SlideShare ist ein Scribd-Unternehmen logo
1 von 131
Major Medicinally Important 1o and 2o
Metabolites
1
Carbohydrates
2
Session outline
• Introduction
• Classification
• Relations among different carbohydrates
• Sugars
• Polysaccharides
• Compounds related to sugars
• Qualitative tests for carbohydrates
3
Four Major Types of Biological Macromolecules
Type of Polymer Monomers making up
Polymer Example
I. Carbohydrates
(Polysaccharides) Monosaccharides Sugars, Starch,
Cellulose
II. Lipids Fatty acids and glycerol Fats, steroids,
cholesterol
III. Proteins Amino acids
Enzymes,
structural
components
IV. Nucleic Acids Nucleotides DNA, RNA
Introduction
Introduction
Definition
– carbohydrate(hydrated carbon)
– Is a polyhydroxy aldehyde or ketone or a larger
molecule which can be hydrolyzed to a polyhydroxy
aldehyde or ketone or their derivatives
5
Introduction…
– Are the most abundant compounds found in plant
(cellulose, starch, sugars) and animals (glycogen)
– In most cases, composed of only C, H and O , with
general formula of (CH2O)n
– Usually the ratio of H to O is 2:1
6
Introduction…
However there are exceptions for this rule
 There are compounds that conform to the hydrate
rule (2:1 ratio of H and O) but not carbohydrates
E.g. Formaldehyde, HCHO; Acetic acid, CH3COOH
7
Introduction…
 There are compounds that do not conform to the
hydrate rule but have chemical properties of
carbohydrates
E.g. Deoxy sugars like:Rhamnose(C6H12O5),
digitoxose(C6H12O4)
8
Introduction…
Why do we study carbohydrates in pharmacognosy?
• Widely used in pharmaceuticals as additives
(suspending agents, emulsifiers, fillers, binders,
absorbents/ adsorbents)
• Starting material in the synthesis of various
compounds
9
Introduction…
• Many of them have pharmacological activity
– Anticoagulant
– Hypoglycemic activity
– Anti-inflammatory activity
– Antimicrobial
10
Role in living organism
• Storage of energy (e.g., starch and glycogen)
• Structural components (e.g., cellulose in plants and
chitin in arthropods)
• The 5-carbon monosaccharide ribose is an important
component of coenzymes (e.g., ATP ) and the
backbone of the genetic molecule known as RNA.
11
Introduction…
12
Sources
• Major sources of carbohydrates are plants
• E.g Glucose is produced in plants through photosynthesis
from CO2 and H2O
• Glucose is converted in plants to other small sugars and
polymers (cellulose, starch)
Introduction…
13
Classification of Carbohydrates
I. Number of carbohydrate units
• Monosaccharides
• Oligosaccharides
• Polysaccharides
14
II. Position of carbonyl group
aldose: Sugars that contain an aldehyde group
ketose: Sugars that contain a ketone group
An aldose: Glucose
III. Cyclic form
• Less then 1% of CHO exist in an open chain form
• Pyranose (6-membered ring) and furanose (5-membere)
from
http://ntri.tamuk.edu/cell/carbohydrates.html
A ketose: Fructose
Classification…
17
18
IV. Number of carbons
Classification…
• Monosaccharides or simple sugars
– They contain one sugar units
– They cannot be hydrolyzed further
• Monosaccharides are classified according to three
different characteristics:
– The placement of its carbonyl
– The number of carbon atoms it contains, and
– Its chirality (D- or L-)
19
• Trioses – 3 carbon atom e.g. glyceraldehydes
• Tetroses – 4 carbon atom e.g. threose, erythrose
• Pentoses – 5 carbon atom e.g. Arabinose, Xylose,
Ribose
• Hexoses – 6 carbon atom e.g. glucose, fructose,
mannose and galactose.
• Heptoses – 7 carbon atom e.g. Digitoxose, Cymarose
Classification…
20
Classification…
• Oligosaccharides
– Contain usually 2-12 sugar units linked to each
other by what is known as glycosidic linkage
– Can be hydrolyzed by dilute acids or enzymes to
give 2-12 monosaccharide units
• Classified based on their number of sugar units.
• 2 monosaccharides = disaccharides
• 3 monosaccharides = trisaccharides
21
Classification…
22
C
CHOH
CHOH
C
CHOH
O H
CH2OH
C
CHOH
CHOH
C
CHOH
O H
CH2OH
O H
H
+ H2O
H or OH
C
CHOH
CHOH
C
CHOH
O H
CH2OH
C
CHOH
CHOH
C
CHOH
O H
CH2OH
OH
HO
OH
H
- H2O
glycosidic bond
Classification…
Disaccharides
• Can be hydrolyzed to two monosaccharides
• Examples
– Sucrose:- composed of glucose and fructose
– Maltose:- composed of two molecules of glucose
– Lactose:- composed of glucose and galactose &
glucose
23
Formation of Disaccharides
24
Hydrolysis of a Disaccharide
25
Classification…
Trisaccharides
– Can be hydrolyzed to three monosaccharides
Examples
– Raffinose: can be hydrolyzed by enzymes of
intestinal bacteria to glucose, fructose, and
galactose.
26
Classification…
Polysaccharides
– Consist of many monosaccharide units linked to each
other by glycosidic bond.
– Could be;
 Homopolysacchrides, composed of only one type
of monosaccharide
 e.g.: starch, cellulose, glycogen, inulin and chitin.
27
Classification…
• Heteropolysaccharides, more than one type of
monosaccharides …. Also called heteroglycans
• Mucopolysaccharides or Glycosaminoglycans (GAGs)
are the heteroglycans consistis of a repeating
disaccharide unit.
• The repeating unit consists of an amino sugar along
with a uronic sugar (glucuronic acid or iduronic acid)
or galactose.
E.g hyaluronic acid, chondroitin sulphate and heparin. made of
repeating units of sugar derivatives like amino sugars and uronic
acids
28
Chondroitin sulfate
• Composed of a chain of alternating sugars (N-
acetylgalactosamine and glucuronic acid)
• Important structural component of cartilage and
provides much of its resistance to compression
• Used as dietary supplement for treatment of
osteoarthritis.
29
Classification…
30
Chemical structure of one unit in a chondroitin
sulfate chain.
Chondroitin-4-sulfate: R1 = H; R2 = SO3H; R3 = H.
Chondroitin-6-sulfate: R1 = SO3H; R2, R3 = H.
Acetylgalactosamine
Glucuronic acid
Hyaluronan/ hyaluronic acid
• Non-sulfated glycosaminoglycan distributed widely
throughout connective, epithelial, and neural tissues.
• Hyaluronan is a polymer of disaccharides, composed
of D-glucuronic acid and acetylglucosamine
• It is component of articular cartilage, skin
31
Classification…
32
Hyaluronan/ hyaluronic acid
• The FDA has approved the use of hyaluronic acid
during certain eye surgeries
– It is injected into the eye during the procedure to
help replace natural fluids.
• For various joint disorders, including osteoarthritis.
• For healing wounds, burns, skin ulcers, as a
moisturizer.
33
Classification…
Relations among different carbohydrates
Isomers
• Isomers are molecules that have the same molecular
formula, but have a different arrangement of the
atoms in space (different structures).
• Examples of isomers: Glucose, Fructose, Galactose,
Mannose ………..the same chemical formula C6 H12
O6
34
Relations among…..
Epimers
• Epimers are sugars that differ in configuration at only
1 position.
• Examples of epimers :
– D-glucose & D-galactose (epimeric at C4)
– D-glucose & D-mannose (epimeric at C2)
35
Relations among…..
36
Enantiomers
1. Monosaccharides contain one or more asymmetric C-
atoms: get D- and L-forms, where D- and L- designate
absolute configuration
2. D-form: -OH group is attached to the right of the
asymmetric carbon
3. L-form: -OH group is attached to the left of the
asymmetric carbon
4. If there is more than one chiral C-atom: absolute
configuration of chiral C furthest away from carbonyl
group determines whether D- or L-
Relations among…..
37
e.g
of
chiral
Carbon
atoms
38
Sugars
Monosachrides
Ribose:
• Is an aldopentose that, in its open chain form, has an
aldehyde functional group at one end
• Ribose exists in an equilibrium among 5 forms:
– the linear form and
– either of the two ring forms: alpha- or beta-
ribofuranose, with a 5-membered ring, and alpha- or
beta-ribopyranose
39
40
• The ribose β-D-ribofuranose forms part of the backbone of
RNA.
• It is related to deoxyribose, which is found in DNA
Uses:
• D-ribose is often marketed as a supplement for
bodybuilders, for recovery or increasing muscle mass
in healthy people.
• D-ribose has also been used to reduce fatigue in
fibromyalgia.
41
Sugars …
Xylose
• Xylose or wood sugar, is an aldopentose -- a
monosaccharide.
• Xylose is found in straw, oat hulls and in most woods.
• In animal medicine, xylose is used to test for
malabsorption (if 25 g po of D-xylose is given to
normal patients 4.5 g in 5 hrs will be excreted in the
urine ) .
42
Sugars …
43
Oat hulls
Sugars …
Mannose
• Sugar monomer of the aldohexose series of
carbohydrates.
• Mannose is a C-2 epimer of glucose.
• Mannose commonly exists as two different sized rings,
the pyranose form and the furanose form.
• Mannose is widely distributed in nature in the form of
anhydride-like condensation products termed
mannosans
44
Sugars…
• Sugar extract from the sap is extracted by making a
cut in the bark Fraxinus ornus
45
Fraxinus ornus
Sugars…
Galactose
• Galactose is a type of sugar which is less sweet than
glucose.
