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1.
Nat Commun ; 13(1): 3150, 2022 06 07.
Artigo em Inglês | MEDLINE | ID: mdl-35672295

RESUMO

The STORR gene fusion event is considered essential for the evolution of the promorphinan/morphinan subclass of benzylisoquinoline alkaloids (BIAs) in opium poppy as the resulting bi-modular protein performs the isomerization of (S)- to (R)-reticuline essential for their biosynthesis. Here, we show that of the 12 Papaver species analysed those containing the STORR gene fusion also contain promorphinans/morphinans with one important exception. P. californicum encodes a functionally conserved STORR but does not produce promorphinans/morphinans. We also show that the gene fusion event occurred only once, between 16.8-24.1 million years ago before the separation of P. californicum from other Clade 2 Papaver species. The most abundant BIA in P. californicum is (R)-glaucine, a member of the aporphine subclass of BIAs, raising the possibility that STORR, once evolved, contributes to the biosynthesis of more than just the promorphinan/morphinan subclass of BIAs in the Papaveraceae.


Assuntos
Alcaloides , Benzilisoquinolinas , Morfinanos , Papaver , Alcaloides/metabolismo , Benzilisoquinolinas/metabolismo , Fusão Gênica , Morfinanos/metabolismo , Papaver/genética , Papaver/metabolismo , Proteínas de Plantas/genética , Proteínas de Plantas/metabolismo
2.
J Agric Food Chem ; 70(24): 7594-7606, 2022 Jun 22.
Artigo em Inglês | MEDLINE | ID: mdl-35674269

RESUMO

Bakery products containing poppy seeds are increasingly being commercialized. These seeds may be contaminated with latex from the Papaver somniferum L. plant rich in opium alkaloids (OAs). Therefore, health authorities demand the development of analytical methods to control them. In this study, an efficient and simple method was developed and validated for the first time to analyze six OAs in bakery products by high-performance liquid chromatography-tandem mass spectrometry. For this purpose, a solid-liquid extraction was optimized, and then a magnetic material [magnetite surface-modified with Fe(III) terephthalate, denoted as Fe3O4@TPA-Fe] was used for a fast magnetic solid-phase extraction. The method has been validated with adequate recoveries (70-110%) and relative standard deviations (<20%) and without matrix effects. Nine bakery samples (five breadsticks and four sliced bread) were analyzed; breadsticks showed low amounts of OAs, but two sliced bread showed higher amounts of OAs than the new amount (1.5 mg/kg) set by the Commission Regulation (EU) 2021/2142.


Assuntos
Alcaloides Opiáceos , Papaver , Cromatografia Líquida de Alta Pressão/métodos , Compostos Férricos , Fenômenos Magnéticos , Ópio/análise , Papaver/química , Sementes/química , Extração em Fase Sólida , Espectrometria de Massas em Tandem/métodos
3.
Food Chem ; 390: 133188, 2022 Oct 01.
Artigo em Inglês | MEDLINE | ID: mdl-35567969

RESUMO

Opium poppy abused in food has aroused public concerns due to its serious side effects. Effective monitoring is essential to fight the abuse crisis. Herein, we synthesized an easily prepared, affordable, accessible highly aggregated gold nanoparticles (AGNPs) performing in lateral flow immunoassay (LFIA) for detection opium poppy in herbal teas. Simultaneously, a LFIA based ontime-resolved fluorescent microspheres (TRFMs) was developed as contrastive method. In this study, morphine (MOR), codeine (COD) and thebaine (THE) were as the specific recognition markers of opium poppy. Results demonstrated the quantitative limits of detection were 0.0049/0.0053/0.084, 0.034/0.037/0.37 ng mL-1 for AGNPs/TRFMs-LFIA, respectively. The recoveries were 95%-107.5%/91%-106.7% with coefficient of variation was 1.6%-6.6%/1.8%-7.2%, indicating excellent accuracy and precision. Parallel experiments among AGNPs/TRFMs-LFIA and LC-MS/MS analysis showed good correlation. Overall, AGNPs-LFIA executed quantitative analysis within 15 min on the basis of simple treatment while providing a rapid and sensitive analysis strategy for illegal drugs abused.


