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PubMed2003

Modulation of berberine bridge enzyme levels in transgenic root cultures of California poppy alters the accumulation of benzophenanthridine alkaloids.

California poppy (Eschscholzia californica Cham.) root cultures produce a variety of benzophenanthridine alkaloids, such as sanguinarine, chelirubine and macarpine, with potent biological activity. Sense and antisense constructs of genes encoding the berberine bridge enzyme (BBE) were introduced into California poppy root cultures. Transgenic roots expressing BBE from opium poppy (Papaver somniferum L.) displayed higher levels of BBE mRNA, protein and enzyme activity, and increased accumulation of benzophenanthridine alkaloids compared to control roots transformed with a beta-glucuronidase gene. In contrast, roots transformed with an antisense-BBE construct from California poppy had lower levels of BBE mRNA and enzyme activity, and reduced benzophenanthridine alkaloid accumulation, relative to controls. Pathway intermediates were not detected in any transgenic root lines. Suppression of benzophenanthridine alkaloid biosynthesis using antisense-BBE also reduced the growth rate of the root cultures. Two-dimensional 1H-NMR spectroscopy showed no difference in the abundance of carbohydrate metabolites in the various transgenic roots lines. However, transformed roots with low levels of benzophenanthridine alkaloids contained larger cellular pools of certain amino acids compared to controls. In contrast, cellular pools of several amino acids were reduced in transgenic roots with elevated benzophenanthridine alkaloid levels relative to controls. The relative abundance of tyrosine, from which benzophenanthridine alkaloids are derived, was only marginally altered in all transgenic root lines; thus, altering metabolic flux through benzophenanthridine alkaloid pathways can affect cellular pools of specific amino acids. Consideration of such interactions is important for the design of metabolic engineering strategies that target benzophenanthridine alkaloid biosynthesis.

Alkaloids↗

PubMed1999

Analysis of promoters from tyrosine/dihydroxyphenylalanine decarboxylase and berberine bridge enzyme genes involved in benzylisoquinoline alkaloid biosynthesis in opium poppy.

Tyrosine/dihydroxyphenylalanine decarboxylase (TYDC) and the berberine bridge enzyme (BBE) represent the entry point and a key branch point, respectively, in the biosynthesis of benzylisoquinoline alkaloids in select species of the Papaveraceae and Fumariaceae. Genomic clones for tydc7 and bbe1 from opium poppy (Papaver somniferum L.) were isolated. Deletion analysis of tydc7 and bbe1 5'-flanking regions revealed the location of putative regulatory domains necessary for expression of the beta-glucuronidase (gus) reporter gene in a transient assay system based on the microprojectile bombardment of cultured opium poppy cells. A 105-nucleotide region between -393 and -287 of the tydc7 5'-flanking region, and a 155-nucleotide region between -355 and -200 of the bbe1 5'-flanking region, were found to be essential for promoter activity. RNA gel blot analysis showed that tydc7 and bbe1 expression is induced in cultured opium poppy cells in response to wounding or treatment with a pathogen-derived elicitor. Time-courses for the induction of tydc7 and bbe1 mRNAs in wounded cells were nearly identical to those for GUS activity in cells bombarded with select promoter-gus constructs when the -393 to -287 region of tydc7, or the -355 to -200 region of bbe1, was present. Our data suggest that the wound signal caused by the entry of DNA-coated microcarriers into opium poppy cells was sufficient to induce tydc7 and bbe1 promoter activity, and that wound-responsive regulatory elements are located within domains identified by deletion analysis.

Alkaloids↗

PubMed2004

RNAi-mediated replacement of morphine with the nonnarcotic alkaloid reticuline in opium poppy.

