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Big Picture in Focus: ULO2. Demonstrate knowledge on

carbohydrates’ structure, functions, classification, physicochemical
properties, and its clinical significance.

Metalanguage
The most essential terms and concepts below are defined, for you to have a better understanding of this
section in the course. You are advised to frequently refer to these definitions to help you understand the succeeding
topics.

1. Biochemistry – Biochemistry is the study of the chemical substances found in living systems and the chemical
interactions of these substances with each other.

2. Carbohydrates – Carbohydrates are polyhydroxy aldehydes, polyhydroxy ketones, or compounds that yield such
substances upon hydrolysis. Plants contain large quantities of carbohydrates produced via photosynthesis.

3. Chirality and achirality – A chiral object is not identical to its mirror image. An achiral object is identical to its
mirror image.

4. Chiral center – A chiral center is an atom in a molecule that has four different groups tetrahedrally bonded to it.
Molecules that contain a single chiral center exist in a left-handed and a right-handed form.

5. Stereoisomerism – The atoms of stereoisomers are connected in the same way but are arranged differently in
space. The major causes of stereoisomerism in molecules are structural rigidity and the presence of a chiral center.

6. Enantiomers and diastereomers – 2 types of stereoisomers exist: enantiomers and diastereomers. Enantiomers
have structures that are nonsuperimposable mirror images of each other. Enantiomers have identical achiral
properties, but different chiral properties. Diastereomers have structures that are not mirror images of each other.

7. Fischer projection formulas – Fischer projection formulas are two-dimensional structural formulas used to depict
the three-dimensional shapes of molecules with chiral centers.

8. Optical activity – Chiral compounds are optically active – that is, they rotate the plane of polarized light.
Enantiomers rotate the plane of polarized light in opposite directions. The prefix (+) in a clockwise direction, whereas
compounds that rotate the plane of polarized light in a counterclockwise direction have the prefix (-).

9. Cyclic monosaccharides – Cyclic monosaccharides form through an intermolecular reaction between the carbonyl
group and an alcohol group of an open-chain monosaccharide. These cyclic forms predominate in solution.

10. Haworth projection formulas – Haworth projection formulas are two-dimensional structural representations
used to depict the three-dimensional structure of a cyclic form of a monosaccharide.

11. Important monosaccharides – Important monosaccharides include glucose, galactose, fructose, and ribose.
Glucose and galactose are aldohexoses, fructose is a ketohexose, and ribose is an aldopentose.

Reference textbook: Stoker, H. S. (2017). Biochemistry 3rd Edition. C & E Publishing Inc. Quezon City. 1
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12. Reactions of monosaccharides – Five important reactions of monosaccharides are (1) oxidation to an acidic
sugar, (2) reduction to a sugar alcohol, (3) glycoside formation, (4) phosphate ester formation, and (5) amino sugar
formation.

13. Glycolipids and glycoproteins – Glycolipids and glycoproteins are molecules in which oligosaccharides are
attached through glycosidic linkages to lipids and proteins, respectively. Such molecules often govern how cells of
differing function interact with each other.

Essential Knowledge

Carbohydrates – Structure and Function

Carbohydrates
• The most abundant class of bioorganic molecules on earth.
• Produced by the photosynthetic activity of the green plants.
• Also referred to as saccharides because of the sweet taste of many carbohydrates.
• (Latin, saccharum, meaning sugar)
• Storehouse of chemical energy (glucose, starch, glycogen)
– a gram of digested carbohydrate gives about 4 kcal of energy
– complex carbohydrates are best for diet
• Supportive structural components in plants and some animals (cellulose, chitin).
• Form part of the structural framework of DNA & RNA.
• Carbohydrate “markers” on cell surfaces play key roles in cell-cell recognition processes.

Classification of Carbohydrates
• Simpler Formula: CnH2nOn or Cn(H2O)n where n= number of atoms
• Polyhydroxy aldehydes or polyhydroxy ketones or compounds that produce such substances upon
hydrolysis.