Assuntos
Nanopartículas Metálicas , Papaver , Chás de Ervas , Cromatografia Líquida , Ouro , Imunoensaio , Papaver/química , Espectrometria de Massas em Tandem
4.
Drug Test Anal ; 14(8): 1539-1546, 2022 Aug.
Artigo em Inglês | MEDLINE | ID: mdl-35478494

RESUMO

Laboratories are challenged to distinguish whether a positive urine morphine result is due to heroin use or possible poppy seed consumption. Thebaine is an opium alkaloid that has been shown to be present in the urine of individuals who have consumed poppy seeds, as well as those who have used opium. It is not present in heroin. We present a sensitive, specific liquid chromatography tandem mass spectrometry (LC-MS/MS) assay for thebaine. We show that thebaine is detectable after consumption of two different poppy seed-containing products for up to 72 h in urine. We discuss limitations of the assay and suggest how the test might best be used.


Assuntos
Papaver , Tebaína , Cromatografia Líquida , Cromatografia Gasosa-Espectrometria de Massas/métodos , Heroína/análise , Humanos , Morfina/urina , Ópio/análise , Papaver/química , Sementes/química , Espectrometria de Massas em Tandem/métodos
5.
J Plant Physiol ; 271: 153641, 2022 Apr.
Artigo em Inglês | MEDLINE | ID: mdl-35240512

RESUMO

Opium poppy is the only commercial source of the narcotic analgesics morphine and codeine, and semi-synthetic derivatives of the natural opiate precursor thebaine, including oxycodone and the opioid antagonist naloxone. The plant also accumulates the vasodilator and antitussive agents papaverine and noscapine, respectively, which together with morphine, codeine and thebaine comprise the major benzylisoquinoline alkaloids (BIAs) in opium poppy. A majority of enzymes involved in the highly branched BIA metabolism in opium poppy have now been discovered, with many specifically localized to sieve elements of the phloem based on immunofluorescence labeling techniques. Transcripts corresponding to sieve element-localized biosynthetic enzymes were detected in companion cells, as expected. The more recent application of shotgun proteomics has shown that several enzymes operating late in the morphine and noscapine biosynthetic pathways occur primarily in laticifers that are adjacent or proximal to sieve elements. BIA biosynthesis and accumulation in opium poppy involves three phloem cell types and implicates the translocation of key pathway intermediates between sieve elements and laticifers. The recent isolation of uptake transporters associated with laticifers supports an apoplastic rather than a symplastic route for translocation. In spite of the extensive elucidation of BIA biosynthetic enzymes in opium poppy, additional transporters and other auxiliary proteins are clearly necessary to support the complex spatial organization and dynamics involved in product formation and sequestration. In this review, we provide an update of BIA metabolism in opium poppy with a focus on the role of phloem in the biosynthesis of the major alkaloids.


Assuntos
Alcaloides , Benzilisoquinolinas , Papaver , Alcaloides/metabolismo , Benzilisoquinolinas/metabolismo , Vias Biossintéticas , Papaver/metabolismo , Floema/metabolismo
6.
Curr Biol ; 32(9): 1909-1923.e5, 2022 05 09.
Artigo em Inglês | MEDLINE | ID: mdl-35316654

RESUMO

Glycosylphosphatidylinositol-anchored proteins (GPI-APs) are tethered to the outer leaflet of the plasma membrane where they function as key regulators of a plethora of biological processes in eukaryotes. Self-incompatibility (SI) plays a pivotal role regulating fertilization in higher plants through recognition and rejection of "self" pollen. Here, we used Arabidopsis thaliana lines that were engineered to be self-incompatible by expression of Papaver rhoeas SI determinants for an SI suppressor screen. We identify HLD1/AtPGAP1, an ortholog of the human GPI-inositol deacylase PGAP1, as a critical component required for the SI response. Besides a delay in flowering time, no developmental defects were observed in HLD1/AtPGAP1 knockout plants, but SI was completely abolished. We demonstrate that HLD1/AtPGAP1 functions as a GPI-inositol deacylase and that this GPI-remodeling activity is essential for SI. Using GFP-SKU5 as a representative GPI-AP, we show that the HLD1/AtPGAP1 mutation does not affect GPI-AP production and targeting but affects their cleavage and release from membranes in vivo. Our data not only implicate GPI-APs in SI, providing new directions to investigate SI mechanisms, but also identify a key functional role for GPI-AP remodeling by inositol deacylation in planta.


