You are on page 1of 109

Carbohydrates: Chemistry and

Nomenclature
 Also known as “saccharides” (Lt. ‘saccharum’,
sugar)
 (CH2O)n
 most abundant organic molecules in nature with
remarkable variety of functions
 polyhydroxy aldehydes & ketones
 first molecules in the energy cycle from the sun to
plants to molecules used by most other organisms
Carbohydrates
 aldehyde or ketone alcohols that
contain C, H and O
 the H and O has the same ratio as that
of water, thus they are named as
CARBO + HYDRATES
 first products of photosynthesis
Functios of Carbohydrates
 Structural – cellulose, chitin, peptidoglycan
 Energy storage – starch, glycogen
 Biologically active:

Transport – glycoproteins in plasma (transferring)


Regulatory– glycoproteins like FSH, LH, TSH
Catalytic – glycoproteins (ribonuclease, -amylase)
Immune response – Ig, interferons, Rh factors
Cell lubrication & supportive function – sialoglycoproteins
Cell differentiation – ABO blood grouping
Cell membrane, clotting factors, & protective cellular coat
proteins – glycocalyx, fibrinogen, prothrombin
Classifications of Carbohydrates as to
size.
I. Monosaccharides
II. Oligosaccharides
III. Polysaccharides
a. Homoglycans
◦ 1. Starch- Glucosan- yields glucose units
2. Inulin- Fructosan- yields fructose units
3. Cellulose- Glucosan- yields glucose units
b. Heteroglycans
◦ 1. Gums and Mucilages
◦ 2. Glycosides
MONOSACCHARIDES
 simple sugars; have 1 sugar unit; cannot be further
hydrolyzed;
 3 to 9 Carbon atoms
 crystalline, water-soluble and sweet
 most important monosaccharide in plants:
hexoses

Classification based on the functional group (C=0)


1. aldose - aldehyde
2. ketose - ketone
MONOSACCHARIDES
 Classification based on # of Carbons
EXAMPLES
# OF
NAME ALDOSE KETOSE
CARBONS
(-ose) (-ulose)
2 Diose Hydroxyacetaldehyde -
(never free in nature)
3 Triose Glyceraldehyde (DHA) Dihydroxyacetone
4 Tetrose Erythrose, Threose Erythrulose
5 Pentose Ribose, Arabinose Ribulose
6 Hexose Glucose, Galactose Fructose
7 Heptose - Sedoheptulose
8 Octose - D-glycero-D-mannoctulose**
**found in avocado pulp and
Sedum

 Arabinose, xylose and ribose, glucose, galactose, fructose *occur free in


nature
MONOSACCHARIDES
Hexoses
Most Important Monosaccharides
GLUCOSE: Chemical properties
• aldohexose
• reducing sugar as
determined by BENEDICT'S
TEST
• occurs as: linear and cyclic
• form a pyranose ring
containing a stable cyclic
hemiacetal or hemiketal
GLUCOSE: Chemical properties

• Linear configuration:
Fischer Projection
– L-glucose- less active
– D-glucose-more active
GLUCOSE: Chemical properties
• Cyclic configuration:
Haworth Projection
– looks like a pyran;
glucopyranose, 6-
memb ring

– Furanose, 5 memb
ring; unstable but
may be stabilised on
glycoside formation
GLUCOSE: Anomers

In the pyranose form of glucose, carbon-1 is chiral, and thus two stereoisomers are possible: one
in which the OH group points down (α-hydroxy group) and one in which the OH group points up
(β- hydroxy group). These forms are anomers of each other, and carbon-1 is called the anomeric
carbon
Glucose / dextrose (D-glucose / -D-glucopyranose)

• “blood sugar, physiologic sugar, grape


sugar, corn sugar”
• natural source: grapes

use: nutrient (dextrose): administered


thru PO, SC, IV or enema) ,
• mask unpleasant taste
• flavor
Glucose / dextrose (D-glucose / -D-glucopyranose)

