Chemical characterization of non-psychoactive Cannabis sativa L. extracts, in vitro antiproliferative activity and induction of apoptosis in chronic myelogenous leukaemia cancer cells.
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ABSTRACT:
SUBMITTER: Anceschi L
PROVIDER: S-EPMC9304126 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:Medical cannabis has been legally available for patients in a number of countries. Licensed producers produce a variety of cannabis strains with different concentrations of phytocannabinoids. Phytocannabinoids in medical cannabis are decarboxylated when subjected to heating for consumption by the patients or when extracted for preparing cannabis derivative products. There is little understanding of the true chemical composition of cannabis extracts, changes occurring during heating of the extracts, and their relevance to pharmacological effects. We investigated the extract from a popular commercial strain of medical cannabis, prior to and after decarboxylation, to understand the chemical profiles. A total of up to 62 compounds could be identified simultaneously in the extract derived from commercial cannabis, including up to 23 phytocannabinoids. Upon heating, several chemical changes take place, including the loss of carboxylic group from the acidic phytocannabinoids. This investigation attempts to reveal the chemical complexity of commercial medical cannabis extracts and the differences in the chemical composition of the native extract and the one subjected to heat. Comprehensive chemical analyses of medical cannabis extracts are needed for standardization, consistency, and, more importantly, an informed employment of this substance for therapeutic purposes.
| S-EPMC6044620 | biostudies-literature
Project description:Four crosses were made between inbred Cannabis sativa plants with pure cannabidiol (CBD) and pure Delta-9-tetrahydrocannabinol (THC) chemotypes. All the plants belonging to the F(1)'s were analyzed by gas chromatography for cannabinoid composition and constantly found to have a mixed CBD-THC chemotype. Ten individual F(1) plants were self-fertilized, and 10 inbred F(2) offspring were collected and analyzed. In all cases, a segregation of the three chemotypes (pure CBD, mixed CBD-THC, and pure THC) fitting a 1:2:1 proportion was observed. The CBD/THC ratio was found to be significantly progeny specific and transmitted from each F(1) to the F(2)'s derived from it. A model involving one locus, B, with two alleles, B(D) and B(T), is proposed, with the two alleles being codominant. The mixed chemotypes are interpreted as due to the genotype B(D)/B(T) at the B locus, while the pure-chemotype plants are due to homozygosity at the B locus (either B(D)/B(D) or B(T)/B(T)). It is suggested that such codominance is due to the codification by the two alleles for different isoforms of the same synthase, having different specificity for the conversion of the common precursor cannabigerol into CBD or THC, respectively. The F(2) segregating groups were used in a bulk segregant analysis of the pooled DNAs for screening RAPD primers; three chemotype-associated markers are described, one of which has been transformed in a sequence-characterized amplified region (SCAR) marker and shows tight linkage to the chemotype and codominance.
| S-EPMC1462421 | biostudies-other
Project description:Multiple therapeutic properties have been attributed to Cannabis sativa. However, further research is required to unveil the medicinal potential of Cannabis and the relationship between biological activity and chemical profile. The primary objective of this study was to characterize the chemical profile and antioxidant properties of three varieties of Cannabis sativa available in Uruguay during progressive stages of maturation. Fresh samples of female inflorescences from three stable Cannabis sativa phenotypes, collected at different time points during the end of the flowering period were analyzed. Chemical characterization of chloroform extracts was performed by 1H-NMR. The antioxidant properties of the cannabis sativa extracts, and pure cannabinoids, were measured in a Cu2+-induced LDL oxidation assay. The main cannabinoids in the youngest inflorescences were tetrahydrocannabinolic acid (THC-A, 242 ± 62 mg/g) and tetrahydrocannabinol (THC, 7.3 ± 6.5 mg/g). Cannabinoid levels increased more than twice in two of the mature samples. A third sample showed a lower and constant concentration of THC-A and THC (177 ± 25 and 1 ± 1, respectively). The THC-A/THC rich cannabis extracts increased the latency phase of LDL oxidation by a factor of 1.2-3.5 per μg, and slowed down the propagation phase of lipoperoxidation (IC50 1.7-4.6 μg/mL). Hemp, a cannabidiol (CBD, 198 mg/g) and cannabidiolic acid (CBD-A, 92 mg/g) rich variety, also prevented the formation of conjugated dienes during LDL oxidation. In fact, 1 μg of extract was able to stretch the latency phase 3.7 times and also to significantly reduce the steepness of the propagation phase (IC50 of 8 μg/mL). Synthetic THC lengthened the duration of the lag phase by a factor of 21 per μg, while for the propagation phase showed an IC50 ≤ 1 μg/mL. Conversely, THC-A was unable to improve any parameter. Meanwhile, the presence of 1 μg of pure CBD and CBD-A increased the initial latency phase 4.8 and 9.4 times, respectively, but did not have an effect on the propagation phase. Cannabis whole extracts acted on both phases of lipid oxidation in copper challenged LDL. Those effects were just partially related with the content of cannabinoids and partially recapitulated by isolated pure cannabinoids. Our results support the potentially beneficial effects of cannabis sativa whole extracts on the initial phase of atherosclerosis.
