Pyrrolizidine Alkaloids from Senecio brasiliensis Populations - Journal

Pyrrolizidine Alkaloids from Senecio brasiliensis Populations. G. Schmeda Hirschmann, E. A. Ferro, L. Franco, L. Recalde, and C. Theoduloz. J. Nat. Pr...
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Journal of Natural Products

770

[Vol. 50, No. 4

LITERATURE CITED J. Rudinsky and M.O. Zethner, C a d . Entomol., 99,9 11 (1967). M. Beroza, “Chemicals Controlling Insect Behavior,” Academic Press, New York, 1970, pp. 2140. 3. G.V. Dethier, in: “Chemical Ecology,” Ed. by F. Sondheimer and T.B. Simone, Academic Press, New York, 1970, pp. 83-102. 4. L.M. Schoonhoven, in: “Chemical Mediators between Plants and Phytophagous Insects in Semiochemicals,” Ed. by D.A. Norlund, R.L. Jones, and W.J. Lewis, John Wiley & Sons, New York, 1978, pp. 31-50. 5. J.H. Visset and A.K. Minks, “Insect-Plant Relationships,” Centre for Agricultural Publishing and Documentation, Wageningen, 1982, pp. 95- 122. . 8 , 109 6. N . Hayashi, M. Sholichin, T. -0, Y. Yamamura, and H. Komae, Biorhem. S y ~ t Erof., (1980). 7. N. Hayashi, M. Masuoka, K. Maeshima, T. Sakao, M.Tabata, and H . Komae, Agrir. B i d . Chem., 47,1397 (1983). 8. Y. Hirose, Shrtuqo BunJekz, 15, 162 (1967). 9 . Y. Yukawa and S. Ito, “Spectral Atlas ofTerpenes and the Related Compounds,” Hirokawa, Tokyo, 1973. 10. Y. Masada, “Analysis of Essential Oils by Gas Chromatography and Mass Spectrometry,” Hirokawa, Tokyo, 1975. 1. 2.

R e s e i d 19June I986

PYRROLIZIDINE ALKALOIDS FROM SENECIO BRASILIENSIS POPULATIONS

G. SCHMEDAHIRSCHMANN,E.A. FERRO,L. FRANCO, L. RECALDE,and C. THEODULOZ Facultad de Cienrias Quimiras, Carilla 1055, Asuncion, Paraguay Senacio brasifzensis(Spreng.) Less. (Compositae) has been associated with cattle poisoning in countries bordering the Rio de La Plata (1.2). We report here the pyrrolizidine alkaloids of three S. braJilimris populations growing on rangelands in Paraguay. T h e pyrrolizidine alkaloid content and composition based on dried material and variation in different organs and collection sites are summarized in Table 1.

EXPERIMENTAL PLANTMATERIAL.soluble portion of the EtOH extract of the stems of the plant was chromatographed on Si gel to yield a- and $-peltatin, identified by mp, [ a ) D , ir, ‘H nmr, and tlc. These compounds are well-known cytotoxic constituents of Podopobyllum peltatum (3). To our knowledge, $-peltaiin has been isolated from but one other member of the mint family, Hyptis wticellata

(4). The initial collection of plant material was made by Dr. Aparacio Pereira-Duane (no. 12188) in the State of Minas Gerais, Brazil; the bulk collection was made and authenticated by the Economic Botany Laboratory, USDA, Beltsville, Maryland. Voucher specimens have been deposited in the herbaria of the Jardim Botanico, Rio de Janeiro, and Beltsville, respectively. Full experimental details are available on request to either senior author. ACKNOWLEDGMENTS This study was supported by NCI Grant No. CA- 1300 1-03/04, and by the Pakistan Council for Scientific and Industrial Research through a study grant to Y.A. We acknowledge also the assistance of Dr. Monroe E. Wall, Research Triangle Institute, Raleigh, North Carolina, for preliminary fractionation of the bulk collection.

‘Part XI11 in the series “Antitumor Plants.” For part XII, seeJ. 0l.g. Chem., 47,1519 (1982). The use of the word antitumw in this title signifies no more than the fact that this plant has been deemed of

sufficient interest in this respect by the National Cancer Institute to warrant investigation.