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1.
Food Chem ; 318: 126469, 2020 Jul 15.
Artigo em Inglês | MEDLINE | ID: mdl-32143130

RESUMO

In this study, the occurrence of cannabinoids in hemp-based food products was investigated. For that purpose, a new liquid chromatography tandem mass spectrometry method for the quantification of fifteen cannabinoids was developed and validated for multiple matrices. Method performances were good, fulfilling the SANTE/11813/2017 requirements, and allowing for products compliance testing with various national legislations on cannabinoids levels in food products. The limit of quantification of each analyte was 0.15 mg/kg for hemp seed and hemp protein, 0.6 mg/kg for hemp seed oil, and 0.005 mg/kg for raw milk and milk powder. The applicability of the method was further demonstrated by conducting a limited survey on twenty hemp-based food products. The survey revealed that products from the same category can have very different cannabinoids profiles and levels. These results highlighted the importance of cannabinoids testing of food products in view of the current heterogeneous and fast evolving regulatory landscape worldwide.


Assuntos
Canabinoides/análise , Cannabis/química , Cromatografia Líquida/métodos , Análise de Alimentos/métodos , Espectrometria de Massas em Tandem/métodos , Ração Animal , Animais , Leite/química , Sementes/química
2.
Food Chem ; 314: 126198, 2020 Jun 01.
Artigo em Inglês | MEDLINE | ID: mdl-31954285

RESUMO

The objective was to investigate the effects of heat pretreatment and simulated gastrointestinal digestion on potential antioxidant, anticancer and anti-inflammatory activities of hempseed (Cannabis sativa L.) proteins. Unheated isolated hempseed protein (IHP) and its heated counterparts (100 °C, 15 min and 30 min, termed as HP15D and HP30D) were hydrolyzed sequentially with pepsin and pancreatin and analyzed for digestibility and bioactivity (antioxidant, anti-proliferative and anti-inflammatory properties). Heat pretreatment led to an increase of low molecular weight proteins and degree of hydrolysis, and decrease of concentration of soluble protein, which means heat pretreated can significantly improve the digestibility of IHP. Pepsin-pancreatin digests released from heat pretreated IHP possessed less antioxidant, antiproliferative and anti-inflammatory properties than digests from unheated IHP. In conclusion, heat pre-treatment improved the digestibility of IHP but the resulting digests from heated IHP had lower bioactivity.


Assuntos
Antioxidantes , Cannabis/química , Pancreatina/metabolismo , Temperatura Alta , Humanos , Peso Molecular , Pepsina A/metabolismo , Proteínas de Plantas/metabolismo , Proteólise
3.
Forensic Sci Int ; 307: 110113, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31927249

RESUMO

Cannabis light preparations are products derived or containing dried female inflorescences of Cannabis sativa belonging to Chemotype III (THC/CBD ratio <<1); the total THC (THC+THCA) content in the crop must not exceed 0.2 % in accordance with the EU regulation. In Italy the most recent law for industrial hemp (242/2016) states that only for farmers this limit is extended to 0.6 %. On the other hand, the Ministry of the Interior published a note stating that the sale or the presence in the markets of products (inflorescences, concentrates, essences and resins) or plants with concentrations higher than 0.5 % constitutes a crime. In this confusing legislation framework, it is very important to assess the legality of hemp, determining the total amount of THC. To this end a reliable LC-UV analytical method was developed and validated taking into account parameters such as precision, accuracy, linearity, repeatability of peak area and retention time, limit of detection (LOD= 0.002 % for all cannabinoids) and limit of quantification (LOQ= 0.005 % for all cannabinoids). Accuracy was expressed as the relative error (Er%), while precision was measured as the coefficient of variation (CV%). A CV% below 3 % and Er% between ± 6 % were obtained. The linearity was proven in the concentration range 0.005-1 % for THC, THCA and CBN and 0.005 %-50 % for CBD and CBDA. The analytical method was applied to more than nine hundred cannabis light samples. Based on the law 242/2016, only 18 % of the crops are to be considered legal for the market (total THC<0.2 %). If the circular of the Ministry of the Interior should be converted as a proper law, a substantial amount of cannabis light preparations (24 %) would be considered illegal (total THC>0.5 %). On the other hand, the most of the inflorescences (58 %) have a total THC content comprised between 0.2 % and 0.5 %, and it is not clear whether these products could be sold or not. Moreover, Cannabis light products are not authorized for human consumption, even if everybody knows that this is their primary use. In conclusion, the cannabis light panorama in Italy is quite confused and more specific and clear legislation should be proposed.


