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CARBOHYDRATES
CARBOHYDRATES
Monosaccharides
These sugars contain from three to nine carbon atoms, but those with five and six
carbon atoms (pentoses, C5H10O5 and hexoses, C6H12O6) are accumulated in plants
in greatest quantity.
Glucose: It has an aldehyde group and is therefore called an aldose or 'aldo' sugar,
fructose has a ketone group and is therefore called a ketose. Terms such as
'aldopentose' and 'ketohexose' are self- explanatory.
Fructose: This in nature is always in the furanose form, but when isolated in
crystalline form, it has a pyranose structure.
Uronic acids are produced by oxidation of the terminal groups to -COOH (eg
glucuronic acid from glucose and galacturonic acid from galactose).
These sugars may also be called bioses, trioses and tetroses. They are theoretically
derived from two, three or four monosaccharide molecules, respectively, with the
elimination of one, two or three molecules of water. One of the commonest plant
disaccharides is sucrose, it is formed in photosynthesis by the reaction of UDPG
with fructose-6- phosphate (Fig. 20.3). Control mechanisms for the build-up of
sucrose in leaves, and its breakdown for transport to storage organs, are achieved
by metabolite effector control of the appropriate enzymes.
POLYSACCHARIDES
Because of these structural differences, amylose is more soluble in water than is amylopectin, and this
characteristic may be used to separate the two components.
More efficient separations are effected by complexing and precipitating the amylose with suitable
agents, including various alcohols or nitro-paraffins. Amylose reacts with iodine to form a deep blue
complex; amylopectin gives a blue-violet or purple color.
Most starches have a similar ratio of amylose to amylopectin, averaging about 25% of the former to 75%
of the latter. Certain waxy or glutinous starches contain either no amylose or small amounts (less than
6%).
Beta-Amylase (alpha-1,4-glucan maItohydrolase) produces its effect by removing maltose units from
the non-reducing ends of polysaccharide molecules. The end-product in the case of amylose is nearly
pure maltose. The hydrolytic action of 13-amylase on the alpha-1,4 linkages of amylopectin continues
until a branch point is approached. Because the enzyme lacks the capacity to hydrolyze a-1,6 bonds, the
reaction stops, leaving polysaccharide fragments known as dextrins as the product of incomplete
hydrolysis.
Hydrolysis of starch by mineral acids ultimately produces glucose in nearly quantitative yields. The
course of hydrolysis may be conveniently followed by the iodine reaction, which changes successively
from blue-black to purple to red to no reaction. Starches generally form colloidal solutions rather than
true solutions. If a suspension of starch in cold water is added to boiling water while stirring, the opaque
granules swell and finally rupture to give a translucent sol. If this sol is somewhat concentrated, it sets to
a firm jelly when cooled. Cold, concentrated aqueous solutions of the caustic alkalies, of chloral hydrate,
of ammonium thiocyanate, or of hydrochloric acid also cause the swelling and ultimate rupture of the
starch granules to form pastes.
Applications of sugars and sugar-containing drugs to pharmacy:-
1. Sucrose:-
3. Fructose:-
Fructose is used as a food for diabetic people and may be of particular benefit in diabetic
acidosis.
Infant feeding formulas often contain fructose. When given parenterally, it produces less urinary
secretion than glucose.
Fructose is an ingredient in fructose injection and fructose and sodium chloride injection. These
preparations are fluid, nutrient, and electrolyte replenishers and are administered either
intravenously or subcutaneously, as required.
Fructose is about half again as sweet to the taste as glucose. This is of interest to calorie-
conscious individuals, and the use of high-fructose sweeteners is expanding. High-fructose
sweeteners are prepared by controlled enzymatic isomerization of glucose.
Glucose isomerase from a Streptomyces species is immobilized, and a glucose-containing
solution (derived from starch) is exposed to the enzyme. Highfructose corn syrups containing up
to 90% fructose are available commercially.
4. Lactose:-
Lactose is a tablet diluent. It is less sweet than sucrose and is more easily hydrolyzed.
It is used, therefore, as a nutrient in infants food; it also has a minor role in establishing the
intestinal microflora because it provides the preferred substrate for lactobacilli.
Its principal pharmaceutic use is as an inert diluent for other drugs.