• It is a C-4 epimer of glucose
• It is considered a nutritive sweetener because it has
food energy
46
Sugars …
• Galactose is found in dairy products, tomatoes, sugar
beets, etc
• It is also synthesized by the body, where it forms part
of glycolipids and glycoproteins in several tissues
47
Sugars…
Sugars…
D-glucose (dextrose , α-D-glucopyranose, grape sugar)
• C6H12O6 , It is found in honey and the juices of many
fruits
• Glucose is made industrially by the hydrolysis of
starch under the influence of dilute acid.
48
49
• Glucose is stored as a polymer, in plants as starch
and in animals as glycogen.
• Many crops can be used as the source of starch.
• Maize, rice, wheat, cassava, are all used in various
parts of the world
Sugars…
50
Cassava, Beta vulgaris, sugar beet
Sugars…
Uses
– As sweetener ….In the preparation of syrups and
elixirs
– For coating tablets and as tablet binder
– It is used as a nutrient in food and dextrose
injection in replacement therapy usually at 5% and
10%.
51
Sugars…
Sugars…
– It is used as a fluid and nutrient replenisher.
– It also present in anticoagulant citrate phosphate
dextrose solution.
– Used commercially in the manufacture of candy,
carbonated beverages, ice cream,etc.
52
53
Sugars…
Sugars…
D-fructose (levulose)
• Is present practically in all fruits and honey
• Commercially, fructose is frequently derived from
sugar cane, sugar beets, and corn.
54
Sugars…
• It is the sweetest of all naturally occurring
carbohydrates.
• In general, fructose is regarded as being 1.73 times
as sweet as sucrose.
• However, it is the 6-membered ring form of fructose
that is sweeter
55
Crude drug containing sugar
Honey
• Honey is thick, syrupy, translucent liquid when fresh
but becomes opaque and granular through time due
to crystallization of glucose
• It is pale yellow to reddish brown
• It posses sweet taste and usually pleasant flavor
(odor & taste) that varies depending on the nectar
source
56
Sugars…
Chemical constituents:
• Honey contains chiefly D-glucose (30-40%), fructose
(40-50%) and small amounts of sucrose (0.1-10%),
pollen grains, and volatile oil
57
Sugars…
Medicinal uses and health effects of honey
• Honey has antibacterial activity
• Diabetic ulcers when the patient cannot use other
topical antibiotics
• Mild forms of conjunctivitis
• Due to its antiseptic properties, it can be taken orally
by Pharyngitis and Laryngitis sufferers, in order to
soothe them
• Mild laxative (for constipation)
• Sedative (for mild insomnia)
58
Sugars…
Cymarose and Digitoxose
– Cymarose is closely resembles to digitoxose in
behaviour and is considered to be a methylether
of digitoxose.
– Cymarose are obtained on hydrolysis of the
glucosides cymarin (from the root of apocyanum)
59
Sugars …
Digitoxose, (C 6 H 12 O 4)
• The leaves of Digitalis purpurea contain apparently
more than five glycosides which form the active
constituents of digitalis
• Digitoxin the most active principle, is insoluble in
water; on hydrolysis it forms digitoxigenin and a
sugar, digitoxose.
60
Sugars and…
Disaccharides
Sucrose (saccharum, sugar or table sugar)
• It is O-β-D- fructofuranosyl-(2 ↔ 1)-α-D-glucopyranose
• Sucrose is a disaccharide composed of D-glucose and
D-fructose.
• It is a the most abundant disaccharide and the main
form in which carbohydrates are transported in
plant.
61
Sugars and…
Sugars…
• Important commercial sources of sucrose are
– Sugar cane: Saccharum officinarum
– Sugar beet: Beta vulgaris
62
Sugars…
• When sucrose is hydrolyzed by dilute acid solution, it
produces equal amounts of D-glucose and D-
fructose.
• This mixture is commonly known as invert sugar.
63
Sugars…
Uses
– As sweetener
– In the preparation of syrups and elixirs
– For coating tablets and as tablet binder
– For manufacturing lozenges and pastilles
– As a demulcent and as a nutrient
– Act as bacteriostatic agent and preservative if
used in high concentration
64
Lactose, milk sugar
• Lactose is a disaccharide composed of D-galactose
and D-glucose units
• It found most notably in milk .Lactose makes up
around 2–8% of milk (by weight)
• It is only faintly sweet, and its principal use is as a
diluent in tablet formulations
65
Sugars…
Polysaccharides
Polysaccharides
• They consist of repeat units of monosaccharides or
their derivatives.
• They are colourless and tasteless.
• They are concerned with two important functions -
structural and storage of energy.
66
Starch
• Starch for medicinal and pharmaceutical use consists
of polysaccharide carbohydrate occurring as discrete
granules in:
– The mature grain of maize or corn (Zea mays)
– The mature grain of wheat (Triticum aestivum)
– The mature grain of rice (Oryza sativa)
– Tubers of potato (Solanum tuberosum)
67
Polysaccharides…
68
Polysaccharides…
Starch
Character:
• Starch occurs as granules with different shapes,
patterns and size (diameter = 2-100 μm) depending
on the botanical source.
– Wheat starch: 2-23 μm
– Corn starch: 25-32 μm
– Potato starch 30-100 μm
• Starch granules are insoluble in water
69
Polysaccharides…
Chemical composition:
Starch granules are composed of two glucans known as
amylose and amylopectin
Characteristics Amylose Amylopectin
Average amount 20-25% 75-80%
Average no of glucose
units
250-300 More than 1000
Structure Linear non-
branching
Linear branching
Connectivity of
glucose units
Exclusively by
α(1→4) linkage
α(1→4) linkage in the main
chain and α(1→6) linkage
at branching points
Water solubility Water soluble Water insoluble but swells
in water
Color with iodine Deep-blue Blue-violet or purple 70
Polysaccharides…
Amylose – a straight chain structure formed by 1,4
glycosidic bonds between α-D-glucose molecules.
H O
OH
H
OH
H
OH
CH2OH
H
O H
H
OH
H
OH
CH2OH
H
O
H
H H O
O
H
OH
H
OH
CH2OH
H
H H O
H
OH
H
OH
CH2OH
H
OH
H
H O
O
H
OH
H
OH
CH2OH
H
O
H
1
6
5
4
3
1
2
amylose
Structure of Amylose Fraction of Starch
71
Polysaccharides…
Amylopectin-a glucose polymer with mainly α -(14)
linkages, but it also has branches formed by α -(16)
linkages.
H O
OH
H
OH
H
OH
CH2OH
H
O H
H
OH
H
OH
CH2OH
H
O
H
H H O
O
H
OH
H
OH
CH2
H
H H O
H
OH
H
OH
CH2OH
H
OH
H
H O
O
H
OH
H
OH
CH2OH
H
O
H
O
1 4
6
H O
H
OH
H
OH
CH2OH
H
H H O
H
OH
H
OH
CH2OH
H
H
O
1
OH
3
4
5
2
amylopectin
Structure of Amylopectin Fraction of Starch
72
Branch
Polysaccharides…
Medicinal uses:
– As binder (because of amylose…. Water soluble)
– As disintegrants (because of amylopectin.. Swell in
water)
– As tablet filler
– As absorbent in dusting powders
73
Polysaccharides…
Dextran
• Dextran contains from 200-400 glucose units with
predominant linkage is α(1,6)
• 3.5 or 10% solution dextran is used for plasma
volume expansion in the treatment of shock, means
of parenteral nutrition
• Dextran is also used in lubricant eye drops designed
to minimize discomfort from contact lens
74
Polysaccharides…
Cellulose
• The β-glucose molecules are joined together forming
β-(1,4) glycosidic linkages.
• The glucose units are linked into straight chains each
100-1000 units long.
• Weak hydrogen bonds form between parallel chains
binding them into cellulose microfibrils.
• Cellulose microfibrils arrange themselves into thicker
bundles called microfibrils…….fibres
75
Polysaccharides…
• The cellulose fibres are often “glued” together by
other compounds such as hemicelluloses and
calcium pectate ……..plant cell walls.
• Cellulose is the principal structural element of higher
plant cell walls
• Cellulose is commercially obtained from:
– Hair of the seed of cotton plant
– Wood
76
Polysaccharides…
77
Polysaccharides…
78
Polysaccharides…
79
Cellulose
80
Polysaccharides…
Use
• Surgical dressing
• For preparing absorbent gauze
• Powdered cellulose is used as tablet diluent and
disintegrants
81
Polysaccharides…
Cellulose
Cellulose acetate phtalate (CAP)
- entricoating tablets
Hydroxypropylmethylcellulose
- suspending agent
- thickening agent
Ethylcellulose
- tablet binder
Methylcellulose
- bulk laxative
- suspending agent
- Artificial tear
+ for xerophtalmia
+ contact lens
Sodium carbonylmethylcellulose (CMC)
- thickening agent
- bulk laxative
Cellulose is extensively modified;
82
Polysaccharides…
Glycogen
• Is a polysaccharide of glucose which functions as the
secondary short term energy storage in animal cells
• It is made primarily by the liver and the muscle, but
can also be made by the brain and stomach
• Glycogen is the analogue of starch commonly
referred to as animal starch
83
Polysaccharides…
Gums and mucilage
Consists of Ca, Mg and K salts of polyuronoides that
are hydrolyzed by boiling with acids to monosaccharide
and uronic acid or galactouronic acid
84
Polysaccharides…
• Gums are considered to be pathological products
formed upon injury of the plant or owing to
unfavorable conditions such as drought
• The formation of gums is known as gummosis which
involves the break down of cell walls and thus it is an
extracellular process
