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PubMed2007

Increasing morphinan alkaloid production by over-expressing codeinone reductase in transgenic Papaver somniferum.

Only plants of the Papaver genus (poppies) are able to synthesize morphinan alkaloids, and cultivation of P. somniferum, opium poppy, remains critical for the production and supply of morphine, codeine and various semi-synthetic analgesics. Opium poppy was transformed with constitutively expressed cDNA of codeinone reductase (PsCor1.1), the penultimate step in morphine synthesis. Most transgenic lines showed significant increases in capsule alkaloid content in replicated glasshouse and field trials over 4 years. The morphinan alkaloid contents on a dry weight basis were between 15% and 30% greater than those in control high-yielding genotypes and control non-transgenic segregants. Transgenic leaves had approximately 10-fold greater levels of Cor transcript compared with non-transgenic controls. Two cycles of crossing of the best transgenic line into an elite high-morphine genotype resulted in significant increases in morphine and total alkaloids relative to the elite recurrent parent. No significant changes in alkaloid profiles or quantities were observed in leaf, roots, pollen and seed.

Alcohol Oxidoreductases↗

PubMed1975

The determination of thebaine in Papaver bracteatum Lindl by gas-liquid chromatography.

Several solvents have been examined in the process of developing a convenient method for extracting powdered material and removing interfering pigments to produce an extract of Papaver bracteatum suitable for g.l.c. assay. The most suitable extracting solvent was aqueous acetic acid (5%); the assay method gave satisfactory reproducibility with a wide range of plant materials (coefficient of variation 0.63 to 3.33%). The accuracy was checked by recovery experiments with pure thebaine and by examination of exhausted marcs. The presence of other alkaloids did not interfer with the assay. There were substantial differences in the amounts of thebaine extracted from capsule and root samples by ammoniacal methanol and by aqueous acetic acid, indicating the presence of thebaine in a "bound" form. The minimum amount of thebaine that could readily be determined by the g.l.c. method was 0.3 mg in the sample of powder used for the assay.

Acetates↗

PubMed2006

Opium Poppy (Papaver somniferum).

The genetic transformation of opium poppy, Papaver somniferum, offers the opportunity to study the mechanisms involved in the regulation of benzylisoquinoline and morphinan alkaloid biosynthesis. The development of an efficient transformation protocol for opium poppy has allowed us to transform a range of genotypes from all around the world, including previously recalcitrant high-yielding commercial Australian cultivars. The method involves Agrobacterium tumefaciens infection of hypocotyl explants, followed by the production of antibiotic or herbicide resistant embryogenic callus, the subsequent induction of somatic embryos and development into normal plants. The use of different selective agents, binary vectors, and poppy genotypes has demonstrated the robustness and reliability of this protocol in the production of many hundreds of confirmed transgenic poppies.

Agrobacterium tumefaciens↗

PubMedDate not supplied

Thebaine variations between germplasm sources within one collection of Papaver bracteatum Lindl.

Plants of Papaver bracteatum Lindl. derived from different germplasm sources within one Iranian collection were grown for 18 and 37 weeks in the greenhouse and controlled environment chambers. Gas-chromatographic analyses showed significant differences between thebaine concentrations of root tissue for 18-week-old plants, but not for 37-week-old plants. The two age groups did not differ in thebaine yield per unit of dry weight of root tissue. However, due to more profuse root growth, the total yield of thebaine from roots of the older plants was about four times that of the younger plants. Shoot thebaine concentrations differed significantly for 18- and 37-week-old plants. The over-all mean thebaine concentration for shoots of older plants was nearly twice that of younger plants. The variation in thebaine concentrations in these plants suggested genetic differences between the germplasm sources. Thus, domestication of P. bracteatum will require selection of germplasm from within and between collections, for plants of the greatest economic potential.

Iran↗

PubMed1997

[Minor alkaloids from the capsule of Papaver nudicaule L].

Two minor alkaloids were isolated from the capsule of Papaver nudicaule. On the basis of physicochemical methods and spectroscopic analysis, they were identified as chelidonine, 5-hydroxy-2-hydroxymethylpyridine. Chelidonine was isolated from this plant and 5-hydroxy-2-hydroxymethylpyridine was isolated from genus for the first time.