Assuntos
Arabidopsis , Papaver , Arabidopsis/metabolismo , Glicosilfosfatidilinositóis/genética , Glicosilfosfatidilinositóis/metabolismo , Humanos , Inositol/metabolismo , Papaver/genética , Papaver/metabolismo , Pólen/metabolismo
7.
Molecules ; 27(3)2022 Jan 27.
Artigo em Inglês | MEDLINE | ID: mdl-35164114

RESUMO

The objective of this study is to valorize Papaver rhoeas L. from the Taounate region of Morocco by determining the total polyphenol content (TPC), the total flavonoid content (TFC) and the antioxidant and antimicrobial activities of four organs. The quantification of TPC and TFC in root, stem, leaf and flower extracts (RE, SE, LE and FE, respectively) was estimated by the Folin-Ciocalteu reaction and the aluminum trichloride method, respectively. Two tests were used to assess antioxidant power: the DPPH test and TAC assay. The antimicrobial activity was studied against five pathogenic bacteria and yeast, using two methods: disk diffusion and microdilution. The TPC in LE and LF was twice as high as that in RE and SE (24.24 and 22.10 mg GAE/g, respectively). The TFC values in the four extracts were very close and varied between 4.50 mg QE/g in the FE and 4.38 mg QE/g in the RE. The LE and FE showed low DPPH values with IC50 = 0.50 and 0.52 mg/mL, respectively. The TAC measurement revealed the presence of a significant amount of antioxidants in the studied extracts, mainly in LE and FE (6.60 and 5.53 mg AAE/g, respectively). The antimicrobial activity results revealed significant activity on almost all of the tested strains. The MIC of FE and SE against E. coli 57 was 1.56 and 0.78 mg/mL, respectively, while against the S. aureus it was 50 and 25 mg/mL, respectively. The low MLC value (1.56 mg/mL) was recorded against E. coli 57 by RE and SE.


Assuntos
Anti-Infecciosos , Antioxidantes , Bactérias/crescimento & desenvolvimento , Papaver/química , Extratos Vegetais , Folhas de Planta/química , Polifenóis , Anti-Infecciosos/química , Anti-Infecciosos/isolamento & purificação , Anti-Infecciosos/farmacologia , Antioxidantes/química , Antioxidantes/isolamento & purificação , Antioxidantes/farmacologia , Marrocos , Papaver/crescimento & desenvolvimento , Extratos Vegetais/química , Extratos Vegetais/isolamento & purificação , Extratos Vegetais/farmacologia , Polifenóis/química , Polifenóis/isolamento & purificação , Polifenóis/farmacologia
8.
Sci Rep ; 12(1): 111, 2022 01 07.
Artigo em Inglês | MEDLINE | ID: mdl-34997061

RESUMO

Opium poppy (Papaver somniferum) is one of the world's oldest medicinal plants and a versatile model system to study secondary metabolism. However, our knowledge of its genetic diversity is limited, restricting utilization of the available germplasm for research and crop improvement. We used genotyping-by-sequencing to investigate the extent of genetic diversity and population structure in a collection of poppy germplasm consisting of 91 accessions originating in 30 countries of Europe, North Africa, America, and Asia. We identified five genetically distinct subpopulations using discriminate analysis of principal components and STRUCTURE analysis. Most accessions obtained from the same country were grouped together within subpopulations, likely a consequence of the restriction on movement of poppy germplasm. Alkaloid profiles of accessions were highly diverse, with morphine being dominant. Phylogenetic analysis identified genetic groups that were largely consistent with the subpopulations detected and that could be differentiated broadly based on traits such as number of branches and seed weight. These accessions and the associated genotypic data are valuable resources for further genetic diversity analysis, which could include definition of poppy core sets to facilitate genebank management and use of the diversity for genetic improvement of this valuable crop.


