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.
REFRENCES:
1. The
Botanical Garden Organization. Study report of Kancha-
Kanchong. Queen Sirikit
Botanical Garden, Chiang Mai. 2000.
2. Sachindra
N and Pradhan A. “Marijuana Drug Abuse Clinical and
Basic Aspects,” 1977. The C.V. Mosby
Company, Saint Louis. 1977; pp. 148-173.
3. Mechoulam
R and Gaoni Y. Recent advances in the chemistry of
hashish. Fortschr. Chem. Org. Naturst.
1967; 25, 175–213.
4. Meschler
JP and Howlett AC. Thujone
exhibits low affinity for cannabinoid receptors but
fails to evoke cannabimimetic responses. Pharmacol.
Biochem.
Behav.
1999; 62,473–480.
5. Russo E. Hemp for headache:
an in-depth historical and scientific review of Cannabis in migraine
treatment. J. Cann. Ther. 2001; 1, 21–92.
6. McPartland
JM and Russo EB Cannabis and Cannabis extracts: greater than the
sum of their parts? J. Cann. Therap. 2001; 1, 103–132.
7. McPartland,
J. and Mediavilla, V. Noncannabinoid
components, in Cannabis and Cannabinoids—Pharmacology,
Toxicology, and Therapeutic Potential (Grotenhermen,
F., and Russo, E., Eds.), Haworth Press, New York. 2002; pp. 401–409.
8. Vanhoenacker G,
Van Rompaey P, De Keukeleire
D and Sandra P. Chemo-taxonomic features associated with flavonoids
of cannabinoid-free Cannabis (Cannabis sativa subsp. sativa
L.) in relation to hops (Humulus lupulus L.). Nat. Prod. Lett. 2002; 16, 57–63.
9. Barrett ML, Gordon D and
Evans FJ. Isolation from Cannabis sativa
L. of cannflavin—a novel inhibitor of
prostaglandin production. Biochem. Pharmacol. 1985; 34, 2019–2024. Anxiolytic
natural and synthetic flavonoid ligands of the
central benzodiazepine receptor have no effect on memory tasks in rats. Pharmacol.
Biochem.
Behav.
1997; 58, 887–891.
11. Leson
G, Pless P, Grotenhermen F,
Kalant H and ElSohly MA. Evaluating the impact of hemp food consumption on workplace drug
tests. J. Anal. Toxicol. 2001; 25, 691–698.
12. Ross, S., ElSohly,
H., ElKashoury, E., and ElSohly,
M. Fatty acids of Cannabis seeds. Phytochem. Anal. 1996; 7, 279–283.
13. Hendriks H, Malingré TM, Batterman S and Bos R. Alkanes of the essential oil of Cannabis sativa. Phytochemistry 1977; 16, 719–721.
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