Inhibition of aldose reductase activity by   chemotypes extracts with high content of cannabidiol or cannabigerol

Smeriglio, Antonella; Giofrè, Salvatore V.; Galati, E. M.; Monforte, M. T.; Cicero, Nicola; D’Angelo, Valeria; Grassi, Gianpaolo; Circosta, Clara

doi:10.1016/j.fitote.2018.02.002

Cited by 41 publications

(41 citation statements)

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“…The therapeutic potential of CBD has been evaluated in cardiovascular, neurodegenerative, cancer, and metabolic diseases, which are usually accompanied by oxidative stress and inflammation [6]. One of the best studied uses of CBD is for therapeutic effect in diabetes and its complications in animal and human studies [7]. CBD, by activating the cannabinoid receptor, CB2, has been shown to induce vasodilatation in type 2 diabetic rats [8,9], and by activating 5-HT 1A receptors, CBD showed a therapeutic effect in diabetic neuropathy [10].…”

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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Section: Introductionmentioning

confidence: 99%

Antioxidative and Anti-Inflammatory Properties of Cannabidiol

2019

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“…However, a number of other compounds such as alkanes and some phytocannabinoids, like those having propyl side chains, common only in a specific cannabis biotype (Hendriks, Malingré, Batterman, & Bos, ; Hillig & Mahlberg, ; Ross & ElSohly, ), were found. Recently, a growing interest has been focused on C. sativa biotypes with low content of Δ 9 ‐tetrahydrocannabinol (Δ 9 ‐THC <0.2%) and with a high titre of non‐psichotropic cannabinoids such as cannabidiol (CBD)/cannabidiolic acid (CBDA) or cannabigerol (CBG)/cannabigerolic acid (CBGA) (Smeriglio et al, ). This, for a possible use in therapy of Cannabis ‐based medicinal extracts free of the Δ 9 ‐THC psychotropic side effects (Iuvone et al, ).…”

Section: Introductionmentioning

confidence: 99%

Promising in vitro antioxidant, anti‐acetylcholinesterase and neuroactive effects of essential oil from two non‐psychotropic Cannabis sativa L. biotypes

Smeriglio

Trombetta

Alloisio

et al. 2020

Phytotherapy Research

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The aim of this study was to compare the micro‐morphological features of two different non‐drug Cannabis sativa L. biotypes (Chinese accession G‐309 and one fibrante variety) and to evaluate the phytochemical profile as well as some biological properties of the essential oils (EOs) obtained by hydrodistillation of dried flowering tops. After a micro‐morphological evaluation by scanning electron microscopy, the phytochemical composition was analysed by GC–FID and GC–MS analyses. Antioxidant and anti‐acetylcholinesterase properties were investigated by several in vitro cell‐free assays, while neuroactive effects were evaluated on mouse cortical neuronal as well as human iPS cell‐derived central nervous system cells grown on MEA chips. Both EOs showed strong antioxidant properties mainly attributable to the high content of hydroxylated compounds as well as significant anti‐acetylcholinesterase activities (IC50 74.64 and 57.31 μg/ml for Chinese accession and fibrante variety, respectively). Furthermore, they showed a concentration‐dependent inhibition of spontaneous electrical activity of human and mouse neuronal networks, with the fibrante variety, which showed the best activity (MFR, IC50 0.71 and 10.60 μg/ml, respectively). The observed biological activities could be due to a synergic effect between terpenes and phytocannabinoids, although in vivo studies, which clarify the molecular mechanism, are still lacking.

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“…Chromatographic separation of the EtOAc extracts from the aerial parts of C. sativa yielded ve new compounds (1-5) and twelve known compounds (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17), named D 9 -trans-tetrahydrocannabivarin (6), 22 cannabinol (7), 23 cannabispirone (8), 24 erythrodiol (9), 25 oleanolic acid (10), 26 maslinic acid (11), 27 phydroxybenzaldehyde (12), 28 (E)-methyl p-hydroxycinnamate (13), 29 (Z)-methyl p-hydroxycinnamate (14), 30 ferulic acid (15), 31 phylligenol (16), 32 and skullcapavone II (17) 33 (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

“…In summary, three new cannabinoids, cannabisativas A-C (1-3), two new phenolic acids, (7Z,9Z)-cannabiphenolic acid A (4) and (8S,9Z)-cannabiphenolic acid B (5), along with twelve known compounds (6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17), were identied from the aerial parts of Cannabis sativa L. subsp. sativa.…”

Section: Discussionmentioning

confidence: 99%

“…It has been indicated that long term intake of fruits of C. sativa beneted for the health and longevity of local people. 11,12 The extracts of C. sativa have been demonstrated to have analgesic, antiemetic, and anxiolytic activities. [13][14][15] A number of chemical constituents, e.g., cannabinoids (CBDs), mono-and sesquiterpenes, steroids, avonoids, and nitrogenous compounds, were reported from C. sativa.…”

Section: Introductionmentioning

confidence: 99%

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