Abstract
Anthranilic acid (1) is an intermediate in the biosynthesis of tryptophan see Chapter 7) (Fig. 31.1). A number of alkaloids, best known from the family Rutaceae, are biosynthes-ized from this important primary compound
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
AIRY-SHAW, H. K., J. C. WILLIS’ Dictionary of Flowering Plants and Ferns, 8th ed., Cambridge University Press, Cambridge, 1973.
ATTA-UR-RAHMAN and A. BASHA, Biosynthesis of Indole Alkaloids, Oxford University Press, Oxford, 1983.
BERGMAN, J., The quinazolinocarboline alkaloids, in The Alkaloids, Vol. 21 (A. Brossi, ed.), 29–54, Academic Press, New York, 1983.
BHATTACHARYYA, P. and D. P. CHAKRABORTY, Carbazole alkaloids, Fortschr. Chem. Org. Naturst., 52, 159–210 (1987).
BLASKO, G. and G. A. CORDELL, Recent developments in the chemistry of plant-derived anticancer agents, in Economic and Medicinal Plant Research, Vol. 2 (H. Wagner, H. Hikino, and N. R. Farnsworth, eds.), 119–191, Academic Press, London, 1988.
BORRIS, R. P. and J. M. SCHAEFFER, Antiparasitic agents from plants, in Phytochemical Resources for Medicine and Agriculture (H. N. Nigg and D. S. Seigler, eds.), 117–158, Plenum, New York, 1992.
BROOKS, C. W. J. and D. G. WATSON, Phytoalexins, Nat. Prod. Rep., 2, 427–459 (1985).
CAMPBELL, W. E., K. P. FINCH, P. A. BEAN, and N. FINKELSTEIN, Alkaloids of the Rutoideae: Tribe Diosmeae, Phytochemistry, 26, 433–434 (1987).
CHAKRABORTY, D. P. and S. ROY, Carbazole alkaloids. III. Fortschr. Chem. Org. Naturst., 57, 71–152 (1991).
CORDELL, G. A., Introduction to Alkaloids, Wiley-Interscience, New York, 1981.
CRABB, T. A., Nuclear magnetic resonance of alkaloids, in Annual Reports on NMR Spectroscopy, Vol. 13 (G. A. Webb, ed.), 60–210, Academic Press, London, 1982.
DA SILVA, M. F. D. G. F., O. R. GOTTLIEB, and F. EHRENDORFER, Chemosystematics of the Rutaceae: Suggestions for a more natural taxonomy and evolutionary interpretation of the family, Plant Syst. Evol., 161, 97–134 (1988).
ELLIS, B. E., Natural products from plant tissue culture, Nat. Prod. Rep., 5, 581–612(1988).
ENGLER, A., RUTACEAE, Nat. Pflanzenfam. III, 4, 195–201 (1896).
ETHERINGTON, T., R. B. HERBERT, and F. B. JACKSON, Furoquinoline alkaloids from Tylophora asthmatica, Phytochemistry, 16, 1125–1126(1977).
GEISSMAN, T. A. and D. H. G. CROUT, Organic Chemistry of Secondary Plant Metabolism, Freeman Cooper, San Francisco, 1969.
GERZON, K. and G. H. SVOBODA, Acridone alkaloids: Experimental antitumor activity of acronycine, in The Alkaloids, Vol. 21 (A. Brossi, ed.), 1–28, Academic Press, New York, 1983.
GRAY, A. I., Quinoline alkaloids related to anthranilic acid, in Alkaloids and Sulphur Compounds (P. G. Waterman, ed.), Vol. 8 of Methods in Plant Biochemistry (P. M. Dey and J. B. Harborne, eds.), 271–308, Academic Press, London, 1993.
GRöGER, D., Alkaloids derived from tryptophan and anthranilic acid, in Secondary Plant Products (E. A. Bell and B. V. Charlwood, eds.), Encyclopedia of Plant Physiology, N. S., Vol. 8, 128–159, Springer-Verlag, Berlin, 1980.
GRUNDON, M. F., Quinoline alkaloids related to anthranilic acid, in The Alkaloids, Vol. 17 (R. H. F. Manske and R. G. A. Rodrigo, eds.), 105–198, Academic Press, New York, 1979.
GRUNDON, M. F., Aspects of the biosynthesis of coumarins and quinoline alkaloids in the Rutaceae, in Chemistry and Chemical Taxonomy of the Rutales (P. G. Waterman and M. F. Grundon, eds.), 9–30, Academic Press, London, 1983.
GRUNDON, M. F., Quinoline alkaloids related to anthranilic acid, in The Alkaloids, Vol. 32 (A. Brossi, ed.), 341–439, Academic Press, New York, 1988.
JOHNE, S., Quinazoline alkaloids, in The Alkaloids, Vol. 29 (A. Brossi, ed.), 99–140, Academic Press, New York, 1986.