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Classification Based on Products of Acid Hydrolysis

Monosaccharides
• The simple sugars.
• Contain a single polyhydroxy aldehyde or polyhydroxy ketone unit.
• Cannot be degraded into simpler products by hydrolysis reactions.
• Pure monosaccharides are water-soluble, white, crystalline solids.

Disaccharides
• Contains 2 monosaccharide units covalently bonded to each other.
• Crystalline and water-soluble substances.
• Upon hydrolysis they produce monosaccharides.

Oligosaccharides
• Contains 2-10 monosaccharide units - covalently bonded.
• Disaccharides are the most common type.
• Trisaccharides (raffinose)
• Tetrasaccharides (stachyose)
• Free oligosaccharides, other than disaccharides, are less common in nature.
• Usually found associated with proteins and lipids in complex molecules that serve structural and regulatory
functions.

Polysaccharides
• Consist of tens of thousands of monosaccharide units covalently bonded.
• Homopolysaccharides – polymers of a single monosaccharide (glycogen, cellulose, starch).
• Heteropolysaccharides – contain more than one kind of monosaccharide (hyaluronic acid, heparin,
chondroitin sulfate).

Derived Carbohydrates
• Those where carbohydrate moieties have undergone some reactions converting them into other products.
• Sugar acids, sugar alcohols, deoxysugars, and sugar amines.

Classification of Monosaccharides
• Carbohydrates that have the general formula CnH2nOn
– n varies from 3 – 8.
• Grouped together according to the number of carbons they contain.
– C3H6O3 triose
– C4H8O4 tetrose
– C5H10O5 pentose
– C6H12O6 hexose
– C7H14O7 heptose
– C8H16O8 octose
• May either be:
– An aldose – contains aldehyde group
– A ketose – contains ketone group
– Presence of a ketone group is usually indicated by using the ending “ ulose” in naming the
sugar (e.g., levulose).

Reference textbook: Stoker, H. S. (2017). Biochemistry 3rd Edition. C & E Publishing Inc. Quezon City. 3
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Trioses
• The parent member of the family of monosaccharides.
• From them emanates the other members of the monosaccharide family.
• The final form of carbohydrate into which all carbohydrates, regardless of their complexity, are degraded
in the body during carbohydrate metabolism.
• D (+)- glyceraldehyde
– an aldotriose
• Dihydroxyacetone
– a ketotriose

Pentoses
• Aldopentoses
– D-(-)-xylose
o a constituent of the heart muscle
– D-(-)-ribose
o ribose and 2-deoxyribose – present as intermediates in metabolic pathways and are
important building blocks of RNA and DNA
• Ketopentoses
– D-ribulose
– D-xylulose

Hexoses
• The most common of all the monosaccharides.
• Aldohexoses
– D-(+)-mannose
– D-(+)-glucose
o A 5% (m/v) glucose solution is often used in hospitals as an intravenous source of
nourishment for patients who cannot take food by mouth.
– D-(+)-galactose
• Ketohexose
– D-(-)-fructose

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• Monosaccharides can be classified based on their spatial orientation (stereochemistry).

• A monosaccharide can be classified as a D or L isomer, depending on the spatial orientation of the –H and
–OH groups attached to the carbon atom adjacent to the terminal primary alcohol group.
• The D isomer is represented when the –OH is written to the right of this carbon in the Fischer projection
formula. The L isomer is represented when this –OH is written to the left.

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Biochemically Important Monosaccharides

Glucose
1. Most abundant in nature.
2. Nutritionally most important.
3. Grape fruit good source of glucose (20 - 30% by mass) -- also named grape sugar, dextrose and blood sugar (70 -
100 mg/100 mL of blood).
4. Six membered cyclic form.

Fructose
1. Ketohexose
2. Sweetest of all sugars; the fruit sugar.
3. Found in many fruits and in honey.
4. Good dietary sugar-- due to higher
Sweetness.
5. Five membered cyclic form.

