Carbohydrates &

Related
Compounds
⦿ OUTLINE
⦿ General knowledge about
carbohydrates
⦿ Classification of carbohydrates and
related compounds
⦿ Biosynthetic pathway
⦿ Carbohydrate products
⦿ Carbohydrate-containing products
 Definition of carbohydrates
⦿ Polyhydroxy ketones and polyhydroxy
aldehydes containing C, H, & O same
ratio as water (2:1)
⦿ 1st products of photosynthesis
⦿ General formula
› CnH2nOn | Cn(H2O)n | (CH2O)n
 Carbohydrates Utilization

⦿ Carbohydrates are the principal source of energy

for most living organisms.
⦿ The metabolism of carbohydrates also provide a
number of intermediates that are essential in
biosynthetic processes and in the maintenance of
cell.
Classification of Carbohydrates
 Monosaccharides

⚫ classified according to three different

characteristics:
1. placement of its carbonyl group
2. number of carbon atoms it contains
3. its chiral handedness
Placement of carbonyl
# of carbon
Chiral placement
 Monosaccharides

⦿ Simplest and does not yield simpler

carbohydrates upon hydrolysis
⦿ substances with an aldehyde or ketone
substitution product of a polyhydroxy
alcohol
# Name Aldose Ketose
2 Diose Hydroxyacetaldehyde

3 triose glyceraldehyde Dihydroxyacetone

4 tetrose erythrose Erythrulose
5 pentose Arabinose, xylose, ribose Ribulose

6 hexose Glucose, galactose, Fructose

mannose

7 heptose sedoheptose Sedoheptulose

8 octulose D-glycero-D-mannoctulos
e
 Sugars = Monosaccharides

⦿ simplest: Diose
› hydroxyacetaldehyde - not in nature
⦿ Triose (exist in nature)
›glyceraldehyde, dihydroxyacetone
⦿ Tetrose not in the free state
 Sugars = Monosaccharides
⦿ Pentose - hydrolytic products of hemicelluloses,
⦿ Pentoses in cytoplasm not in the free state
› xylose (xylan and arabins) and arabinose
› ribose and deoxyribose (components of
nucleic acids)
 Sugars = monosaccharides

⦿ hexose (16 aldoses and 8 ketoses in the α and

β forms
› in plants, glucose, fructose, mannose and
galactose
› forms that occur in the free state are the D and L
● D - glucose (dextrose)
● D - fructose (levulose)
 Oligosaccharides
⦿ Classified according to the number of
monosaccharides in the structure:
› disaccharide (2)
› trisaccharide (3)
› tetrasaccharide (4)
lactose maltose

sucrose
Stachyose
 BIOSYNTHESIS OF CARBOHYDRATES

⦿ Carbohydrates are products of

photosynthesis, a biologic process that
converts electromagnetic energy into
chemical energy
⦿ General equation:
⦿ 2 H2O + CO2 + light--------------
(CH2O) + H2O + O2
 Photosynthesis

⦿ Involves 2 classes of Reactions:

⦿ 1. Light Reaction- electromagnetic energy to
chemical potential
⦿ 2. Dark Reaction- enzymatic reactions that
utilize energy from the light reaction to fix
carbon dioxide into sugar
Sugars &
sugar-containing
compounds
Monosaccharides
Oligosaccharides
Polysaccharides
Related compounds
 Monosaccharides products

⦿ Dextrose
⦿ Fructose
⦿ Galactose
⦿ Xylose
 Dextrose = glucose

⦿ Aka: D-glucose, blood sugar, grape

sugar, physiologic sugar
⦿ Source: naturally found in grapes
⦿ Commercial source: enzymatic
hydrolysis of starch
⦿ ID test: Moore’s test – (+)caramel
 Uses:

⦿ Nutrient
⦿ Excipient
 Note:
◼ Term DEXTROSE is widely used in the pharmacy,
medicine and in commercial channels
◼ However, Glucose, the accepted scientific name is
employed in the chemical and biochemical literature
◼ Dextrose in the form of liquid glucose is used
commercially in the manufacture of candy,
carbonated beverages, ice cream, bakery products
and in the canning industry
 Dextrose Excipient

⦿ Is a crystalline dextrose monohydrate that

has undergone less rigorous purification
⦿ Agent for pharmaceutical necessity
 Dextrates

⦿ purified mixture of saccharides (not less than

93% dextrose), also prepared by controlled
enzymatic hydrolysis of starch
⦿ Used as sweetening agents, substitutes for
sucrose in syrups; tablet binders & coating agents
 Liquid glucose

⦿ incomplete hydrolysis of starch,

composed primarily of glucose with
dextrins, maltose and water
 Fructose
⦿ Aka: fruit sugar, levulose, Sweetest sugar
⦿ Origin: obtained by the inversion of an
aqueous solution of sucrose & subsequent
separation of fructose from glucose
⦿ Source: fruits, honey, inulin, semen
⦿ ID test: Seliwanoff’s test – (+) red
 Use:

⦿ Food for diabetics

⦿ Ingredient in infant feeding formula
⦿ Nutrient (inj)
 High- Fructose Sweeteners