Assuntos
DNA de Plantas/genética , Genes de Plantas , Variação Genética , Genoma de Planta , Técnicas de Genotipagem , Papaver/genética , Polimorfismo de Nucleotídeo Único , Sementes/genética , Análise de Sequência de DNA , Alcaloides/metabolismo , Genótipo , Papaver/crescimento & desenvolvimento , Papaver/metabolismo , Fenótipo , Filogenia , Sementes/crescimento & desenvolvimento , Sementes/metabolismo
10.
J AOAC Int ; 105(2): 593-602, 2022 Mar 15.
Artigo em Inglês | MEDLINE | ID: mdl-34570218

RESUMO

BACKGROUND: Thebaine, as a main opiate alkaloid extracted from Papaveraceae plants, is widely used in the synthesis of many pharmaceutical ingredients such as buprenorphine, naltrexone, naloxone, and hydrocodone. Nevertheless, thebaine and related derivatives are often insoluble in aqueous media and have low bioavailability in digestive systems. OBJECTIVE: Reducing particle size and changing the morphology can mitigate the mentioned problem. In this study, extraction of thebaine from the capsule, stem, and root of Papaver bracteatum L. was optimized and micronization of extract components was developed to study solubility. METHODS: The extraction process was performed using supercritical carbon dioxide. Experimental central composite design was employed to determine the optimal conditions. Analysis of extract was done using a validated high performance liquid chromatography method and mass spectrometry. The micronization process was performed using an inhouse developed supercritical technique. The nanoparticles were characterized using field emission scanning electron microscopy (FESEM) and ImageJ software. The effect of micronization was explored on the solubility of extract components via ultraviolet spectroscopy. RESULTS: The percentage of thebaine in dried capsule, stem, and root powder was about 1.05, 0.31, and 0.83% respectively. The extraction results indicate that supercritical pressure has the greatest effect on the extraction yield. Analysis of FESEM images revealed that nanoparticles of extract components with particle size distribution of 5-100 nm were collected successfully. CONCLUSION: The extraction results indicate that pressure has the greatest effect on the extraction yield. In vitro studies illustrated that the solubility of extract components increased up to 1.7 times during the micronization process. HIGHLIGHTS: Expansion of supercritical methods as an effective method was performed for extracting and preparing alkaloid nanoparticles. This process led to improved oral bioavailability of alkaloids.


Assuntos
Papaver , Plantas Medicinais , Cromatografia Líquida de Alta Pressão , Tecnologia , Tebaína/análise , Tebaína/farmacologia
11.
J Forensic Sci ; 67(2): 712-719, 2022 Mar.
Artigo em Inglês | MEDLINE | ID: mdl-34724600

RESUMO

In forensic cases suspected to involve Papaver somniferum, species identification is key to the investigation. To accurately detect and identify P. somniferum as well as common adulterants of the same genus, 19 internal transcribed spacer 2 (ITS2) sequences of P. somniferum (256 bp), Papaver canescens (254 bp), Papaver nudicaule (254 bp), Papaver pavoninum (250 bp), Papaver radicatum (254 bp), and Papaver rhoeas (256 bp) were obtained. Based on the ITS2 sequence, similarity analysis via BLAST, the nearest Kimura-2-parameter (K2P) genetic distances were calculated, and a phylogenetic tree was constructed using MEGA X software for the identification of six species of Papaver. Finally, differences in the ITS2 secondary structure between species were analyzed. The best matches of the P. somniferum ITS2 sequence were of other P. somniferum from different sources. The nearest K2P genetic distances between P. somniferum and its counterparts from other sources were zero, which was the smallest pairwise genetic distance among distances from the other five Papaver species. Various sources of P. somniferum clustered into an independent branch in the phylogenetic tree. The secondary structures of P. somniferum and P. rhoeas were significantly different from those of the other four species of Papaver. In summary, P. somniferum can be effectively distinguished from five closely related plants of the same genus by using ITS2 as a DNA barcode.


