Phytochemical aspect of Cannabis sativa (L.)

 

Namrta Choudhary*, M.B. Siddiqui , Shazia, K.M. Abdul Raoof

Department of Botany, Aligarh Muslim University, Aligarh, India

*Corresponding Author Email: choudharynamrta@gmail.com      

 

ABSTRACT:

Cannabis  sativa  L. is dioecious, an aromatic  annual  flowering herb with height  ranging  from  1  to  5  meter  family Cannabiaceae. This paper presents a review on chemical composition of C.sativa. C.sativa contains various chemical constituents such as terpenoids, flavonoids, carbohydrates, fatty acids, hydrocarbon and various other chemical compounds which responsible for treating diverse diseases such as treating  migraine, epilepsy,  malaria,  glaucoma,  nausea  from  chemotherapy,  for  improving  appetite  in  patients  with  cancer,  AIDS,  and anorexia nervosa and for suppressing muscular spasms in multiple sclerosis etc.

 

KEY WORDS: Cannabis sativa , phytochemistry, cannabinoids, non-cannabinoids.

 

 


INTRODUCTION:

ORIGIN AND DISTRIBUTION:

It was originally distributed from the Caspian and the black sea area, and was taken from Persia and India eight centuries ago. It is widely cultivated throughout the temperate regions from Europe to North America more than tropical Asia 1.

 

FAMILY:

It belongs to an extremely small family Cannabiaceae (Urticaceae) of the order Urticales containing two genera Humulus and Cannabis.

 

COMMONLY KNOWN AS:

It is called Marijuana in America; Bhang, Ganja and Charas in India; Kif in North Africa; Dogga in South Africa; Krori in Tunisia, Habak in Turkey; Hashish in Middle East; Djomba or Liamba in Central Africa and Brazil; Sodom, Tampl, Gum, Gauge and stuff in Kinshasa, Swala and Whiskt in Ghana; Grifa in Mexico and Macohna in some parts of South America 2

 

GENUS:

The genus Cannabis contains only one spp. called Cannabis sativa L.

 

PHYTOCHEMISTRY OF CANNABIS SATIVA:

The Cannabis plant and its products consist of an enormous variety of chemicals. Some of the 483 compounds identified are unique to Cannabis, for example, the more than 60 cannabinoids (10 subclasses : [Cannabigerol(CBG), Cannabichromene (CBC), Cannabidiol (CBD),'9-Tetrahydrocannabinol (THC), '8-THC, Cannabicyclol (CBL), Cannabielsoin (CBE), Cannabinol (CBN) and Cannabinodiol (CBND) , Cannabitriol (CBT), Miscellaneous types] whereas the terpenes, with about 140 members forming the most abundant class, are widespread in the plant kingdom. The term “cannabinoids” represents a group of C21 terpenophenolic compounds found until now uniquely in Cannabis sativa L.3

 

TERPENOIDS:

The typical scent of Cannabis results from about 140 different terpenoids. Iso-prene units (C5H8) form monoterpenoids (C10 skeleton), sesquiterpenoids (C15), diterpenoids (C20), and triterpenoids (C30). Terpenoids may be acyclic, monocyclic, or polycyclic hydrocarbons with substitution patterns including alcohols, ethers, aldehydes, ketones, and esters. The essential oil (volatile oil) can easily be obtained by steam distillation or vaporization. It has been suggested that the terpenoid constituents of Cannabis modulate THC activity, for example, by binding to cannabinoid receptors, modulating the THC receptor affinity, or altering its pharmacokinetics e.g., by changing the blood–brain barrier 4. Whereas the anti-inflammatory and antibiotic activity of Cannabis terpenoids is known and has been used therapeutically for a long time, the serotonergic effect at 5-HT1A and 5-HT2A receptors of the essential oil, which could explain Cannabis-mediated analgesia and mood alteration, has only recently been demonstrated 5. E-Myrcene, the most abundant monoterpene in Cannabis, has analgesic, anti-inflammatory, antibiotic, and antimutagenic properties. E-Caryophyllene, the most common sesquiterpene, exhibits anti-inflammatory, cytoprotective (gastric mucosa), and antimalarial activity. The pharmacological effects of other Cannabis terpenes are discussed by 6.

 

FLAVONOIDS:

Twenty-three commonly occurring flavonoids have been identified in Cannabis, existing mainly as C-/O- and O-glycosides of the flavon- and flavonol-type aglycones apigenin, luteolin, quercetin, and kaempferol 7. Orientin, vitexin, luteolin-7-O-glucoside, and apigenin-7-O-glucoside were the major flavonoid glycosides present in low-THC Cannabis cultivars 8. The cannflavins A and B are unique to Cannabis 9. Apigenin, a flavonoid found in nearly all vascular plants, exerts a wide range of biological effects, including many properties shared by terpenoids and cannabinoids. It selectively binds with high affinity to benzodiazepine receptors, thus explaining its anxiolytic activity 10. The pharmacology of other Cannabis flavonoids is reviewed in 5 .Twelve simple amines, including piperidine, hardening, methylamine, ethylamine, and pyrrolidine, are known. The three proteins detected are edestin, zeatin, and zeatinnucleoside; the six enzymes are edestinase, glucosidase , polyphenoloxydase, peptidase, peroxidase, and adenosine-5-phosphatase.

