23, 2535 (1984).

    Article  CAS  Google Scholar 

  165. Inouye, H., T. Yoshida, S. Tobita, K. Tanaka, and T. Nishioka: Über die Monoterpenglucoside und verwandte Naturstoffe. XXII. Absolutstruktur des Oleuropeins, Kingisids und Morronisids. Tetrahedron 30, 201 (1974).

    Article  CAS  Google Scholar 

  166. Inouye, H., S. Ueda, K. Inoue, and Y. Takeda: Ober die Biosynthese der Oleuropein-Typ-Secoiridoidglucoside der Oleaceae. Tetrahedron Letters 1971, 4073.

    Google Scholar 

  167. Lavie, D., and E.C. Levy: Oxidative Reactions of Biogenetic Interest. Tetrahedron Letters 1970, 1315.

    Google Scholar 

  168. Conrad, H.E., R. Duaus, M.J. Namtvedt, and I.C. Gunsalus: Mixed Function Oxidation. II. Separation and Properties of the Enzymes Catalyzing Camphor Lactonization. J. Biol. Chem. 240, 495 (1965).

    CAS  Google Scholar 

  169. Inoue, K., T. Nishidka, T. Tanahashi, and H. Inouye: Three Secoiridoid Glucosides from Ligustrum japonicum. Phytochem. 21, 2305 (1982).

    Article  CAS  Google Scholar 

  170. Smith, G.N.: Strictosidine: A Key Intermediate in the Biosynthesis of Indole Alkaloids. Chem. Commun. 1968, 912.

    Google Scholar 

  171. De Silva, K.T.D., G.N. Smith, and K.E.H. Warren: Biochemistry of Strictosidine. Chem. Commun. 1971, 905.

    Google Scholar 

  172. De Silva, K.T.D., G.N. Smith, and K.E.H. Warren: Stereochemistry of Strictosidine. Chem. Commun. 1971, 905.

    Google Scholar 

  173. Blackstock, W.P., R.T. Brown, and G.K. Lee: Configuration at C-3 in Vincoside. Chem. Commun. 1971, 910.

    Google Scholar 

  174. Kennard, O., P.J. Roberts, N.W. Isaacs, F.H. Allen, W.D.S. Motherwell, K.H. Gibson, and A.R. Battersby: X-Ray Determination of the Structure of 0,0-Dimethylipecoside. Chem. Commun. 1971, 899.

    Google Scholar 

  175. Mattes, K.C.,C.R. Hutchinson, J.P. Springer, and J. Clardy: Absolute Configuration of Vincoside. J. Amer. Chem. Soc. 97, 6270 (1975).

    Article  CAS  Google Scholar 

  176. Hutchinson, C.R., A.H. Heckendorf, and P.E. Daddona: Biosynthesis of Camptothecin. I. Definition of the Overall Pathway Assisted by Carbon-13 Nuclear Magnetic Resonance Analysis. J. Amer. Chem. Soc. 96, 5609 (1974).

    CAS  Google Scholar 

  177. Brown, R.T., J. Leonard, and S.K. Sleigh: One-pot Biomimetic Synthesis of 19/1Heterojohimbine Alkaloids. J.C.S. Chem. Comm. 1977, 636.

    Google Scholar 

  178. Stöckigt, J., J. Treimer, and M.H. Zenk: Synthesis of Ajmalicine and Related Indole Alkaloids by Cell Free Extracts of Catharanthus roseus Cell Suspension Cultures. FEBS Letters 70, 267 (1976).

    Article  Google Scholar 

  179. Stöckigt, J., and M.H. Zenk: Isovincoside (Strictosidine), the Key Intermediate in the Enzymatic Formation of Indole Alkaloids. FEBS Letters 79, 233 (1977).

    Article  Google Scholar 

  180. Stöckigt, J., H.P. Husson, C. Kan-Fan, and M.H. Zenk: Cathenanline, a Central Intermediate in the Cell Free Biosynthesis of Ajmalicine and Related Indole Alkaloids. J.C.S. Chem. Commun. 1977, 164.

    Google Scholar 

  181. Stöckigt, J., and M.H. Zenk: Strictosidine (Isovincoside): the Key Intermediate in the Biosynthesis of Monoterpenoid Indole Alkaloids. J.C.S. Chem. Commun. 1977, 646.

