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New Insights on Hemp Oil Enriched in Cannabidiol: Decarboxylation, Antioxidant Properties and In Vitro Anticancer Effect.

ABSTRACT: This study aimed to obtain and characterize extracted hemp oil enriched in cannabidiol (CBD) by decarboxylation of cannabidiolic acid (CBDA) and to give new insights into its antioxidant and anticancer effects. Optimization of CBDA decarboxylation in hemp oil was performed, and CBD and CBDA contents and purities were determined by flash chromatography, ¹H- and ¹³C-NMR. The antioxidant properties of CBD-enriched oil were investigated by Fe²⁺ chelating activity, Fe³⁺ reducing antioxidant power assay, O₂^●- scavenging activity, HO^● scavenging ability and lipid peroxidation inhibitory assay, and its cytotoxicity, apoptosis- and oxidative stress-inducing effects on NHDF, MeWo, HeLa, HepG2 and HOS cells were determined. The CBD concentration in hemp oil was increased by CBDA soft decarboxylation optimized at 90 °C, for 1 h and the resulting oil was capable of reducing iron, scavenging free radicals and inhibiting lipid peroxidation in cell-free oxidative conditions. CBD-enriched oil promoted NHDF proliferation at up to 15 µg CBD/mL, while inducing apoptosis and ROS production and modulating antioxidant enzymes' gene expression in cancer cells, being selective for osteosarcoma cells, and induced apoptosis by p53- and ROS-independent mechanisms. CBD-enriched hemp oil demonstrated antioxidant properties in oxidative conditions and promoted normal fibroblasts' proliferation, while inducing apoptosis and ROS production in cancer cells.

SUBMITTER: Petrovici AR

PROVIDER: S-EPMC8150740 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Cannabidiol Content and In Vitro Biological Activities of Commercial Cannabidiol Oils and Hemp Seed Oils.

Project description:Background: Hemp (Cannabis sativa L.) seed contains high contents of various nutrients, including fatty acids and proteins. Cannabidiol (CBD) is a non-psychoactive compound that can be extracted from C. sativa and used for treating epilepsy and pain. Industrial hemp products, including CBD and hemp seed oils, have become increasingly popular. Some products are marketed without a clear distinction between CBD and hemp seed oils. Herein, the CBD content and biological activities of commercial CBD and hemp seed oils were examined. Methods: CBD content was measured by high-performance liquid chromatography. For in vitro antioxidant activity determination, 2,2-diphenyl-1-picrylhydrazyl and 2,2'-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) radical-scavenging assays were performed. Results: The CBD concentrations in the two CBD oil samples were 18.9 ± 0.5 and 9.2 ± 0.4 mg/mL. Of the seven hemp seed oil samples, six samples contained CBD in concentrations ranging from 2.0 ± 0.1 to 20.5 ± 0.5 µg/mL, but it was not detected in one sample. Antioxidant activity was observed in both CBD oil samples. Conclusions: The results indicate that (1) CBD content varied by hemp seed oil sample and that (2) antioxidant activity could be a useful landmark for discriminating CBD oils from hemp seed oils.

| S-EPMC7555937 | biostudies-literature

The Antioxidant Role of Hemp Phytocomplex in Cannabis Oil-Based Extracts.

Project description:The therapeutic use of Cannabis oil extracts is constantly increasing. However, in Italy, they are allowed to be prepared with only a few methods and matrices. With this work, we aimed to assess how the different processes might affect the chemical composition of two different matrices (olive oils and medium chain triglycerides oils - MCT), accounting as variables for both the presence of Cannabis dried apices of the female flower and the adding of tocopherol acetate as an antioxidant. The macerated oils were prepared with four of the methods allowed according to the Italian legislation (Romano-Hazekamp, Cannazza-Citti, SIFAP and Calvi) and analyzed for normal and oxidized tocopherols, oxidized and conjugated fatty acids and volatile carbonyl compounds (VCCs), all using liquid chromatography coupled to UV or PDA detectors. According to our results, neither normal nor oxidized tocopherols are affected by the addition of antioxidants or Cannabis, while the oxidation state (according to the levels of oxidized and conjugated fatty acids) is often altered in either case. The VCCs concentrations, on the other hand, are never notably altered. These results suggest a worthless use of antioxidants in Cannabis macerated oils preparations, while the dried apices of female flowers might have a protective role in maintaining the oil oxidation state.

| S-EPMC9503170 | biostudies-literature

Pharmacokinetics of cannabidiol-/cannabidiolic acid-rich hemp oil in juvenile cynomolgus macaques (<i>Macaca fascicularis</i>).

