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1.
J Agric Food Chem ; 68(3): 884-891, 2020 Jan 22.
Artigo em Inglês | MEDLINE | ID: mdl-31825610

RESUMO

Having a long history of traditional medicinal applications, Papaver somniferum is also known as a source of various pharmacologically highly active opiates. Consequently, their detection from plant extracts is an important analytical task and generally addressed by methods of GC-MS and LC-MS. However, opiates do also show structural similarities to matrix molecules used in matrix-assisted laser desorption ionization (LDI) and may therefore ionize upon simple laser irradiation. Following this analytical approach, the present work thoroughly evaluated the direct detection of opiates by matrix-free LDI in crude extracts of P. somniferum. The method facilitated the identification of 10 reported opiates by their molecular formulas without any chromatographic prepurification. Moreover, a principal component analysis based on LDI-MS data permitted the correct grouping of all extracts according to their inherent chemistry. Concluding experiments on serial dilutions of thebaine further evaluated potential quantitative applications of the method. Overall results highlight the promising potential of LDI-MS for the swift detection of opiates in complex mixtures.


Assuntos
Alcaloides Opiáceos/química , Papaver/química , Extratos Vegetais/química , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz/métodos , Lasers , Estrutura Molecular , Espectrometria de Massas por Ionização e Dessorção a Laser Assistida por Matriz/instrumentação
2.
Food Chem ; 309: 125564, 2020 Mar 30.
Artigo em Inglês | MEDLINE | ID: mdl-31670127

RESUMO

Opium alkaloids such as morphine and thebaine occur in the latex of Papaver somniferum varieties. Some varieties are used for both, pharmaceutical opium alkaloid generation and poppy seed production for food use. Poppy seeds can be contaminated with opium alkaloid-containing latex, e.g. during harvesting. In recent years, poppy seed contamination with opium alkaloids, including thebaine, gave repeatedly reasons for concern in Europe. So far, risk assessments regarding opium alkaloids in poppy seeds were mainly based on the morphine level, whereas other opium alkaloids thereunder thebaine could not be finally evaluated due to lack of data. However, available limited data indicate that thebaine exhibits a higher acute toxic potential than morphine. Therefore, exposure to thebaine by consumption of poppy seed-containing food could pose a health risk. Here, we discuss the recent knowledge regarding thebaine's toxicological profile available for the assessment of potential health risks associated with its consumption via food.


Assuntos
Tebaína/toxicidade , Animais , Humanos , Látex/química , Papaver/química , Sementes/química , Tebaína/efeitos adversos
3.
Chem Commun (Camb) ; 55(90): 13594-13597, 2019 Nov 07.
Artigo em Inglês | MEDLINE | ID: mdl-31657378

RESUMO

Indole and the anthocyanin orientalin proceed through a unique cascade sequence that leads to nudicaulins I and II in 92% yield. This biomimetic synthesis confirms the biosynthesis proposal for these structurally unprecedented flavoalkaloids that play a key role in the colour range displayed by the Iceland poppy.


Assuntos
Materiais Biomiméticos/síntese química , Papaver/química , Pigmentos Biológicos/síntese química , Materiais Biomiméticos/química , Islândia , Estrutura Molecular , Pigmentos Biológicos/química
4.
Fitoterapia ; 139: 104371, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31629051

RESUMO

Extrusion of drugs or drug-like compounds through bacterial efflux pumps is a serious health issue that leads to loss in drug efficacy. Combinatorial therapies of low-efficacy drugs with efflux pump inhibitors may help to restore the activities of such drugs. In this quest, natural products are attractive molecules, since in addition to their wide range of bioactivities they may inhibit efflux pumps. The current work repurposed the bioactive alkaloid roemerine as a potential efflux pump inhibitor. In Bacillus subtilis, both Bmr and BmrA, belonging to the major facilitator and the ATP-binding cassette superfamilies, respectively, were found to be inhibited by roemerine. Scanning electron microscopy and RNA-Seq analyses showed that it potentiated the effect of berberine. Growth rates and checkerboard assays confirmed the synergy of roemerine and berberine and that roemerine prevented berberine efflux by inhibiting Bmr. Transport assays with inverted membrane vesicles prepared from Escherichia coli overexpressing BmrA showed that increasing roemerine concentration decreased the transport of doxorubicin, the BmrA substrate, confirming that roemerine may also be considered as an inhibitor of BmrA. Thus, these findings suggest that conjugation of roemerine to substrates of efflux pumps, Bmr and BmrA, may help to potentiate the activity of their drug substrates.