⦿ Prepared by controlled enzymatic

isomerization of glucose
› Glu→Fru
› enzyme used: Glucose Isomerase
● From Streptomyces species
⦿ Ex. Fructose corn syrups
 Xylose

⦿ Synonym: D - xylose, wood sugar

⦿ Origin: obtained by boiling corn cobs,
straw or similar materials with dilute
acid to hydrolyze xylan polymer
⦿ Use: diagnostic aid in intestinal
malabsorption
⦿ Rx Products: Xylo- Pfan
⦿ Notes: absorbed in the small intestine but
not metabolized by mammalian enzymes
 oligosaccharides

⦿ Disaccharides
⦿ Trisaccharides
⦿ tetrasaccharides
 Sucrose (Glu+Fru)

⦿ Aka saccharum, table sugar, beet sugar,

cane sugar
⦿ Most abundant sugar
⦿ Only sugar found in free state
⦿ First sugar formed in synthesis
⦿ Bacteriostatic = 85%
⦿ Saccharum officinarum – sugar cane
⦿ Beta vulgaris – sugar beet
⦿ Acer saccharum - maple
 Sucrose Production
⦿ Juice is obtained by crushing the stems between
a series of heavy iron rollers
⦿ It is boiled with lime to neutralize the plant
acids which change the sucrose to invert sugar
and to coagulate albumins
⦿ Molasses- used in foods, prepared animal foods
and in the manufacture of ethyl alcohol
 Maltose (Glu + Glu)

⦿ Sugar from grains (barley)

⦿ Product of complete hydrolysis of starch
⦿ Product of germination (diastatic fermentation)
 Lactose (Glu + Gal)

⦿ Aka milk sugar

⦿ Souce: cow’s milk (Bos taurus)
⦿ sugar crystallized from whey
⦿ Sp grav. 1.029 – 1.034
⦿ Use: nutrient and pharmaceutical
necessity (tablet diluent)
⦿ Infant food nutrient, intestinal microflora
establisher (Lactobacillus)
Milk-derived products
Differentiate
Condensed milk
⦿ Prepared by partial
evaporation of milk in a
vacuum & consequent
sterilization in hermetically
sealed containers by
autoclaving
Malted milk
⦿ Is prepared by evaporating
milk with an extract of malt
⦿ Low heat & vacuum are
used to prevent the
destruction of enzymes
 Lactulose
⦿ semi synthetic sugar prepared by alkaline
rearrangement of lactose (fructose and galactose)
⦿ poorly absorbed and remains unchanged up to
colon where bacteria metabolize the sugar to
acetic acid and lactic acid
⦿ lactic acid and acetic acid causes laxative effect
⦿ use: chronic constipation,
decreases blood ammonia
concentration in portal
systemic encephalopathy
⦿ Rx Products: Cephulac
and Chronulac
 Polysaccharides
⦿ Can either be:
› Homoglycan – same sugar units (starch,
cellulose)
› Heteroglycan – different sugar units
(gums, mucilage)
 Homoglycans

⦿ Starch
⦿ Inulin
⦿ Dextran
⦿ Cellulose
⦿ Chitin
 Starch (glucosan)

⦿ Storage form of energy in plants

⦿ Made up of 2 components:
○ Amylose
○ Amylopectin
⦿ Source:
› Oryza sativa
› Mannihot esculenta
› Ipomoea batata
› Solanum tuberosum
› Triticum aestevium
› Zea mays
⦿ Use: pharmaceutical aid, antidote for I2
poisoning, nutrient
Difference
Amylose Amylopectin
⦿ Straight chain ⦿ Branched
⦿ a-1,4 ⦿ a-1,4; a-1,6
⦿ More water soluble ⦿ Less water soluble
⦿ + I2 = deep blue ⦿ + I2 = blue
⦿ 25% violet/purple
⦿ 75%
Starch hydrolysis products

⦿ Dextrin - partial hydrolysis

⦿ Maltotriose – intermediate hydrolysis
⦿ Liq glucose – incomplete hydrolysis
⦿ Maltose – complete hydrolysis
⦿ Dextrose – hydrolysis of maltose
 Hydrolyzing enzymes (amylases)

⦿ Ptyalin – mouth
⦿ Amylopsin – pancreas
⦿ a-amylase – random splitting of a-1,4 glycosidic
link
⦿ B-amylase – removes maltose units from non
reducing ends
⦿ a-glucosidase – a-1,6 link
 Other products of starch
⦿ Pregelatinized starch – chemically or mechanically processed
to rupture all or part of the granules in the presence of water
⦿ Na starch glycolate – disintegrant
⦿ Hetastarch – 90% amylopectin; plasma expander
⦿ Dextran- from sucrose by action of Leuconostoc
mesenteroides; 10% solution is employed to reduce blood
viscosity (may interfere with clotting time - increased)
 Inulin (fructosan)

⦿ Ingredient in culture media

⦿ Evaluating tool for renal function
 Cellulose – structural polysaccharide

⦿ PURIFIED COTTON
› Synonym: Cotton wool, Lana Gossypii,
Bulak(Tag.)
› Origin: hair of the seeds of Gossypium
hirsutum or other species of Gossypium
(Malvaceae) that is freed from adhering
impurities deprived of fatty matter.
Bleached and sterilized in its final container
⦿ Use: surgical dressing, mechanical
protectant, textiles, manufacture of
explosives
Cotton
 Chemically modified fibers