Project description:IntroductionCannabinoids are increasingly popular in human and veterinary medicine and have been studied as an alternative treatment for a wide range of disorders. The goal of this study was to perform a pharmacokinetic analysis of oral cannabidiol (CBD)-/cannabidiolic acid (CBDA)-rich hemp oil (CBD/ArHO) in juvenile cynomolgus macaques (Macaca fascicularis).MethodsAfter a 2 mg/kg CBD/ArHO pilot study, 4 and 8 mg/kg direct-to-mouth CBD/ArHO were administered (n = 4 per dose) once daily for 14 days and blood was collected at 0-, 0.5-, 1-, 2-, 4-, 8-, 12-, and 24-h, and on Days 7 and 14, to quantify serum cannabinoid concentrations by high-performance liquid chromatography-tandem mass spectrometry. Serum biochemistries and complete blood counts were performed on Days 0, 1, and 14.ResultsThe maximum mean serum concentration (Cmax) of CBDA was 28.6-36.2 times that of CBD at 4 and 8 mg/kg. At 8 mg/kg, the Cmax of CBD was 1.4 times higher (p = 0.0721), and CBDA was significantly 1.8 times higher (p = 0.0361), than at 4 mg/kg. The maximum mean serum concentration of ∆9-tetrahydrocannabinol (THC) was 4.80 ng/mL at 8 mg/kg. Changes in serum biochemistries and complete blood counts over time were not clinically significant.DiscussionGiven the low serum CBD concentrations, the doses and frequency used in this study may be insufficient for a therapeutic effect of CBD in particular; therefore, clinical studies are needed to determine the therapeutic dose of CBD and CBDA for macaques, which may differ based on the disorder targeted.

| S-EPMC10716325 | biostudies-literature

Hemp seed (Cannabis sativa L.) enriched pasta: Physicochemical properties and quality evaluation.

Project description:Hemp seed (Cannabis sativa L.) contain large amounts of nutrients, e.g. protein, dietary fiber, minerals, and unsaturated fatty acids, which make them a good fortifying component in food production. The aim of the present study was to determine the effect of hemp addition on the physicochemical properties, cooking quality, texture parameters and sensory properties of durum wheat pasta. The samples were fortified with 5-40% of commercially available hemp flour or 2.5-10% of hemp cake obtained from hemp seed oil pressing. Our study showed that the addition of hemp seed raw materials led to an increase in the protein, total dietary fiber (TDF), ash and fat content in the pasta samples. Due to its lower granulation and higher nutritional value, hemp flour was found to be a better raw material for the fortification of pasta than hemp cake. Pasta enriched with hemp flour at the level of 30-40% contains 19.53-28.87% d.m. of protein and 17.02-21.49% d.m. of TDF and according to the EU, a definition can be described as a high-protein and high-fiber products. All enriched pasta samples were also characterized by safe Δ-9-tetrahydrocannabinol (THC) and cannabidiol (CBD) content, and their sensory properties were accepted by consumers.

| S-EPMC7971538 | biostudies-literature

Antioxidant Effects of Hemp (Cannabis sativa L.) Inflorescence Extract in Stripped Linseed Oil.

Project description:The ability of hemp (Cannabis sativa L.) inflorescence extract to counteract lipid oxidation was studied in stripped linseed oil. The ethanolic extract was characterized in terms of terpenes (6.00 mg/mL), cannabidiol (4.99% w/w), phenolic compounds (1.80 mg gallic acid equivalents (GAE)/mL), antiradical, and metal ion-chelating activities (50% effective concentration (EC50) of 2.47 mg/mL and 0.39 mg/mL, respectively). The stripped linseed oil, used as control (CO), was mixed with hemp extract (HO) or α-tocopherol (EO) at a ratio of 0.6% (w/w) and stored for 7 days in darkness at 40 °C. Hemp extract reduced the oxidation and lipolysis processes. At the end of the storage, HO showed a significantly higher level of α-linolenic acid (ALA; 26.64 g/100 g), lower peroxide value (PV) (21.19 meq O2/kg oil), and lower hexanal content (7.67 mmol/kg oil) than those found in the control. In contrast, EO showed a marked lipolysis (the free fatty acids increased by 42.57%) and a noticeable oxidation, since the ALA content decreased by 2.10% and a PV of 50 meq O2/kg oil was observed. This study demonstrates that hemp inflorescences can be used as a source of natural antioxidants in vegetable oils and lipid products to retard their oxidation, especially those characterized by a high degree of unsaturation.

| S-EPMC7697792 | biostudies-literature

Analytical method validation for assay determination of cannabidiol and tetrahydrocannabinol in hemp oil infused products by RP-HPLC.