We report on the silencing of codeinone reductase (COR) in the opium poppy, Papaver somniferum, using a chimeric hairpin RNA construct designed to silence all members of the multigene COR family through RNA interference (RNAi). After gene silencing, the precursor alkaloid (S)-reticuline-seven enzymatic steps upstream of codeinone-accumulated in transgenic plants at the expense of morphine, codeine, oripavine and thebaine. Methylated derivatives of reticuline also accumulated. Analysis verified loss of Cor gene transcript, appearance of 22-mer degradation products and reduction of enzyme activity. The surprising accumulation of (S)-reticuline suggests a feedback mechanism preventing intermediates from general benzylisoquinoline synthesis entering the morphine-specific branch. However transcript levels for seven other enzymes in the pathway, both before and after (S)-reticuline, were unaffected. This is the first report of gene silencing in transgenic opium poppy and of metabolic engineering to cause the high-yield accumulation of the nonnarcotic alkaloid reticuline.

Alcohol Oxidoreductases↗

PubMed2001

Morphine metabolism in the opium poppy and its possible physiological function. Biochemical characterization of the morphine metabolite, bismorphine.

We identified a novel metabolic system of morphine in the opium poppy (Papaver somniferum L.). In response to stress, morphine is quickly metabolized to bismorphine consisting of two morphine units, followed by accumulation in the cell wall. This bismorphine binds predominantly to pectins, which possess high galacturonic acid residue contents, through ionical bonds. Our newly developed method using artificial polysaccharides demonstrated that bismorphine bridges are formed between the two amino groups of bismorphine and the carboxyl groups of galacturonic acid residues, resulting in cross-linking of galacturonic acid-containing polysaccharides to each other. The ability of bismorphine to cross-link pectins is much higher than that of Ca2+, which also acts as a cross-linker of these polysaccharides. Furthermore, we confirmed that cross-linking of pectins through bismorphine bridges leads to resistance against hydrolysis by pectinases. These results indicated that production of bismorphine is a defense response of the opium poppy. Bismorphine formation is catalyzed by anionic peroxidase that pre-exists in the capsules and leaves of opium poppies. The constitutive presence of morphine, together with bismorphine-forming peroxidase, enables the opium poppy to rapidly induce the defense system.

Carbohydrate Sequence↗

PubMed2006

Actin depolymerization is sufficient to induce programmed cell death in self-incompatible pollen.

Self-incompatibility (SI) prevents inbreeding through specific recognition and rejection of incompatible pollen. In incompatible Papaver rhoeas pollen, SI triggers a Ca2+ signaling cascade, resulting in the inhibition of tip growth, actin depolymerization, and programmed cell death (PCD). We investigated whether actin dynamics were implicated in regulating PCD. Using the actin-stabilizing and depolymerizing drugs jasplakinolide (Jasp) and latrunculin B, we demonstrate that changes in actin filament levels or dynamics play a functional role in initiating PCD in P. rhoeas pollen, triggering a caspase-3-like activity. Significantly, SI-induced PCD in incompatible pollen was alleviated by pretreatment with Jasp. This represents the first account of a specific causal link between actin polymerization status and initiation of PCD in a plant cell and significantly advances our understanding of the mechanisms involved in SI.

Actin Cytoskeleton↗

PubMed2005

Sanguinarine biosynthesis is associated with the endoplasmic reticulum in cultured opium poppy cells after elicitor treatment.

Three key benzylisoquinoline alkaloid biosynthetic enzymes, (S)-N-methylcoclaurine-3'-hydroxylase (CYP80B1), berberine bridge enzyme (BBE), and codeinone reductase (COR), were localized in cultured opium poppy (Papaver somniferum) cells by sucrose density gradient fractionation and immunogold labeling. CYP80B1 catalyzes the second to last step in the formation of (S)-reticuline, the last common intermediate in sanguinarine and morphine biosynthesis. BBE converts (S)-reticuline to (S)-scoulerine as the first committed step in sanguinarine biosynthesis, and COR catalyzes the penultimate step in the branch pathway leading to morphine. Sanguinarine is an antimicrobial alkaloid that accumulates in the vacuoles of cultured opium poppy cells in response to elicitor treatment, whereas the narcotic analgesic morphine, which is abundant in opium poppy plants, is not produced in cultured cells. CYP80B1 and BBE were rapidly induced to high levels in response to elicitor treatment. By contrast, COR levels were constitutive in the cell cultures, but remained low and were not induced by addition of the elicitor. Western blots performed on protein homogenates from elicitor-treated cells fractionated on a sucrose density gradient showed the cosedimentation of CYP80B1, BBE, and sanguinarine with calreticulin, and COR with glutathione S-transferase. Calreticulin and glutathione S-transferase are markers for the endoplasmic reticulum (ER) and the cytosol, respectively. In response to elicitor treatment, large dilated vesicles rapidly developed from the lamellar ER of control cells and fused with the central vacuole. Immunogold localization supported the association of CYP80B1 and BBE with ER vesicles, and COR with the cytosol in elicitor-treated cells. Our results show that benzylisoquinoline biosynthesis and transport to the vacuole are associated with the ER, which undergoes major ultrastructural modification in response to the elicitor treatment of cultured opium poppy cells.

