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salutaridine/valmue
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Enzymic conversion of reticuline to salutaridine by cell-free systems from Papaver somniferum.
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A cell-free extract from the opium poppy, Papaver somniferum, was prepared that utilized hydrogen peroxide to convert (+/-)-[3-3H]reticuline to [3H]salutaridine in 80-85% yield based on consumed [3-3H]reticuline. The phenolic-coupling enzyme activity was not detected in the crude homogenate of whole
Crystallization and preliminary X-ray diffraction analysis of salutaridine reductase from the opium poppy Papaver somniferum.
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The opium poppy Papaver somniferum is the source of the narcotic analgesics morphine and codeine. Salutaridine reductase (SalR; EC 1.1.1.248) reduces the C-7 keto group of salutaridine to the C-7 (S)-hydroxyl group of salutaridinol in the biosynthetic pathway that leads to morphine in the opium
Atomic structure of salutaridine reductase from the opium poppy (Papaver somniferum).
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The opium poppy (Papaver somniferum L.) is one of the oldest known medicinal plants. In the biosynthetic pathway for morphine and codeine, salutaridine is reduced to salutaridinol by salutaridine reductase (SalR; EC 1.1.1.248) using NADPH as coenzyme. Here, we report the atomic structure of SalR to
Salutaridine N-Oxide from the Capsules of Papaver bracteatum.
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A novel compound, salutaridine N-oxide ( 1) has been isolated from PAPAVER BRACTEATUM Lindl (Papaveraceae) in which the major alkaloids were salutaridine and thebaine. Semisynthetic 1 was prepared for structure confirmation. Other components of the alkaloidal fraction were isothebaine, oripavine,
Molecular modeling and site-directed mutagenesis reveal the benzylisoquinoline binding site of the short-chain dehydrogenase/reductase salutaridine reductase.
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Recently, the NADPH-dependent short-chain dehydrogenase/reductase (SDR) salutaridine reductase (E.C. 1.1.1.248) implicated in morphine biosynthesis was cloned from Papaver somniferum. In this report, a homology model of the Papaver bracteatum homolog was created based on the x-ray structure of human
CYP719B1 is salutaridine synthase, the C-C phenol-coupling enzyme of morphine biosynthesis in opium poppy.
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Morphine is a powerful analgesic natural product produced by the opium poppy Papaver somniferum. Although formal syntheses of this alkaloid have been reported, the morphine molecule contains five stereocenters and a C-C phenol linkage that to date render a total synthesis of morphine commercially
Transformation of opium poppy (Papaver somniferum L.) with antisense berberine bridge enzyme gene (anti-bbe) via somatic embryogenesis results in an altered ratio of alkaloids in latex but not in roots.
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The berberine bridge enzyme cDNA bbe from Papaver somniferum L. was transformed in antisense orientation into seedling explants of the industrial elite line C048-6-14-64. In this way, 84 phenotypically normal To plants derived from embryogenic callus cultures were produced. The selfed progeny of
Presence and formation of codeine and morphine in the rat.
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Endogenous codeine and morphine were identified in rat brain by immunological determination following HPLC. To demonstrate occurrence of a biosynthetic pathway to morphine in mammals similar to that used by the poppy plant, (+)-salutaridine, (-)-thebaine, and (-)-codeine were administered to rats
RNAi suppression of the morphine biosynthetic gene salAT and evidence of association of pathway enzymes.
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Papaver somniferum L. was transformed with an RNAi construct designed to reduce transcript levels of the gene encoding the morphine biosynthetic enzyme, salutaridinol 7-O-acetyltransferase (SalAT). RNA interference of salAT led to accumulation of the intermediate compounds, salutaridine and
Biosynthesis of the morphine alkaloids.
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Tracer experiments, supported throughout by the analogous chemical transformations, have firmly established the biosynthetic sequence tyrosine -->norlaudanosoline --> reticuline --> salutaridine --> salutaridinol-I -->thebaine --> codeine --> morphine in Papaver somniferum. In general, the farther a
Systematic knockdown of morphine pathway enzymes in opium poppy using virus-induced gene silencing.
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Opium poppy (Papaver somniferum) remains the sole commercial source for several pharmaceutical alkaloids including the narcotic analgesics codeine and morphine, and the semi-synthetic drugs oxycodone, buprenorphine and naltrexone. Although most of the biosynthetic genes have been identified, the
Alkaloids from Papaver cylindricum.
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The major alkaloids obtained from Papaver cylindricum Cullen were oripavine, narcotine, thebaine and rhoeadine. Floripavidine, papaverine, salutaridine, armepavine, N-methylasimilobine, scoulerine and cheilanthifoline were obtained as minor alkaloids. There have been no previous reports of alkaloids
Alkaloids from Papaver armeniacum, P. fugax and P. tauricola.
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Species from the section Miltantha are reviewed in the context of their contained alkaloids. Thebaine was isolated as the major alkaloid from a sample of P. fugax together with narcotine, pronuciferine, alpinigenine, O-ethylalpinigenine, amurensinine, N-methyl-crotonosine, armepavine, isocorydine
Alkaloids of Papaver orientale and papaver pseudo-orientale.
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Dry latex of Paaver orientale was shown to contain 20% oripavine and 9% thebaine. Dry latex of Papaver pseudo-orientale contained two major alkaloids, isothebaine (11.7%) and orientalidine (0.5%), and the minor alkaloids bracteolin, salutaridine, Or1, Or2, PO-4, alborine (PO-5), and a novel alkaloid
High pressure liquid chromatographic determination of the five major alkaloids in Papaver somniferum L. and thebaine in Papaver bracteatum Lindl. capsular tissue.
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A high pressure liquid chromatographic isocratic procedure is described for determining and quantitating the 5 major alkaloids narcotine, papaverine, thebaine, codeine, and morphine in Papaver somniferum L. and thebaine in Papaver bracteatum Lindl. Other papaveraceous alkaloids, including
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