Transcript Benzylisoquinoline Alkaloids

Alkaloids and Quercetin
By
Dr. Gobinath Pandian
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Alkaloids
Alkaloids are a group of nitrogen-containing bases. Most
of them are drugs. Only a few (like caffeine) are derived
from purines or pyrimidines, while the large majority is
produced from amino acids.
Ornithine derivatives: Ornithine is a precursor of the
cyclic pyrrolidines that occur in the alkaloids of tobacco
(nicotine, nornicotine) and other Solanaceae. Nicotine is a
starting compound of numerous further tobacco alkaloids.
During the biosynthesis of tropane, intermediates are
produced that are at the same time starting compounds
for cocaine and hyoscamine.
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A cyclic organic compound that contains nitrogen in a
negative oxidation state and is of limited distribution
among living organisms. Over 10,000 alkaloids of
many different structural types are known;
And no other class of natural products possesses such
an enormous variety of structures. Therefore, alkaloids
are difficult to differentiate from other types of
organic nitrogen-containing compounds.
Types of Alkaloids
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Monoterpenoid Indole Alkaloids
Tropane and Nicotine Alkaloids
Benzylisoquinoline Alkaloids
Bisbenzylisoquinoline Alkaloids
Monoterpenoid Indole Alkaloids
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The monoterpenoid indole alkaloid pharmaceuticals that are still commercially isolated
from plant material are the antimalarial drug quinine from Curcuma officinalis, the
antineoplastic drug camptothecin from C. acuminata, the rat poison and homeopathic
drug strychnine from Strychnos nuxvomica, and the antineoplastic chemotherapeutic
agents vincristine and vinblastine from Catharanthus meus.
Tropane and Nicotine Alkaloids
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The tropane class of alkaloids, which are found mainly in the Solanaceae, contains the
anticholinergic drugs hyoscyamine (the racemate of which is called atropine) and
scopolamine. Solanaceous plants have been used traditionally for their medicinal,
hallucinogenic, and poisonous properties, which are due to their tropane alkaloids. The
narcotic topical anesthetic and central nervous system stimulant cocaine is a tropane
alkaloid found outside of the Solanaceae in Erythmxylon coca. It is a useful medicinal in
small, controlled doses is potentially lethal when abused.
Benzylisoquinoline Alkaloids
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The benzylisoquinoline alkaloids are avery large and diverse class of
alkaloids. This family contains such varied physiologically active members
as emetine (an antiamoebic), colchicine (a microtubule disrupter and gout
suppressant), berberine (an antimicrobial against eye and intestinal
infections), morphine (a narcotic analgesic), codeine (a narcotic analgesic
and antitussive), and sanguinarine (an antimicrobial used in oral hygeine).
Bisbenzylisoquinoline Alkaloids
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The bisbenzylisoquinoline class of alkaloids contains over 270 members, all
of which are dimers of tetra hydrobenzylisoquinolines connected by one
to three ether linkages formed by phenol coupling.
FUNCTIONS
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Digestive problem
Cardiovascular, Antiseptic, Anti-inflammatory.
Facial cream and Pain reliver
Anti microbial activity
In modern medicine, tubocurarine chloride is used as a
neuromuscular blocking agent to secure muscular relaxation in
surgical operations.
Extracts of bloodroot that are rich in the intensely red
benzophenanthridine alkaloid sanguinarine are currently added to
toothpastes and oral rinses.
Quercetin
In studies, quercetin is found to be the most active of the flavonoids, and many
medicinal plants owe much of their activity to their high quercetin content.
Quercetin and its sugar-bound, or glucosylated, forms represent 60-75% of
flavonoid intake (Bouktaib et al. 2002).
Quercetins may reduce inflammation associated with allergies, inhibit the
growth of head and neck cancers, and protect the lungs from the harmful
effects of pollutants and cigarette smoke.
Where Quercetin is Found
Apples, pears, cherries, grapes, onions, broccoli, leaf lettuce, garlic,
green tea, and red wine contain high amount of quercetins.
What are Quercetin glycosides?
Many flavonoids are bound to sugars in their natural state, the O-glycoside
form, where glycosylation can occur at any hydroxyl group to yield a sugar.
The most common quercetin glycosides have a sugar group
at the 3-poistion, such as quercetin-3-O-β-glucoside
It is these glycosylated structures that are most common in
nature, not the aglycone, or parent compound.