Galactose
1. A component of milk sugar.
2. Synthesized in human.
3. Also called brain sugar-- part of brain and nerve tissue.
4. Used to differentiate between blood types.
5. Six membered cyclic form.
6. Galactosemia - a result of genetic deficiency in the infant – the gene responsible for the enzyme that converts D-
galactose to D-glucose. Such infants cannot metabolize galactose and it builds up in the blood and tissue.

Ribose
1. Part of RNA.
2. Part of ATP.
3. Part of DNA.
4. Five membered cyclic form.

Reference textbook: Stoker, H. S. (2017). Biochemistry 3rd Edition. C & E Publishing Inc. Quezon City. 6
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Cyclic Forms of Monosaccharides

Hemiacetals and Hemiketals

• The dominant form of monosaccharides with 5 or more C atoms is cyclic.
• Hemiacetals and hemiketals are formed from the reaction between two functional groups: aldehyde or
ketone and alcohol
– May take place either intermolecularly or intramolecularly as in the case of sugars, provided there
are sufficient number of carbons between the aldehyde or ketone and the alcohol group to permit
a stable ring formation.
– Five- or six-membered hemiacetal rings are stable.
• Two types of ring structures are possible:
– Five-membered ring, or furanose ring, derived from parent compound furan.
– Six-membered ring, or pyranose ring, derived from parent compound pyran.

Cyclic Hemiacetal Forms of D-Glucose

• In the cyclic hemiacetals of glucose, C1*, is now a chiral center (an anomeric carbon).
– two anomers of D-glucose: -D- glucose & -D-glucose
• The cyclic hemiacetals are readily interconvertible in aqueous solution.
– This interconversion of - and - anomers in solution is accompanied by a change in specific
rotation called MUTAROTATION.
– Only sugars that form hemiacetal or hemiketal structure mutarotate.

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• 2 anomeric forms of D- glucose:

– Alpha-form: -OH of C1 and CH2OH of C5 are on opposite sides
– Beta-form: -OH of C1 and CH2OH of C5 are on same sides
• Anomers: Cyclic monosaccharides that differ only in the position of the substituents on the anomeric
carbon atom.
• Any —OH group at a chiral center that is to the right in a Fischer projection formula points down in the
Haworth projection formula and any —OH group to the left in a Fischer projection formula points up in the
Haworth projection formula.

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Disaccharides
• The two monosaccharides are linked together by acetal formation to form disaccharide.
• One monosaccharide act as a hemiacetal and other as alcohol and the resulting ether bond is a glycosidic
linkage.
• Condensation of the hydroxyl function of the hemiacetal group of one monosaccharide with the hydroxyl
group of another monosaccharide forms the bond, called a glycosidic bond, joining the 2 saccharide units.

Maltose
• Malt sugar, found in corn syrup, malt, and germinating seeds.
• consists of two molecules of glucose joined by a-1,4-glycosidic bond.
– -1,4-glycosidic bond means that the first sugar is in -configuration and its C#1 is linked to C#4 of the
second sugar component.
– The second sugar may be either an α- or a β-anomer.

Reference textbook: Stoker, H. S. (2017). Biochemistry 3rd Edition. C & E Publishing Inc. Quezon City. 9
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Cellobiose
• One of the major fragments isolated after extensive hydrolysis of cellulose.
• The 2 glucose units are joined by a β-1,4-glycosidic linkage.
• Maltose is digested easily by humans because we have enzymes that can break α-(1→ 4) linkages but not
β-(1→ 4) linkages of cellobiose.

Lactose
• Milk sugar
– Human - 7%–8% lactose
– Cow’s milk - 4%–5% lactose
• Consists of β-galactose with a β-1,4-glycosidic linkage to β -glucose (or α -glucose).
• Lactose intolerance: a condition in which people lack the enzyme lactase needed to hydrolyze lactose to
galactose and glucose.
• Lactose intolerance is unpleasant, but its effects can be avoided by a diet that rigorously excluded milk and
milk products.