Lactulose is a semisynthetic sugar prepared by alkaline rearrangement of lactose. It yields
fructose and galactose upon hydrolysis. Lactulose is poorly absorbed, and most orally ingested
lactulose reaches the colon unchanged. Bacteria in the colon metabolize the disaccharide to
acetic and lactic acids, and sufficient accumulation of these irritating acids causes a laxative
effect. Although a daily dosage of 10 to 20 g of lactulose is effective in chronic constipa. tion, the
most significant therapeutic use of this sugar is to decrease the blood ammonia concentration in
portal-systemic encephalopathy. The acidified stools trap ammonia as the ammonium ion;
reabsorption is thus prevented, and blood ammonia levels may he decreased by 25 to 50%. The
usual dosage is 20 to 30 g of lactulose as a syrup 3 or 4 times a day.
5. Starch:-
Starch is used as an ingredient in dusting powders and as a pharmaceutic aid. The latter
applications include use as tablet filler, hinder, and disintegrant.
Purified starch amylose is also particularly useful for such purposes. A starch suspension may be
swallowed as an antidote for iodine poisoning.
Starch has many commercial uses, such as paper sizing, cloth sizing, and laundry starching.
It is the starting material from which liquid glucose (corn syrup), dextrose, dextrins, and high-
fructose sweeteners are made.
Pregelatinized starch is starch that has been chemically or mechanically processed to rupture all
or part of the granules in the presence of water. It is subsequently dried. The material may be
modified further to enhance compressibility and flow characteristics. Pregelatinized starch is
slightly soluble to soluble in cold water and is used as a tablet excipient.
Sodium starch glycolate, a semisynthetic material, is the sodium salt of a carboxymethyl ether of
starch. It is used as a disintegrating agent in tablet formulations.
Hetastarch is a semisynthetic material that is prepared in such a manner that it is approximately
90% amylopectiri, and 7 or 8 hydroxyethyl substituents are present for each 10 glucose units. A
6% solution of hetastarch is used as a plasma expander. It is adjunct therapy in treatment of
shock caused by hemorrhage, burns, surgery, sepsis, or other trauma. The duration of the
improved hemodynamic status is 24 to 36 hours. The polymer is degraded, and molecules with
molecular weights of less than 50,000 are eliminated rapidly by renal excretion.
PRESCRIPTION PRODUCT. Hespan®.
6. Cellulose:-
Uses of gum: -
Gums find diverse applications in pharmacy.
They are ingredients in dental and other adhesives and in bulk laxatives but their most frequent
contribution is as agents of pharmaceutics necessity.
These hydrophilic polymers are useful as tablet binders, emulsifiers, gelating agents, suspending
agents, stabilizers, and thickeners.
When problems are encountered in the utilization of hydrocolloids, some alteration in the
hydration of the polymer is usually involved; for example, gums are precipitated from solution
by alcohol and by lead sub-acetate solution.
CLASSIFICATION OF GUMS
The sources of commercially useful gums or hydrocolloids can be classified as follows:
1. Shrub or tree exudates—acacia, karaya, tragacanth
2. Marine gums---agar, algin, and carrageenan
3. Seed gums—guar, locust bean, psyllium
4. Plant extracts--- pectins
5. Starch and cellulose derivatives—hetastarch, carboxymethylcellulose, ethylcellulose,
hydroxypropyl methylcellulose, methylcellulose, oxidized cellulose – already written in cellulose
derivatives
6. Microbial gums—dextrans, xanthan.
MARINE GUMS: -
1. Agar: - Agar is the dried, hydrophilic, colloidal substance extracted from Gelidium
cartilagineum (Fam. Gelidiaceae), Gracilaria confervoides (Fam. Sphaerococcaceae), and related
red algae (Class Rhodophyceae). Agar is sometimes referred to as Japanese isinglas. Agar usually
occurs as bundles consisting of thin, membranous, agglutinated strips or in cut, flaked, or
granulated forms. It may be weak yellowish orange, yellowish gray to pale yellow, or colorless. It
is tough when damp, brittle when dry, odorless or slightly odorous, and has a mucilaginous
taste. Agar is insoluble in cold water, but if one part of agar is boiled for 10 minutes with 65
times its weight of water, it yields a firm gel when cooled.
USES: Agar hydrates to form a smooth, non-irritating hulk that favors normal peristalsis and is
used as a laxative. Agar is also used as a suspending agent, an emulsifier, a gelating agent for
suppositories and surgical lubricants, and a tablet excipient and disintegrant. It is extensively
used as a gel in bacteriologic culture media and as an aid in food processing and other industrial
processes.
2. Algin: Sodium alginate or algin is the purified carbohydrate product extracted from brown
scaweeds by the use of dilute alkali. It is chiefly obtained from Macrocystis pyrifera (Turn.) (barn.
