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Файл:Ординатура / Хирургия / Библиотека им академика М.И. Перельмана / Книга_5648_Библиотеки_им_академика_М_И_Перельмана.pdf
262 Pharmaceutical Chemistry
MeO
O
MeO2C
OH
O
Azadirachtin
Me
O
HO
MeO
Me
O
O
OAc
Me
Me
Me
O
Nimbin
O
O OMe
Me
O
O
O
Me
MeMe
O
OAcO
Gedunin
O
O
O
O
Me Me
CO2Me
Me
O
O
O
Me
O
O
Nimbolide
Me
OH
HO
OH
O
Me
O
Me
O
Me
O
Me
O
OH
OH
Epicatechin Catechin
Me
COOH
O
Me
Me
OH
O
Me Me
HO
Me
OH
Me
O
O
OH
COOH
O
Me Me
Margolone Margolonone
HO
Me
MeOMe
OAc
Me
Me
Mahmoodin
OH
OH
HO
OH
Gallic acid
COOH
Me
Me
O
Isomargolonone
O
COOH
O
O
OH
HO
OHOH OH OH
O
OH
O O O
OH
O
HO
O
HO
O
OH
O
OH
HO
O
GIa
HO
Me
OH
HO
O
OH
O
HO
OH
O
HO
OH
OH
OH
O
O
O
HO
OH
OH
O
O
O
OH
O
OH
OH
O
O
HO
HO
O
HO
HO
HO
O
O
O
OH
OH OH
O O O
OH
O
O
HO
OH
O
O
HO
OH
O
OH
O
HO
HO
O
GIIa
OH
HO
OH
OH
O
O
HO
OH
O
O
OH
O
HO
OH
OH
O
O
O
OH
O
GIIIa
Fig. 11.3: Bioactive neem compounds
5. Nimbidin acts as H2 receptor blocker and thus acts as an antihistamine or an
antiulcer agent.
6. Nimbidin inhibits the growth of Tinea rubrum, thus acts in antifungal activity.
Medicinal importance of Curcumin, Neem, Vitamin C, Ranitidine, Ginger, Tulsi, Garlic and Ajwain 263
7. It is bactericidal and an antituberculosis agent by completely inhibiting
Mycobacterium tuberculosis, while sodium nimbidinate also shows diuretic activity
on dogs.
8. Nimbolide is also active against malaria by inhibiting the growth of P. falciparum.
9. Nimbolide is also active against bacterial infections due to S. aureus and S. coagulase.
10. Neem seed oil also shows antimalarial and antifungal activities because the oil
contains active compound Gedunin.
11. Azadirachtin is extracted from neem seeds. It is tetranortriterpenoid plant from
limonoid family. It can also be used as phagostimulant and antifeedant.
12. Azadirachtin is also known as anti-insecticidal because it is used for growth
inhibition, disruption of moulting and malformation in the larval.
13. Deoxygedunin or Mahmoodin is isolated from seed oil and possesses moderate
antibacterial activity against some strains of human pathogenic bacteria.
Condensed tannins from the bar contain gallic acid, (+) gallocatechin, (–) epicatechin,
(+) catechin and epigallocatechin, of which gallic acid, (–) epicatechin and catechin
are primarily responsible for inhibiting the generation of chemiluminescence by
activated human polymorphonuclear neutrophil (PMN), indicating that these
compounds inhibit oxidative burst of PMN during inflammation.
14. It is also active against some Staphylococcus, Klebsiella and Serratia species, because
neem stem bark produces tricyclic diterpenoids named margolone, isomargolonone and margolonone.
15. Fresh matured neem leaves show potent antifungal activity against Trichophyton
mentagrophytes because it produces sulphur containing components, viz., cyclic
trisulphide and tetrasulphide.
16. M. azadirachta bark also acts as anti-inflammatory on the carrageenin-induced
oedema in mice. It is due to the presence of GIIa & GIIIa polysaccharides in the bark.
17. It also shows antiulcer activity in stress induced gastric lesions, because of the active
phytosterol component extracted from the lipid part of neem fruits.
18. A recent study shows that neem compounds act as antifeedant as well as insectrepellent. Neem oil is also used as an organic bio-pesticide repellent against insects
such as beetles, mealworms, and aphids.
19. The National Institute of Health reported that the neem extracts are also helpful in
the treatment of AIDS because it kills AIDS virus.
20. Neem oil contains a steroid E-sitosterol which is used to treat men suffering from
enlarged prostate glands.
21. It also contains unsaturated fatty acids, viz., linoleic, linolenic, and oleic acids which
are used to prevent arterial sclerosis.