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Lactose intolerance vs Galactosemia

• When undigested, lactose attracts water causing fullness, discomfort, cramping, nausea, and diarrhea.
• Bacterial fermentation of lactose along the intestinal tract produces acid (lactic acid) and gas, adding to
the discomfort.
• Galactosemia: the genetic disease caused by the absence of the enzymes needed for conversion of
galactose to glucose.
• A reduced form of galactose, called dulcitol (galactitol), a toxic metabolite, is produced and accumulates.
• It can lead to severe mental retardation, cataracts, and early deaths.

Sucrose
• The common table sugar & the most abundant of all disaccharides found in plants.
• Produced commercially from the juice of sugar cane and sugar beets.
• The α-anomeric carbon 1 of glucose joins the β-anomeric carbon 2 of fructose (α-1,2-glycosidic bond)

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Invert Sugar
• Optical activities:
– Sucrose : +66.5
– Glucose : +53
– Fructose : -92
– Invert sugar : -39
• Invert sugar has a much greater tendency to remain in solution.
• In the manufacture of jelly and candy and in the canning of fruit, crystallization of the sugar is undesirable,
therefore conditions leading to the hydrolysis of sucrose are employed in these processes; in addition,
fructose is sweeter than sucrose.
• Honeybees and many other insects possess an enzyme called invertase that hydrolyzes sucrose to invert
sugar.
• Thus honey is predominantly a mixture of D-glucose and D-fructose with some unhydrolyzed sucrose.

Artificial Sweeteners

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Oligosaccharides
• Commonly found in onions, cabbage, broccoli and wheat.
• In humans, intestinal bacteria action on the undigestable raffinose and stachyose present in beans produces
gaseous products that can cause discomfort and flatulence.

Solanin
• A potato toxin, is a oligosaccharide found in association with an alkaloid.
• Bitter taste of potatoes is due to relatively higher levels of solanin.

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General Characteristics of Polysaccharides

The Polymer Chain

• Many monosaccharide units bonded with glycosidic linkages.
• Branched or unbranched.
• Homopolysaccharide or heteropolysaccharides.
• Alternate name is glycan.
• Not sweet and don’t show positive tests with Tollen’s and Benedict’s solutions.
• Limited water solubility.

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Storage polysaccharides Homopolysaccharides

– starch – starch
– glycogen – glycogen
– cellulose
Structural polysaccharides – chitin
– cellulose – carrageenan
– chitin
– carrageenan Heteropolysaccharides
– hyaluronic acid
Acidic polysaccharides – heparin
– heparin – chondroitin sulfate
– hyaluronic acid – alginic acid
– alginic acid
– chondroitin sulfate

Storage Polysaccharides

Starch
• The chief caloric distributor in the diet; the reserve carbohydrates for plants.
• Amylose - straight chain polymer; 15-20% of the starch; water-soluble fraction; 60-300 glucose units joined
by α -1,4-glycosidic bonds.
• Experimental evidence indicates that the molecule is actually coiled like a spring and is not a straight chain
of glucose units.
• When coiled in this fashion the molecule has just enough room in its core to accommodate an iodine
molecule.
• The characteristic blue color that starch gives when treated with iodine is due to the formation of the
amylose-I2 complex.

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• Amylopectin
– Branched chain polymer.
– 80 - 85% of the starch.
– The water-insoluble fraction.
– Composed of 300-6000 glucose units joined primarily by α-1,4- glycosidic bonds and occasionally
by α-1,6- glycosidic bonds.
– α 1,6 bonds are responsible for branching which occurs about once every 25-30 units.

Glycogen
• The animal starch.
• Glucose storage molecule of animals.
• Stored in granules in liver and muscle cells.
• Like amylopectin, is a nonlinear polymer of glucose units joined by α-1,4- and α-1,6-glycosidic bonds but
has lower molecular weight.
• More highly branched structure.
• Its branches are shorter.
• Gives red-brown color with I2.

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Structural Polysaccharides

Cellulose
• A fibrous carbohydrate found in all plants where it serves as the structural component of the plant’s cell
wall.
• A linear polymer of glucose units joined by β-1,4-glycosidic bonds.
• Linear nature of chains allows close packing into fibers, making it difficult for solvent molecules to pull the
chains apart, thus cellulose is inert towards most solvents.
• Cotton ~95% cellulose and wood ~50% cellulose.
• It serves as dietary fiber in food-- readily absorbs water and results in softer stools.
• 20-35 g of dietary fiber is desired every day.