Assuntos
Agricultura/legislação & jurisprudência , Canabinoides/análise , Cannabis/química , Cromatografia Líquida de Alta Pressão , Análise Espectral , Raios Ultravioleta , Humanos , Itália , Legislação de Medicamentos , Limite de Detecção
4.
Forensic Sci Int ; 306: 110064, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31786513

RESUMO

Hemp seeds and hempseed oil are marketed on- and off-line as health foods and cosmetics and have been reported to have high nutrient contents. However, because of the various side effects of cannabinoids, especially △9-tetrahydrocannabinol (THC), many countries regulate upper limits for THC in products, which creates the need for analytical techniques capable of measuring THC, cannabidiol (CBD), and cannabinol (CBN) levels in commercial hemp seeds and hempseed oil. In the present study, hemp seed and hempseed oil extracts obtained by methanol extraction, were analyzed by gas chromatography-mass spectrometry (GC/MS). Validation of the technique used was performed using calibration curves and by determining LODs, LOQs, specificities, selectivities, and intra- and inter-day precision and accuracies. In addition, matrix effects, process efficiencies, recoveries, and sample stabilities were investigated. In hemp seeds, as determined using the fully optimized method THC concentrations ranged from 0.06 to 5.91 µg/g, CBD concentrations from 0.32 to 25.55 µg/g, and CBN concentrations from 0.01 to 1.50 µg/g; CBN/THC ratios ranged from 0.1 to 1.60, and CBD/THC ratios from 0.11 to 62.56. Furthermore, the (THC + CBN)/CBD ratio of most hemp seed samples was less than one. In hempseed oil, THC concentrations ranged from 0.3 to 19.73 µg/mL, CBD concentrations from 6.66 to 63.40 µg/mL, CBN concentrations from 0.11 to 2.31 µg/mL, CBN/THC ratios from 0.12 to 0.42, and CBD/THC ratios from 3.21 to 22.50. Furthermore, (THC + CBN)/CBD ratios in all hempseed oil samples were less than one. The optimized methanol extraction-GC/MS technique was found to be satisfactory for determining THC, CBD, and CBN concentrations in hemp seeds and hempseed oil.


Assuntos
Canabinoides/análise , Cannabis/química , Comércio , Óleos Vegetais/química , Sementes/química , Toxicologia Forense/métodos , Cromatografia Gasosa-Espectrometria de Massas , Humanos , República da Coreia
5.
J Chromatogr A ; 1612: 460656, 2020 Feb 08.
Artigo em Inglês | MEDLINE | ID: mdl-31679712

RESUMO

Pesticide residue analysis in cannabis has become a subject of growing interest in North America since recent legalization in Canada and decriminalization for medicinal or recreational use in most US states. To meet regulatory and quality control standards, cannabis products should be tested for both authorized and unauthorized pesticides. In Canada, testing requirements mandated by Health Canada stipulate pesticide contaminant limits of quantification values of 0.02-3.0 µg/g, 0.01-2.5 µg/g and 0.01-1.5 µg/g for cannabis dried flowers, oil and fresh plants, respectively. Sample preparation and clean up methods reported in the literature for pesticide analysis in cannabis products include liquid-liquid extraction, solid-phase extraction, solid-phase microextraction and QuEChERS whereas separation and detection methods include thin-layer chromatography, capillary electrophoresis, high-performance liquid chromatography and gas chromatography in combination with various detectors such as UV and mass spectrometers. Advantages and disadvantages of the various analytical methods used in pesticide analysis of cannabis products are evaluated in this review. Furthermore, challenges ahead and future directions are discussed.


Assuntos
Cannabis/química , Resíduos de Praguicidas/análise , Praguicidas/química , Cromatografia Gasosa , Cromatografia Líquida de Alta Pressão , Cromatografia em Camada Delgada , Limite de Detecção , Extração Líquido-Líquido , Resíduos de Praguicidas/isolamento & purificação , Extração em Fase Sólida , Microextração em Fase Sólida , Espectrometria de Massas em Tandem
6.
Altern Ther Health Med ; 26(S1): 12-16, 2020 Feb.
Artigo em Inglês | MEDLINE | ID: mdl-31634872

RESUMO

The high frequency and painful profile of inflammatory oral lesions and the lack of an effective drug protocol for their management stimulate the search for pharmacological alternatives for the treatment of these conditions. Cannabidiol is the major non-psychotropic constituent of Cannabis sativa, receiving lately scientific interest because of its potential in the treatment of inflammatory disorders such as asthma, colitis and arthritis. There is little published in the current literature about the use of cannabidiol in oral health. Among its many protective functions, the ability to attenuate inflammation through the modulation of cytokines and its antiedema and analgesic effects may be important features in the treatment of oral lesions. In this review, we suggest that cannabidiol can be useful in the management of oral inflammatory disorders.


