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PubMedDate not supplied

Alkaloids of papaver genus IX. Alkaloids of Glaucium vitellinum Boiss and Buhse, population Seerjan and Glaucium pulchrum Stapf, population Elika.

Glaucium vitellinum Boiss and Buhse. population Seerjan was shown to contain three major alkaloids, isocorydine (0.44%), protopine (0.42%), dicentrine (0.24%), and four minor alkaloids, tetrahydropalmatine (0.13%), muramine (0.12%), bulbocapnine (0.06%) and glaucine (0.01%). Glaucium pulchrum Stapf popllation Elika was shown to contain two major alkaloids, corydine (0.3%) and bulbocapnine (0.18%) and three minor alkaloids N-methylindcarpine (0.1%), isocorydine (0.03%) and protopine (0.01%). N-methyllindcarpine was found for the first time in the Papaveraceae and tetrahydropalmatine was detected for the first time in Glaucium.

Alkaloids↗
PubMed1991

Changes in glutathione and cellular energy as potential mechanisms of papaverine-induced hepatotoxicity in vitro.

The purpose of this study was to elucidate the mechanism of hepatotoxicity of papaverine hydrochloride (papaver) in vitro. To evaluate the role of metabolism in the toxicity of papaver, cells were pretreated with SKF-525A or benzyl imidazole (cytochrome P450 system inhibitors) for 24 hr at 1 x 10(-5) or 1 x 10(-4) M, respectively, or with phenobarbital sodium (cytochrome P450 system inducer) for 3 days at 2 x 10(-3) M. Cells then were exposed to concentrations of papaver ranging from 1 x 10(-5) to 1 x 10(-3) M for 4 to 24 hr. Cytotoxicity was evaluated by enzyme leakage (lactate dehydrogenase) and by energy status of the cells (ATP/ADP). The role of biological reactive intermediates in the toxicity of papaver was investigated by measuring changes in cellular reduced glutathione levels (GSH), by inhibiting GSH synthesis, and by determining the production of lipid peroxidation (LPX). Papaverine produced concentration- and time-dependent increases in enzyme leakage, with significant effects occurring by the 8-hr exposure period. Pretreatment with SKF-525A or benzyl imidazole increased enzyme leakage induced by papaver especially at a later time frame (24 hr), but pretreatment with phenobarbital delayed the onset of cytotoxicity from 8 to 12 hr. Decreases in GSH levels paralleled the time course of enzyme leakage. However, the administration of buthionine sulfoximine to cell cultures dramatically decreased the time by which papaver induced cellular injury (2 hr vs 8 hr). Changes in cellular energy status (ATP/ADP) were also detected earlier than enzyme leakage (4 hr vs 8 hr). In contrast, no significant production of lipid peroxidation was noted in papaver-treated cultures. We suggest that the mechanism of papaver-induced hepatotoxicity may be related to alterations in glutathione balance of the cells and to disruption of energy homeostasis.

Adenosine Diphosphate↗
PubMed1990

Toxicity assessment of papaverine hydrochloride and papaverine-derived metabolites in primary cultures of rat hepatocytes.

The present study was undertaken to assess and compare the toxic effects of papaverine hydrochloride and its metabolites. Primary cell cultures of rat hepatocytes were treated with papaverine (papaver), 3'-O-desmethyl (3'-OH), 4'-O-desmethyl (4'-OH), and 6-O-desmethyl (6-OH) papaverine at 1 x 10(-5), 1 x 10(-4), and 1 x 10(-3) M for 4, 8, 12, and 24-h periods. Cell injury was determined by: a) cell viability using the trypan blue exclusion test; b) cytosolic enzyme leakage of lactate dehydrogenase and aspartate aminotransferase; c) morphologic alterations; and d) lactate:pyruvate (L:P) ratios. Cell cultures showed concentration- and time-dependent toxic responses. For example, a decrease in cell viability and an increase in enzyme leakage were observed after cell treatment with 1 x 10(-4) and 1 x 10(-3) M papaver for 8 h; 1 x 10(-3) M 6-OH papaverine for 8 h and 1 x 10(-4) M for 24 h; and 1 x 10(-3) M 4'-OH papaverine for 24 h (P less than 0.05). Furthermore, changes in morphology correlated to cell viability and enzyme release in those cultures treated with papaver, 4'-OH and 6-OH papaverine. Some of these changes included size deformation, cell detachment from the dishes, and cell necrosis. On the other hand, an increase in L:P ratios (P less than 0.05) was detected with papaver as early as 8 h with 1 x 10(-4) and 1 x 10(-3) M and 12 h with 1 x 10(-5) M; 6-OH showed an increase in L:P ratios at 8 h with 1 x 10(-3) M and 12 h with 1 x 10(-4) M; these changes were evident with with 4'-OH at 12 h with 1 x 10(-3) M. In contrast, cells treated with 3'-OH papaverine did not show significant damage with any time period and concentration used in this study. The results of this study indicate that papaverine-derived metabolites are less cytotoxic than its parent compound, papaver. The toxicity was ranked as follows: papaver greater than 6-OH greater than 4'-OH greater than -3'-OH.