Assuntos
Antibacterianos/farmacologia , Aporfinas/farmacologia , Proteínas de Bactérias/antagonistas & inibidores , Alcaloides/farmacologia , Bacillus subtilis/efeitos dos fármacos , Berberina/farmacologia , Transporte Biológico , Reposicionamento de Medicamentos , Sinergismo Farmacológico , Escherichia coli/efeitos dos fármacos , Proteínas de Membrana Transportadoras , Testes de Sensibilidade Microbiana , Estrutura Molecular , Papaver/química , Componentes Aéreos da Planta/química , Turquia
5.
Mater Sci Eng C Mater Biol Appl ; 103: 109740, 2019 Oct.
Artigo em Inglês | MEDLINE | ID: mdl-31349401

RESUMO

To overcome the disadvantages of chemical and physical methods, phyto-fabricated nanoparticles attained great attention due to their multifarious applications. Here we successfully demonstrated Papaver somniferum L. mediated green synthesis of lead oxide (PbO) and iron oxide (Fe2O3) nanoparticles. Characterization of nanoparticles involved techniques including X-ray diffraction (XRD), Fourier transform infrared spectroscopy (FT-IR) and energy dispersive X-ray (EDX) associated with scanning electron microscopy (SEM). XRD analysis confirmed the phase identification and crystalline nature. FTIR analysis confirmed the capping of nanoparticles by plants' phytochemicals. SEM revealed morphological features of PbO and Fe2O3 with size of nanoparticles being 23 ±â€¯11 nm and 38 ±â€¯13 nm, respectively. The elemental composition of the nanoparticles was confirmed by EDX. Both bacterial and fungal isolates showed susceptibility towards PbO and Fe2O3 NPs. Both the NPs also showed considerable total antioxidant potential, free radical scavenging potential and reducing power. Insignificant level of α-amylase for both NPs was observed. Fe2O3 NPs showed superior biocompatibility with human RBCs as compared to PbO whereas PbO showed more potent anti-cancer activity as compared to Fe2O3 NPs. Overall our study concluded that both NPs played vital role in multiple biological assays however, extensive research focused on cytotoxic evaluation of NPs in-vivo is required.


Assuntos
Compostos Férricos/química , Chumbo/química , Nanopartículas Metálicas/química , Óxidos/química , Papaver/metabolismo , Antibacterianos/química , Antibacterianos/farmacologia , Antifúngicos/química , Antifúngicos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Avaliação Pré-Clínica de Medicamentos , Estabilidade de Medicamentos , Eritrócitos/efeitos dos fármacos , Hemolíticos/química , Hemolíticos/farmacologia , Células Hep G2 , Humanos , Hipoglicemiantes/química , Hipoglicemiantes/farmacologia , Nanopartículas Metálicas/uso terapêutico , Papaver/química , Espectroscopia de Infravermelho com Transformada de Fourier , Difração de Raios X , alfa-Amilases/antagonistas & inibidores , alfa-Amilases/metabolismo
6.
Forensic Sci Int ; 302: 109865, 2019 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-31279278

RESUMO

Consumption of curry containing poppy seeds has raised an issue concerning the opiate content in the urine that might exceed the cut-off value (300ng/mL). The main objective of this study was to examine the morphine and codeine contents in the urine of the consumers after partaking poppy seed-enriched curry in. The volunteers were asked to partake: (a) a single meal and their urines were collected within 24h, or (b) Two meals a day for three consecutive days and their urines were collected within 72h. Two different dosages were also tested in this study: (a) low dosage: 1g/100ml curry (containing 138µg of morphine and 66µg of codeine) and (b) high dosage: 5g/100ml curry (containing 690µg of morphine and 330µg of codeine). The subjects were randomised into the groups using the method of stratified randomization with age and gender groups as covariates. A total of 6 subjects was allocated for each group and placebos were used as control. Results showed that all subjects who consumed low dosage of poppy seeds either in single meal or multiple meals experiment were found negative. However, 1 out of 6high dosage subjects was confirmed positive at a period of 3-6h after the consumption of curry in the single meal study. This outlier maybe due to the lack of water consumption after consuming the curry, thus the low volume of urine was collected and the opiate was concentrated in the urine. On the other hand, 5 out of 6high dosage subjects in the multiple meals experiment were found positive. Majority of these subjects were found positive on the second and third day of the experiment after the second curry meal was consumed. The outlier (negative) in this group might be due to the high consumption of water throughout the experiment and the subject's urine volumes and frequency of urine collection were much higher compared to other subjects. From the result of this study, it can be concluded that partaking high dosages of poppy seed in curry could give a positive response (>300ng/ml+uncertainty of measurement) in the urine, and the water consumption after partaking curry has significant influence for the opiate contents in the urine.