• Mucilages are normal products of metabolism,
formed with in cells (intracellular formation)
85
Polysaccharides…
• Mucilages usually serve as storage materials, water-
storage reservoirs, or may provide protection for
germinating seeds
• Insoluble in alcohol and in most organic solvents but
soluble in water yielding viscous, usually adhesive
colloidal solutions
86
Polysaccharides…
Pharmaceutically important gums
• Acacia gum is the dried gummy exudate obtained
from the stem and branches of Acacia senegal and
some related species like Acacia arabica
• Acacia gum contains chiefly arabin (mixture of
calcium, magnesium and potassium salts of arabic
acid)
• On hydrolysis arabic acid yields L-rhamnose, L-
arabinose, D-galactose and D-glucuronic acid 87
Polysaccharides…
88
mucilage
Polysaccharides…
Acacia gum is used:
• As demulcent (added in formulations for cough,
diarrhea and throat problems)
• As emollient (to cover burns, sore nipples etc)
• As emulsifying agent (for oil in water emulsions)
• As binder in tablets especially in lozenges.
• Commercially as adhesive
89
Polysaccharides…
Gum tragacanth
• Tragacanth is the dried gummy exudate obtained
from the stems of Astragalus gummifer and other
related species
• Gum tragacanth contains targacanthin and bassorin
– Targacanthin is the water soluble portion and is
1/3 of the mass
– Bassorin is the water insoluble portion and is 2/3
of the mass…….Bassorin swells to from a gel
90
Polysaccharides…
91
Astragalus gummifer
Polysaccharides…
• Gum tragacanth is used
– As suspending and emulsifying agent
– As binder in pills and tablets
– As a bulk laxative
– Gum tragacanth is resistant to acid hydrolysis so it
is preferred in acidic preparations.
92
Polysaccharides…
Pharmaceutically important mucilages
Agar
• Agar is the dried, acidic, hydrophilic colloidal
polysaccharide complex extracted from different red
algae species such as:
– Gelidium cartilagineum
– Gracilaria confervoides
• Agar is composed of acidic polysaccharides that could be
resolved into two fractions:
– Agarose is the gelling fraction
– Agaropectin is the non-gelling fraction
93
Polysaccharides…
94
Polysaccharides…
Gelidium cartilagineum
culture media
Agar is used
• As suspending and emulsifying agent
• As gelling agent for suppositories
• As tablet filler and disintegrant
• For the treatment chronic constipation (bulk laxative)
• For the preparation of culture media (1% solution)
95
Polysaccharides…
Algin (Sodium alginate)
• Algin is a polysaccharide extracted from different
strains of brown seaweed by the use of dilute alkali
• It is chiefly obtained from Macrocystis pyrifera
• Sodium alginate yields D-mannuronic acid and L-
glucuronic acid
• Algin is readily water-soluble
96
Polysaccharides…
97
Macrocystis pyrifera
Polysaccharides…
Algin is used
• As suspending and emulsifying agent
• As thickening agent
• As tablet binder
• Food (ice cream)
• Commercially it s widely used in cosmetics and
textile
98
Polysaccharides…
Pectin
• Cell walls of higher
plants
• Largely a linear polymer
of polygalacturonic acid
with varying degrees of
methyl esterification.
99
Polysaccharides…
Use
• as gelling agent
• Thickeners
• Laxative
• used in throat lozenges as a demulcent
100
Polysaccharides…
Chitin
• Chitin is the second most abundant carbohydrate
polymer
• It is modified polysaccharide that contains
nitrogen;………..units of N-acetylglucosamine
• Cellulose with one hydroxyl group on each monomer
replaced with an acetyl amine group.
• Present in the cell wall of fungi and in the
exoskeletons of crustaceans, insects and spiders
101
Polysaccharides…
102
Polysaccharides…
• Chitin is used commercially in coatings (extends the
shelf life of fruits and meats)
• Chitin's flexibility and strength make it favorable as
surgical thread
103
Polysaccharides…
Plant acids such as citric, lactic, and tartaric acid find
wide application in the formulation of food and
medicine.
Citric acid
Weak organic acid with the formula C6H8O7
104
Sugar related compounds
Sugar related…
– It is a tricarbixylic acid
– First isolated from lemon juice
– Present in many fruits and plants
– Commercially obtained from lemons, pineapples
– Colorless, odorless, translucent crystal and soluble
in water and alcohol
105
Uses
– Useful in buffering system
– Used as an acidulant in effervescent formulation
– An ingredient in anticoagulant, citrate phosphate
dextrose solution
106
Sugar related…
Lactic acid
– Colorless or yellowish, odorless, syrupy liquid
– Miscible with water, alcohol and ether
Uses:
– As acidulant especially in infant feeding formulas
– Sodium lactate injection is a fluid and electrolyte
replenisher
– Calcium lactate - a calcium replenisher
– In topical preparations and cosmetics to adjust acidity and
for its disinfectant and keratolytic properties.
107
Sugar related…
108
Sugar related…
Tartaric acid
– Dicarboxylic acid byproduct of wine industry
– Freely soluble in water
– Used as a substitute for citric acid in buffer system
in effervescent formulations
109
Sugar related…
Mannitol (D-mannitol)
110
• Obtained by the reduction of
mannose or by isolation from
manna
• Manna is the dried saccharine
exudate of barks of Fraxinus ornus
and contains 50-60% of mannitol
Sugar related…
111
Fraxinus ornus
• Occurs as white crystalline powders.
• Odorless and sweetish taste.
• Mannitol is not absorbed in GIT……When
administered parentally, it is not metabolized and
eliminated by glomerular filtration (80% of 100 in 3
hrs)
112
Sugar related…
Medicinal use:
• For diagnosis of kidney function
• As osmotic diuretic
• Also as osmotic laxative for constipation
• As sweetener for diabetics
113
Sugar related…
Sorbitol (D-glucitol or D-sorbitol)
114
Sugar related…
Most sorbitol is made from corn syrup, but
it is also found in apples, also occurs in
many fruits
Sorbitol is an isomer of mannitol
• Commercially it is prepared from glucose by chemical
or electrolytic reduction
• Sorbitol is half as sweet as sucrose and it is not
absorbed from the GIT
115
Sugar related…
Pharmaceutical use:
• Used as osmotic laxative for constipation.
• As sweetener for diabetics
• It is commonly used in toothpastes, chewing gums
116
Sugar related…
Qualitative Test to Detect CHOs
• Is concerned with determining the identity of a
substance.
– Molisch Test- carbohydrates
– I2 Test - Cellulose, Starch, Dextrin
– Seliwanoff’s Test- Ketose from Aldose
– Test for Reducing Sugars (Barfoed’s TestFT )
117
Qualitative test…
Molisch test
• Aqueous solution of carbohydrate mixed with few
drops of Molisch reagent (alpha naphthol) and Conc.
H2SO4 was added from sidewall of test tube.
• Formation of purple coloured ring at junction
indicates presence of carbohydrates.
118
119
Qualitative test…
Iodine test
• It is specific for polysacchrides.
• Few drops of Iodine solution is added to aqueous
solution of polysaccharide.
• Formation of blue colour, which disappears on
heating and reappears on cooling, indicates the
presence of starch.
Qualitative test…
120
121
Qualitative test…
Barford test
• This test is used to distinguish between monosacchride
and disacchrides.
• Two ml of Barford reagent (Cupric acetate, acetic acid
and water) was added to 1 ml aqueous solution of
carbohydrates and boil.
• Formation of brick red precipitate in 5 minutes indicates
presence of monosacchride while in 7 minutes indicates
disaccharide.
Qualitative test…
122
123
Qualitative test…
Seliwanoff’s test
• This test is used for identification of keto-hexoses or
to distinguish between ketoses and aldoses.
• To 1 ml aqueous solution of drug, 5 ml of
Seliwanoff’s reagent (resorcinol in 6M HCl) was
added and boiled.
• Formation of cherry red colour in presence of ketose
(e.g fructose) due to formation of hydroxyl methyl
furfural
Qualitative test…
124
125
Qualitative test…
Fehling solution test
• It is generally used for reducing sugars and
composed of two solutions, which are mixed in situ.
• Fehling solution A composed of 0.5% of copper
sulphate whereas Fehling solution B composed of
Sodium Potassium Tartarate.
Qualitative test…
126
• Equal volumes of Fehling A and Fehling B solutions
were mixed (1 ml each) and 2 ml of aqueous solution
of drug was added followed by boiling for 5-10
minutes on water bath.
• Formation of reddish brown coloured precipitate due
to formation of Cuprous oxide indicates presence of
reducing sugar.
127
Qualitative test…
128
Qualitative test…
129
Qualitative test…
Benedict’s test
• It is used for reducing sugars and composed of mainly
Copper sulphate and sodium hydroxide.
• To the 4 ml of aqueous solution of drug, 1 ml of
Benedicts solution was added and heated almost to
boiling.
• Formation of green, yellow, orange, red or brown colour
in order of increasing concentration of simple sugar in
the test solution, due to formation of cuprous oxide.
Qualitative test…
130
131
Qualitative test…