⦿ Regenerated cellulose (rayon , viscose)

⦿ Oxidized cellulose
⦿ Cellulose ethers
› Methylcellulose
› Sodium carboxymethylcellulose
⦿ Pyroxylin
 Products of Cellulose

⦿ Powdered cellulose
› self binding tablet diluent, disintegrating agent
⦿ microcrystalline cellulose ( purified partially
depolymerized cellulose)
› diluent
⦿ purified rayon (fibrous form of the bleached
regenerate cellulose)
› surgical aid; nmt 1.25% of titanium dioxide
Cellulose derivatives

› methylcellulose - bulk laxative & suspending

agent; topical protectants as artificial tears
› Sodium carboxylmethylcellulose – antacid
› ethylcelllulose - tablet binder, film coating;
› hydroxyethylcellulose – ing. In artificial tears &
thickening agents
› Hydroxypropylcellulose- stabilizer; thickening agent;
binder & film coating in tablet formulations
› pyroxylin or soluble guncotton - prep. of collodion,
topical protectant; mixture of nitric and sulfuric acid on
cotton
Products of metablism of sugars
⦿ Oxidative ⦿ Reductive
› Juice › Sugar alcohols
› Plant acids
› Alcohol (ethanol)
 Cherry Juice NF XVI

⦿ Synonym: succus cerasi, cherry

⦿ Origin: expressed liquid from the
fresh ripe fruit of Prunus cerasus
(Rosaceae)
⦿ Constituent: nlt 1% malic acid
⦿ Use: ingredient in the
preparation of cherry syrup, a
flavored vehicle to disguise
pharmaceutical mixtures
(acidulous nature)
⦿ Cherry Juice NF 6
Raspberry NF 6
⦿ Juice from the fresh
ripe fruits of Rubus
idaeus or R.
strigosus (Rosaceae)
› 1.5% citric acid
⦿ Raspberry Juice
USP 18
Prune NF 5 (1926)
⦿ the partially dried
ripe fruit of Prunus
domestica
(Rosaceae)
⦿ when used
pharmaceutically,
the fruit must
contain 30 - 35%
natural moisture
Lemon USP VII (1851)

( Limonis Succus )
juice from the fresh
fruit of Citrus limon
(Rutaceae)
Apple NF V (Succus Pomorun)
⦿ Freshly expressed juice
of sound, ripe, sour
apples of the cultivated
variety Pyrus malus
(Rosaceae)
⦿ malic acid NF 18
 Organic Acids

⦿ Lactic, citric, and tartaric acids are used as

acidulants or components of buffer systems to
control acidity
⦿ less irritating
⦿ non - toxic
 Citric acid

⦿ Tricarboxylic acid
⦿ Isolated as crystals from lemon juice(Scheele,
1784)
⦿ obtained commercially from lemons, limes,
pineapple or by fermentation of sucrose
⦿ use in buffer systems
⦿ acidulant in effervescent formulations
⦿ ingredient in systemic alkalinizers and
anticoagulant preparations
⦿ Acidulant effervescent formulations
⦿ Ingredients in potassium citrate & citric acid
solution etc.
 Lactic acid USP 23

⦿ Used as acidulant esp. infant feeding formulas

⦿ electrolyte replenisher(sodium lactate injection)
for the treatment of metabolic acidosis; calcium
salt as calcium replenisher
 Tartaric acid NF 18

⦿ Dicarboxylic acid
⦿ by-product of wine industry
⦿ used as substitute for citric acid in buffer systems
and effervescent formulations
 Fumaric Acid NF 18

⦿ ferrous fumarate
⦿ hematinic agent
 Tamarind NF 5

⦿ Synonym: Tamarindo, sampalok(Tag)

⦿ Origin: The partially dried - up fruit deprived of
brittle outer pericarp of Tamarindus indica
(Fabaceae) preserved in syrup or sugar
⦿ Constituent: sugar with tartaric , malic and citric
acid
⦿ Uses: refrigerant, laxative or purgative
 Alcohol

⦿ Ethanol, ethyl alcohol- mixture of

alcohol and water
⦿ Natural Processes to produce alcohol
› fermentation - % alcohol does not exceed
14%
⦿ distillation - 40 - 55% alcohol
› brandy – wine (fermented grape juice) as
medicinally as mild stimulant, tonic
› whiskey - fermented malted grain (CNS
depressant)
› rhum - fermented molasses(CNS
depressant)
› beer- fermented grain
⦿ containing nlt 92.3% by weight or 94.9% by
volume
⦿ 70% w/v solution is used as local anti - infective
⦿ 5 - 10% alcohol with dextrose(5%) - IV infusion
to increase caloric intake and replenish fluids
⦿ dilute alcohol (48.4 - 49.5% by volume used as
solvent
Brandy NF XI

⦿ alcoholic liquid obtained from

the distillation of the fermented
juice of sound ripe grapes
(Vitis vinifera, Fam Vitaceae)
and containing nlt 48% and
nmt 54% by volume of ethyl
alcohol at 15.560
⦿ central depressant
 Sherry Wine NF XI

