CARBOHYDRATES AND RELATED COMPOUNDS

Carbohydrates (CHO)
Aldehyde/ ketone alcohols
First products formed in photosynthesis
2 broad groups:
Sugars
- monosaccharides, disaccharids, trisaccharides,
tetrasaccharides, etc.
- trioses: 3 carbon atome; tetroses (4) ; pentoses
(5) ; hexoses (6), etc.
- crystalline, soluble in water, sweet
Polysaccharides
- more complex, high molecular weight
- example: starch, inulin, celluloses
- can usually be hydrolyzed to a component
hexose (hexosans); starch, yields glucose
(glucosan); inulin, yields fructose (fructosan)
CELLULOSE
Polysaccharide composed of glucose units
-1,4 linkages (forms primary cell walls in
plants)
Pectins are closely related to cellulose
Hemicelluloses (occurs with cellulose)
- high MW
- more soluble, more easily hydrolyzed
- closely related with gums and mucilages
PENTOSE
C5H10O5 (arabinose, xylose, ribose)
Products resulting from the hydrolysis of
pentosans
- Example of pentosans: Xylan (occurs in the
wood of deciduous trees)
Result from the hydrolysis of gums and
mucilages
MONOSACCHARIDES
Simple sugar
Ketonic/aldehydic substitution product of a
polyhydroxy alcohol
Simplest: diose (hydroxyacetaldehyde) HO-CH2CHO
- doesnt occur naturally
Aldehydic and ketonic triose (glyceraldehyde and
dihydroxyacetone)
- usually in the form of phosphate esters
Tetroses not found in the free state
Pentoses- common
-usually products of hydrolysis of hemicelluloses,
gums, and mucilages
Hexoses most important monosaccharides
found in plants
- first detectable sugars synthesized by plants
Out of 48 isomers, only 2 occur in the free state
in plants:
- D- fructose (levulose)
- D- glucose ( dextrose)

When hydrolyzed
- startch: glucose
- inulin: fructose
HEXOSES
6-membered, open chain compounds
GLUCOSE
Aldohexose
Polyhydroxy alcohol
FRUCTOSE
Ketohexose
Polyhydroxy alcohol
More complex and could exist in 2 cyclic forms
Fructopyranose: structure of the crystalline sugar
furanose structure (5-membered ring)- occur
when fructose is present in oligosaccharides and
polysaccharides

phosphate esters of certain heptoses are important

in the clucose metabolism of animals and in
photosynthesis

8-carbon sugar- isolated from crushed avocado

pulp
- name: D-glycero-D-manno-octulose
- also isolated from Sedum spp.
DISACCHARIDES
SUCROSE
AKA -D-glucopyranosyl--D-fructofuranoside
Occurs abundantly in the free state
Occurs in fruit juices, sugar cane, sugar beet, sap
of certain maples, etc.
Hydrolysis = invert sugar (contains equimolecular
quantities of glucose and fructose)
Non reducing sugar
MALTOSE
AKA 4-0--D-glucopyranosyl-D-glucopyranose
Seldomly occurring in the free state
Produces by the hydrolysis of starch during the
germination of barley and other grains (diastatic
fermentation)
Reducing sugar
Glucose + glucose

Glucose, fructose, sucrose, maltose most

commonly occurring in vegetable drugs

Limited in nature (free state or glycosidal

combination)
- monosaccharides:
- mannose (occurring in manosans
- galactose (constituent of lactose and raffinose)
- disaccharides:
- trehalose: in fungi (non reducing)
- lactose: milk sugar (contains aldehyde ;
reducing sugar)
BIOSYNTHESIS OF CARBOHYDRATES

