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Phle Reviewer Module 2 Pharmacognosy
Phle Reviewer Module 2 Pharmacognosy
PHARMACOGNOSY
BIOCHEMISTRY
PHARMACOGNOSY
I. INTRODUCTION Indigenous plant grows in their native countries
PHARMACOGNOSY is applied science that deals w/ the biological, Naturalized grew in foreign land other than their native countries
biochemical & economic features of drugs of Natural Substances found in nature that comprise whole plants & herbs
biologic origin & their constituents. Derivatives/ Extractives refers to single substance/s which are considered
the discipline of medicinal chemistry as chief constituents of the drugs
study of drugs of biologic origin CRUDE DRUGS vegetable or animal drugs that consist of natural substances
Focuses: 1. Identification of plants and animals that have undergone only the presence of COLLECTION &
DRYING.
2. Chemistry
DRUG CONSTITUENTS
3. Evaluation, preservation & use or
application of crude drugs Natural directly obtained from nature
4. Toxicology Ex: Camphor from Camphor Plants
5. History, distribution, collection and Semi-synthetic from chemical modification of a natural constituent
selection Ex: Camphor pinene pine trees
6. Preparation and commerce Totally Synthetic manufactures from chemical synthesis
Three disciplines (Basic) devoted to drugs Ex: Camphor from Cyclopentacliene
1. Pharmacology which dealt w/ drug actions & effects
2. Pharmacognosy covering all information on medicines PREPARATION OF CRUDE DRUGS
from natural sources plants, animals, Collection select the species to cultivate
& microorganism
Harvesting gathering the samples at a specific & proper period or
3. Medicinal Chemistry the science of synthetic drugs
season
Constituents:
manual labor or mechanical devices
1. Active Constituents compounds that are responsible for
Drying removal of moisture
the therapeutic effect.
-bacterial & fungal growth
2. Inert Constituent are differentiated to active
-hydrolysis
constituents
facilitates milling & grinding
have no pharmacologic activity
Examples: Cellulose, Starch, Lignin, remove bulk convert the drug to a form that is
Albumin, Suberin, more convenient for handling.
Coloring matter fixes the constituent
Secondary Constituents ensure good keeping qualities
are influenced by three principal factors Curing special drying process
1. Heredity (genetic composition) drying + curing agent
2. Ontogeny (Stage of Development) enhance the properties of the active ingredient
3. Environmental Factors can produce variations ex: Cascara sagrada
in secondary plant
reduced glycosides MgO x 1 yr oxidized glycoside
constituents include soil,
(irritating) (less irritating)
climate, associated flora,
& methods of cultivation Garbling final step in the preparation of crude drugs
Drug Biosynthesis/ Biogenesis study of the biochemical physical process of removing extraneous material
pathways leading to the Packaging, storage, preservation
formation of secondary for protection & marketability
constituents used as drugs. Preservation of Crude Drugs:
Exposure of the drug to 65C Temperature simplest form in preventing
BRIEF HISTORY insect attacks & other form of destruction
Papyrus Ebers Egyptian document Methyl Bromide is used in the fumigation of large lots of crude drugs
Details the use of plant & animals in medicine Chloroform (Carbon Tetrachloride) used to control Insect Attack by
By George Ebers adding few drops to the container
Dioscorides Greek Physician Methods of Evaluation of Crude Drugs
De Materia Medica Organoleptic or morphological (leaves, barks, roots, stem)
description of ~600 medicinal plants
color, odor, taste, size, shape, & special features,
Claudius Galen Greek pharmacist-physician
“Galenical Pharmacy” like touch, texture
method of processes of preparing Microscopic detects cellular tissues, trichomes, stomata, starch
formulas containing animal & plant drugs granules, calcium oxalate crystals aleurone grains
C.A. Sydler Coined the term Pharmacognosy Chemical isolation, purification, identification
pharmakon “drug”
Physical moisture contents, specific gravity, optical rotation,
gnosis “knowledge”
refractive, melting point, viscosity, & solubility
J.A. Schmidth First one to use the term Pharmacognosy in
literature Biological antifertility activity, anti ulcers activity, etc.
Joseph French Pharmacist
Caventou Quinine w/ the collaboration of Pelletiere CLASSIFICATION OF DRUGS
Pierre Phytochemist Morphologic Based on the part used
Robiquet Codein Classification Ex: Root crop, seed gums, etc
Narcotine
Taxonomic Based on the natural relationship or
Rudolf Brandes German Pharmacist
Hyoscyamine
Classification phylogeny
Philip Geiger Atropine w/ the collaboration of Rudolf Brandes Ex: Plant Families: Rutaceae
Theophrastus Father of Botany Pharmacologic Based on therapeutic activity
Classification Ex: Hallucinogens, Anticholinergic
Chemical Based on the chemical class of the
Classification constituents
II. CARBOHYDRATES & RELATED COMPOUNDS A. Monosaccharides simplest CHO units
Carbohydrates most abundant group of organic molecules in cannot by hydrolyzed into simpler sugar
nature undergoes mutarotation
is the first product formed during Photosynthesis 1. Diose (2C) Hydroxyacetaldehyde
2. Triose (3C)
First product of synthesis is Glucose Aldotriose: Glyceraldehydes
Ketotriose: Dihydroxyacetone
Polyhydric aldehydes & Ketones 3. Tetrose (4C) – Erythrose
Aldehyde: RCOH 4. Pentose (5C)
Ketones: RCOR ▪Ribose aldopentose
product of gum hydrolysis
Contain C, H, O in the Empiric Formula
found in RNA (Ribonucleic Acid)
▪Ribulose Ketopentose
Functions: -Source of Energy (Glucose
▪Xylose Aldopentose
-Storage of Energy
“wood sugar”
Plants: STARCH
from woody part of plant
Animals: GLYCOGEN
not found free –Xylan Polymer
-Cell components: Glycoproteins
-Structural Component: Cellulose, Chitin diagnostic aid for intestinal absorption
absorbed by not metabolized
Classes: Sugar: Monosaccharides ▪Xylulose – Ketopentose
Disaccharides
Polysaccharides Test for Pentoses:
-Bials Test
Anthrone Test general test for Carbohydrate -Benzidine Test
which yields a blue or green solution 5. Hexose (6C) most important monosaccharides
▪Glucose – aka Dextrose
Energy: 1 gram of Carbohydrate = 4 kcal of Energy Aldohexose
aka “grape sugar”
“physiologic sugar”
“blood sugar”
“corn sugar”
-D-glucose most abundant in nature
primary product of photosynthesis
controlled enzymatic hydrolysis of starch
nutrient
Normal value in the blood: 80-120mg%
Preparation (Forms) –Glucose
Dextrose excipient crystalline dextrose
monohydrate
less rigrous purification
pharmaceutic necessity
Liquid glucose product of incomplete (acid)
hydrolysis of starch
Dextrates mixture of saccharides 93% dextrose
pharmaceutic necessity
▪Fructose aka Levulose
Ketohexose –Seliwanoff Test
“Fruit Sugar” (from Honey); “Sweetest Sugar”
sweetest sugar but bitter after taste
from the inversion of aqueous solutions of
Sucrose Glucose + Fructose
from hydrolysis of inulin (fructose polymer)
nutrient
high fructose sweetener
=from glucose glucose isomerase fructose
Streptomyces spp.
