Skip to main content

Metabolic (Catabolic) Modifications of Alkaloids by Plants

  • Chapter

Abstract

The study of alkaloid biosynthesis has been a major effort of natural products chemists, biochemists, and pharmaceutical chemists during the past several decades. Alkaloid catabolism studies have been a minor effort of a small group of scientists, some of whom are oriented primarily toward botany or plant physiology. As Robinson (1974) states, “Alkaloids appear to be active metabolites, but their usefulness to plants remains obscure.” It is incorrect to conclude that the problem of metabolism has been solved merely because the routes of biosynthesis have been described; the other half of the problem is what happens to the alkaloid after it is synthesized. Catabolic reactions of some alkaloids have been studied using microorganisms (especially soil microorganisms), and biochemical pharmacology has yielded data on modifications of alkaloids which may be interpreted as detoxification processes in animals. Altschul (1970, 1973) recently completed a study of 2.5 million specimens of flowering1 plants that have been described as restorative of health, according to medicinal folklore. Altschul (1970) and Schultes (1975a,b) indicate that many species offer, somewhat vaguely, hope for relief of cancer, heart disease, mental illness, and diverse metabolic disorders, but these authors have not yet explored the plants influencing the function and diseases of the reproductive tract of the human female.

This chapter was written by George R. Waller, L. Skursky of the University of J. E. Purkijne, Brno, Czechoslovakia, and T. M. Heinze of the Medical Research Foundation, Oklahoma City, Oklahoma.

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

Buying options

Chapter
USD   29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD   84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD   109.99
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

Learn about institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  • Aldercreutz, H., Tikkamen, M. J., and Humerman, D. H. (1974) J. Steroid Biochem. 5, 211.

    Article  Google Scholar 

  • Altschul, S. von Reis, Bot. Mus. Leaflets (Harvard) (1970) 22(10), 337–343.

    Google Scholar 

  • Altschul, S. von Reis (1973) Drugs & Foods from Little Known Plants, Harvard Univ. Press, Cambridge, Mass.

    Google Scholar 

  • Alworth, W. L., and Rapoport, H. (1965) Arch. Biochem. Biophys. 112, 45.

    Article  PubMed  CAS  Google Scholar 

  • Alworth, W. L., Lieberman, L., and Ruckstahl, J. A. (1969) Phytochemistry 8, 1427.

    Article  CAS  Google Scholar 

  • Ames, B. (1975) personal communication.

    Google Scholar 

  • Antoun, M. D., and Roberts, M. F. (1975a) Planta Med. 28, 6.

    Article  PubMed  CAS  Google Scholar 

  • Antoun, M. D., and Roberts, M. F. (1975b) Phytochemistry 14, 907.

    Google Scholar 

  • Antoun, M. D., and Roberts, M. F. (1975c) Phytochemistry 14, 1275.

    Article  CAS  Google Scholar 

  • Arcamone, F., Chain, E. B., Ferretti, A., Minghetti, A., Pennella, P., and Tonolo, A. (1962) Biochim. Biophys. Acta 57, 174.

    Article  PubMed  CAS  Google Scholar 

  • Axelrod, J., and Reichenthal, J. J. (1953) J. Pharm. Exp. Ther. 107, 519.

    CAS  Google Scholar 

  • Barton, D. H. R., Kirby, G. W., Steglich, W., Thomas, G. M., Battersby, A. R., Dabson, T. A., and Ramsey, H. (1965) J. Chem. Soc. 1965, 2423.

    Google Scholar 

  • Battersby, A. R., Foulkes, D. M., and Binks, R. (1965) J. Chem. Soc. 1965, 3323.

    Google Scholar 

  • Baumann, T. W., and Wanner, H. (1972) Planta 108, 11–19.

    Article  CAS  Google Scholar 

  • Beaudin-Dufour, D., and Muller, L. E. (1971) Turrialba (Costa Rica) 21(4), 387–392.

    CAS  Google Scholar 

  • Bertrand, G. (1905) C. R. Acad. Sci. 141, 209.

    CAS  Google Scholar 

  • Birecka, H., and Zebrowska, J. (1960) Bull. Acad. Polon. Sci. Ser. Sci. Biol. 8, 339. Chem. Abstr. 55, 697h.

    CAS  Google Scholar 

  • Boecklin, G. E. (1975) Tea and Coffee Trade J. 147, 32–33.

    Google Scholar 

  • Brady, L. R., and Tyler, V. E., Jr. (1958) Plant Physiol. 33, 334.

    Article  PubMed  CAS  Google Scholar 

  • Bu’Lock, J. D. (1965) The Biosynthesis of Natural Products, McGraw-Hill Book Co., New York, pp. 81–82.

    Google Scholar 

  • Burg, A. W. (1976) Drug Metab. Rev. 4, 199–228.

    Article  Google Scholar 

  • Burlingame, A. L., Cox, R. E., and Derrick, P. (1974) Anal. Chem. 46, 248.

    Article  Google Scholar 

  • Chandler, J. L. R., and Gholson, R. K. (1972) Phytochemistiy 11, 239–242.

