Phytochemistry
[PPC303]
Dr. Marwa Saeed Galaa
Goda | PhD
Lecturer of Pharmacognosy,
Faculty of Pharmacy, GU
[email protected] Course Desciption
The course is constructed to give insights on the
chemistry of the different classes of natural products such as
alkaloids, glycosides, volatile oils, carbohydrates, bitter
principles, resins and tannins. It covers the isolation
methods, tests for their chemical identification, bioassay-
guided isolation based on their biological activity, and their
toxicity or safety profile. Finally, the course concludes the
potential of natural metabolites in the market.
Total marks
Items Marks
1. Midterm exam 10 marks
Two Quizzes (8/3 & 26/4) (2. Course 10 marks
Student presentation work) 10 marks
3. Practical 30 marks
4. Final exam 40 marks
Total marks 100 marks
Syllabus
Week Lecture
1st week: 8/2/2025 Advising & registration
nd
2 week: 15/2/2025 Carbohydrates
3rd week: 22/2/2025 Bitter principles
4th week: 1/3/2025 Alkaloids: Introduction ( Ramadan)
5th week: 8/3/2025 Alkaloids: Examples 1 – [Quiz 1: carbohydrates & bitters]
Day: Saturday
6th week: 15/3/2025 Alkaloids: Examples 2
7th week: 22/3/2025 Resins and tannins
8th week: 29/3/2025 Official Holiday: Eid Al-Fitr
9th week: 5/4/2025 Midterm Exam (Online: Glycosides: Introduction)
10th week: 12/4/2025 Glycosides: Examples 1
11th week: 19/4/2025 Glycosides: Examples 2
12th week: 26/4/2025 Volatile oils: Introduction – [Quiz 2: Glycosides]
13th week: 3/5/2025 Volatile oils: Examples 1
14th week: 10/5/2025 Volatile oils: Examples 2
15th week: 17/4/2025 Final Exam
5
Learning Outcomes (LOs)
D1-1-1-1.a. Identify the different classes of naturally occurring carbohydrates,
alkaloids, volatile oils, bitters, resins, and glycosides.
D1-1-1-1.b. Describe the different methods used in the purification/ preparation of
natural medicinal agents, qualitative and quantitative determination in herbal
Domain 1: preparation.
Fundamental D1-1-1-1c. Relate the chemical structure of natural products with pharmacological
knowledge activity.
D1-1-1-1.d. Report their clinical uses and any contraindications as well as safety profile
of herbal preparations
D1-1-1-1.e. Recognize the available drugs containing natural products in the
pharmaceutical market.
D2-2-3-1.a. Conduct experimental tests to identify different classes of phytomedicinal
Domain 2: agents.
Professional and D2-2-3-1.b. Perform different procedures and protocols for isolation, qualitative and
ethical practice quantitative determination of different classes of natural products.
Domain 4: D4-4-1-1.a. Develop team-working ability through group projects.
Personal D4-4-1-1.b. Demonstrate time-management and presentation skills.
practice D4-4-2-2.a. Use computer technology to get relevant information.
Carbohydrates
- Definition of carbohydrates
- Classification
Definition of Carbohydrates
• They are also called saccharides, which means
sugars.
• Carbo-hydrates means hydrates of carbon
with chemical formula of Cx(H2O)y.
• Polyhydroxy aldehydes or ketones, or
substances that hydrolyze to yield polyhydroxy
aldehydes or ketones.
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Carbohydrates
- Definition of carbohydrates
- Classification
Classification of Carbohydrates
Carbohydrates
Monosacchaides Oligosaccharides Polysaccharides
[1 sugar unit] [2-10 sugar units] [>10 sugar units]
• They cannot be hydrolyzed • They are subclassified into di-, tri- • Polysaccharides are large molecules
into simpler carbohydrates. and tetrasaccharides, etc. linked containing 10 or more
(CnH2nOn). through glycosidic linkages. monosaccharide units.
• The carbonyl group of either • They are soluble in water, they are • Carbohydrate units are connected in
too large to pass through the cell one continuous straight chain or
an aldehyde (aldoses) or a
membrane. branched chain. Ex. starch 11
ketone (ketoses)
I. Monosaccharides
» Biologically important hexoses
[aldoses or ketoses]
Glucose / blood sugar / grape sugar: Fructose / fruit sugar / levulose:
IV injection, Diuretic food for diabetic (no need for insulin)
& for infant feeding formula
12
I. Monosaccharides
» Derivatives of hexoses
1- Sugar alcohols: like Sorbitol (mild laxative, oral or rectal enema)
and Mannitol (osmotic diuretic as it is freely filtered through the renal
tubules. However, as it is not reabsorbed, it continues to be osmotically
active in the tubules). Mannitol IV injection is used for measuring renal
filtration rate.