▪Galactose aldohexose
“Brain Sugar”
most rapidly absorbed from the small intestines
C4 epimers w/ glucose
found in milk (lactose = glucose + galactose)
Nerve Fibers compose of Galactose
6. Heptose (7C) – Sedoheptulose
7. Nonose (8C) – Sialic Acid (or neuraminic acid)
B. Disaccharides two monosaccharide units linked by glycosidic bond C. Oligosaccharides 3-10 monosaccharide units
1. Sucrose “Table Sugar”; “Invert Sugar” 1. Maltose 3 glucose units (-1,4)
glucose + fructose ( 1,2) intermediate product of acid hydrolysis
non-reducing sugar (no free carbonyl)
is the only disaccharide that occurs in free state 2. Dextrin several glucose units
almost disaccharides are bound responsible for the browning of bread
Sources: -Sugar Beets (Beta vulgaris) product of partial hydrolysis o starch
cut into limpsilver = Cosettes
-Sugar Cane (Saccharum officinarum)
-Sugar Mapple (Acer saccharum)
Preparation: 1. Sugar Cane Juice is boiled w/ Lime
Lime basic compound
neutralize plant acids
coagulate albumins
Uses: ▪Pharmaceutic Necessity
Syrup, NF mask disagreeable taste of drugs
85% sucrose
sufficient bacteriostatic
sel-preserving
▪Demulcent
▪Nutrient
Saccharose is almost universally distributes sugar in
green leaves & in stems
Invert Sugar is darker & sweeter than sucrose
2. Maltose Malt Sugar
Glucose + Glucose ( -1,4)
reducing sugar
major degradation product of starch hydrolysis
3. Lactose Milk Sugar
Glucose + Galactose ( -1,4)
reducing sugar
found in cow’s milk (Bos Taurus)
Uses: ▪Tablet diluent
▪Infant feeding (nutrient)
establishes normal gul flora
(Lactobacillus spp.)
4. Milk Products
Whole Milk
-churned
Butter
Buttermilk
Separation
Cream
Skimmed Milk
Rennin
Whey
Coagulum treated Cheese
▪Condensed Milk partial evaporation in vacuum &
consequent sterilization
sterilized, sealed in hermetic
container by autoclaving
▪Malted Milk evaporated w/ Malted Extract
▪Kumyss fermented Milk
▪Whey the liquid separated from coagulum
liquid left after skimmed milk is treated w/
rennin
▪Rancid Flavor of Butter left at room temperature
is due to Butyric Acid
5. Lactulose (Duphalac®, Lilac®)
semisynthetic sugar, from the alkaline rearrangement of
lactose
Fructose + Galactose (-1,4)
laxative, to reduce straining in defecation
MOA: SI: Not absorbed.