– Parenteral- rigorously purified


• -D5W, D5NSS, D5LR- nutrient
• D5050
– Pharmaceutic necessity- less
rigorous purification
• Liquid Glucose- syrupy liquid, almost
colorless and taste sweet;
sweetening agent
• Dextrose excipient- crystalline
sweetening agent (binder,
disintegrant or coating agent)
Related compounds:
Glucose derivatives
a. liquid glucose - thick, syrupy liquid from
incomplete hydrolysis of starch
b. calcium gluconate - electrolyte replenisher
c. calcium gluceptate - calcium source
d. Ferrous gluconate - hematinic, given for iron
deficiency anemia
Fructose: Levulose

 a ketohexose
 Reducing sugar
 Fruit sugar; sweet fruits and honey
 the sweetest monosaccharide
Fructose
• Fruit sugar: sweet fruits and honey
• also known as Levulose, the sweetest monosaccharide
• In nature, in furanose form;
• isolated in crystalline form (pyranose form)
Uses of Fructose

ingredient in infant feeding formula


ingredient in Fructose injection, nutrient
 Fructose appears to be as dangerous as
glucose and so does not seem to be the
answer for diabetes.
Tests for fructose:

Reducing sugars:
Barfoed (CuSO4 + HAc)
or C4H6CuO4 = Cu2O

Benedict’s rgt (CuSO4 + Na2CO3)


PENTOSES: C5 sugar
Xylose
 wood sugar
 obtained from boiling corn cobs,
straw, heart of deciduous trees and
similar mateials with dilute acids
to hydrolyze the xylan polymer
 diagnostic aid in intestinal
malabsorption
DISACCHARIDES = double sugar or bivose

• crystalline water soluble


• two sugars linked by glycosidic bond or linkage
• α- or β- or a combination of the two (α-,β-).
Dissacharides

+
S UC R OS E H
GL UC OS E + FR UC TOS E
+
H
MAL TOS E 2 GL UC OS E
+
H
C E L L OBIOS E 2 GL UC OS E
+
H
GE NTIOBIOS E 2 GL UC OS E
+
H
TR E HAL OS E 2 GL UC OS E
+
H
ME L IBIOS E GAL AC TOS E + GL UC OS E
+
H
L AC TOS E GAL AC TOS E + GL UC OS E
Disaccharides
 composed of two monosaccharide units
 formed via dehydration synthesis
DISACCHARIDES – 1.SUCROSE/TABLE SUGAR/
SACCAHARUM

 glucose + fructose; α-1,2


glycosidic bond,
 non reducing sugar

 molasses: residual,
 dark colored syrup after
crystallization process
pharmaceutic necessity for syrups;
demulcent; nutrient; preservative
 _______- bitter taste of beer
 invert sugar: equimolar amounts of
glucose and fructose; darken due to
fructose
Sucrose
 -obtained from
◦ Sugar cane Saccharum officinarum, Poaceae
◦ Sugar beets Beta vulgaris, Chenopodiaceae
◦ Sugar maple Acer saccharum, Aceraceae
Uses of Sucrose
 demulcent
 sweetening agent
 coating agent
 preservative
 production of syrups
 retards oxidation
2. Trehalose

found in brown seaweed, widely distributed in fungi (mycose)


 glucose + glucose; α-1,1 glycosidic bond
High water-retention property, texturizer and stabilizer
Anhydrobiosis *
Non-reducing sugar
3. Maltose/malt sugar/ beer sugar
produced in large quantities by the hydrolysis of
starch during germination of barley
 use: component in beers
glucose + glucose; α-1,4 glycosidic bond

Hordeum vulgare L.
4. Lactose / milk sugar
 from animal source: from fresh cow’s milk
(Bos taurus)
 from the crystallization of whey, a
by-product of cheese production
 glucose + galactose;
 -1,4 glycosidic bond
- use: tablet diluent
- lactose intolerance: absence of
enzyme lactase/ - galactosidase
(diarrhea, GI disturbance)
Lactose (α form)

