Cannabis produces compounds that bind to certain receptors on our cells. There are more than of these compounds in each cannabis. In this guide, we are exploring how marijuana helps with diabetes and then Cannabinoids: A Guide to 13 Bioactive Compounds from Weed. Cannabis is a complex plant, with major compounds such as The second compound found was cannabidiol (CBD) by Mechoulam and Shvo [Mechoulam and Chems Phys Lipids 1–13 [PubMed]; Mechoulam R., Shvo Y. () Hashish. . J Med Chem – [PubMed]; Russo E. B. () Handbook of.
Weed Compounds from Guide to A Cannabinoids: Bioactive 13
The inducible expression will limit the negative effects caused by the toxicity of the accumulating cannabinoids during the growth of the transformed plant cells as more thoroughly described in the next section.
Workflow showing the achievements in green and potential future approaches in light blue to produce cannabinoids in cultures of Cannabis , as well as other plant hosts. In addition to the genetic engineering approach, plant cell suspension cultures can be elicited to boost the production of secondary metabolites. The literature is rich in examples concerning the increased expression of secondary metabolites in plant cells elicited with different factors reviewed recently by Ncube and Van Staden, Both biotic and abiotic stress factors can indeed be used to re-direct the plant metabolism: In hemp suspension cells, elicitation with biotic and abiotic elicitors did not induce an increase in cannabinoids Flores-Sanchez et al.
It is here worth mentioning the effect of a so far neglected element, silicon Si. Despite being a non-essential element for plant growth, Si is known to increase plant vigor and to alleviate the effects of exogenous stresses Epstein, Very recently Si was shown to alleviate the effects of salt stress and to induce the production of chlorogenic acid in Lonicera japonica Gengmao et al.
Given the stimulatory effects that Si has on plant metabolism, it is interesting to further investigate, from a molecular perspective, the effects of Si supplementation on Cannabis secondary metabolite production. Cyclodextrins have also been used in plant cell suspension cultures to enhance the production of various non-polar metabolites such as stilbenes Yang et al.
They are known to form inclusion complexes with lipophilic compounds, including cannabinoids Hazekamp and Verpoorte, , in their hydrophobic cavity, thereby improving metabolite solubility in an aqueous environment. It would therefore be worth investigating the effect of cyclodextrins on the production of the non-polar cannabinoids in hemp suspension cell cultures. For example synthetic biology could be used to recreate the cannabinoid biosynthetic pathway in heterologous plant cells via the expression of THCAS, together with the upstream enzymes involved in the synthesis of CBG, i.
Examples for the occurrence of metabolons exist in plants for pathways involving, e. Entire metabolic pathways can be engineered via the use of synthetic metabolons enabling the association of enzymes in close proximity: One possible way to assemble a synthetic metabolon is via the use of a scaffolding protein enabling the association of the enzymes Singleton et al. The assembly of multimodular constructs for expression in plants is no longer an insurmountable challenge, thanks to the development of methods like the Gateway-mediated cloning reviewed by Dafny-Yelin and Tzfira, , Golden Gate Binder et al.
When cannabinoids are produced in heterologous plant hosts, toxicity effects have to be taken into account, as it was shown that THCA and CBGA cause cell death via apoptosis in cells of Cannabis and tobacco BY-2 Sirikantaramas et al. For plant cell suspension cultures cultivated in bioreactors, the in situ product removal via a two-phase culture system might be useful to favor the accumulation of the toxic metabolites produced in sites which are separated from the cells Cai et al.
The use of adsorbents in the culture medium can not only sequester the toxic compounds, but also stimulate the secondary metabolite biosynthesis Cai et al. This approach has been recently proposed in A. The authors induced the formation of an artificial compartment generated by membranes deriving from endocytosis and the endoplasmic reticulum-vacuole trafficking via the expression of a truncated SNARE protein, AtSYP The creation of an artificial compartment can be used for the production of cannabinoids, because it can trap and stabilize the toxic secondary metabolites until extraction is performed, in a manner analogous to what discussed for artemisinin.
Hemp is a unique versatile plant, which can provide high biomass quantities in a short time. Hemp stem is used as a source of woody and bast fibers for the construction and automotive industries, while hemp seeds are used as a source of dietary oil and hemp leaves and flowers as a source of bioactive components.
To date, more than phytochemicals have been described in hemp Gould, , and their pharmacological properties appear to go much beyond psychotic effects, with the capacity to address needs like the relief of chemotherapy-derived nausea and anorexia, and symptomatic mitigation of multiple sclerosis. Nature has already provided a large source of new molecules and new skeletons. Cannabis presents a colossal potential for enlarging the library of bioactive metabolites.