| S-EPMC7592720 | biostudies-literature
Project description:Cannabis is widely used as a therapeutic drug, especially by patients suffering from psychiatric and neurodegenerative diseases. However, the complex interplay between phytocannabinoids and their targets in the human receptome remains largely a mystery, and there have been few investigations into the relationship between the chemical composition of medical cannabis and the corresponding biological activity. In this study, we investigated 59 cannabis samples used by patients for medical reasons. The samples were subjected to extraction (microwave and supercritical carbon dioxide) and chemical analyses, and the resulting extracts were assayed in vitro using the CB1 and CB2 receptors. Using a partial least squares regression analysis, the chemical compositions of the extracts were then correlated to their corresponding cannabinoid receptor activities, thus generating predictive models that describe the receptor potency as a function of major phytocannabinoid content. Using the current dataset, meaningful models for CB1 and CB2 receptor agonism were obtained, and these reveal the insignificant relationships between the major phytocannabinoid content and receptor affinity for CB1 but good correlations between the two at CB2 receptors. These results also explain the anomalies between the receptor activities of pure phytocannabinoids and cannabis extracts. Furthermore, the models for CB1 and CB2 agonism in cannabis extracts predict the cannabinoid receptor activities of individual phytocannabinoids with reasonable accuracy. Here for the first time, we disclose a method to predict the relationship between the chemical composition, including phytocannabinoids, of cannabis extracts and cannabinoid receptor responses.
| S-EPMC7436063 | biostudies-literature
Project description:Cannabis sativa is a medicinal plant having a very complex matrix composed of mainly cannabinoids and terpenoids. The literature has numerous reports, which indicate that tetrahydrocannabinol (THC) is the only major psychoactive metabolite in C. sativa. It is important to explore other metabolites having the possibility of exhibiting the psychoactive character of various degrees and also to identify metabolites targeting other receptors such as opioid, ? amino butyric acid (GABA), glycine, serotonin, and nicotine present in C. sativa, the smoke of C. sativa, and other phytocannabinoid matrices. This article aims to achieve this goal by application of batteries of computational tools such as machine learning tools and multivariate methods on physiochemical and absorption, distribution, metabolism, excretion, and toxicity (ADMET) descriptors of 468 metabolites from C. sativa, its smoke and, other phytocannabinoids. The structure-activity relationship (SAR) showed that 54 metabolites from C. sativa have high scaffold homology with THC. Its implications on the route of administration and factors affecting the SAR are discussed. C. sativa smoke has metabolites that have possibility of interacting with GABA, and glycine receptors.
| S-EPMC6964292 | biostudies-literature
Project description:Hemp is considered one of the potential novel crops for human and animal nutrition. This study aimed to determine the complete chemical composition of 29 different varieties of whole hempseeds. Fatty acid composition, amino acid profile, mineral composition, and cannabinoids content were also evaluated. All hempseed varieties were milled to obtain whole hempseed flour. Differences between hempseed varieties were significant (p < 0.05) for all measured parameters. Proximate composition results showed that crude protein and fat contents varied from 21.6-28.9% and 21.1-35.7%, respectively. Fatty acid profiles revealed that the three major fatty acids were linoleic acid (52.79-57.13%) followed by α-linolenic acid (12.62-20.24%), and oleic acid (11.08-17.81%). All essential amino acids were detected in all varieties, with arginine (12.66-17.56 mg/100 g protein) present in abundance, whereas lysine was limiting. Substantial differences were found in the mineral content, and potassium (509.96-1182.65 mg/100 g) and iron (5.06-32.37 mg/100 mg) were the main macro- and microminerals found. All cannabinoids were found in small traces and tetrahydrocannabidiol (THC) was only detected in five varieties. To conclude, the nutritional composition of hempseeds with hull makes them suitable to be added into the diets of humans or animals as a highly beneficial novel ingredient.