Kumyss
an alcoholic beverage made from fermented
mare's milk; made originally by nomads of
central Asia
Cheese production
 Milk (stand for hrs)  fat globules rise
on top  (churned)  become butter

buttermilk below
↓(remove)
skimmed milk
Treat with
inorgsalt+ (lactose) - whey (liq) rennin
(chymosin)

(solid) CHEESE ← coagulum formed

Casein (insoluble) ← Caseinogen (soluble)


 Contents
 [hide]
 1Process
◦ 1.1Culturing
◦ 1.2Coagulation
◦ 1.3Draining
◦ 1.4Scalding
◦ 1.5Mould-ripening
 2Quality control
5. Lactulose
5. Lactulose
 synthetic sugar from the tautomerization (alkaline
rearrangement of a ketone to an enol) of lactose
uses:
1) laxative (Duphalac®)
poorly absorbed; bacteria (colon) converts
it to acetic acid & lactic acid = ↑ peristalsis
2) decreases blood ammonia concentration in
portal-systemic encephalopathy
 acidified stools trap ammonia as NH4+
so, ↓ reabsorption, ↓B ammonia
 Kumyss
Tautomerization
 Tautomers are constitutional isomers of organic
compounds that readily interconvert in a rapid
equilibrium.
 This reaction commonly results in the relocation
of a proton.
 tautomerism is relevant to the behavior of amino
acids and nucleic acids
Keto-enol tautomerization
 the most common tautomeric relationship in
organic chemistry is the keto-enol pair.

As a general rule, the keto form of a carbonyl is lower in energy, and thus
predominates at equilibrium. Acetone, for example, is present at >99% keto form at
equilibrium.
OLIGOSSACHARIDES: 3-10 sugar units
1. Maltotriose – by enzymatic digestion of amylose in
starch

Nutrition Facts:
Calories per gram = ~4
Glycemic index (GI) = probably >100
Sweetness, related to sucrose = 30%
Net carbs = 100%
2. Dextrins “generic term"
 “limiting dextrins”: products of partial hydrolysis of
starch or glycogen by β- amylase, α-glucosidase)
STARCH (amylases) LIMITING (α-glucosidases) GLUCOSE
DEXTRINS

◦ Browning of bread
◦ DETOX Foot Pads”

 α-glucosidase inhibitors:
- inhibit post-prandial (after eating) increase in glucose
levels (anti- DM type 2)
ex . Acarbose,(Precose); Miglitol;(Glyset)
AE: flatulence, hepatotoxicity
Oligosaccharides:
OLIGOSACCHARIDES - have 3-10 sugar units

3. gentianose - glucose + glucose + fructose


4. raffinose - glucose + galactose + fructose
Tetrasaccharides:

5. stachyose - glucose + galactose + galactose+


fructose
Test question?
a. sucrose
b. raffinose
c. lactose
d. stachyose

1. The ff sugars have fructose in its structure except ?


2. Which is disaccharide?
3. How many are oligosaccharide?
Drugs Containing Compounds
Metabolically Related to Sugars
Products of Oxidative Metabolism:
Cherry Juice
Plant Acids
CHO
K2HgI4

(CHOH)n

CH2OH

CHO

(CHOH)n

CH2OH

Nesslers rgt = K2HgI4


Plant Acids
-are simple organic acid containing ≤ 6(six) carbons and 2 – 3
carboxyl groups (-COOH ).

 Most Popular Plant Acids: malic acid, oxalic acid, succinic acid,
tartaric acid, citric acid.
 Less known but of equally wide distribution and importance are:
isocitric, fumaric,cis-aconitic,oxaloacetic acid and ά-ketoglutaric
acid.

 Function: to neutralize the excess basic ions.