    Article  CAS  Google Scholar 

  • Chevalier, A. (1937) Rev. Bot. Appl. Agric. Tropicale 17, 821.

    Google Scholar 

  • Clautriau, G. (1892) Bull. Soc. Belge. Microsc. 18, 80 cited in James (1950).

    Google Scholar 

  • Coscia, C. J. (1976) personal communication.

    Google Scholar 

  • Crafts, A. S. (1961) Translocation in Plants, Holt, Rinehart, and Winston, New York.

    Google Scholar 

  • Cromwell, B. T. (1933) Biochem. J. 27, 860.

    PubMed  CAS  Google Scholar 

  • Daddona, P. E., and Hutchinson, C. R. (1976) Phytochemistry 15, 941–945.

    Article  CAS  Google Scholar 

  • Dawber, R. T. (1976) Z. Ernährungwiss. 15, 52–53.

    Article  CAS  Google Scholar 

  • Dawber, T., Kannel, W., and Gordon, T. (1974) New England J. Med. 291, 871–874.

    Article  CAS  Google Scholar 

  • Dawson, R. F. (1948) Adv. Enzymol. 8, 203.

    CAS  Google Scholar 

  • Dawson, R. F. (1951) J. Am. Chem. Soc, 73, 4218.

    Article  CAS  Google Scholar 

  • Dawson, R. F. (1952) Am. J. Bot., 39, 250.

    Article  CAS  Google Scholar 

  • Dawson, R. F., and Osdene, T. J. (1972) Rec. Adv. Phytochem. 5, 317–338.

    CAS  Google Scholar 

  • Dawson, R. F., Christman, D. R., D’Adamo, A., Solt, M. L., and Wolf, A. D. (1960) J. Am. Chem. Soc. 82, 2628.

    Article  CAS  Google Scholar 

  • Dempewolff, R. F. (1975) Sei. Dig. 77, 31–36.

    Google Scholar 

  • Dickenson, P. B., and Fairbairn, J. W. (1975) Ann. Bot. (London) 39, 707–712.

    Google Scholar 

  • Dietrich, S. M. C., and Martin, R. O. (1969) Biochemistry 8, 4163.

    Article  PubMed  CAS  Google Scholar 

  • Digenis, G. A. (1969) J. Pharm. Sci. 58, 39.

    Article  PubMed  CAS  Google Scholar 

  • Digenis, G. A., Faraj, B. A., and Abou-Charr, C. I. (1966) Biochem. J. 101, 27c.

    PubMed  CAS  Google Scholar 

  • Ebbighouser, O. R., Mowat, J. M., Stearns, H., and Vestergaard, P. (1975) Biochem. Mass Spectrom. 1, 305.

    Article  Google Scholar 

  • Eberspaecher, F., Uesseler, H., and Lingens, F. (1970) Hoppe-Seyl. Z. Physiol. Chem. 351, 1465.

    Article  CAS  Google Scholar 

  • Egri, L. (1957) Fachliche Mitt. Oesterr. Tabakreg. 19 (CA 51, 18490) (cited by Stepka and Dewey, 1963)

    Google Scholar 

  • El-Hamidi, A., and Wanner, H. (1964) Planta 61, 90–96.

    Article  Google Scholar 

  • Fairbairn, J. W. (1965) in Beiträge zur Biochemie und Physiologie von Naturstoffen: Festschrift: Kurt Mothes zum 65 Geburtstag, Jena, VEB Gustav Fischer Verlag, p. 113.

    Google Scholar 

  • Fairbairn, J. W., and Ali, A. A. E. R. (1968a) Phytochemistry 7, 1593.

    Article  CAS  Google Scholar 

  • Fairbairn, J. W., and Ali, A. A. E. R. (1968b) Phytochemistry 7, 1599.

    Article  CAS  Google Scholar 

  • Fairbairn, J. W., and Challen, S. B. (1959) Biochem. J. 72, 556.

    PubMed  CAS  Google Scholar 

  • Fairbairn, J. W., and El-Masry, S. (1967) Phytochemistry 6, 499.

    Article  CAS  Google Scholar 

  • Fairbairn, J. W., and El-Masry, S. (1968) Phytochemistry 7, 181.

    Article  CAS  Google Scholar 

  • Fairbairn, J. W., and Paterson, A. (1966) Nature 210, 1163.

    Article  PubMed  CAS  Google Scholar 

  • Fairbairn, J. W., and Suwal, P. N. (1961) Phytochemistry 1, 38.

    Article  CAS  Google Scholar 

  • Fairbairn, J. W., and Wassel, G. (1964) Phytochemistry 3, 253.

    Article  CAS  Google Scholar 

  • Fairbairn, J. W., and Wassel, G. (1965) Phytochemistry 3, 583.

    Article  Google Scholar 

  • Fairbairn, J. W., and Wassel, G. M. (1967) J. Chem. U. A. R. 10, 275.

    CAS  Google Scholar 

  • Fairbairn, J. W., Paterson, A., and Wassel, G. (1964) Phytochemistry 3, 577.