Alkaloids↗

PubMed2000

[Characteristics of Papaver somniferum L. cv. ikkanshu cultivated in Izu].

The seeds of Papaver somniferum L. cv. Ikkanshu were sown in November (Autumn sowing: AS) and March (Spring sowing: SS) in a field at Izu Experimental Station for Medicinal Plants of National Institute of Health Sciencs, and both AS and SS plants were cultivated to investigate their growth, opium yield and alkaloid content in the opium. Growing periods from the sowing to the opium harvest were approximately six months for AS plants and three months for SS plants. Sizes of plants and capsules in AS were bigger than those in SS, reflecting their growth period. Opium yields per an are in AS and SS were 212.09 g and 142.03 g, respectively. The opium was able to be collected four times in the AS plants though the SS plants ceased to exude opium after the second incision. Therefore higher yield of opium in AS plants seems to be attributed to an amount of opium in the third and fourth incision. Average morphine content in the total opium was 15.61% in AS plants and 15.04% in SS plants, and the estimated amounts of morphine per an are in AS and SS plants were 33.16 g and 21.38 g, respectively.

Government Agencies↗

PubMed2001

Isoquinoline alkaloid production by transformed cultures of Papaver somniferum.

Three clones of transformed cultures of opium poppy (Papaver somniferum L.) were established by infection with Agrobacterium rhizogenes MAFF 03-01724. MAFF clone 1 being capable of forming somatic embryos was selected and its growth and isoquinoline alkaloid production was investigated. The illumination, temperature and nutrient medium composition greatly affected growth, cell morphology and alkaloid accumulation. The MAFF clone 1 cultured in Root Culture medium in the dark at 22 degrees C accumulated a high quantity of sanguinarine (652 micrograms/g dry weight) though the growth was poor (4.4 fold as fresh weight basis after 2 months of culture). The MAFF clone 1 cultured in a quarter macro salt strength Woody Plant medium under 14 h/day light at 22 degrees C developed into plantlets and accumulated significant quantity of codeine (648 micrograms/g dry wt) together with papaverine, noscapine, and sanguinarine. This clone was applied to a rotating drum fermenter (2 L working volume), and ca. 0.3 mg codeine and 0.06 mg sanguinarine were obtained after 4 weeks of culture. One quarter of the codeine produced was found in the culture medium.

Alkaloids↗

PubMedDate not supplied

Alkaloid biosynthesis in Papaver sp. cells in culture and during organogenesis.

In vitro cell cultures of two Papaver species, P. somniferum and P. bracteatum initiated from mature seeds were screened for their ability to produce alkaloids. Protocols for callus induction, somatic embryogenesis and organogenesis were established. The alkaloid contents were analysed by high-performance-liquid chromatography, thin-layer chromatography and spectrophotometric assays. Undifferentiated callus produced small amounts of sanguinarine, which increased with the degree of tissue differentiation. Embryogenic calli were maintained in culture for more than 2 years, retaining a high regeneration capability. Thin-layer chromatography analysis revealed variations in alkaloid spectrum between parallel cell lines. The morphinan alkaloid, thebaine, was found to be accumulated exclusively in morphogenous strains of P. bracteatum, and morphine was the major alkaloid in the spectrum of P. somniferum dedifferentiated callus. Regenerant plants synthesized thebaine and sanguinarine at the same level as juvenile plants grown from P. bracteatum seeds. We revealed differences in the ability to produce different types of alkaloids: seed-derived plants were able to accumulate thebaine while undifferentiated primary cell cultures produced only sanguinarine. The production of either sanguinarine and morphinan alkaloids are found in regenerants showing that both metabolic pathways were active in young plantlets.

Alkaloids↗

PubMed2002

[Effect of a fungal elicitor on levels of sanguinarine and polyphenoloxidase activity in a suspension culture of Papaver somniferum L].

The opium poppy (Papaver somniferum L.) is still a source for isolation of codeine and morphine. Cell cultures from this plant lose their ability to produce morphinans. Their major alkaloid is sanguinarine. The elicitation of the opium poppy cell cultures by fungal preparation lead to a nine-fold increase in the content of sanguinarine. The specific activity of polyphenoloxidase (PPO) was three-times higher in the elicited compared to the nonelicited cells. Two isoforms of PPO (Mr 63 kDa, 41 kDa) were identified in opium poppy cell cultures by PAGE. The number of PPO isoforms was not affected by elicitation. Phenyl-Sepharose CL-4B was used for affinity purification of PPO. In a single purification step the specific activity of PPO was enriched 14-fold.