Weitere ähnliche Inhalte

Ähnlich wie carbohydrate.pptx

Chemistry of Natural Product Type.pptx
Chemistry of  Natural Product Type.pptxChemistry of  Natural Product Type.pptx
Chemistry of Natural Product Type.pptxJACOB THON BIOR
 
Biochemistry-Unit 5.pptx
Biochemistry-Unit 5.pptxBiochemistry-Unit 5.pptx
Biochemistry-Unit 5.pptxShridhanAmbhore
 
Carbohydrates.pptx
Carbohydrates.pptxCarbohydrates.pptx
Carbohydrates.pptxBinteHawah1
 
Chemistry of Carbohydrates.pptx
Chemistry of Carbohydrates.pptxChemistry of Carbohydrates.pptx
Chemistry of Carbohydrates.pptxabeerarajput
 
Chemistry of carbohydrates
Chemistry of carbohydratesChemistry of carbohydrates
Chemistry of carbohydratesRaj Dangol
 
Carbohydrate Str, Func and classification.pdf
Carbohydrate Str, Func and classification.pdfCarbohydrate Str, Func and classification.pdf
Carbohydrate Str, Func and classification.pdfpriyanshpatel29
 
Lec5 level3-dechemistryofcarbohydrates-130202043028-phpapp01
Lec5 level3-dechemistryofcarbohydrates-130202043028-phpapp01Lec5 level3-dechemistryofcarbohydrates-130202043028-phpapp01
Lec5 level3-dechemistryofcarbohydrates-130202043028-phpapp01Cleophas Rwemera
 
BRIEF EXPLANATION OF CARBOHYDRATE
BRIEF EXPLANATION OF CARBOHYDRATEBRIEF EXPLANATION OF CARBOHYDRATE
BRIEF EXPLANATION OF CARBOHYDRATEBishnuPatra1
 
Carbohdrates 2013
Carbohdrates 2013Carbohdrates 2013
Carbohdrates 2013Dr-HAMDAN
 
CHO.pptx
CHO.pptxCHO.pptx
CHO.pptxLijFire
 
7-chemistry-of-carbohydrates.ppt
7-chemistry-of-carbohydrates.ppt7-chemistry-of-carbohydrates.ppt
7-chemistry-of-carbohydrates.pptHENRYCVALERIO
 
Chemistry of Carbohydrates
Chemistry of CarbohydratesChemistry of Carbohydrates
Chemistry of CarbohydratesChahat Middha
 

Ähnlich wie carbohydrate.pptx (20)

4.1 carbohydrates.ppt
4.1 carbohydrates.ppt4.1 carbohydrates.ppt
4.1 carbohydrates.ppt
 
Chemistry of Natural Product Type.pptx
Chemistry of  Natural Product Type.pptxChemistry of  Natural Product Type.pptx
Chemistry of Natural Product Type.pptx
 
Biochemistry-Unit 5.pptx
Biochemistry-Unit 5.pptxBiochemistry-Unit 5.pptx
Biochemistry-Unit 5.pptx
 
Carbohydrates.pptx
Carbohydrates.pptxCarbohydrates.pptx
Carbohydrates.pptx
 
Chemistry of Carbohydrates.pptx
Chemistry of Carbohydrates.pptxChemistry of Carbohydrates.pptx
Chemistry of Carbohydrates.pptx
 
Carbohydrates
Carbohydrates Carbohydrates
Carbohydrates
 
Chemistry of carbohydrates
Chemistry of carbohydratesChemistry of carbohydrates
Chemistry of carbohydrates
 
Carbohydrates - k.pptx
Carbohydrates - k.pptxCarbohydrates - k.pptx
Carbohydrates - k.pptx
 
L6 Carbohydrates.pptx
L6 Carbohydrates.pptxL6 Carbohydrates.pptx
L6 Carbohydrates.pptx
 
Carbohydrate Str, Func and classification.pdf
Carbohydrate Str, Func and classification.pdfCarbohydrate Str, Func and classification.pdf
Carbohydrate Str, Func and classification.pdf
 
Lec5 level3-dechemistryofcarbohydrates-130202043028-phpapp01
Lec5 level3-dechemistryofcarbohydrates-130202043028-phpapp01Lec5 level3-dechemistryofcarbohydrates-130202043028-phpapp01
Lec5 level3-dechemistryofcarbohydrates-130202043028-phpapp01
 
BRIEF EXPLANATION OF CARBOHYDRATE
BRIEF EXPLANATION OF CARBOHYDRATEBRIEF EXPLANATION OF CARBOHYDRATE
BRIEF EXPLANATION OF CARBOHYDRATE
 
Carbohdrates 2013
Carbohdrates 2013Carbohdrates 2013
Carbohdrates 2013
 
1. ppt_701_CHO.pdf
1. ppt_701_CHO.pdf1. ppt_701_CHO.pdf
1. ppt_701_CHO.pdf
 
CHO.pptx
CHO.pptxCHO.pptx
CHO.pptx
 
7-chemistry-of-carbohydrates.ppt
7-chemistry-of-carbohydrates.ppt7-chemistry-of-carbohydrates.ppt
7-chemistry-of-carbohydrates.ppt
 
Chemistry of Carbohydrates
Chemistry of CarbohydratesChemistry of Carbohydrates
Chemistry of Carbohydrates
 
Carbohydrates
CarbohydratesCarbohydrates
Carbohydrates
 
CARBOHYDRATES
CARBOHYDRATESCARBOHYDRATES
CARBOHYDRATES
 
Carbohydrates
CarbohydratesCarbohydrates
Carbohydrates
 

Kürzlich hochgeladen

Presentation by Andreas Schleicher Tackling the School Absenteeism Crisis 30 ...
Presentation by Andreas Schleicher Tackling the School Absenteeism Crisis 30 ...Presentation by Andreas Schleicher Tackling the School Absenteeism Crisis 30 ...
Presentation by Andreas Schleicher Tackling the School Absenteeism Crisis 30 ...EduSkills OECD
 
Sports & Fitness Value Added Course FY..
Sports & Fitness Value Added Course FY..Sports & Fitness Value Added Course FY..
Sports & Fitness Value Added Course FY..Disha Kariya
 
Arihant handbook biology for class 11 .pdf
Arihant handbook biology for class 11 .pdfArihant handbook biology for class 11 .pdf
Arihant handbook biology for class 11 .pdfchloefrazer622
 
SOCIAL AND HISTORICAL CONTEXT - LFTVD.pptx
SOCIAL AND HISTORICAL CONTEXT - LFTVD.pptxSOCIAL AND HISTORICAL CONTEXT - LFTVD.pptx
SOCIAL AND HISTORICAL CONTEXT - LFTVD.pptxiammrhaywood
 
BAG TECHNIQUE Bag technique-a tool making use of public health bag through wh...
BAG TECHNIQUE Bag technique-a tool making use of public health bag through wh...BAG TECHNIQUE Bag technique-a tool making use of public health bag through wh...
BAG TECHNIQUE Bag technique-a tool making use of public health bag through wh...Sapna Thakur
 
Call Girls in Dwarka Mor Delhi Contact Us 9654467111
Call Girls in Dwarka Mor Delhi Contact Us 9654467111Call Girls in Dwarka Mor Delhi Contact Us 9654467111
Call Girls in Dwarka Mor Delhi Contact Us 9654467111Sapana Sha
 