⦿ alcoholic liquid obtained by fermentating the

juice of sound ripe grapes (Vitis vinifera, Fa.
Vitaceae) fortifying with brandy and containing
nlt 17% and nmt 24% ethyl alcohol at 15.560

⦿ pharmaceutical necessity, ingredient of beef, iron

and wine
 Mannitol USP 23

⦿ Synonym: Manna ash, manna

⦿ Origin: dried exudate from the stem of Fraxinus
ornus (Oleaceae)
⦿ Constituents:
⦿ mannitol (can be obtained by reduction of
mannose)
⦿ Fraxin, mannose, resins, mucilages, ash
⦿ Use:
⦿ osmotic diuretic, laxative,
diabetic food,
⦿ bacteriological culture
media
⦿ diagnostic aid
 Sorbitol NF 18

⦿ Synonym: Mountain ash berries

⦿ Origin: ripe berries of Sorbus aucuparia L.
(Rosaceae)
› synthetically by hydrogenation of glucose
⦿ Constituents: sorbitol ( half as sweet as
sucrose)
⦿ Use: humectant
› ingredient in toothpaste, chewing gums and
other dietetic preparations
› sweetener in non-caloric beverages
(osmotic laxative)
› with mannitol used as an urologic irrigant
 Xylitol

⦿ Product of reductive metabolism of xylose

⦿ Found in chewing gums
 Polysaccharides

⦿ Homoglycan
⦿ Heteroglycan- different sugar units
 Heteroglycans

⦿ Gums
⦿ Mucilage
⦿ exudates
 Gums & mucilage

⦿ Natural plant hydrocolloids that may be classified

as anionic or non-ionic polysaccharides
⦿ Produced by plants as a protectant after injury
⦿ Upon hydrolysis, yield arabinose, galactose,
glucose, mannose, xylose, and other uronic acid
derivatives
⦿ Gums – pathological product
› Water soluble
⦿ Mucilage – physiological product
› Water insoluble = slimy masses
 Sources:

⦿ Tree exudates – acacia, karaya, tragacanth

⦿ Marine gums – agar, algin, carrageenan
⦿ Seed gums – guar, locust bean
⦿ Microbial gums - xanthan
⦿ Plant extracts - pectin
Tree exudates
 Acacia
⦿ Synonym: gum arabic, galam gum, gummi
mimosae
⦿ Origin: dried gummy exudate from the stems and
branches of Acacia senegal (Fabaceae)
⦿ Constituents: arabin (Ca+2, Mg+2, K+ salts of
arabic acid)
⦿ Uses: suspending agent, demulcent, emollient,
adhesive, binder (tablet formulation
⦿ Notes: gum soluble in water and remains in
solution in alcohol
⦿ low viscosity, stable from pH 2 - 10 (good
emulsifier)
⦿ Insoluble to alcohol
⦿ + Bi =
⦿ + Fe =
 Synonyms:

⦿ Acacia gum, Acacia vera, Egyptian thorn,

Gummi africanum, Gum Senegal, Gummae
mimosae, Kher, Sudan gum arabic, Somali gum,
yellow thorn, Indian gum and Gum arabic
 Biological Source:

⦿ dried gummy exudate obtained from the stems

and branches of Acacia senegal (L.) Willd or
other African species of Acacia

⦿ In India: Acacia arabica

⦿ Family: Leguminosae
 Geographical Source:

⦿ Acacia senegal: drier parts of Anglo- Egyptian

Sudan and the northern Sahara
⦿ vast area from Senegal to the Red Sea and to
eastern India
⦿ extends to Nigeria, Uganda, Kenya, Tanzania,
southern Africa
⦿ extensively found in Arabia, Kordofan

⦿ SUDAN: major producer

 Cultivation and Collection

⦿ Acacia is a thorny tree up to 6m in height

⦿ cultivated by sowing the seeds in the poor,
exhausted soil containing no minerals, but trees
also grow by seed-dispersal
⦿ gum is collected by natives from 6 to 8 yrs old
trees, twice a year in dry weather in November or
in Feb- March
Colour Tears are usually white, pale- yellow
and sometimes creamish -brown to red
in colour. The powder has off white,
pale-yellow or light- brown in
appearance

Odor odourless

Taste Bland & mucilaginous

Shape & Size Mostly spheroidal or ovoid in shape

and having a diameter of about 2.5- 3.0
cm
 History

⦿ brought from the Gulf of Aden to Egypt in the

17th B.C and in the works of Theophrastus it is
spoken of as a product of Upper Egypt
⦿ The west african product was imported by the
Portuguese in the 15th century
⦿ Gum Arabic Company produces 40,000 tonnes
per annum
 Chemical Constituents

⦿ ARABIN; mixture of Ca, Mg & K salts of arabic

acid
⦿ Arabic acid: branched polysaccharide that yields
L- arabinose, D- galactose, D- glucuronic acid
and L- rhamnose on hydrolysis
⦿ contains 12-15% water;
⦿ enzymes: oxidases; peroxidases & pectinases
 Chemical Tests:

