Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants

Borges, Rosivaldo S.; Batista, João; Viana, Rommel B.; Baetas, Ana Cristina; Orestes, Ednilsom; Andrade, Marcieni A.; Honório, Káthia Maria; Silva, Albérico Borges Ferreira da

doi:10.3390/molecules181012663

Cited by 108 publications

(89 citation statements)

References 42 publications

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“…THC has ameliorative effects as anti‐inflammatory and antioxidant . THC serves as cannabinoid receptors (CBs) agonist and plays a regulatory role in the expression of CBs and function of the pancreatic β cell .…”

Section: Discussionmentioning

confidence: 99%

The effects of delta‐9‐tetrahydrocannabinol on Krüppel‐like factor‐4 expression, redox homeostasis, and inflammation in the kidney of diabetic rat

Yanar

Coşkun

Beydogan

et al. 2019

J of Cellular Biochemistry

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Diabetes mellitus is a complex, multifactorial disorder that is attributed to pancreatic β cell dysfunction. Pancreatic β cell dysfunction results in declining utilization of glucose by peripheral tissues as kidney and it leads to nephropathy. Excessive production and accumulation of free radicals and incapable antioxidant defense system lead to impaired redox status. Macromolecular damage may occur due to impaired redox status and also immune imbalance. Δ9‐Tetrahydrocannabinol (THC) is the main active ingredient in cannabis. THC acts as an immunomodulator and an antioxidant agent. Our aim was to evaluate the effects of THC in the diabetic kidney. We analyzed macromolecular damage biomarkers as protein carbonyl (PCO), lipid hydroperoxide (LHP), malondialdehyde (MDA), 8‐hydroxy‐2′‐deoxyguanosine (8‐OHdG), and antioxidant defense system biomarkers as thiol fractions (T‐SH, NP‐SH, P‐SH) and Cu/Zn‐superoxide dismutase activity for the antioxidative effects of THC. Furthermore, mRNA expression of Krüppel‐like factor‐4, secreted immunopositive cell number changes of interleukin‐6, nuclear factor κβ (NF‐κβ), and peroxisome proliferator‐activated receptor‐γ and tumor necrosis factor α (TNF‐α) levels were analyzed for the immunomodulatory activity of THC. Diabetic rats showed significantly increased levels of PCO, LHP, MDA, and 8‐OHdG when compared with controls (P < 0.05 for each parameter). THC significantly reduced the elevated levels of PCO and 8‐OHdG (P < 0.05 for both parameters) and also LHP and MDA levels were insignificantly reduced by THC. Also, thiol fractions insignificantly increased in THC administered diabetic kidney when compared with diabetic rats. The NF‐κβ cell number significantly decreased in the diabetic rats treated with THC compared with the diabetic group. According to our data, THC has ameliorative effects on the impaired redox status of diabetic kidney and also it acts as an immunomodulator. Therefore, THC might be used as a therapeutic agent for diabetic kidneys but its usage in the healthy kidney may show adverse effects.

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Section: Discussionmentioning

confidence: 99%

The effects of delta‐9‐tetrahydrocannabinol on Krüppel‐like factor‐4 expression, redox homeostasis, and inflammation in the kidney of diabetic rat

Yanar

Coşkun

Beydogan

et al. 2019

J of Cellular Biochemistry

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“…Due to the hydroxyl groups (C-1 and C-5 in the B ring), CBD can also bind to amino acids such as threonine, tyrosine, glutamic acid, or glutamine by means of a hydrogen bond [17]. CBD has potential antioxidant properties because its free cationic radicals exhibit several resonance structures in which unpaired electrons are distributed mainly on ether and alkyl moieties, as well as on the benzene ring [18].…”

Section: Introductionmentioning

confidence: 99%

Antioxidative and Anti-Inflammatory Properties of Cannabidiol

2019

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Cannabidiol (CBD) is one of the main pharmacologically active phytocannabinoids of Cannabis sativa L. CBD is non-psychoactive but exerts a number of beneficial pharmacological effects, including anti-inflammatory and antioxidant properties. The chemistry and pharmacology of CBD, as well as various molecular targets, including cannabinoid receptors and other components of the endocannabinoid system with which it interacts, have been extensively studied. In addition, preclinical and clinical studies have contributed to our understanding of the therapeutic potential of CBD for many diseases, including diseases associated with oxidative stress. Here, we review the main biological effects of CBD, and its synthetic derivatives, focusing on the cellular, antioxidant, and anti-inflammatory properties of CBD.Antioxidants 2020, 9, 21 2 of 20 Moreover, this phytocannabinoid accelerated wound healing in a diabetic rat model by protecting the endothelial growth factor (VEGF) [11]. In addition, by preventing the formation of oxidative stress in the retina neurons of diabetic animals, CBD counteracted tyrosine nitration, which can lead to glutamate accumulation and neuronal cell death [12].This review summarizes the chemical and biological effects of CBD and its natural and synthetic derivatives. Particular attention was paid to the antioxidant and anti-inflammatory effects of CBD and its derivatives, bearing in mind the possibilities of using this phytocannabinoid to protect against oxidative stress and the consequences associated with oxidative modifications of proteins and lipids. Although CBD demonstrates safety and a good side effect profile in many clinical trials [4], all of the therapeutic options for CBD discussed in this review are limited in a concentration-dependent manner. Molecular Structure of CBDCBD is a terpenophenol compound containing twenty-one carbon atoms, with the formula C 21 H 30 O 2 and a molecular weight of 314.464 g/mol (Figure 1). The chemical structure of cannabidiol, 2-[1R-3-methyl-6R-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1, 3-benzenediol, was determined in 1963 [13]. The current IUPAC preferred terminology is 2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol. Naturally occurring CBD has a (−)-CBD structure [14]. The CBD molecule contains a cyclohexene ring (A), a phenolic ring (B) and a pentyl side chain. In addition, the terpenic ring (A) and the aromatic ring (B) are located in planes that are almost perpendicular to each other [15]. There are four known CBD side chain homologs, which are methyl, n-propyl, n-butyl, and n-pentyl [16]. All known CBD forms (Table 1) have absolute trans configuration in positions 1R and 6R [16].