Lcssoniaceae). Algin is found in all species of brown seaweeds (Class Phaeophyceae), and some
commercial algin has been obtained from, among other sources, species of Ascophyllum,
Ecklonia, Laminaria, and Nereocystis. Macrocystis pyrifera is harvested from several temperate
zones of the Pacific Ocean; the area off Southern California is a major producing site.
Algin consists chiefly of the sodium salt of alginic acid, a linear polymer of L-guluronic acid and
D-mannuronic acid. Mannuronic acid is the major component, but there is some variation with
the algal source. The alginic acid molecule appears to be a copolymer of 1,4-linked
mannopyranosyluronic acid units, of 1,4-linked gulopyranosyluronic acid units, and of segments
where these uronic acids alternate with 1,4-linkages.
USES: Sodium alginate is a suspending agent. It is also used in the food industry (ice cream,
chocolate milk, salad dressings, icings, confectionery), for suspending cosmetic preparations, as
a sizing, and for other industrial purposes. Algin is metabolized by the body and has a caloric
value of approximately 1.4 calories per g. The caloric value of the small amount used in most
manufactured products is insignificant.
Seed gums:
1. Guar gum: Guar gum or guaran is the powdered endosperm of the seed of Cyamopsis
tetragonolobus, an annual plant that is readily cultivated in dry climates. Use of this gum is
expanding rapidly, and there is no practical limit on the amount of gum that can be produced by
modern-agricultural practices to meet the demand. The hydrocolloid is galactomannan. 1, 4-
Linked D-mannopyranosyl units form a linear chain; single 1,6-linked D-galactopyranosyl
residues are attached to alternate mannosé moieties. This molecular structure gives properties,
that are intermediate between those typicaIly associated with branched and linear hydrocolloids
The gum hydrates in cold water and is stable in acidic formulations.
USES: Guar gum is used as a bulk-forming laxative and as a thickening agent, a tablet binder,
and a disintegrator in pharmaceuticals. The food processing and paper industries are large users
of this gum.
3. Psyllium:- Plantago seed, psyllium seed, or plantain seed is the cleaned, dried, ripe seed of
Plantago psyllium or of P. indica (P. arenaria), known in commerce as Spanish or French
psyllium seed; or of P. ovata, known in commerce as blonde psyllium or Indian plantago seed.
Plantago seeds contain 10 to 30% of hydrocolloid, which is localized in the outer seed coat. The
hydrocolloid material can be separated into acidic and neutral polysaccharide fractions, and,
upon hydrolysis, L-arabinose, D-galactose, D-galacturonic acid, L-rhamnose, and D-xylose are
obtained. The exact compositions of the polymers have not been determined. Solutions of the
purified gum are thixotropic; the viscosity decreases as shear rate increases, a property that is of
potential value. USES: Plantago seed is a cathartic. Its action is caused by the swelling of the
mucilaginous seed coat, thus giving bulk and lubrication.
PLANT EXTRACTS:
1. PECTINS: Pectin is a purified carbohydrate product obtained from the dilute acid extract of
the inner portion of the rind of citrus fruits or from apple pomace. Pectin is from the Greek and
means congealed or curdled. It is a natural hydrophilic colloid consisting chiefly of partially
methoxylated polygalacturonic acids; the main Carbohydrate component is a linear, 1, 4-linked
D-galacturonan. The molecular weight of pectin ranges from 100,000 to 250,000, Pectin yields
not less than 6.7% of methoxyl groups and not less than 74% of galacturonic acid.
USES: Pectin is classified as a protectant and a suspending agent and is an ingredient in many
antidiarrheal formulations. As a colloidal solution, it has the property of conjugating toxins and
enhancing the physiologic functions of the digestive tract through its physical and chemical
properties, in the upper intestinal tract, pectin possesses a surface area composed of ul
trarnicroscopic particles (micelles) that have the property of colloidal absorption of toxins. The
efficacy of pectin in the gastrointestinal tract is largely owing to this colloidal action.
1. Natural Sweetener: Stevia is known for its intense sweetness, often much sweeter than sugar, while
containing negligible calories. This makes it a popular choice for individuals looking to reduce their sugar
intake or manage their weight.
2. Low Glycemic Index: Unlike sugar, stevia does not raise blood sugar levels, making it suitable for
people with diabetes or those following a low-carb diet.
3. Weight Management: Since stevia provides sweetness without the calories, it can be helpful in weight
management and reducing calorie intake, thus aiding in weight loss efforts.
