BIOCHEMISTRY Composition of the Cell Membrane

MODULE 2 Lipids
● Bios - Life Phospholipids
● Chemistry - Study of structure, properties, composition and changes of matter ● Major type of lipid in the cell
● Definition - The branch of science concerned with the chemical and physicochemical membrane
processes and substances that occur within living organisms ● Composition
○ Alcohol (R)
THE CELL ○ Phosphate group
● The basic unit of life ○ Platform (Glycerol or
○ Atom - Basic unit of matter Sphingosine)
○ Cell → tissue → organ → organ system → organism ○ One or more fatty acids

The 3-Domain System: Carl Woese’s Domains of Life

1. Bacteria (Prokaryote) 2 Types of Phospholipids
2. Eukarya (Eukaryote) - 3 Kingdoms: 1. Phosphoglycerides - Platform is Glycerol/Glycerin and 2 Fatty Acids
a. Animalia - Animals, including mammals, helminths, and insects 2. Sphingolipids - Platform is Sphingosine and 1 Fatty Acid
b. Plantae - Plants
c. Fungi - Molds, yeasts, mushrooms Glycolipids
d. Protozoa - Protozoans (1st animals)
3. Archaea (Prokaryote) ● Aka Glycosphingolipids
● Conjugates of lipids and sugars
Parts of an Animal Cell ● Cerebrosides - Simplest
Cell Membrane ○ Sugar is either glucose or galactose
● Outermost part of an animal cell (Glucocerebrosides or
○ Plant cells, bacteria cells, fungal cells have the CELL WALL as its outermost part. Galactocerebrosides)
→ Plants - Cellulose → Monosaccharides
→ Bacteria - Peptidoglycan ● Globosides - Both glucose and galactose
→ Fungi - Chitin ● Gangliosides - Most complex
● Aka Plasma Membrane ○ Sugars are oligosaccharides (3-10 sugar units), and also has sialic acid (nonose, 9C
● Composed mainly of 2 layers of phospholipids that create a barrier to the flow of polar sugar)
compounds such as water
○ 1 layer only → can’t control movement of polar compounds Cholesterol

1. Too much water enters a cell → swell → burst (too much osmotic pressure → LYSIS ● A steroid (Cyclopentanoperhydrophenanthrene
2. Too much water goes out of a cell → shrink → CRENATION nucleus)
● Regulates membrane fluidity
a. Membrane is too fluid → Cannot maintain the cell
shape
b. Membrane is too rigid → Tends to break easily
Effects of Body temperature
a. ↓ Body Temperature → CM is Rigid
● Cholesterol intercalates between phospholipids preventing them from clumping together and
stiffening
b. ↑ Body Temperature → CM is Fluid
● Cholesterol increases the melting point of the cell membrane

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 Proteins Organelles
● Small organs that have a specific function inside a cell
● Suspended in a gel-like matrix called the CYTOPLASM or CYTOSOL
Passive Transport Active Transport

● No energy requirement ● Energy-requiring, from: Mitochondrion

● Downhill movement ○ ATP Hydrolysis ● Powerhouse of the cell
● Where Adenosine Triphosphate (ATP) is being synthesized via oxidative phosphorylation
2 Types of Passive Transport ○ When ATP is hydrolyzed, energy is released
1. Simple Diffusion - Not ○ Plants - Sunlight
carrier-mediated ● Uphill Parts
2. Facilitated Diffusion - ● Always carrier-mediated (is saturable)
A. Intermembrane Space
Carrier-mediated (SATURABLE - If B. Outer Mitochondrial Membrane - Made of phospholipids,
there are no carriers available, the is perforated (pores)
mechanism will stop until there will be C. Inner Mitochondrial Membrane - Has folds called cristae
more available carriers) D. Mitochondrial Matrix

Pumps
● Active transport of substances Molecule Structure
● Example - Na+-K+ ATPase Pump
● 3 Na+ leave while 1 K+ enters
○ Makes the intracellular region slightly
Adenosine
negative → RESTING MEMBRANE
Triphosphate (ATP)
POTENTIAL
● Stores energy to
→ Cell at rest has potential to transmit a
be released
nerve impulse to another cell
during hydrolysis
● Adenine +
Ribose =
Channels Adenosine
(Nucleoside) ● Phosphate or Phosphoryl Groups - 3
● Provide a membrane pore where substances ● High Energy Phosphate Bond - 2
can be transported passively ○ Phosphoanhydride bond