Project description:A simple quantitative reverse phase high performance liquid chromatographic (RP-HPLC) method has been developed and validated for assay determination of cannabidiol and tetrahydrocannabinol in hemp oil infused products. The RP-HPLC method was developed and optimized for the mobile phase composition, flow rate, column selection and detector wavelength. An isocratic elution of samples were performed on SOLAS 100 Å C18 150 mm × 4.6 mm, 5 μm column with a mobile phase containing 75/25 acetonitrile/water v/v, with a flow rate of 1.5 mL/min by using an ultraviolet-visible (UV/Vis) detector operating at 214 nm. The RP-HPLC method was validated to meet regulatory requirements which covers specificity, accuracy, range, linearity, precision, system suitability and robustness. The validated assay test method was applied successfully to quantify cannabidiol and tetrahydrocannabinol in commercial hemp oil infused products such as tablets, soft gel capsules, plant extract oils, oral drops, tincture, and beverage enhancers. All the test results were found acceptable as per ICH guidelines, and this confirmed the feasibility of this method for its intended use in regular quality control and assay of cannabidiol and tetrahydrocannabinol in hemp oil infused products.

| S-EPMC9304360 | biostudies-literature

Anthocyanins enriched purple tea exhibits antioxidant, immunostimulatory and anticancer activities.

Project description:Purple coloured tea shoot clones have gained interest due to high content of anthocyanins in addition to catechins. Transcript expression of genes encoding anthocyanidin reductase (ANR), dihydroflavonol-4-reductase (DFR), anthocyanidin synthase (ANS), flavonol synthase (FLS) and leucoantho cyanidin reductase (LAR) enzymes in three new purple shoot tea clones compared with normal tea clone showed higher expression of CsDFR, CsANR, CsANS and lower expression of CsFLS and CsLAR in purple shoot clones compared to normal clone. Expression pattern supported high content of anthocyanins in purple tea. Four anthocyanins (AN1-4) were isolated and characterized by UPLC-ESI-QToF-MS/MS from IHBT 269 clone which recorded highest total anthocyanins content. Cyanidin-3-O-?-d-(6-(E)-coumaroyl) glucopyranoside (AN2) showed highest in vitro antioxidant activity (IC50 DPPH = 25.27 ± 0.02 ?g/mL and IC50 ABTS = 10.71 ± 0.01 ?g/mL). Anticancer and immunostimulatory activities of cyanidin-3-glucoside (AN1), cyanidin-3-O-?-d-(6-(E)-coumaroyl) glucopyranoside (AN2), delphinidin-3-O-?-d-(6-(E)-coumaroyl) glucopyranoside (AN3), cyanidin-3-O-(2-O-?-xylopyranosyl-6-O-acetyl)-?-glucopyranoside (AN4) and crude anthocyanin extract (AN5) showed high therapeutic perspective. Anthocyanins AN1-4 and crude extract AN5 showed cytotoxicity on C-6 cancer cells and high relative fluorescence units (RFU) at 200 ?g/mL suggesting promising apoptosis induction activity as well as influential immunostimulatory potential. Observations demonstrate potential of purple anthocyanins enriched tea clone for exploitation as a nutraceutical product.

| S-EPMC5495722 | biostudies-literature

Poly(cannabinoid)s: Hemp-Derived Biocompatible Thermoplastic Polyesters with Inherent Antioxidant Properties.

