Macrantaline and macrantoridine,new alkaloids from a turkish sample of Papaver pseudo-orientale |
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Authors: | Günay Sariyar JDavid Phillipson |
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Institution: | 1. Department of Pharmacognosy, Faculty of Pharmacy, University of Istanbul, Turkey;2. Department of Pharmacognosy, The School of Pharmacy, University of London, 29-39, Brunswick Square, London WC1N 1AX, England |
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Abstract: | The major alkaloids of the aerial parts of a Turkish sample of Papaver pseudo-orientale are salutaridine and a new alkaloid, macrantaline, UV, IR, PMR, MS and CD have been used to establish the structure of macrantaline as 1-(2′-hydroxymethylene-3′,4′-dimethoxybenzyl)-2-methyl-6,7-methylenedioxy-8-methoxy-1,2,3,4-tetrahydroisoquinoline. The corresponding 2′-methyl substituted analogue prepared from (?)-α-narcotine and also from macrantaline proved to have identical properties, including CD spectra, thus confirming the structure and establishing the absolute configuration of macrantaline. A new minor alkaloid, macrantoridine, yielded macrantaline on lithium aluminium hydride reduction and differs from the latter in that the 2′-substituent is a carboxyl instead of hydroxymethylene. UV, IR, PMR, MS and CD data are reported for macrantoridine. |
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Keywords: | Papaveraceae alkaloids macrantaline 1(-2′-hydroxymethylene-3′ 4′-dimethoxybenzyl)-2-methyl-6 7-methylenedioxy-8-methoxy-1 2 3 4-tetrahydroisoquinoline macrantoridine 1-(2′-carboxy-3′ 4′-dimethoxybenzyl)-2-methyl-6 7-methylenedioxy-8-methoxy-1 2 3 4-tetrahydroisoquinoline salutaridine structural determination |
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