264 Pharmaceutical Chemistry
Table 11.1: Bioactive compounds of neem
S.No. Compound Name Source Biological Activity
1 Nimbidin Seed oil Antifungal, Diuretic, Anti-inflammatory, Antiarthritic,
2 Nimbolide Seed oil Antibacterial and Antimalerial
3 Nimbin Seed oil Spermicidal
4 Azadirachtin Seed oil Antimalerial
5 Sodium nimbidate Anti-inflammatory
6 Gedunin Seed oil Antimalerial, Antifungal
7 Mahmoodin Seed oil Antibacterial
8 Catechin, gallic acid and
(-) epicatechin
9 Margolone, margolonone
and isomargolonone
10 Cyclic trisulphide and cyclic
tetrasulphide
11 Polysaccharides Anti-inflammatory
12 Polysaccharides G1A, G1B Bark Antitumour
13 Polysaccharides G2A, G3A Bark Anti-inflammatory
Bark Immunomodulatory, Anti-inflammatory
Bark Antibacterial
Leaf Antifungal
Antibacterial, Antipyretic, Hypoglycaemic, Spermicidal,
Antigastric ulcer
Medicinal uses of neem plant
All parts of the neem such as bark, leaves, fruits, flowers, seeds oil and gum are used for
various medicinal purposes. Medicinal uses of various parts of the neem plant are listed in
Table 11.2 and Fig. 11.4.
Table 11.2: Medicinal uses of different parts of neem
S. No. Part Medicinal uses
1 Leaf Leprosy, skin ulcer, eye problem, intestinal worms and anorexia.
2 Bark Analgesic.
3 Flower Bile suppression, eliminate intestinal worms and phlegm.
4 Fruit Urinary disorder, diabetes, leprosy, intestinal worms, phlegm, open wounds,
5 Twig Relieves asthma and cough, tumour, diabetes, piles, obstinate urinary disorder,
6 Gum Ringworms, wounds, ulcers and scabies.
7 Seed pulp Leprosy and intestinal worms.
8 Oil Leprosy and intestinal worms.
9 Root, flower, leaf,
bark, fruit together
epistaxis, piles and eye problem.
intestinal worms and spermatorrhoea.
Blood morbidity, blood purifier, biliary afflictions, itching, skin ulcer, skin allergy,
burning sensation and leprosy.
Medicinal importance of Curcumin, Neem, Vitamin C, Ranitidine, Ginger, Tulsi, Garlic and Ajwain 265
Anti-arthritic
Periodontal disease
Anti-inammatory
Spermicidal
Afforestation
Antifungal
activity
Antibacterial
activity
Antimicrobial
activity
HIV replication
Antimalarial
activity
Corrosion inhibitor
Male antifertility
Diuretic
NEEM
activity
AIDS
Analgesic
Fig. 11.4: Medicinal uses of neem
Antioxidant
Antiviral
Antidiabetic
Immunomodulatory
Used as
diesel fuel
Treatment of
predontitis
Insect repellent
Antitumour
Anti-ulcer
activity
Chemotherapeutic
Cleanse the blood to
improve the Liver
Antipyretic
11.3 MEDICINAL VALUE OF VITAMIN C (ASCORBIC ACID)
Naturally occurring organic compound, ascorbic acid contains very
effective antioxidant properties. It works as a precursor in large
number of vital biochemical reactions leading to synthesis of several
biomolecules, e.g., amino acids, neurotransmitters, harmones, etc. It is
natural antihistamine sugar acid synthesized in plants and the liver of
many vertebrates. It is also known by other names, viz., L-ascorbic
acid, antisorbutic vitamin, 3-oxo-L-gulofuranolactone (enol form), L-xyloascorbic acid and
L-3-ketothreohexuronic acid lactone. It is an important metabolite for various metabolic
processes in most of the living organisms and also necessary for various physiological
functions in the humans and thus it is an essential nutrient. Vitamin C is a water-soluble
vitamin which has very important function in the collagen synthesis (protein). It also plays
a key role in the production and functioning in gums, bones and skin muscle binding
materials or scar tissues. It is also required in the production of certain hormones,
neurotransmitters, metabolism of some amino acids, detoxification (detoxify the toxic
substances from body and the blood and then kill the infections), and immunity booster
(helps in proper functioning of the liver). It also acts as an antioxidant by reacting with
histamines and peroxides, leads to reduction in the inflammatory symptoms which finally
lead to reduction in cancer infections.