 Neutralizing metallic ions is a function of all acids in controlling
enzyme activity in the protoplasm.
Plant Acids
 Uses:
◦ acidulants in effervescent
formulations
◦ component of buffer systems
1. Citric Acid- isolated by Scheele
from lemon juice in 1784
(anticoagulant)
2. Lactic Acid- acidulant in infant
feeding formula
3. Tartaric acids- by-product of
wine industry
4. Ferrous fumarate- hematinic
Cherry Juice or
Succus cerasi
 ripe fruit of Prunus cerasus, Rosaceae
 contains pectin, the main cause of
incompatibilities especially when added to
preparations containing alcohol
 remedy: add 0.1% benzoic acid and leave for
1 week
 constituent: malic acid
 use: preparation of cherry syrup- used to
mask the taste of sour drugs
Plant Acids: 1.Oxalic Acid
.
 Very insoluble as calcium salt in the form of
raphides

 Balimbing (Averrhoa carambola);


Kamias (Averrohoa bilimbi)

 a colorless crystalline solid w/c dissolves in water to give a


solution w/c is acid to litmus.
 + CaCl2 = CaC2O4 , insoluble in HOAc but soluble in HCl.
 C2H2O4 (basic formula)
Plant Acids: 2. Malic Acid

Malic acid –distributed in unripe fruits


such as apples and pears where they occur as
free acids.
 They are colorless crystals w/c deliquesce
readily.
 They are ppted when treated w/ CaCl2 from
aqueous alcohol soln w/c is soluble in HOAc.
 C4H6O5 (basic formula)
Plant Acids: 3. Tartaric Acid

occurs in plant juices of fruits


such as grapes, tomato and pineapple.

 They resemble sugar by giving an odor of


burnt sugar when heated.

 They form a ppt when treated with CaCl2


w/c is soluble in HCl.
 C4H6O6
Plant Acids: 3. Formic Acid and Acetic
Formic acid – “formica”
• Found in ants, volatile poison
• Antibacterial for livestock feed, warts, artificial
flavoring or perfumes

Acetic acid
Precursor of fatty acids/lipids; vinegar
Plant Acids: 4. Succinic Acid

 – widely distributed esp in unripe fruits


such as grapes, apples and bananas.

 It is colorless, crystalline solid

 best isolated as the insoluble barium salt.


 The calcium salt is only ppted from
concentrated solns or on addition of
alcohol.
 (CH2)2(CO2H)2
Plant Acids:

 Shikimic Acid
-precursor of aromatic compounds
- Amino acids

 Ascorbic Acid
-Vit. C, water soluble

 Citric Acid
- Isolated from Lemon juice
- acidulant in effervesecent preparations,
buffer system
Other Plant acids
 Caffeic acid–used in H+ transporting systems in
plant resp
 Protocatechuic acid –present in onion varieties
w/c make it resistant to attacks of a particular
fungus.
Importance :
 represent breakdown products of amino acid
metabolism.
 They play an important role in cellular
respiration. Compound acids of Krebs cycle
include all the plant acids except tartaric acid and
oxalic acids.
Determination of Plant Acids

Plant Material containing the ff:


 Citric,malic tartaric,oxalic acids
 H+
 ether/ alcohol
 Liquid extract
 PbOAc2
 Pb oxalate ,Pb malate ,Pb tartrate ,Pb citrate
 dil NH4OH
 Pb oxalate ppt soln of 3 other acids
 ins.HOAc; sol in HCl
Determination of Plant Acids
 Malate, Tartrate, Citrate solns
 alcohol
 KOAc
 KHC4H4O6 soln of citrate, malate
 white ppt CaCl2

 cal malate cal citrate
soln
 white ppt
 heat

 cal citrate ppt


Products of Reductive Metabolism:
Mannitol & Sorbitol = Sugar Alcohols
Mannitol
Mannitol = C6H14O6
 from manna, Fraxinus ornus
Oleaceae
 osmotic diuretic and osmotic
laxative
 Reduction of intracranial pressure and
treatment of cerebral edema
 Sweetener for diabetic food
Sorbitol
 from the berries of mountain
ash, Sorbus aucuparia,
Rosaceae
 aka D-glucitol
 taste half as sweet as sucrose