LI: Lactulose is fermented by bacteria to lactic acid
& acetic acid
laxative action
D. Polysaccharides “glycans”
complex, high MW polymer of monosaccharides
1) Homoglycans only 1 type of monosaccharide
1. Cellulose structural polysaccharides in plant; -1,4
dietary fiber
makes up the cell wall of plants
Forms: Purified Cotton (Gossypium hirsutum)
Powdered Cellulose
Microcrystalline Cellulose Forms of starch:
Purified Rayon ▪Starch paste – dispersing starch in
Cellulose Derivatives: cold water
-Methylcellulsoe
-Ethylcellulose boiled granules swell & rupture
-Hydroxypropylmethyl cellulose resulting to
-Pyroxylin: Soluble guncotton/ translucent
Cellulose Trinitrate mixtures solution
to make collodions ▪Pregelatinized Starch –all the granules have been
ruptured in the presence of
obtained by the action of
water
nitric & sulfuric acid in
serve as plasma expander in
cotton
Collodion = Pyroxylin + Ether/ Alcohol
6% concentration
Flexible Collodion = Collodion + ▪Hetastarin –water-soluble form;
3% Castor oil+ >90% amylopectin;
Camphor plasma expander
-Cellulose acetate phthalate
-Caboxymethylcellulose
2. Chitin structural polysaccharides in animals & fungi
homopolyglycan of N-acetylglucosamine
Galacturonic Acid present in Chitin that cannot be ▪Sodium Starch Glycolate – a semisynthetic sodium
found in cellulose salt of carboxymethyl
3. Starch Storage of Polysaccharide In plants ether of starch
reserve carbohydrate of plants – disintegrating agent in
components: tablet formation
Amylose Amylopectin ▪Glutens – tacky proteins removed from corn & wheat
-amylose -amylose in the preparation of starch
Linearity Linear Branched 4. Glycogen – storage polysaccharides in animals
- 1,4 (every 25-30 units) more branched than starch
- 1,4 & -1,6 (branches every 10 units)
Solubility Less soluble More soluble in stored in the liver & skeletal muscles
in H2O in water water similar structure w/ Amylopectin
Size 250-300 >1000 units 5. Inulin Polyfructan
units abundant in the substance
Iodine Dark-blue Blue-violet members of family Asteraceae
Iodine Test confirmatory test for starch Improve digestion
consists of a greater proportion of amylopectin than used in culture media as a fermentative identifying
amylase agent for certain bacteria & in spinal laboratory
Amylose hydrolysis product of starch methods for the evaluation of renal function
responsible for forming a Diagnostic aid to estimate GFR
dark complex w/ Iodine (Glomerular filtration rate)
*-amylaseenzyme in pancreatic juice & saliva -filtration
*-amylaseremoves maltose units from the -reabsorption
non-reducing ends of -secretion
polysaccharide molecules 6. Dextran – homopolyglycan -1,6
usually isolated from: Rhizome from sucrose by the action of transglycolase
Fruit enzyme system in Leuconostoc mesenteroides
Seed plasma expander
Official Sources of Starch: iron dextran – hematin IV/IM
▪Corn ( Zea mays) 2) Heteroglycan more than one type of polysaccharides
▪Potato (Solanum tuberosum) Ex: D-gluco – D-mannan
▪Rice (Oryza sativa)
▪Wheat ( Triticum aestivum)
Unofficial Sources of Starch:
▪Arrow root ( Maranta Arundinacea)
Uses of Starch:
Dusting powder
Tablet-diluent,binding,(starch paste)
Tablet disintegrant
Antidote for iodine toxicity
E. Metabolically-related Drugs
1. Acids
Cherry juice – Prunus cerasus
Malic Juice
to make cherry syrup
Citric acid – tricarboxylic acid
COOH
HO COOH
COOH
lemon juice; -first isolated by Scheele
buffer, acidulants in effervescent formulations
salt = Systemic Alkalinizer – Potassium Citrate
(Acalka®)
Anticoagulant – Citrated Tubes
Lactic Acid Alpha Hydroxy Propionic Acid
– lactic fermentation of sugars
acidulant in infant feeding formulation
substance accumulates in the muscle as a
result of vigorous exercise
Tartaric Acid – dicarboxylic acid
by product of the wine industry
buffer,acidulant in effervescent formulation
Denige’s Test – used to differentiate
citric & tartaric acids
(citrates & tartrates)
Sugar Acids produce from the oxidation of Disaccahrides &
Monosaccharides (except sucrose)
Aldonic Acid produce from the oxidation of sugar’s
aldehyde group (group 1)
Oxalic Acid an organic acid found in fruits of
Averboa balimbi
is used as Bleaching Agent
Acetic Acid laxative action; used as Food Preservative
Concentrated Acid change monosaccharide to Furfural
2. Alcohols
Ethanol >92.3% by weight,
94.9% volume of ethyl alcohol at 15.56C
from fermentation & distillation
70% = localanti-infectives
Diluted alcohol – 48.4 to 49.5 % ethanol at 15.56C
Distilled Spirits: (produced by Distillation)
Brandy – distilled fromWine
Whiskey – distilled from Malted Grain
Rum – distilled from Molasses
J. Phenol Glycosides
1. Uva ursi Bearberry ( Archtostaphylo uva ursi)
Arbutin
available in the form of herbal teas
diuretic, astringent
2. Poison- Ivy & Oak Rhus spp.
Urushiol a non-volatile principle producing
allergic symptoms
– cause delayed contact dermatitis
D. Aldehyde
1. Cinnamon Oil Ceylon: Cinnamon zeylanicum
Saigon: Cinnamon laureirii
Cassia: Cinnamon cassia cassia oil
Cinnamaldehyde
flavorant, carminative, antiseptic
2. Lemon Peel Oil Citrus limon
citral limonene
3:1 = geraniol; neral
most important contributor to lemon oil flavor
Types: Terebintherate = terpenes = risk for resinification
Terpeneless = terpenes = risk fro resinification
Higher quality
,ore expensive
3. Sweet Orange Oil sweet aurantium, Citrus sinensis
decanal, limonene
4. Citronella Oil Cymbopogon citrates; C. nardus; C. winterianus
citronella insect repellant
5. Hamamelis Oil Hamamelis Virginia
2-hexanal/Acetaldehyde/ alpha-ionone/Beta-terpinol
for hemorrhoidal preparations
H. Ester
1. Gaultheria Oil, Sweet –birch Oil
Gaultheria Oil Oil of Wintergreen
Gaultheria procumbens
Sweet –birch Oil Betula Oil
Betula lentha
Methyl salicylate – local irritant, antiseptic, antirheumatic
aromatic compound found in Wintergreen
2. Lavender oil – lavender: Lavadula angustifolia
Lavadula vera
Lavadula officinale
– linalylacetate
3. Pine needle Oil – Pinus mugo
– bornyl acetate
4. Mustard oil – Brassica nigra
– sinigrin allyl isothiocyanate
a glycosidic volatile oil obtained by enzymatic
hydrolysis of the glycosides .
