CARBOHYDRATES •most important monosaccharide in plants: hexoses

Classification based on the functional groups

•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 1. aldose - aldehyde
named as CARBO + HYDRATES; hydrates of carbon 2. ketose – ketone
•first products of photosynthesis Hexoses- most Important monosaccharides
•polyhydroxy alcohols (either aldehyde or ketone)
Glucose
•general formula:
Classified into: •aldohexose
•aldehyde group is present in C1
A. Sugars
•reducing sugar as determined by BENEDICT'S TEST
1) Monosaccharides •occurs as: linear and cyclic
2) Disaccharides Glucose
3) Polysaccharides
•Linear configuration: Fischer Projection
•Homglycans
–-L-glucose- less active
–a. Starch- Glucosan- yields glucose units –-D-glucose-more active
–b. Inulin- Fructosan- yields fructose units •Cyclic configuration: Haworth Projection
–c. Cellulose- Glucosan- yields glucose units – looks like a pyran; glucopyranose
•Heteroglycans glucose / dextrose (D-glucose / -D-glucopyranose)
•“blood sugar, physiologic sugar, grape sugar, corn sugar”
–a. Gums and Mucilages
•natural source: grapes
–b. Glycosides
•Plants : sugar is transported in form of sucrose
CARBOHYDRATES and RELATED COMPOUNDS
use: nutrient (dextrose: given, PO, SC, IV or enema) , mask
MONOSACCHARIDES unpleasant taste, flavor
Uses of Glucose
•simple sugars; have 1 sugar unit; cannot be further hydrolyzed
• crystalline, water-soluble and sweet –Parenteral- rigorously purified
 •-D5W, D5NSS, D5LR- nutrient Reducing sugars:
–Pharmaceutic necessity- less rigorous purification
Barfoed ( CuSO4 + HAc)
•Liquid Glucose- syrupy liquid, almost colorless and taste sweet;
sweetening agent Benedict’s rgt ( CuSO4 + Na2CO3)
•Dextrose excipient- crystalline sweetening agent
Pentoses
Related compounds:
Xylose
a. liquid glucose - thick, syrupy liquid from incomplete hydrolysis of
starch •wood sugar
b. calcium gluconate - electrolyte replenisher •obtained from boiling corn cobs, straw, heart of deciduous trees
c. calcium gluceptate - calcium source and similar mateials with dilute acids to hydrolyze the xylan polymer
d. Ferrous gluconate - hematinic, given for iron deficiency anemia •diagnostic aid in intestinal malabsorption
Fructose DISACCHARIDES

•a ketohexose Composed of 2 monosaccharide units

•ketone group is present in C2 Sucrose, Maltose, Lactose
•Reducing sugar •formed via dehydration synthesis
•Fruit sugar; sweet fruits and honey
1. sucrose / table sugar / saccharum
•also known as Levulose, the sweetest monosaccharide
Uses of Fructose -glucose + fructose; α-1,2 glycosidic bond
- non reducing sugar
Food for diabetic patients
molasses: residual, dark colored syrup after crystallization process
ingredient in infant feeding formula
• pharmaceutic necessity for syrups; demulcent; nutrient;
ingredient in Fructose injection, nutrient
preservative
fructose / levulose / fruit sugar
•_______- bitter taste of beer
–sweetest monosaccharide
invert sugar: equimolar amounts of glucose and fructose; darken
natural source: fruits and honey; hydrolysis of inulin
due to fructose
use: food for diabetic people (cannot increase blood glucose level)
•-obtained from
 –Sugar cane Saccharum officinarum, Poaceae - use: tablet diluent
–Sugar beets Beta vulgaris, Chenopodiaceae - lactose intolerance: absence of enzyme lactase/ -galactosidase
–Sugar maple Acer saccharum, Aceraceae (diarrhea, GI disturbance)
•composed of Fructose and Glucose lactulose
•Non-reducing sugar
•synthetic sugar from the tautomerization (alkaline rearrangement
Uses of Sucrose
of a ketone to an enol) of lactose
•demulcent uses: 1) laxative (Duphalac®)
•sweetening agent •poorly absorbed; bacteria (colon) converts it to acetic acid & lactic
•coating agent acid
•preservative • both acids are GI irritants, ↑ peristalsis
•production of syrups decreases blood ammonia concentration in portal-systemic
•retards oxidation encephalopathy
2. trehalose acidified stools trap ammonia as NH4+
so, ↓ reabsorption, ↓B ammonia
found in brown seaweed, widely distributed in fungi
KUMYSS- alcoholic beverage made from fermented mare's milk; made
• glucose + glucose; α-1,1 glycosidic bond
originally by nomads of central Asia
3. maltose / malt sugar / beer sugar
OLIGOSACCHARIDES - have 3-10 sugar units
•produced in large quantities by the hydrolysis of starch during
germination of barley 1. maltotriose
• use: component in beers
2. dextrins
•glucose + glucose; α-1,4 glycosidic bond
4. lactose / milk sugar “limiting dextrins”: products of partial hydrolysis of starch
(amylase, glucosidase)
•from animal source: from fresh cow’s milk (Bos taurus)
–Browning of bread
•from the crystallization of whey, a by-product of cheese
α-glucosidase inhibitors:
production
•glucose + galactose; -1,4 glycosidic bond
 - inhibit post-prandial (after eating) increase in glucose levels (anti- –isolated from lemon juice by Scheele in 1784
DM) – use: acidulant in effervescent preparations; buffer system
ex . Acarbose, Miglitol; • lactic acid
AE: flatulence, hepatotoxicity
–acidulant in infant feeding formula
3. gentianose - glucose + glucose + fructose
•tartaric acid
4. raffinose - glucose + galactose + fructose
–obtained as a by-product of the wine industry
5. stachyose - glucose + galactose + galactose + fructose
–use: substitute for citric acid in buffers
Products of Oxidative Metabolism • Formic acid