Assuntos
Codeína/urina , Refeições , Morfina/urina , Papaver/química , Sementes/química , Adulto , Erros de Diagnóstico/prevenção & controle , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Malásia , Masculino , Pessoa de Meia-Idade , Transtornos Relacionados ao Uso de Opioides/diagnóstico , Distribuição Aleatória , Detecção do Abuso de Substâncias , Adulto Jovem
7.
BMC Complement Altern Med ; 19(1): 90, 2019 Apr 29.
Artigo em Inglês | MEDLINE | ID: mdl-31036001

RESUMO

BACKGROUND: Papaver nudicaule belongs to the Papaveraceae family, which is planted as an annual herbaceous species generally for ornamental purpose. Papaver rhoeas in the same family has been reported to have various pharmacological activities such as antioxidant and analgesic effects. In contrast, little is known about the pharmacological activity of Papaver nudicaule. In this study, the anti-inflammatory activity of Papaver nudicaule extracts and the action mechanisms were investigated in RAW264.7 macrophage cells. METHODS: To investigate the anti-inflammatory activity of five cultivars of Papaver nudicaule with different flower color, samples were collected from their aerial parts at two growth stages (60 and 90 days) and their ethanol extracts were evaluated in the lipopolysaccharide (LPS)-treated RAW264.7 cells by measuring nitric oxide (NO) and prostaglandin E2 (PGE2) levels. Interleukin 1-beta (IL-1ß), Interleukin-6 (IL-6) and Tumor necrosis factor alpha (TNF-α) production were also analyzed by RT-PCR and multiplex assays. Nuclear Factor-kappa-light-chain-enhancer of activated B cells (NF-κB) and Signal transducer and activator of transcription 3 (STAT3) signaling pathways were examined using western blotting and luciferase reporter assays to reveal the action mechanism of Papaver nudicaule extracts in their anti-inflammatory activity. RESULTS: All of the Papaver nudicaule extracts were effective in reducing the LPS-induced NO, which is an important inflammatory mediator, and the extract of Papaver nudicaule with white flower collected at 90 days (NW90) was selected for further experiments because of the best effect on reducing the LPS-induced NO as well as no toxicity. NW90 lowered the LPS-induced PGE2 level and decreased the LPS-induced Nitric oxide synthase 2 (NOS2) and Cyclooxygenase 2 (COX2). In addition, NW90 reduced the LPS-induced inflammatory cytokines, IL-1ß and IL-6. Furthermore, NW90 inhibited the LPS-induced activation of NF-κB and STAT3. CONCLUSIONS: These results indicate that NW90 may restrain inflammation by inhibiting NF-κB and STAT3, suggesting the potential therapeutic properties of Papaver nudicaule against inflammatory disease.


Assuntos
Anti-Inflamatórios/farmacologia , NF-kappa B/metabolismo , Papaver/química , Extratos Vegetais/farmacologia , Fator de Transcrição STAT3/metabolismo , Animais , Anti-Inflamatórios/química , Sobrevivência Celular/efeitos dos fármacos , Inflamação/induzido quimicamente , Lipopolissacarídeos/efeitos adversos , Macrófagos/efeitos dos fármacos , Macrófagos/metabolismo , Camundongos , Óxido Nítrico/metabolismo , Extratos Vegetais/química , Células RAW 264.7 , Transdução de Sinais/efeitos dos fármacos
8.
Forensic Sci Int ; 295: 121-127, 2019 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-30579243