Cellulose
• Yields D-glucose upon hydrolysis yet man & the carnivorous animals can’t utilize cellulose as a source of
glucose.
• Human‘s digestive juices lack the enzyme cellulase that hydrolyze β-1,4-glycosidic linkages.
• Ruminants (cows, goats) and termites have, within their digestive tracts, microorganisms that produce
cellulase

Reference textbook: Stoker, H. S. (2017). Biochemistry 3rd Edition. C & E Publishing Inc. Quezon City. 17
 College of Health Sciences Education
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Chitin
• Similar to cellulose in both function and structure.
• Polymer of N-acetyl-D- glucosamine bound by β-1 → 4 glycosidic linkages (has a linear extended structure
like cellulose).
• Function is to give rigidity to the exoskeletons of crabs, lobsters, shrimp, insects, and other arthropods.
• It is inert and practically insoluble in most solvents. Its derivative, chitosan, can be prepared by simple
alkali-catalyzed deacylation. Chitosan derivatives are commercially used as films, fibers, surface coatings
and ultrafiltration membranes.

Carrageenan
• Occurs as hydrocolloid extracted from selected species of red algae.
• Locally obtained from Eucheuma striatum, Eucheuma spinosum and Acanthapora.
• Sulphated polysaccharides, consisting of polymers of sulphated D-galactopyranose bonded through
alternating α-1 → 3 and β-1 → 4 glycosidic linkages.
• Widely used in food industry.
• Its gelling property is used in enhancing the texture of various dairy products and in preventing oiling off
in caramel and toffee during hot weather.
• Also serve as coating to retard moisture loss from foods and fresh produce like fruits and vegetables.

Reference textbook: Stoker, H. S. (2017). Biochemistry 3rd Edition. C & E Publishing Inc. Quezon City. 18
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Acidic Polysaccharides

Hyaluronic acid
• Repeating unit is a disaccharide composed of b-D-glucuronic acid and N-acetyl-D-glucosamine in a β-(1 →
3)-linkage.
• Each disaccharide is attached to the next by β-(1 → 4)-linkage.
• Alternating β-(1 → 3) and β-(1 → 4)- linkages.
• Highly viscous - serve as lubricants in the fluid of joints and part of vitreous humor of the eye.
• When some insects sting, they inject an enzyme called hyaluronidase, which breaks hyaluronic acid linkages
and facilitates the spread of the venom.

Heparin
• Consists of repeating units of D-glucuronic acid and D-glucosamine.
• An anticoagulant in blood that inhibits blood clot formation.
• Used in open-heart surgery.

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Alginic acid
• Locally extracted from Sargassum seaweeds.
• Consist of repeating units of β-1 → 4 bonded mannuronic and α-1 → 4 bonded L-guluronic acid; cell wall
material.
• Serves as base coatings in meats and fish which reduces moisture loss and fat absorption.

Chondroitin sulfate
• Consists of repeating units of D-glucuronic acid-D-glucosamine sulfate.
• Structural role in cartilage, bone, and cornea of the eye.

Dietary Considerations and Carbohydrates

Glycemic Foods
• A developing concern about intake of carbohydrates involves how fast the given dietary carbohydrates are
broken down to glucose within the human body.
• Glycemic index refers to:
– how quickly carbohydrates are digested
– how high blood glucose rises
– how quickly blood glucose levels return to normal
• Glycemic index (GI) has been developed for rating foods.
• Low-GI foods are desirable.

