You are on page 1of 33

PHARM.

D Chemical Pharmacognosy- I Lecture 1 February 17, 2011

CARBOHYDRATES SUCROSE
M. Ahsan Khalid, B.Pharm, Pharm. D B.Pharm,
M.Phil Scholar (RIPS/RIU) HIPSHIPS-HUKIC

Carbohydrates (glycans) have the following


basic composition:
(CH2O)n

There are a variety of interrelated classification schemes. The most useful classification scheme divides the carbohydrates into groups according to the number of individual simple sugar units.

I or H - C - OH I

Monosaccharides - simple sugars with multiple OH groups. Based on number of carbons (3, 4, 5, 6), a monosaccharide is a triose, tetrose, pentose or hexose. Disaccharides - 2 monosaccharides covalently linked. Oligosaccharides - a few monosaccharides covalently linked. Polysaccharides - polymers consisting of chains of monosaccharide or disaccharide units.

Monosaccharides
Aldoses (e.g., glucose) have Ketoses (e.g., fructose) have an aldehyde group at one end. a keto group, usually at C2.
H C H HO H H C C C C OH H OH OH
HO H H

O
CH2OH C C C C O H OH OH

CH2OH

CH2OH

D-glucose

D-fructose

Monosaccharides
Glucose Galactose From Greek word for sweet wine; grape sugar, blood sugar, dextrose. Greek word for milk--"galact", found as a component of lactose in milk. Latin word for fruit--"fructus", also known as levulose, found in fruits and honey; sweetest sugar. Ribose and Deoxyribose are found in the backbone structure of RNA and DNA, respectively.

Fructose

Ribose

Hemiacetal & hemiketal formation


H H O

An aldehyde can react with an alcohol to form a hemiacetal. A ketone can react with an alcohol to form a hemiketal.

C R

R'

OH

R'

C R

OH

aldehyde
R C R' O

alcohol

hemiacetal
R

"R

OH

"R

C R'

OH

ketone

alcohol

hemiketal

Disaccharides:
Maltose, a cleavage product of starch (e.g., amylose), is a disaccharide with an a(1 4) glycosidic link between C1 - C4 OH of 2 glucoses. It is the a anomer (C1 O points down).

6 CH2OH

6 CH2OH

H
4

O H
2 1

H
4

O H
2 1

H OH
3

H OH
3

OH

OH

H
6 CH2OH

OH

maltose

H
6 CH2OH

OH

H
4

O H
2 1

H O H
4

O H
2 1

OH

H OH
3

H OH
3

OH

OH

cellobiose

OH

Cellobiose, a product of cellulose breakdown, is the otherwise equivalent b anomer (O on C1 points up). The b(1 4) glycosidic linkage is represented as a zig-zag, but one glucose is actually flipped over relative to the other.

Other disaccharides include: Sucrose, common table sugar, has a glycosidic bond linking the anomeric hydroxyls of glucose & fructose. Because the configuration at the anomeric C of glucose is a (O points down from ring), the linkage is a(12). The full name of sucrose is a-D-glucopyranosyl-(12)b-D-fructopyranose.) Lactose, milk sugar, is composed of galactose & glucose, with b(14) linkage from the anomeric OH of galactose. Its full name is b-D-galactopyranosyl-(1 4)a-D-glucopyranose

Disaccharides - contain two monosaccharides


Sucrose French word for sugar--"sucre", a disaccharide containing glucose and fructose; table sugar, cane sugar, beet sugar. Latin word for milk--"lact"; a disaccharide found in milk containing glucose and galactose.

Lactose

Maltose

French word for "malt"; a disaccharide containing two units of glucose; found in germinating grains, used to make beer.

CH2OH H OH H OH O H OH H
1

H O

6CH OH 2 5 O 4 OH 3

CH2OH H O H O H OH H H O OH H H

CH2OH O H OH H H OH H O H

CH2OH O H OH H H OH OH H

H 1
2

OH

amylose

Polysaccharides:
Plants store glucose as amylose or amylopectin, glucose polymers collectively called starch. Glucose storage in polymeric form minimizes osmotic effects. Amylose is a glucose polymer with a(14) linkages. The end of the polysaccharide with an anomeric C1 not involved in a glycosidic bond is called the reducing end.