⦿ Lead acetate test: heavy white ppt

⦿ Reducing sugar tests: (dilute HCl & Fehling’s
soln) brick red ppt of cuprous oxide
⦿ Blue coloration due to enzyme: (benzidine in
alcohol & H2O2 blue color (oxidases enzyme)
⦿ Borax Test: stiff translucent mass on treatment
with borax
⦿ Specific test: 10% aqueous sol’n with dilute lead
acetate (NO ppt) distinction from Agar and
Tragacanth; NO color change with iodine soln
(distinction from starch and dextrin); NO bluish-
black colour FeCl3 soln (distinction from
tannins)
 Uses:
⦿ Mucilage: demulcent
⦿ emulsifying agent and thickening agent
⦿ binding agent for tablets ex. cough lozenges
⦿ use ‘granulation’ process for tablet
manufacturing
⦿ gum of choice: compatible with plant
hydrocolloids, starches, carbohydrates and
proteins
⦿ micro-encapsulation: combination w/ gelatin
⦿ as colloidal stabilizer; used in candy
⦿ administered IV as haemodialysis
⦿ ink adhesives; binding medium for marbling
colours
 Toxicology
⦿ Non toxic when ingested
⦿ gum & powdered forms; allergic rxn (respiratory
problems & skin lesions)
⦿ has peroxidase enzyme: can be destroyed by heat ( if
not inactivated, can from colored complexes with
amines, phenols and enhances the product destruction
of pharmaceutical products– alkaloids & vitamins)
⦿ reduces antibacterial effectiveness of
methyl-p-hydroxybenzoate against
Pseudomonas aeruginosa by providing barrier
protection to microbial cell
⦿ trypsin inhibitor
Marketed Product
Acacia
 Ghatti gum

⦿ Substitute for acacia

⦿ Aka Indian gum
⦿ dried exudate from Anogeissus latifolia
(Combretaceae)
⦿ gum is branched
⦿ readily forms dispersion with cold water which is
more viscous than acacia
 Tragacanth

⦿ Synonym: gum tragacanth, goat’s thorn, gum

dragon, Syrian tragacanth, hog gum
⦿ Origin: dried gummy exudate from Astragalus
gummifer(Fabaceae- Leguminosae)
⦿ Constituents:
› tragacanthin - (30%) water soluble
› bassorin(60 - 70%) - swells in water
⦿ Occurrence:
› vermiform tragacanth(worm- like),
› tragacanth sorts or tears,
› ribbon gum
› flake gum - due to transverse incisions
⦿ Use:
Tragacanth gum
 Biological Source:

⦿ Air dried gummy exudates, flowing naturally or

obtained by incision, from the stems and
branches of Astragalus gummifer Labill and
certain other species of Astragalus, belonging to
family of Leguminosae
 Geographical source:

⦿ Abundantly found in the mountainous region of

Turkey, Syria, Iran, Iraq and the former USSR

⦿ VARIETIES:
⦿ Persian tragacanth
⦿ Syrmania or Anatolian tragacanth (Iran &
Turkey)
Species Geographical Dist.
A. gummifer Anatolia & Syria

A. kurdics Northern Iraq, Turkey, Syria

A. brachalyx Western and South Western

Iran
A. eriostylus Southern west Iran
 Cultivation, Collection and
Preparation
⦿ Grow an altitude of 1,000- 3,000 m
⦿ shrubs are very thorny; compound leaves has a
stout, sharply pointed rachis
⦿ plants are tapped in the second year
⦿ obtain by incision
⦿ GRADED as RIBBONS & FLAKES
⦿ best grades form the official drug
⦿ lower grades are used in the food, textile and
other industries
 Grades of Tragacanth
Grade Description
Ribbon No. 1 Fine flat druggists’ ribbon
No. 2 White flat druggists’ ribbon
No. 3 Light- cream curly ribbon
No. 4 Mid- cream flat ribbon
No. 5 Pinkish mixed ribbon
Flake No. 26 Mid- cream thin flake
No. 27 Amber thick flake
No. 28 Amber-brown thick flake
No. 55 Reddish- brown mixed hoggy flake
Colour The flakes are white or pale
yellowish- white
Odour odourless

Taste mucilaginous

Shape and size Tragacanth occurs in the form of

ribbon or flakes. 25x12x2 mm in
size
Appearance Gum is horny, translucent w/
transverse & longitudinal ridges,
fracture is short
 Chemical Constituent:
⦿ Tragacanthin- water soluble (colloidal
solution)
⦿ Bassorin- water insoluble (swelled up in water
to form gel)
⦿ Both are not alcohol soluble
⦿ may be separated by simple filtration of very
dilute mucilage of tragacanth
⦿ 1. Tragacanthic acid galactose, xylose,
galacturonic acid
⦿ 2. Neutral polysaccharide galactose &
arabinose
⦿ 3. steroidal glycoside
 Chemical Tests:
⦿ Aqueous solution of tragacanth on boiloing with
conc. HCl does NOT develop a red colour.
⦿ It does NOT produce red colour with ruthenium
red solution.
⦿ Tragacanth solution is boiled with few gtts of
FeCl3, it produces deep-yellow ppt
⦿ It gives a heavy ppt. with lead acetate.
⦿ When tragacanth and precipitated copper oxide
are made to dissolve in conc. NH4OH, it yields a
meager ppt.
 Uses:
⦿ Demulcent in cough and cold preparations and to
manage diarrhea
⦿ emollient in cosmetics
⦿ Thickening, suspending and emulsifying agent
⦿ mucilage of tragacanth: as binding agent & pill
excipient
⦿ powder as an adhesive
⦿ ing. In lotions and spermicidal jellies
⦿ inhibit the growth of cancer cells in vitro and in
vivo
 Adulterant & Substitutes:

⦿ Hog tragacanth is used in textile industry and

manufacture in pickles

⦿ Adulterant: citral gum

⦿ Substitute: karaya gum

 Toxicology

⦿ recognized as safe (GRAS) inb the US for food

use
⦿ no adverse effects in man as dietary supplement
⦿ Highly susceptible to bacterial degradation
(enterobacteria)
⦿ cross sensitivity to the asthma – induced effects
of quillaja bark
 Karaya gum
⦿ Synonym: Sterculia gum, Indian tragacanth
⦿ Origin: dried gummy exudate from Sterculia
urens, S. villosa, S.tragacantha (Sterculiaceae)
⦿ Has fetid odor
› Movicol – Frangula & Sterculia
⦿ Constituents: gum is an acetylated branched
heteropolysaccharide with the main chain
(galacturonic acid and rhamnopyranose) with
side chain (galacturonic acid)
⦿ Use: bulk laxative, emulsifying agent, suspending
agent, dental adhesives
⦿ Notes:least soluble of the exuded gums (absorbs
water several times its bulk, forming a
discontinuous type of mucilage
 Synonyms

⦿ Indian tragacanth, sterculia gum, karaya gum,

bassora tragacanth, kadaya, mucara, kadira,
katila, kullo
 Biological Source

⦿ It is a dried, gummy exudates obtained from

the tree Sterculia urens (Roxburgh); Sterculia
villosa (Roxburgh), Sterculia tragacantha
(Lindley) or other species of Sterculia, belonging
to family Sterculiaceae
 Collection and Preparation
⦿ obtained from Sterculia species by making
incisions and, thereafter, collecting the plant
exudates usually after a gap of 24 h
⦿ hand picked: gums (tears)
⦿ tapped during the dry season Mar- June
⦿ Purified gum in 2 varieties:
⦿ Granular or Crystal : particle size between 6-30
mesh
⦿ Powdered Gum: 150 mesh
 Morphology

Colour White, pink or brown in color

Odor Slight odor resembling acetic

acid, fetid
Taste Bland & mucilaginous

Shape and size Irregular tears or vermiform

pieces
 History
⦿ used in commercially for about 100 yrs
⦿ 20th century as an adulterant & substituent for
tragacanth gum
⦿ However, experience indicated that karaya
possessed certain physiochemical properties that
made it more useful in tragacanth.
⦿ less expensive
⦿ India largest producer and exporter
 Chemical Constituents

⦿ partially acetylated polysaccharide containing

about 8% acetyl groups and about 37% uronic
acid residues
 Chemical Test

⦿ 1g of powdered Karaya gum with 50mL water:

viscous solution and acidic
⦿ 0.4 g of p. karaya gum with 10ml ethanol-water
mixture: swelling
⦿ Ruthenium red: pink color
 Uses:

⦿ Effective bulk laxative (swelling property)

increases the volume of the gut content (to be
taken w/ plenty of water)
⦿ adhesive for dental fixtures and ostomy
equipment; base for salicylic acid patches)
⦿ demulcent property as an ingredient in lozenges
to relieve sore throat
⦿ protective coating applied to dentures
⦿ Pharma industry: emulsifier, thickener and
stabilizer
⦿ industries: paper & textile
⦿ cosmetics, hairsprays & lotions to provide bulk
 Adulterant and Substitutes

⦿ As a substitute for gum tragacanth

Karaya gum
Marine gums
 Algin

⦿ Synonym: Sodium Alginate

⦿ Origin: purified carbohydrate extracted brown
algae by the use of dilute alkali
⦿ - Brown algae - Macrocystis pyrifera
⦿ (Lessniaceae) Phaeophyceae
⦿ others: Ascophyllum, Ecklonia, Laminaria,
Nereocystis
⦿ Constituent: Algin (sodium salt of alginic acid)
⦿ Use: suspending agent(food, ice cream, salad
dressing) , sizing
⦿ Alginic acid NF 18- insoluble in water, tablet
binder, thickening agent
⦿ Calcium alginate - forms a firm gel, dental
impressions
 Synonyms

⦿ Algin, Alginic acid sodium salt, salt

polymannuronate, kelgin, minus, protanal
 Biological Source

⦿ purified carbohydrate extracted from brown

seaweed (algae) by treatment of dilute alkali
 Geographical source

⦿ sea-weeds are found in Atlantic and Pacific

oceans, particularly coastal lines of Japan, US,
Canada, Australia and Scotland

⦿ in India, found near the coast of Saurashtra

⦿ largest production: U.S and U.K

Brown seaweed
 Collection and Preparation

⦿ used for extraction of alginic acid

⦿ giant kelp found mainly in Pacific ocean
⦿ mechanical harvesting: 4x a yr
⦿ alginic acid present in the cell wall
⦿ seaweeds are harvested, dried, milled and
extracted with dilute sodium carbonate solution
 Morphology