    Google Scholar 

  182. Rüffer, M., N. Nagakura, and M.H. Zenk: Strictosidine, the Common Precursor for Monoterpenoid Indole Alkaloids with 3a and 3ß Configuration. Tetrahedron Letters 1978, 1593.

    Google Scholar 

  183. Nagakura, N., M. Rüffer, and M.H. Zenk: The Biosynthesis of Monoterpenoid Indole Alkaloids from Strictosidine. J. Chem. Soc., Perkin I 1979, 2308.

    Google Scholar 

  184. Heckendorf, A.H., and C.R. Hutchinson: Biosynthesis of Camptothecin. II. Confirmation that Isovincoside, not Vincoside, is the Penultimate Biosynthetic Precursor of Indole Alkaloids. Tetrahedron Letters 1977, 4153.

    Google Scholar 

  185. Scott, A.I., S.L. Lee, P. de Capile, M.G. Culver, and C.R. Hutchinson: The Role of Isovincoside (Strictosidine) in the Biosynthesis of the Indole Alkaloids. Heterocycles 7, 979 (1977).

    Article  CAS  Google Scholar 

  186. Brown, R.T., J. Leonard, and S.K. Sleigh: The Role of Strictosidine in Monoterpenoid Indole Alkaloid Biosynthesis. Phytochem. 17, 899 (1978).

    Article  CAS  Google Scholar 

  187. Roberts, P.J., N.W. Isaacs, F.H. Allen, W.D.S. Motherwell, and O. Kennard: The Crystal Structure and Absolute Configuration of 0,0-Dimethylipecoside. Acta Crystallogr. B 30, 133 (1974).

    Google Scholar 

  188. Battersby, A.R., and B. Gregory: Biosynthesis of the Ipecac Alkaloids and of Ipecoside, a Cleaved Cyclopentane Monoterpene. Chem. Commun. 1968, 134.

    Google Scholar 

  189. Nagakura, N., G. Höfle, and M.H. Zenk: Deacetylipecoside: the Key Intermediate in the Biosynthesis of the Alkaloids Cephaeline and Emetine. J.C.S. Chem. Commun. 1978, 896.

    Google Scholar 

  190. Nagakura, N., G. Höfle, D. Coggiola, and M.H. Zenk: The Biosynthesis of the Ipecac Alkaloids and of Ipecoside and Alangiside. Planta Med. 34, 381 (1978).

    Article  CAS  Google Scholar 

  191. Inouye, H., Y. Takeda, S. Uesato, K. Uobe, and T. Hashimoto: A Novel Secoiridoid Glucoside, Hydrangenoside A from Hydrangea macrophylla. Tetrahedron Letters 21, 1059 (1980).

    Article  CAS  Google Scholar 

  192. Uesato, S., T. Hashimoto, K. Uobe, and H. Inouye: Novel Type Secoiridoid Glucosides, Hydrangenoside B, C and D from Hydrangea macrophylla. Chem. Pharm. Bull. (Japan) 29, 3421 (1981).

    Article  CAS  Google Scholar 

  193. Uesato, S., Y. Takeda, T. Hashimoto, K. Uobe, H. Inouye, H. Taguchi, and T. Endo: Studies on Monoterpene Glucosides and Related Natural Products. Part 49 Absolute Structures of Hydrangenosides A, B, C, D, E, F and G. Novel Type Secoiridoid Glucosides from Two Hydrangea plants. Helv. Chim. Acta 67, 2111 (1984).

    Article  CAS  Google Scholar 

  194. Uesato, S., T. Hashimoto, Y. Takeda, and H. Inouye: New Secoiridoid Glucosides, Hydrangenosides E, F and G from Hydrangea scandens. Chem. Pharm. Bull. (Japan) 30, 4222 (1982).

    Article  CAS  Google Scholar 

  195. Bate-Smith, E.C., and T. Swain: The Asperulosides and the Aucubins, p. 159 in Comparative Phytochemistry. (Ed. by T. SwAix.) New York: Academic Press. 1966.

    Google Scholar 

  196. Hegnauer, R.: Aucubinartige Glucoside. Über ihre Verbreitung und Bedeutung als systematisches Merkmal. Pharmaceutica Acta Helvetiae 41, 577 (1966).