Assuntos
Anti-Inflamatórios não Esteroides/administração & dosagem , Canabidiol/uso terapêutico , Cannabis/química , Inflamação/tratamento farmacológico , Doenças da Boca/tratamento farmacológico , Citocinas , Humanos , Dor
7.
Anal Bioanal Chem ; 412(2): 413-423, 2020 Jan.
Artigo em Inglês | MEDLINE | ID: mdl-31760447

RESUMO

The chemical composition of Cannabis sativa L. has been extensively investigated for several years; nevertheless, a detailed lipidome characterization is completely lacking in the literature. To achieve this goal, an extraction and enrichment procedure was developed for the characterization of phospholipids and sulfolipids. Firstly, a study on the solid-liquid extraction was performed, to maximize the recovery of the considered lipids; the best procedure consisted of a simple extraction with a mixture of methanol and chloroform (1:1, v/v). The hemp extracts were analyzed by ultra-high-performance liquid chromatography coupled to high-resolution mass spectrometry and lipids were tentatively identified by Lipostar. To improve the number of identifications, an enrichment method, based on graphitized carbon black solid phase extraction, was evaluated to fractionate phospholipids and sulfolipids into separate eluates. Recovery and matrix effects of the procedure were determined on a mixture of standard lipids, containing representative compounds for each considered lipid class. The optimized method allowed the tentative identification of 189 lipids, including 51 phospholipids and 80 sulfolipids, in the first and second fractions, respectively. The detection of only 6 sulfolipids in the first fraction and 9 phospholipids in the second fraction proved the efficacy of the fractionation method, which also allowed the number of lipid identifications to be increased compared to the same procedure without enrichment, which scored 100 lipids. Finally, a semi-quantitative analysis permitted the hemp polar lipidome to be characterized. The results of this study allow knowledge of the hemp chemical composition to be improved with a detailed description of its phospho- and sulfolipid profiles. Graphical abstract.


Assuntos
Cannabis/química , Quimioinformática , Lipidômica , Espectrometria de Massas/métodos , Extração em Fase Sólida/métodos , Cromatografia Líquida de Alta Pressão/métodos , Lipídeos/análise , Fosfolipídeos/análise
8.
Talanta ; 208: 120384, 2020 Feb 01.
Artigo em Inglês | MEDLINE | ID: mdl-31816756

RESUMO

Elucidation of Cannabis composition is required to evaluate the potential of this plant for pharmacological uses, but also for implementation in breeding programs with agronomical purposes. The aim of the present study was to develop a method for untargeted analysis of polar and non-polar Cannabis extracts. For this purpose, extracts from 17 cultivars of Cannabis sativa L. were analyzed by gas chromatography-time-of-flight/mass spectrometry (GC-TOF/MS) and liquid chromatography quadrupole time-of-flight tandem mass spectrometry (LC-QTOF MS/MS) in high resolution mode. One hundred sixty-nine compounds were identified in the extracts by searching MS and MS/MS information. Among identified families, there were mainly cannabinoids, terpenoids, lipids and flavonoids, but also some interesting compounds such as amino and organic acids, among others. Relative contents of terpenoids and cannabinoids in the same cultivars grown in greenhouse and field were compared. Compositional differences in the profile of terpenoids and cannabinoids between both types of grown conditions were found.