Color White to buff coloured powder

Odor Odourless
Taste Tasteless
Appearance Either in coarse or fine powder; readily
soluble in water forming viscous
colloidal solution; insoluble in alcohol,
ether, chloroform and strong acids
 History
⦿ A hard, horny polysaccharide, was first isolated
by the English chemist Stanford in 1883 and in
Britain was first marketed in 1910.
⦿ 1929: commercial production began in U.S
⦿ produced in U.K, France, Norway and Japan
⦿ production: 15,000 tones per annum
 Identification tests

⦿ Precipitate formation w/ Calcium Chloride: a

voluminous, gelatinous ppt is formed
⦿ Precipitate formation w/ NH4SO4 : NO ppt
⦿ Test for Alginate: a cherry red color develops to
deep purple
Chemical Constituents

Sodium salt of alginic acid, a linear polymer of

L- guluronic acid and D- mannuronic acid
 Uses
⦿ High & medium viscosity grades: for preparation
of creams, thickening and stabilizing emulsions
⦿ good suspending and thickening agent but
POOR emulsifying agent
⦿ tablets & lozenges: binder & disintegrating agent
⦿ Food Industry: preparation of jellies, ice creams
etc.
⦿ as protectant in inflamed areas near stomach
entrance MOA: stomach acidity causes
formation of insoluble alginic acid and CO2; the
alginic acid rises to the top of the stomach
contents forming protective layer
 Marketed Product

⦿ Manudactured by Taejoon Pharm Co. Ltd.

Seoul for Tx of gastric and duodenal ulcer,
erosive gastritis, reflux esophagitis, hemostasis in
gastric biopsy by endoscopy
algin
 Agar
⦿ Use: laxative, suspending agent, emulsifier,
gelating agent, surgical lubricant, tablet
excipient, disintegrant
⦿ Notes:
› Agarose - clinical diagnostics - matrix for
immunodiffusion, electrophoresis(separation of
proteins), gel filtration and gel chromatography
 Synonym

⦿ Agar agar, Japanese Isinglass, Vegetable Gelatin

 Botanical source:

⦿ It is the dried gelatinous substance obtained by

extraction with water from Gelidium amansii or
various species of red algae like Gracilaria and
Pterocladia, belonging to family Gelidaceae
(Gelidium and Pterocladia), Gracilariaceae
(Gracilaria)
 Geographical source

⦿ Japan: only country producing agar before World

war II
⦿ Now:
⦿ Japan South Africa
⦿ Australia United States
⦿ New Zealand Chile
⦿ Korea Spain
⦿ Portugal
 History

⦿ emergence and development of microbiology

discipline
⦿ first observed by a Chinese Emperor in the mid
16th century
⦿ Japanese dominance of Agar trade only ended
with World War II
 Collection

⦿ The red algae are grown in rocks in shallow

water or on the bamboos by placing them in the
ocean.
⦿ collection made in summer (May and October)
Red algae
 Morphology
colour Yellowish white to gray or colourless
odour Slight/ odourless

taste mucilaginous
shape Strips, flakes or coarse powder
size Strips are about 60cm in length & 4mm wide. Wide
sheets are 50-60cm long & 10-15 cm wide

solubility Insoluble in organic solvents, cold water but soluble in

hot water & forms a gelatinous soln after cooling the hot
soln
 Chemical Constituents

⦿ 2 different polysaccharides:

⦿ Agarose

⦿ Agaropectin
 Chemical Tests

⦿ (+) test to fehling’s solution

⦿ (+) test with Molisch reagent
⦿ Ruthenium red to agar powder red mucilage
color
⦿ Warmed in a KOH soln canary yellow
 Uses

⦿ treat chronic constipation, as a laxative,

suspending agent, an emulsifier, a gelating agent
for suppositories, a surgical lubricant, as a tablet
excipient, disintegrant, dental impression mold
base in medicinal encapsulation and ointment
base
 Substitutes and Adulterants

⦿ Adulterants:
⦿ Gelatin & danish agar (has a gel strength w/c is
half of its gel strength of Japanese agar
 Carrageenan
⦿ Synonym: Irish Moss, Pearl Moss
⦿ Origin: hydrocolloids obtained from
various red algae, Chondrus crispus or
Gigartina mamillosa (Gigartinaceae)
⦿ Constituents: carrageenan hydrocolloids
› galactans with sulfate esters(higher sulfate than agar)
⦿ contains several components - κ, ι, λ
carrageenans
⦿ κ, ι - good gelating agents
⦿ λ - useful thickener
⦿ Uses:
⦿ forms gels to give stability to emulsions and
suspensions, toothpaste formulations
⦿ demulcent, bulk laxative
⦿ Substitute:
› Furcellaria fastigiata (Danish agar)
› extract - furcellaran (hydrocolloid similar to
κ-carrageenan
 Danish agar