GABA Receptors
● Pore for Chloride ions to cross the cell
membrane
Adenosine
● Barbiturates - Prolong the opening of GABA
DIphosphate (ADP)
receptors → influx of Cl- → Hyperpolarized cells
● Benzodiazepines - Increase frequency of
● Phosphate or Phosphoryl Groups - 2
GABA receptor opening → influx of Cl- →
● High Energy Phosphate Bond - 1
Hyperpolarized cells

Carriers
● Saturable processes
● Both active and passive transport of substances

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 Endoplasmic Reticulum
Adenosine
Monophosphate
● Studded with Ribosomes
(AMP) Rough ER
● Important in Protein Synthesis
● Acts as a
secondary ● No ribosomes
● Phosphate or Phosphoryl Groups - 1 Smooth ER
messenger ● Important in Lipid (Hormone) Synthesis
● High Energy Phosphate Bond - 0

Lysosomes and Peroxisomes Golgi Bodies

● Both membrane-bound organelles ● Flattened sacs
○ Only found in eukaryotes ● Discovered by Camillo Golgi
● Function - Transporting, modifying, and packaging proteins
Organelle Enzymes Functions and lipids into vesicles for delivery to different parts of the cell
or outside the cells
● Hydrolytic ● Digestive system of the cell
Enzymes/Hydrolases ● Degrade material taken up from outside
the cell Microtubules
○ Infection control ● Facilitate cell movement, cell division (mitosis), and transportation of materials within the cells
Lysosome
○ Pathogens - Disease-causing ● Composed of tubulin (protein subunit)
organisms ● Make up the Spindle Fibers or Mitotic Spindle
● Digest obsolete (dysfunctional/old) ● Cancer Cells - Abnormal cells that are infinitely dividing until it forms a tumor
components of the cell ● Mitosis: Anaphase - Spindle fibers bind to the mitotic spindle, to separate the sister
chromatids → proceed with telophase
● Oxidases - By-product is ● Oxidation of substances
free radical (H2O2) which ● Metabolism of hydrogen peroxide Anti-mitotic Drugs
can cause cellular ○ Protects the cell against hydrogen 1. Taxanes - Inhibit microtubule depolymerization or disassembly
Peroxisome damage peroxide a. Paclitaxel
● Catalase - Breakdown ● Metabolism of fatty acids i. Taxol (Prototype) - Bark of pacific yew (Taxus brevifolia)
of H2O2 to produce H2O b. Cabazitaxel
and oxygen c. Docetaxel
2. Vinca Alkaloids - Inhibit microtubule polymerization or assembly
Ribosomes a. Vincristine
● Site of protein synthesis b. Vinblastine

Stages of Protein Synthesis Nucleus

1. Transcription - DNA-Directed RNA synthesis (Nucleus) ● Control center of the cell
2. Translation - RNA-Directed protein synthesis (Ribosomes) ● 46 chromosomes (Tightly coiled DNA strands)
● Nucleolus - Site of 40s, 60s ribosome assembly
● Nuclear Membrane - Membrane that encloses the nuclear structure
Bacteria (Prokaryotes) Animal (Eukaryotes)

Large Subunit 50s 60s

Small Subunit 30s 40s

Condensed 40s 80s

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 ● An organic molecule that binds to the active sites of certain enzymes to
BIOMOLECULES
help in the catalysis of a reaction (Redox Reaction)
● Intermediate carriers of Electrons
Organelle Enzymes Functions

Carbohydrates Monosaccharides (Simple sugars) Glycosidic Bonds

Lipids Not biopolymers

Proteins Amino Acids Peptide Bonds

Nicotinamide
Nucleic Acids (DNA, Nucleotides Phosphodiester bonds Adenine
RNA) Dinucleotide
● Needs Vitamin B3 (Niacin/Nicotinamide) to form
(NAD)
NAD
METABOLISM ● NAD+ + 1H+ + 2e- → NADH
Co-enzymes ● Electron Transport Chain and Oxidative
● Sum of the chemical reactions that take place within each cell of a living Phosphorylation
organism and that provide energy for vital processes and for ○ 1 NADH = 2.5 ATP
synthesizing new organic material.

