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Tropane Alkaloids from Schizanthus pinnatus

1988; Elsevier BV; Volume: 27; Issue: 8 Linguagem: Inglês

10.3987/com-88-4562

1881-0942

Gabriel de la Fuente, Mat誕s Reina, Orlando Mu撲z, Aurelio San Mart地, Jean-Pierre Girault,

Traditional and Medicinal Uses of Annonaceae

From Schizanthus pinnatus Ruiz e t Pau.we have isolated seven new tropon-3a,60-dioZ diesters, schizanthines F 111, G (21, H 13j, I 141, K 181, L 191, a n d M 1101, together w i t h tropine, I-)-60-angetoytoxytropan-38-oZ 151, ( -I -6 8 -t i g l o y t a z y t r o p a n -3 4 161, and i-l-38-sene-cioyZoxytropan-68-02 171.The structures of the new atkatoids were determined mainty by spectroscopic methods comprising 2-D and I-D nmr long-range heteronuctear corretations.S r h i z a n t h u s , an endemic genus of chile,' has been included in the Solsnacea family because of the isolation of tropane alkaloid^.^-^Continuing our work on that genus5 we report here on the structure determination of schizanthines F (11, G (2).H (3). I (4).K (8).L (9). and M (10).new tropan-3a.66-dioldiesters, isolated from plants of Schizanthus pinnatus Ruiz et Pav.6 The new bases were 3a.65-diacyloxytropanes.as inferred from the distinctive nmr signals for H-1, H-3, H-5, and ~-6 , ~-~' ~ at 6 3.04-3.20(br s, W$ = 8-8.5 Hz), 1 4.95-5.10(t,J=4.5-5.2HZ), 3.18-3.32(m, W-= 15 Hz), and 5.34-5.47(dd, J1 = 2 7.5-7.7 Hz, s2 = 3.1-3.2Hz), respectively, and the typical ms fragments at m/z 96, 95, 94, 82, and 81.~"The nature of the esters was also evident from their characteristic signals in the ' H nmr spectra: 6 6.62-6.72 (lH, q, J = 1.6 Hz, H-91 and 2.15-2.29 (3H, d, J = 1.5-1.7 Hz, H-12) for mesaconic esters;1° 3.27-3.34(2H.s , H-9) and 5.69-5.74and 6.29-6.36(1H each, s, H-12) for itaconic esters,''1.82-1 1.86 (3H, m, W-= 4-4.5 Hz, H-ll'), 1.94-1.98(3H, dq, J -7-7.2 Hz, J 2 = 1.4-1.5 2 1 - HZ, ~-12*), and 6.03 (IH, q, J = 7.1-7.3Hz, H-lo*) for angelic esters,12 and 1.64-1.78(3H, d, J = 7 Hz, H-12-), 1.66-1.83(3H, br s , H-11-1, and 6.68-6.77(lH, q, J = 6.9-7.2Hz, H-10.) for tiglic esters.12