Main sources of vitamin C are citrus fruits and juices, turnip greens, tomatoes, sweet
and white potatoes, mango, fruits, winter squash, vegetables, cauliflower, green peppers,
red peppers, leafy greens, strawberries, broccoli, watermelon, cantaloupe, papaya, cabbage,
HO
HO
L-Ascorbic acid
O
HO OH
O
266 Pharmaceutical Chemistry
brussels sprouts, raspberries, blueberries, cranberries, pineapples, etc. Almost all vitamin
supplements and most pharmaceutical preparations contain synthetic ascorbic acid
component.
Biosynthesis of Vitamin C (Fig. 11.5)
D-Glucose
2+
Pd
CHO
H OH
HO H
H OH
H OH
CH2OH
D-Glucose D-Glucuronic acid D-Gulonic acid
Lactonase Oxidase
2+
Ni
80-125 atm
140-150°C
2-Keto-L-gulonic acid
Oxidizing
enzyme
CH
OH
2
OHH
O
OH HO
H
H
g
−
L-Gulonolactone
Fig. 11.5: Biosynthesis of Vitamin C
Fermentation
D-Sorbitol
HCl
MeOH
Fig. 11.6: Reichstein process for the synthesis of L-ascorbic acid
CHO
H OH
HO H
H OH
H OH
COOH
O
H
L-Sorbose
2-Keto-L-gulonic acid methyl ester
Reducing
enzyme
Acetone
conc. H
CH
H OH
HO H
H OH
H OH
COOH
CH
OH
2
OHH
O
H
HO OH
L-Ascorbic acid
2SO4
EtOH
100°C
OH
2
O
Diacetone-L-sorbose
L-Ascorbic acid
Reichstein process is extensively used for the commercial synthesis of L-ascorbic acid
(approximately 50% yield) using D-glucose as a starting material (Fig. 11.6). This process
is high energy consuming reaction which requires high temperature and/or pressure for
all steps.
Common uses of vitamin C (Fig. 11.7)
1. Amino acid sequence procollagen is a precursor molecule to the protein collagen.
In this sequence, glycine is repeated at every third position and also contains a high
frequency of two amino acids (hydroxyproline and hydroxylysine which is actually
converted from proline and lysine) that is usually not found in any other proteins.
Ascorbic acid as a cofactor with enzyme prolyl hydroxylase used to catalyse the
synthesis of procollagen from the hydroxylation of proline and lysine.
2. It prevents and detoxifies the histamine release.
3. It acts as a good folic acid reductase enzyme protector. This enzyme is used in the
conversion of folic acid to folinic acid. It also helps to release free folic acid from its
food conjugates.
Medicinal importance of Curcumin, Neem, Vitamin C, Ranitidine, Ginger, Tulsi, Garlic and Ajwain 267
4. It enhances or facilitates iron absorption in the humans.
5. It is the most potent enhancer of non-heme iron absorption.
6. It is useful in lowering serum uric acid levels resulting in lower incidence of gout.
7. Ascorbic acid is very labile; it’s deficiency can cause of scurvy.
Hormone building
Neurotransmitter
building
Antifungal
activity
Antibacterial
activity
Antimicrobial
activity
Gall bladder disease
prevention
Antidiabetic
Antioxidant
VITAMIN C
Anti-asthmatic
Antiallergy
Fig. 11.7: Medicinal value of vitamin C
Anticancerous
Drug metabolism
Immune system
booster
Immunomodulatory
Collagen
production
Treatment of
blood pressure
Protecting agains
oxidative damage
Urinary
Hydroxyproline
Excretion
t
8. Vitamin C is a key component to boost immunity and thus prevents disease,
infections and aids in many body building processes. The advantages of vitamin C
are as follows:
(a) Allergy and asthma relief: It helps to clean the lung airways, bronchial
constriction and reduces lung infection and allergy.
(b) Cancer prevention: It acts as a strong antioxidant, thus helps in the reduction of
most types of cancers.
(c) Collagen production: It is known for the synthesis of collagen, a protein that
binds cells together and acts as a building block of many connective tissues in the
body, viz., skin, ligaments, corneas, cartilage, and other body tissues and
structures. Due to synthesis of protein it has a key role as healer of wounds and
injuries.
(d) Gall bladder disease prevention: It is reported that daily use of vitamin C
supplement by women may have 34% less probability of gallstones and gall
bladder disease.
(e) Diabetes control: It helps to improve metabolism, thus controls the sugar level
in the blood.
268 Pharmaceutical Chemistry
(f) Neurotransmitter and hormone building: It helps in the formation of neuro-
transmitters, viz., serotonin, dopamine and norepinephrine which are
responsible for the proper functioning of the CNS, are maintained and recovered.