    Article  CAS  Google Scholar 

  • Fairbairn, J. W., Djote, M., and Paterson, A. (1968a) Phytochemistry 7, 2111.

    Article  CAS  Google Scholar 

  • Fairbairn, J. W., Palmer, J. M., and Paterson, A. (1968b) Phytochemistry 7, 2117.

    Article  CAS  Google Scholar 

  • Fairbairn, J. W., Hakim, F., and Dickenson, P. B. (1973) J. Pharm. Pharmac. 25, 113P suppl.

    Google Scholar 

  • Fairbairn, J. W., Hakim, F., and El Kheir, Y. (1974) Phytochemistry 13, 1133–1139.

    Article  CAS  Google Scholar 

  • Fairbairn, J. W., and Steele, M. (1977) personal communication.

    Google Scholar 

  • Floss, H. G., Robbers, J. E., and Heinstein, K. F. (1974) Rec. Adv. Phytochem. 8, 141–178.

    CAS  Google Scholar 

  • Fodor, G. (1976) Spec. Period. Rep. (Chem. Soc. of London) 6, 65.

    CAS  Google Scholar 

  • Frank, A. W., and Marion, L. (1956) Can. J. Chem. 34, 1641.

    Article  CAS  Google Scholar 

  • Friedman, G. D., Siegelaub, A. B., and Seltzer, C. C. (1974) New Engl. J. Med. 290, 469–473.

    Article  PubMed  CAS  Google Scholar 

  • Frost, G. M., Yang, K. S., and Waller, G. R. (1967) J. Biol. Chem. 242, 887.

    PubMed  CAS  Google Scholar 

  • Gentry, C. E. (1968) Interrelationship of Rhizoctonia solani Kuehn, Environment, and Genotype on the Alkaloid Content of Tall Fescue, Festuca arundinacea Schrebs, Ph.D. Thesis, Univ. of Kentucky.

    Google Scholar 

  • Gholson, R. K. (1966) Nature 212, 933.

    Article  CAS  Google Scholar 

  • Gholson, R. K., and Kori, J. (1964) J. Biol. Chem. 239, 2399.

    Google Scholar 

  • Gholson, R. K., Ueda, I., Ogasawara, N., and Henderson, L. M. (1964) J. Biol. Chem. 239, 1208.

    PubMed  CAS  Google Scholar 

  • Gholson, R. K., Sakakibara, S. and Wicks, F. D. (1976) American Society for Microbiology 76th Annual Meeting, Atlantic City, N.J., May 2–7, Session 72.

    Google Scholar 

  • Griffith, G. D., and Griffith, T. (1964) Plant Physiol. 39, 970.

    Article  PubMed  CAS  Google Scholar 

  • Griffith, G. D., Griffith, T., and Byerrum, R. (1960) J. Biol. Chem. 235, 3536.

    PubMed  CAS  Google Scholar 

  • Gross, D., Lehmann, H., and Schuette, H. R. (1970) Z. Pflanzenphysiol. 63, 1.

    CAS  Google Scholar 

  • Gruetzmann, K. D. and Schroeter, H. B. (1966) in Abh. Dtsch. Akad. Wiss., Kl., Chem. Geol. Biol. Berlin; 3. Internationales Symposium Biochemie und Physiologie der Alkaloide, Halle (Saale) Germany, June, 1965, p. 347.

    Google Scholar 

  • Heftmann, E., and Schwimmer, S. (1972) Phytochemistry 11, 2783.

    Article  CAS  Google Scholar 

  • Heinstein, P. F., Lee, S. L., and Floss, H. G. (1971) Biochem. Biophys. Res. Commun. 44, 1244.

    Article  PubMed  CAS  Google Scholar 

  • Hennekins, C. H., Drolette, M. E., Jessee, M. J., Daves, J. E., and Hutchinson, G. B. (1976) New Engl. J. Med. 294, 633–636.

    Article  Google Scholar 

  • Herndlhofer, E. (1933), Boletim de Agricultura (Brasil) 34, 163–251.

    Google Scholar 

  • Hiles, R. A., and Byerrum, R. U. (1969) Phytochemistry 8, 1927.

    Article  CAS  Google Scholar 

  • Ill’in, G. S. (1965) Pharmazie 20, 724.

    Google Scholar 

  • Ill’in, G. S. (1966) in Abh. Dtsch. Akad. Wiss., Kl., Chem. Geol. Biol., Berlin; 3. Internationales Symposium Biochemie und Physiologie der Alkaloide, June, 1965, Halle (Saale) Germany, p. 347.

    Google Scholar 

  • Ill’in, G. S., and Lovkova, M. Ja. (1972) in Abh. Dtsch. Akad. Wiss., Kl., Chem. Geol. Biol., Berlin; 4. Internationales Symposium Biochemie und Physiologie der Alkaloide, June, 1965, Halle (Saale) Germany, pp. 207-208.

    Google Scholar 

  • Ill’in, G. S., and Lovkova, M. Ja. (1966) Biokhimyia 31, 174.