PRODUCTION OF MONOSACCHARIDES BY
PHOTOSYNTHESIS
Products of photosynthesis
- 2 classes of reactions in photosynthesis:
o Light reactions (convert
electromagnetic energy -> chemical
potential
o Enzymatic reactions (use energy to fix
CO2 -> sugar) (aka dark reactions)
Summary of both:
PRODUCTION OF SUCROSE
Sucrose :considerable metabolic importance in
higher plants
- first sugar formed in photosynthesis
- main transport material
Newly formed sucrose: usual precursor for
polysaccharide synthesis
Alternative pathway: reaction between glucose 1phosphate and fructose
- responsible for sucrose production
- biosynthesis of this is important metabolite in
higher plants
Fructose 6-phosphate (from the photosynthetic
cycle) converted to glucose 1-phosphate (reacts
with UTP) to form UDP- glucose.
UDP- glucose reacts with:
- fructose 6-phosphate -> first sucrose phosphate
and ultimately sucrose, or
-fructose -> sucrose (directly)
SUGARS AND SUGAR CONTAINING DRUGS
1. SUCROSE
From Saccharum officinarum , Beta vulgaris, etc.
Aka saccharum/sugar
Obtained commercially from sugar cane and
sugar beets, sugar maple (Acer saccharum)
PRODUCTION:
- boiled with lime to neutralize the plant acids (if
not, sucrose will be changed into invert sugar)
and to coagulate albumins
Scum: latter that rises to the top (removed)
Juice is then filtered -> decolorized with sulfur
dioxide -> concentrated, and crystallized
Molasses: residual, dark colored syrup
In cases of sugar beets, they are dug, washed,
sliced into cossettes (small, limp slivers)
-extracted with hot water
-crude solution is then subjected to the
purification process
USES: pharmaceutic necessity, demulcent,
nutrient
(aq) bacteriostatic, preservative
masks disagreeable tastes, retards oxidation
2. DEXTROSE

aka -D(+)-glucopyranose or D-glucose

grapes
obtained by controlled enzymatic hydrolysis
suitable for parenteral use
use(s):
- nutrient ; ingredient in dextrose injection,
alcohol, dextrose injection, alcohol and dextrose
injection, dextrose and sodium chloride injection,
dextrose and sodium chloride tablets, dopamine
hydrochloride and dextrose injection, and
potassium chloride in dextrose injection; present
in anticoagulant citrate phosphate dextrose
solution
DEXTROSE EXCIPIENT
- crystalline dextrose monohydrate
- prepared by controlled enzymatic hydrolysis of
starch
- dextrates: purified mixture of saccharides (not
less than 93% dextrose)
- use(s): sweetening agents(substitute for sucrose)
; tablet binders and coating agents
-replaced liquid glucose
LIQUID GLUCOSE
- incomplete hydrolysis of starch
- dextrose (primarily) + dextrins + maltose +
water
- prepared by controlled acid hydrolysis of corn
starch
CALCIUM GLUCONATE
- calcium salt of gluconic acid
-soluble in cold water
- less irritating
- use(s): electrolyte replenisher, used to obtain the
therapeutic effects of calcium
-usual dose: 1g orally 3 or more times a day; IV
(1-3 times a day)
- gluconic acid is obtained by
o Oxidation of dextrose (with chlorine or
electrolytically in the presence of a
bromide
o Fermentation
CALCIUM GLUCEPTATE AND CALCIUM
LEVULINATE
- calcium salts of 7 and 5 carbon acids
- semisynthetic
- glucoheptonic acid :prepared from glucose via a
cyanohydrin intermediate
- levulinic acid: prepared from starch/ cane sugar
by boiling with HCl.
- salts are calcemic
- used parenterally to obtain therapeutic effects of
calcium
FERROUS GLUCONATE
- ferrous salt of gluconic acid
-hematinic and is employed in iron deficiency