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GI- 0-100 assigned to food

Represents the relative rise in the blood glucose level two hours after consuming that food.
Low- less than 55, Medium- 56-69, High- 70 and up

Unavailable Carbohydrates
• Those not hydrolyzed by digestive enzymes.
• They constitute the dietary fiber.
• Fiber in the diet aids in the formation of bulk in the intestinal tract, which increases the absorption of water
along the tract.
• Dietary fiber, as it reaches the gut, is intact in structure where they form a meshwork.
• The meshwork has spaces where fecal matter and water are trapped.
• The effect is soft fecal matter which can be easily removed.
• If absent fecal matter is hard, and has a long transit time.
• Long sojourn will dehydrate it and will make it harder to remove.
• It also increases the rate at which digestive wastes move through the intestinal tract, which lessens the time
the intestine comes in contact with any ingested carcinogens.
• Some forms of diverticulitis (inflammation of the colon) have been relieved by increasing the quantity of
fiber in the diet.
• Straining at stool because of lack of dietary fiber can lead to hemorrhoids and nervous disorders.

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Edible Fibers and Health

Edible fibers, that is, nondigestible carbohydrates, can be classified in two different ways. In the first
classification system there are two types of edible fibers: functional fiber and dietary fiber. Distinguishing
characteristics for these two types of fibers are as follows:

1. Functional fiber is nondigestible carbohydrate materials that have been produced commercially for use in
fortifying foods or in fiber supplements. Most often they are carbohydrate materials extracted from foods. Examples
of such fibers are psyllium and pectin.

2. Dietary fiber is nondigestible carbohydrate materials that are used intact as they occur naturally in foods. Many
sources for such fiber exist including cellulose from plant materials (celery “strings,” the outer layer of whole grain
[bran], etc.), and the nondigestible starch components of dried beans (raffinose and stachyose).

In the second classification system for edible fibers, classification is based on how the fiber interacts with
water. Edible fibers are either insoluble or soluble.

1. Insoluble fiber is nondigestible carbohydrate materials, that do not form viscous materials that is, materials that
have a gel-like consistency in water. Also, in general, insoluble fibers are not readily fermented by bacteria in the
human intestinal tract. The skin of fruits and vegetable are examples of insoluble fibers.

2. Soluble fiber is nondigestible carbohydrate materials that dissolve in water to produce thick liquids with a gel-like
consistency. An example is pectin from fruit, which is used to thicken jellies. In general, bacteria in the human
intestinal tract readily ferment soluble fibers, producing intestinal gas.

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Dietary Fiber
• Lack of dietary fiber may also lead to overnutrition.
• When one does not masticate, the secretion of digestive hormones (such as gastrin and cholecystokinin) is
not induced.
• Without these hormones, it takes longer to reach the feeling of satiety.
• Dietary fiber may also be beneficial in weight maintenance.
• Fiber increases the bulk in the stomach and intestines without contributing to the caloric intake.
• There is also a correlation between ischemic heart disease and gallstone formation with the lack of dietary
fiber.
• Cholesterol can be trapped in the meshwork reducing the concentration of blood cholesterol.
• With dietary fiber, bile will not be supersaturated with cholesterol.
• In its absence, bile will be supersaturated with cholesterol and gallstone formation results.
• When cholesterol is trapped plaque formation will be reduced.
• In the absence of dietary fiber, excess cholesterol can lead to plaque formation leading to ischemic heart
disorders.
• About 20-35 grams of dietary fiber daily is a desirable intake.

-END-

GOOD JOB!

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Keywords Index
Carbohydrates Polysaccharides Fructose Hemiketals
Monosaccharides Aldose Galactose Fischer Projection
Disaccharides Ketose Ribose Haworth Projection
Oligosaccharides Glucose Hemiacetals Anomer
Epimer Maltose Lactose Lactose intolerance
Glycosidic bond Cellobiose Galactosemia Sucrose
Invert sugar Artificial sweeteners Raffinose Stachyose
Solanin Glycan Glycogen Heparin
Polymer chain Starch Cellulose Chitin
Hyaluronic acid Alginic acid Chondroitin sulfate Insoluble fiber
Amylose Carrageenan Dietary fiber Soluble fiber
Amylopectin Glycemic index Functional fiber Glycemic foods

Reference textbook: Stoker, H. S. (2017). Biochemistry 3rd Edition. C & E Publishing Inc. Quezon City. 24