    Google Scholar 

  • Ill’in, G. S., and Serebrovskaya, K. B. (1958) Dokl. Akad. Nauk SSSR 118, 139. Chem. Abstr. 52, 8293h.

    Google Scholar 

  • Ill’in, G. S., Lovkova, M. Ya., and Klimentjeva, N. I. (1968) Izv. Akad. Nauk. SSSR Ser. Biol. 1968, 871.

    Google Scholar 

  • Imsande, J. (1961) J. Biol. Chem. 236, 1494.

    PubMed  CAS  Google Scholar 

  • James, W. O. (1950) “Alkaloids in the plant” in The Alkaloids (R. H. F. Manske and H. L. Holmes, eds.), Vol. I, Academic Press, New York, p. 15.

    Google Scholar 

  • James, W. O. (1953) Endeavour 12, 76.

    CAS  Google Scholar 

  • Jick, H., Miettinen, O. S., Neff, R. K., Shapiro, S., Heinonen, O. P., and Slone, P. (1973) New Engl. J. Med. 289, 63–67.

    Article  PubMed  CAS  Google Scholar 

  • Jindra, A., Cihak, A., and Kovacs, P. (1964) Collect. Czech. Chem. Commun. 29, 1059.

    CAS  Google Scholar 

  • Johnson, R. D., and Waller, G. R. (1974) Phytochemistry 13, 1493–1500.

    Article  CAS  Google Scholar 

  • Joshi, J. G., and Handler, P. (1960) J. Biol. Chem. 235, 2981.

    PubMed  CAS  Google Scholar 

  • Joshi, J. G., and Handler, P. (1962) J. Biol. Chem. 237, 929, 3185.

    PubMed  CAS  Google Scholar 

  • Kahn, Y., and Blum, J. J. (1968) J. Biol. Chem. 243, 1448.

    PubMed  CAS  Google Scholar 

  • Kalberer, P. (1964) Ber. Schweiz. Bot. Ges. 74, 62.

    CAS  Google Scholar 

  • Kalberer, P. (1965) Nature 205, 597.

    Article  CAS  Google Scholar 

  • Kannel, W. B., and Dawber, T. R. (1973) New Engl. J. Med. 289, 100–101.

    Article  PubMed  CAS  Google Scholar 

  • Kaplan, N. O. (1961) in Metabolic Pathways (D. M. Greenberg, ed.), Academic Press, New York, Vol. 2, p. 627.

    Google Scholar 

  • Keller, J., Liersch, M., and Grunicke, D. (1971) Eur. J. Biochem. 22, 263.

    Article  PubMed  CAS  Google Scholar 

  • Keller, H., Wanner, H., and Baumann, T. W. (1972) Planta 108, 339–350.

    Article  CAS  Google Scholar 

  • Kirby, G. W., Mossey, S. R., and Steinreich, D. (1972) J. Chem. Soc, Perkin Trans. I, 1642.

    Google Scholar 

  • Kisaki, T., and Tamaki, E. (1961a) Arch. Biochem. Biophys. 92, 351.

    Article  PubMed  CAS  Google Scholar 

  • Kisaki, T., and Tamaki, E. (1961b) Arch. Biochem. Biophys. 94, 252.

    Article  PubMed  CAS  Google Scholar 

  • Kisaki, T., and Tamaki, E. (1964a) Nippon Nogei Kagaku Kaishi 38, 549; Chem. Abstr. 63, 7059b.

    Article  CAS  Google Scholar 

  • Kisaki, T., and Tamaki, E. (1964b) Nippon Nogei Kagaku Kaishi 38, 392; Chem. Abstr. 63, 3325h.

    Article  CAS  Google Scholar 

  • Kisaki, T., and Tamaki, E. (1964c) Agr. Biol. Chem. 28, 492.

    Article  CAS  Google Scholar 

  • Kisaki, T., and Tamaki, E. (1966) Phytochemistry 11, 965–973.

    Google Scholar 

  • Klatsky, A. L., Friedman, G. D., and Siegelaub, A. B., (1973) J. Am. Med. Assoc. 226, 540.

    Article  CAS  Google Scholar 

  • Lee, H. J., and Waller, G. R. (1972a) Phytochemistry 11, 965–973.

    Article  CAS  Google Scholar 

  • Lee, H. J., and Waller, G. R. (1972b) Phytochemistry 11, 2233–2240.

    Article  CAS  Google Scholar 

  • Lee, M. G., and Millard, B. J. (1975) Biochem. Mass Spectrom. 2, 78.

    Article  CAS  Google Scholar 

  • Leete, E., (1968) Tetrahedron Lett. 1968, 4433.

    Google Scholar 

  • Leete, E. (1969) Adv. Enzymol. 32, 373.

    PubMed  CAS  Google Scholar 

  • Leete, E. (1973) in First Philip Morris Science Symposium Proceedings, p. 92.

    Google Scholar 

  • Leete, E. (1974) Phytochemistry 14, 471–474.