Alkaloids↗

PubMedDate not supplied

Rapid semi-quantitative spot test for determination of thebaine and differentiation of Papaver bracteatum from P. orientale and P. pseudo-orientale.

The alkaloids, orientalidine, oripavine, thebaine, narceine, narceine, codeine, papaverine, isothebaine, alpenigenine and morphine react with a solution of sulfuric acid containing molybdate to give specific colors. Using the acid solution permitted the differentiation of Papaver bracteatum latex from P. orientale latex and P. pseudo-orientale latex.

Alkaloids↗

PubMed1992

[Flower bud differentiation and development of opium poppy (Papaver somniferum L.) II. Effects of daylength and temperature].

We investigated the effect of daylength (from 9 to 15 hours) and cultivation temperature (from about 13 to 25 degrees C) on flower bud differentiation of three strains of Papaver somniferum L. cv. Ikkanshu, which have been cultivated in Nayoro (Hokkaido), Tsukuba (Central Honshu) and Nagasaki (Kyushu) for the last a few decades. 1. The experiment on the effect of daylength on flowering revealed that the longer the photoperiod was, the earlier flowering occurred. 2. Flower bud differentiation was observed at temperatures of 20 degrees C or less but never at 25 degrees C, and it was more quickly induced at lower temperatures. Furthermore, we also found that the optimum temperature for flower bud development following differentiation was 20 degrees C. From these findings, we reached the conclusion that this species has thermosensitivity. 3. Flower bud differentiation clearly occurred later in the Nayoro strain than in the Nagasaki strain or the Tsukuba strain. This seems to indicate that the Nayoro strain is a different ecological type from other strains. 4. When we compared the size and dry weight of the capsules, which are known to be closely related to opium yield, the capsules of the Nagasaki and Tsukuba strains were considerably smaller and lighter than those of the Nayoro strain. This is attributable to the fact that flower bud differentiation occurred at an early stage before the achievement of sufficient vegetative growth in the Nagasaki and Tsukuba strains.

Light↗

PubMedDate not supplied

[Biosynthesis of poppy isoquinoline alkaloids in nature and in vitro culture. 1. Opium poppy (Papaver somniferum L.)].

The analysis of literature data on production of isoquinoline alkaloids by Papaver somniferum L. plants and cell cultures has been made. The relationship of morphinane alkaloids biosynthesis with the processes of tissue and cell differentiation are discussed. The information on enzymes and pathways of regulation of morphine and sanguinarine biosynthesis are presented. The data on sanguinarine and morphine physiological role are analyzed.

Alkaloids↗

PubMed2003

[Influence of fertilizers on yield and yield components of opium from Papaver somniferum Linn].

The effect of fertilizer on the yield and yield components of opium from Papaver somniferum L.cv.Ikkanshu were investigated from 1993 to 1995. The weight of opium per one capsule was tendency to increase in the order of peat moss > pulverized charcoal > compound fertilizer, but the differences among the results were not significant. Furthermore, no difference in the capsule weight per 100 m2 and the yields of opium and alkaloids per 100 m2 were detected. The significant difference was only observed when the data were compared among the weights and yields of different years. The difference among the yield of opium was mainly due to the weight of opium per one capsule. The weight of opium per one capsule showed a high correlation with capsule husk weight. The alkaloids contents in opium obtained with a different fertilizer application showed no difference. Morphine content at the first lancing was about 11%, and the value decreased with the order of lancing. On the contrary, the codeine and the thebaine content did not change during lancing and the value were 6-7% and 3%, respectively. The papaverine and the noscapine content decreased in the order of lancing.

Codeine↗

PubMedDate not supplied

[Variability of flavonol contents during floral morphogenesis in Papaver somniferum L].