Assuntos
Cannabis/química , Cromatografia Líquida/métodos , Cromatografia Gasosa-Espectrometria de Massas/métodos , Extratos Vegetais/análise , Canabinoides/análise , Cannabis/crescimento & desenvolvimento , Ambiente Controlado , Terpenos/análise
9.
Int J Mol Sci ; 20(22)2019 Nov 11.
Artigo em Inglês | MEDLINE | ID: mdl-31717952

RESUMO

Earlier this year we published a method article aimed at optimising protein extraction from mature buds of medicinal cannabis for trypsin-based shotgun proteomics (Vincent, D., et al. Molecules 2019, 24, 659). We then developed a top-down proteomics (TDP) method (Vincent, D., et al. Proteomes 2019, 7, 33). This follow-up study aims at optimising the digestion of medicinal cannabis proteins for identification purposes by bottom-up and middle-down proteomics (BUP and MDP). Four proteases, namely a mixture of trypsin/LysC, GluC, and chymotrypsin, which target different amino acids (AAs) and therefore are orthogonal and cleave proteins more or less frequently, were tested both on their own as well as sequentially or pooled, followed by nLC-MS/MS analyses of the peptide digests. Bovine serum albumin (BSA, 66 kDa) was used as a control of digestion efficiency. With this multiple protease strategy, BSA was reproducibly 97% sequenced, with peptides ranging from 0.7 to 6.4 kD containing 5 to 54 AA residues with 0 to 6 miscleavages. The proteome of mature apical buds from medicinal cannabis was explored more in depth with the identification of 27,123 peptides matching 494 unique accessions corresponding to 229 unique proteins from Cannabis sativa and close relatives, including 130 (57%) additional annotations when the list is compared to that of our previous BUP study (Vincent, D., et al. Molecules 2019, 24, 659). Almost half of the medicinal cannabis proteins were identified with 100% sequence coverage, with peptides composed of 7 to 91 AA residues with up to 9 miscleavages and ranging from 0.6 to 10 kDa, thus falling into the MDP domain. Many post-translational modifications (PTMs) were identified, such as oxidation, phosphorylations, and N-terminus acetylations. This method will pave the way for deeper proteome exploration of the reproductive organs of medicinal cannabis, and therefore for molecular phenotyping within breeding programs.


Assuntos
Cannabis/química , Maconha Medicinal/química , Proteínas de Plantas/química , Proteômica/métodos , Quimotripsina/metabolismo , Flores/química , Espectrometria de Massas/métodos , Proteólise
10.
J Food Sci ; 84(12): 3682-3690, 2019 Dec.
Artigo em Inglês | MEDLINE | ID: mdl-31691301

RESUMO

The purpose of this paper was to study the extraction conditions of hemp proteins from undelipidated press-cakes. The effects of different hydration conditions on protein recovery yield and polypeptide profile were evaluated: pH (2 to 12), ionic strength (0 to 500 mM NaCl) and press-cake/liquid weight ratio (2% to 22%). pH was the most impacting factor. At acidic pH (2 to 7) the extraction yields were low and quite constant (<7%), corresponding mainly to hemp albumins solubilization. The extraction of globulins started to increase significantly from pH 8, with protein extraction yield varying from 8.3% at pH 8 to 67.1% at pH 12 for a 10% press-cake/liquid weight ratio. The addition of NaCl in press-cake suspensions did not increase the total nitrogen content in aqueous extracts at alkaline pH while the lowest press-cake/liquid weight ratios (5% to 10%) were revealed optimal regarding protein recovery rate. The intense coloration observed on the aqueous extracts above pH 8 was assigned to solubilization and oxidation of phenolic compounds whose concentration increased about sevenfolds from pH 2 to 12. At the highest applied pH (11 to 12), the formation of covalent complexes between phenolic compounds and some hemp polypeptides was hypothesized. Aqueous extraction at strong alkaline pH (>9) without salt addition and respecting a 10% press-cake/liquid weight ratio should be retained to optimize protein extraction yield. However, further purification steps are required to evaluate the nutritional, organoleptic, and techno-functional properties of hemp proteins extracted in such conditions. PRACTICAL APPLICATION: The traditional extraction process of hemp proteins by alkaline solubilization and isoelectric precipitation, mostly from delipidated hemp press-cake, leads to limited quantity and poor solubility of extracted proteins, and data related to extraction conditions are insufficiently available to optimize this process. This article aims to find optimal hydration conditions (pH, ionic strength, press-cake to liquid ratio) for protein extraction from undelipidated hemp press-cake, allowing high protein recovery and preserving protein quality. The results obtained represent very useful data for developing an economically viable and sustainable extraction process of proteins from raw hemp press-cake.