    Article  Google Scholar 

  • Leete, E., and Bell, V. M. (1959) J. Am. Chem. Soc. 81, 4358.

    Article  CAS  Google Scholar 

  • Leete, E., and Chedekel, M. R. (1974) Phytochemistry 14, 1853–1859.

    Article  Google Scholar 

  • Lingens, F. (1972) in Abh. Dtsch. Akad. Wiss. Kl., Chem. Geol. Biol., Berlin;4. Internationales Symposium Biochemie und Physiologie der Alkaloide, June, 1969, Halle (Saale) Germany, pp. 65-73.

    Google Scholar 

  • Lingens, F., Goebel, W., and Uesseler, H. (1967) Eur. J. Biochem. 2, 442.

    Article  PubMed  CAS  Google Scholar 

  • Looser, E., Baumann, T. W., and Wanner, H. (1974) Phytochemistry 13, 2515–2518.

    Article  CAS  Google Scholar 

  • Lovkova, M. Ya. (1964) Acta Biol. Acad. Sci. Hung. 14, 273.

    PubMed  CAS  Google Scholar 

  • Lovkova, M. Ya., Ill’in, G. S., and Minozhedinova, N. S. (1973) Prikl. Biokhim. Mikrobiol. 9, 595–598. Chem. Abstr. 79, 133282.

    PubMed  CAS  Google Scholar 

  • Luckner, M. (1972) Secondary Metabolism in Plants and Animals (T. N. Vasudevan, tr.), Academic Press, New York, p. 212.

    Google Scholar 

  • Madyastha, K. M., Guarnaccia, R., Baxter, C., and Coscia, C. J. (1973) J. Biol. Chem. 248, 2497.

    PubMed  CAS  Google Scholar 

  • Madyastha, K. M., Meehan, T. D., and Coscia, C. J. (1976) Biochemistry 15, 1097.

    Article  PubMed  CAS  Google Scholar 

  • Madyastha, K.M., Ridgway, J. E., Dwyer, J. G., and Coscia, C. J. (1977) Abs. 1st Int. Congress on Cell Biology, Sept. 5–10, Boston, Mass., published in J. Cell. Biol. 316, 272.

    Google Scholar 

  • Mann, D. F., and Byerrum, R. V. (1974a) J. Biol. Chem. 249, 6817–6823.

    PubMed  CAS  Google Scholar 

  • Mann, D. F., and Byerrum, R. V. (1974b) Plant Physiol. 53, 603–609.

    Article  PubMed  CAS  Google Scholar 

  • McCann, J., Choi, E., Yamasaki, S. D., and Ames, B. N. (1975) Proc. Natl. Acad. Sci. 72, 5135–5190 and references cited.

    Article  PubMed  CAS  Google Scholar 

  • McFarlane, J., Madyastha, K. M., and Coscia, C. J. (1975) Biochem. Biophys. Res. Commun. 66, 1263.

    Article  PubMed  CAS  Google Scholar 

  • Meehan, T. D., and Coscia, C. J. (1973) Biochem. Biophys. Res. Commun. 53, 1043.

    Article  PubMed  CAS  Google Scholar 

  • Melo, M., Carvalho, A., and Monaco, L. C. (1975) in Congresso da Sociedade Brasileiro paro o Progresso da Ciência, 27°, Reuniāo, Secāo 281.

    Google Scholar 

  • Merker, J., and Pyriki, C. (1966) in Abh. Dtsch. Akad. Wiss. Kl., Chem. Geol. Biol., Berlin; 3. Internationales Symposium Biochemie und Physiologie der Alkaloide, June, 1965, Halle (Saale) Germany, p. 173.

    Google Scholar 

  • Miller, K. J., Jolies, C., and Rapoport, H. (1973) Phytochemistry 12, 597.

    Article  CAS  Google Scholar 

  • Mizusaki, S., Kisaki, T., and Tamaki, E. (1968) Plant Physiol. 43, 93.

    Article  PubMed  CAS  Google Scholar 

  • Mizusaki, S., Tanabe, Y., Noguchi, M., and Tamaki, E. (1971) Plant Cell Physiol. 12, 633.

    CAS  Google Scholar 

  • Mizusaki, S., Tanabe, Y., Noguchi, M., and Tamaki, E. (1972) Phytochemistry 11, 2757.

    Article  CAS  Google Scholar 

  • Mizusaki, S., Tanabe, Y., Noguchi, M., and Tamaki, E. (1973) Plant Cell Physiol. 14, 103–110.

    CAS  Google Scholar 

  • Mothes, K. (1928) Planta 5, 563.

    Article  CAS  Google Scholar 

  • Mothes, K. (1965) Naturwissenschaften 52, 571.

    Article  CAS  Google Scholar 

  • Mothes, K. (1966) in Abh. Dtsch. Akad. Wiss. Kl., Chem. Geol. Biol., Berlin; 3. Internationales Symposium Biochemie und Physiologie der Alkaloide, June, 1965, Halle (Saale) Germany, p. 27.

    Google Scholar 

  • Mothes, K. (1975) Rec. Adv. Phytochem. 10, 385–405.