● Breaking down of reactions

● Complex → Simple
Catabolic Flavin Adenine
○ Example - Starch → Glucose
Dinucleotide ● Need Vitamin B2 (Riboflavin)
Metabolism ● ATP-producing
(FAD)
● FAD + 2H+ + 1e- → FADH2
● Building up reactions ● Electron Transport Chain and Oxidative
Anabolic ● Simple → Complex Phosphorylation
● ATP-Requiring ○ 1 FADH2 = 1.5 ATP
● Includes both anabolic and catabolic processes
Amphibolic
● Example - Krebs Cycle
Carbohydrate Metabolism
● Insulin
Adenosine ● Energy-carrying molecule found in the cells of all living things ○ Produced by the Beta Cells of the pancreas
Triphosphate ● “Energy currency of the cell” → Alpha - glucagon
(ATP) ● Links catabolic and anabolic reactions → Delta - Somatostatin
○ Function - Intracellular transport of glucose
Oxidation ● Gain of oxygen, Loss of electrons and Hydrogen ions

Reduction ● Loss of oxygen, Gain of electrons and Hydrogen ions

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● Inside the Cell
1. Glucose is converted to glycogen
2. Glucose is converted to fat
3. Glucose metabolized to produce heat and to generate energy for the body
a. Glycolysis
b. Formation of Acetyl CoA Stages of Glycolysis
c. Krebs CYcle Investment or Preparatory Phase
d. Electron Transport Chain, Oxidative Phosphorylation ● Irreversible
● ATP is required
Glycolysis ● Glucose is prepared for oxidation
● Aka Embden Meyer of Parnas (EMP)
● Anaerobic reaction
Step Substrates Reaction Enzyme
● Occurs in the Cytosol/Cytoplasm
● Overall Reaction Glucose, Glucose-6-Phosphate Phosphate/Phosphoryl
1 Hexokinase
● Reversal (R) - G6 Phosphatase Group Transfer

Glucose-6-Phosphate, Phosphoglucoisomerase
2 Isomerization
Fructose-6-Phosphate (Isomers) (PGI)

Fructose-6-Phosphate,
Phosphoryl Group Phosphofructokinase
3 Fructose-1,6-Bisphosphate
Transfer (PFK)
● R - Fructose-1,6-Bisphosphatase

Cleavage

Step Substrates Reaction Enzyme

Fructose 1,6 Bisphosphate (6C) →

4 Glyceraldehyde-3-Phosphate (3C) and Aldol Cleavage Aldolase
Dihydroxyacetone Phosphate (3C)

Dihydroxyacetone Phosphate (Ketone), Triose Phosphate

5 Isomerization
Glyceraldehyde-3-Phosphate (Aldehyde) Isomerase (TPI)

5
Pay-off Phase Step Reaction Site Enzyme

Reduction of Oxaloacetate to Malate and Oxidation

Step Substrates Reaction Enzyme
of NADH
1
6 Glyceraldehyde-3-Phosphate Glyceraldehyde-3-Phosphate Redox Aldolase ● Electrons and Hydrogen ion will be from
NADH Malate Dehydrogenase
Phosphoryl
7 1,3-Bisphosphoglycerate 1,3-Bisphosphoglycerate PG Kinase 2 Oxidation of Malate to Oxaloacetate
Group Transfer

Phosphoryl 3 Reduction of NAD+ Mitochondrial

8 3-Phosphoglycerate 3-Phosphoglycerate PG Mutase Matrix
Group Shift
Transamination of Oxaloacetate to Aspartate
4
9 2-Phosphoglycerate 2-Phosphoglycerate Dehydration Enolase (Aminoacetate) Aspartate-Aminotransferase
(AST)
Phosphoryl 5 Transamination of Aspartate to Oxaloacetate Cytosol
10 Phosphoenolpyruvate (PEP) Phosphoenolpyruvate (PEP) Pyruvate Kinase
Group Transfer

Pyruvate Pyruvate
● Energy Yield - 2 NADH x 2.5 ATP’s = 5 ATP

Glycerol-Phosphate Shuttle
Phosphorylation

1. Substrate-Level Phosphorylation
● Transfer of a Phosphoryl to organic molecules (example, ADP) to produce ATP
● 4 ATPs (Produced) - 2 ATPs (Used Up) = 2 ATPs