We studied the contents of flavonols (kaempferol and quercetin) in the meristem of vegetative and generative apices of the main plant shoot in floral Papaver somniferum mutants, as well as in the normal plants at successive stages of flower development. Five stages of flower development were distinguished. Flavonols (kaempferol and quercetin) were present in all flower organs at all stages of floral morphogenesis we studied. However, their contents and distribution in different organs and at different stages of flower development markedly varied. No significant differences were found in the contents of flavonols in the meristems of vegetative and generative apices of the main shoot in the lines of floral mutants, as well as between the lines with different amounts of vegetative phytomeres. In the plants with normal flower structure, the contents of flavonols (kaempferol + quercetin) sharply increased with the beginning of differentiation of flower organs, i.e. from stage 3, to reach a maximum in the open flower, when gametogenesis is terminated and fertilization takes place. The level of flavonol contents in the petals (upper part) and stamen was at a maximum at all stages of flower development, while that in the gynaecium was at a minimum. The kaempferol: quercetin ratio shifted towards quercetin at successive stages of flower development, most significantly in the stamens. The involvement of flavonols in the regulation of floral morphogenesis at stages of flower organs differentiation and functioning is discussed.

Flavonols↗

PubMed1992

Increase in thebaine content of Papaver bracteatum Lindl. after colchicine treatment of seeds. Annual fluctuations in thebaine level of individual plants.

From colchicine-treated seeds of Papaver bracteatum Lindl. some poppy plants were obtained that developed capsules richer in thebaine than the controls. The individual poppies were analyzed for capsule thebaine content annually for eight successive years, the results revealing significant year-to-year differences. One of the poppies, X7, (ca 5% thebaine) developed capsules consisting partly of polyploid tissue during the first and second year. This plant was propagated vegetatively to give a series (the X7 series) of new P. bracteatum plants. The capsule thebaine content of these individuals differed markedly the first two years, whereupon the alkaloid production decreased and appeared to level out and reach a value still clearly higher than the controls (mean values 2.3% and 1.3%, respectively). From seeds of four of the thebaine-rich poppies of the X7 series, four new series of P. bracteatum plants were obtained. The capsule thebaine level of these was significantly lower than that of the mother plants.

Colchicine↗

PubMedDate not supplied

[Biosynthesis of poppy isoquinoline alkaloids in nature and in vitro culture. 2. Bracteum poppy (Papaver bracteatum Lindl.)].

Literature data and the data of the author's investigations on production of isoquinoline alkaloids by Papaver bracteatum Lindl. have been analyzed. Information on the methods of regulation and cell localization of morphine and sanguinarine biosynthesis is presented. The works studying differentiation processes in tissue cultures of bracteum poppy and relationship thereof with thebaine biosynthesis have been analyzed. Possible mechanism determining the induction of somatic embryos development and thebaine biosynthesis in the culture in vitro are proposed.

Alkaloids↗

PubMedDate not supplied

Thin-layer chromatography-densitometry and liquid chromatography analysis of alkaloids in leaves of Papaver somniferum under stress conditions.

The effect of stress conditions on the concentrations of secondary metabolites were examined during various developmental stages of Papaver somniferum plants. P. somniferum plants were grown in laboratory conditions (Budakalász). The experiment consisted of 22 treatments. Significantly different alkaloid contents can be observed under different stress conditions. In general, the alkaloid contents of plants are very low; therefore, a highly sensitive and reliable method has to be developed for analysis. The amount of alkaloids was measured by 2 separation and detection techniques. Accuracy of the thin-layer chromatography method for quantitative analysis is limited. Without purification of samples the background is too noisy. Column liquid chromatography is a sensitive and relatively inexpensive method that allows precise quantitative determination of the alkaloid content.

Alkaloids↗

PubMedDate not supplied

[Regulatory role of elements in the formation and accumulation of alkaloids in Papaver somniferum L. seedlings].

The effects of 12 elements on the formation and accumulation of isoquinolines were studied in opium poppy seedlings (Papaver somniferum L.). Three types of concentration dependences of the effects of the elements under study were determined. The elements served as activators (Co, Mo, W, Cr, and Cu) or inhibitors of these processes (B, Fe, V, Mn, and Ca). The molecular mechanisms of action of these regulators are discussed. The optimum concentrations of Co and Mo were tested under combined treatment conditions with these elements.

Alkaloids↗