RESUMO

Papaver somniferum (opium poppy) is one of the world's oldest medicinal plants which are widely used for medicinal, nutritive and scientific purposes. Turkey is one of the major legal opium poppy producer countries in the world and the seed paste of the poppies is consumed in great deal, even more than 100g per meal. The main objective of this study is to investigate the influence of poppy seed paste ingestion on urine tests for opiates whether or not could lead to opiate positive urine test results. For this purpose, a variety of poppies were used and the morphine content of white, yellow and blue-black poppies were determined as 1.9, 4.0 and 2.6mg/kg, respectively. 100g of these seed pastes were consumed in the breakfast by ten healthy adults enrolled in the study over three days and urine samples were collected before and after the breakfast. Opiate screening analysis was carried out by enzyme immunoassay method and the results were evaluated by two different cut-off values (300 and 2000ng/mL). Morphine confirmation analysis was made by GC-MS system and the chromatographic method was validated in terms of selectivity, extraction efficiency, linearity (25-2000ng/ml), intra-assay precision, accuracy, limit of detection (LOD) and limit of quantitation (LOQ) (3 and 10ng/ml), carryover, matrix effect, dilution integrity and stability. According to cut-off value 300ng/ml, opiate concentrations were found positive up to 48h. For cut-off value 2000ng/mL; this time was up to 12h in collected urine samples after consumption of three different colored poppy seed pastes. In all urine samples, thebaine was detected while the heroin abuse metabolite 6-acetyl morphine (6-AM) was not. Urine drug testing legislation was revised on 2016 in Turkey and opiate screening cut-off values increased from 300 to 2000ng/mL. Overall results have shown that poppy seed paste as food consumption could lead to opiate positive urine test result even if increased cut off levels are used. It can also be deduced that thebaine can be taken as supportive biomarker for poppy seed paste consumption. Awareness of interpretation of urine test results and defining the procedures especially for forensic drug testing must be done in legal aspect to ensure justice for each individual (workplace, traffic, court etc.).


Assuntos
Alimentos , Morfina/urina , Papaver/química , Sementes/química , Adulto , Feminino , Cromatografia Gasosa-Espectrometria de Massas , Humanos , Técnicas Imunoenzimáticas , Limite de Detecção , Masculino , Fatores de Tempo , Turquia
9.
Drug Metab Dispos ; 47(2): 164-172, 2019 02.
Artigo em Inglês | MEDLINE | ID: mdl-30478158

RESUMO

The antitussive agent noscapine has been shown to inhibit the proliferation of cancer cells by disruption of tubulin dynamic. However, the efficacy of several anticancer drugs that inhibit tublin dynamics (vinca alkaloids and taxanes) is reduced by the multidrug resistance phenotype. These compounds are substrates for P-glycoprotein (P-gp)-mediated extrusion from cells. Consequently, the antiproliferative activity of noscapine and a series of derivatives was measured in drug-sensitive and drug-resistant cells that overexpress P-gp. None of the noscapine derivatives displayed lower potency in cells overexpressing P-gp, thereby suggesting a lack of interaction with this pump. However, the cellular efflux of a fluorescent substrate by P-gp was potently inhibited by noscapine and most derivatives. Further investigation with purified, reconstituted P-gp demonstrated that inhibition of P-gp function was due to direct interaction of noscapine derivatives with the transporter. Moreover, coadministration of vinblastine with two of the noscapine derivatives displayed synergistic inhibition of proliferation, even in P-gp-expressing resistant cell lines. Therefore, noscapine derivatives offer a dual benefit of overcoming the significant impact of P-gp in conferring multidrug resistance and synergy with tubulin-disrupting anticancer drugs.


Assuntos
Protocolos de Quimioterapia Combinada Antineoplásica/farmacologia , Resistência a Múltiplos Medicamentos/efeitos dos fármacos , Resistencia a Medicamentos Antineoplásicos/efeitos dos fármacos , Neoplasias/tratamento farmacológico , Noscapina/farmacologia , Subfamília B de Transportador de Cassetes de Ligação de ATP/isolamento & purificação , Subfamília B de Transportador de Cassetes de Ligação de ATP/metabolismo , Protocolos de Quimioterapia Combinada Antineoplásica/uso terapêutico , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Células MCF-7 , Neoplasias/patologia , Noscapina/análogos & derivados , Papaver/química , Proteínas Recombinantes/isolamento & purificação , Proteínas Recombinantes/metabolismo , Moduladores de Tubulina/farmacologia , Moduladores de Tubulina/uso terapêutico , Vimblastina/farmacologia
10.
Analyst ; 143(21): 5127-5136, 2018 Oct 22.
Artigo em Inglês | MEDLINE | ID: mdl-30280166