C. Cardiac Glycosides
VACCINES
a preparation containing weakened or dead microbes of the kind
that cause a disease, administered to stimulate the immune system
to produce antibodies against that disease
Clinical Designations of Skin Reactions
Types of Vaccines:
1. Attenuated whole-agent vaccines use living, but attenuated Designation Symbol Characteristics
(weakened) microbes Negative No reaction or no different from control
Examples: Mumps Doubtful No applicable difference from control
Measles (for children 15months or older) other than slight erythema
is culture in either avian embryo One-plus Erythema smaller than 20mm in
tissue or human diplod tissue diameter
Rubella Two-plus Erythema larger than 20mm but no
Chickenpox wheal
Sabin polio Vaccine (TOPV, Trivalent oral polio Definite wheal w/ surrounding
Three-plus
vaccine) erythema
2. Inactivated whole-agent vaccines use microbes that have been Four-plus Wheal with definite pseudopods &
killed, Usually by formalin or
erythema
phenol
Examples: Rabies
Influenza
Salk polio vaccine
Pneumococcal pneumonia
Cholera
Pertussis
Typhoid
3. Toxoid Inactivated toxins
are vaccines directed at the toxin produced by a pathogen
Examples: Tetanus
4. Subunit vaccine consist of an antigenic fragment of microorganism
that best stimulate a immune response
Recombinant vaccines a subunit vaccine that are made
or produced by
DNA techniques or
genetic engineering
technique
Acellular vaccines consist of antigenic parts of cell
Example: Hep B
5. Conjugated vaccines consist of the designed antigen & other
proteins
deal w/ poor immune response of children to
vaccines.
6. Nucleic Acid vaccines DNA vaccines
newest & most promising vaccine
made up of DNA, usually in the form of a
plasmid
Herb/ Healthy Foods are products of natural origin which w/out
Chamomile “Ginseng of Europe”
therapeutic effect used by the laity in the self-
Myristica Oil a volatile oil, contain Benzaldehyde
treatment disease
Canola Oil oil obtained from Rapeseed
Non-official Drugs drugs that are no longer official in the current
Breakfast Cocoa is the powdered marc after cocoa butter is
USP/NF
expressed.
Official Drugs a drug substance that is found in the current USP/NF
Pyrethrins are the insecticidal components of
Official Description a descriptive material pertaining to any of the
drugs or preparation in the USP/NF Chrysanthemum cinerariaefollium (Asteraceae)
Hypericin is the active antidepressant constituent of St. John’s Wort
Chemotherapy the study & use of chemical agents which are more Worm Seed Chemopodium ambrosioides
selectively toxic to the invading organism than to the active substance: Ascaridol (kills Ascaris)
host Datura alba for Asthma
Ilang-Ilang contain Benzyl Alcohol
Papain found in the unripe papaya tree
Plant Acids contains 2 to 3 carboxyl groups dried & purified latex of the fruit of Carica papaya
used as Meat tenderizer
Sulfated Oil/ Sulfonated Oil obtained by reacting sulfuric acid w/ the
Ergotamine alkaloid obtained from Ergot
oil, keeping the temperature down by
Glucosamine Sulfate dietary supplement that relieves pain &
chilling.
stiffness on joint & limbs
Evening Primrose for PMS
Plant Lectin (Toxoalbumins) highly poisonous Ubiquinone prevention of stroke
1. Ricin (from Castor Bean) Banana powdered leaves for Diabetes
2. Robin (from Locust Bark) Meadow Saffron Colchicum eutumnale
3. Abrin (toxic principle of Jequirity Seeds) autum crosus
was described as a treatment for rheumatism &
Factors contributing to the variability in the concentration of toxic swelling in Ebers Papyrus
components in plants may:
-plant part used Enduranz® contains Tonkat Ali, Banaba, Malungay, Guto Kola
-age of plant
-climatic & soil differences
Candida utilis Torula Yeast
Most common outcomes of the ingestion of a toxic plant: Saccharomyces cerevesiae Brewer’s Yeast
-Nausea
-Vomiting Remains after the extraction process is completed:
-Diarrhea -Menstruum liquid
-Marc solid (undissolve portion)
Weed associated w/ Polllinosis (hay fever)
- Amarathaceae
- Asteraceae
Soybean Meal a flour sifted from decorticated, ground seed of
- Chenopodiaceae
Glycine soja deprived of fat
– used in the detection of BUN
Belong to Fam. Lamiacease:
- Spearmint
Photosynthesis where the primary function of plants not present in
- Rosemary
animals but on animal & man depend greatly
- Peppermint
Pollination transfer of pollen from the anther to the stigma
- Thyme
Chlorophyll A There is methyl substitution in one of the pyrrole rings
Picrotoxin central depressant no ready interconversion
Muscarine most poisonous & non-edible mushroom contain 3:1 (ratio of chlorophyll A)
Linamarin & Manihotoxin toxic cyanogens found in Cassava. Chlorophyll B Occurs in Ferns, mosses & algae
Cassave (Manihot Esculenta) There is an Aldehyde substitution in one of the pyrrole
Kamoteng Kahoy rings
Calcium Oxalate end product of acid formation in the plant & occurs
as insoluble calcium salt or raphide
Plantid Pigment commonly extracted by Acetone
5’ 3’ DNA A G T A C G A T A G
▪Polymerase activity strand T C A T G C T A T C CODING
3’ 5’
3’ 5’ U C A U G C U A U C
STRAND
RNA
▪Exonuclease activity 5’
transcript 3’
(removal of
nucleotide from 3’
Antiparallel: “Each end of the DNA helix contains the 5’ end of
5’ direction)
one strand & the 3’ end of the other strand.”
