May 11, 2015

Beyond THC – Cannabis sativa (L.) the plant


Laurie Caron, Chemist, M.Sc. - Plant Card
 

Often, cannabis is associated with its recreational activity and its many adherents. In the past year, PhytoChemia has made a full review of literature on the properties of boreal resources for Agroboréal. This scientific review is available on the site web of this company in French version only (http://agroboreal.com/revue-litterature-les-proprietes-ressources-boreales).
For this post, I took the full card description of Cannabis sativa (L.) and translated it in english to put it in our blog. This information card lists the biological activities, commercial and medicinal potential and other scientific knowledge on the plant.
 

Photo credit : Huffington Post Quebec



CANNABIS SATIVA (L.)

Plant description 
Strong plant, erect, rough, inner bark made with very resistant fiber with thin leaves, opposite or alternate, divided into 5-11 linear-lanceolate segments1 . The fruit is a compressed achene.

Related species 
Monotypic genus, it is found throughout Quebec except in cold regions. Naturalized from Eurasia1.

Natural habitat 
Cannabis sativa (L.) is grown in North America for several centuries and is a good example of a colonizing plant, because cannabis is very well adapted to the new conditions of crops. This plant is found near inhabited areas where soils are moist and rich in manure and located in open areas2. In Canada, it's also possible to find several spontaneous settlements of this plant in all the provinces, but also in wild forms along the St. Lawrence river and Great Lakes2.

Other names

Hemp, canadian weeds, marijuana, marihuana, chanvre cultivé, chanvre indien, chanvre.

Chemical compounds
 
Chemical compounds in C. sativa (L.) are part of the cannabinoids family. Notably, five compounds predominate in the plant : cannabidiol, cannabichromene, cannabigerol, Δ-9-tetrahydrocannabinol and cannabinol3. Hemp is grown for several commercial uses and chemical composition varies depending on type. The hemp grown for its resin contains Δ-9-tetrahydrocannabinol (THC) and acid Δ-9-tetrahydrocannabinolic (Δ-9-THCA) in higher concentration in its inflorescences. The hemp who is grown for its fibers ( industrial hemp) is known to contain an high level of cannabidiol (CBD) and cannabidiolic acid4. The Δ- 9 -THCA is the compound known to be ''the drug compound'', and is extracted from mature dry inflorescences of the plant5. In Canada, legal productions of this plant are regulated by canadian laws6.Cannabinoid compounds such as THC are used  to do the quality control of the plant7,8. Over 97 types of cannabinoid compounds have been identified in the scientific literature  in C. sativa (L.) (Figure 1 - Poster: The Cannabinoids: beyond the THC). The essential oil of C. sativa L. buds contains  monoterpenes (92%) and sesquiterpenes (7%)9. Other less important compounds such as esters and ketones are present up to 1% in the essential oil. The two main monoterpenes found in this oil is the β-myrcene (67%) and limonene (16%)9.


Figure 1 : Poster showed the 97 cannabinoids present in C.sativa (L.).



Biological activities
C. sativa (L.) is known to contain psychotropic compounds (Δ-9-tetrahydrocannabinol and cannabinol) in these leaves and these inflorescences10,  but this plant has other biological activities. Since the 80's in the United States, the Department  of "Food and Drug Administration" allows medical and therapeutic uses of cannabis to help relieve nausea and vomiting in patients undergoing chemotherapy treatment11. In 2008, a study on the process of meta-analysis demonstrated that cannabis had superior efficacy as an antiemetic compared to other pharma drugs11. The cannabinoids from C. sativa (L.) are also known for their antibacterial potential12. A study has  shown that the main compounds of C. sativa (L.) (cannabidiol, cannabichromene, cannabigerol, Δ-9-tetrahydrocannabinol and cannabinol) had a good antibacterial activity against a variety of methicillin-resistant Staphylococcus aureus (MRSA )3.

Chemotype
Three types of chemotypes are listed in the literature such as : Chemotype I, which contains more than 0.3% of Δ-9-tetrahydrocannabinol (THC) and less than 0.5% of cannabidiol (CBD). Chemotype II, called intermediate chemotype, contains CBD as the main compound and THC shows a high variable concentration13. Finally, chemotype III, contains a very low concentration of THC13. These different chemotypes appear to be associated with their geographical origin and not to the environment or heredity of the plant13. A French study mentioned that there are other groups as chemotypes according to the usefulness of the type of plant (drug or fiber) and the environmental characteristics  area of the plant. These chemotypes are characterized as follows10:

1. The first chemotype is a "drug type" (THC> 1 p. 100 and CBD = 0) and grows in warm climates in countries such as Mexico and South Africa.

2. The second chemotype is a "intermediate drug type" (THC> 0.25 p. 100 and CBD> 0.5 p. 100) and also grows in warm climates, but comes from Mediterranean countries such as Morocco and Lebanon.

