Isolation and chemistry of the alkaloids from some plants of the genus Papaver. XXXV. The structure of the alkaloids amurensine and amurensinine

Alkaloids fromPapaver armeniacum,P. fugaxandP. tauricola

“…Cryptopine (14) UV XM,H 234, 286 nrn (log e 4.02, 3.76), identical with literature [26]; MS. rn/c (%), 369 (M ; 9), 190 (7), 179 (23), 148 (100), identical with literature [30]; TLC Rf values and colour reactions identical with reference alkaloid (Table III), Rhoeagenine (15) pale cream crystals from me-0-Ethyiglaucamine (22) UV 235, 285 nm, identical with literature [22]; MS. rn/c (%), 413 (M; 74), 384 (Mt29; 80), 234 (6), 220 (35), 206 (11), 193 (100), identical with literature [32]; TLC R, values and colour reactions are given in Table III. Alpinigenine (23) UV XMH 230, 284 nm (log 4.19, 3.79), identical with literature [34]; MS, rn/c (%) 401 (M; 38), 386 (M-15; 6), 383 (8), 370(6), 222 (100), 208 (19), 206 (4), 179 (67), identical with literature [32,34]; TLC R-values and colour reactions are given in Table III…”

An experimental design approach using response surface techniques to obtain optimal liquid chromatography and mass spectrometry conditions to determine the alkaloids in Meconopsi species

“…By comparing the UV and high resolution ESI-MS/MS spectra data and retention time with the authentic compounds, eight of them were unequivocally identified, namely tricin (1), hydnocarpin (2), O-methylflavinantine (3), oleracein E (4), mecambridine (5), protopine (6), alborine (7) and berberine (8) 4 , respectively. Seven other peaks (peaks 9-18) could only be tentatively identified as 8,9-dihydroprooxocryptochine (9) [11], magnofloring (10) [38], 6-methoxy-17-methyl-2,3-[methylenebis(oxy)]-morphinan-5-en-7-one (11) [39], reframoline (12) [11], mecambroline (13) [38], amurensine (14) [40], amurensinine (15) [38], meconoquintupline (16) [41], cryptopine (17) [38], and corysamine (18) [38], by comparing the HR-MS and MS/MS data with literature. In general, all nine samples of the six Meconopsi species contain compounds 6, 7, 8, and 18, with high contents of compounds 6 and 18.…”

A Simple and Efficient Synthetic Route to Chiral Isopavines. Synthesis of (−)-O-Methylthalisopavine and (−)-Amurensinine

“…(−)-(5 R ,12 S )- N -Methyl-2,3-(methylenedioxy)-8,9-dimethoxyisopavinane (7d) [(−)-Amurensinine]. According to the typical procedure, amurensinine 7d was obtained from isopavinane 6d in 95%: mp 160−163 °C (EtOH−Et 2 O) (lit …”

“…According to the typical procedure amine 3b was obtained from imine 2b and (3,4dimethoxybenzyl)magnesium chloride (1a) in 80% yield: mp 104-106 °C (n-heptane); [R] 20 D ) +62.3 (c ) 0.1, EtOH); 1 H NMR (CDCl3) 2.10 (br s, 2H), 2.88 (dd, 1H, J ) 13.4, 6.9), 2.97 (dd, 1H, J ) 13.4, 6.4), 3.53 (dd, 1H, J ) 10.6, 6.9), 3.66-3.88 (m, 15H), 6.44 (d, 1H, J ) 1.9), 6.51-6.73 (m, 5H), 7.14-7.29 (m, 5H); 13 C NMR (CDCl3) 43.5, 55.6, 55.7, 55.8, 61.6, 61.8, 65.5, 110.2, 110.7, 110.8, 112.6, 119.3, 121.3, 127.1, 127.3, 128.4, 131.0, 136.0, 141.1, 147.3, 147.9, 148.4, 148.7; IR (KBr) υ 3520-3200 cm -1 ; MS (EI) m/z (rel intensity) 300 (100), 285 (51), 225 (16), 207 (9), 151 (12), 128 (9), 119 (8), 91 (7), 77 (5). Anal.…”