RESUMO

A method has been developed for extracting poppy alkaloids from oily matrices, specifically lipid residues associated with archaeological ceramics. The protocol has been applied to fresh and artificially aged poppyseed oil and to residue from a Late Bronze Age Cypriot juglet in the collections of the British Museum. The juglet is of a type that has been linked with ancient trade in opium due to its poppy-head shape and wide distribution; it is a rare example of an intact vessel with contents sealed inside. Bulk analysis of the residue by GC-EI-MS and pyGC-EI-MS indicated a degraded plant oil and possible presence of papaverine. Analysis of the alkaloid extracts by HPLC-ESI-MS using both triple quadrupole and FTICR mass spectrometers detected the five primary opium alkaloids in fresh poppyseed oil and papaverine in most of the aged samples. Papaverine and thebaine were detected in the juglet residue, providing the first rigorous chemical evidence to support a link between this vessel type and opium, or at least poppies. The association of opium with oil raises new questions about the ancient purpose of the commodities within these vessels, and the low levels (ng g-1) of opiates detected in this unusually well-preserved residue shed doubt on the scope for their detection in more fragmentary ceramic remains (potsherds). Papaverine was found to exhibit challenging carryover behaviour in all the analytical methods used in this study. The phenomenon has not been reported before and should be considered in future analyses of this analyte in all application areas.


Assuntos
Cerâmica/análise , Ópio/análise , Papaverina/análise , Óleos Vegetais/análise , Extração em Fase Sólida/métodos , Tebaína/análise , Arqueologia/métodos , Cromatografia Líquida de Alta Pressão/métodos , Cromatografia Gasosa-Espectrometria de Massas/métodos , Limite de Detecção , Papaver/química , Espectrometria de Massas por Ionização por Electrospray/métodos
11.
Artigo em Inglês | MEDLINE | ID: mdl-30189375

RESUMO

Papaver species, well known for their alkaloids, have been used for the treatment of several diseases, such as inflammation, diarrhea, depression, and sleep disorders in certain parts of Anatolia. In this study, four Papaver species (P. lacerum, P. syriacum, P. glaucum and P. rhoeas) were collected from different localities of Turkey. Methanolic extracts were prepared from the aerial parts of the plants. A rapid analytical method was developed for the simultaneously quantitative analysis of two alkaloids, pronuciferine and roemerine, using liquid chromatography tandem mass spectrometry. Multiple reaction monitoring in the positive ionization mode was used for detection. Pronuciferine and roemerine were analyzed on a C18 column (2.1 × 50 mm, 3 µm) with the mobile phase run in the gradient mode with 0.1% formic acid in water (A) and 0.1% formic acid in acetonitrile at a flow rate of 0.3 mL/min. The transitions 312.1→283.1 m/z and 280.0→249.0 m/z were used to monitor pronuciferine and roemerine, respectively. The assay was linear in the concentration range of 0.01 µg/mL to 1 µg/mL (r = 0.996 for roemerine, r = 0.998 for pronuciferine). The validation studies revealed that the method was linear, sensitive, accurate, precise, selective, repeatable, robust, and rugged. Finally, the developed method was applied to quantify pronuciferine and roemerine in the selected species. The amounts of pronuciferine and roemerine were respectively found as 8.5 to 48 µg/g and 4.4 to 43,000 µg/g.


Assuntos
Alcaloides/análise , Cromatografia Líquida/métodos , Papaver/química , Espectrometria de Massas por Ionização por Electrospray/métodos , Compostos de Espiro/análise , Alcaloides/química , Alcaloides/isolamento & purificação , Limite de Detecção , Modelos Lineares , Extratos Vegetais/química , Reprodutibilidade dos Testes , Compostos de Espiro/química , Compostos de Espiro/isolamento & purificação , Espectrometria de Massas em Tandem/métodos
12.
J Biosci ; 43(2): 391-405, 2018 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-29872026