CH2OH H H OH OH H CH2OH H OH H OH O H OH H H O H OH CH2OH O H OH H H O H H O H

CH2OH O H OH H H OH H 1 O 6 CH2 5 H OH 3 H CH2OH O H 2 OH 1 O H H O H 4 OH H H

amylopectin

CH2OH H O OH H O H OH H H OH OH H

H O

H 4

OH

Amylopectin is a glucose polymer with mainly a(14) linkages, but it also has branches formed by a(16) linkages. Branches are generally longer than shown above. The branches produce a compact structure & provide multiple chain ends at which enzymatic cleavage can occur.

CH2OH H H OH OH H CH2OH H OH H OH O H OH H H O H OH CH2OH O H OH H H O H H O H

CH2OH O H OH H H OH H 1 O 6 CH2 5 H OH 3 H CH2OH O H 2 OH 1 O H H H 4 OH H O H O OH H H

glycogen

CH2OH O H OH H H OH OH H

H O

H 4

OH

Glycogen, the glucose storage polymer in animals, is similar in structure to amylopectin. But glycogen has more a(16) branches. The highly branched structure permits rapid glucose release from glycogen stores, e.g., in muscle during exercise. The ability to rapidly mobilize glucose is more essential to animals than to plants.

CH2OH H OH H OH O H OH H
1

H O H

6CH OH 2 5 O 4 OH 3

CH2OH H O H H OH O H OH H H O H

CH2OH O H OH H H H OH O H

CH2OH O H OH H H H OH OH

H 1
2

OH

cellulose

Cellulose, a major constituent of plant cell walls, consists of long linear chains of glucose with b(14) linkages. Every other glucose is flipped over, due to b linkages. This promotes intra-chain and inter-chain H-bonds and van der Waals interactions, that cause cellulose chains to be straight & rigid, and pack with a crystalline arrangement in thick bundles - microfibrils. See: Botany online website; Schematic of arrangement of cellulose chains in a microfibril. website at Georgia Tech.

CH2OH H OH H OH O H OH H
1

H O H

6CH OH 2 5 O 4 OH 3

CH2OH H O H H OH O H OH H H O H

CH2OH O H OH H H H OH O H

CH2OH O H OH H H H OH OH

H 1
2

OH

cellulose

Multisubunit Cellulose Synthase complexes in the plasma membrane spin out from the cell surface microfibrils consisting of 36 parallel, interacting cellulose chains. These microfibrils are very strong. The role of cellulose is to impart strength and rigidity to plant cell walls, which can withstand high hydrostatic pressure gradients. Osmotic swelling is prevented. Explore and compare structures of amylose & cellulose using Chime.

Common Polysaccharides Name Source


Starch Plants store glucose as the polysaccharide starch. The cereal grains (wheat, rice, corn, oats, barley) as well as tubers such as potatoes are rich in starch.

Cellulose

The major component in the rigid cell walls in plants is cellulose and is a linear polysaccharide polymer with many glucose monosaccharide units.

Glycogen

This is the storage form of glucose in animals and humans which is analogous to the starch in plants. Glycogen is synthesized and stored mainly in the liver and the muscles.

Sucrose is made from glucose and fructose units: Sucrose or table sugar is obtained from sugar cane or sugar beets. The glucose and fructose units are joined by an acetal oxygen bridge in the alpha orientation.

Invert Sugar: When sucrose is hydrolyzed it forms a 1:1 mixture of glucose and fructose. This mixture is the main ingredient in honey. It is called invert sugar because the angle of the specific rotation of the plain polarized light changes from a positive to a negative value due to the presence of the optical isomers of the mixture of glucose and fructose sugars.

Hydrolysis of Sucrose:

In the hydrolysis of any di- or polysaccharide, a water molecule helps to break the acetal bond. The acetal bond is broken, the H from the water is added to the oxygen on the glucose. The -OH is then added to the carbon on the fructose.

