rhoeas are in agreement with other published results 17, 22, 23 and consistent with the absence of morphinan-related genes in this species.įrom the other species in our analysis, promorphinans were identified as minor compounds in P. Our results of zero peak area for morphinans in P. rhoeas capsule material conducted using high resolution accurate mass LC-MS does not detect morphinans or promorphinans above defined limits of detection (Supplementary Data 1), which for morphine is 226-fold lower than morphine levels in P. rhoeas appears to have been conducted without the use of known morphinan standards 14. A recent report of trace amounts of morphinans in P. setigerum 14 were the only species identified as producing morphinans. bracteatum and oripavine the most prominent in P. As previously reported, we found thebaine to be the most prominent metabolite in P. To determine the presence of promorphinan and morphinan compounds and related genes in the 11 species metabolite profiling of latex from juvenile plants and capsule material post-harvest was carried out (Table 1 and Supplementary Data 1). Source data are provided as a Source Data file. Presence of the STORR and the four promorphinan genes are shown under species names (Supplementary Data 2). Species highlighted with an asterisk indicate all gene sequences were identified and retrieved from the corresponding annotated genomes whereas for the remaining nine Papaver species, transcriptomic datasets were used. Taxonomy groupings of the species are indicated and the twelve Papaver species are placed into two different clades (Clade 1 and Clade 2) as described by Carolan et al. Light-blue bars at the nodes indicate the range with 95% highest posterior density. Phylogeny and divergence dates are estimated using BEAST2, which are shown on the nodes. b Species phylogeny inferred by Bayesian inference species tree using eight single copy conserved ortholog sequences.
Compound names are in black and enzymes specific to the promorphinan and morphinan pathway are in red. Conversion of ( S)- to ( R)-reticuline by STORR represents the first committed step in biosynthesis of the promorphinans (salutaridine, Salutaridinol and salutaridinol-7- O-acetate) and morphinans (thebaine, oripavine, codeine and morphine).
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( S)-reticuline is the central branch point of BIA metabolism in opium poppy for the production of structurally distinct compounds including the morphinans plus noscapine, berberine and sanguinarine. STORR is clustered with four other genes involved in synthesis of the first morphinan, thebaine and ten genes involved in synthesis of the phthalideisoquinoline, noscapine, which together make up the BIA gene cluster in opium poppy 5.Ī Schematic of the benzylisoquinoline pathway and enzymes in Opium Poppy with a focus on morphinan production. Composed of P450 and oxidoreductase modules, this fused protein completes the epimerization of ( S)- to ( R)-reticuline, the first step in the morphinan pathway 3, 4, 7.
The gateway reaction leading to morphinan biosynthesis is catalysed by the STORR protein.
The common precursor and central branch point in the pathway for production of the many structurally distinct subclasses of BIAs in the Ranunculales including morphinan, protoberberine, phthalideisoquinoline and benzophenanthridine is the 1-benzylisoquinoline alkaloid, ( S)-reticuline 6 (Fig. The commercial importance of opium poppy has led to its use as a model species for research into the biosynthetic pathway for morphinan production 2, 3, 4, 5. They are naturally synthesised in the genus Papaver and are currently commercially produced in opium poppy, Papaver somniferum, from the Papaveraceae family. The naturally synthesised morphinans thebaine, oripavine, codeine and morphine are part of the BIA class of alkaloids, with morphine renowned for its powerful analgesic properties. The benzylisoquinoline alkaloids or BIA’s represent a structurally diverse group predominantly identified in the order Ranunculales 1, 2.
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