Cherry Juice, Plant Acids, Alcohol –Found in ants, volatile poison

Cherry Juice or Succus cerasi •Acetic acid

•ripe fruit of Prunus cerasus, Rosaceae –Precursor of fatty acids/lipids; vinegar

•contains pectin, the main cause of incompatibilities especially
•Oxalic acid
when added to preparations containing alcohol
•remedy: add 0.1% benzoic acid and leave for 1 week –Very insoluble, as calcium salts
•constituent: malic acid –Balimbing (Averrhoa carambola); kamias (A. bilimbi
•use: preparation of cherry syrup- used to mask the taste of sour •Tartaric acid
drugs
–By product of wine production
Other Related Compounds
–Tamarind
•Plant acids - aliphatic organic acids with not more than 6 Carbons and 2 or –use: substitute for citric acid in buffers
3 carboxyl groups –Aconitic acid
–acidulants in effervescent formulations –Dehydrated form of citric acid
–component of buffer systems •Shikimic acid
• citric acid
–Precursor of aromatic compounds
 –Amino acids Sorbitol
•Ascorbic acid
•from the berries of mountain ash, Sorbus aucuparia, Rosaceae
–Vit. C, water soluble •aka D-glucitol
•taste half as sweet as sucrose
•Citric acid
•not absorbed on oral ingestion that is why it is used in the
–isolated from lemon juice by Scheele manufacture of toothpastes and chewing gums
– use: acidulant in effervescent preparations; buffer system POLYSACCHARIDES
Alcohol or Ethanol
•more than 10 sugar units
• 94.9% ethanol by volume @ 15.56*C •for storage (starch in plants, glycogen in animals), and for structure
•product of fermentation (chitin, cellulose)
•undergo the process of distillation to concentrate the alcohol •homoglycans / homopolysaccharides (made up of one type of
content to 40-55% sugar only)
–Brandy- Wine a. starch (glucosan)
–Whiskey- Malted Grain
•uses: dusting powder, tablet filler, binder, disintegrant, antidote to
–Rum- molasses
I2 poisoning
Uses of Alcohol
•temporary storage form of photosynthetic products in plants
•In low concentration, CNS stimulant •natural sources: Corn grain (Zea mays)
•In higher concentration, CNS depressant • Potato tubers (Solanum tuberosum)
***Diluted alcohol: 48.4-49.5% ethanol @ 15.56*C • Wheat grain (Triticum aestivum)
Products of Reductive Metabolism •mixture of 2 structurally different polysaccharides:
Enzymes that breaks down starches:
Mannitol, Sorbitol
Amylases:
Mannitol
1. α-amylases
•from manna, Fraxinus ornus Oleaceae
•osmotic diuretic and osmotic laxative - enzyme in pancreatic juice (amylopsin) & saliva (ptyalin)
 - random splitting of α-1,4 links
•end-product: mixture of glucose, maltose, amylopectin
2. -amylases
- capable of splitting only α-1,4 bonds
- end-product is nearly pure maltose
•remove maltose unit from non-reducing end of polysaccharides
•at branching points: maltose & dextrins (incomplete hydrolysis)
Starch preparations:
1. pregelatinized starch - starch processed to rupture all or part of
granules in the presence of water; used as tablet excipient
2. sodium starch glycolate - used as tablet disintegrant
3. hetastarch - semisynthetic material used as plasma expander
(6%); 90% amylopectin
b. glycogen / animal starch (glucosan)
- frequency of branching: every 10 units
- more highly branched compared to starch; in animals
iodine test: wine red
c. inulin / hydrous inulin
- polymer of fructose ( -2,1 bonds); “fructosan”
- uses: to measure renal glomerular filtration
d. Dextran
•glucosan
•Leuconostoc mesenteroides release the enzyme dextran sucrase
which is responsible for the conversion of sucrose to dextrans
•plasma expander because it has the same osmolarity and viscosity
as with plasma
e. cellulose (glucosan)
- polymer of glucose with -1,4 bonds
- not digested by mammalian enzyme systems, due to their lack of
cellulase
- bacteria, rumen microflora or herbivorous animals have cellulase
- natural source: Purified/ Absorbent cotton- from the hair of the
seeds of Gossypium hirsutum, Malvaceae
• component of cell wall (responsible for its rigidity)
• most abundant organic compd on earth
•Cellulose: plant :: chitin: fungi
–use: mechanical protection against bacteria
–absorb mucus, pus and blood
Cellulose derivatives:
•methylcellulose - bulk laxative and suspending agent
•ethylcellulose - tablet binder and film coat
•cellulose acetate phthalate - enteric coating for tablets
•pyroxylin / soluble guncotton
–use: topical protectants
–action of nitric & sulfuric acid on cotton
• pyroxylin + alcohol + ether (1:3) = collodion
– collodion + camphor (2%) + castor oil (3%) = flexible
collodion
–use: topical protectants
 • chitin - homopolymer of N-acetyl- -D-glucosamine
Heteroglycans- polysaccharides that yield more than one types of
monosaccharide units upon hydrolysis
Gums and Mucilages
components: Bassorin (60-70%): swelling property
Tragacanthin (30-40%): water-soluble
use: suspending agent, emulsifying agent (6%)
NOTE: more resistant to acid hydrolysis, so it works in ↓ pH
b. acacia / Gum arabic