Compounds can be obtained from hemp trichomes, cell suspension cultures, hairy root systems, or via the biotransformation of THCA or CBDA using fungal, bacterial, or plant cells Akhtar et al. Apart from the importance of studies focused on improving Cannabis genetic transformation, it is necessary to know more about the regulatory mechanisms involved in secondary metabolite production in C. For example enzymological and structural studies will help devise protein engineering approaches to improve the catalytic functions of key enzymes Taura et al.
However, further studies would still be needed to elucidate other key genes involved in biosynthetic pathways of, for instance, less-abundant cannabinoid derivatives. For that purpose, the combination of metabolomics with genome-based functional characterizations of gene products would provide an accelerated path to discovering novel biosynthetic pathways to specialized metabolites.
Indeed, the functions of numerous genes have been identified and characterized through the correlation of gene expression and metabolite accumulation Sumner et al. Classical approaches used focused on the spatial and temporal distribution of the targeted phytochemicals and on the plant transcriptome, as influenced by the developmental stage and environmental stresses.
With respect to the resurgence of interest in Cannabis phytochemicals nowadays, the results of such studies will be soon available. CA was involved in the review writing, J-FH was involved in manuscript refinement, and GG initiated the idea of the review and was involved in the manuscript writing. The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest.
The authors are grateful to Dr David J. National Center for Biotechnology Information , U. Journal List Front Plant Sci v. Published online Feb 4. Author information Article notes Copyright and License information Disclaimer. This article was submitted to Plant Biotechnology, a section of the journal Frontiers in Plant Science. Received Oct 27; Accepted Jan 8. The use, distribution or reproduction in other forums is permitted, provided the original author s or licensor are credited and that the original publication in this journal is cited, in accordance with accepted academic practice.
No use, distribution or reproduction is permitted which does not comply with these terms. This article has been cited by other articles in PMC.
Abstract Cannabis sativa L. Introduction The current climatic and economic scenario pushes toward the use of sustainable resources to reduce our dependence on petrochemicals and to minimize the impact on the environment.
A Source of Fibers with Antibacterial Properties Plant lignocellulosic biomass is an abundant renewable resource, which can provide biopolymers, fibers, chemicals and energy Guerriero et al. Open in a separate window. Their Production Pathways and Myriad of Biological Activities Numerous chemicals are produced in hemp through the secondary metabolism. Phytocannabinoids Phytocannabinoids represent a group of C21 or C22 for the carboxylated forms terpenophenolic compounds predominantly produced in Cannabis.
Table 1 Summary of the concentrations in cannabinoids found in different parts of the hemp plants, in vitro hairy roots, and some commercial medicinal products. The most recent references have been used, when available. Health Benefits Linked to Cannabinoids The pharmacology of phytocannabinoids has previously been reviewed elsewhere Pacher et al. Adverse Health Effects of Cannabinoids As mentioned earlier, the recreational and medical use of Cannabis as well as of THC and other synthetic cannabinoids have also been associated with numerous side effects.
Terpenes Terpenes form the largest group of phytochemicals, with more than molecules identified in Cannabis Rothschild et al. Health Benefits Associated with Terpenes Terpenes are lipophilic compounds that easily cross membranes and the blood-brain barrier in particular Fukumoto et al. Phenolic Compounds Phenolic compounds, also known as phenylpropanoids, constitute one of the most widely distributed group of secondary metabolites in the plant kingdom.
Health Benefits Associated with Phenolic Compounds In plants, phenolic compounds may act as antioxidants under certain physiological conditions and, thereby, protect plants against oxidative stress. Synergistic and Antagonistic Effects Between Phytochemicals It is now well accepted that the health benefits of fruits, vegetables and other plant foods are due to the synergy or interactions between the different bioactive compounds or other nutrients present in the whole foods, and not to the action of a sole compound Liu, Small Factories of Phytochemicals Trichomes are epidermal protuberances covering the leaves, bracts and stems of plants and some of them, like the glandular trichomes, are capable of secreting or storing secondary metabolites as a defense mechanism.
Cannabis In Vitro Propagation and Transformation The cultivation of Cannabis is severely regulated in many countries; therefore alternative in vitro growth techniques are receiving a lot of attention. Hairy Root Cultures for the Production of Cannabinoids An additional system offering interesting applications for the industrial production of compounds showing pharmaceutical effects in humans is the hairy root system, a type of Agrobacterium -transformed plant tissue culture used to study plant metabolic processes.
Cannabis Cell Suspension Cultures for the Production of Cannabinoids Plant cell suspension cultures offer important advantages, as they can be transformed and then cultivated in bioreactors for the production of useful metabolites Weathers et al.
Cannabinoid Production in Heterologous Plant Hosts: Perspectives and Conclusion Hemp is a unique versatile plant, which can provide high biomass quantities in a short time. Author Contributions CA was involved in the review writing, J-FH was involved in manuscript refinement, and GG initiated the idea of the review and was involved in the manuscript writing.