3.
-

4.
-

anemia
-prophylactic dose: 325 mg/day
-therapeutic dose: 325 mg 4 times a day
- causes less gastric distress than inorganic
ferrous salts
-PROPRIETARY PRODUCTS: Fergon, ferralet,
and simron
FRUCTOSE
D-fructose, levulose, -D(-)-fructopyranose, D(-) fructofuranose, fruit sugar
Obtained by the inversion of aqueous solutions of
sucrose and the subsequent separation of fructose
from glucose
Sucrose (hydrolyzed)= fructose +dextrose
Ketone sugar
Occurs naturally in most sweet fruits and in
honey
Use(s): food for diabetic people (esp for diabetic
acidosis), infant feeding, ingredient in fructose
injection and fructose and sodium chloride
injection, nutrient, electrolyte replenishers)
- when given parenterally, it produces less urinary
secretions compared to glucose
Half as sweet as glucose
High fructose sweeteners :prepared by controlled
enzymatic isomerization of glucose
Glucose isomerase from Streptomyces spp
High fructose corn syrups 90% fructose
LACTOSE
Cows milk
Bos Taurus (bovidae)
Spgr 1.029 1.034
Contains from 80-90% water (3% casein, 5%
lactose, 0.1 to 1% mineral salts)
2.5 to 5% of fat (butter)
When churned -> butter
- liquid that is left (buttermilk)
Skimmed milk : milk left after separation of the
cream
- if treated with rennin, it forms a coagulum (with
proper treatment it is made into cheese)
Whey: liquid separated from the coagulum
Condensed milk: partial evaporation of milk in a
vacuum and consequent sterilization in
hermetically sealed containers by autoclaving
Malted milk: evaporating milk with an extract of
malt.
Low heat and vacuum prevent the destruction of
enzymes
Use: nutrient, source of lactose, yogurt, and
kumyss
Casein and sodium caseinate employed in
culture media

5.
-

LACTOSE OR MILK SUGAR

-crystallized from whey
- redissolved in water, decolorized with charcoal
and recrystallized
- readily absorbs odors
-upon hydrolysis, yields D- glucose +D-galactose
- reduces Fehlings solution, undergoes
mutarotation, and forms an osazone
- lactose is hydrolyzed by lactase
- easily undergoes lactic and butyric acid
fermentations
-use(s): tablet diluent; less sweet; nutrient in
infants food; minor role in establishing the
intestinal microflora; inert diluent
- more easily hydrolyzed
LACTULOSE
- semisynthetic sugar
- prepared by alkaline rearrangement of lactose
- fru + gal
- poorly absorbed
- most orally ingested lactulose reaches the colon
unchanged.
- bacteria in the colon metabolize the disaccharide
to acetic and lactic acids (accumulation causes
laxative effects)
- daily dose: 10-20 g of lactulose (for chronic
constipation)
-most significant therapeutic use: decrease the
blood ammonia concentration in portal-systemic
encephalopathy
-usual dosage: 20-30g of lactulose as a syrup 3/4x
a day
XYLOSE
Aka D-xylose, or wood sugar
Pentose
Obtained by boiling corn cobs, straw or similar
materials with dilute acid to hydrolyze the xylan
polymer
Normally absorbed from the small intestine
The relative excretion of xylose in the urine is
indicative of intestinal malabsorption states that
may accompany such conditions as celiac disease,
sprue, crohns disease (regional ileitis), pellagra,
radiation enteritis, and surgical resection
Prescription product: xylo-pfan

2.
-

DRUGS CONTAINING COMPOUNDS

METABOLICALLY RELATED TO SUGARS
PRODUCTS OF GLYCOLYTIC AND OXIDATIVE
METABOLISM
(at the back)
1. CHERRY JUICE
Aka Succus cerasi
From Prunus cerasus (rosaceae)

