Professional Documents
Culture Documents
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:
• 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)
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
Reducing sugars:
Barfoed (CuSO4 + HAc)
or C4H6CuO4 = Cu2O
+
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
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
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)
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
(CHOH)n
CH2OH
CHO
(CHOH)n
CH2OH
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.
Acetic acid
Precursor of fatty acids/lipids; vinegar
Plant Acids: 4. Succinic Acid
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
-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
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
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
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
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
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