Conflict of Interest Statement The authors declare that the research was conducted in the absence of any commercial or financial relationships that could be construed as a potential conflict of interest. Dietary antioxidants and oxidative stress from a human and plant perspective: Gene expression changes related to the production of phenolic compounds in potato tubers grown under drought stress.
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Targeting inflammatory pathways by triterpenoids for prevention and treatment of cancer. In particular, cannflavin A and B are known to possess an anti -. In addition to flavonoids,. As to canniprene, it has been demonstrated to. Several biological effects have. As to canniprene, it has been demonstrated. Molecules , 23 , 3 of Chemical structures of main flavonoids and related compounds in hemp inflorescences.
As regards the other compounds presen t in hemp, terp enes are responsible for the characteristic. The main v olatiles detected in the aerial parts of the plant include both mono -. Chemical structures of main terpenes in hemp inflorescences. Some bio logical activities of cannabinoids are known to be enhanced by the pres ence of o ther.
This effect has been attributed to a strict interaction between cannabinoids and terpenes, resulting in. As an example, terpenes are able to increase blood-brain barrier permeability. Finally, also flavonoids may modulate the. With this in v iew, the development and application of advanced analytical methods for a. In the l ight of all the above, the present study was aimed at the firs t multi-component analysi s.
ESI- MS 2 method, together with a selective extraction protocol, was developed a s well and applied for. As regards the other compounds present in hemp, terpenes are r esponsible for the characteristic. The main volatiles detected in the aerial parts of the plant include both mono-.
Some biological activities of cannabinoids are known to be enhanced by the presence of other. This effect has been attributed to a strict interaction between cannabinoids and terpenes, resulting in a. With this in view , the development and application of advanced analytical methods for a. The study on C. Molecules , 23 , 4 of The development and application of a suitable extraction procedure covers a crucial role to.
For what concerns cannabinoids, a simple. EtOH is indeed a good solvent for the extraction of many phenolics from plant. For this reason, two different protocols were optimised and applied in this work for the. Starting with the extraction conditions previously optimised for cannabinoids, the method was. First, the solvent was properly chosen in order to have a good yield of hemp. The extracts were also concentrated Of the solvents tested, acetone resulted in being the best one and it was therefore.
The development and application of a suitable extraction procedure covers a crucial ro l e t o. EtOH is indeed a good solvent fo r the extraction of many p henolics from.
As a matter of fact, cannflavins A and B were detected in h em p ethanolic extracts. For this reason, two different protocols were opti mised and applied in this. Starting with the e xtraction conditions previously optimised for cannabinoids, the method was. The extract s were also co ncentrated Of the solvents tested, acetone resulted in be ing the best one and it was therefore.
For peak numbering, see Table 1. In order to reduce any possible interference from cannabinoids in the concentrated extract, a. Indeed, the amount of cannabinoids in hemp. Co nversely to othe r. After this treatment, the resi due was extracted. As shown in Figure 5, n -hexane alone resulted in be ing. Indeed, its combination wi th DCM o r ethyl ether or toluene, l ed to a decrease in the final.
For peak numbering, see T able 1. In order to reduce any possible interference from cannabinoids in the concentrated extract,. After this treatment, the residue was extracted three. As shown in Figure 5 , n -hexane alone resulted in being the most. Molecules , 23 , 5 of Chromatograms obtained at nm with pre-maceration with n- hexane 3x blue. Effect of pr e-maceration w ith n -hexane on cannabinoid removal from hemp sample C6. Chromatograms obtained at nm with pre -maceration with n -hexane 3x blue line and.
Finally, in order to facilitate the removal of cannabinoids, a decar boxylation of the plant material,. As shown in Figure 6 , the peak areas rel ated to flavonoids. In the light of all the above, a two-step extracti on, based on an.
Chromatograms obtained at nm without thermal treatment blue line , with thermal treatment at. For peak numbering, see. Fo r peak numbering, see. The o ptimized extractio n techniques, based on dynamic maceration at roo m temperature, did. Chromatograms obtained at nm with pre-maceration with n- hexane 3x blue line , with. Finally , in order to facilitate the removal of cannabinoids, a decarboxylation of the plant material,. In particular, the plant.
C for 2 h, respectively. As shown in Figure 6. In the light of all the above, a two-step extraction, based on an initial pre-maceration of the. C for 2 h red line , with thermal treatment at C for 1 h green line.
Effect of different thermal treatments on cannabinoid r emoval from hemp sample C6. Chromatograms obtained at nm without thermal treatment blue line , with thermal treatment. The optimized extraction techniques, based on dynamic maceration at room temperature, did not.