Project description:The legalization of hemp cultivation in the United States has caused the price of hemp-derived cannabinoids to decrease 10-fold within 2 years. Cannabidiol (CBD), one of many naturally occurring diols found in hemp, can be purified in high yield for low cost, making it an interesting candidate for polymer feedstock. In this study, two polyesters were synthesized from the condensation of either CBD or cannabigerol (CBG) with adipoyl chloride. Poly(CBD-Adipate) was cast into free-standing films and subjected to thermal, mechanical, and biological characterization. Poly(CBD-Adipate) films exhibited a lack of cytotoxicity toward adipose-derived stem cells while displaying an inherent antioxidant activity compared to poly(lactide) films. Additionally, this material was found to be semi-crystalline and able to be melt-processed into a plastic hemp leaf using a silicone baking mold.

| S-EPMC10270313 | biostudies-literature

The Anticancer, Antioxidant and Antimicrobial Properties of the Sesquiterpene β-Caryophyllene from the Essential Oil of Aquilaria crassna.

Project description:The present study reports a bioassay-guided isolation of β-caryophyllene from the essential oil of Aquilaria crassna. The structure of β-caryophyllene was confirmed using FT-IR, NMR and MS. The antimicrobial effect of β-caryophyllene was examined using human pathogenic bacterial and fungal strains. Its anti-oxidant properties were evaluated by DPPH and FRAP scavenging assays. The cytotoxicity of β-caryophyllene was tested against seven human cancer cell lines. The corresponding selectivity index was determined by testing its cytotoxicity on normal cells. The effects of β-caryophyllene were studied on a series of in vitro antitumor-promoting assays using colon cancer cells. Results showed that β-caryophyllene demonstrated selective antibacterial activity against S. aureus (MIC 3 ± 1.0 µM) and more pronounced anti-fungal activity than kanamycin. β-Caryophyllene also displayed strong antioxidant effects. Additionally, β-caryophyllene exhibited selective anti-proliferative effects against colorectal cancer cells (IC50 19 µM). The results also showed that β-caryophyllene induces apoptosis via nuclear condensation and fragmentation pathways including disruption of mitochondrial membrane potential. Further, β-caryophyllene demonstrated potent inhibition against clonogenicity, migration, invasion and spheroid formation in colon cancer cells. These results prompt us to state that β-caryophyllene is the active principle responsible for the selective anticancer and antimicrobial activities of A. crassnia. β-Caryophyllene has great potential to be further developed as a promising chemotherapeutic agent against colorectal malignancies.

| S-EPMC6331975 | biostudies-literature

Chemical Composition of <i>Ducrosia flabellifolia</i> L. Methanolic Extract and Volatile Oil: ADME Properties, In Vitro and In Silico Screening of Antimicrobial, Antioxidant and Anticancer Activities.

Project description:In the present study, the chemical composition of the volatile oil and methanolic extract from Ducrosia flabellifolia Boiss. was investigated. The antimicrobial, antioxidant, and anticancer activities of the methanolic extract from D. flabellifolia aerial parts were screened using experimental and computational approaches. Results have reported the identification of decanal (28.31%) and dodecanal (16.93%) as major compounds in the essential oil obtained through hydrodistillation. Farnesyl pyrophosphate, Methyl 7-desoxypurpurogallin-7-carboxylate trimethyl ether, Dihydro-Obliquin, Gummiferol, 2-Phenylaminoadenosine, and 2,4,6,8,10-dodecapentaenal, on the other hand, were the dominant compounds in the methanolic extract. Moreover, the tested extract was active against a large collection of bacteria and yeast strains with diameter of growth inhibition ranging from 6.67 ± 0.57 mm to 17.00 ± 1.73 mm, with bacteriostatic and fungicidal activities against almost all tested microorganisms. In addition, D. flabellifolia methanolic extract was dominated by phenolic compounds (33.85 ± 1.63 mg of gallic acid equivalent per gram of extract) and was able to trap DPPH• and ABTS•+ radicals with IC50 about 0.05 ± 0 mg/mL and 0.105 ± 0 mg/mL, respectively. The highest percentages of anticancer activity were recorded at 500 µg/mL for all cancer cell lines with IC50 about 240. 56 µg/mL (A-549), 202.94 µg/mL (HCT-116), and 154.44 µg/mL (MCF-7). The in-silico approach showed that D. flabellifolia identified compounds bound 1HD2, 2XCT, 2QZW, and 3LN1 with high affinities, which together with molecular interactions and the bond network satisfactorily explain the experimental results using antimicrobial, antioxidant, and anticancer assays. The obtained results highlighted the ethnopharmacological properties of the rare desertic D. flabellifolia plant species growing wild in Hail region (Saudi Arabia).

| S-EPMC9866066 | biostudies-literature

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