Deficiency of neurotransmitters can lead to psychiatric illness in the patient. It
also helps in the production of adrenal hormones in the body.
(g) Immune system booster: It also helps in the production of white blood cells,
thus balance the immune system. HIV-positive individuals are highly prescribed
to protect their immune system.
9. High or excess use of vitamin C can have adverse effects, which includes diarrhoea
and other gastrointestinal disturbances, increased oxalate excretion and kidney
stone formation, increased uric acid excretion, pro-oxidant effects, systemic
conditioning (“rebound scurvy”), increased iron absorption leading to iron
overload, reduced Vitamin B12 and copper status, increased oxygen demand, and
erosion of dental enamel.
10. It may be used widely as cosmetic and additive.
11. Deficiency of vitamin C can cause scurvy, depression, hysteria, mouth dryness, dry
eyes, loosening of teeth, follicular hyperkeratosis, hair loss, swollen & inflammed
gums, and dry itchy skin.
11.4 MEDICINAL IMPORTANCE OF RANITIDINE
It is a pale yellow granular furan derivative containing
secondary and tertiary amino groups. Its trade name
is Zantac. Ranitidine generally comes under the drug
class, histamine H
-receptor which inhibits stomach
2
Me2N
O
S
O2NHC
N
H
NHMe
.HCl
acid production. Ranitidine tablets are recommended for the treatment of benign gastric
ulcer and duodenal ulcer. The pathogenesis of duodenal ulcer disease is usually associated
with the presence of Helicobacter pylori that is why ranitidine is always used in combination
with metronidazole and amoxycillin. Tablets of Ranitidine are also indicated for:
The treatment of benign gastric ulcer and duodenal ulcer are associated with
nonsteroidal anti-inflammatory agents.
Post-operative ulcer can be treated with ranitidine.
Some nonsteroidal anti-inflammatory agent, viz., aspirin must be avoided.
Chronic episodic dyspepsia can be treated with ranitidine.
Oesophageal reflux disease can be treated with ranitidine.
Ranitidine gives relief in gastro-oesophageal reflux disease.
Zollinger-Ellison syndrome can be treated with ranitidine.
It is also used for the treatment of hives with the combination of antihistamines.
It also acts as mild antibiotic when used with bismuth salt of citrate.
It also used to reduce the risk of aspiration pneumonia.
Medicinal importance of Curcumin, Neem, Vitamin C, Ranitidine, Ginger, Tulsi, Garlic and Ajwain 269
Ranitidine can be prescribed to reduce the gastric secretion and acid output when
individual has the following indications:
ʊ Prophylaxis of recurrent haemorrhage in individuals with bleeding peptic ulcers.
ʊ Stress ulceration can lead to prophylaxis of upper gastrointestinal haemorrhage.
Adverse Reactions
Ranitidine has adverse effects such as cardiac and acute renal failure and thus increases
their risk of death. Regular use of this may lead to weakening of H
-blockers and thus
2
reduces proper absorption of drugs that requires an acidic stomach. It is also responsible
for the increase in pneumonia. It can also have some other adverse reactions, viz., CNS,
cardiovascular, gastrointestinal, hepatic, musculoskeletal, hematologic, endocrine,
integumentary, and respiratory, other rare side effects include acute interstitial nephritis,
small elevated serum creatinine, hypersensitivity reactions (viz., fever, rash, bronchospasm,
eosinophilia), anaphylaxis, angioneurotic oedema, etc.
11.5 MEDICINAL IMPORTANCE OF GINGER (Zingiber officinale)
Naturally occurring medicinal herb ginger (Zingiber officinale)
belongs to the family Zingiberacae and is distributed worldwide.
Genus Zingiber derives from a
“horn-shaped,” with respect to the rhizome. It is consumed
worldwide as a spice
various medicinal properties.
for
and flavouring agent in food and is used
Ginger has been used to treat various
of Rigveda (3500 to 1800 B.C.) in India. Generally, it has been
used extensively as a spice in foods
for cold induced diseases, cough, nausea,
rheumatism, heart palpitation and
antiasthmatic by using 1-2 teaspoon of fresh ginger juice with honey. It is also used in
traditional
medicine as antipyrexia, antibronchitis, carminative, muscular pain, treatment
of rheumatism disorders, piles and gastrointestinal disorders.