13
I. Monosaccharides
» Derivatives of hexoses
2- Sugar acids: Gluconic acid and its salts. Ca, Mg, or
ferrous gluconate is used (by IV or orally) for treatment
of mineral deficiency such as calcium deficiency, iron
deficiency or magnesium deficiency.
14
I. Monosaccharides
» Derivatives of hexoses
3- Lactones: Ascorbic acid (vitamin C): In plants, glucose or
galactose can be converted into ascorbic acid which is used as
immunostimulant, antioxidant and to prevent deficiency of
vitamin C (scurvy).
15
I. Monosaccharides
» Derivatives of hexoses
4- Amino sugar (glucosamine): It is derived from monosaccharides
by replacement of a hydroxyl group by an amino group. Glucosamine
sulphate is used for regeneration of cartilage in joint injuries and
arthritis.
16
Classification of Carbohydrates
Carbohydrates
Monosacchaides Oligosaccharides Polysaccharides
[1 sugar unit] [>10 sugar units]
[2-10 sugar units]
• They are subclassified into di-, tri-
and tetrasaccharides, etc. linked
through glycosidic linkages.
• They are soluble in water, they are
too large to pass through the cell
membrane. 17
II. Oligosaccharides
A. Disaccharides: On hydrolysis they yield 2
monosaccharides (similar or dissimilar). There are two
types, reducing (Maltose & Lactose) or non-reducing
(Sucrose).
B. Trisaccharides: On hydrolysis they yield 3
monosaccharides (Raffinose).
C. Tetrasaccharides: On hydrolysis they yield 4
monosaccharides (Acarbose).
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II. Oligosaccharides
Reducing and non-reducing disaccharides:
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II. Oligosaccharides
A. Non-reducing disaccharides:
e.g., Sucrose (cane sugar),
It doesn’t reduce Fehling’s solution and has a sweetening power more than glucose.
Uses: 1- In syrup preparation and tablet manufacture.
2- In high concentrations as bacteriostatic (jams).
3- In preparation of dextran (a polysaccharide used as plasma substitute).
e.g., Sucralfate; a semisynthetic sucrose derivative.
Aluminum sucralfate, an aluminum salt of sucrose
ocatasulfate, is a medication used to treat stomach
ulcers (protective barrier), gastroesophageal reflux
(Al(OH)3 neutralize HCl) disease. 20
II. Oligosaccharides
B. Reducing disaccharides:
Emulsin enzyme
e.g., Lactose (milk sugar).
Uses: Nutrient in infant foods (Less
sweet than sucrose and more easily
digested).
e.g., Lactulose: Semisynthetic disaccharide prepared from
lactose [galactose linked β 1→4 to fructose].
Uses: 1- laxative [It is not absorbed from gastrointestinal tract, so it is
safe for diabetic patients].
2- Hepatic encyphalopathy (it promotes uptake of ammonia by colonic
bacteria as a nitrogen source for protein synthesis). 21
II. Oligosaccharides
C. Trisaccharides
e.g., Raffinose is a non-reducing trisaccharide (glucose, fructose and
galactose). is found in beans, broccoli and soybeans. It is poorly
digested in stomach and intestine, so these foods tend to cause more
gas and flatulence because the raffinose is digested by bacteria once it
reaches the colon.
D. Tetrasaccharides
e.g., Acarbose is a tetrasaccharides anti-diabetic drug
used to treat type II diabetes by inhibition of alpha
glucosidase, enzyme needed to digest carbohydrates.
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II. Oligosaccharides
E. Cyclodextrins
• Cyclodextrins are crystalline substances obtained from partial
hydrolysis of starch by the action of specific enzymes. They are
composed of 5 or more α-D-glucopyranoside units
• N.B. They are arranged in cylindrical macro-rings with a
hydrophobic central cavity (central core) and a hydrophilic
outer surface.
• Uses: They are used as “drug enclosures” in order to:
1. Enhance drug solubilization (as meloxicam in Mobitil®),
2. Mask unpleasant taste (as Cetrizine in Zyrtec®), and
3. Reduce side effects (as indomethacin in Indocid®). 23
Classification of Carbohydrates
Carbohydrates
Monosacchaides Oligosaccharides Polysaccharides
[1 sugar unit] [2-10 sugar units]
[>10 sugar units]
• Polysaccharides are large molecules
containing 10 or more
monosaccharide units.