Animals↗
PubMed2001

Somatic Embryogenesis, Rhizogenesis, and Morphinan Alkaloids Production in Two Species of Opium Poppy.

A study of somatic embryogenesis and rhizogenesis and their influence on production of morphinan alkaloids on two species of opium poppy is presented. We identified the ratios of auxin and cytokinin that caused somatic embryogenesis and rhizogenesis in hypocotyl and cotyledons of Papaver somniferum album and Papaver orientale splendidissimum. The hypocotyls and cotyledons both show somatic embryogenesis in Papaver somniferum album whereas only the cotyledons were embryogenic in Papaver orientale splendidissimum. For rhizogenesis, the most important response is on the cotyledons and leaves in these two species. Histology showed characteristic stages of somatic embryo: Globular, cotyledonous, and heart cotyledonary. High performance liquid chromatography analysis showed that the roots of both species synthesized codeine, thebaine, and papaverine. Morphine was only detected in aerial parts of Papaver somniferum album. Codeine and thebaine were detected in the rhizogenous but no embryonic callus. These results suggest that root organogenesis is causally related to alkaloid biosynthesis.

Journal Article↗
PubMed1997

Cloning and heterologous expression of NADPH-cytochrome P450 reductases from the Papaveraceae.

Cytochrome P450 reductase was purified to homogeneity from cell suspension cultures of the opium poppy Papaver somniferum, the enzyme was characterized (K(m) cytochrome c, 8.3 microM; K(m) NADPH, 4.2 microM; pH optimum, 8.0; M(r), 80 kDa), and the amino acid sequence of internal peptides was determined. Partial cDNA clones from P. somniferum and from Eschscholzia californica (California poppy) were then generated using the polymerase chain reaction and were used as hybridization probes to isolate full-length cDNAs. The Papaver and Eschscholzia cytochrome P450 reductases are 63% identical at the nucleotide level and 69% identical at the amino acid level. SDS-PAGE of the purified native P. somniferum enzyme as well as genomic DNA gel blot analysis indicate that two cytochrome P450 reductase isoforms are present in each species. This evidence is also supported by translation of nucleotide sequences obtained from the PCR-generated partial cDNAs and the full-length cDNAs isolated from lambda libraries. The Papaver and Eschscholzia cytochrome P450 reductases were functionally expressed in the yeast Saccharomyces cerevisiae and in the insect cell culture Spodoptera frugiperda Sf9. Coexpression of cytochrome P450 reductase with the C-O phenol coupling cytochrome P450 of bisbenzylisoquinoline alkaloid biosynthesis in Berberis stolonifera, berbamunine synthase (CYP80A1), in insect cell culture resulted in an alteration of the product profile as compared to that obtained by expression of berbamunine synthase in the absence of plant reductase.

Alcohol Oxidoreductases↗
PubMed1977

Large vessel impedance in peripheral atherosclerosis.

Recent studies based on an animal model of arterial stenosis have shown that large vessel impedance (ZL), determined from the high-frequency vascular hydraulic impedance of a stenotic femoral arterial bed, is linearly related to the large vessel stenotic resistance, and somewhat independent of distal (small vessel) arteriolar resistance. To determine the applicability of these findings on human subjects with stenotic atherosclerotic lesions, ZL was determined in the femoral arteries of 17 patients (at the time of reconstructive operations) with no (N), mild (AS), and severe (occlusive) atherosclerotic (ASO) disease, and in a group of patients before and after femoral-to-popliteal bypass procedures (FEM-POP). Data were collected under steady-state conditions (SS) and during peak flow after a 30 mg bolus intra-arterial administration of papaverine hydrochloride (PAPAV). The ZL was found to be significantly greater (P less than 0.05) for the ASO group than for the N group at SS and after PAPAV administration. There was no significant difference in ZL between the SS and PAPAV conditions for all groups. The ZL decreased significantly (P less than 0.01) from the pre- to post-bypass conditions (with and without the stenosis), at steady-state and after papaverine hydrochloride administration. Large vessel impedance appears to provide a reliable index of the severity of a large vessel atherosclerotic stenosis, and is indpendent of small vessel resistance in humans. These findings are consistent with those of previous experimental animal studies.

Adult↗
PubMed2006

Poppy alkaloid profiling by electrospray tandem mass spectrometry and electrospray FT-ICR mass spectrometry after [ring-13C6]-tyramine feeding.