    Google Scholar 

  • Mothes, K., and Schuette, H. R. (1969) Biosynthese der Alkaloide, VEB Deutscher Verlag der Wissenschaften, Berlin.

    Google Scholar 

  • Mothes, K., Engelbrecht, L., Tschoepe, K. H., and Hutschenreuter-Trefftz, G. (1957) Flora (Jena) 144, 518.

    Google Scholar 

  • Mothes, K. Richter, I., Stolle, D., and Groeger, D. (1965) Naturwissenschaften 52, 431.

    Article  CAS  Google Scholar 

  • Mudzhiri, K. S. (1955) Sbornik Trudov Tbilisi Nauch.-Issledovatel. Khim. Farm. Inst. 7, 19–38 (Chem. Abstr. 54, 13286).

    CAS  Google Scholar 

  • Neumann, D., and Tschoepe, K. H. (1966) Flora (Jena) Abt. A 156, 521.

    CAS  Google Scholar 

  • Newell, J., and Waller, G. R., Proc. Okla. Acad. Sci. 45, 143 (1965).

    CAS  Google Scholar 

  • Nowacki, E. K., and Waller, G. R. (1973) Z. Pflanzenphysiol. 69, 228–291.

    CAS  Google Scholar 

  • Nowacki, E. K., and Waller, G. R. (1975a) Phytochemistry 14, 161–164.

    Article  CAS  Google Scholar 

  • Nowacki, E. K., and Waller, G. R. (1975b) Phytochemistry 14, 165–171.

    Article  CAS  Google Scholar 

  • O’Donovan, D., and Leete, E. (1963) J. Am. Chem. Soc. 85, 461.

    Article  Google Scholar 

  • Ogutuga, D. B. A., and Northcote, D. H. (1970) Biochem. J. 117, 715–720.

    PubMed  CAS  Google Scholar 

  • Petrack, B., Greengard, P., Craston, A., and Kalinsky, H. J. (1963) Biochem. Biophys. Res. Commun. 13, 472.

    Article  CAS  Google Scholar 

  • Phillipson, D. J., Handa, S. S., and El-Dabbas, S. W. (1976) Phytochemistry 15, 1297–1301.

    Article  CAS  Google Scholar 

  • Pöhm, M. (1966) in Abh. Dtsch. Akad. Wiss. Kl., Chem. Geol. Biol., Berlin; 3. Internationales Symposium Biochemie und Physiologie der Alkaloide, June, 1965, Halle (Salle) Germany. p. 251.

    Google Scholar 

  • Preiss, J., and Handler, P. (1958) J. Biol. Chem. 233, 493.

    PubMed  CAS  Google Scholar 

  • Ramstad, E., and Agurell, S. (1964) Ann. Rev. Plant Physiol. 15, 143.

    Article  CAS  Google Scholar 

  • Rapoport, H. (1966) Abh. Dtsch. Akad. Wiss. Kl., Chem. Geol. Biol., Berlin;3. Internationales Symposium Biochemie und Physiologie der Alkaloides, June, 1965, Halle (Saale) Germany, p. 111.

    Google Scholar 

  • Ridgway, J. E., and Coscia, C. J. (1976) personal communication.

    Google Scholar 

  • Robbers, J. E., and Floss, H. G. (1970) J. Pharm. Sci. 59, 702.

    Article  PubMed  CAS  Google Scholar 

  • Roberts, M. F. (1971) Phytochemistry 10, 3021.

    Article  CAS  Google Scholar 

  • Roberts, M. F. (1974) Phytochemistry 13, 119.

    Article  CAS  Google Scholar 

  • Roberts, M. F. (1975) Phytochemistry 14, 2393.

    Article  CAS  Google Scholar 

  • Robinson, T. (1971) personal communication.

    Google Scholar 

  • Robinson, T. (1974) Science 184, 430–435.

    Article  PubMed  CAS  Google Scholar 

  • Roddick, J. G. (1976) Phytochemistry 15, 475.

    Article  CAS  Google Scholar 

  • Romeike, A. (1962) Naturwissenschaften 18, 426.

    Article  Google Scholar 

  • Romeike, A. (1964) Flora (Jena) 154, 163.

    CAS  Google Scholar 

  • Ryrie, I. J., and Scott, K. J. (1969) Biochem. J. 115, 679.

    PubMed  CAS  Google Scholar 

  • Sadykov, A. S., Aslanov, Kh. A., and Kushmuradov, Yu. K. (1975) Quinolizidine Alkaloids, Science Publishing House, Moscow.

    Google Scholar 

  • Sander, H. (1956) Planta 47, 374.

    Article  CAS  Google Scholar 

  • Sanders, H. J. (1969) Chem. Eng. News 47(21) (May 19) 54–68.

    Article  Google Scholar 

  • Sárkány, S. (1962) Magy. Tud. Akad. Biol. 5, 93–107.