Alcohol Oxidoreductases↗

PubMed1996

Molecular analysis of a new member of the opium poppy tyrosine/3,4-dihydroxyphenylalanine decarboxylase gene family.

An aromatic amino acid decarboxylase DNA fragment was generated from opium poppy (Papaver somniferum L.) genomic DNA by the PCR using primers designed from conserved amino acid sequences of other aromatic amino acid decarboxylase genes. Using this fragment as a probe, a genomic clone was isolated that encodes a new member of the opium poppy tyrosine/3,4-dihydroxyphenylalanine decarboxylase gene family (TyDC5). The predicted TyDC5 amino acid sequence shares extensive identity with other opium poppy tyrosine/3,4-dihydroxyphenylalanine decarboxylases (84%), and when expressed in Escherichia coli, it is active against tyrosine and to a lesser extent against 3,4-dihydroxyphenylalanine. Ribonuclease protection assays indicate that TyDC5 is expressed primarily in the roots of mature poppy plants. A peak of TyDC5 expression was also observed during germination, coincident with the emergence of the radicle from the seed coat. Parallel results were obtained in transgenic tobacco using a TyDC5 promoter fragment (-2060) translationally fused to the beta-glucuronidase reporter gene (GUS). IN TyDC5::GUS tobacco, GUS activity transiently appeared in all parts of the seedling during germination, but was limited to the roots in older plants. These results indicate that TyDC5 expression is transcriptionally regulated and suggest that the TyDC5 enzyme may play an important role in providing precursors for alkaloid synthesis in the roots and germinating seedlings of opium poppy.

Amino Acid Sequence↗

PubMed1996

Uncoupled defense gene expression and antimicrobial alkaloid accumulation in elicited opium poppy cell cultures.

Treatment of opium poppy (Papaver somniferum L.) cell cultures with autoclaved mycelial homogenates of Botrytis sp. resulted in the accumulation of sanguinarine. Elicitor treatment also caused a rapid and transient induction in the activity of tyrosine/dopa decarboxylase (TYDC, EC 4.1.1.25), which catalyzes the conversion of L-tyrosine and L-dopa to tyramine and dopamine, respectively, the first steps in sanguinarine biosynthesis. TYDC genes were differentially expressed in response to elicitor treatment. TYDC1-like mRNA levels were induced rapidly but declined to near baseline levels within 5 h. In contrast, TYDC2-like transcript levels increased more slowly but were sustained for an extended period. Induction of TYDC mRNAs preceded that of phenylalanine ammonia-lyase (PAL, EC 4.3.1.5) mRNAs. An elicitor preparation from Pythium aphanidermatum was less effective in the induction of TYDC mRNA levels and alkaloid accumulation; however, both elicitors equally induced accumulation of PAL transcripts. In contrast, treatment with methyl jasmonate resulted in an induction of TYDC but not PAL mRNAs. The calmodulin antagonist N-(6-aminohexyl)-5-chloro-1-naphthalenesulfonamide and the protein kinase inhibitor staurosporine partially blocked the fungal elicitor-induced accumulation of sanguinarine. However, only staurosporine and okadaic acid, an inhibitor of protein phosphatases 1 and 2A, blocked the induction of TYDC1-like transcript levels, but they did not block the induction of TYDC2-like or PAL transcript levels. These data suggest that activation mechanisms for PAL, TYDC, and some later sanguinarine biosynthetic enzymes are uncoupled.