Assuntos
Albuminas/isolamento & purificação , Cannabis/química , Fracionamento Químico/métodos , Proteínas de Plantas/isolamento & purificação , Albuminas/química , Concentração de Íons de Hidrogênio , Proteínas de Plantas/química , Solubilidade
11.
Gac Med Mex ; 155(5): 508-512, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31695229

RESUMO

Cannabis (marijuana) is one of the most consumed psychoactive substances in the world. The term marijuana is of Mexican origin. The primary cannabinoids that have been studied to date include cannabidiol and delta-9-tetrahydrocannabinol, which is responsible for most cannabis physical and psychotropic effects. Recently, the endocannabinoid system was discovered, which is made up of receptors, ligands and enzymes that are widely expressed in the brain and its periphery, where they act to maintain balance in several homeostatic processes. Exogenous cannabinoids or naturally-occurring phytocannabinoids interact with the endocannabinoid system. Marijuana must be processed in a laboratory to extract tetrahydrocannabinol and leave cannabidiol, which is the product that can be marketed. Some studies suggest cannabidiol has great potential for therapeutic use as an agent with antiepileptic, analgesic, anxiolytic, antipsychotic, anti-inflammatory and neuroprotective properties; however, the findings on cannabinoids efficacy and cannabis-based medications tolerability-safety for some conditions are inconsistent. More scientific evidence is required in order to generate recommendations on the use of medicinal cannabis.


Assuntos
Canabidiol/uso terapêutico , Endocanabinoides/metabolismo , Maconha Medicinal/uso terapêutico , Animais , Encéfalo/metabolismo , Canabidiol/isolamento & purificação , Canabidiol/metabolismo , Cannabis/química , Dronabinol/isolamento & purificação , Dronabinol/metabolismo , Dronabinol/farmacologia , Humanos , Ratos , Receptor CB1 de Canabinoide/metabolismo , Receptor CB2 de Canabinoide/metabolismo , Receptores de Canabinoides/metabolismo , Suínos , Canais de Cátion TRPV/metabolismo
12.
J Agric Food Chem ; 67(46): 12895-12903, 2019 Nov 20.
Artigo em Inglês | MEDLINE | ID: mdl-31682429

RESUMO

Genipin, a natural electrophilic cross-linker, was applied (5, 10, 20, and 30 mM) to modify hempseed protein isolate (HPI). Genipin treatments resulted in general losses of total sulfhydryls (up to 2.9 nmol/mg) and free amines (up to 77.3 nmol/mg). Surface hydrophobicity decreased by nearly 90% with 30 mM genipin, corresponding to similar tryptophan fluorescence quenching. The genipin treatment converted HPI into highly cross-linked polymers. Hydrogels formed with such polymers when also incorporated with hemp oil emulsions exhibited substantially enhanced gelling ability: up to 3.3- and 2.6-fold increases, respectively, in gel strength and gel elasticity over genipin-untreated protein. The genipin-modified composite gels also exhibited superior water-holding capacity. Microstructural analysis revealed a compact gel network filled with protein-coated oil globules that interacted intimately with the protein matrix when treated with genipin. Such gels remained readily digestible. Hence, genipin-treated hemp protein hydrogels show promise as functional food components.


Assuntos
Cannabis/química , Hidrogéis/química , Iridoides/química , Proteínas de Plantas/química , Reagentes para Ligações Cruzadas/química , Emulsões/química , Reologia , Sementes/química
13.
Int J Mol Sci ; 20(23)2019 Nov 25.
Artigo em Inglês | MEDLINE | ID: mdl-31775230

RESUMO

Cannabis sativa L. is a plant long used for its textile fibers, seed oil, and oleoresin with medicinal and psychoactive properties. It is the main source of phytocannabinoids, with over 100 compounds detected so far. In recent years, a lot of attention has been given to the main phytochemicals present in Cannabis sativa L., namely, cannabidiol (CBD) and Δ9-tetrahydrocannabinol (THC). Compared to THC, CBD has non-psychoactive effects, an advantage for clinical applications of anti-tumor benefits. The review is designed to provide an update regarding the multi-target effects of CBD in different types of cancer. The main focus is on the latest in vitro and in vivo studies that present data regarding the anti-proliferative, pro-apoptotic, cytotoxic, anti-invasive, anti-antiangiogenic, anti-inflammatory, and immunomodulatory properties of CBD together with their mechanisms of action. The latest clinical evidence of the anticancer effects of CBD is also outlined. Moreover, the main aspects of the pharmacological and toxicological profiles are given.