⦿ Syn: Furcerallan
⦿ Origin: Furcellaria fastigiata
⦿ Constituent: k-carrageenan
⦿ Use:
Seed gums
 Plantago seed
⦿ Synonym: Psyllium seed, plantain seed
⦿ Origin: cleaned, dried ripe seed of
› 1. Plantago psyllium,
› 2. P. indica(P. arenaria)
● known in commerce as Spanish or French
Psyllium seed
› 3. P. ovata
● known as blonde psyllium seed or Indian
plantago (Plantaginaceae)
⦿ Constituent: seed coat (husk) contain 10 - 30%
hydrocolloid on hydrolysis yields arabinose,
galactose, galacturonic acid, rhamnose, xylose
⦿ Use: cathartic (gives bulk and lubrication)
⦿ treatment of diverticular disease or irritable
bowel syndrome
Plantago seed
 Cydonium

⦿ Aka: quince seeds

⦿ Source: Cydonia vulgaris
⦿ Forms viscous solutions with thixotropic
properties
⦿ Used in some wave setting lotions
 Guar gum

⦿ Aka guaran
⦿ Source: Cyamopsis tetragonoblus
⦿ Const: galactomannan
⦿ Use: bulk forming laxative & thickening agent,
tablet thickener, diintegrant
 Locust Bean gum

⦿ Synonym: Carob
⦿ Origin: hydrocolloid from the powdered
endosperm of the seed of Ceratonia siliquia
(Fabaceae)
⦿ Constituents: galactomannan (similar to guar
gum) main chain - mannose with galactose
substituents
⦿ Use: thickener, stabilizer
Locust bean gum
Microbial gum
 Xanthan Gum

⦿ Origin: produced artificially by fermentation of

the bacterium Xanthomonas campestris on
glucose
⦿ Constituents: 1,4 - β glucan backbone - 0 - 3
substituted trisaccahride β mannopyranose,
glucopyranosyluronic acid, α - mannopyranose
⦿ Use:
⦿ Notes:
› exocellular gum recovered from fermentation
› broth and precipitated by isopropyl alcohol
› exhibit pseudoplastic properties in toothpaste and
ointments
 Elm

⦿ Synonym: Elm bark, Slippery Elm

⦿ Origin: dried inner bark of Ulmus fulva
(Ulmaceae)
⦿ Constituent: Mucilage
› galacturonic acid + rhamnose, xylose galactose
⦿ Use: demulcent, emollient
⦿ Note: applied “ad libitum”
 Pectin

⦿ General term for a group of polysaccharides

present in cell wall of seed bearing plants -
middle lamellae
 3 general types of peptic
substances
1. Pectic acid - unbranched molecule consisting
of galacturonic acid residues at an α 1,4 linkage

2. Pectin - resembles pectic acid but carboxylic

acid groups is esterified with -CH3; forms gel
3. Protopectin
› all insoluble pectic substances present
during the ripening of fruits
› heated with dilute acid converts to pectin
and pectic acid
⦿ gelling power and viscosity of solution
depends on the number of galacturonic acid
residues in the molecule
⦿ pharmaceutical - pure pectin does not contain
sugar
⦿ commercial pectin - contains sugar and from
citrus peel
⦿ 1 part pectin heated to 9 parts of water - a stiff
gel
⦿ Use:
› Protectant, suspending agent
› ingredient of antidiarrheal formulations
 Mallow Leaves

⦿ Synonym: Malvas, Common Mallow

⦿ Origin: dried leaves of Malva sylvestris and M.
rotundifolia (Malvaceae)
⦿ Use: excipient, demulcent
⦿ Synonym: Marshmallow, marshmallow root
⦿ Origin: dried root of Althaea officinalis
(Malvaceae) deprives of the brown corky layer
and small roots
⦿ Use: demulcent, excipient (pill making)
⦿ Both given ad libitum
Mallow plant
 TESTS FOR CARBOHYDRATES
1. Reduction of Fehling’s Solutions- brick red ppt
of cuprous oxide
2. Molisch’s Test- purple color when treated with
L- naphthol and conc. Sulfuric acid
3. Osazone formation
4. Resorcinol Test for Ketones
5. Test for Pentoses
6. Keller- Killiani Test
7. Enzyme Rxns
8. Chromatography
 Test for Composition Positive reults
Molisch’s General test a-napthol Purple/red

Fehling’s Reducing sugars A- CuSO4; Brick red ppt

B-KNaTartrate

Benedict’s Reducing sugars NaOH + CuSO4 Brick red ppt

Barfoed’s Reducing Acetic acid + Brick red

sugars: CuSO4
monosaccharide
s
 Test for Composition Positive
results
Tollen’s Reducing Ammoniacal Silver mirror
sugars AgNO3
(aldehyde)
Picric acid Reducing Picric acid Mahogany
sugars

Nylander’s Reducing NaKtartrate + Brown

sugars K/NaOH + Bi

Osazone mannse Phenylhydrazine yellow

 Test for Composition Positive
reults
Seliwanoff fructose resorcinol Cherry red

Keller-killiani’s deoxysugars Acetic acid, Reddish brown

FeCl3, sulfuric
acid
Moore’s Reducing sugars Heat w/ alkali caramel
(glu)

Mucic acid galactose Nitric acid Insoluble ppt

Bial’s pentoses Resorcinol + Blue green

iron