Assuntos
Papaver , Código de Barras de DNA Taxonômico , DNA de Plantas/genética , DNA Espaçador Ribossômico/genética , Papaver/genética , Filogenia
12.
Chembiochem ; 23(10): e202100623, 2022 May 18.
Artigo em Inglês | MEDLINE | ID: mdl-34971022

RESUMO

Plant-derived natural compounds have been used for treating diseases since prehistorical times. The supply of many plant-derived natural compounds for medicinal purposes, such as thebaine, morphine, and codeine, is primarily dependent on opium poppy crop harvesting. This dependency adds an extra risk factor to ensuring the supply chain because crops are highly susceptible to environmental conditions. Emerging technologies, such as biocatalysis, might help to solve this problem by diversifying the sources of supply of these compounds. Here we review the first committed step in the production of alkaloid painkillers, the production of S-norcoclaurine, and the enzymes involved. The improvement of these enzymes can be carried out experimentally by directed evolution and rational design strategies, supported by computational methods, to create variants that produce the S-norcoclaurine precursor for alkaloid painkillers in heterologous organisms, meeting the pharmaceutical industry standards and needs without depending on opium poppy crops.


Assuntos
Alcaloides , Papaver
13.
J Nat Prod ; 85(1): 215-224, 2022 01 28.
Artigo em Inglês | MEDLINE | ID: mdl-34910498

RESUMO

During a research program to identify new cholinesterase inhibitors of natural origin, two new 7,8-didehydroprotoberberine alkaloids (1 and 2) and nine known compounds (3-11) were isolated from the capsules of the common ornamental poppy, Papaver setiferum (previously P. pseudo-orientale). Despite their reported instability, the 7,8-didehydroprotoberberines isolated herein appeared relatively stable, particularly as their trifluoroacetic acid salts. The spatial distributions of the isolated alkaloids were also analyzed using desorption electrospray ionization imaging mass spectrometry. The alkaloids were localized predominantly within the walls and vascular bundles of the capsules, with the highest relative abundances occurring in the lower half of the capsules toward the peduncle. The relative abundances of the alkaloids were also compared across plant development stages. Although most alkaloids did not show clear patterns in their concentration across development stages, the concentration of suspected oxidation products clearly spiked upon plant death. Finally, all isolated natural products were screened for inhibitory activities against a panel of cholinesterases, from both human and animal sources. These studies identified several competitive inhibitors of cholinesterases with potency in the low micromolar range (1-4, 6, 7), offering new lead compounds for the development of cholinesterase inhibitory drugs.


Assuntos
Alcaloides de Berberina/farmacologia , Inibidores da Colinesterase/farmacologia , Papaver/química , Animais , Alcaloides de Berberina/química , Humanos , Espectrometria de Massas por Ionização por Electrospray
14.
Addict Sci Clin Pract ; 16(1): 71, 2021 12 03.
Artigo em Inglês | MEDLINE | ID: mdl-34861895

RESUMO

BACKGROUND: Poppy seeds contain morphine and other opioid alkaloids and are commercially available in the United States. Users of poppy seed tea (PST) can consume several hundred morphine milligram equivalents per day, and opioid dependence from PST use can develop. We report a case of a patient with chronic pain and PST use leading to opioid use disorder (OUD). This case represents the first published report of OUD from PST successfully treated with buprenorphine (BUP) in a primary care setting. The provider in this case used a unique model of care with an opioid prescribing support team to deliver safe and effective care. CASE PRESENTATION: A 47-year-old man with chronic pain and prescription opioid use presented to primary care to discuss a flare of shoulder pain, and revealed in subsequent conversation a long-standing use of PST to supplement pain control. Attempts at cessation resulted in severe withdrawal symptoms, leading to return to PST use. The primary care provider consulted the VA Puget Sound SUpporting Primary care Providers in Opioid Risk reduction and Treatment (SUPPORT) team to evaluate the patient for OUD. The patient discontinued all opioids, and initiated BUP under the supervision of the primary care provider. He remained on a stable dosage, without relapse, 24 months later. CONCLUSIONS: PST, which can be made through purchase of readily available poppy pods, carries risk for development of OUD and overdose. Herein we highlight the utility of a primary care opioid prescribing support team in empowering a primary care provider to prescribe BUP to treat a patient with complex OUD.