Molecules , 23 , 6 of The aim of the present study was to provide a comprehensive analysis of the main bioactive. In this perspective, the development of HPLC. ACN used as the strong solvent eluent and acidic H. Indeed, the use of an acidic mobile. For our purpose, an Ascentis Express C. O and ACN, both containing 0. Representative chromatograms obtained by using the two HPLC. The aim of the present study was to provide a comp rehensive analysis of the main bioactive. In this perspective, the deve lopment of HPLC.
Indeed, the use of an acidic. For our purpose, an Ascentis. The gradient el ution with the same mobile phase was then properl y modified for hemp. Under the final conditions, a good resol ution of peaks belonging to cannfl avins A and. B and other hemp phenolics was ac hieved. Representative chromatograms obtained by using the. The identification of secondary metabol ites in hemp extracts was carri ed out by combining the.
For a compl ete characterisation, the. The UV spectra were used to preliminarily assign the chromatographic peaks to a chemical. Also cannflavins can b e. C6 at nm obtained by using the analytical method optimised for cannabinoids.
For a complete characterisation,. The UV spectra were used to preliminarily assign the chromatographic peaks to a chemical class. Molecules , 23 , 7 of The MS and MS. In particular, cannabinoic acids showed a. As to their MS. As to canniprene, the MS spectrum carried out in the. The fragmentation of CBD in the negative ion-mode provided. Canniprene generated its pseudo-molecular ion [M.
The limit of detection LOD values for chrysoeriol and canniprene were 0. By taking into account all the information described above, it can be concluded that this method. Molecules , 23 , 8 of Experimental conditions as described in Sections 3. Molecules , 23 , 9 of Since all the samples. In particular, samples C1, C3, and C6 showed the typical.
On the other hand, samples C2, C4, and C5 showed the opposite behaviour: The same trend was observed also for the other two major non-psychoactive cannabinoids, namely. Nevertheless, the amount of non-psychoactive cannabinoids.
Experimental conditions as in Section 3. Canniprene was not detected in any of the samples. Molecules , 23 , 10 of In this study, a new HS-. SPME procedure was optimised in o rder to achieve a reliable characterisation of the volatiles from. Firstly, the perfo rmance of two different SPM E fibres was assessed, incl uding both a.
In order to compare the fi bre performance, the same temperature, equilibrium time, and e xtraction. The extraction efficiency of volatile compounds was found to be higher when. For the outcome of the o verall extraction procedure, it is also important to properly set the. On t he basis of. For the outcome of the overall extraction procedure, it is also important to properly set the.
On the basis of. Molecules , 23 , 11 of Molecules , 23 , 12 of In general, all the hemp samples analysed in this study displayed the same qualitative and.
Sample C5 was the only exception to. It is worthy of notice that the head space of sample C2 had a remarkably high relative.
Curiously, sample C5 was the one with the higher relative content. It should be pointed out that samples C2 and C5 were. It is worthy of notice tha t the head space of sample C2 had a rem arkably high relative. Curiously, sample C5 was the one w i th the higher relative. It should be pointed out that samples C2. Nevertheless, the GC data of the hemp inflorescences anal ysed in this work are in accordance. Molecules , 23 , 13 of Molecules , 23 , 14 of Experimental conditions as in Sections 3.
Molecules , 23 , 15 of Chrysoeriol was purchased from Sigma-Aldrich Milan, Italy , while. Federica Pollastro of the Department of Drug Sciences. C5 , and Fibrante C6. These samples about — g dry material each , belonging to different. All the samples considered in this study were approved for.
C until required for chemical analysis. Extraction of Non-Psychoactive Cannabinoids. The extraction procedure was repeated twice for each sample. Extraction of Flavonoids and Related Compounds. A portion of 0. The same procedure was repeated twice. The residue was then let to dry. Molecules , 23 , 16 of The SPME device was then inserted into the sealed vial by manually penetrating the. C was used in the split-less mode.
The extraction procedure was repeated three times for each sample. The chromatographic conditions for the analysis of non-psychoactive cannabinoids were set on.
O and B ACN. The post-running time was 15 min. The column temperature was set at Three injections were performed for each sample. The post-running time was 10 min. Molecules , 23 , 17 of In details, the chromatographic conditions described in Sections 3.
For the negative ion mode, the MS conditions were. SmartFrag function, which automatically selects the precursor ion to be fragmented and it eliminates.
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The study on Cannabis volatile compounds was performed by developing a new .. used for the analysis of cannabinoids in C. sativa extracts [3,9,13,16]. . of flavonoids in fibre-type hemp, conforming to the ICH guidelines. Bioactive Compounds in Cannabis sativa L. (hemp) the analysis of cannabinoids in C. sativa extracts [. 3.,. 9.,. ,. ] was performed in agreement with the international guidelines for analytical techniques for the. using any information, methods, compounds, or experiments described herein. Cannabis Body Packing: A Caribbean. Perspective. S.O. CAWICH, D. DAN, V. NARAYNSINGH . and 2-Arachidonoyglycerol as Bioactive Lipids