Preserved with 0.1% benzoic acid, allowed to

stand at RT until the addition of half its volume of
alcohol to a small portion of the juice (produces a
clear solution)
- this test indicates that the pectin in the juice has
been destroyed
- contains not less than 1% malic acid
- cherry syrup: flavored vehicle (for acidulous
mixture)
ACIDS
Usually acidulants/ components in buffer systems
to control acidity
Organic acids cause less irritation
Nontoxic
CITRIC ACID
- from lemon juice
- commercially from lemons, limes, or pineapples
but mostly by fermentation of sucrose
- readily soluble in water and alcohol
- use: useful in buffering systems, acidulant in
effervescent formulations, ingredient in
potassium citrate and citric acid solution and
sodium citrate and citric acid solution, systemic
alkalinizers, and in anti coagulant citrate dextrose
silution and anti coagulant citrate phosphate
dextrose solution
LACTIC ACID
- miscible with water, alcohol, and ether
- consists of lactic acid and lactic acid lactate
equivalent to a total of not less than 85% and not
more than 90% by weight of lactic acid
- obtained by lactic fermentation of sugars/
synthetically
- use(s): acidulant (esp in infant feeding formulas)
- sodium lactate injection electrolyte
replenisher; treatment of metabolic acidosis
- calcium lactate- calcium replenisher
-usual oral dose: 1-5g (3x a day)
TARTARIC ACID
- dicarboxylic acid
obtained as a by product of the wine industry
- soluble in water
- freely soluble in alcohol
- use: substiture for citric acid in buffer systems
and in effervescent formulations
FERROUS FUMARATE
- hematinic agent
- usual therapeutic dose: 200 mg (3/4x a day)
- PROPRIETY PRODUCTS: feco-T, feostat,
fumasorb, fumerin, hemocyte, ircon, palmiron
ALCOHOL (or ethanol)
- containing not less than 92.3% by weight,
corresponding to 94.9% by volume, of ethanol @
15.56 C
- 70% w/v soln = anti infective

-alcohol (5%/10%) and dextrose (5%) injection =

increase caloric intake and replenish fluids
DILUTED ALCOHOL
- alcohol + water (ethanol percentage: 48.4-49.5)
- solvent
- by distillation, brandy (from wine), whiskey
(from fermented malted grain), and rum (from
fermented molasses) are produced on a
commercial basis
- each usually contains 40 55% of alcohol
- wine uses: mild stimulant and tonic
- brandy and whiskey are classed as central
nervous system depressants

PRODUCTS OF REDUCTIVE METABOLISM

Sugar alcohol (glycitol) phosphates may be
formed by reduction of ketose phosphates in
reactions utilizing NAD/ NADP as the hydrogen
carrier
Examples of reactions catalyzed by enzymes:
- mannitol phosphate dehydrogenase
- mannitol 1-phosphatase
-

In certain fungi, mannitol is formed directly from

D- fructose by mannitol dehydrogenase:

1.
-

MANNITOL
Aka. D-mannitol
Hexahydric alcohol
Obtained by reduction of mannose or by isolation
from manna.
- manna: dried saccharine exudate from Fraxinus
ornus (oleaceae)
- contains 50-60% mannitol
- used for laxative properties
Freely soluble in water and boiling alcohol but
almost insoluble in cold alcohol
Not absorbed in the GIT
Parenterally it is not absorbed but eliminated by
glomerular filtration
Use: diagnostic aid, osmotic diuretic
Usual diagnostic dose: 200 mg/kg of BW in 125% solution administered IV in 3-5 min
Usual diuretic dose: 50 to 100 g daily in a 5 to
25% sol by IV infusion at 30-50mL per hour rate
Mannitol injection or mannitol and sodium
chloride inj diuretic purposes
Prescription product: osmitrol
SORBITOL
Aka D-glucitol, D-sorbitol
Hexitol (hexahydric sugar alcohol)
From ripe berries (Sorbus aucuparia (rosaceae))

2.
-

Prepared from glucose by hydrogenation or by

electrolytic reduction
Readily soluble and compatible with syrup,
alcohol and other polyols
Half as sweet as sucrose
Has humectant properties

Must be use in cinjunction with saccharin/ non

caloric sweetener cause it acts as an osmotic
laxative
Also used for urologic irrigation
3. STARCH
CORN, WHEAT, AND POTATO STARCHES
INULIN
DEXTRAN
CELLULOSE

CELLULOSE DERIVATIVES
GUMS AND MUCILAGES
TRAGACANTH
Dried gummy exudate
Astragalus gummifer (leguminosae)
Aka. Gum tragacanth
ACACIA
KARAYA GUM

SODIUM ALGINATE
AGAR
PLANTAGO SEED
GUAR GUM
LOCUST BEAN GUM
XANTHAN GUM
PECTIN