9548086042 for call girls in Indira Nagar with room service
9548086042  for call girls in Indira Nagar  with room service9548086042  for call girls in Indira Nagar  with room service
9548086042 for call girls in Indira Nagar with room servicediscovermytutordmt
 
Kisan Call Centre - To harness potential of ICT in Agriculture by answer farm...
Kisan Call Centre - To harness potential of ICT in Agriculture by answer farm...Kisan Call Centre - To harness potential of ICT in Agriculture by answer farm...
Kisan Call Centre - To harness potential of ICT in Agriculture by answer farm...Krashi Coaching
 
Software Engineering Methodologies (overview)
Software Engineering Methodologies (overview)Software Engineering Methodologies (overview)
Software Engineering Methodologies (overview)eniolaolutunde
 
Q4-W6-Restating Informational Text Grade 3
Q4-W6-Restating Informational Text Grade 3Q4-W6-Restating Informational Text Grade 3
Q4-W6-Restating Informational Text Grade 3JemimahLaneBuaron
 
Introduction to Nonprofit Accounting: The Basics
Introduction to Nonprofit Accounting: The BasicsIntroduction to Nonprofit Accounting: The Basics
Introduction to Nonprofit Accounting: The BasicsTechSoup
 
1029 - Danh muc Sach Giao Khoa 10 . pdf
1029 -  Danh muc Sach Giao Khoa 10 . pdf1029 -  Danh muc Sach Giao Khoa 10 . pdf
1029 - Danh muc Sach Giao Khoa 10 . pdfQucHHunhnh
 
Accessible design: Minimum effort, maximum impact
Accessible design: Minimum effort, maximum impactAccessible design: Minimum effort, maximum impact
Accessible design: Minimum effort, maximum impactdawncurless
 
BASLIQ CURRENT LOOKBOOK LOOKBOOK(1) (1).pdf
BASLIQ CURRENT LOOKBOOK  LOOKBOOK(1) (1).pdfBASLIQ CURRENT LOOKBOOK  LOOKBOOK(1) (1).pdf
BASLIQ CURRENT LOOKBOOK LOOKBOOK(1) (1).pdfSoniaTolstoy
 
Grant Readiness 101 TechSoup and Remy Consulting
Grant Readiness 101 TechSoup and Remy ConsultingGrant Readiness 101 TechSoup and Remy Consulting
Grant Readiness 101 TechSoup and Remy ConsultingTechSoup
 
1029-Danh muc Sach Giao Khoa khoi 6.pdf
1029-Danh muc Sach Giao Khoa khoi  6.pdf1029-Danh muc Sach Giao Khoa khoi  6.pdf
1029-Danh muc Sach Giao Khoa khoi 6.pdfQucHHunhnh
 
Web & Social Media Analytics Previous Year Question Paper.pdf
Web & Social Media Analytics Previous Year Question Paper.pdfWeb & Social Media Analytics Previous Year Question Paper.pdf
Web & Social Media Analytics Previous Year Question Paper.pdfJayanti Pande
 
Organic Name Reactions for the students and aspirants of Chemistry12th.pptx
Organic Name Reactions  for the students and aspirants of Chemistry12th.pptxOrganic Name Reactions  for the students and aspirants of Chemistry12th.pptx
Organic Name Reactions for the students and aspirants of Chemistry12th.pptxVS Mahajan Coaching Centre
 

Kürzlich hochgeladen (20)

Presentation by Andreas Schleicher Tackling the School Absenteeism Crisis 30 ...
Presentation by Andreas Schleicher Tackling the School Absenteeism Crisis 30 ...Presentation by Andreas Schleicher Tackling the School Absenteeism Crisis 30 ...
Presentation by Andreas Schleicher Tackling the School Absenteeism Crisis 30 ...
 
Sports & Fitness Value Added Course FY..
Sports & Fitness Value Added Course FY..Sports & Fitness Value Added Course FY..
Sports & Fitness Value Added Course FY..
 
Arihant handbook biology for class 11 .pdf
Arihant handbook biology for class 11 .pdfArihant handbook biology for class 11 .pdf
Arihant handbook biology for class 11 .pdf
 
SOCIAL AND HISTORICAL CONTEXT - LFTVD.pptx
SOCIAL AND HISTORICAL CONTEXT - LFTVD.pptxSOCIAL AND HISTORICAL CONTEXT - LFTVD.pptx
SOCIAL AND HISTORICAL CONTEXT - LFTVD.pptx
 
BAG TECHNIQUE Bag technique-a tool making use of public health bag through wh...
BAG TECHNIQUE Bag technique-a tool making use of public health bag through wh...BAG TECHNIQUE Bag technique-a tool making use of public health bag through wh...
BAG TECHNIQUE Bag technique-a tool making use of public health bag through wh...
 
Call Girls in Dwarka Mor Delhi Contact Us 9654467111
Call Girls in Dwarka Mor Delhi Contact Us 9654467111Call Girls in Dwarka Mor Delhi Contact Us 9654467111
Call Girls in Dwarka Mor Delhi Contact Us 9654467111
 
9548086042 for call girls in Indira Nagar with room service
9548086042  for call girls in Indira Nagar  with room service9548086042  for call girls in Indira Nagar  with room service
9548086042 for call girls in Indira Nagar with room service
 
Kisan Call Centre - To harness potential of ICT in Agriculture by answer farm...
Kisan Call Centre - To harness potential of ICT in Agriculture by answer farm...Kisan Call Centre - To harness potential of ICT in Agriculture by answer farm...
Kisan Call Centre - To harness potential of ICT in Agriculture by answer farm...
 
Mattingly "AI & Prompt Design: The Basics of Prompt Design"
Mattingly "AI & Prompt Design: The Basics of Prompt Design"Mattingly "AI & Prompt Design: The Basics of Prompt Design"
Mattingly "AI & Prompt Design: The Basics of Prompt Design"
 
Software Engineering Methodologies (overview)
Software Engineering Methodologies (overview)Software Engineering Methodologies (overview)
Software Engineering Methodologies (overview)
 
Q4-W6-Restating Informational Text Grade 3
Q4-W6-Restating Informational Text Grade 3Q4-W6-Restating Informational Text Grade 3
Q4-W6-Restating Informational Text Grade 3
 
Introduction to Nonprofit Accounting: The Basics
Introduction to Nonprofit Accounting: The BasicsIntroduction to Nonprofit Accounting: The Basics
Introduction to Nonprofit Accounting: The Basics
 
1029 - Danh muc Sach Giao Khoa 10 . pdf
1029 -  Danh muc Sach Giao Khoa 10 . pdf1029 -  Danh muc Sach Giao Khoa 10 . pdf
1029 - Danh muc Sach Giao Khoa 10 . pdf
 
Accessible design: Minimum effort, maximum impact
Accessible design: Minimum effort, maximum impactAccessible design: Minimum effort, maximum impact
Accessible design: Minimum effort, maximum impact
 
BASLIQ CURRENT LOOKBOOK LOOKBOOK(1) (1).pdf
BASLIQ CURRENT LOOKBOOK  LOOKBOOK(1) (1).pdfBASLIQ CURRENT LOOKBOOK  LOOKBOOK(1) (1).pdf
BASLIQ CURRENT LOOKBOOK LOOKBOOK(1) (1).pdf
 
Grant Readiness 101 TechSoup and Remy Consulting
Grant Readiness 101 TechSoup and Remy ConsultingGrant Readiness 101 TechSoup and Remy Consulting
Grant Readiness 101 TechSoup and Remy Consulting
 
1029-Danh muc Sach Giao Khoa khoi 6.pdf
1029-Danh muc Sach Giao Khoa khoi  6.pdf1029-Danh muc Sach Giao Khoa khoi  6.pdf
1029-Danh muc Sach Giao Khoa khoi 6.pdf
 
Web & Social Media Analytics Previous Year Question Paper.pdf
Web & Social Media Analytics Previous Year Question Paper.pdfWeb & Social Media Analytics Previous Year Question Paper.pdf
Web & Social Media Analytics Previous Year Question Paper.pdf
 
Código Creativo y Arte de Software | Unidad 1
Código Creativo y Arte de Software | Unidad 1Código Creativo y Arte de Software | Unidad 1
Código Creativo y Arte de Software | Unidad 1
 