3. The third chemotype is a "fiber type" (THC <0.25 p. 100 and CBD> 0.5 p. 100) and industries are interested by the fiber and  its low THC content. This chemotype grows in temperate climates and is native to France, Russia and Hungary. In ''fiber type'' chemotype, is possible to distinguish two other different chemotypes (I and II) which differ notably from each other by their THC level (I: THC> 0.1 p 100. ; II: THC <0.05 p 100).

Regardless of the stage of plant developpement, this distinction between the chemotypes is possible and has allowed to hemp industry to obtain many varieties of hemp with a low THC content10.
 
Photo credit : Wikipedia
Geographical origin 
Some studies report that the geographical origin has an influence on the chemical composition of C. sativa (L.) despite the monotypic genus of the plant14. Sometimes, the literature showed that the climate can also influenced the amount of cannabinoids in the plant. An english study was made on the culture environment of C. sativa (L.). This research showed that when the plant is grown in a hot environment, the content of cannabinol (CBN) would be higher, and when the plant is grown in a temperate climate (with a reduced number of light hours), the content of cannabidiol (CBD) would be higher than the content of Δ-9-tetrahydrocannabinol (THC)12. Moreover, when the plant is cultivated in a tropical and subtropical climates, an higher content of THC in Cannabis sativa (L.) was demonstrated12. Other studies have demonstrated that the C. sativa (L.) from Mexico and Turkish have not demonstrated a variation in their chemical profile when there were subjected to different environmental variations12.

Growing conditions

Apparently, the different kind of soils would are important factors in the amount of cannabinoids of C. sativa (L.). The environment and the geographical origin would be the more important factors and would act significatively on the composition of the plant12,14. However, many studies have been conducted on the growth condition of this plant and on the factors which is favored to the high production of fibers. Other studies reported that when C. sativa (L.) escapes from cultivated fields, the plant better grows in fertile soil, light and well drained soil than in other conditions15. Peat soils would increase the ratification of the branches unlike a rich soil in minerals12. Soils with a neutral pH would help to promote growth of this plant. Soil fertility also plays an important role in the physiology of the plant. The nitrogen content (N) would influence  the ratio of male / female of plants and allows to the plant stems to become more bigger, but offering a lower strength fiber12,16. By cons, a soil rich in phosphorus (P) and potassium (K) would increase the efficiency of the plant. The drought influences the quality of fibers by increasing the production, but  in decreasing the size of the fibers17.

Commercial potentials

Several studies showed that oil of C. sativa (L.) is economically interesting to use as biodiesel18,19,20. These studies have shown above that according to the time of harvest, the amount of biomass of the plant was higher, especially in the fall, and showed an interesting ratio of energy for the industry20. Other studies, have focused on the use of bark of C. sativa (L.) as a raw material for papermaking21. During the growing season of the plant, the cellulose compound increases and the lignin production decreases in the bark. These qualities are particularly useful to increase the strength of paper by the higher cellulose content. In addition, the quality of these long fibers which seem to be like those of resinous has been the subject of a study on the use of C. sativa (L.) as a raw material of pulp of paper22 and ''Kraft'' pulp23. Researches have been conducted on the use of Cannabis sativa (L.) and  with other plants for extracting heavy metals by phytoextraction process24 contaminated calcareous soils25. Several studies showed different ways to give a second life to biowaste textile and C. sativa (L.) would be a good candidate for this kind of recycling.

In summary

  •     There are three chemotypes defined in the literature according to the geographical origin of C. sativa (L.);

  •     The composition and the kind of soils influence  the chemical composition of this plant in many ways;

  •     In addition to its psychotropic properties, C. sativa (L.) has an interesting antiemetic      activity and well documented;
  • ·         The fibers of C. sativa (L.) demonstrates interesting qualities to the paper industry.
References 