| S-EPMC10814438 | biostudies-literature
Project description:Cannabis sativa is a herbaceous multiple-use species commonly employed to produce fiber, oil, and medicine. It is now becoming popular for the high nutritional properties of its seed oil and for the pharmacological activity of its cannabinoid fraction in inflorescences. The present study aims to apply nuclear magnetic resonance (NMR) spectroscopy to provide useful qualitative and quantitative information on the chemical composition of seed and flower Cannabis extracts obtained by ultra-sound-assisted extraction, and to evaluate NMR as an alternative to the official procedure for the quantification of cannabinoids. The estimation of the optimal ω-6/ω-3 ratio from the 1H NMR spectrum for the seed extracts of the Futura 75 variety and the quantitative results from the 1H and 13C NMR spectra for the inflorescence extracts of the Tiborszallasi and Kompolti varieties demonstrate that NMR technology represents a good alternative to classical chromatography, supplying sufficiently precise, sensitive, rapid, and informative data without any sample pre-treatment. In addition, different extraction procedures were tested and evaluated to compare the elaboration of spectral data with the principal component analysis (PCA) statistical method and the quantitative NMR results: the extracts obtained with higher polarity solvents (acetone or ethanol) were poor in psychotropic agents (THC < LOD) but had an appreciable percentage of both cannabinoids and triacylgliceroles (TAGs). These bioactive-rich extracts could be used in the food and pharmaceutical industries, opening new pathways for the production of functional foods and supplements.
| S-EPMC9182145 | biostudies-literature
Project description:COVID-19 is caused by the SARS-CoV-2 virus, which enters target cells via interactions with ACE2 and TMPRSS2. Here, we show AKT serine/threonine kinase-dependent epigenetic control of ACE2 and TMPRSS2 expression by high-cannabidiol (CBD) cannabis extracts and their individual components. CBD alone and extracts #1, #5, #7, and #129 downregulated ACE2 and TMPRSS2 in lung fibroblast WI-38 cells through AKT-mediated inhibition. miR-200c-3p and let-7a-5p were two contributing miRNAs in CBD-mediated suppression of ACE2 and TMPRSS2. CBD and terpene PTWT2.2 profoundly inhibited ACE2 and TMPRSS2 expression, both individually and in combination. Extracts #1, #5, #7, and #169 suppressed COX2 expression and remarkably attenuated TNFα/IFNγ-triggered induction of proinflammatory factors IL-6 and IL-8 by AKT pathway. The most abundant molecules present in extracts #1 and #7 modulated the expression of COX2, IL-6, and IL-8 both individually and in combination. These results reveal that high-CBD cannabis extracts attenuated ACE2 and TMPRSS2 expression and the induction of inflammatory mediators COX2, IL-6, and IL-8 via the AKT pathway, highlighting their potential anti-COVID-19 features.
| S-EPMC8913855 | biostudies-literature
Project description:Cannabis sativa L. is an herbaceous plant belonging to the family of Cannabaceae. It is classified into three different chemotypes based on the different cannabinoids profile. In particular, fiber-type cannabis (hemp) is rich in cannabidiol (CBD) content. In the present work, a rapid nano liquid chromatographic method (nano-LC) was proposed for the determination of the main cannabinoids in Cannabis sativa L. (hemp) inflorescences belonging to different varieties. The nano-LC experiments were carried out in a 100 µm internal diameter capillary column packed with a C18 stationary phase for 15 cm with a mobile phase composed of ACN/H2O/formic acid, 80/19/1% (v/v/v). The reverse-phase nano-LC method allowed the complete separation of four standard cannabinoids in less than 12 min under isocratic elution mode. The nano-LC method coupled to ultraviolet (UV) detection was validated and applied to the quantification of the target analytes in cannabis extracts. The nano-LC system was also coupled to an electrospray ionization-mass spectrometry (ESI-MS) detector to confirm the identity of the cannabinoids present in hemp samples. For the extraction of the cannabinoids, three different approaches, including dynamic maceration (DM), ultrasound-assisted extraction (UAE), and an extraction procedure adapted from the French Pharmacopeia's protocol on medicinal plants, were carried out, and the results achieved were compared.
| S-EPMC8036269 | biostudies-literature
Project description:Chemical composition of black cumin (Nigella sativa L.) seed extracts obtained by supercritical carbon dioxide at two different conditions that result in total extract (28 MPa/50°C, SFE 1) and major volatile part (12 MPa/40°C, SFE 2) and essential oil obtained by hydrodistillation of SFE-1 (HD SFE). SFE have been carried out to characterize the compounds and the variation of quinones and phenolics. The extracts were analysed by GC and GC-MS and the presence of phenolic compounds was further confirmed by 2D HSQCT (1)H and (13)C NMR spectroscopy. Forty-seven volatile compounds were detected where sixteen compounds were reported for the first time in the oil of this seed. Moreover, thymoquinone (TQ), dithymoquinone (DTQ), thymohydroquinone (THQ) and thymol (THY) were the major phenolic compounds. It can be concluded that the chemical composition of extracts obtained by SC CO2 extraction of the seeds showed better recovery of phenolic compounds than HD SFE and proved the occurrence of thermally labile or photosensitive bioactive volatiles of four major quinonic phenol compounds.
| S-EPMC3551137 | biostudies-literature