 Has humectant properties,


 NOT absorbed on oral ingestion
that is why it is used in the
manufacture of toothpastes
and chewing gums.
The polyol pathway
Alcohol or Ethanol
 94.9% ethanol by volume at 15.560C
 product of fermentation
 undergo the process of distillation to
concentrate the alcohol content to 40-
55%
◦ Brandy - Wine-from ripe grapes
◦ Whiskey- Malted Grain
◦ Rum - Molasses
Uses of Alcohol
 In low concentration, CNS stimulant
 In higher concentration, CNS depressant

***Diluted alcohol: 48.4-49.5% ethanol at


15.560C
POLYSACCHARIDES /
POLYGLYCANS
Classification of polysaccharides
According to products of hydrolysis
1. Homopolysaccharides/ Homoglycan
One type of monosac upon hydrolysis
- fructosan/fructan, glucosan/glucan
2. Heteropolysaccharides/ Heteroglycan
More than one type of monosac upon hydrolysis
- gums & mucilages, pentohexosans
 According to function
1. Storage: starch, inulin
2. Structural: cellulose, pectin
Starch
 temporary storage form of
photosynthetic products
 from:
◦ Corn Zea mays, Poaceae
◦ Wheat Triticum aestivum, Poaceae
◦ Potato Solanum tuberosum,
Solanaceae
Starch: 2 Major Components
Bases of Difference Amylose Amylopectin
Linear Branched
Structure 250-300 D-glucopyranose 1000 or more glucose units
units linked by α-1,4 linked by α1,4 glucosidic
glucosidic bonds bonds & α1,6
glucosidic bonds at every
25 glucose units.

Solubility in water soluble Insoluble or sparingly


soluble

Iodine test Deep blue Blue violet/ purple

Ratio 25.00% 75.00%


Amylose
Amylopectin
Starch Residues on enzymatic hydrolysis

-Dextrin
(polysaccharide)
-Maltose
(disaccharide)
-Glucose
(monosaccharide)
Starch
Uses:
as an antidote for iodine poisoning
demulcent – soothes internal irritated tissue
emollient – soothes external irritated tissue
dusting powder;tablet filler;binder;disintegrant
amorphous unlike monosaccharides – are crystalline
Starch residues:
1. dextrin ( polysaccharides )
2. maltose ( disaccharide )
3. glucose ( monosaccharide )
α-amylase - dextrins; present in pancreatic juice & saliva
-metabolism/ breakdown of carbohydrates starts in the mouth
β-malt amylase - dextrin and maltose; hydrolyzes starch to
nearly pure maltose
Polysaccharides: O
HOCH2
OH O
CH2 OH
O CH2OH
HO
O HO OH
O
O
O OH
HO
CH2 OH
OH
CH2 OH
CH2OH OH
HOCH2
HO HO
O
O O
O
O
O
HO
O
CH2OH OH OH
OH OH OH
O CH2 OH
CH2 OH
O O
HOCH2 OH HO O HO
OH OH
O O
O OH O
HO O
OH CH2 OH
O
CH2 OH
O HO
OH
O
HO
O
OH
CH2 OH
O
S TAR C H

I2
Amylodextrin blue-black

I2
E rythrodextrin reddish-brown

I2
Achrodextrin colorless

I2
Maltose colorless

I2
GL UC OS E colorless
Enzymes that breaks down starches
 Amylases
1. α-amylases – in pancreatic juices (amylopsin) and
saliva (ptyalin)
- random splitting at α-1,4 links
2. β-amylases
- splits α-1,4 links only so end product is
nearly purely maltose
- Remove maltose units from non-reducing end of
polysaccharides
- - at branching points: maltose and dextrins
- (incomplete hydrolysis)
Starch Preparations
1. Pregelatinized starch- starch that is
chemically or mechanically processed to
rupture all or part of the granules; tablet
binder

2. Sodium starch glycollate- disintegrating


agent (tablet disintegrant)