Assuntos
Antineoplásicos/uso terapêutico , Canabidiol/uso terapêutico , Cannabis/química , Neoplasias/tratamento farmacológico , Fitoterapia , Extratos Vegetais/uso terapêutico , Humanos , Prognóstico
14.
Integr Cancer Ther ; 18: 1534735419881498, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31595793

RESUMO

Background: Cancer-related cachexia and anorexia syndrome (CACS) is a common phenomenon in cancer patients. Cannabis has been suggested to stimulate appetite but research on this issue has yielded mixed results. The current study aimed to evaluate the effect of dosage-controlled cannabis capsules on CACS in advanced cancer patients. Methods: The cannabis capsules used in this study contained two fractions of oil-based compounds. The planned treatment was 2 × 10 mg per 24 hours for six months of tetrahydrocannabinol (THC) 9.5 mg and cannabidiol (CBD) 0.5 mg. If patients suffered from side effects, dosage was reduced to 5 mg × 2 per day (THC 4.75 mg, CBD 0.25 mg). Participants were weighed on every physician visit. The primary objective of the study was a weight gain of ≥10% from baseline. Results: Of 24 patients who signed the consent form, 17 started the cannabis capsules treatment, but only 11 received the capsules for more than two weeks. Three of six patients who completed the study period met the primary end-point. The remaining three patients had stable weights. In quality of life quaternaries, patients reported less appetite loss after the cannabis treatment (p=0.05). Tumor necrosis factor-α (TNF-α) levels decreased after the cannabis treatment but without statistical significance. According to patients' self-reports, improvement in appetite and mood as well as a reduction in pain and fatigue was demonstrated. Conclusions: Despite various limitations, this preliminary study demonstrated a weight increase of ≥10% in 3/17 (17.6%) patients with doses of 5mgx1 or 5mgx2 capsules daily, without significant side effects. The results justify a larger study with dosage-controlled cannabis capsules in CACS.


Assuntos
Anorexia/tratamento farmacológico , Caquexia/tratamento farmacológico , Canabidiol/uso terapêutico , Cannabis/química , Cápsulas/uso terapêutico , Dronabinol/uso terapêutico , Efeitos Colaterais e Reações Adversas Relacionados a Medicamentos/tratamento farmacológico , Idoso , Idoso de 80 Anos ou mais , Analgésicos/uso terapêutico , Anorexia/etiologia , Caquexia/etiologia , Feminino , Humanos , Masculino , Pessoa de Meia-Idade , Neoplasias/complicações , Projetos Piloto , Qualidade de Vida , Autorrelato
15.
Elife ; 82019 09 30.
Artigo em Inglês | MEDLINE | ID: mdl-31566564

RESUMO

Transient receptor potential vanilloid 2 (TRPV2) plays a critical role in neuronal development, cardiac function, immunity, and cancer. Cannabidiol (CBD), the non-psychotropic therapeutically active ingredient of Cannabis sativa, is an activator of TRPV2 and also modulates other transient receptor potential (TRP) channels. Here, we determined structures of the full-length rat TRPV2 channel in apo and CBD-bound states in nanodiscs by cryo-electron microscopy. We show that CBD interacts with TRPV2 through a hydrophobic pocket located between S5 and S6 helices of adjacent subunits, which differs from known ligand and lipid binding sites in other TRP channels. CBD-bound TRPV2 structures revealed that the S4-S5 linker plays a critical role in channel gating upon CBD binding. Additionally, nanodiscs permitted us to visualize two distinct TRPV2 apo states in a lipid environment. Together these results provide a foundation to further understand TRPV channel gating, their divergent physiological functions, and to accelerate structure-based drug design.


Assuntos
Canabidiol/farmacologia , Lipídeos/química , Canais de Cátion TRPV/genética , Animais , Sítios de Ligação/efeitos dos fármacos , Cannabis/química , Microscopia Crioeletrônica , Humanos , Interações Hidrofóbicas e Hidrofílicas/efeitos dos fármacos , Ligantes , Mutação/genética , Conformação Proteica em alfa-Hélice/efeitos dos fármacos , Estrutura Secundária de Proteína , Ratos , Canais de Cátion TRPV/ultraestrutura
16.
Molecules ; 24(19)2019 Oct 07.
Artigo em Inglês | MEDLINE | ID: mdl-31591294