    Google Scholar 

  • Sárkány, S., Sárkány-Kiss, J., and Varzar-Petri, G. (1966) in Abh. Dtsch. Akad. Wiss. Kl., Chem. Geol. Biol., Berlin; 3. Internationales Symposium Biochemie und Physiologie der Alkaloide, June, 1965, Halle (Saale) Germany, pp. 355-361.

    Google Scholar 

  • Sárkány, S., and Dános, B. (1958) Acta Bot. Acad. Sci. Hung. 3, 293. Chem. Abstr. 52, 1030b.

    Google Scholar 

  • Sastry, S. D. (1972) in Biochemical Applications of Mass Spectrometry (George R. Waller, ed.), Wiley-Interscience, New York, pp. 665–709.

    Google Scholar 

  • Sastry, S. D., and Waller, G. R. (1972) Phytochemistry 11, 2241–2745.

    Article  CAS  Google Scholar 

  • Schroeter, H. B. (1958) in 2nd International Science Tobacco Congress (Brussels), p. 426; Biol. Abstr. (1960) 35, 35736.

    Google Scholar 

  • Schroeter, H. B. (1966) in Abh. Dtsch. Akad. Wiss. Kl., Chem. Geol. Biol., Berlin; 3. Internationales Symposium Biochemie und Physiologie der Alkaloide, June, 1965, Halle (Saale) Germany, p. 157.

    Google Scholar 

  • Schuette, H. R. (1969) in Biochemie der Alkaloide (K. Mothes and H. R. Schuette, eds.), VEB Deutscher Verlag der Wissenschaften, Berlin, p. 240.

    Google Scholar 

  • Schultes, R. E. (1975) Rec. Adv. Phytochem. 9, 1.

    Article  CAS  Google Scholar 

  • Schultes, R. E. (1976) Philip Morris Science Symposium, 2nd, pp. 133-171.

    Google Scholar 

  • Schumauder, H. P., and Groeger, D. (1973) Biochem. Physiol. Pflanz. 164, 41.

    Google Scholar 

  • Scott, A. I. (1970) Acc. Chem. Res. 3, 151.

    Article  CAS  Google Scholar 

  • Scott, A. I. (1974) Science 184, 760–764.

    Article  PubMed  CAS  Google Scholar 

  • Scott, A. I. (1976) Philip Morris Science Symposium, 2nd, pp. 101-132.

    Google Scholar 

  • Scott, A. I., Reichardt, P. B., Slayton, M. B., and Sweeny, J. G. (1962) Bio-organic Chem. 1, 157.

    Google Scholar 

  • Scott, A. I., Reichardt, P. B., Slayton, M. B., and Sweeny, J. G. (1973) Rec. Adv. Phytochem. 6, 117.

    CAS  Google Scholar 

  • Skursky, L., and Waller, G. R., (1972) in Abh. Dtsch. Akad. Wiss. Kl., Chem. Geol. Biol., Berlin; 4. Internationales Symposium Biochemie und Physiologie der Alkaloide, June, 1969, Halle (Saale) Germany, pp. 181-186.

    Google Scholar 

  • Skursky, L., Burleson, D., and Waller, G. R. (1969) J. Biol. Chem. 244, 3238.

    PubMed  CAS  Google Scholar 

  • Solt, M. L., Dawson, R. F., and Christman, D. R. (1960) Plant Physiol. 35, 886.

    Article  Google Scholar 

  • Spencer, R. L., and Preiss, J. (1967) J. BioL Chem. 242, 385.

    PubMed  CAS  Google Scholar 

  • Stagg, F. V., and Millin, D. J. (1975) J. Sci. Food Agric. 26, 1439–1459.

    Article  CAS  Google Scholar 

  • Steinegger, E., and Bernasconi, R. (1964) Pharm. Acta Helv. 39, 480.

    PubMed  CAS  Google Scholar 

  • Stepka, W., and Dewey, L. J. (1961) Plant Physiol. 36, 592.

    Article  PubMed  CAS  Google Scholar 

  • Stepka, W., and Dewey, L. J. (1963) Plant Physiol. 38, 283.

    Google Scholar 

  • Stermitz, F. R., and Rapoport, H. (1961) J. Am. Chem. Soc. 83, 4045.

    Article  CAS  Google Scholar 

  • Suzuki, T., and Takahashi, E. (1976) Phytochemistry 15, 1235–1239.

    Article  CAS  Google Scholar 

  • Sylvain, P. G. (1976) personal communication.

    Google Scholar 

  • Trigg, C. W. (1922) “The chemistry of the coffee bean” in All About Coffee (W. H. Ukers, ed.), The Tea and Coffee Trade Journal Co., p. 155.

    Google Scholar 

  • Tso, T. C., and Jeffrey, R. N. (1957) Plant Physiol. 32, 86.

    Article  PubMed  CAS  Google Scholar 

  • Tso, T. C., and Jeffrey, R. N. (1959) Arch. Biochem. Biophys. 80, 46.

    Article  CAS  Google Scholar 

  • Tso, T. C., and Jeffrey, R. N. (1961) Arch. Biochem. Biophys. 92, 253.