Organic Name Reactions for the students and aspirants of Chemistry12th.pptx
Organic Name Reactions  for the students and aspirants of Chemistry12th.pptxOrganic Name Reactions  for the students and aspirants of Chemistry12th.pptx
Organic Name Reactions for the students and aspirants of Chemistry12th.pptx
 

carbohydrate.pptx

  • 1. Major Medicinally Important 1o and 2o Metabolites 1
  • 3. Session outline • Introduction • Classification • Relations among different carbohydrates • Sugars • Polysaccharides • Compounds related to sugars • Qualitative tests for carbohydrates 3
  • 4. Four Major Types of Biological Macromolecules Type of Polymer Monomers making up Polymer Example I. Carbohydrates (Polysaccharides) Monosaccharides Sugars, Starch, Cellulose II. Lipids Fatty acids and glycerol Fats, steroids, cholesterol III. Proteins Amino acids Enzymes, structural components IV. Nucleic Acids Nucleotides DNA, RNA Introduction
  • 5. Introduction Definition – carbohydrate(hydrated carbon) – Is a polyhydroxy aldehyde or ketone or a larger molecule which can be hydrolyzed to a polyhydroxy aldehyde or ketone or their derivatives 5
  • 6. Introduction… – Are the most abundant compounds found in plant (cellulose, starch, sugars) and animals (glycogen) – In most cases, composed of only C, H and O , with general formula of (CH2O)n – Usually the ratio of H to O is 2:1 6
  • 7. Introduction… However there are exceptions for this rule  There are compounds that conform to the hydrate rule (2:1 ratio of H and O) but not carbohydrates E.g. Formaldehyde, HCHO; Acetic acid, CH3COOH 7
  • 8. Introduction…  There are compounds that do not conform to the hydrate rule but have chemical properties of carbohydrates E.g. Deoxy sugars like:Rhamnose(C6H12O5), digitoxose(C6H12O4) 8
  • 9. Introduction… Why do we study carbohydrates in pharmacognosy? • Widely used in pharmaceuticals as additives (suspending agents, emulsifiers, fillers, binders, absorbents/ adsorbents) • Starting material in the synthesis of various compounds 9
  • 10. Introduction… • Many of them have pharmacological activity – Anticoagulant – Hypoglycemic activity – Anti-inflammatory activity – Antimicrobial 10
  • 11. Role in living organism • Storage of energy (e.g., starch and glycogen) • Structural components (e.g., cellulose in plants and chitin in arthropods) • The 5-carbon monosaccharide ribose is an important component of coenzymes (e.g., ATP ) and the backbone of the genetic molecule known as RNA. 11 Introduction…
  • 12. 12 Sources • Major sources of carbohydrates are plants • E.g Glucose is produced in plants through photosynthesis from CO2 and H2O • Glucose is converted in plants to other small sugars and polymers (cellulose, starch) Introduction…
  • 13. 13 Classification of Carbohydrates I. Number of carbohydrate units • Monosaccharides • Oligosaccharides • Polysaccharides
  • 14. 14 II. Position of carbonyl group aldose: Sugars that contain an aldehyde group ketose: Sugars that contain a ketone group
  • 15. An aldose: Glucose III. Cyclic form • Less then 1% of CHO exist in an open chain form • Pyranose (6-membered ring) and furanose (5-membere)
  • 18. 18 IV. Number of carbons
  • 19. Classification… • Monosaccharides or simple sugars – They contain one sugar units – They cannot be hydrolyzed further • Monosaccharides are classified according to three different characteristics: – The placement of its carbonyl – The number of carbon atoms it contains, and – Its chirality (D- or L-) 19
  • 20. • Trioses – 3 carbon atom e.g. glyceraldehydes • Tetroses – 4 carbon atom e.g. threose, erythrose • Pentoses – 5 carbon atom e.g. Arabinose, Xylose, Ribose • Hexoses – 6 carbon atom e.g. glucose, fructose, mannose and galactose. • Heptoses – 7 carbon atom e.g. Digitoxose, Cymarose Classification… 20
  • 21. Classification… • Oligosaccharides – Contain usually 2-12 sugar units linked to each other by what is known as glycosidic linkage – Can be hydrolyzed by dilute acids or enzymes to give 2-12 monosaccharide units • Classified based on their number of sugar units. • 2 monosaccharides = disaccharides • 3 monosaccharides = trisaccharides 21
  • 22. Classification… 22 C CHOH CHOH C CHOH O H CH2OH C CHOH CHOH C CHOH O H CH2OH O H H + H2O H or OH C CHOH CHOH C CHOH O H CH2OH C CHOH CHOH C CHOH O H CH2OH OH HO OH H - H2O glycosidic bond
  • 23. Classification… Disaccharides • Can be hydrolyzed to two monosaccharides • Examples – Sucrose:- composed of glucose and fructose – Maltose:- composed of two molecules of glucose – Lactose:- composed of glucose and galactose & glucose 23
  • 25. Hydrolysis of a Disaccharide 25
  • 26. Classification… Trisaccharides – Can be hydrolyzed to three monosaccharides Examples – Raffinose: can be hydrolyzed by enzymes of intestinal bacteria to glucose, fructose, and galactose. 26
  • 27. Classification… Polysaccharides – Consist of many monosaccharide units linked to each other by glycosidic bond. – Could be;  Homopolysacchrides, composed of only one type of monosaccharide  e.g.: starch, cellulose, glycogen, inulin and chitin. 27
  • 28. Classification… • Heteropolysaccharides, more than one type of monosaccharides …. Also called heteroglycans • Mucopolysaccharides or Glycosaminoglycans (GAGs) are the heteroglycans consistis of a repeating disaccharide unit. • The repeating unit consists of an amino sugar along with a uronic sugar (glucuronic acid or iduronic acid) or galactose. E.g hyaluronic acid, chondroitin sulphate and heparin. made of repeating units of sugar derivatives like amino sugars and uronic acids 28
  • 29. Chondroitin sulfate • Composed of a chain of alternating sugars (N- acetylgalactosamine and glucuronic acid) • Important structural component of cartilage and provides much of its resistance to compression • Used as dietary supplement for treatment of osteoarthritis. 29 Classification…
  • 30. 30 Chemical structure of one unit in a chondroitin sulfate chain. Chondroitin-4-sulfate: R1 = H; R2 = SO3H; R3 = H. Chondroitin-6-sulfate: R1 = SO3H; R2, R3 = H. Acetylgalactosamine Glucuronic acid
  • 31. Hyaluronan/ hyaluronic acid • Non-sulfated glycosaminoglycan distributed widely throughout connective, epithelial, and neural tissues. • Hyaluronan is a polymer of disaccharides, composed of D-glucuronic acid and acetylglucosamine • It is component of articular cartilage, skin 31 Classification…
  • 33. • The FDA has approved the use of hyaluronic acid during certain eye surgeries – It is injected into the eye during the procedure to help replace natural fluids. • For various joint disorders, including osteoarthritis. • For healing wounds, burns, skin ulcers, as a moisturizer. 33 Classification…
  • 34. Relations among different carbohydrates Isomers • Isomers are molecules that have the same molecular formula, but have a different arrangement of the atoms in space (different structures). • Examples of isomers: Glucose, Fructose, Galactose, Mannose ………..the same chemical formula C6 H12 O6 34
  • 35. Relations among….. Epimers • Epimers are sugars that differ in configuration at only 1 position. • Examples of epimers : – D-glucose & D-galactose (epimeric at C4) – D-glucose & D-mannose (epimeric at C2) 35
  • 37. Enantiomers 1. Monosaccharides contain one or more asymmetric C- atoms: get D- and L-forms, where D- and L- designate absolute configuration 2. D-form: -OH group is attached to the right of the asymmetric carbon 3. L-form: -OH group is attached to the left of the asymmetric carbon 4. If there is more than one chiral C-atom: absolute configuration of chiral C furthest away from carbonyl group determines whether D- or L- Relations among….. 37
  • 39. Sugars Monosachrides Ribose: • Is an aldopentose that, in its open chain form, has an aldehyde functional group at one end • Ribose exists in an equilibrium among 5 forms: – the linear form and – either of the two ring forms: alpha- or beta- ribofuranose, with a 5-membered ring, and alpha- or beta-ribopyranose 39
  • 40. 40 • The ribose β-D-ribofuranose forms part of the backbone of RNA. • It is related to deoxyribose, which is found in DNA
  • 41. Uses: • D-ribose is often marketed as a supplement for bodybuilders, for recovery or increasing muscle mass in healthy people. • D-ribose has also been used to reduce fatigue in fibromyalgia. 41 Sugars …
  • 42. Xylose • Xylose or wood sugar, is an aldopentose -- a monosaccharide. • Xylose is found in straw, oat hulls and in most woods. • In animal medicine, xylose is used to test for malabsorption (if 25 g po of D-xylose is given to normal patients 4.5 g in 5 hrs will be excreted in the urine ) . 42 Sugars …
  • 44. Mannose • Sugar monomer of the aldohexose series of carbohydrates. • Mannose is a C-2 epimer of glucose. • Mannose commonly exists as two different sized rings, the pyranose form and the furanose form. • Mannose is widely distributed in nature in the form of anhydride-like condensation products termed mannosans 44 Sugars…