Acetates↗

PubMed1998

Expression patterns conferred by tyrosine/dihydroxyphenylalanine decarboxylase promoters from opium poppy are conserved in transgenic tobacco.

Opium poppy (Papaver somniferum) contains a large family of tyrosine/dihydroxyphenylalanine decarboxylase (tydc) genes involved in the biosynthesis of benzylisoquinoline alkaloids and cell wall-bound hydroxycinnamic acid amides. Eight members from two distinct gene subfamilies have been isolated, tydc1, tydc4, tydc6, tydc8, and tydc9 in one group and tydc2, tydc3, and tydc7 in the other. The tydc8 and tydc9 genes were located 3.2 kb apart on one genomic clone, suggesting that the family is clustered. Transcripts for most tydc genes were detected only in roots. Only tydc2 and tydc7 revealed expression in both roots and shoots, and TYDC3 mRNAs were the only specific transcripts detected in seedlings. TYDC1, TYDC8, and TYDC9 mRNAs, which occurred in roots, were not detected in elicitor-treated opium poppy cultures. Expression of tydc4, which contains a premature termination codon, was not detected under any conditions. Five tydc promoters were fused to the beta-glucuronidase (GUS) reporter gene in a binary vector. All constructs produced transient GUS activity in microprojectile-bombarded opium poppy and tobacco (Nicotiana tabacum) cell cultures. The organ- and tissue-specific expression pattern of tydc promoter-GUS fusions in transgenic tobacco was generally parallel to that of corresponding tydc genes in opium poppy. GUS expression was most abundant in the internal phloem of shoot organs and in the stele of roots. Select tydc promoter-GUS fusions were also wound induced in transgenic tobacco, suggesting that the basic mechanisms of developmental and inducible tydc regulation are conserved across plant species.

Amino Acid Sequence↗

PubMed2005

Cell type-specific localization of transcripts encoding nine consecutive enzymes involved in protoberberine alkaloid biosynthesis.

Molecular clones encoding nine consecutive biosynthetic enzymes that catalyze the conversion of l-dopa to the protoberberine alkaloid (S)-canadine were isolated from meadow rue (Thalictrum flavum ssp glaucum). The predicted proteins showed extensive sequence identity with corresponding enzymes involved in the biosynthesis of related benzylisoquinoline alkaloids in other species, such as opium poppy (Papaver somniferum). RNA gel blot hybridization analysis showed that gene transcripts for each enzyme were most abundant in rhizomes but were also detected at lower levels in roots and other organs. In situ RNA hybridization analysis revealed the cell type-specific expression of protoberberine alkaloid biosynthetic genes in roots and rhizomes. In roots, gene transcripts for all nine enzymes were localized to immature endodermis, pericycle, and, in some cases, adjacent cortical cells. In rhizomes, gene transcripts encoding all nine enzymes were restricted to the protoderm of leaf primordia. The localization of biosynthetic gene transcripts was in contrast with the tissue-specific accumulation of protoberberine alkaloids. In roots, protoberberine alkaloids were restricted to mature endodermal cells upon the initiation of secondary growth and were distributed throughout the pith and cortex in rhizomes. Thus, the cell type-specific localization of protoberberine alkaloid biosynthesis and accumulation are temporally and spatially separated in T. flavum roots and rhizomes, respectively. Despite the close phylogeny between corresponding biosynthetic enzymes, distinct and different cell types are involved in the biosynthesis and accumulation of benzylisoquinoline alkaloids in T. flavum and P. somniferum. Our results suggest that the evolution of alkaloid metabolism involves not only the recruitment of new biosynthetic enzymes, but also the migration of established pathways between cell types.