    Article  PubMed  CAS  Google Scholar 

  • United States Department of Health, Education and Welfare, National Heart Institute (1966) The Framingham Heart Study: Habits and Coronary Heart Disease (PHS Publication No. 1515), US GPO, Washington, D. C.

    Google Scholar 

  • Waller, G. R. (1969) Progr. Chem. Fats Other Lipids 10, 151–238.

    Article  Google Scholar 

  • Waller, G. R., and Lee, J. L-C. (1969) Plant Physiol. 44, 522.

    Article  PubMed  CAS  Google Scholar 

  • Waller, G. R., and Skursky, L. (1972) Plant Physiol. 50, 622.

    Article  PubMed  CAS  Google Scholar 

  • Waller, G. R., Tang, M.S-L., Scott, M. R., Goldberg, F. J., Mayes, J. S., and Auda, H. (1965) Plant Physiol. 40, 803.

    Article  PubMed  CAS  Google Scholar 

  • Waller, G. R., Yang, K. S., Gholson, R. K., Hadwiger, L. A., and Chaykin, S. (1966) J. Biol. Chem. 241, 4411–4418.

    PubMed  CAS  Google Scholar 

  • Waller, G. R., Yang, K. S., Sastry, S. D., Frost, G. F., and Johnson, R. D. (1975) unpublished results.

    Google Scholar 

  • Wanner, H. (1963) in Abh. Dtsch. Akad. Wiss. Kl., Chem. Geol. Biol., Berlin;2. Internationales Symposium Biochemie und Physiologie der Alkaloide, June, 1959, Halle (Saale) Germany, pp. 65-79.

    Google Scholar 

  • Wanner, H., and Kalberer, P. (1966) in Abh. Dtsch. Akad. Wiss. Kl., Chem. Geol. Biol. Berlin; 2. Internationales Symposium Biochemie und Physiologie der Alkaloide, June, 1965, Halle (Saale) Germany, p. 607.

    Google Scholar 

  • Wanner, H., Pešáková, N., Baumann, T. W., Charubala, R., Guggisberg, A., Hesse, M., and Schmid, H. (1975) Phytochemistry 14, 747–750.

    Article  CAS  Google Scholar 

  • Weevers, Th. (1932) Recl. Trav. Bot. Neerl. 30, 336.

    Google Scholar 

  • Wenkert, E. (1954) Experientia 10, 346.

    Article  PubMed  CAS  Google Scholar 

  • Weybrew, J. A. (1975) personal communication.

    Google Scholar 

  • Weybrew, J. A., Mann, T. J., and Moore, E. L. (1960) Tob. Int. NY 151, 15–24.

    Google Scholar 

  • Weybrew, J. A., and Mann, T. J. (1963) Tob. Int. NY. 156, 8–30.

    Google Scholar 

  • Weygand, F., and Floss, H. G. (1963) Angew. Chem. Int. Ed. (Engl.) 2, 243.

    Article  Google Scholar 

  • Willuhn, G. (1966) in Abh. Dtsch. Akad. Wiss. Kl., Chem. Geol. Biol., Berlin; 3. Internationales Symposium Biochemie und Physiologie der Alkaloide, June, 1965, Halle (Saale) Germany, pp. 97-103.

    Google Scholar 

  • Yang, K. S., Gholson, R. K., and Waller, G. R. (1965) J. Am. Chem. Soc. 87, 4184.

    Article  PubMed  CAS  Google Scholar 

  • Yoshida, D. (1962) Plant Cell Physiol. 3, 391.

    CAS  Google Scholar 

  • Yoshida, D. (1971) Hatano Tabako Shikinjo Jokoko 69, 63–68; Chem. Abstr. (1973) 79, 2873.

    Google Scholar 

  • Zielke, H. R., Byerrum, R. U., O’Neal, R. M., Burns, L. C., and Koeppe, R. E. (1968) J. Biol. Chem. 243, 4757.

    PubMed  CAS  Google Scholar 

  • Zsadon, B., and Kaposi, P. (1970) Tetrahedron Lett. 1970, 4615.

    Google Scholar 

  • Zsadon, B., and Kaposi, P. (1972) Acta Chim. Acad. Sci. Hung. 71, 115.

    CAS  Google Scholar 

  • Zsadon, B., and Oha, K. H. (1971) Acta Chim. Acad. Sci. Hung. 69, 87.

    CAS  Google Scholar 

  • Zsadon, B., Oha, K. H., and Tétényi, P. (1975) Acta Chim. Acad. Sci. Hung. 84, 71.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

Copyright information

© 1978 Plenum Press, New York

About this chapter

Cite this chapter

Waller, G.R., Nowacki, E.K. (1978). Metabolic (Catabolic) Modifications of Alkaloids by Plants. In: Alkaloid Biology and Metabolism in Plants. Springer, Boston, MA. https://doi.org/10.1007/978-1-4684-0772-3_6

Download citation

  • DOI: https://doi.org/10.1007/978-1-4684-0772-3_6

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4684-0774-7

  • Online ISBN: 978-1-4684-0772-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics