Abstract
Phenylalanine and tyrosine give rise to many secondary plant products. Phenylalanine is preferably converted to cinnamic acid, the parent substance of the large group of nonnitrogenous phenylpropanoids (Progr. Bot. 40, 126 ff.; 41, 93ff.; SCHÜTTE, 1981). Tyrosine and dopa lead preferably to the corresponding alkaloids. The usual pathway to the alkaloids starts with dopamine (I), the decarboxylation product of dopa, which can give the simple phenethylamines like mescaline (II) (PAUL, 1973; SMITH, 1977; BASMADJIAN et al., 1978) or which can react according to a Mannich reaction with carbonyl compounds to give tetrahydroisoquinolines (cf. LIEBISCH, 1969). Most important is the reaction of dopamine derivatives with phenylpyruvic acid derivatives yielding benzyltetrahydroisoquinolines and the different derived compounds. The principles of this pathway were established in the 1960’s (cf. SCHÜTTE, 1969; Herbert, 1979; FODOR, 1980). Here some recent results in this field should be discussed.
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References
AKASU, M., ITOKAWA, H., FUJITA, M.: Phytochemistry 15, 471–473 (1976).
BARTON, D.H.R., COHEN, T.: 117–143, in: Festschrift A. STOLL. Basel: Birkhäuser 1957.
BARTON, D.H.R., KIRBY, G.W., STEGLICH, W., THOMAS, G.M., BATTERSBY, A.R., DOBSON, T.A., RAMUZ, H.: J. Chem. Soc. 1965, 2423–2438. 1957
BARTON, D.H.R., KIRBY, G.W., WIECHERS, A.: J. Chem. Soc. 1966, 2313–2319. 1957
BARTON, D.H.R., BHAKUNI, D.S., CHAPMAN, G.M., KIRBY, G.W.: J. Chem. Soc. (C) 1967a, 2134–2140.
BARTON, D.H.R., BHAKUNI, D.S., CHAPMAN, G.M., KIRBY, G.W., HAYNES, L.J., STUART, K.L.: J. Chem. Soc. (C) 1967b 1295–1298.
BARTON, D.H.R., JAMES, R., KIRBY, G.W., TURNER, D.W., WIDDOWSON, D.A.: J. Chem. Soc. (C) 1968, 1529–1537.
BARTON, D.H.R., BOAR, R.B., WIDDOWSON, D.A.: J. Chem. Soc. (C) 1970a 1208–1213;
BARTON, D.H.R., BOAR, R.B., WIDDOWSON, D.A. J. Chem. Soc. (C) 1970b, 1213–1218.
BARTON, D.H.R., GUNATILAKA, A.A.L., LETCHER, R.M., LOBO, A.M.F.T., WIDDOWSON, D.A.: J. Chem. Soc. Perkin I 1973, 874–880.
BARTON, D.H.R., BRACHO, R.D., POTTER, C.J., WIDDOWSON, D.A.: J. Chem. Soc. Perkin I 1974a 2278–2283.
BARTON, D.H.R., POTTER, C.J., WIDDOWSON, D.A.: J. Chem. Soc. Perkin I 1974b 346–348.
BATTERSBY, A.R.: In: Oxidative Coupling of Phenols, eds. BATTERSBY, A.R., TAYLOYR, W.I. New York: Dekker 1967.
BATTERSBY, A.R., BROWN, R.T., CLEMENTS, J.H., IVERACH, G.G.: Chem. Commun. 1965a 230–232.
BATTERSBY, A.R., FOULKES, D.M., BINKS, R.: J. Chem. Soc. 1965b, 3323–3332.
BATTERSBY, A.R., BROCKSON, T.J., RAMAGE, R.: Chem. Commun. 1969, 464–465.
BATTERSBY, A.R., McHUGH, J.L., STAUNTON, J., TODD, M.: Chem. Commun 1971, 985–986.
BATTERSBY, A.R., HERBERT, R.B., McDONALD, E., RAMAGE, R., CLEMENTS, J.H.: J. Chem. Soc. Perkin I 1972, 1741–1746.
BATTERSBY, A.R., McDONALD, E., MILNER, J.A.: Tetrahedron Lett. 1975, 3419–3422.
BASMADJIAN, G.P., HUSSAIN, S.F., PAUL, A.G.: Lloydia 41, 375–380 (1978).
BHAKUNI, D.S., JAIN, S.: Tetrahedron 36, 2153–2156 (1980).
BHAKUNI, D.S., JOSHI, P.P.: Tetrahedron 31, 2575–2579 (1975).
BHAKUNI, D.S., SINGH, A.N.: Tetrahedron 34, 1409–1410 (1978a)
BHAKUNI, D.S., SINGH, A.N. J. Chem. Soc. Perkin I 1978b 618–622.
BHAKUNI, D.S., SATISH, S., DHAR, M.M.: Phytochemistry 9, 2573–2580 (1970)
BHAKUNI, D.S., SATISH, S., UPRETY, H., KAPIL, R.S.: Phytochemistry 13, 2767–2769 (1974).
BHAKUNI, D.S., UPRETY, H., WIDDOWSON, D.A.: Phytochemistry 15, 739–741 (1976).
BHAKUNI, D.S., SINGH, A.N., KAPIL, R.S.: Chem. Commun. 1977a 211–212.
BHAKUNI, D.S., SINGH, A.N., TEWARI, S., KAPIL, R.5.: J. Chem. Soc. Perkin I 1977b 1662–1666.
BHAKUNI, D.S. TEWARI, S., KAPIL, R.S.: J. Chem. Soc. Perkin I 1977c 706–708.
BHAKUNI, D.S., JAIN, S., SINGH, A.N.: J. Chem. Soc. Perkin I 1978a, 380–383.
BHAKUNI, D.S., LABROO, V.M., SINGH, A.N., KAPIL, R.S.: J. Chem. Soc. Perkin I 1978b 121–125.
BHAKUNI, D.S., MANGLA, V.K., SINGH, A.N., KAPIL, R.S.: J. Chem. Soc. Perkin 11978c, 267–269.
BHAKUNI, D.S., SINGH, A.N., JAIN, S., KAPIL, R.S.: Chem. Commun. 1978d 226–228.
BHAKUNI, D.S., JAIN, S., CHATURVEDI, R.: Tetrahedron 35, 2323–2326 (1979).
BHAKUNI, D.S., SINGH, A.N., JAIN, S.: Tetrahedron 36, 2149–1251 (1980).
BLASCHKE, G.: Arch. Pharm. 301, 432–439 (1968)
BLASCHKE, G. Arch. Pharm. 303, 358–363 (1970).
BLASCHKE, G., WALDHEIM, G., SCHANTZ, M.v., PEURA, P.: Arch. Pharm. 307, 122–130 (1974).
BROCHMANN-HANSSEN, E. FU, C.-C. MISCONI, L.Y.: J. Pharm. Sci. 60, 1880–1883 (1971).
BROCHMANN-HANSSEN,E., CHEN, C.-H., CHIANG, H.-C., McMURTREY, K.: Chem. Commun. 1972 1269.
BROCHMANN-HANSSEN, E., CHEN, C.-H., CHEN, C.R., CHIANG, H.-C., LEUNG, A.Y., McMURTREY, K.: J. Chem. Soc. Perkin I 1975, 1531–1537.
CHAMBERS, C., STUART, K.L.: Chem. Commun. 1968, 328–329.
DELFEL, N.E.: Phytochemistry 19, 403–408 (1980a).
DELFEL, N.E. Planta Med. 39, 168–179 (1980b).
DELFEL, N.É., ROTHFUS, J.A.: Phytochemistry 16, 1595–1598 (1977).
DEWAN, O.P., BHAKUNI, KAPIL, R.S.: J. Chem. Soc. Perkin I 1978, 622–624.
DUPKE, D., FLENTJE, H., JEFFS, P.W.: Tetrahedron 24, 4459–4476 (1968).
FITZGERALD, J.S., JOHNS, S.R., LAMBERTON, J.A., SIOUMIS, A.A.: Austral. J. Chem. 22, 2187–2201 (1969).
FODOR, G.B., in: Encyclopedia of Plant Physiology, New Series, Vol. 8, eds. E.A. BELL, B.V. CHARLWOOD, p. 92–127. Berlin-Heidelberg- New York: Springer 1980.
FRANK, B., TEETZ, V.: Angew. Chem. 83, 409–410 (1971).
FRESNO, M., JIMENEZ, A., VAZQUEZ, D.: Eur. J. Biochem. 72, 323–330_ (1977).
GITTERMAN, A., PARRY, R.J., DUFRESNE, R.F., STERNBACH, D.D., CABELLI, M.D.: J. Am. Chem. Soc. 102, 2074–2081 (1980).
GROSS, S.R., BURNS, R.O., UMBARGER, E.: Biochemistry 2, 1046–1056 (1963).
HERBERT, R.B., in: Comprehensive Organic Chemistry, eds. D.H.R. BARTON, W.D. OLLIS, Vol. 5, p. 1045–1119. Oxford: Pergamon Press 1979.
IMPELLIZZERI, G., PIATTELLI, M.: Phytochemistry 11, 2499–2502 (1972).
JOHNS, S.R., LAMBERTON, J.A., SIOUMIS, A.A.: Aust. J. Chem. 22, 2219–2231 (1969).
LEETE, E., AHMAD, A.: J. Am. Chem. Soc. 88, 4722–4775 (1966).