▪Proof reading ability
2. RNA polymerase does not require a primer
5’ 3’
can initiate polymerization
▪Exonuclease activity
does not posses proof reading activity
(removal of RNA
Primer a short piec of nucleic acid (DNA or RNA), base-
primers)
paired w/ a DNA template strand & provides a
free 3’-OH end from which DNA polymerase
8. DNA ligase connect the okazaki fragments
can extend a DNA strand
Okazaki Fragments discontinous stretches in which the lagging
Rifampicin binds to bacterial RNA polymerase
strand is initially synthesized during DNA
1. mRNA act as template for translation (synthesis of protein)
replication
carrier of codons
mutation (occurs in DNA mismatch) sequence of 3 nucleotides
specifying an amino acid
2. tRNA adaptor molecule of amino acid
carrier of carrier of anticodon
The Sequence of the Major Events in DNA Replication: sequence of 3-nucleotide
1. DNA double helix is opened by helicases complementary to a specific
2. Primase creates a temporay RNA primer for each DNA strand codon.
3. DNA polymerase at the replication fork synthesize DNA in 5’ to 3’ AUC =aniticodon of AUG, methionine
direction. There are two strands, the leading & lagging strands.
3. rRNA together w/ other proteins make up the ribosomes
4. DNA polymerase removes RNA primer & fills the gaps between the
Okazaki fragments ribosomes – site of protein synthesis.
5. DNA ligase joins DNA fragments of the lagging strand, creating a 30s 5s rRNA + 16s rRNA + 20 other proteins
single DNA molecules 50s 25s rRNA + other proteins
Translation
synthesis of proteins based on the codons specified by the mRNA
process by which the genetic messages are decoded & used to
build proteins
process determining amino acid sequence; the process by which
information in messenger RNA directs the sequence of amino
acids assembled by a ribosomes during protein synthesis
Translation
mRNA Proteins
-anomer -anomer
Alpha Anomer most stable anomer of glucose
Glucose is the most important carbohydrate OLIGOSACCHARIDES condensation product of 2 -10 monosaccharides
is the major metabolic fuel of mammals (except ruminant) Examples: Maltotriose 3 glucose units
& a universal fuel of the fetus Dextrin
is stored in the liver as Glycogen Trisaccharide: Raffinose (Melizitose, Melitriose)
present in Human Blood: 60 to 90 mg in 100 mL blood Gentianose
POLYSACCHARIDES 2. Structural Polysaccharide
condensation product of more than ten monosaccharides a. Cellulose is the chief constituent of the framework of plant
may be linear or branched polymer most abundant organic compound in the world
sometimes classified as hexosan or pentosans, depending upon b. Pectin has a structure that is known to be linear
the identity of the constituents monosaccharides polygalacturonic acid.
▪ Pentosans: Araban (gum Arabic) extracted from plants exhibit remarkable jelly-
Xylan (coin cobs) forming capacity
▪ Hexosans: a. Glucans – starch, dextrin, cellulose generally present in the cell wall
b. Fructan – inulin c. Alginic Acid is also linear-like pectin & cellulose
c. Mannans
found in brown algae & kelp (seaweed)
d. Galactans (guso)
used as thickeners, emulsifiers, stabilizer, & as
1) Homopolysaccharides only 1 type of monosaccharide
hydrophilic agent in medical & cosmetic ointment
▪Glucans (glucose) bases.
1. Cellulose structural polysaccharides in plant; d. Carragheenan found in red seaweeds
-1,4 (linear)
used in preparation of chocolate drinks to hold
dietary fiber
cocoa particles
2. Starch Storage of Polysaccharide In plants used in the treatment of peptic ulcer when
components: degraded
Amylose Amylopectin e. Agar occurs in red algae, Gelidium cartilagenium
-amylose -amylose used in making make-ups
Linearity Linear Branched contains two fractions:
- 1,4 (every 25-30 units)
Agarose
- 1,4 & -1,6
Agaropectin
3. Glycogen – storage polysaccharides in animals
f. Chitin is the structural polysaccharide in the exoskeleton
(highly branched) more branched than starch
of crustaceans (an animal with hard shell, usually
1-4; 1-6 (branches every 8-12 units)
living a water, e.g. crabs) & insects & also in
stored in the liver & skeletal muscles
mushrooms & in slimming capsules
▪ Chitin
Chitin structural polysaccharides in animals & fungi 3. Glycosaminoglycans (mucopolysaccharides)
homopolyglycan of N-acetylglucosamine (NAG) mixed polysaccharides
repeating units of chitin are complex carbohydrates characterized by their content of
found in exoskeleton amino acids & uronic acids,
2) Heteropolysaccharides more than one type of when attached to proteins, result is proteoglycan
polysaccharides Proteoglycan provide the ground or packing substance of
Repeating units: Disaccharides connective tissue
Ex: Hyluronic Acid from “hyalos” (means glass) a. Heparin possesses anticoagulant properties
vitreos humor prevent the clotting of blood by inhibiting the
synovial fluids conversion of prothrombin to thrombin
Chondroition SO4 chondros (clotting factor)
Dermatan SO4 skin
b. Hyaluronic Acid appears to serve as an integral part of the gel-
Keratan SO4 nails
like ground substances of the connective
Heparan SO4 anticoagulant
tissue, & other tissues, & a lubricant & shock
Agarose seaweeds
absorber in joints.
Peptidoglycan important component of cell wall of gram(+) present in the synovial fluid of joints, in
bacteria vitreous humor (found in eyes) & in the
is a cross-linked, multi-layered polysaccharide-
umbilical cord.
peptide complex used as the basis of Gram
c. Chondroitin Sulfate principal mucopolysaccharides on the
staining
extracellular ground substance & also in cell
-N-acetylglucosamine (NAG)
coats.