    CAS  Google Scholar 

  197. Wiffering, J.H.: Aucubinartige Glucoside (Pseudoindikane) und verwandte Hetero-side als systematische Merkmale. Phytochem. 5, 1053 (1966).

    Article  Google Scholar 

  198. Fikenscher, L.H., R. Hegnauer, and H.W. Rujigrok: Iridoide Pflanzenstoffe (Pseudoindikane) als systematische Merkmale. Pharm. Weekblad 104, 561 (1969).

    CAS  Google Scholar 

  199. Kooiman, P.: The Occurrence of Asperulosidic Glycosides in the Rubiaceae. Acta Bot. Neerl. 18, 124 (1969).

    CAS  Google Scholar 

  200. Kooiman, P.: The Occurrence of Iridoid Glycosides in the Scrophulariaceae. Acta Bot. Neerl. 19, 329 (1970).

    Google Scholar 

  201. Hegnauer, R.: Pflanzenstoffe und Pflanzensystematik. Naturwissenschaften 58, 585 (1971).

    Article  CAS  Google Scholar 

  202. Bateshnth, E.C.: Chemistry and Phylogeny of the Angiosperms. Nature 236, 353 (1972).

    Article  Google Scholar 

  203. Grayer-Barkmeuer, R.J.: A Chemosystematic Study of Veronica: Iridoid Glucosides. Biochemical Systematics and Ecology 1, 101 (1973).

    Article  Google Scholar 

  204. Bate-Smith, E.C., I.K. Ferguson, K.H. Hutson, S.R. Jensen, B J Nielsen, and T. Swain: Phytochemical Interrelationship in the Comaceae. Biochemical Systematics and Ecology 3, 79 (1975).

    Article  CAS  Google Scholar 

  205. Hegnauer, R., and P. Kooimaan: Die Systematische Bedeutung von Iridoiden Inhaltsstoffen im Rahmen von Wettstein’s Tubiflorae. Planta Med. 33, 1 (1978).

    Article  CAS  Google Scholar 

  206. Inouye, H., Y. Takeda, S. Kanomi, and T. Okuda: unpublished results.

    Google Scholar 

  207. Tanahashi, T., N. Nagakura, H. Inouye, and M.H. Zenk: Radioimmunoassay for the Determination of Loganin and the Biotransformation of Loganin to Secologanin by Plant Cell Cultures. Phytochem. 23, 1917 (1984).

    Article  CAS  Google Scholar 

  208. Inouye, H., K. Inoue, and M. Ono: unpublished results.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Faculty of Pharmaceutical Sciences, Kyoto University, Sakyo-ku, Kyoto 606, Japan

    H. Inouye & S. Uesato

Authors
  1. H. Inouye
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. S. Uesato
    View author publications

    You can also search for this author in PubMed Google Scholar

Editor information

Editors and Affiliations

  1. Department of Chemistry, The Florida State University, Tallahassee, Florida, USA

    W. Herz (Professor of Chemistry) (Professor of Chemistry)

  2. Biologisches Institut II, Lehrstuhl für Biochemie der Pflanzen, Albert-Ludwigs-Universität, Freiburg i. Br., Federal Republic of Germany

    H. Grisebach

  3. Chemistry Department, The University, Glasgow, Scotland

    G. W. Kirby Sc. D. (Regius Professor of Chemistry) (Regius Professor of Chemistry)

  4. Institut für Organische Chemie, Universität Basel, Basel, Switzerland

    Ch. Tamm

Rights and permissions

Reprints and permissions

Copyright information

© 1986 Springer-Verlag/Wien

About this chapter

Cite this chapter

Inouye, H., Uesato, S. (1986). Biosynthesis of Iridoids and Secoiridoids. In: Herz, W., Grisebach, H., Kirby, G.W., Tamm, C. (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 50. Springer, Vienna. https://doi.org/10.1007/978-3-7091-8888-0_5

Download citation

  • DOI: https://doi.org/10.1007/978-3-7091-8888-0_5

  • Publisher Name: Springer, Vienna

  • Print ISBN: 978-3-7091-8890-3

  • Online ISBN: 978-3-7091-8888-0

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics

Search

Navigation