• Carbohydrate units are connected in
one continuous straight chain or
branched chain. Ex. starch 25
III. Polysaccharides
They can be differentiated according to their biological activity into:
1. Immuno-stimulant polysaccharides:
Echinacea polysaccharides [Immulant®] Immunostimulant and antiviral
polysaccharide that stimulates of phagocytic activity and uptake of foreign particles.
2. Hypoglycemic and laxative polysaccharides:
Fenugreek seed mucilage and molokhia leaf polysaccharide help in lowering blood
glucose level by slowing down digestion and absorption of carbohydrates.
3. Natural sweeting agents:
Sugars e.g., sucrose, glucose, fructose and honey.
or Sugar alcohols e.g., sorbitol and mannitol.
26
III. Polysaccharides
They can be differentiated according to their Function into:
1. Storage polysaccharides contain only α- glucose units. Ex. starch and glycogen.
2. Structural polysaccharides: Ex. cellulose (β- glucose), chitin (N-acetyl glucosamine) and
pectin (heterosaccharides).
They can be differentiated according to their Chemistry into:
1. Homosaccharides yield on hydrolysis similar simple sugar units. Ex. glucosans [e.g.,
Starch (α-Glucosan), Glycogen (α-Glucosan), Cellulose (β-Glucosan), Dextran (α-
Glucosan)], Fructosans [e.g., inulin], or homopolymer of amino sugar [e.g., chitin).
2. Heterosaccharides : yield upon hydrolysis dissimilar sugar units or yield on hydrolysis
monosaccharides in addition to other components such as uronic acids, or amino
sugars. Ex. Heparin, hyaluronic acid, mucilage, and pectin. 27
III. Polysaccharides
A. Homosaccharides
1. Dextran: a biopolymer of α-glucose produced by enzymes of
certain bacteria
(an example of biochemical conversion of a sucrose disaccharide
into a polysaccharide by the action of certain bacteria).
Uses
1- It is used as colloid plasma expander for emergency treatment
in cases of shock
due to hemorrhage, trauma or severe burns.
2- Dextran sulphates is used as anticoagulants through direct
thrombin inhibition. 28
III. Polysaccharides
A. Homosaccharides
2. Inulin: It is a linear chain fructosan. It is used as diagnostic agent for evaluation
of renal function (for measuring glomerular filtration rate).
3. Chitin and Chitosan: Chitin makes up the exoskeleton of insects and shrimps, and cell
walls of some fungi. It is made up of N-acetyl glucosamine containing β (1→4) glycosidic
bonds, while chitosan is a deacetylated chitin product
-Chitin is used as surgical thread that biodegrades as a wound heals.
-Chitosan is used to treat obesity and high cholesterol
-They are hydrating agent.
29
III. Polysaccharides
B. Heterosaccharides
• Heterosaccharides can be differentiated into:
- Polyuronides: hemicelluloses, gums, mucilages and pectic substances.
- Mucopolysaccharides (uronic acid + amino sugar): heparin, and hyaluronic acid.
1. Pectic substances: colloidal polyuronides of high molecular weight
like pectin & protopectin. They are used for treatment of diarrhea for
neonates
2. Mucilage are normal products of metabolism formed within the cell.
EX. Plantago mucilage and seaweed mucilage.
30
III. Polysaccharides
B. Heterosaccharides
Plantago mucilage Seaweed mucilage
Ex. Psyllium seed • Sodium alginate is obtained from brown
algae.
• Agarose obtained from red algae.
Uses
1- Bulk laxative 1-Sod. Alginate is antacid.
2-Immunostimulant 2- Agarose is used in treatment of jaundice
effect.
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III. Polysaccharides
B. Heterosaccharides
3. Heparin: is a highly sulfated mucopolysaccharide which is
commercially available from bovine lung and porcine
gastrointestinal mucosa. It is used as anticoagulant (It prevents
clotting in the bloodstream through thrombin inhibition)
Enoxaparin (Clexane®) is an effective alternative to heparin. It is made by chemically
breaking up the larger heparin chains into smaller fragments (low molecular weight
heparin). Heparin is stronger than enoxaparin but enoxaparin is longer-lasting.
Enoxaparin has an advantage over heparin because of its bioavailability as 90% of the drug is
available when given in the subcutaneous form. It can also be administered intravenously. 32
III. Polysaccharides
B. Heterosaccharides
4- Hyaluronic acid: [sulfate free]
• Present in Synovial fluid of joints, connective tissues and cartilage.
• It acts as lubricant and a shock absorbent in the joints. Also, it
enhanced fibroblasts to synthesize collagen and elastic fibers
protecting the skin from aging features and speeding up wound
healing.
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Phytochemistry
● Bitter principles.
Thank You
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