3. Hetastarch- plasma expander (6%), 90%


amylopectin
Glycogen/animal starch/glucosan

 Frequency of branching:
 every 10 units
 more highly branched
 iodine test: wine red
Inulin
 Fructosan (β-2,1 bonds)
 use: ingredient in culture
media;
 used in the evaluation of
renal function – GFR
Dextran
 Glucosan

 Leuconostoc mesenteroides
release the enzyme dextran
sucrase which is responsible
for the conversion of
sucrose to dextran.
 plasma expander because it
has the same osmolarity and
viscosity as with plasma
CELLULOSE
-enzyme is cellulase
-made up of fibers β 1,4
-can be a bulk laxative; filtering
agents
-inert, unreactive

Primary cell wall Secondary


cell wall const.
a.Cellulose a. lignin
b.Hemicellulose b. suberin
c.Pectic substances c. cutin
- Natural sources:
CELLULOSE: Cotton
a. Purified Cotton / Absorbent Cotton- hair of the
seed, freed from adhering impurities, deprived of fatty
matter, bleached & sterilized in its final container,
of Gossypium hirsutum, Malvaceae
◦ Use: mechanical protection against bacteria
◦ absorb mucus, pus and blood
A.CELLULOSE

 b. Soluble gun cotton/


Pyroxylin/Nitrocellulose
◦ -formed by the action of nitric and sulfuric acid on cotton
 Other ingredients:
 Castor oil- flexibility
 Camphor-water-proof
◦ Use: topical protectant

 c.Other cellulose derivatives


◦ Cellulose acetate phthalate< CAP> coating agent
CELLULOSE DERIVATIVES”
 methylcellulose - bulk laxative and suspending agent
 ethylcellulose - tablet binder and film coat
 Collodion- pyroxylin + alcohol + ether (1:3)
◦ flexible collodion = collodion + camphor (2%) +
castor oil (3%)
◦ use: topical protectants

 chitin - homopolymer of N-acetyl--D-glucosamine


CELLULOSE
Solvents that can dissolve
cellulose:
1) Schweitzer’s reagent –
gelatinized then dissolved
Commercial name:
Cuoxam
Chemical name:
ammoniated cupric oxide
soln. of cupric
hydroxide in conc
ammonia
2) Conc zinc chloride
CELLULOSE : Ultra Structure

Micelle – elementary fibril of


cellulose
1 micelle = approx 100 individual
cellulose units arranged in
paralle bundles
20 micelle = 1 microfibril
250 – 400 microfibril = 1 fibril
1,500 fibril = 1 FIBER
B. HEMICELLULOSE
B.Hemicellulose w/ 4% HCl - uronic acid + pentose
glucuronic + xylose
galacturonic + arabinose
w/ NaOH - soluble

Plant Material 4% NaOH soluble HOAc&EtOH


hemicellulose ppted.

CROSS-BEVAN METHOD
Plant Material
boiling w/ 1% NaOH ffd. by treatment
with Cl2 & Na2SO3 ; ethanolamine &
SO3.
B. HEMICELLULOSE
Soluble chlorinated insoluble crude cellulose
lignin ( holocellulose )
(α,β,γ – cellulose)

17.5% NaOH
α –cellulose β&γ-cellulose
insoluble soluble
(pure cellulose) (non-cellulosic
cell wall const)
H+
β-cellulose γ-cellulose
ppted remain in soln
LIGNIN

-Amorphous
-Preparations are either brown/ yellow
-Found in hard mature tissues such as those of wood and
straw
2 major groups:
1. Aromatic nuclei of great complexity
2. Carbohydrate grp – can be cellulose / cellulose derivative
2-Methoxy-4-allylphenol

REACTIONS: 2xy 2-methoxy-4(1-propenyl)-phenol

Lignin dry dist eugenol + isoeugenol


under reduced pressure
LIGNIN
Hot aqueous SO3 soln. Soluble lignin
unstable to oxidizing agents (hypochlorite,permanganate &
H2O2)
simple fatty acids & dicarboxylic
acids.
72% H2SO4 insoluble lignin

CUTIN
b.CUTIN
-present in the cuticle (outer covering in the epidermis of
leaves & stems of higher plants)
-gives the shiny look in leaves & stems
-for preventing loss of water
-more fat = more cutin
CUTIN
Cutin is not soluble in fat solvents & resistant to cellulose
solvents.
-made up of unsat. fatty acid/ soap/ esters of fatty acid
w/c have undergone condensation and oxidation.