RESUMO

In this work, the concentration of nine cannabinoids, six neutral cannabinoids (THC, CBD, CBC, CBG, CBN and CBDV) and three acidic cannabinoids (THCA CBGA and CBDA), was used to identify the Italian retailers of Cannabis sativa L. (hemp), reinforcing the idea that the practice of categorizing hemp samples only using THC and CBD is inadequate. A high-performance liquid chromatography/high-resolution mass spectrometry (HPLC-MS/MS) method was developed for screening and simultaneously analyzing the nine cannabinoids in 161 hemp samples sold by four retailers located in different Italian cities. The hemp samples dataset was analyzed by univariate and multivariate analysis with the aim to identify the hemp retailers without any other information on the hemp samples like Cannabis strains, seeds, soil and cultivation characteristics, geographical origin, product storage, etc. The univariate analysis highlighted that the hemp samples could not be differentiated by using any of the nine cannabinoids analyzed. To evaluate the real efficiency of the discrimination among the four hemp retailers a partial least squares discriminant analysis (PLS-DA) was applied. The PLS-DA results showed a very good discrimination between the four hemp retailers with an explained variance of 100% and low classification errors in both calibration (5%) and cross validation (6%). A total of 92% of the hemp samples were correctly classified by the cannabinoid variables in both fitting and cross validation. This work contributed to show that an analytical method coupled with multivariate analysis can be used as a powerful tool for forensic purposes.


Assuntos
Canabinoides/análise , Cannabis/química , Canabinoides/química , Cromatografia Líquida de Alta Pressão/métodos , Ciências Forenses/métodos , Itália , Análise dos Mínimos Quadrados , Análise Multivariada , Espectrometria de Massas em Tandem/métodos
17.
J Food Sci ; 84(11): 3147-3155, 2019 Nov.
Artigo em Inglês | MEDLINE | ID: mdl-31599978

RESUMO

Oxidative stability of hempseed and soybean oils, was evaluated after heating at 180 °C, followed by a subsequent 14-day storage at 38 °C. Natural plant extracts (Rosemary, Sage, and Thyme) were added to oils, to evaluate the carry-over stabilizing potential. Heated oils exhibited a relatively faster (P < 0.05) onset of lipid oxidation, as depicted by the analysis of the peroxides and aldehydes formed during the lipid oxidation process, with hempseed oil being more susceptible to lipid oxidation than soybean oil. There were notable losses in ω-3 PUFA and ω-6-GLA during storage of heat treated hempseed oil (P < 0.05). Moreover, peroxide values measured from hempseed oil remained low after high-temperature heating but progressed at a relatively greater rate than that observed in soybean during storage (P < 0.05). The addition of different plant extracts to oils did not prevent oxidation due to heating, but effectively inhibited the generation of hydroperoxides during subsequent storage (P < 0.05). This stabilizing effect was attributed to retention of tocopherols, in particular, γ-tocopherol. PRACTICAL APPLICATION: This research demonstrates the use of plant extracts like rosemary, sage and thyme, for improving the shelf-life and nutritional stability of hempseed and soybean oil. We demonstrate the deterioration of fatty acid profiles and vitamin E levels in the oil on heating and subsequent storage, and show the efficacy of using plant extracts in slowing down these deteriorations. This research will be applicable in food industries using or producing oils for use in food during cooking, and also as dressing on already processed food products.


Assuntos
Cannabis/química , Ácidos Graxos Ômega-3/análise , Manipulação de Alimentos/métodos , Extratos Vegetais/farmacologia , Óleo de Soja/química , Vitamina E/análise , Ácidos Graxos/análise , Armazenamento de Alimentos/métodos , Temperatura Alta , Peróxido de Hidrogênio/análise , Peroxidação de Lipídeos/efeitos dos fármacos , Óleos Vegetais/química , Rosmarinus/química , Salvia officinalis/química , Sementes/química , Thymus (Planta)/química
18.
Anal Chim Acta ; 1090: 47-56, 2019 Dec 20.
Artigo em Inglês | MEDLINE | ID: mdl-31655645