Quercetin concentration is highest in peel of Onion
& apples not in flesh
The Health benefits of Quercetin
Quercetin has demonstrated significant anti-inflammatory activity because of
direct inhibition of several initial processes of inflammation.
Quercetin can also reduce inflammation by scavenging free radicals
The anti-inflammatory action of quercetin is caused by the inhibition of enzymes,
such as lipoxygenase, and the inhibition of inflammatory mediators.
Studies have shown an improved lung function and lower risk of certain respiratory
diseases (asthma and bronchitis) for people with high apple (rich in quercetin)
intake
Quercetin mediates preferential degradation of oncogenic Ras and causes
autophagy in Ha-RAS-transformed human colon cells
The Onion: A Quercetin source
Onions (Allium cepa) belong to the lily family, the same family as garlic.
There are
over 600 species of Allium, distributed all over Europe, North America,
Northern Africa and Asia.
Onion and other Allium vegetables are characterized by their rich content of
thiosulfinates, sulfides, sulfoxides, and other odoriferous sulfur compounds.
The cysteine sulfoxides are primarily responsible for the onion flavor and produce
the eye-irritating compounds that induce lacrimation.
Nutritive Values of Onions : Per 100 gm.
1 Medium
Onion (148 g)
Onion Nutrition Facts
Percent Daily
Values*
Calories
45
Total Fat
0
0%
Cholesterol
0
0%
Sodium
5
0%
Total Carbohydrate
11g
4%
Dietary Fiber
3g
12%
Sugars
9g
Protein
1g
Vitamin A
0g
0%
Vitamin C
11.8mg
20%
Vitamin B6
0.01g
5%
Calcium
36.8mg
4%
Iron
0.6mg
4%
Folic Acid
15.2mcg
4%
Potassium
190mg
5%
Selenium
0.5mcg
1%
Zinc
0.2mg
1%
The Health benefits of Onion
Onions are a rich source of flavonoids, substances known to provide protection against
cardiovascular disease. Onions are also natural anticlotting agents since they possess
substances with fibrinolytic activity and can suppress platelet-clumping.
Studies in Greece have shown a high consumption of onions, garlic and other allium
herbs to be protective against stomach cancer.
Onion contain chemical compounds such as Quercetin which believed to have
anti-inflammatory, anticholesterol, anticancer, and antioxidant properties.
Onions may be especially beneficial for women, who are at increased risk for
osteoporosis by destroying osteoclasts so that they do not break down bone.
Onion is benenificial in the following diseases
1. Asthma
2. Influenza
3. Colds
4. Tuberculosis
5. Insomnia
6. Pneumonia
7. Antiallergy
8. Obesity
9. Reduce inflammation
10. Slightly laxative
11. High Blood Pressure
12. Lowers cholesterol
13. Fight against Cancer
14. Helps destroy worms and other parasites.
15. Diabetes mellitus - lowers blood sugar.
16. Valuable for the hair, nails of the fingers and toes, and for the eyes.
The Apple: A Quercetin source
“an apple a day will keep the doctor away”
Facts about apple fruit
Apples contain a variety of phytochemicals, including quercetin, catechin, and
chlorogenic acid, all of which are strong antioxidant.
linked the consumption of apples with reduced risk of some cancers,
cardiovascular disease, asthma, and diabetes
have very strong antioxidant activity, inhibit cancer cell proliferation, decrease
lipid oxidation, and lower cholesterol.
Health benefits of Apple eating
Antioxidants
Aging
Wrinkles
Hair Growth
Cholera
Chronic obstructive pulmonary
disease
Bladder Cancer
Lung Cancer
Prostate
Heart Disease
Assignments:
 Mark -10
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Role numbers: 1, 6, 11, 16, 21, 26, 31, 36.
Volatiles oils and compounds
Role Numbers: 2, 7, 12, 17, 22, 27, 32, 37.
Transgenic Techniques
Role numbers: 3, 8, 13, 18, 23, 28, 33, 38.
Cancer and Epigenetic
Role Numbers: 4, 9, 14, 19, 24, 29, 34.
Cardio Vascular Diseases
Role Numbers: 5, 10, 15, 20, 25, 30, 35.
Vegetable Oils and compounds
Thank You
Mid Term Exam: 20th October 10.30am to 12.00 noon.
Assignment Submission Date: November 17th
Happy Choo-seok