SUBERIN
c.SUBERIN
-Complex mixtures of fatty acids w/c have undergone
condensation and oxidation
-Cork –like material w/c occurs in the wall of the periderm
cells - middle lamella & inner cellulose layer
-cutin& suberin can’t be extracted using fat solvents
-unaffected by cellulose solvents.
Heteroglycans
Pectin
Gums and Mucilages
Gums and Mucilages
 Plant Exudates
 Marine Gums
 Seed Gums
 Microbial Gums
 Pectin
Gums and Mucilages
 Natural plant hydrocolloids that may
be classified as anionic or non-ionic polysaccharides
 Mucilage as water retaining vehicles, (Althea root and
psyllium seed)
 Gums- Produced by plants as a protective agent after
injury, as solidified exudates
 Upon hydrolysis, they yield arabinose, galactose, glucose,
mannose, xylose and other uronic acid derivatives
Gums: Shrub and Tree exudates
a. Tragacanth / Gum tragacanth
- Astragalus gummifer
- Three forms:
1.vermiform – wormlike ,twisted in coils
2. tragacanth sorts - tearlike
3. ribbon / flake gum - has longitudinal striations

- components: Bassorin (60-70%): swelling property


Tragacanthin (30-40%): water-soluble
- use: suspending agent, emulsifying agent (6%)
NOTE: more resistant to acid hydrolysis, so it works in ↓ pH
Gums: Shrub and Tree exudates
b. Acacia / Gum arabic
- Acacia senegal
- arabin: complex mixture of Ca, Mg, and
- K salts of Arabic acid
use: suspending agent (35%)

c. Ghatti gum / Indian gum


- exudate form Anogeissus latifolia (Combretaceae)
use: substitute for acacia (forms more viscous dispersions)
d. Karaya gum / Sterculia gum
-exudate from Sterculia urens
- forms a discontinuous type of mucilage
- use: bulk laxative, emulsifying agent,
- dental adhesive
Marine gums
a. sodium alginate / algin
-from brown seaweeds (Macrocystis porifera)
- components: salts of Alginic acid, mannuronic acid
- use: suspending agent, food industry (ice cream, chocolate)

b. agar / Japanese isinglas/ gulaman


- substance from Geladium cartilagineum or Gracilaria confervoides
- use: stiffening agent in preparation of culture media; thickening
agent
- components: Agarose - has low sulfate content
Agaropectin
Marine gums
c. carrageenan / Irish moss / chondrus
- hydrocolloids from red algae or seaweeds
- Chondrus crispus, Gigartina mamillosa
- 3 Forms: -carrageenan and -carrageenan – with gelling
property
-carrageenan – non gelling property; use: thickener

d. Danish agar / furcellaran


- from red algae Furcellaria fastigiata
- - similar property to -carrageenan (gelating and suspending
agent)
- SoAg CaDa
Seed gums (bulk-forming laxatives)
a. Plantago Seed / psyllium seed / plantain seed
 -Plantago psyllium, P. indica: Spanish or
French psyllium seed
 Plantago ovata: Blonde psyllium or Indian
plantago seed
 plant part used: powdered seed coat

b. Guar gum / guaran


- Cyamopsis tetragonolobus
- plant part used:
- powdered endosperm
- Bulk forming laxative
Seed gums (bulk-forming laxatives)