Berberine↗

PubMed2006

Long-distance dispersal vs vicariance: the origin and genetic diversity of alpine plants in the Spanish Sierra Nevada.

Here, we investigated the origin and genetic diversity of four alpine plant species co-occurring in the Spanish Sierra Nevada and other high mountains in south-western Europe by analysis of amplified fragment length polymorphisms (AFLPs). In Kernera saxatilis, Silene rupestris and Gentiana alpina we found intraspecific phylogroups corresponding to mountain regions as predicted by the vicariance hypothesis. Moreover, genetic distances between Sierra Nevada and Pyrenees populations were always higher than those between populations from the Pyrenees and the south-western Alps/Massif Central. This suggests successive disruption of gene exchange between mountain ranges as postglacial climatic warming proceeded from south to north. In Papaver alpinum, our data indicate that a central Pyrenean population arose via long-distance dispersal from the Sierra Nevada, and that vicariant separation events between the Sierra Nevada and the Pyrenees and between the Pyrenees and the south-western Alps occurred simultaneously. Overall, Sierra Nevada populations of all species investigated here preserve unexpectedly high (or not exceptionally reduced) genetic diversity. This testifies to the important influence of long-term isolation, i.e. vicariance, on genetic diversity through fostering the accumulation of new mutations and/or the fixation of ancestral ones.

Brassicaceae↗

PubMed2006

Cross-sensitization between poppy seed and buckwheat in a food-allergic patient with poppy seed anaphylaxis.

The opium poppy, Papaver somniferum L., is the source of both poppy seeds and opium. The commercially available seeds are widely used as ingredients for various kinds of food. IgE-mediated sensitization to poppy seeds is rare, but, if present, clinical symptoms are usually severe. Cross-sensitizations between poppy seeds and other food allergens have been described with sesame, hazelnut, rye grain and kiwi fruit. We report the case of a 17-year-old female with an apparently food-allergic reaction after ingestion of a poppy seed cake. Allergological workup revealed a poppy seed anaphylaxis and led to the identification of a novel cross-sensitization with buckwheat.

Adolescent↗

PubMed1992

Poppy seeds: implications of consumption.

Three white poppy seed samples of Papaver somniferum L were found to contain total morphine (free and bound) in the range 58.4 to 62.2 micrograms/g seeds and total codeine (free and bound) in the range 28.4 to 54.1 micrograms/g seeds. Soaking seeds in water was found to remove 45.6 per cent of the free morphine and 48.4 per cent of the free codeine. In ingesting a curry meal or two containing various amounts of washed seeds (morphine intake: 200.4 to 1002 micrograms; codeine intake: 95.9 to 479.5 micrograms), the urinary morphine levels were found to be in the range 0.12 to 1.27 micrograms/ml urine and urinary codeine levels in the range 0.04 to 0.73 micrograms/ml urine. In any large scale screening for abuse of opiate drugs, the possibility of urinary alkaloids arising from consuming food containing poppy seeds must be considered and, if possible, eliminated.

Codeine↗

PubMed2001

The impact of host plant on the abundance and function of symbiotic bacteria in an aphid.

The black-bean aphid Aphis fabae bears populations of coccoid symbiotic bacteria Buchnera spp. at 2.0-3.2 x 10(7)cells mg(-1)aphid mass and rod-shaped secondary symbionts of uncertain taxonomic affiliation at 0.1-0.6 x 10(7)cells mg(-1)aphid mass. Buchnera provides essential amino acids, supplementing the poor supply in the aphid diet of plant phloem sap. Comparison of the performance of A. fabae containing and experimentally deprived of their bacteria showed that the bacteria caused increased larval mass of aphids reared on Chenopodium album and Papaver dubium plants, but not when reared on Lamium purpureum. In the aphids reared on L. purpureum, the density of the bacteria, especially the secondary symbionts, was significantly elevated, and bacterial-mediated production of the essential amino acid threonine was reduced, even though the essential amino acid content of phloem exudates from L. purpureum had a low threonine content. It is proposed that the shortfall in threonine, possibly compounded by the high density of secondary symbionts, may contribute to the poor performance of the aphids on L. purpureum. This study offers the first evidence to suggest plant-mediated interference with the nutritional function of symbiotic bacteria in any phytophagous insect.