 

CARBOHYDRATES:

Common sugars are the predominant constituents of this class. Thirteen monosacharides (fructose, galactose, arabinose, glucose, mannose, rhamnose, etc.) two disaccharides (sucrose, maltose), and five polysaccharides (raffinose, cellulose,hemicellulose, pectin, xylan) have been identified so far .In addition, 12 sugar alcohols and cyclitols (mannitol, sorbitol, glycerol, inositol, quebrachitol, etc.) and two amino sugars (galactosamine, glucosamine) were found.

 

FATTY ACIDS:

A total of 33 different fatty acids, mainly unsaturated fatty acids, have been identified in the oil of Cannabis seeds. Linoleic acid (53–60% of total fatty acids), D-linolenic acid (15–25%), and oleic acid (8.5–16%) are most common11 other unsaturated fatty acids are γ -linolenic acid (1–4%), stearidonic acid (0.4–2%), eicosanoic acid (<0.5%), cis-vaccenic acid, and isolinolenic acid. The saturated fatty acids are palmitic acid (6–9%), stearic acid (2–3.5%), arachidic acid (1–3%), behenic acid (<0.3%),

myristic acid, lignoceric acid, caproic acid, heptanoic acid, caprylic acid, pelargonic acid, capric acid, lauric acid, margaric acid, and isoarachidic acid. The fatty acid spectrum of Cannabis seeds does not significantly vary in oil produced from the drug (THC) or low-THC (hemp, fiber) type Cannabis 12. For the THC content of Cannabis seeds and seed oil.

 

HYDROCARBONS:

The 50 known hydrocarbons detected in Cannabis consist of n-alkanes ranging from C9 to C39, 2-methyl-, 3-methyl-, and some dimethyl alkanes 13 .The major alkane present in an essential oil obtained by extraction and steam distillation was the n-C29 alkane nonacosane (55.8 and 10.7%, respectively). Other abundant alkanes were heptacosane, 2, 6-dimethyltetradecane, pentacosane, hexacosane,and hentriacontane.

 

SIMPLE ALCOHOLS, ALDEHYDES, KETONES, ACIDS, ESTERS, AND LACTONES:

 Seven alcohols (e.g., methanol, ethanol, 1-octene-3-ol), 12 aldehydes (e.g.,acetaldehyde, isobutyraldehyde, pentanal), 13 ketones (e.g., acetone, heptanone-2, 2-methyl-2-heptene-6-one), and 21 acids (e.g., arabinic acid, azealic acid, gluconic acid) have been identified.

 

OTHERS:

Among the 11 phytosterols known are campesterol, ergosterol, E-sitosterol, and stigmasterol. Vitamin K is the only vitamin found in Cannabis, whereas carotene and xanthophylls are reported pigments. Eighteen elements were detected (e.g., Na, K, Ca, Mg, Fe, Cu, Mn, Zn, and Hg).

 

Table: 1. LIST OF  PHYTOCHEMICALS PRESENT IN CANNABIS SATIVA

Total compound

(483 approx.)

Terpenoids

(>120)

Cannabinoids

(>70)

Hydrocarbons (50)

Sugars and Related Compounds(34)

Nitrogenous Compounds(27)

Non-cannabinoids Phenols(34)

Flavonoids

(23)

Fatty acids(22)

Simple acids(21)

Amino acids (18)

Steroids

(11)

Simple Ketones(13)

 

Simple esters and Lactones(13)

Simple Aldehydes(12)

Simple Alcohols

(7)

Proteins, Glycoproteins and Enzymes(11)

Elements

18(e.g., Na, K, Ca,Mg, Fe, Cu, Mn, Zn, Hg)

Pigments

 2

(carotene and Xanthophylls)

Vitamins

1

(only k)

Note: Parenthesis representing quantity of phytochemicals


 

 


Table: 2. NON CANNNABINOID (FLAVONOID, PHENOL) C- AND O-GLYCOSIDES FORMING FLAVONOID AGLYCONES AND C-GLYCOSIDES AND CANNABINOIDS OF CANNABIS SATIVA L.

 

 


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Received on 04.12.2013                                   Accepted on 02.02.2013        

Modified on 21.01.2013                         ©A&V Publications all right reserved

Research J. Science and Tech 5(2): April- June, 2013 page 284-288