LIEBISCH, H.W., in: Biosynthese der Alkaloide, eds. K. MOTHES, H.R. SCHÜTTE, p. 101–122. Berlin: VEB Deutscher Verlag der Wissenschaften 1969.
MILLER, H.E., ROSLER, H., WOHLPART, A., WYLER, H., WILCOX, M.E., FROHOFER, H., MARBY, T.J., DREIDING, A.S.: Heiv. Chim. Acta 51, 1470–1474 (1968).
PANDE, H., BHAKUNI, D.S.: J. Chem. Soc. Perkin I 1976, 2197–2202.
PARRY, R.J.: Recent Adv. Phytochem. 13, 55–84 (1979).
PARRY, R.J., SCHWAB, J.M.: J. Am. Chem. Soc. 97, 2555–2557 (1975).
PARRY, R.J., CHANG, M.N.T., SCHWAB, J.M., FOXMAN, B.M.: J. Am. Chem. Soc. 102, 1099–1111 (1980).
PAUDLER, W.W., McKAY, J.: J. Org. Chem. 38, 2100–2112 (1973).
PAUL, A.G.: Lloydia 36, 36–45 (1973).
POWELL, R.G.: Phytochemistry 11, 1467–1478 (1972).
POWELL, R.G., MIKOLAJCZAK, K.L.: Phytochemistry 12, 2987–2991 (1973).
POWELL, R.G., WEISLEDER, D., SMITH, C.R., Jr., WOLFF, I.A.: Tetrahedron Lett. 1969, 4081–4084.
POWELL, R.G., MIKOLAJCZAK, K.L., WEISLEDER, D., SMITH, C.R., Jr.: Phytochemistry 11, 3317–3320 (1972a).
POWELL, R.G., WEISLEDER, D., SMITH, C.R., Jr.: J. Pharm. Sci. 61, 1227–1230 (1972b).
PRAKASH, O., BHAKUNI, D.S., KAPIL, R.S.: J. Chem. Soc. Perkin I 1979, 1515–1518
RAZAROV, R., YUNUSOV, S.Y., NASYROV, S.M., CHEKHLOV, A.N., ADRIANOV, V.G., STRUCHKOV, Y.T.: Chem. Commun. 1974, 150–151.
SCHÜTTE, H.R., in: Biosynthese der Alkaloide, eds. K. MOTHES, H.R. SCHÜTTE, p. 367–419. Berlin: VEB Deutscher Verlag der Wissenschaften 1969.
SCHÜTTE, H.R.; Biosynthese von niedermolekularen Naturstoffen. Jena: VEB Gustav Fischer 1981.
SCHWAB, J.M., CHANG, M.N.T., PARRY, R.J.: J. Am. Chem. Soc. 99, 2368–2370 (1977).
SHAMMA, M., MONIOT, J.L., YAO, S.Y., MIANA, G.A., IKRAM, M.: J. Am. Chem. Soc. 95, 5742–5747 (1973).
SHAMMA, M., FOY, J.E., MIANA, G.A.: J. Am. Chem. Soc. 96, 7809–7811 (1974).
SHAMMA, M., FOY, J.E., GOVINDACHARI, T.R., VISWANATHAN, N.: J. Org. Chem. 1976, 1293–1294.
SIVAKUMARAN, M., GOPINATH, K.W.: Indian J. Chem. 14B, 150–151 (1976).
SMITH, T.A.: Phytochemistry 16, 9–18 (1977).
STAUNTON, J.: Planta Med. 36, 1–20 (1979).
STUART, K.L., GRAHAM, L.: Phytochemistry 12, 1967–1972 (1973).
STUART, K.L., TEETZ, V., FRANK, B.: Chem. Commun. 1969, 333.
TACKIE A.N., DWUMA-BADU, D., AYIM, J.S.K., DABRA, T.T., KNAPP, J.E., SLATKIN, D.J., Jr.: Lloydia 38, 210–212 (1975).
SLATKIN, D.J., SCHIFF, P. S., BHAKUNI, D.S., KAPIL, D., AYIM, J.S.K., DABRA, T.T., KNAPP, J.E., L., Jr.: Lloydia 38, 210–212 (1975).
TEWARI, S., BHAKUNI, D.S., KAPIL, R.S.: Chem. Commun. 1975, 554–555.
UPRETY, H., BHAKUNI, D.S., KAPIL, R.S.: Phytochemistry 14, 1535–1537 (1975).
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Schütte, HR. (1981). Secondary Plant Substances. In: Ellenberg, H., Esser, K., Kubitzki, K., Schnepf, E., Ziegler, H. (eds) Progress in Botany/Fortschritte der Botanik. Progress in Botany/Fortschritte der Botanik, vol 43. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68297-1_6
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