•Natural plant hydrocolloids that may be classified as anionic or - exudate from Acacia senegal
non-ionic polysaccharides - arabin: complex mixture of Ca, Mg, and K salts of Arabic
•Produced by plants as a protective after injury acid
•Upon hydrolysis, they yield arabinose, galactose, glucose, use: suspending agent (35%)
mannose, xylose and other uronic acid derivatives c. Ghatti gum / Indian gum
•Plant Exudates
- exudate form Anogeissus latifolia
•Marine Gums
use: substitute for acacia (forms more viscous dispersions)
•Seed Gums
d. Karaya gum / Sterculia gum
•Microbial Gums
•Pectin -exudate from Sterculia urens
- forms a discontinuous type of mucilage
•Different types of sugar
-use: bulk laxative, emulsifying agent,
a. gums - natural plant hydrocolloids - dental adhesive
•TAGhKa
1. Shrub and Tree exudates
2. Marine gums
a. tragacanth / Gum tragacanth
a. sodium alginate / algin
- exudate from Astragalus gummifer
-from brown seaweeds (Macrocystis porifera)
3 forms:
- components: salts of Alginic acid, mannuronic acid
1. vermiform – wormlike ,twisted in coils
- use: suspending agent, food industry (ice cream,
2. tragacanth sorts - tearlike
chocolate)
3. ribbon / flake gum -has longitudinal striations
 b. agar / Japanese isinglas/ gulaman b. Guar gum / guaran

- substance from Geladium cartilagineum or Gracilaria - Cyamopsis tetragonolobus

confervoides -plant part used:
- use: stiffening agent in preparation of culture media; powdered endosperm
thickening agent -Bulk forming laxative
-components: Agarose - has low sulfate content c. Locust Bean gum / St. John’s Bread / Carob pulp
Agaropectin
• Ceratonia siliqua
c. carrageenan / Irish moss / chondrus
•part used: powder made from flesh of mature seed pods
- hydrocolloids from red algae or seaweeds (“flour”)
- Chondrus crispus, Gigartina mamillosa •use: chocolate substitute;
- 3 Forms: -carrageenan and -carrageenan – with gelling •used as thickener and stabilizer
property 4. Microbial gums
- carrageenan – non gelling property; use: thickener
a. Xanthan gum
d. Danish agar / furcellaran
–high MW gum prepared by
-from red algae Furcellaria fastigiata
– the action of Xanthamonas campestris
-- similar property to -carrageenan (gelating and
– possesses pseudoplastic properties:
suspending agent)
– used in toothpastes and ointments
-SoAg CaDa
b. Dextran
3. Seed gums (bulk-forming laxatives)
– polyglucan formed from sucrose by the action of a
a. Plantago Seed / psyllium seed / plantain seed
transglucosylase enzyme system
•-Plantago psyllium, P. indica: Spanish or French psyllium –present in Leuconostoc mesenteroides
seed – use: plasma expander
• Plantago ovata: Blonde psyllium or Indian plantago seed
•plant part used: powdered seed coat
 •Leuconostoc mesenteroides release the enzyme dextran
sucrase which is responsible for the conversion of sucrose
to dextrans
•plasma expander because it has the same osmolarity and
viscosity as with plasma
Plant Extracts

• 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