RESUMO

Here, a comprehensive endeavor is made to simultaneously scrutinize spatiotemporal oscillations of three imperative morphinan alkaloids (i.e. thebaine, codeine, and morphine) alongside dynamic transcriptional patterns of TYDC, SalAT, COR, T6ODM, and CODM genes in different tissues of Papaver somniferum (i.e. root, bottom part of stem, upper part of stem, leaf, capsule wall, and capsule content) over five distinguished ontogenic stages (i.e. rosette, bud initiation, pendulous bud, flowering, and lancing). Apart from bottom stem and leaf, the maximum thebaine content occurred in lancing stage, while its minimum content did not follow a systematic rhythm, either among six tissues or five various sampling times. Regarding codeine, excepting upper stem, the highest ratios of codeine were observed at flowering and lacing stages, while negligible amounts were overall detected at early stages of plant growth like rosette. Considering morphine, apart from upper stem, it appears that late ontogeneic times including lancing and flowering are the most appropriate phases to achieve high amounts of morphine, while at early stages the aforesaid alkaloid possessed lower accumulation. Furthermore, all the five genes under study, overall, exhibited a variety of transcript levels either among six tissues or five various sampling times. Interestingly, a connection occurred between transcript ratio of SalAT and thebaine content, suggesting that thebaine biosynthesis is coordinated tightly by the enzymatic function of SalAT enzyme. Meanwhile, despite low magnitudes of T6ODM and CODM transcripts in the root-harvested samples at pendulous bud and flowering stages, both codeine and morphine were surprisingly in acceptable quantities, plausibly owing to the translocation of both alkaloids from the producing (source) tissues to the roots (sink), known as a phenomenon of 'source-to-sink transportation'. The results, altogether, could provide us enough information in acquiring new insights towards potential impacts of spatiotemporal oscillations on the magnitudes of all the above-mentioned alkaloids alongside transcription ratios of the key genes in opium poppy.


Assuntos
Alcaloides/genética , Dopa Descarboxilase/genética , Morfina/química , Papaver/genética , Proteínas de Plantas/genética , Tirosina Descarboxilase/genética , Alcaloides/química , Flores/química , Flores/genética , Regulação da Expressão Gênica de Plantas , Morfina/metabolismo , Papaver/química , Folhas de Planta/química , Folhas de Planta/genética , Caules de Planta/química , Caules de Planta/genética
13.
J Sep Sci ; 41(12): 2517-2527, 2018 Jun.
Artigo em Inglês | MEDLINE | ID: mdl-29607619

RESUMO

Papaver plants can produce diverse bioactive alkaloids. Papaver rhoeas Linnaeus (common poppy or corn poppy) is an annual flowering medicinal plant used for treating cough, sleep disorder, and as a sedative, pain reliever, and food. It contains various powerful alkaloids like rhoeadine, benzylisoquinoline, and proaporphine. To investigate and identify alkaloids in the aerial parts of P. rhoeas, samples were collected at different growth stages and analyzed using liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry. A liquid chromatography with mass spectrometry method was developed for the identification and metabolite profiling of alkaloids for P. rhoeas by comparing with Papaver somniferum. Eighteen alkaloids involved in benzylisoquinoline alkaloid biosynthesis were used to optimize the liquid chromatography gradient and mass spectrometry conditions. Fifty-five alkaloids, including protoberberine, benzylisoquinoline, aporphine, benzophenanthridine, and rhoeadine-type alkaloids, were identified authentically or tentatively by liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry in samples taken during various growth stages. Rhoeadine alkaloids were observed only in P. rhoeas samples, and codeine and morphine were tentatively identified in P. somniferum. The liquid chromatography coupled with quadrupole time-of-flight tandem mass spectrometry method can be a powerful tool for the identification of diverse metabolites in the genus Papaver. These results may help understand the biosynthesis of alkaloids in P. rhoeas and evaluate the quality of this plant for possible medicinal applications.