Chemical compositions of ginger contain over 400 different medicinally important
compounds. The major constituents in ginger include carbohydrates (~60%), fat (~10%),
lipids (3–7%), fiber (5%), terpenes, and various phenolic compounds. A terpene component
(essential oil 1-4%) of ginger contains D-curcumene, zingiberene, E-sesqui-phellandrene,
E-bisabolene and D-Farnesene, whereas Phenolic compounds include major amount of
gingerol (23-25%) and shogaol (18–25%) and minor amount of paradols. Besides these,
amino acids, proteins (~10%), phytosterols, raw fiber, vitamins (viz., nicotinic acid, Vitamin
A and Vitamin C), various minerals (~6%, Zn , Fe, Mn, Cu, Ca, and P), ash and residual
moisture (~10%) are also present.
Sanskrit word which means
diseases since the time
worldwide. Fresh ginger or ginger juice specially used
loss of appetite, asthma, swellings, colic,
dyspepsia. It is used as cough suppressant and
270 Pharmaceutical Chemistry
Ginger contains many phytonutrients which include zingiberene and bisabolene with
aromatic order and shogaols and gingerols with pungent taste. Other compounds with
pungent taste include 4-gingerdiol, 6-gingerdiol, 8-gingerdiol, 10-gingerdiol, 6-gingerdione,
10-gingerdione, 6-paradol, 1-dehydrogingerdione and diarylheptanoids.
Other medicinal uses of ginger are listed below (Fig. 11.8, Fig. 11.9, Table 11.3):
1. Ginger acts as anti-inflammatory in case of arthritic conditions such as rheumatoid
arthritis, osteoarthritis, or muscular discomfort.
2. It acts as prostaglandin inhibitor and leukotriene biosynthesis inhibitor.
3. It can be used as a preventive agent for migraine headache with an oral administration
of 500–600 mg of ginger powder with water.
4. It also contains antioxidant, antihistamine characteristics.
5. Ginger shows antioxidant activity by preventing the damage of macromolecules
which are usually caused by the free radicals or oxidative stress.
6. It is very good enhancer of metabolism by stimulating the bile secretion. Thus
mechanistically, it helps to increase the bile secretion which is ultimately beneficial
in the degradation and excretion of gallstones.
7. Ginger (5 gm) with a fatty meal can act as platelet aggregation induced inhibitor by
adenosine diphosphate and epinephrine to a large extent. Ginger has been reported
to inhibit prostaglandin synthesis in vitro. It has been reported that dietary fat
content affects platelet aggregation by modifying prostaglandin metabolism.
Inhibiting the transformation of arachidonic acid to thromboxane and decreasing
the sensitivity of platelets to many aggregating agents may be possible with the
administration of ginger in a fatty diet.
8. Ginger derivatives may prevent the accumulation of toxic substances that ultimately
block the gastrointestinal reactions which cause nausea.
9. It is used to increase gastric motility.
10. Recent study postulated about ginger’s role in preventing the nausea feedback at
the nerve receptor level. In motion sickness, nausea and vomiting are mediated by
specific receptors in the central and peripheral nervous system. These receptors are
activated by the chemical messengers, acetylcholine and histamine. Ginger produces
antimotion sickness action, probably through anticholinergic and antihistaminic
effects.
11. It acts as antitumor through genetic pathway modulation, such as activation tumour
suppressor gene, modulation of apoptosis and inhibition of VEGF. Earlier study
has shown that terpenoids, constituents of ginger induce apoptosis in endometrial
cancer cells through the activation of p53.
12. Ginger constituents, viz., gingerol, zingerone, paradol and shogaols are potent
antimicrobial active components.
13. It has an anti-blood clotting ability which helps to reduce stroke and heart disease
similar to garlic and onion.
Medicinal importance of Curcumin, Neem, Vitamin C, Ranitidine, Ginger, Tulsi, Garlic and Ajwain 271
14. Fresh ginger juice is highly effective in various stomach disorders.
15. It is responsible for enhancing the immunity by promoting various biochemical
functions.
16. Ginger oil and eucalyptus oil in combination act as very effective remedy to increase
immunity as well as to improve breathing.
17. It can be used as a powerful antifungal agent by applying ginger oil, tea tree oil and
coconut oil together.
18. Ginger is useful to cure stomach ulcers.
19. The growth inhibition of cultured ovarian cancer cells are observed during the
treatment of ginger, thus it may act as anticancer agent.
20. Gingerols are the natural components used to enhance insulin sensitivity and
improve diabetes. It helps to reduce sorbitol accumulation in the human blood cells.
21. Ginger tea is specially used to relieve nausea, congestion, relax the body, and reduce
inflammation.
Fig. 11.8: Medicinal properties of ginger
22. Washing hair with hot water with ginger steeped is effective in treating baldness
and suppressing dandruff.
23. Ginger can detoxify the body against toxicities like snakebite and poisonous juice
from taros and wild herbs and fruits.