Turbinatine, A Potential Key Intermediate In The Biosynthesis Of Corynanthean-type Indole Alkaloids

Extraction of the leaves of Chimarrhis turbinata has led to the isolation of turbinatine (1), a new corynanthean-type indole alkaloid, besides four known indole alkaloids, strictosidine, 5α-carboxystrictosidine, vallesiachotamine, and isovallesiachotamine. The structural determination of 1 was based on 1D and 2D spectroscopic data. An evaluation of the DNA-damaging activities of the isolates was performed by means of a bioassay using mutant strains of Saccharomyces cerevisiae, which indicated these compounds were weakly active.66710171021Robbrecht, E., (1988) Op. Bot. Belg., 1, pp. 1-271Delprete, G.P., (1996) Brittonia, 48, pp. 35-44Boom, B.M., Campos, M.T.V.A., (1991) Bol. Mus. Paraense Emílio Goeldi, 7, pp. 223-247Shamma, M., Hindenlang, D.M., (1979) Carbon 13-NMR Shift Assignments of Amines and Alkaloids, pp. 499-616. , Shamma, M., Hindenlang, D. M., Eds.Plenum Press: New YorkDe Silva, K.T.D., Smith, G.N., Warren, K.E.H., (1971) Chem. Commun., pp. 905-907Patthy-Lukáts, A., Károlyházy, L., Szabó, L.F., Podányi, B., (1997) J. Nat. Prod., 60, pp. 69-75De Silva, K.T.D., King, D., Smith, G.N., (1971) Chem. Commun., pp. 908-909Waterman, P.G., Zhong, S., (1982) Planta Med., 45, pp. 28-30Wenkert, E., Chang, C.-J., Chawla, H.P.S., Cochran, D.W., Hagaman, E.W., King, J.C., Orito, K., (1976) J. Am. Chem. Soc., 98, pp. 3645-3655Trager, W.F., Lee, C.M., Phillipson, J.D., Beckett, A.H., (1967) Tetrahedron, 23, pp. 1043-1047Kutchan, T.M., (1998) The Alkaloids: Chemistry and Biology, pp. 259-267. , Cordell, G. A., Ed.Academic Press: LondonVerpoorte, R., Van der Heijden, R., Moreno, P.R.H., (1997) The Alkaloids: Chemistry and Biology, pp. 221-299. , Cordell, G. A., Ed.Academic: LondonLeonard, J., (1999) Nat. Prod. Rep., 16, pp. 319-338Stevens, L.H., (1994) Formation and Conversion of Strictosidine in the Bio Synthesis of Monoterpenoid Indole and Quinoline Alkaloids, p. 121. , Ph.D. Thesis, Leiden UniversityRuffer, M., Kan-Fan, C., Husson, H.P., Stöckigt, J., Zenk, M.H., (1979) J. Chem Soc., Chem. Commun., pp. 1016-1018Hemscheidt, T., Zenk, M.H., (1985) Plant Cell Rep., 24, pp. 216-219Stewart, J.J.P., (1999) MOPAC 2000, , Fujitsu Limited: Tokyo, JapanPeçanha, E.P., Verli, H., Rodrigues, C.R., Barreiro, E.J., Fraga, C.A.M., (2002) Tetrahedron Lett., 43, pp. 1607-1611note(2001) BioMedCAChe 5.0, , Fujitsu Ltd. and Oxford Molecular LtdnotenotenoteRobbrecht, E., Puff, C., Smets, E., (1996) Op. Bot. Belg., 7, pp. 1-10Gunatilaka, A.A.L., Samaranayake, G., Kingston, D.G.I., (1992) J. Nat. Prod., 55, pp. 1648-165