Synthesis and Biosynthesis of Sucrose


The biosynthesis of sucrose proceeds via the precursors UDP-glucose and fructose 6-phosphate, catalyzed by the enzyme sucrose-6phosphate synthase. The energy for the reaction is gained by the cleavage of Uridine diphosphate (UDP). Sucrose is formed by plants but not by other organisms. Sucrose is found naturally in many food plants along with the monosaccharide fructose. In many fruits, such as pineapple and apricot, sucrose is the main sugar. In others, such as grapes and pears, fructose is the main sugar.

The prodution of sucrose takes place in plants, to store energy produced during photosynthesis. The extraction of sucrose from plants like sugar cane and sugar beets is used to produce sugar for consumption, making this pathway of significant economic interest. The starting point for sucrose synthesis is activated glucose, UDPglucose. UDP-glucose used in sucrose synthesis is derived from glucose-1-phosphate, which is itself derived from photosynthetic products. The fructose-6-phosphate involved in sucrose synthesis is also derived from photosynthetic products. The enzyme sucrose 6phosphate synthase is regulated in several ways. Glucose-6-phosphate activates this enzyme, and dephosphorylation of this enzyme in light also activates sucrose 6phosphate synthase, coordinating sucrose synthesis with photosynthesis.

PRODUCTION
Sugar or more specifically sucrose is a carbohydrate that occurs naturally in every fruit and vegetable. It is the major product of photosynthesis, the process by which plants transform the sun's energy into food.

Sugar occurs in greatest quantities in sugar cane and sugar beets from which it is separated for commercial use.

In the first stage of processing the natural sugar stored in the cane stalk or beet root is separated from the rest of the plant material by physical methods. For Sugar Cane, this is accomplished by: a) pressing the cane to extract the juice containing the sugar b) boiling the juice until it begins to thicken and sugar begins to crystallize c) spinning the sugar crystals in a centrifuge to remove the syrup, producing raw sugar; the raw sugar still contains many impurities d) shipping the raw sugar to a refinery where it is washed and filtered to remove remaining non-sugar ingredients and color e) crystallizing, drying and packaging the refined sugar.

Beet sugar processing is similar, but it is done in one continuous process without the raw sugar stage.

The sugar beets are washed, sliced and soaked in hot water to separate the sugar-containing juice from the beet fiber. The sugar-laden juice is purified, filtered, concentrated and dried in a series of steps similar to cane sugar processing.

CANE VERSUS BEET The production of sugarcane needs approximately four times as much water as the production of sugar beet, On the other hand, sugar cane tolerates hot climates better. The production of sugar results in residues that differ substantially depending on the raw materials used and on the place of production.

While cooks often use cane molasses in food preparation, humans find molasses from sugar beet unpalatable, and it, therefore, ends up mostly as industrial fermentation feedstock (for example in alcohol distilleries), or as animal feed. Once dried, either type of molasses can serve as fuel for burning.

Health Hazards
Tooth Decay Glycemic Index Diabetes Gout

Tooth Decay
the most prominent health hazard associated with the consumption of sugar Oral bacteria such as Streptococcus mutans live in dental plaque and metabolize any sugars (not just sucrose, but also glucose, lactose, fructose, or cooked starches) into lactic acid. High concentrations of acid may result on the surface of a tooth, leading to tooth demineralization

Glycemic Index
Sucrose has a moderately high glycemic index (64, about the same as honey, 62, but not nearly that of maltose, 105), which, in turn, causes an immediate response within the body's digestive system Like other sugars, sucrose is digested into glucose (blood sugar) and transported into the blood overconsumption may cause an increase in blood sugar levels from a normal 90 mg/dL to up over 150 mg/dL.

Diabetes
Type 1 diabetes & Type 2 diabetes Glucose build up in the bloodstream can cause two problems: in the short term, cells become starved for energy because they do not have access to the glucose in the long term, frequent glucose build-up increases the acidity of the blood, damaging many of the body's organs, including the eyes, kidneys, nerves and/or heart

Gout
The occurrence of gout is connected with an excess production of uric acid. A diet rich in sucrose may lead to gout as it raises the level of insulin, which prevents excretion of uric acid from the body. As the concentration of uric acid in the body increases, so does the concentration of uric acid in the joint liquid and beyond a critical concentration, the uric acid begins to precipitate into crystals. Researchers have implicated sugary drinks high in fructose in a surge in cases of gout

You might also like