  • 45. • Sugar extract from the sap is extracted by making a cut in the bark Fraxinus ornus 45 Fraxinus ornus Sugars…
  • 46. Galactose • Galactose is a type of sugar which is less sweet than glucose. • It is a C-4 epimer of glucose • It is considered a nutritive sweetener because it has food energy 46 Sugars …
  • 47. • Galactose is found in dairy products, tomatoes, sugar beets, etc • It is also synthesized by the body, where it forms part of glycolipids and glycoproteins in several tissues 47 Sugars…
  • 48. Sugars… D-glucose (dextrose , α-D-glucopyranose, grape sugar) • C6H12O6 , It is found in honey and the juices of many fruits • Glucose is made industrially by the hydrolysis of starch under the influence of dilute acid. 48
  • 49. 49 • Glucose is stored as a polymer, in plants as starch and in animals as glycogen. • Many crops can be used as the source of starch. • Maize, rice, wheat, cassava, are all used in various parts of the world Sugars…
  • 50. 50 Cassava, Beta vulgaris, sugar beet Sugars…
  • 51. Uses – As sweetener ….In the preparation of syrups and elixirs – For coating tablets and as tablet binder – It is used as a nutrient in food and dextrose injection in replacement therapy usually at 5% and 10%. 51 Sugars…
  • 52. Sugars… – It is used as a fluid and nutrient replenisher. – It also present in anticoagulant citrate phosphate dextrose solution. – Used commercially in the manufacture of candy, carbonated beverages, ice cream,etc. 52
  • 54. Sugars… D-fructose (levulose) • Is present practically in all fruits and honey • Commercially, fructose is frequently derived from sugar cane, sugar beets, and corn. 54
  • 55. Sugars… • It is the sweetest of all naturally occurring carbohydrates. • In general, fructose is regarded as being 1.73 times as sweet as sucrose. • However, it is the 6-membered ring form of fructose that is sweeter 55
  • 56. Crude drug containing sugar Honey • Honey is thick, syrupy, translucent liquid when fresh but becomes opaque and granular through time due to crystallization of glucose • It is pale yellow to reddish brown • It posses sweet taste and usually pleasant flavor (odor & taste) that varies depending on the nectar source 56 Sugars…
  • 57. Chemical constituents: • Honey contains chiefly D-glucose (30-40%), fructose (40-50%) and small amounts of sucrose (0.1-10%), pollen grains, and volatile oil 57 Sugars…
  • 58. Medicinal uses and health effects of honey • Honey has antibacterial activity • Diabetic ulcers when the patient cannot use other topical antibiotics • Mild forms of conjunctivitis • Due to its antiseptic properties, it can be taken orally by Pharyngitis and Laryngitis sufferers, in order to soothe them • Mild laxative (for constipation) • Sedative (for mild insomnia) 58 Sugars…
  • 59. Cymarose and Digitoxose – Cymarose is closely resembles to digitoxose in behaviour and is considered to be a methylether of digitoxose. – Cymarose are obtained on hydrolysis of the glucosides cymarin (from the root of apocyanum) 59 Sugars …
  • 60. Digitoxose, (C 6 H 12 O 4) • The leaves of Digitalis purpurea contain apparently more than five glycosides which form the active constituents of digitalis • Digitoxin the most active principle, is insoluble in water; on hydrolysis it forms digitoxigenin and a sugar, digitoxose. 60 Sugars and…
  • 61. Disaccharides Sucrose (saccharum, sugar or table sugar) • It is O-β-D- fructofuranosyl-(2 ↔ 1)-α-D-glucopyranose • Sucrose is a disaccharide composed of D-glucose and D-fructose. • It is a the most abundant disaccharide and the main form in which carbohydrates are transported in plant. 61 Sugars and…
  • 62. Sugars… • Important commercial sources of sucrose are – Sugar cane: Saccharum officinarum – Sugar beet: Beta vulgaris 62
  • 63. Sugars… • When sucrose is hydrolyzed by dilute acid solution, it produces equal amounts of D-glucose and D- fructose. • This mixture is commonly known as invert sugar. 63
  • 64. Sugars… Uses – As sweetener – In the preparation of syrups and elixirs – For coating tablets and as tablet binder – For manufacturing lozenges and pastilles – As a demulcent and as a nutrient – Act as bacteriostatic agent and preservative if used in high concentration 64
  • 65. Lactose, milk sugar • Lactose is a disaccharide composed of D-galactose and D-glucose units • It found most notably in milk .Lactose makes up around 2–8% of milk (by weight) • It is only faintly sweet, and its principal use is as a diluent in tablet formulations 65 Sugars…
  • 66. Polysaccharides Polysaccharides • They consist of repeat units of monosaccharides or their derivatives. • They are colourless and tasteless. • They are concerned with two important functions - structural and storage of energy. 66
  • 67. Starch • Starch for medicinal and pharmaceutical use consists of polysaccharide carbohydrate occurring as discrete granules in: – The mature grain of maize or corn (Zea mays) – The mature grain of wheat (Triticum aestivum) – The mature grain of rice (Oryza sativa) – Tubers of potato (Solanum tuberosum) 67 Polysaccharides…
  • 69. Character: • Starch occurs as granules with different shapes, patterns and size (diameter = 2-100 μm) depending on the botanical source. – Wheat starch: 2-23 μm – Corn starch: 25-32 μm – Potato starch 30-100 μm • Starch granules are insoluble in water 69 Polysaccharides…
  • 70. Chemical composition: Starch granules are composed of two glucans known as amylose and amylopectin Characteristics Amylose Amylopectin Average amount 20-25% 75-80% Average no of glucose units 250-300 More than 1000 Structure Linear non- branching Linear branching Connectivity of glucose units Exclusively by α(1→4) linkage α(1→4) linkage in the main chain and α(1→6) linkage at branching points Water solubility Water soluble Water insoluble but swells in water Color with iodine Deep-blue Blue-violet or purple 70 Polysaccharides…
  • 71. Amylose – a straight chain structure formed by 1,4 glycosidic bonds between α-D-glucose molecules. H O OH H OH H OH CH2OH H O H H OH H OH CH2OH H O H H H O O H OH H OH CH2OH H H H O H OH H OH CH2OH H OH H H O O H OH H OH CH2OH H O H 1 6 5 4 3 1 2 amylose Structure of Amylose Fraction of Starch 71 Polysaccharides…
  • 72. Amylopectin-a glucose polymer with mainly α -(14) linkages, but it also has branches formed by α -(16) linkages. H O OH H OH H OH CH2OH H O H H OH H OH CH2OH H O H H H O O H OH H OH CH2 H H H O H OH H OH CH2OH H OH H H O O H OH H OH CH2OH H O H O 1 4 6 H O H OH H OH CH2OH H H H O H OH H OH CH2OH H H O 1 OH 3 4 5 2 amylopectin Structure of Amylopectin Fraction of Starch 72 Branch Polysaccharides…
  • 73. Medicinal uses: – As binder (because of amylose…. Water soluble) – As disintegrants (because of amylopectin.. Swell in water) – As tablet filler – As absorbent in dusting powders 73 Polysaccharides…
  • 74. Dextran • Dextran contains from 200-400 glucose units with predominant linkage is α(1,6) • 3.5 or 10% solution dextran is used for plasma volume expansion in the treatment of shock, means of parenteral nutrition • Dextran is also used in lubricant eye drops designed to minimize discomfort from contact lens 74 Polysaccharides…
  • 75. Cellulose • The β-glucose molecules are joined together forming β-(1,4) glycosidic linkages. • The glucose units are linked into straight chains each 100-1000 units long. • Weak hydrogen bonds form between parallel chains binding them into cellulose microfibrils. • Cellulose microfibrils arrange themselves into thicker bundles called microfibrils…….fibres 75 Polysaccharides…
  • 76. • The cellulose fibres are often “glued” together by other compounds such as hemicelluloses and calcium pectate ……..plant cell walls. • Cellulose is the principal structural element of higher plant cell walls • Cellulose is commercially obtained from: – Hair of the seed of cotton plant – Wood 76 Polysaccharides…
  • 79. 79
  • 81. Use • Surgical dressing • For preparing absorbent gauze • Powdered cellulose is used as tablet diluent and disintegrants 81 Polysaccharides…
  • 82. Cellulose Cellulose acetate phtalate (CAP) - entricoating tablets Hydroxypropylmethylcellulose - suspending agent - thickening agent Ethylcellulose - tablet binder Methylcellulose - bulk laxative - suspending agent - Artificial tear + for xerophtalmia + contact lens Sodium carbonylmethylcellulose (CMC) - thickening agent - bulk laxative Cellulose is extensively modified; 82 Polysaccharides…
  • 83. Glycogen • Is a polysaccharide of glucose which functions as the secondary short term energy storage in animal cells • It is made primarily by the liver and the muscle, but can also be made by the brain and stomach • Glycogen is the analogue of starch commonly referred to as animal starch 83 Polysaccharides…
  • 84. Gums and mucilage Consists of Ca, Mg and K salts of polyuronoides that are hydrolyzed by boiling with acids to monosaccharide and uronic acid or galactouronic acid 84 Polysaccharides…