KING, C. L., Y. C. KONG, N. S. WONG, H. W. YEUNG, H. H. S. FONG, and U. SANKAWA, Uterotonic effect of Evodia rutaecarpa alkaloids, J. Nat. Prod., 43, 577–582 (1980).
KONG, Y., K. CHENG, K. NG, P. P. BUT, Q. LI, S. YU, H. CHANG, R. C. CAMBIE, T. KINOSHITA, W. KAN, and P. G. WATERMAN, A chemotaxonomic division of Murraya based on the distribution of the alkaloids yuehchukene and girinimbine, Biochem. Syst. Ecol., 14, 491–497 (1986).
KONG, Y., P. BUT, K. NG, K. CHENG, K. CHANG, K. M. WONG, A. I. GRAY, and P. G. WATERMAN, The biochemical systematics of Merrillia; in relation to Murraya, the Clauseneae and the Aurantioideae, Biochem. Syst. Ecol., 16, 47–50 (1988a).
KONG, Y., P. P. BUT, K. NG, Q. LI, K. CHENG, and P. G. WATERMAN, Micromelum: A key genus in the chemosystematics of the Clauseneae, Biochem. Syst. Ecol., 16, 485–489 (1988b).
KUBO, I. and K. NAKANISHI, Insect antifeedants and repellants from African plants, in Host Plant Resistance to Insects (P. A. Hedin, ed.), ACS Symposium Series 62, 165–178, American Chemical Society, Washington, DC, 1977.
LEETE, E., The biosynthesis of alkaloids, Specialist Periodical Reports, Biosynthesis, 102–223, The Royal Society Chemistry, Cambridge, 1983.
NAHRSTEDT, A., U. EILERT, B. WOLTERS, and V. WRAY, Rutacridone-epoxide, a new acridone alkaloid from Ruta graveolens, Z. Naturforsch., 36c, 200–203 (1980).
NG, K. M., P. P. BUT, A. I. GRAY, T. G. HARTLEY, Y. KONG, and P. G. WATERMAN, The biochemical systematics of Tetradium, Euodia, and Melicope and their significance in the Rutaceae, Biochem. Syst. Ecol., 15, 587–593 (1987).
PONCHET, M., J. MARTIN-TANGUY, A. MARAIS, and A. POUPET, Dianthramides A and B, two N-benzoylanthranilic acid derivatives from elicited tissues of Dianthus caryophyllus, Phytochemistry, 23, 1901–1903 (1984).
PRANCE, G. T., The systematic position of Rhabdodendron Gilg. and Pilg., Bull. Jard. Bot. Nat. Belg., 38, 127–146 (1968).
SEIGLER, D. S., Plant systematics and alkaloids, The Alkaloids, Vol. 16 (R. H. F. Manske, ed.), 1–82, Academic Press, New York, 1977.
SPECIALIST PERIODIC REPORTS, Alkaloids, Vol. 8, Chemical Society, London, 1978. Alkaloids, Vol. 9, Chemical Society, London, 1979.
SUFFNESS, M. and G. A. CORDELL, Antitumor alkaloids, in The Alkaloids, Vol. 25 (A. Brossi, ed.), 3–355, Academic Press, New York, 1985.
WATERMAN, P. G., Alkaloids of the Rutaceae: Their distribution and systematic significance, Biochem. Syst. Ecol., 3, 149–180 (1975).
WATERMAN, P. G., Phylogenetic implications of the distribution of secondary metabolites within the Rutales, in Chemistry and Chemical Taxonomy of the Rutales (P. G. Waterman and M. F. Grundon, eds.), 377–400, Academic Press, London, 1983.
WATERMAN, P. G., The dimeric alkaloids of the Rutaceae derived by Diels-Alder addition, in Alkaloids: Chemical and Biological Perspectives, Vol. 4 (S. W. Pelletier, ed.), 331–387, Wiley, New York, 1986.
WATERMAN, P. G. and M. F. GRUNDON, eds., Chemistry and Chemical Taxonomy of the Rutales, Academic Press, London, 1983.
WATERMAN, P. G. and S. A. KHALID, The biochemical systematics of Fagaropsis angolensis and its significance in the Rutales, Biochem. Syst. Ecol., 9, 45–51 (1981).
WINK, M., Allelochemical properties or the raison d’etre of alkaloids, in The Alkaloids, Vol. 43 (G. A. Cordell, ed.), 1–105, Academic Press, New York, 1993.
Author information
Authors and Affiliations
Rights and permissions
Copyright information
© 1998 Springer Science+Business Media New York
About this chapter
Cite this chapter
Seigler, D.S. (1998). Alkaloids Derived from Anthranilic Acid. In: Plant Secondary Metabolism. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-4913-0_31
Download citation
DOI: https://doi.org/10.1007/978-1-4615-4913-0_31
Publisher Name: Springer, Boston, MA
Print ISBN: 978-1-4613-7228-8
Online ISBN: 978-1-4615-4913-0
eBook Packages: Springer Book Archive