Amino Acids↗

PubMedDate not supplied

[Magnetic liquid influence upon some plant species of pharmaceutical interest].

It was accomplished a study on the influence of a petroleum magnetic liquid upon two plant species of pharmaceutical interest: Papaver somniferum L. and Chelidonium majus L. Experimental observation aimed: callus accumulation, seed germination, mitotic index and fluorescence of the photosynthesis pigments. The plant samples were taken from in vitro cultures obtained from different explant types while the magnetic liquid was added in the culture media in low concentrations (ml/l). The germination test showed a positive influence of the magnetic liquid, the cell division test revealed an increased mitotic index, callus accumulation rate is enhanced while the fluorescence spectra showed maxima shift for the samples in comparison to the controls.

Chelidonium↗

PubMed2001

Comparative efficacy of five herbicides on winter cereal weeds in semi-arid region of Algeria.

Field chemical control trials on cereal weeds were conducted in the Sétif region (north-east of Algeria), using five herbicides. The most abundant weeds were Fumaria densiflora DC., Veronica cymbalaria Bodard, Vaccaria pyramidata Medik, and Papaver rhoeas L.. The herbicides applied at the end-tillering stage of wheat were bromoxynil + diclofop-methyl, flamprop-isopropyl + MCPA, 2,4-D ester, diclofop-methyl and tribenuron-methyl. Compared to the untreated control, they increased grain yield by 359, 294, 216, 174 and 417 kg ha-1, respectively. These results showed the importance of the chemical control, which is applied in the Sétif region on less than 5% of the total surface of cereals.

Algeria↗

PubMed2005

Antioxidant properties of Mediterranean food plant extracts: geographical differences.

Locally grown, wild food plants seasonally contribute a considerable portion of the daily diet in certain Mediterranean areas and it has been suggested that the beneficial effects of the Mediterranean diet on human health partly originate from the antioxidant effect of flavonoid-rich food plants. The nutrient content of most wild plants is higher than that of cultivated ones and may vary depending on the prevailing environmental conditions. Accordingly, three local Mediterranean plant foods (i.e. Cichorium intybus, Sonchus oleraceus, Papaver rhoeas) were collected in Greece (Crete), southern Italy, and southern Spain in order to assess possible differences in their in vitro antioxidant potential. The biological assays revealed diverse intra-plant specific antioxidant effects for the tested extracts ranging from no activity to almost complete protection. Furthermore, substantial differences in the polyphenol content were found for the nutritionally used part of the same plant originating from different locations. However, no clear correlations between the polyphenol content and the extracts' antioxidant activities were found. Taken together, the data suggest that certain local Mediterranean plant foods possess promising antioxidant activity and that the observed biological effects are possibly influenced by the geographically-dependent environmental conditions prevailing during plant growth.

Animals↗

PubMed2006

De novo biosynthesis of morphine in animal cells: an evidence-based model.

Recent empirical findings have contributed valuable mechanistic information in support of a regulated de novo biosynthetic pathway for chemically authentic morphine in animal cells, with many similarities to the extensively characterized multi-enzyme plant pathway in opium poppy (Papaver somniferum). The present review elaborates an evidence-based model of cellular morphine expression that reflects a coalescence of these recent biochemical data with historical data gleaned from over thirty years of neurochemical/neuropharmacological investigation into the etiology and biological significance of dopamine (DA)-related heterocyclic conjugate molecules, termed tetrahydroisoquinoline (TIQ) or benzylisoquinoline (BIQ) alkaloids, and with outstanding work completed over the last decade that has elucidated biochemical and molecular bases of morphine and related isoquinoline alkaloid expression in plant systems. In essence, we are now afforded a rare window of opportunity to firmly establish essential biochemical linkages between plant and animal biosynthetic pathways that have been conserved throughout evolution.

Alkaloids↗