Benzylisoquinoline alkaloid biosynthesis in opium poppy

“…The accumulation of morphinan alkaloids is almost exclusively restricted to the opium poppy. It remains the only commercial source for the narcotic analgesic morphine, codeine, and semisynthetic derivatives of thebaine (Ziegler et al, 2009;Beaudoin and Facchini, 2014). The ability to produce alkaloids is also connected with germinating and developing poppy seedlings, where the alkaloids can be detected after a few days postimbibition (Zichová et al, 1996;Huang and Kutchan, 2000).…”

Section: Introductionmentioning

confidence: 99%

Purification and properties of lipoxygenase from opium poppy seedlings(Papaver somniferum L.)

Holková¹,

Bilka²,

Rauová³

et al. 2016

Turk J Biol

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Lipoxygenase (linoleate:oxygen oxidoreductase; EC 1.13.11.12; LOX) is a key enzyme in the signaling pathway leading to the production of biologically active compounds involved in plant growth development and stress responses. In this study the novel LOX enzyme from opium poppy (Papaver somniferum L.) seedlings was purified to electrophoretic homogeneity and characterized. LOX activity during the germination of opium poppy seeds was analyzed, and the highest LOX activity was determined on the fourth day of germination. Opium poppy LOX was purified from 4-day-old poppy seedlings after ammonium sulfate precipitation followed by hydrophobic chromatography (Phenyl-Sepharose CL-4B), ion exchange chromatography (Q-Sepharose), and affinity chromatography (linoleyl-aminopropyl agarose) for the first time. The relative molecular weight of purified LOX was estimated to be 78 kDa by immunoblotting. The highest enzyme activity occurred at pH 6.5 and 0.75 mM calcium ion concentration. LOX showed preferential activity towards linoleic acid followed by linolenic acid as a substrate. To investigate the positional specificity of the LOX reaction, purified LOX was incubated with linoleic acid, and the products were analyzed by high-performance liquid chromatography. Opium poppy LOX converted linoleic acid to 13-hydroperoxy-(9Z,11E)-octadecadienoic acid (63.5%) and, to a lesser extent, 9-hydroperoxy-(10E,12Z)-octadecadienoic acid (36.5%).

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“…Mechanically damaged P. somniferum was shown to rapidly increase incorporation of bismorphine into the cell wall, decreasing susceptibility to hydrolysis by pectinases, which are often present in salivary secretion of herbivores and are also produced by fungi (Beaudoin and Facchini 2014).…”

Section: Plant Alkaloid Accumulation Strategies and Dynamicsmentioning

confidence: 99%

“…Phloem tissues are not always involved in BIA biosynthesis, as seen in Thalictrum flavum (Ranunculaceae). Phthalide isoquinoline, morphinan, and benzylisoquinoline alkaloids, such as noscapine and papaverine, are major compounds in latex from aerial parts of the plants, whereas benzophenanthridine alkaloids (e.g., sanguinarine) are predominant in roots (Hagel and Facchini 2013;Beaudoin and Facchini 2014).…”

Section: Plant Alkaloid Accumulation Strategies and Dynamicsmentioning

confidence: 99%

Plant Alkaloids: Main Features, Toxicity, and Mechanisms of Action

Matsuura

Fett-Neto

2015

Plant Toxins

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Alkaloids are one of the largest groups of plant secondary metabolites, being present in several economically relevant plant families. Alkaloids encompass neuroactive molecules, such as caffeine and nicotine, as well as life-saving medicines including emetine used to fight oral intoxication and the antitumorals vincristine and vinblastine. Alkaloids can act as defense compounds in plants, being efficient against pathogens and predators due to their toxicity. Fast perception of aggressors and unfavorable environmental conditions, followed by efficient and specific signal transduction for triggering alkaloid accumulation, are key steps in successful plant protection. Toxic effects, in general, depend on specific dosage, exposure time, and individual characteristics, such as sensitivity, site of action, and developmental stage. At times, toxicity effects can be both harmful and beneficial depending on the ecological or pharmacological context. Different strategies are used to study alkaloid metabolism and accumulation. An efficient approach is to monitor gene expression, enzyme activities, and concentration of precursors and of the alkaloid itself during controlled attacks of pathogens and herbivores or upon the simulation of their presence through physical or chemical stimulation. Detailed understanding of alkaloid biosynthesis and mechanisms of action is essential to improve production of alkaloids of interest, to discover new bioactive molecules, and to sustainably exploit them against targets of interest, such as herbivores, pathogens, cancer cells, or unwanted physiological conditions.

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Benzylisoquinoline alkaloid biosynthesis in opium poppy

Cited by 215 publications

References 112 publications

Exploiting plant alkaloids

Exploiting plant alkaloids

Purification and properties of lipoxygenase from opium poppy seedlings(Papaver somniferum L.)

Plant Alkaloids: Main Features, Toxicity, and Mechanisms of Action

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