  • 85. • Gums are considered to be pathological products formed upon injury of the plant or owing to unfavorable conditions such as drought • The formation of gums is known as gummosis which involves the break down of cell walls and thus it is an extracellular process • Mucilages are normal products of metabolism, formed with in cells (intracellular formation) 85 Polysaccharides…
  • 86. • Mucilages usually serve as storage materials, water- storage reservoirs, or may provide protection for germinating seeds • Insoluble in alcohol and in most organic solvents but soluble in water yielding viscous, usually adhesive colloidal solutions 86 Polysaccharides…
  • 87. Pharmaceutically important gums • Acacia gum is the dried gummy exudate obtained from the stem and branches of Acacia senegal and some related species like Acacia arabica • Acacia gum contains chiefly arabin (mixture of calcium, magnesium and potassium salts of arabic acid) • On hydrolysis arabic acid yields L-rhamnose, L- arabinose, D-galactose and D-glucuronic acid 87 Polysaccharides…
  • 89. Acacia gum is used: • As demulcent (added in formulations for cough, diarrhea and throat problems) • As emollient (to cover burns, sore nipples etc) • As emulsifying agent (for oil in water emulsions) • As binder in tablets especially in lozenges. • Commercially as adhesive 89 Polysaccharides…
  • 90. Gum tragacanth • Tragacanth is the dried gummy exudate obtained from the stems of Astragalus gummifer and other related species • Gum tragacanth contains targacanthin and bassorin – Targacanthin is the water soluble portion and is 1/3 of the mass – Bassorin is the water insoluble portion and is 2/3 of the mass…….Bassorin swells to from a gel 90 Polysaccharides…
  • 92. • Gum tragacanth is used – As suspending and emulsifying agent – As binder in pills and tablets – As a bulk laxative – Gum tragacanth is resistant to acid hydrolysis so it is preferred in acidic preparations. 92 Polysaccharides…
  • 93. Pharmaceutically important mucilages Agar • Agar is the dried, acidic, hydrophilic colloidal polysaccharide complex extracted from different red algae species such as: – Gelidium cartilagineum – Gracilaria confervoides • Agar is composed of acidic polysaccharides that could be resolved into two fractions: – Agarose is the gelling fraction – Agaropectin is the non-gelling fraction 93 Polysaccharides…
  • 95. Agar is used • As suspending and emulsifying agent • As gelling agent for suppositories • As tablet filler and disintegrant • For the treatment chronic constipation (bulk laxative) • For the preparation of culture media (1% solution) 95 Polysaccharides…
  • 96. Algin (Sodium alginate) • Algin is a polysaccharide extracted from different strains of brown seaweed by the use of dilute alkali • It is chiefly obtained from Macrocystis pyrifera • Sodium alginate yields D-mannuronic acid and L- glucuronic acid • Algin is readily water-soluble 96 Polysaccharides…
  • 98. Algin is used • As suspending and emulsifying agent • As thickening agent • As tablet binder • Food (ice cream) • Commercially it s widely used in cosmetics and textile 98 Polysaccharides…
  • 99. Pectin • Cell walls of higher plants • Largely a linear polymer of polygalacturonic acid with varying degrees of methyl esterification. 99 Polysaccharides…
  • 100. Use • as gelling agent • Thickeners • Laxative • used in throat lozenges as a demulcent 100 Polysaccharides…
  • 101. Chitin • Chitin is the second most abundant carbohydrate polymer • It is modified polysaccharide that contains nitrogen;………..units of N-acetylglucosamine • Cellulose with one hydroxyl group on each monomer replaced with an acetyl amine group. • Present in the cell wall of fungi and in the exoskeletons of crustaceans, insects and spiders 101 Polysaccharides…
  • 103. • Chitin is used commercially in coatings (extends the shelf life of fruits and meats) • Chitin's flexibility and strength make it favorable as surgical thread 103 Polysaccharides…
  • 104. Plant acids such as citric, lactic, and tartaric acid find wide application in the formulation of food and medicine. Citric acid Weak organic acid with the formula C6H8O7 104 Sugar related compounds
  • 105. Sugar related… – It is a tricarbixylic acid – First isolated from lemon juice – Present in many fruits and plants – Commercially obtained from lemons, pineapples – Colorless, odorless, translucent crystal and soluble in water and alcohol 105
  • 106. Uses – Useful in buffering system – Used as an acidulant in effervescent formulation – An ingredient in anticoagulant, citrate phosphate dextrose solution 106 Sugar related…
  • 107. Lactic acid – Colorless or yellowish, odorless, syrupy liquid – Miscible with water, alcohol and ether Uses: – As acidulant especially in infant feeding formulas – Sodium lactate injection is a fluid and electrolyte replenisher – Calcium lactate - a calcium replenisher – In topical preparations and cosmetics to adjust acidity and for its disinfectant and keratolytic properties. 107 Sugar related…
  • 109. Tartaric acid – Dicarboxylic acid byproduct of wine industry – Freely soluble in water – Used as a substitute for citric acid in buffer system in effervescent formulations 109 Sugar related…
  • 110. Mannitol (D-mannitol) 110 • Obtained by the reduction of mannose or by isolation from manna • Manna is the dried saccharine exudate of barks of Fraxinus ornus and contains 50-60% of mannitol Sugar related…
  • 112. • Occurs as white crystalline powders. • Odorless and sweetish taste. • Mannitol is not absorbed in GIT……When administered parentally, it is not metabolized and eliminated by glomerular filtration (80% of 100 in 3 hrs) 112 Sugar related…
  • 113. Medicinal use: • For diagnosis of kidney function • As osmotic diuretic • Also as osmotic laxative for constipation • As sweetener for diabetics 113 Sugar related…
  • 114. Sorbitol (D-glucitol or D-sorbitol) 114 Sugar related… Most sorbitol is made from corn syrup, but it is also found in apples, also occurs in many fruits Sorbitol is an isomer of mannitol
  • 115. • Commercially it is prepared from glucose by chemical or electrolytic reduction • Sorbitol is half as sweet as sucrose and it is not absorbed from the GIT 115 Sugar related…
  • 116. Pharmaceutical use: • Used as osmotic laxative for constipation. • As sweetener for diabetics • It is commonly used in toothpastes, chewing gums 116 Sugar related…
  • 117. Qualitative Test to Detect CHOs • Is concerned with determining the identity of a substance. – Molisch Test- carbohydrates – I2 Test - Cellulose, Starch, Dextrin – Seliwanoff’s Test- Ketose from Aldose – Test for Reducing Sugars (Barfoed’s TestFT ) 117
  • 118. Qualitative test… Molisch test • Aqueous solution of carbohydrate mixed with few drops of Molisch reagent (alpha naphthol) and Conc. H2SO4 was added from sidewall of test tube. • Formation of purple coloured ring at junction indicates presence of carbohydrates. 118
  • 120. Iodine test • It is specific for polysacchrides. • Few drops of Iodine solution is added to aqueous solution of polysaccharide. • Formation of blue colour, which disappears on heating and reappears on cooling, indicates the presence of starch. Qualitative test… 120
  • 122. Barford test • This test is used to distinguish between monosacchride and disacchrides. • Two ml of Barford reagent (Cupric acetate, acetic acid and water) was added to 1 ml aqueous solution of carbohydrates and boil. • Formation of brick red precipitate in 5 minutes indicates presence of monosacchride while in 7 minutes indicates disaccharide. Qualitative test… 122
  • 124. Seliwanoff’s test • This test is used for identification of keto-hexoses or to distinguish between ketoses and aldoses. • To 1 ml aqueous solution of drug, 5 ml of Seliwanoff’s reagent (resorcinol in 6M HCl) was added and boiled. • Formation of cherry red colour in presence of ketose (e.g fructose) due to formation of hydroxyl methyl furfural Qualitative test… 124
  • 126. Fehling solution test • It is generally used for reducing sugars and composed of two solutions, which are mixed in situ. • Fehling solution A composed of 0.5% of copper sulphate whereas Fehling solution B composed of Sodium Potassium Tartarate. Qualitative test… 126
  • 127. • Equal volumes of Fehling A and Fehling B solutions were mixed (1 ml each) and 2 ml of aqueous solution of drug was added followed by boiling for 5-10 minutes on water bath. • Formation of reddish brown coloured precipitate due to formation of Cuprous oxide indicates presence of reducing sugar. 127 Qualitative test…
  • 130. Benedict’s test • It is used for reducing sugars and composed of mainly Copper sulphate and sodium hydroxide. • To the 4 ml of aqueous solution of drug, 1 ml of Benedicts solution was added and heated almost to boiling. • Formation of green, yellow, orange, red or brown colour in order of increasing concentration of simple sugar in the test solution, due to formation of cuprous oxide. Qualitative test… 130