4. Dental Health: Stevia does not contribute to tooth decay or cavities, unlike sugar, which can be
harmful to dental health. This makes it a preferred sweetener for oral care products and sugar-free
chewing gums.
5. Safe Alternative: Stevia is generally considered safe for consumption, with few reported side effects. It
has been extensively studied for its safety and is approved as a food additive by regulatory agencies in
many countries.
6. Cooking and Baking: Stevia can be used in cooking and baking as a sugar substitute, although its
intense sweetness may require adjustments to recipes. It is available in various forms, including liquid,
powder, and granules, making it versatile for culinary applications.
7. Commercial Products: Stevia is commonly used as an ingredient in a wide range of food and beverage
products, including soft drinks, yogurt, desserts, and condiments, as a natural sweetening agent.
1. Natural Sweetener: Monk fruit extract is significantly sweeter than sugar, making it an attractive
option for those looking to reduce their sugar intake or control their calorie consumption.
2. Zero Calories: Monk fruit extract contains zero calories, which makes it a popular choice for people
who are trying to lose weight or manage their calorie intake.
3. Low Glycemic Index: Monk fruit sweeteners do not raise blood sugar levels, making them suitable for
people with diabetes or those who are following a low-carbohydrate diet.
4. Safe Alternative: Monk fruit sweeteners are generally considered safe for consumption, with few
reported side effects. They have been approved as a food additive by regulatory agencies in many
countries.
5. Natural Origin: Monk fruit sweeteners are derived from the fruit extract and are considered a natural
alternative to artificial sweeteners like aspartame or saccharin.
6. Versatile: Monk fruit sweeteners can be used in a variety of food and beverage products, including
hot and cold beverages, baked goods, desserts, and condiments.
7. No Aftertaste: Unlike some artificial sweeteners, monk fruit sweeteners do not have a bitter or
chemical aftertaste, making them more palatable for many people.
8. Stability in Cooking: Monk fruit sweeteners are stable at high temperatures, making them suitable for
use in cooking and baking applications.
One of the most important differences between artificial sugar substitutes and polyols is that the first
ones contain zero calories, with the exception of aspartame that provides 4 kcal per gram but is
consumed in very small amounts, contributing negligible energy. Sugar alcohols contain from 0.2 to 2.7
calories per gram, while common sugars supply 4 kcal/g.
Unlike artificial sweeteners, polyols can raise blood glucose but less than sugars, which is due to their
incomplete absorption in human organism. However, particular sugar alcohols are metabolized
differently and thus can exhibit various impacts on glucose levels in organism. Polyols are in general
partially digested in the intestines, and the non-absorbed part is slowly metabolized by colonic bacteria
yielding volatile short-chain fatty acids. Most of artificial intense sweeteners are not metabolized
(acesulfame potassium), but aspartame is digested to phenylalanine, aspartic acid and methanol; thus,
people with phenylketonuria, a rare genetic disorder, cannot consume products sweetened with this
substance.
The sweetness of sugar alcohols varies from 25 to 100 % as compared with table sugar, whereas artificial
sweeteners are 30 to even 13,000 times sweeter than sucrose. Thus, they can be used in small amounts
to achieve desired sweetness in such products as beverages, ice cream chewing gum, chocolate,
jams/jellies, yogurt and salad dressings. However, artificial intense sweeteners are used only for
sweetening, whereas polyols can be used as anti-caking and glazing agents as well as stabilizers and
thickeners. Similar to common sugars, they can be also used as bulking agents besides being excellent
natural sweeteners. They also help food keep moisture, prevent browning when heated and add a
cooling sensation to products. Some artificial sweeteners may leave an aftertaste, but mixing with
particular polyols such as erythritol, isomalt or lactitol can result in a similar flavor to the one of table
sugar.
All in all, both groups of sweeteners can be useful in diabetes management and are good option for
people on lowcarbohydrate diet. The highest polyol intake can be associated with consumption of
confectionery products, fish/meat product and miscellaneous foods. However, such estimates might
differ in dependence on scenario adopted for exposure modeling. Overconsumption of polyols can be
only of concern in view of digestive comfort, while artificial sweeteners must be always estimated with
respect to the maximum amounts allowed, which are considered safe for human consumption.
Therefore, it might be worth using sugar alcohols in food products marketed to patients with diabetes
and individuals considering energy restricted diets more frequently but bearing in mind their
gastrointestinal effects. However, optimal diet should be based on fresh unprocessed foods with the
minimal amounts of food additives, and then the sugar replacers such as sugar alcohols or even artificial
sweeteners will not have a significant role in the daily diet.