RESUMO
The phenolic composition, as well as the antioxidant and antimicrobial activities of two poorly investigated Achillea species, Achillea lingulata Waldst. and the endemic Achillea abrotanoides Vis., were studied. To obtain a more detailed phytochemical profile, four solvents with different polarities were used for the preparation of the plant extracts whose phenolic composition was analyzed using UHPLC-MS/MS (ultra-high performance liquid chromatography-tandem mass spectrometry). The results indicate that both of the investigated Achillea species are very rich in both phenolic acids and flavonoids, but that their profiles differ significantly. Chloroform extracts from both species had the highest yields and were the most chemically versatile. The majority of the examined extracts showed antimicrobial activity, while ethanolic extracts from both species were potent against all tested microorganisms. Furthermore, the antioxidant activity of the extracts was evaluated. It was found that the ethanolic extracts possessed the strongest antioxidant activities, although these extracts did not contain the highest amounts of detected phenolic compounds. In addition, several representatives of phenolic compounds were also assayed for these biological activities. Results suggest that ethanol is a sufficient solvent for the isolation of biologically active compounds from both Achillea species. Moreover, it was shown that the flavonoids naringenin and morin are mainly responsible for these antimicrobial activities, while caffeic, salicylic, chlorogenic, p-coumaric, p-hydroxybenzoic, and rosmarinic acid are responsible for the antioxidant activities of the Achillea extracts.
Assuntos
Achillea/química , Anti-Infecciosos/isolamento & purificação , Antioxidantes/isolamento & purificação , Hidroxibenzoatos/isolamento & purificação , Compostos Fitoquímicos/isolamento & purificação , Achillea/classificação , Anti-Infecciosos/química , Anti-Infecciosos/farmacologia , Antioxidantes/química , Antioxidantes/farmacologia , Compostos de Bifenilo/antagonistas & inibidores , Cromatografia Líquida de Alta Pressão , Flavonoides/química , Flavonoides/isolamento & purificação , Flavonoides/farmacologia , Hidroxibenzoatos/química , Hidroxibenzoatos/farmacologia , Testes de Sensibilidade Microbiana , Fenóis/química , Fenóis/isolamento & purificação , Fenóis/farmacologia , Compostos Fitoquímicos/química , Compostos Fitoquímicos/farmacologia , Picratos/antagonistas & inibidores , Extratos Vegetais/química , Solventes , Especificidade da Espécie , Espectrometria de Massas em TandemRESUMO
The in vitro shoot propagation of Cannabis sativa L. is an emerging research area for large-scale plant material production. However, how in vitro conditions influence the genetic stability of maintained material, as well as whether changes in the concentration and composition of secondary metabolites can be expected are aspects that need to be better understood. These features are essential for the standardised production of medicinal cannabis. This work aimed to find out whether the presence of the auxin antagonist α-(2-oxo-2-phenylethyl)-1H-indole-3-acetic acid (PEO-IAA) in the culture media influenced the relative gene expression (RGE) of the genes of interest (OAC, CBCA, CBDA, THCA) and the concentrations of studied cannabinoids (CBCA, CBDA, CBC, ∆9-THCA, and ∆9-THC). Two C. sativa cultivars, 'USO-31' and 'Tatanka Pure CBD', were cultivated by in vitro conditions with PEO-IAA presence and then analysed. The RT-qPCR results indicated that even though some changes in the RGE profiles could be observed, no differences were statistically significant compared with the control variant. The results of the phytochemical analyses demonstrate that although there were some differences from the control variant, only the cultivar 'Tatanka Pure CBD' showed a statistically significant increase (at a statistical significance level α = 0.05) in the concentration of the cannabinoid CBDA. In conclusion, it would appear that using PEO-IAA in the culture medium is a suitable approach to improve in vitro cannabis multiplication.
RESUMO
Although medical cannabis was legalized in Czechia in 2013 and its use in topical treatments of skin disorders is now allowed, galenic formulations prepared from medical cannabis have not been widely implemented in the Czech healthcare system. One of the main reasons is the lack of a straightforward standardized protocol for their preparation. Cannabinoids, e.g., cannabidiol (CBD) and tetrahydrocannabinol (THC), have been shown to have therapeutic effects on various skin conditions, such as atopic dermatitis, psoriasis, scleroderma, acne and skin pigmentation. Recognizing the potential of dermatological treatment with medical cannabis, the present study aimed to evaluate the extraction capacity of various pharmaceutical bases for cannabinoids and the stability of prepared galenic formulations for dermatological applications with respect to cannabinoid content. The results showed that the stability of cannabinoids in formulations depended on the bases' physical and chemical properties. The highest THC decomposition was observed in cream bases and Vaseline, with estimated percentage loss of total content of up to 5.4% and 5.6% per week, respectively. In contrast, CBD was more stable than THC. Overall, the tested bases were comparably effective in extracting cannabinoids from plant material. However, olive oil and Synderman bases exhibited the highest cannabinoid extraction efficiencies (approximately 70%) and the best storage stabilities in terms of the content of monitored compounds. The proposed preparation protocol is fast and easily implementable in pharmacies and medical facilities.