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“…The authors noted that there was a greater efficacy against glutamate‐induced neurotoxicity than with ascorbate or α‐tocopherol. This suggests that CBD has potential therapeutic application in neurodegenerative disorders associated with OS …”

Section: Resultsmentioning

confidence: 98%

“…This suggests that CBD has potential therapeutic application in neurodegenerative disorders associated with OS. 13,17,18,33,[37][38][39][40][41] Rajan et al evaluated the anti-inflammatory, antioxidative and anti-apoptotic effects of low doses of CBD. The results showed that 5 lM CBD had a moderate anti-inflammatory effect (TNF-a, IL-10) and oxidative markers (inducible nitric oxide synthase, nuclear factor erythroid 2-related factor 2, nitrotyrosine).…”

Section: Phasementioning

confidence: 99%

Cannabidiol: an alternative therapeutic agent for oral mucositis?

et al. 2017

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SUMMARYWhat is known and objective: Chemo-and radiotherapy are therapeutic modalities often used in patients with malignant neoplasms. They kill tumour cells but act on healthy tissues as well, resulting in adverse effects. Oral mucositis is especially of concern, due to the morbidity that it causes. We reviewed the literature on the etiopathogenesis of oral mucositis and the activity of cannabidiol, to consider the possibility of its use for the prevention and treatment of oral mucositis. Methods: We searched the PubMed database and selected complete articles published in English that met the inclusion criteria for the period 1998-2016. The search terms 'cannabinoids', 'cannabidiol', 'oxidative stress', 'antioxidants' and 'oral mucositis' were used. Results and discussion: The control of oxidative stress may prevent and alleviate oral mucositis. Studies have demonstrated that cannabidiol is safe to use and possesses antioxidant, antiinflammatory and analgesic properties. What is new and conclusions: The literature on the use of cannabidiol in dentistry is still scarce. Studies investigating the use of cannabidiol in oral mucositis and other oxidative stressmediated side effects of chemotherapy and radiotherapy on the oral mucosa should be encouraged. WHAT IS KNOWN AND OBJECTIVEWith an increase in life expectancy and an ageing population, the frequency of chronic non-communicable diseases such as cancer has been increasing. Consequently, there is a greater demand for antineoplastic treatments, which are responsible for major adverse effects. Oral mucositis (OM) is a complication commonly observed, particularly with radiotherapy (RT) of the head and neck area and with chemotherapy (CT). It is a painful and debilitating condition of varying severity. It is characterized by the presence of ulcerated lesions in the oral cavity, which usually leads to difficulty in eating and consequential loss of weight and malnutrition, and susceptibility to opportunistic infections. OM affects the quality of life of patients and can become a dose-limiting factor in treatment. [1][2][3][4][5][6] There is considerable evidence that the cytotoxic effects of CT and RT result from physico-chemical reactions that lead to excessive production of free radicals (FR), which favours an oxidant-antioxidant imbalance and oxidative stress (OS). This could mediate the development of oral lesions and OM. 4,5,[7][8][9][10][11] However, despite our understanding of the pathogenesis of this condition, its prevention and treatment are still considered a challenge to the dentist.The use of cannabinoids, components of Cannabis sativa, in the treatment of complex diseases has been extensively investigated in different medical areas. Among the cannabinoids, cannabidiol (CBD) is the non-psychotropic cannabinoid of greatest abundance in the plant.12 According to reported studies, CBD has antioxidant, anti-inflammatory and immunomodulatory properties and is devoid of psychoactive properties, and its minimal side effects make it safe for use in humans. [12][...

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Understanding the Molecular Aspects of Tetrahydrocannabinol and Cannabidiol as Antioxidants

Cited by 108 publications

References 42 publications

The effects of delta‐9‐tetrahydrocannabinol on Krüppel‐like factor‐4 expression, redox homeostasis, and inflammation in the kidney of diabetic rat

The effects of delta‐9‐tetrahydrocannabinol on Krüppel‐like factor‐4 expression, redox homeostasis, and inflammation in the kidney of diabetic rat

Antioxidative and Anti-Inflammatory Properties of Cannabidiol

Cannabidiol: an alternative therapeutic agent for oral mucositis?

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