Papaver alkaloids play a major role in medicine and pharmacy. In this study, [ring-(13)C(6)]-tyramine as a biogenetic precursor of these alkaloids was fed to Papaver somniferum seedlings. The alkaloid pattern was elucidated both by direct infusion high-resolution ESI-FT-ICR mass spectrometry and liquid chromatography/electrospray tandem mass spectrometry. Thus, based on this procedure, the structure of about 20 alkaloids displaying an incorporation of the labeled tyramine could be elucidated. These alkaloids belong to different classes, e.g. morphinan, benzylisoquinoline, protoberberine, benzo[c]phenanthridine, phthalide isoquinoline and protopine. The valuable information gained from the alkaloid profile demonstrates that the combination of these two spectrometric methods represents a powerful tool for evaluating biochemical pathways and facilitates the study of the flux of distant precursors into these natural products.

Alkaloids↗
PubMed2004

Phylogenetic analysis of the downy mildew pathogen of oilseed poppy in Tasmania, and its detection by PCR.

Downy mildew of oilseed poppy (Papaver somniferum) has become a serious disease issue for the Tasmanian poppy industry since its first record in 1996. Previous reports have reported the pathogen as Peronospora arborescens, which is differentiated from the related species P. cristata, also known to infect Papaver spp., by conidium dimensions alone. This study investigated the taxonomic status of the downy mildew pathogen, using both morphological characters and molecular analysis of the internal transcribed spacer (ITS) region of the ribosomal DNA (rDNA). The inherent variability of conidium dimensions made differentiation of species difficult. Sequence homology and phylogenetic analyses of the ITS region showed the pathogen to be more closely related to P. cristata than P. arborescens. It is therefore proposed that downy mildew of oilseed poppy in Tasmania be reattributed to the pathogen P. cristata. In addition to this work, PCR primers have been developed for the specific detection of the downy mildew pathogen in Tasmania.

DNA, Fungal↗
PubMed2003

Anti-ulcerogenic activity of some plants used as folk remedy in Turkey.

Five herbal remedies used as gastroprotective crude drugs in Turkey were assessed for anti-ulcerogenic activity using the EtOH-induced ulcerogenesis model in rat. The crude drugs investigated comprises fruits of Elaeagnus angustifolia L. (Elaeagnaceae), fresh fruits of Hibiscus esculentus L. (Malvaceae), fresh roots of Papaver rhoeas L. (Papaveraceae), leaves of Phlomis grandiflora H.S. Thomson (Lamiaceae) and fresh fruits of Rosa canina L. (Rosaceae). Extracts were prepared according to the traditional indications of use. Under our experimental conditions, all extracts exhibited statistically significant gastroprotective effect with better results for Phlomis grandiflora and Rosa canina (100%). At the concentration under study, both crude drugs were more effective than the reference compound misoprostol at 0.4 mg/kg. Even the weakest anti-ulcerogenic effect observed for Papaver rhoeas roots was found statistically potent (95.6%). Histopathological studies confirmed the results of the in vivo test.

Animals↗
PubMed2000

Naturally occurring antinociceptive substances from plants.

Despite the progress that has occurred in recent years in the development of therapy, there is still a need for effective and potent analgesics, especially for the treatment of chronic pain. One of the most important analgesic drugs employed in clinical practice today continues to be the alkaloid morphine. In this review, emphasis will be given to the important contribution and the history of Papaver somniferum, Salix species, Capsicum species and Cannabis sativa in the development of new analgesics and their importance in the understanding of the complex pathways related to electrophysiological and molecular mechanisms associated with pain transmission. Recently discovered antinociceptive substances include alkaloids, terpenoids and flavonoid. Plant-derived substances have, and will certainly continue to have, a relevant place in the process of drug discovery, particularly in the development of new analgesic drugs.

Analgesics↗
PubMed1997

Ca2+ oscillations in plant cells: initiation by rapid elevation in cytosolic free Ca2+ levels.

Temporal increases in intracellular [Ca2+] are now recognized to be key triggers for a wide range of important physiological events in eukaryotic cells. In mammalian cells, signal-induced Ca2+-elevations have been found to be of a pulsatile nature and Ca2+ spikes display a high degree of spatiotemporal complexity. In plant cells a similar picture is beginning to emerge. To investigate the occurrence of pulsatile Ca2+ signals in plant cells we studied alterations of [Ca2+] in the tip region of pollen tubes from poppy (Papaver rhoeas). Time-Resolved Laser Scanning Confocal Microscopy of pollen tubes microinjected with the Dextran-linked Ca2+-indicator dyes Calcium Green or Indo-1 revealed that highly regular Ca2+ oscillations occur in these cells. We further demonstrate that artificial elevation of cytosolic Ca2+ by photolysis of caged-Ca2+ (Nitr-5) can trigger the onset of oscillations.

Calcium↗