Assuntos
Buprenorfina , Transtornos Relacionados ao Uso de Opioides , Papaver , Analgésicos Opioides/uso terapêutico , Buprenorfina/uso terapêutico , Humanos , Masculino , Pessoa de Meia-Idade , Transtornos Relacionados ao Uso de Opioides/tratamento farmacológico , Padrões de Prática Médica , Atenção Primária à Saúde , Chá , Estados Unidos
15.
Int J Mol Sci ; 22(22)2021 Nov 17.
Artigo em Inglês | MEDLINE | ID: mdl-34830309

RESUMO

Latex, a sticky emulsion produced by specialized cells called laticifers, is a crucial part of a plant's defense system against herbivory and pathogens. It consists of a broad spectrum of active compounds, which are beneficial not only for plants, but for human health as well, enough to mention the use of morphine or codeine from poppy latex. Here, we reviewed latex's general role in plant physiology and the significance of particular compounds (alkaloids and proteins) to its defense system with the example of Chelidonium majus L. from the poppy family. We further attempt to present latex chemicals used so far in medicine and then focus on functional studies of proteins and other compounds with potential pharmacological activities using modern techniques such as CRISPR/Cas9 gene editing. Despite the centuries-old tradition of using latex-bearing plants in therapies, there are still a lot of promising molecules waiting to be explored.


Assuntos
Anti-Infecciosos/química , Antineoplásicos/química , Chelidonium/metabolismo , Fatores Imunológicos/química , Látex/química , Alcaloides Opiáceos/química , Papaver/metabolismo , Compostos Fitoquímicos/química , Proteínas de Plantas/química , Sistemas CRISPR-Cas , Linhagem Celular Tumoral , Chelidonium/genética , Descoberta de Drogas/métodos , Edição de Genes/métodos , Herbivoria/efeitos dos fármacos , Humanos , Papaver/genética , Plantas Geneticamente Modificadas
17.
Forensic Sci Int ; 329: 111052, 2021 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-34688186

RESUMO

With tightening enforcement and restrictions amid the opioid epidemic, poppy seed tea is consumed as an alternative to mitigate the withdrawal symptoms or as a home remedy to relieve pain and stress. Previously published studies suggested the potential danger of consuming tea brewed with a moderate to a large amount of poppy seed. In this study, the effects of small quantity and repeat brewing on opiate concentrations were evaluated. A dispersive-micro solid phase extraction facilitated by magnetic carbon nanotubes (Mag-CNTs/d-µSPE) was developed, optimized, successfully validated, and applied to ten poppy seed tea samples using gas chromatography-mass spectrometry (GC-MS) analysis. A total of ten poppy seed samples were evaluated in this work. Two grams of bulk poppy seeds were brewed with 6 mL of heated and acidified DI water three times. The brewed tea samples were subjected to the validated Mag-CNTs/d-µSPE/GC-MS analysis. The total mean opiate concentrations obtained from three brews were 1.1-1926, 20.2-311, and 9.0-100 mg/kg for morphine, codeine, and thebaine, respectively. The total opiate yields obtained from the small quantity brewing, i.e., 6 g seed in 18 mL tea, in this study may provide minimal analgesic and euphoric effects. Over 80% of the total opiate yield was extracted in the first brew with acidified deionized water from the 10 min brewing period, and opiate yields from the second and third brew were minimal. However, potential overdose could occur for some tea samples when scaled up to the starter quantity of seed suggested for new users.


Assuntos
Nanotubos de Carbono , Papaver , Analgésicos Opioides , Codeína/análise , Cromatografia Gasosa-Espectrometria de Massas , Fenômenos Magnéticos , Morfina/análise , Extração em Fase Sólida , Chá , Tebaína , Água
18.
Nat Commun ; 12(1): 6030, 2021 10 15.
Artigo em Inglês | MEDLINE | ID: mdl-34654815

RESUMO

For millions of years, plants evolve plenty of structurally diverse secondary metabolites (SM) to support their sessile lifestyles through continuous biochemical pathway innovation. While new genes commonly drive the evolution of plant SM pathway, how a full biosynthetic pathway evolves remains poorly understood. The evolution of pathway involves recruiting new genes along the reaction cascade forwardly, backwardly, or in a patchwork manner. With three chromosome-scale Papaver genome assemblies, we here reveal whole-genome duplications (WGDs) apparently accelerate chromosomal rearrangements with a nonrandom distribution towards SM optimization. A burst of structural variants involving fusions, translocations and duplications within 7.7 million years have assembled nine genes into the benzylisoquinoline alkaloids gene cluster, following a punctuated patchwork model. Biosynthetic gene copies and their total expression matter to morphinan production. Our results demonstrate how new genes have been recruited from a WGD-induced repertoire of unregulated enzymes with promiscuous reactivities to innovate efficient metabolic pathways with spatiotemporal constraint.