Assuntos
Alcaloides/química , Cromatografia Líquida/métodos , Papaver/química , Extratos Vegetais/química , Espectrometria de Massas em Tandem/métodos , Componentes Aéreos da Planta/química , Plantas Medicinais/química
15.
Sci Rep ; 8(1): 2590, 2018 02 07.
Artigo em Inglês | MEDLINE | ID: mdl-29416103

RESUMO

This study is the first to report the successful development of a method to extract opium poppy (Papaver somniferum L.) DNA from heroin samples. Determining of the source of an unknown heroin sample (forensic geosourcing) is vital to informing domestic and foreign policy related to counter-narcoterrorism. Current profiling methods focus on identifying process-related chemical impurities found in heroin samples. Changes to the geographically distinct processing methods may lead to difficulties in classifying and attributing heroin samples to a region/country. This study focuses on methods to optimize the DNA extraction and amplification of samples with low levels of degraded DNA and inhibiting compounds such as heroin. We compared modified commercial-off-the-shelf extraction methods such as the Qiagen Plant, Stool and the Promega Maxwell-16 RNA-LEV tissue kits for the ability to extract opium poppy DNA from latex, raw and cooked opium, white and brown powder heroin and black tar heroin. Opium poppy DNA was successfully detected in all poppy-derived samples, including heroin. The modified Qiagen stool method with post-extraction purification and a two-stage, dual DNA polymerase amplification procedure resulted in the highest DNA yield and minimized inhibition. This paper describes the initial phase in establishing a DNA-based signature method to characterize heroin.


Assuntos
DNA de Plantas/química , DNA de Plantas/isolamento & purificação , Heroína/análise , Látex/análise , Ópio/análise , Papaver/química , Papaver/genética
16.
J Struct Biol ; 202(3): 229-235, 2018 06.
Artigo em Inglês | MEDLINE | ID: mdl-29408320

RESUMO

Thebaine 6-O-demethylase (T6ODM) from Papaver somniferum (opium poppy), which belongs to the non-heme 2-oxoglutarate/Fe(II)-dependent dioxygenases (ODD) family, is a key enzyme in the morphine biosynthesis pathway. Initially, T6ODM was characterized as an enzyme catalyzing O-demethylation of thebaine to neopinone and oripavine to morphinone. However, the substrate range of T6ODM was recently expanded to a number of various benzylisoquinoline alkaloids. Here, we present crystal structures of T6ODM in complexes with 2-oxoglutarate (T6ODM:2OG, PDB: 5O9W) and succinate (T6ODM:SIN, PDB: 5O7Y). Both metal and 2OG binding sites display similarity to other proteins from the ODD family, but T6ODM is characterized by an exceptionally large substrate binding cavity, whose volume can partially explain the promiscuity of this enzyme. Moreover, the size of the cavity allows for binding of multiple molecules at once, posing a question about the substrate-driven specificity of the enzyme.


Assuntos
Oxirredutases O-Desmetilantes/ultraestrutura , Papaver/enzimologia , Tebaína/química , Cristalografia por Raios X , Ácidos Cetoglutáricos/química , Metilação , Morfina/biossíntese , Morfina/química , Oxirredutases O-Desmetilantes/química , Papaver/química , Ácido Succínico/química
17.
Food Chem ; 242: 443-450, 2018 Mar 01.
Artigo em Inglês | MEDLINE | ID: mdl-29037712

RESUMO

A straightforward method to determine the content of six opium alkaloids (morphine, codeine, thebaine, noscapine, papaverine and narceine) in poppy seeds and bakery products was developed and validated down to a limit of quantification (LOQ) of 0.1mg/kg. The method was based on extraction with acetonitrile/water/formic acid, ten-fold dilution and analysis by LC-MS/MS using a pH 10 carbonate buffer. The method was applied for the analysis of 41 samples collected in 2015 in the Netherlands and Germany. All samples contained morphine ranging from 0.2 to 240mg/kg. The levels of codeine and thebaine ranged from below LOQ to 348mg/kg and from below LOQ to 106mg/kg, respectively. Sixty percent of the samples exceeded the guidance reference value of 4mg/kg of morphine set by BfR in Germany, whereas 25% of the samples did not comply with the limits set for morphine, codeine, thebaine and noscapine by Hungarian legislation.