-N-acetylmuramic Acid (NAM)
are major components of cartilage, bone,
Types of Polysaccharides based on their biological function:
cornea, & other tissue structure in the
1. Storage Polysaccharides
vertebrates
a. Starch primary reserve carbohydrates in plants.
most abundant dietary carbohydrate in cereals,
potatoes, legumes, & other vegetables
4. Glycoproteins (mucoproteins) occurs in many different situations in
composed of Amylose & Amylopectin
fluids & tissues, including the cell
b. Glycogen is the storage polysaccharide in animal tisues membranes
similar to amylpectin, but more highly branched than are proteins containing branched or
amylopectin unbranched oligosaccharide chains
c. Inulin is a polysaccharide of fructose ( & hence a fructosan), a. Sialic Acid are N- or O-acyl derivatives of neuramic acid
found in tubers, & roots of daqblias, artichokes, & are both constituents of glycoproteins & gangliosides
dandelions Gangliosides a lipid occurring in the brain, nerves, and red
readily soluble in water blood cells
used to determine the Glomerular Filtration Neurominic Acid is a nine-carbon sugar derived from
d. Dextrans storage polysaccharides found in yeast & bacteria monosamine (an epimer of glucosamine) &
is strongly coiled & flexible macomolecules pyruvate
used as plasma expander
Dextrin are intermediates in the hydrolysis of
starch
Isomers are compounds w/c have the same molecular formula, but
have different atomic arrangement
Types of Isomers:
1. Functional Isomers differ in their physical properties
Ex:
Reactions of Carbohydrates:
1. Dehydration (action of Acid)
a. Molisch Test aka “Alpha-Naphthol Reaction”
general test for Carbohydrates
Dimethyl Ether Ethyl Alcohol gives purple colored ring
2. Stereoismers different arrangement of atoms or groups in three b. Bial’s Test for pentoses
dimensions. yields Green Color (sometime blue)
a. Geometrical or Cis-Trans Isomers the trans isomers are more
c.Tollen’s Test uses Ploroglucinol
stable than the cis isomers
gives violet-red color
Ex:
d. Seliwanoff’s Test aka “Resorcinol Test for Ketones”
indicates the presence of ketones
differentiating test for aldose & ketose sugars
gives rose pink color/ cherry red color
e. Tauber’s Test aka “Aminoguanidine Reaction”
Trans-Butynedionic Acid Cis-Butynedionic ACid for ketoses, yeilds bright Reddish purple color
(Fumaric Acid)
b. Optical Isomer also called as optical antipodes, or enantiomorphs, 2. Reaction w/ alcohols: Acetal or Glycoside Formation
or enantiomers. when an aldehyde reacts w/ 2 equivalents of alcohol,
▪ Dextrorotatry (+)a substance whose solution rotates the plane of the products is ACETAL.
polarized light to the right
▪ Levorotatry ()a substance whose solution rotates the plane of 3. Reactions w/ Oxidizing Agents: Reducing Sugars
polarized light to the left Reduction Tests:
Ex: a. Benedicts Reagent Cu2+ & Sodium Citrate (color Blue)
Traces sugar =geen
Moderate amount = yellow
and or yellow orange
Big amount of sugar = red orange or red
b. Barfoed’s Test Copper Acetate, Acetic Acid
c. Anomers difference resides in the steric arrangement about used to distinguished monosaccharides from
carbon atom one, carbonyl carbon of the linear formula disaccharides
& the ketonic carbon ex: Galactose from Lactose
these carbons are called “Anomeric Carbon Atom” Maltose from Fructose
d. Epimers differ only in the configuration of a single asseemtric c. Mucic Acid Test used to demonstrate either lactone or
carbon atom galactose or both
d. Fehling’s Test Cuprous Oxide (-indicator)
Confiramatory test for Glucose
detect Aldehydes & Sugar
gives a positive result brick red precipitate
pH of the Solution lies the difference between Benedict’s &
Barfoed’s Test reagent
4. Reduction of Monosaccharides
5. Reaction w/ Phenyhydrazine
6. Fermentation anaerobic process
hydrolysis of carbohydrates into simple alcohols &
ketones by microorganisms
7. Ester formation
Lipids permanent storage of energy
are water-insoluble organic substances found in cells, which
are soluble in non polar solvents such as chloroform, ether,
methanol, hexane, & benzene
heterogenous group of compounds
composed of five element:
Carbon, Hydrogen, Oxygen, Nitrogen, Phosphorus
CLASSIFICATIONS:
I. Storage/ Neutral Lipids 2. Unsaturated fatty acids
A.Triglycerides/ Triacylglycerols (TAGs) Monounsaturated/ Monoenoic Acid: (one double bond)
ester of glycerol fatty acids ▪ Palmitoleic Acid (16:1 ) contains 16C w/ 1 double bond
9
storage form of fatty acids in humans
(cis-9-hexadecanoic acid)
▪ Oleic Acid (18:1 ) at position between 9&10
9
(cis-9-octadecanoic acid)
▪ Elaidic Acid (18:1 ) (trans-9-octadecanoic Acid)
9
Phosphatidylcholine (Lecithins)
phosphoacylglycerol containing choline
are the most abundant phospholipids of the cell
membrane & represent a large proportion of the body’s
store of choline
a substance also present in soybean that can be found
in number of proprietary products that are useful in
Phosphatidylethanolamine controlling derange lipid & cholesterol metabolism
Phosphatidylcholine (Lecithin) Choline is important in nervous transmission, as
(Cephalin)
acetylcholine, as a store of a labile methyl groups
Rosenheim’s Test used to detect the
presence of Choline
form White Crystalline ppt.
Dipalmitoyl Lecithin is a very effective surface active agent
& major constituents of the
“surfactant” preventing adherence,
due to surface tension, of the inner
Phophatidylinositol Phosphatidylglycerol surfaces of the lungs.
its absence from the lungs of
premature infants cause
“Respiratory Distress Syndrome”
Phosphatidylethanolamine (Cephalin) Plasmalogen
Phosphatidylserine (found in most tissue)
differ from phosphatidylcholine nly in that
ethanolamine / serine, respectively replaces choline.