RESUMO
Cannabinoids, a class of compounds derived from Cannabis sativa L., have recently become more widely accessible for public consumption in the form of diverse cannabis products, in parallel with weakening the measures that so far restricted their availability. The US Food and Drug Administration has approved several cannabis-derived drugs for management of various diseases as well as chemotherapy-induced nausea and vomiting. Besides the attenuation of adverse effects of chemotherapy, numerous reports about cannabinoid-mediated anticancer effects further motivate cancer patients to support their therapy with such products. Here we present a set of preclinical data with human cell culture models, suggesting that cannabidiol and cannabis extracts may effectively counteract the anticancer effects of the clinically widely used standard-of-care platinum-based drugs. We show that even low concentrations of cannabinoids reduced the toxicity of cisplatin, oxaliplatin, and carboplatin, an effect which was accompanied by decreased platinum adduct formation and a set of commonly used molecular markers. Mechanistically, our results excluded the possibility that the observed enhanced survival of cancer cells was mediated transcriptionally. Instead, trace metal analyses strongly indicate an inhibitory impact of cannabinoids on intracellular platinum accumulation, thereby implicating changes in cellular transport and/or retention of these drugs as the likely cause of the observed biological effects. Our study raises the possibility that the desirable effect of counteracting adverse effects of chemotherapy might, at least for some cannabinoids, reflect impaired cellular availability, and consequently attenuation of the anticancer effects of platinum drugs. DATA AVAILABILITY: All data supporting the conclusions are available in the article and supplementary files. Raw data are available upon request from the corresponding author.
Assuntos
Canabidiol , Canabinoides , Cannabis , Alucinógenos , Humanos , Preparações Farmacêuticas , Platina , Canabinoides/uso terapêutico , Canabidiol/farmacologia , Canabidiol/uso terapêutico , Agonistas de Receptores de Canabinoides , AnalgésicosRESUMO
Cannabidiolic acid (CBDA) and trans-Δ9-tetrahydrocannabinolic acid (trans-Δ9-THCA) are known to be the major phytocannabinoids in Cannabis sativa L., along with their decarboxylated derivatives cannabidiol (CBD) and trans-Δ9-tetrahydrocannabinol (trans-Δ9-THC). The cis isomer of Δ9-THC has been recently identified, characterized and quantified in several Cannabis sativa varieties, which had been heated (decarboxylated) before the analysis. Since decarboxylation alters the original phytocannabinoids composition of the plant, this work reports the identification and characterization of the carboxylated precursor cis-Δ9-THCA. The compound was also synthesized and used as analytical standard for the development and validation of a liquid chromatography coupled to high resolution mass spectrometry-based method for its quantification in ten Cannabis sativa L. samples from different chemotypes. The highest concentrations of cis-Δ9-THCA were found in CBD-rich varieties, lower levels were observed in cannabigerol (CBG)-rich varieties (chemotype IV) and in those varieties with a balanced level of both CBD and THC (chemotype III), while its levels were not detectable in cannabichromene (CBC)-rich varieties (chemotype VI). The presence of the cis isomer of THC and THCA raises the question on whether to include or not this species in the calculation of the total amount of THC to classify a cannabis variety as a drug-type or a fiber-type (hemp).
Assuntos
Canabidiol , Cannabis , Canabidiol/análise , Cannabis/química , Cromatografia Líquida de Alta Pressão/métodos , Dronabinol/análogos & derivados , Dronabinol/análiseRESUMO
During the last decade, the popularity of hemp products has been rising rapidly. Products containing cannabidiol (CBD) are of predominant interest. Traditional hemp products are frequently enriched by CBD due to their potential therapeutic effects. Cannabidiol occurs naturally in hemp juice together with other biologically active substances, such as terpenes, flavonoids, and stilbenoids. These constituents act synergistically. This study aimed to observe the influence of the hemp plant developmental stage on its chemical composition and antioxidant activity. The hemp plants were analyzed during three vegetative stages, i.e., before, during, and after flowering. The collected samples were evaluated using the following analyses: total polyphenolic content and profile, terpenoid and cannabinoid contents, and ferric reducing antioxidant power. The results revealed statistically significant differences between the samples in almost all set parameters. The optimal period for hemp harvest depends on desirable compounds, i.e., phenolic content is the highest before flowering, while the levels of cannabinoids and terpenoids are the highest during the flowering period.