The Diterpenoid Alkaloids from Aconitum napellus
1988; Elsevier BV; Volume: 27; Issue: 5 Linguagem: Inglês
10.3987/com-87-4445
ISSN1881-0942
AutoresGabriel de la Fuente, Mat誕s Reina, Emir Valencia, Antonio Rodr暖uez-Ojeda,
Tópico(s)Chemical synthesis and alkaloids
Resumo~bstract -FromAconitum napellus L. subsp.castellanum J. Molero et C. Blanche, were isolated three new diterpenoid alkaloids, 12-epidehydronapelline (1).12-epi-acetyldehydronapelline (21, and 1.14-dia~et~lneoline ( 6), together with neoline (71, aconitine, and songoramine (51.The structures of the new bases were determined by spectroscopic data and chemical correlation.From the ccol ethnnolic extract of the ahove ground p r + s of plants of Aconitum napellus L. Subsp.castellanum J. Molero et C. Blanche, collected growing in wet soils. in loco dicto Laguna del Marquesado, Cuenca Province, spain,' we have isolated three new diterpenoid alkaloids, 12-epi-dehydronapelline (1) and 12-epiacetyldehydronapelline (21. of the veatchin type, and 1.14-diacetylneoline (61, of the aconitine type.12-~2i-dehydronapelline (11, isolated as a resin, C22H31N03 (M+ 357.2291, calc.357.2303).had la1 +45-(c=0.17,EtOH).Ir (CHCl31, 3580, 3500, and 3450 (br) D (OH), and 1650 and 875 rn-l (exomethylenel.The ms provided ions at m/z, 357 + (26%) M+, 342 (6%) M -CH3, 340 (15%) M+-OH, 329 (18%) M+-CO, 312 (4%) IM+-OHI-CO, 301 (38%) M + -c ~H ~o , 286 (16%) I M + -C ~H ~O ~ -c H ~, and 122 (100%) .The 'H-nmr spectrum of 12-epi-dehydronapelline (11 (200 MHz, CDCl ) displayed characteristic signals 3 of napelline-type alkaloids2 at 6 0.81 (3H, s, CH31, 1.00 (3H, t, J = 7 Hz, N-CH2-CEi3), 2.66 and 2.67 (1H each, dq, J = 7.1 Hz, N-Cg2-CH3), 2.73 (lH, d, J = 1.7 Hz, H-20).2.80 (lH, dd, J1 = 8.7 Hz, J = 4.5 Hz, H-131, 4.12 (lH, dd, J1 = 2 8.5 Hz, J2 = 4.0 Hz, H-12ul , 4.27 (lH, br s, H-15a), and 5.20 and 5.39 (1H.each, hr s, C = C H 2 L The ir absorptions at 1010 and 950 cm-l, the loss of a molecule of acrolein in
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