Phosphatidylserine
B. Sphingolipids sphingosine, fatty acids, polar head group III. Terpenoids
amide bond polymers of Isoprene Units
Ceramide amide of sphingosine + fatty acids fat soluble vitamin (ADEK)
parent compound of Sphingolipids
+ phosphocholine/ phosphoethanolamine sphingomyelins Vitamin A general antioxidant by singlet oxygen quencher
+ monsaccharide (glucose/galactose) cerebrosides maintains the integrity of epithelial membranes
Neutral + disaccharides/ neutral oligosaccharide globosides essential in the formation of rhodopsin & the normal
+ charged oligosaccharide ganglioside () functioning of the retina
Because of N-acetylneuraminic Acid was the first fat-soluble vitamin discovered
(sialic Acid) Retinol major natural form of Vitamin A
Carotenoids ,,-carotenes (pro vitamin A) orange
Sphingophospholipids – the alcohol is Sphingosine Zeaxanthine & Lutein yellow
Glyrophospholipids – the alcohol is Glycerol (these compound can be
Glycolipids (Glycosphingolipids) – lipid containing fatty acids, converted to Vitamin A)
sphingosine, & carbohydrates Lycopene red
are important in nerve tissues & Most effective singlet oxygen quenchers
in the cell membrane Carrots good source of Vit A
Cerebrosides are lipids that contain carbohydrate Vitamin D synthesized in the skin through the action of sunlight
(galactose or glucose), one fatty acid & Calciferol
sphingosine but no phosphoric acid or Other Forms of Vitamin D:
glycerol 1. Ergocalciferol (Vit D2) plant steroid ergosterol
are positive in Molisch & Lassaignes Tests 2. Colecalciferol (Vit D3) animal species
found in high concentration in brain & 3. Dihydrotachysterol is a synthetic substance formed by
nerve cells the reduction of tachysterol
Galactosylceramide is a major glycosphingolipids in brain closely related to ergosterol
& other nervous tissues 4. 7-Dehydrocholesterol is converted to calciferol upon
Glucosylceramide is the predominant simple exposure to ultraviolet light
glycosphingolipid or extraneural Cod Liver Oil good source of Cod Liver Oil
tissues Vitamin E prevents lipid peroxidation
Gangliosides are complex glycosphingolipids derived from
truly antiaging vitamin
glucosylceramide that contain in addition
Vitamin K important in blood coagulation
one or more molecules of a sialic acid.
are compounds related to cerebrosides that
contain sphingosine, long-chain fatty acids,
hexoses (usually galactose or glucose), &
neuraminic acid. Lypolysis is a triglyceride hydrolysis
Neurominic acid is the principal sialic acid found in liberates free fatty acid from their main storage
human tissues. depots in the triglycerides
Cytopilins contain fatty acids, sphingosine, glucose & begins in the intestinal hydrolysis of dietary
galactose triglycerides by pancreatic lipase
Sphingosine complex amino alcohol Nitrogen Balance difference between intake & output of
Sphingomyelins are found in the nervous system nitrogenous compounds
yield fatty acids, phosphoric acid, holine, & a - Intake = Output Equilibrium Nitrogen Balance
complex amino alcohol(sphingosine) - Intake < Output Negative Nitrogen Balance
Lysophospahtidylcholine or Lysolecithin
occurs when dietary
are intermediate in the metabolism
intake is less than
of phosphoglycerols
excretion of
nitrogenous
C. Sterols precursor in the synthesis of sex hormones
compounds
Stigmasterol, Sitosterol – plants
occurs during
Ergosterol – fungi
Starvation
Cholesterol – animals
- Intake > Output Positive Nitrogen Balance
very important as structural component of all membrane
results when there is
for synthesis of sex hormones & bile acids
too much protein
for rigidity & fluidity of cell membrane structure
intake
Examples of Bile Acid derived form Cholesterol:
Liver: Cholic Acid, Chenodeoxycholic Acid
Intestine: Deoxycholic Acid, Lithocholic Acid
Bile Acid – produce in the liver but store at gallbladder.
IV. Eicosanoids aka “Arachidonic Acid”
compounds derived form eicosa-(20-carbon) polyenoic
fatty acids
Examples: (for fever, pain & inflammation)
Prostanoids via the cyclooxygenase pathway
Prostaglandin PG: PGE1, PGE2, PGF2 ;
derivatives of Prostanoic Acid
exist in virtually every mammalian tissue,
acting as local hormones.
a hormone-like substance that is Salkowski Test (Sulfuric Acid Test)
released by damaged cells, intensifies test for Cholesterol
inflammation Positive visible result: Play of colors from bluish-
lipid metabolite formed in the body from red to cherry-red & purple
essential unsaturated fatty acids from in the chloroform layer, &
the diet the acid layer assuming a
Linoleic Acid most important dietary marked green fluorescence
precursor of Liebermann-Burchard Test (Acetic Acid-Sulfuric Acid Test)
prostaglandins test for Cholesterol
Seminal Fluid contains the highest Positive visible result: The solution becomes red,
concentration & greatest then blue, & finally bluish
number of prostaglandins green in color
Main classes of PG: A, B, E, & F
Prostacyclin PGI2
Thromboxane TXA2
for platelet aggregation,
inhibited by Aspirin.