RESUMO

Soft independent modeling of class analogy (SIMCA) is an important method for authentication. The key parameters for SIMCA, the number of principal components and the decision threshold, determine the model's performance. In this report, a self-optimizing SIMCA that automatically determines these two parameters is devised and referred to as automatic SIMCA (aSIMCA). An efficient optimization is obtained by incorporating response surface modeling (RSM) and bootstrapped Latin partitions with the model-building dataset. A set of design points over the ranges of the two parameters are evaluated with respect to sensitivity and specificity by using the model-building data from target and non-target classes. Averages of the sensitivity and specificity are used as responses for the design points. A 2-dimensional interpolation and a bivariate cubic polynomial were used to model the response surface. As a control method, a grid search that evaluates all combinations of the two parameters over the same ranges was performed in parallel to determine the best conditions for SIMCA and the modeling performance was compared to aSIMCA with RSM. The developed aSIMCA methods were evaluated by authenticating two botanical extracts sets, i.e., marijuana and hemp, with spectral datasets collected from various spectroscopic techniques, including nuclear magnetic resonance, high-resolution mass, and ultraviolet spectrometry. Results of a paired t-test indicated that the aSIMCA with the RSM had similar performance with the one optimized by the grid search for modeling marijuana and hemp, while the RSM was more computationally efficient. The 2-dimensional interpolation is preferred because the better efficiency and the fit to the response surface is more precise.


Assuntos
Algoritmos , Cannabis/química , Modelos Teóricos , Espectroscopia de Ressonância Magnética/estatística & dados numéricos , Espectrometria de Massas/estatística & dados numéricos , Extratos Vegetais/análise , Espectrofotometria Ultravioleta/estatística & dados numéricos
19.
Anal Chim Acta ; 1088: 79-88, 2019 Dec 11.
Artigo em Inglês | MEDLINE | ID: mdl-31623719

RESUMO

In response to the Canadian federal government's Cannabis Tracking and Licensing System compliance standards, a quantitative method was created for cannabis analysis, and validated using Eurachem V.2 (2014) guidelines. Cannabinol, cannabidiol, cannabigerol, cannabichromene, cannabidiolic acid, cannabigerolic acid, Δ-9-tetrahydrocannabinol, and Δ-9-tetrahydrocannabinolic acid A were all analysed by scheduled multiple reaction monitoring (MRM) via LC-MS/MS and isotope dilution. In addition, aflatoxins B1, B2, G1, and G2 were also analysed by scheduled MRM via LC-MS/MS and matrix matched calibration curves in order to achieve the reporting limits (≤2 µg kg-1) set out by the European Pharmacopoeia. The LODs/LOQs were 0.50/1.7, 2.0/6.7, 0.59/2.0, and 0.53/1.8 µg kg-1, for B1, B2, G1, and G2 respectively. Thirty one terpenes were analysed by selected reaction monitoring via GC-MS/MS and isotope dilution using ß-myrcene-d6 as a surrogate. All quantitative analyses can be accomplished using less than 1 g of material, with minimal solvent and consumable use, on low resolution instruments in less than 30 min of instrument time. Of important note is this method's power of selectivity, working ranges, and lack of need for extraction consumables such as SPE or QuEChERS, thereby minimising analytical costs and time.


Assuntos
Aflatoxinas/análise , Canabinoides/análise , Cannabis/química , Contaminação de Medicamentos/prevenção & controle , Regulamentação Governamental , Fidelidade a Diretrizes , Terpenos/análise , Canadá , Cromatografia Líquida , Medição de Risco , Espectrometria de Massas em Tandem
20.
An Acad Bras Cienc ; 91(3): e20190676, 2019.
Artigo em Inglês | MEDLINE | ID: mdl-31618414

RESUMO

The aim of this work was to optimize a maceration condition of cannabis (Cannabis sativa L.). A circumscribed central composite experimental design was applied in this work. Temperature and time were varied from 40-80 °C and 30-90 min, respectively. The three responses (i.e., extraction yield, cannabidiol content, and Δ9- tetrahydrocannabinol content) were predicted by computer software. The yield was high when cannabis was macerated using ethanol at high temperature and long duration time. While cannabidiol and Δ9- tetrahydrocannabinol content was high when macerating at a low heating temperature and short duration time. The optimal condition provided the simultaneous high of cannabidiol and Δ9- tetrahydrocannabinol content was 40 °C for 30 min. The prediction was accurate due to low percent error. This optimal condition could be used as a guide for maceration of cannabis to obtain the extract containing a high content of cannabidiol and Δ9- tetrahydrocannabinol.


Assuntos
Canabidiol/análise , Cannabis/química , Dronabinol/isolamento & purificação , Extratos Vegetais/análise , Cromatografia Líquida de Alta Pressão , Dronabinol/análise , Métodos , Temperatura , Fatores de Tempo
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