Assuntos
Vias Biossintéticas , Cromossomos/metabolismo , Morfinanos/metabolismo , Noscapina/metabolismo , Papaver/genética , Papaver/metabolismo , Alcaloides/química , Alcaloides/metabolismo , Benzilisoquinolinas/metabolismo , Vias Biossintéticas/genética , Evolução Molecular , Genoma , Genômica , Família Multigênica , Proteínas de Plantas/genética
19.
BMC Res Notes ; 14(1): 348, 2021 Sep 08.
Artigo em Inglês | MEDLINE | ID: mdl-34496958

RESUMO

OBJECTIVE: Papaver decaisnei Hochst. & Steud. Ex Elkan and Papaver glaucum Boiss. & Hausskn. growing wild in Northern Iraq have been historically used for medicinal purposes. In this study, both species were evaluated for their alkaloid content and antimicrobial activities. RESULTS: Alkaloids were extracted and isolated by preparative thin-layer chromatography (TLC). Identification was carried out by comparing spectral data (UV and 1H-NMR) and TLC Rf values with those of authentic samples. Two alkaloids, proapaorphine-type mecambrine and aporphine-type roemerine were isolated from P. decaisnei. Two benzylisoquinoline type alkaloids papaverine (major alkaloid) and palaudine as well as aporphine-type N-methylasimilobine have been obtained in P. glaucum. Both P. glaucum and P. decaisnei extracts revealed strong antimicrobial activity on Pseudomonas aeruginosa ATCC 27853 and Enterococcus faecalis ATCC 29212. Collectively these results indicate that P. glaucum and P. decaisnei are promising sources of alkaloids that could further be investigated for medicinal purposes.


Assuntos
Alcaloides , Anti-Infecciosos , Papaver , Alcaloides/farmacologia , Anti-Infecciosos/farmacologia , Cromatografia em Camada Delgada , Extratos Vegetais/farmacologia
20.
Zhongguo Zhong Yao Za Zhi ; 46(16): 4111-4116, 2021 Aug.
Artigo em Chinês | MEDLINE | ID: mdl-34467721

RESUMO

Sanguinarine is the main active component of the Papaver plants, and protopine-6-hydroxylase(P6 H), involved in the sanguinarine biosynthetic pathway, can oxidize protopine to 6-hydroxyprotopine. The investigation on the diversity of P6 H genes in the medicinal Papaver plants contributes to the acquirement of P6 H with high activity to increase the biosynthesis of sanguinarine. Five P6 H genes in P. somniferum, P. orientale, and P. rhoeas were discovered based on the re-sequencing data of the Papaver species, followed by bioinformatics analysis. With the elongation factor 1α(EF-1α), which exhibits stable expression in the root and stem, as the internal reference gene, the transcription levels of P6H genes in roots and stems of the Papaver plants were detected by real-time fluorescent quantitative PCR. As indicated by the re-sequencing results, there were two genotypes of P6H in P. somniferum and P. orientale, respectively, and only one in P. rhoeas. The bioinformatics analysis showed that the P6 H proteins of the three Papaver plants contained the conserved domain cl12078, which is the characteristic of p450 supergene family, and transmembrane regions. The existence of signal peptide remained verification. Real-time fluorescent quantitative PCR results revealed that the transcription level of P6 H in roots of P. somniferum was about 1.44 times of that in stems(α=0.05). The present study confirmed genetic diversity of P6 H in the three medicinal Papaver plants, which lays a basis for the research on the biosynthesis pathway and mechanism of sanguinarine in Papaver species.


Assuntos
Alcaloides de Berberina , Papaver , Benzofenantridinas , Sistema Enzimático do Citocromo P-450/genética , Variação Genética , Papaver/genética
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