Aspirin cannot dissolve clots but
it can prevent through
the action of TXA2
Leukotrienes LT: LTB, LTC, LTD ;
for inflammation & bronchoconstriction
is a product of arachidonic acid
metabolism via the lipooxigenase
pathway
Rotenone blocks the transport from NADH to Q Acetyl CoA + OAA Citrate
Antimycin-C blocks the transport from Q to Cytochrome-C 2C
CN/ CO blocks the transport from Cytochrome-C to O2 Acetyl CoA 2CO2 + 3 NADH + 1 FADH2 + GTP
2C
3 NADH x 3 9
Superoxide Anions is the product of the complete reduction 1 FADH2 x 2 2
of oxygen 1 GTP x1 1
Hydrogen Peroxide & Hydroxyl Radicals are the products of 1 Acetyl CoA 12 ATP
the partial
reductionof oxygen Overall reaction:
▪Acetyl CoA + 3 NAD+ + GDP + FAD+ 3 NADH + GTP + FADH2 + 2CO2
Krebs Cycle:
Steps:
1. Acetyl CoA adds to oxalacetic acid in aldol reaction & the bond to
coenzyme A is hydrolyzed to yield citric acid.
2. Citric Acid is isomerized by transfer of the OH group to yield isocitric
acid.
3. Isocitric Acid loses CO2 & is oxidized to yield -ketoglutaric acid.
4. -ketoglutaric acid reacts w/ coenzyme A & loses CO2 to yield
succinyl CoA.
5. Succinyl CoA is hydrolyzed to give succinic acid plus CoA. An ADP
molecule is also converted into ATP by an indirect series of steps.
6. Two Hydrogens are removed from succinic acid to yield fumaric
acid. The coenzyme FAD is needed in this reaction.
7. Addition of Water to the double bond of fumaric acid yields malic
acid.
8. The cycle of reaction is completed by oxidation of malic acid to
regenerate oxaloacetate acid.
Control Points:
~ The Citrate Reaction, which is inhibited by ATP
~ Isocitrate-dehydrogenase Reaction, which is inhibited by ATP
Isocitrate Dehydrogenase activated by ADP
~ -ketoglutarate dehydrogensa Reaction, which is inhibited by the
end products Succinyl CoA
& NADH
Glycolysis Glucose Pyruvate ATP-consuming stages in Glycolyis:
Insulin: glucose
Glycogenesis Glucose Glycogen ~ Irreverdible Phosphorylation of fructose-6-phosphate
to fructose-1,6-biphosphate
Glycogenolysis Glycogen Glucose
Gluconeogenesis Non carbohydrate Glucagon: ~ Phosphoenolpyruvate to Pyruvate
precursor glucose level
Glucose
activate Epinephrine
-Adrenaline rash causes diabetic coma
-very dangerous in diabetic people
Glucagon homone that sometimes useful in the reversal of
cardiac effects of Beta-blocker overdose because of its
ability to increase cAMP production in the heart
ATP ADP catalyzed phosphate to ATP Glucose end product of Glycolysis of Glycogen
hexokinase –has higher affinity to glucose Glucose-6-phosphatase employed to bypass the hexokinase reaction
single headed = irreversible reaction its deficiency predisposes persons taking
some therapeutic agents (ex:
3. Fructose-6-PO4-3 PFK-1Fructose-1,6-biphosphate
Aminoquinoline, Sulfonamides,
Propantheline) to hemolytic anemia
Stage 2: Pay-off Phase
is present only in the liver & kidney & not in
Glycerol Phosphate shuttle (x2)
the muscle
MalateAspartate shuttle (x3)
Hexokinase glucose to glucose-6-phosphate
most important enzyme in controlling glycolysis
NADH NADH
Fructose biphosphatase used to bypass the PFK reaction
Cytosol GPS MAS
Pyruvate Carboxylase & PEP Carboxykinase used to bypass the
Mtochodria
pyruvate kinase reaction
FADH2 NADH
of glycolysis
Pyruvate Kinase is the key enzyme that likns lycolysis, TCA cycle,
amino acid metabolism, & fatty acid oxidation
PFK (Phosphofructokinase) Fructose-6-PO4 to Fructose-1,6-bisPO4
most important in controlling glycolysis
responsible for rate limiting step in
Glycolysis
Minor Pathways for Carbohydrates Metabolism:
Glycogenolysis Pentose Phosphate Pathway (aka Hexose Monophosphate Shunt)
(catabolism); a metabolic pathway that can occur simultaneously with
conversion of glycolysis to produce pentose & NADH without ATP
glycogen to glucose production
occur in Liver occur in the cytosol of liver, muscle & kidney
1. Production of NADH
2. Production of Ribulose-5-PO43- ribose
3. Metabolism of Pentoses
3glucose 3CO2 + 3 ribose (5-carbon atom)
Unsaturated
assume as saturated Bothe
Example: Ketogenic Glucogenic Ketogenic &
Oleic Acid (18:149) Glucogenic
9 Acetyl CoA x 12 = 108 Leucine Valine, etc Phenylalanine
8 NaDH x 3 = 24 Lysine Tyrosine
8 FADH x 2 = 16 Tryptophan
= 148 ATP Isoleucine
= -2
= 146 ATP
(For double bonds)= -2
= 144 ATP
Oleovitamin A & D found in liver oil or other vegetable oil. Chromium Def Glucose Intolerance
Peripheral Neuropathy
Vitamin B Complex used in the prevention of degenerative changes in the Metabolic Encephalopathy
central nervous system.
Zinc Def Alopecia
Vitamin B1 (Thiamine) Appebon® Infertility
occur in greatest proportion in dried yeast Poor wound healing
can treat Wernicke-Korsakoff Syndrome Poor growth
most rapidly reduced vitamin Poor resistant to infection
Defficiency: Pernicious Anemia
Copper Def Depigmentation of Hair
Vitamin B3(Niacin) can be used in the management of hyperlipidemia
MOA: Inhibition of VLDL secretion Selenium Def RBC Fragility
naturally occurring pyridine derivative that prevents
Pellagra
manifestations of Pellagra:
- Dementia (CNS disorder)
- Diarrhea
- Dermatitis