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PHARMACOGNOSY
3rdstage / 1sttrem
Carbohydrates
Dr. Rand Aqeel Alkhafaji
[email protected] Carbohydrates
Carbohydrates (CHO) are organic compounds (also called hydrated carbon)
or polyhydroxy aldehydes or polyhydroxy ketones.
containing carbon, hydrogen, and oxygen.
Carbohydrates are widely distributed in plants and animals; they have
important structural and metabolic roles.
In plants, glucose is synthesized from carbon dioxide and water by
photosynthesis.
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Importance of Carbohydrates
1. Act as a main source of energy and storage form of energy.
2. Can be structural components of many organisms :
Can be cell-membrane components mediating intercellular
communication.
Can be cell-surface antigens.
Can be associated with proteins and lipids.
Part of RNA, DNA, and several coenzymes (NAD+ , NADP+ , FAD, CoA).
Classification of Carbohydrates
1. Monosaccharides are those carbohydrates that cannot be hydrolyzed into
simpler carbohydrates i.e. it composed from one unit.
2. Disaccharides are condensation products of two monosaccharide units.
3. Oligosaccharides are condensation products of two to ten
monosaccharides. Example maltotriose (a trisaccharide of glucose).
4. Polysaccharides are condensation products of more than ten
monosaccharide units; example starches.
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Monosaccharides
Monosaccharides are those carbohydrates that cannot be hydrolyzed into
simpler carbohydrates.
They may be classified as:
trioses, tetroses, pentoses, hexoses, and heptoses, depending upon the
number of carbon atoms; and as aldoses or ketoses depending upon
whether they have an aldehyde or ketone group.
Hexoses are the most important monosaccharides found in plants. They are
the first detectable sugars synthesized by plants and form the units from
which most of the polysaccharides are constructed such as glucose, fructose
and galactose.
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Isomers
Compounds that have the same chemical formula but have different
structures are called isomers.
For example, fructose, glucose, mannose, and galactose are all isomers of
each other, having the same chemical formula, C6H12O6.
Cyclization of monosaccharides
Less than 1% of each of the monosaccharides with five or more carbons
exists in the open chain (acyclic) form. Rather, they are predominantly found
in a ring (cyclic) form, in which the aldehyde (or keto) group has reacted
with an alcohol group on the same sugar, making the carbonyl carbon
(carbon 1 for an aldose or carbon 2 for a ketose) asymmetric.
Monosachharides can exist in both cyclic structures i.e. either pyrano (six
membered ring) or furano (five membered ring).
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Cyclization creates an anomeric carbon (the former carbonyl carbon),
generating the α and β configurations of the sugar, for example,
α-Dglucopyranose and β- Dglucopryanose. These two sugars are both
glucose but are anomers of each other.
Reducing sugars
If the hydroxyl group on the anomeric carbon of a cyclized sugar is not
linked to another compound by a glycosidic bond, the ring can open.
The sugar can act as a reducing agent, and is termed a reducing sugar.
Joining of Monosaccharides
Monosaccharides can be joined to form disaccharides, oligosaccharides,
and polysaccharides. Important disaccharides include lactose (galactose +
glucose), sucrose (glucose + fructose), and maltose (glucose + glucose).
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Disaccharides
Those are compounds that can yield two monosaccharides molecules on
hydrolysis. There are three common disaccharides, sucrose, maltose and
lactose. All of which are isomers with the molecular formula C11H22O11.
Sucrose: It is the only disaccharide that occurs abundantly in free state in
plants.
Sucrose is used as sugar at home and occurs in fruit juices, sugar cane,
sugar beet, the sap of certain maples, and in many other plants.
Upon hydrolysis; sucrose yields equimolar quantities of glucose and fructose.
Sucrose is a non-reducing sugar.
Maltose: Maltose although seldomly occurring in the free state in nature, is
produced in large quantities by the hydrolysis of starch.
Upon hydrolysis, yields 2 molecules of glucose. It is a reducing sugar.
Lactose: Lactose possesses a free functional aldehyde group and is a reducing
sugar.
Commercially known as milk sugar. Bacteria cause fermentation of
lactose forming lactic acid. When these reactions occur, it changes the taste to a
sour one. It is a reducing sugar.
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Oligosaccharides are condensation products of two to ten
monosaccharides.
Example maltotriose (a trisaccharide of glucose).
Polysaccharides
Polysaccharides are formed from condensation products of more than
ten monosaccharide units. If only one type of monosaccharide unit is
present, the polysaccharide is a "homoglycan" but a "heteroglycan" if more
than one kind on monosaccharide is involved.
Examples of Homoglycans:
1- Starch: composed of glucose.
2- Inulin: composed of fructose.
3- Dextran: polyglucagon formed from sucrose.
4- Cellulose: consist of several hundred of D-glucose.
Examples of Heteroglycans
1. Gums: They are translucent, amorphous substances that are frequently
produced in higher plants as a protective after injury.
They are ingredients in dental and other adhesives and in bulk laxatives.
They are also useful as tablet binders, gelating agents, suspending agents,
stabilizers, and thickeners.
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2. Tragacanth: is the dried, gummy exudate from Astragalus gummifer.
Tragacanth is employed pharmaceutically as a suspending agent for insoluble
powders in mixtures, as an emulsifying agent for oils and resins, and as an
adhesive. It is employed in cosmetics (hand lotions) as a demulcent.
3. Acacia: Acacia is the dried, gummy exudate from the sterns and branches of
Acacia Senegal.
Acacia is used as a suspending agent. It possesses useful demulcent and
emollient properties and finds applications an adhesive and binder in
tablet granulations.
4. Agar: is the dried, hydrophilic, colloidal substance extracted from
Gelidium cartilagineum is used as a laxative, suspending agent, an emulsifier,
and as a tablet excipient and disintegrant.
5. Plantago seed (psyllium seed): is the cleaned, dried, ripe seed of
Plantago psyllium. Plantago seed is a cathartic.
6. Pectin: Pectin is a purified carbohydrate product obtained from the dilute
acid extract of the inner portion of the rind of citrus fruits or from apple.
Pectin is classified as a protectant and a suspending agent and is an ingredient
in many antidiarrheal formulations.
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Carbohydrate utilization
Storage carbohydrate such as the starch of plants or glycogen of animals is
made available for energy production by a process which involves conversion
of glucose to pyruvate by glycolysis and then the pyruvate converted to
acetylcoenzyme A, then will pass to the tricarboxylic acid cycle (TCA).
As a result of this, the energy rich carbohydrate is oxidized to CO2 and H2O.
Coenzymes in TCA will carry the liberated hydrogen atoms to the cytochrome
system in which the energy is liberated in stages, with the formation of ATP from
ADP.
The hydrogen combines with oxygen to form water.
Embden-Meyerhof scheme ( pathway) of glycolysis:
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Tricyclic acid cycle:
Pyruvate
The overall reaction for the metabolism of one molecule of glucose in terms
of ADP and ATP is:
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