Assuntos
Alcaloides/análise , Técnicas de Química Analítica/métodos , Culinária , Papaver/química , Sementes/química
18.
J Sep Sci ; 40(23): 4511-4520, 2017 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-28960752

RESUMO

A novel averagely linear-quantified fingerprint method was proposed and successfully applied to monitor the quality consistency of alkaloids in powdered poppy capsule extractive. Averagely linear-quantified fingerprint method provided accurate qualitative and quantitative similarities for chromatographic fingerprints of Chinese herbal medicines. The stability and operability of the averagely linear-quantified fingerprint method were verified by the parameter r. The average linear qualitative similarity SL (improved based on conventional qualitative "Similarity") was used as a qualitative criterion in the averagely linear-quantified fingerprint method, and the average linear quantitative similarity PL was introduced as a quantitative one. PL was able to identify the difference in the content of all the chemical components. In addition, PL was found to be highly correlated to the contents of two alkaloid compounds (morphine and codeine). A simple flow injection analysis was developed for the determination of antioxidant capacity in Chinese Herbal Medicines, which was based on the scavenging of 2,2-diphenyl-1-picrylhydrazyl radical by antioxidants. The fingerprint-efficacy relationship linking chromatographic fingerprints and antioxidant activities was investigated utilizing orthogonal projection to latent structures method, which provided important pharmacodynamic information for Chinese herbal medicines quality control. In summary, quantitative fingerprinting based on averagely linear-quantified fingerprint method can be applied for monitoring the quality consistency of Chinese herbal medicines, and the constructed orthogonal projection to latent structures model is particularly suitable for investigating the fingerprint-efficacy relationship.


Assuntos
Antioxidantes/análise , Medicamentos de Ervas Chinesas/química , Papaver/química , Cromatografia Líquida de Alta Pressão , Pós , Controle de Qualidade
19.
J Anesth Hist ; 3(2): 50-55, 2017 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-28641826

RESUMO

Evidence of human use of opium dates back as far as the sixth millennium BCE. Ancient societies through the Renaissance period created a variety of opium products, proliferating its common use and subsequent addiction. Because the active moiety was not known at this time, the potency of these opium concoctions could neither be predicted nor controlled. The first step in identifying opium's active ingredient, morphine, was its chemical isolation in the early 1800s by Wilhelm Sertürner. The subsequent elucidation of morphine's chemical formula and Sir Robert Robinson's derivation of morphine's structural formula, which won him the 1947 Nobel Prize in Chemistry, round out 150 years of the incremental advances in our chemical understanding of morphine. Nevertheless, our attempts to synthesize morphine, despite our advanced knowledge in synthetic chemistry, are still no match for the plant-based extraction of morphine from the poppy plant. The status quo remains problematic socially, economically, and politically; the relationships between the countries laboriously growing poppy plants to extract morphine and those countries importing these painkillers are unstable at best. In this study, we contrast the cumulative scientific discoveries that have led to our current chemical knowledge of morphine with the centuries-old natural method of morphine production that still dominates the opioid market today.


Assuntos
Analgésicos Opioides/história , Morfina/história , Papaver/química , Analgésicos Opioides/síntese química , Analgésicos Opioides/química , História do Século XV , História do Século XVI , História do Século XVII , História do Século XVIII , História do Século XIX , História do Século XX , História do Século XXI , História Antiga , História Medieval , Morfina/síntese química , Morfina/química , Extratos Vegetais/história , Resinas Vegetais/história
20.
Chem Biodivers ; 14(9)2017 Sep.
Artigo em Inglês | MEDLINE | ID: mdl-28599092

RESUMO

Poppy seeds (Papaver somniferum L.) belong to tasty food ingredients however, they should be considered also as valuable source of biologically active compounds. Content of selected metabolites, antioxidant and proteinase inhibitory activities were analyzed in vitro in extracts from seeds of fifteen poppy genotypes. Considerable variation in all parameters was detected within the set of analyzed poppy genotypes. The genotype Major expressed the highest antioxidant activity determined by all four methodological approaches (DPPH, ABTS, FRAP, RP). The genotype MS 423 exhibited the highest inhibitory activities against trypsin, thrombin and collagenase. Very specific position among all had the genotype Redy. Its grain extract reached significantly high levels in 9 out of 14 measured parameters (TPC, TFC, TTC, TAC, FRAP, RP, inhibitory activities against trypsin, thrombin, collagenase). Edible grains of poppy are valuable source of natural compounds which may be beneficial in pathological states associated with oxidative stress or increased proteinase activities.


Assuntos
Antioxidantes/química , Papaver/química , Extratos Vegetais/química , Inibidores de Proteases/química , Sementes/química , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Genótipo , Humanos , Papaver/genética , Fenóis/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Extratos Vegetais/genética , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Inibidores de Proteases/isolamento & purificação , Inibidores de Proteases/farmacologia , Sementes/genética
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