c. Locust Bean gum / St. John’s Bread / Carob pulp


Ceratonia siliqua
 part used: powder made from flesh of mature
seed pods (“flour”)
 use: chocolate substitute;
 used as thickener and stabilizer
Microbial gums
 Xanthan gum
◦ high MW gum prepared by
◦ the action of Xanthamonas campestris
◦ possesses pseudoplastic properties:
◦ used in toothpastes and ointments
Microbial gums
Dextran
 polyglucan formed from sucrose by the action of a
transglucosylase enzyme system
◦ present in Leuconostoc mesenteroides
◦ use: plasma expander
 Leuconostoc mesenteroides release the enzyme dextran
sucrase (glucosyltransferase) which is responsible for the
conversion of sucrose to dextran
 plasma expander because it has the same osmolarity and
viscosity as with plasma
 n Sucrose → n Fructose + dextran (glucose)n.
Plant Extracts

 Pectin
◦ purified carbohydrates
◦ inner portion of the rind of the citrus fruits or
from apple pomace
◦ use: protectant, suspending agent, antidiarrheal
◦ Kaopectate- Kaolin + Pectin--> antidiarheal
preparation
Types of Pectin

 Protopectin
 Pectin or soluble pectin
 Pectic acid
Types of Pectin

1) Protopectin / Pectose – neutral, insoluble in water


2) Pectin – neutral, soluble in water
3) Pectic acid – acidic, soluble in water.

Protopectin – has a longer chain, usually found in the cell wall


of plants; unriped fruit

Protopectin boiling H2O pectin or pectic acid


amm. oxalate soln
Isolation: a. remove –CH3 grp
b. incomplete deesterification - pectinic acid
Pectin – ripe fruits(methoxylated polygalacturonic acid)
- methyl polygalacturonide chain

Pectic acid – present in over-ripe fruits


H+ uronic acid + hexoses + pentose

3 types of pectic enzymes:


1) Protopectinase – attacks protopectin yielding soluble
pectin
2) Pectinase or polygalacturonase – attacks pectic acid or
pectin yielding galacturonic acid
3) Pectase attacks pectin yielding pectinic acid or pectic
acid.
Plant Exudates
Gum Source Constituents Notes
Acacia or Gum Acacia senegal, Arabin Incompatible in
Arabic Fabaceae preparations
containing more than
60% alcohol
only 5-6% swells in
water

Tragacanth Astragalus Bassorin- gelling 35-36% swells in


gummifer, Fabaceae component water; best mucilage
Tragacanthin- non- most resistant to acid
gelling component hydrolysis

Karaya or Sterculia Sterculia urens, D-galacturonic acid Fetid odor


Gum Sterculiaceae and D-glucuronic
acid
Marine Gums
Gum Source Constituents Notes
Agar or Japanese Algae- Agarose Ingredient of culture
Isinglas Gelidium cartilagineum Agaropectin media
Gracilaria confervoides

Algin Seaweeds Mannuronic acid


Macrocystis pyrifera

Carageenan or Irish Red algae Kappa carrageenan-


moss Chondrus crispus gelling component
Gigartina mamilosa Iota-gelling
component
Delta- non-gelling
component

Danish Agar Furcellaria fastigiata Kappa


Seed Gums
Gum Source Notes
Plantago/ Psyllium/ Plantain Seed coat of Plantago Bulk laxative
Seed psyllium- Spanish Psyllium should be taken with
Plantago ovata- Blonde considerable amount of
psyllium or Indian psyllium water

Cydonium/ Quince Seed Ripe seed of Cydonia


vulgaris

Guar gum or Guaran Endosperm of Cyamopsis


tetragonolobus

Locust Bean Gum/ Carob Pulp Endosperm of the seed of Flour or the carob resembles
or St. John's Bread Ceratonia siliqua chocolate
used by John the Baptist
Gums and Mucilages
 Natural plant hydrocolloids that may be classified
as anionic or non-ionic polysaccharides

 Produced by plants as a protective after injury

 Upon hydrolysis, they yield arabinose, galactose,


glucose, mannose, xylose and other uronic acid
derivatives
-END-