(1)      Marie-Victorin. Flore Laurentienne; 3e ed.; Gaëtan Morin éditeur: Montréal, 2002.
(2)      Small, E.; Pocock, T.; Cavers, P. B. The Biology of Canadian Weeds . 119 . Cannabis Sativa L . 2003.
(3)      Appendino, G.; Gibbons, S.; Giana, A.; Pagani, A.; Grassi, G.; Stavri, M.; Smith, E.; Rahman, M. M. Antibacterial Cannabinoids from Cannabis Sativa: a Structure-activity Study. Journal of natural products 2008, 71, 1427–1430.
(4)      Weinstein, B.; Paris-sud, U. Mise En Évidence De Deux Types Chimiques Chez Le Cannabis Sativa Originaire d’Afrique Du Sud. Phytochemistry 1977, 474, 9–12.
(5)      Pacifico, D.; Miselli, F.; Micheler, M.; Carboni, A.; Ranalli, P.; Mandolino, G. Genetics and Marker-assisted Selection of the Chemotype in Cannabis Sativa L. Molecular Breeding 2006, 17, 257–268.
(6)      Gouvernement du Canada. Santé Canada http://www.hc-sc.gc.ca/dhp-mps/marihuana/info/index-fra.php.
(7)      Potter, D. J. A Review of the Cultivation and Processing of Cannabis (Cannabis Sativa L.) for Production of Prescription Medicines in the UK. Drug testing and analysis 2013, 6, 31–38.
(8)      Fischedick, J. T.; Hazekamp, A.; Erkelens, T.; Choi, Y. H.; Verpoorte, R. Metabolic Fingerprinting of Cannabis Sativa L., Cannabinoids and Terpenoids for Chemotaxonomic and Drug Standardization Purposes. Phytochemistry 2010, 71, 2058–2073.
(9)      Ross, S. a; ElSohly, M. a. The Volatile Oil Composition of Fresh and Air-dried Buds of Cannabis Sativa. Journal of natural products 1996, 59, 49–51.
(10)    Fournier, G. Les Chimiotypes Du Chanvre ( Cannabis Sativa L .).
(11)    Machado Rocha, F. C.; Stéfano, S. C.; De Cássia Haiek, R.; Rosa Oliveira, L. M. Q.; Da Silveira, D. X. Therapeutic Use of Cannabis Sativa on Chemotherapy-induced Nausea and Vomiting Among Cancer Patients: Systematic Review and Meta-analysis. European journal of cancer care 2008, 17, 431–443.
(12)    Coffman, C. B.; Gentner, W. A. (1975) Cannabinoid Profile and Elemental Uptake of Cannabis Sativa L. as Influenced by Soil Characteristics (AJ). 1971.
(13)    De Meijer, E. P. M.; Hammond, K. M.; Micheler, M. The Inheritance of Chemical Phenotype in Cannabis Sativa L. (III): Variation in Cannabichromene Proportion. Euphytica 2008, 165, 293–311.
(14)    Hemphill, J. K.; Turner, J. C.; Mahlberg, P. G. Cannabinoid Content of Individual Plant Organs from Different Geographical Straiks of Cannabis Sativa L. Journal of natural products 1980, 43, 112–122.
(15)    Stearn, W. T. The Botany and Chemistry of Cannabie : the Cannabis Plant Botanical Characteristics; Churchill, J., Ed.; C.R.B. Joy.; Londre, 1970; pp. 1–11.
(16)    Werf, H. M. G.; Berg, W. Nitrogen Fertilization and Sex Expression Affect Size Variability of Fibre Hemp (Cannabis Sativa L.). Oecologia 1995, 103, 462–470.
(17)    Amaducci, S.; Zatta, A.; Pelatti, F.; Venturi, G. Influence of Agronomic Factors on Yield and Quality of Hemp (Cannabis Sativa L.) Fibre and Implication for an Innovative Production System. Field Crops Research 2008, 107, 161–169.
(18)    Li, S.-Y.; Stuart, J. D.; Li, Y.; Parnas, R. S. The Feasibility of Converting Cannabis Sativa L. Oil into Biodiesel. Bioresource technology 2010, 101, 8457–8460.
(19)    Prade, T.; Finell, M.; Svensson, S.-E.; Mattsson, J. E. Effect of Harvest Date on Combustion Related Fuel Properties of Industrial Hemp (Cannabis Sativa L.). Fuel 2012, 102, 592–604.
(20)    Prade, T. Industrial Hemp ( Cannabis Sativa L .) – a High-Yielding Energy Crop; 2011.
(21)    Van der Werf, H. M. G.; Harsveld van der Veen, J. E.; Bouma, a. T. M.; Ten Cate, M. Quality of Hemp (Cannabis Sativa L.) Stems as a Raw Material for Paper. Industrial Crops and Products 1994, 2, 219–227.
(22)    Mathijssen, W. J. M.; Haverkort, J. The Potential of Hemp ( Cannabis Sativa L .) for Sustain- Able Fibre Production : a Crop Physiological Appraisal. 1996, 109–123.
(23)    Dutt, D.; Upadhyaya, J. S.; Tyagi, C. H.; Kumar, a.; Lal, M. Studies on Ipomea Carnea and Cannabis Sativa as an Alternative Pulp Blend for Softwood: An Optimization of Kraft Delignification Process. Industrial Crops and Products 2008, 28, 128–136.
(24)    Citterio, S.; Santagostino, A.; Fumagalli, P.; Prato, N.; Ranalli, P.; Sgorbati, S. Heavy Metal Tolerance and Accumulation of Cd , Cr and Ni by Cannabis Sativa L . 2003, 243–252.
(25)    Meers, E.; Ruttens, a; Hopgood, M.; Lesage, E.; Tack, F. M. G. Potential of Brassic Rapa, Cannabis Sativa, Helianthus Annuus and Zea Mays for Phytoextraction of Heavy Metals from Calcareous Dredged Sediment Derived Soils. Chemosphere 2005, 61, 561–572.

 

2 comments:

  1. Hi Laurie,

    Just a comment on the essential oil composition of cannabis plants (and in general) - 1% of those esters and ketones can make a big difference from a sensory standpoint! A mixture of limonene and myrcene is hardly going to be reminiscent of the highly distinct odor of cannabis.

    ReplyDelete
  2. Marijuana is the useful plant and should know its positive uses whose planting it for other purposes. , Marijuana plant contains useful things treatments and medical uses.

    ReplyDelete