2. Oxidative Phosphorylation
● Electrons derived from NADH and FADH2 combine with O2, and the energy released from
these oxidation/ reduction reactions is used to drive the synthesis of ATP from ADP
● Occurs in the mitochondrion
● Occurs in brain and muscle
Malate-Aspartate Shuttle
Step Reaction Site Enzyme

Cytosolic
Dihydroxyacetone phosphate is reduced to form
1 Glycerol-3-Phosphate
Glycerol-3-phosphate
Dehydrogenase

Mitochondrial
Glycerol-3-phosphate is oxidized to
2 Mitochondrion Glycerol-3-Phosphate
Dihydroxyacetone Phosphate
Dehydrogenase

● Energy Yield - 2 FADH2 x 1.5 ATP = 3 ATP

Summary of Products for Glycolysis

● 1 NADH = 2.5 ATP’s
● 1 FADH2 = 1.5 ATP’s

● Occurs in heart, liver and kidney cells

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 Malate Aspartate Glycerol Phosphate

Oxidative Phosphorylation 5 3

Substrate-Level 2 2
Phosphorylation

Total 7 ATP 5 ATP

Formation of Acetyl CoA

● Aka Oxidative Decarboxylation Reaction
● Site - Mitochondrion

Aerobic
● Enzyme - Pyruvate decarboxylase

● Irreversible
● CO2 must remove carboxyl group to make 2C molecule
● Pyruvate - Small structure → can pass outer and inner membrane of mitochondrion

Anaerobic
● Site - Cytosol
● Enzyme - Lactate dehydrogenase
● Accumulation of Lactic Acid (Lactate) leads to Muscle Pain and Fatigue
● Reversible

Formation of Acetyl CoA

● Aka Citric Acid Cycle, TCA, Tricarboxylic Acid Cycle
● Elucidated by Hans Krebs
● Site - Mitochondrial Matrix
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 Step Intermediates Enzyme Reaction Products Electron Transport Chain, Oxidative Phosphorylation
● Last step of cellular respiration
1 Acetyl CoA + Oxaloacetate → Citrate Citrate Synthase Condensation Citric Acid ● Site - Inner Mitochondrial Membrane
○ Complexes or Electron Carriers
2 Citrate → Isocitrate Aconitase Isomerization Isocitrate
1. NADH Dehydrogenase - Will oxidized NADH (Remove 2e- and 1H+)
Isocitrate 2. Succinate Dehydrogenase Coenzyme Q10 (Ubiquinone)
3 Isocitrate → 𝛂-Ketoglutarate 𝛂-Ketoglutarate 3. Cytochrome BC, Cytochrome C
Dehydrogenase
Oxidative
Decarboxylation 4. Cytochrome OXidase
𝛂-Ketoglutarate ● Chain of reaction that converts energy from oxidation of NADH and FADH2 to proton-motive
4 𝛂-Ketoglutarate → Succinyl CoA Succinyl CoA
Dehydrogenase
force, which is used to synthesize ATP
Succinate ● Series of electron transfer to Oxygen while simultaneously releasing energy and heat
Hydrolysis Succinate, CoA ● The electron flow occurs in 4 large protein complexes embedded in the inner mitochondrial
Thiokinase
Succinyl CoA → Succinate membrane
5
● Substrate level Guanosine
Succinyl CoA
Condensation diphosphate
Synthetase
(GDP)

Succinate
6 Succinate → Fumarate Oxidation Fumarate, FADH2
Dehydrogenase

7 Fumarate → Malate Fumarase Hydration Malate

Malate Oxaloacetate,
8 Malate → Oxaloacetate Oxidation
Dehydrogenase NADH

● Substrates - Our City Is Kept Safe and Secure From Monsters

● Energy Yield
● 1 NADH = 2.5 ATP’s
● 1 FADH2 = 1.5 ATP’s

● 2 Acetyl coA’s, ● Glucose Metabolism

● 6 NADH x 2.5= 15 ○ Produce heat for the body
● 2 FADH2 x 1.5=3 ○ Generate energy
● 2 ATP’s via SLP= 2
Other Important Pathways
Total - 20 ATPs
Pentose Phosphate Pathway
● Aka Hexose Monophosphate (HMP) Shunt
● Summary of Products ● Branches from glucose 6-phosphate (G6P), produces NADPH and ribose 5-phosphate (R5P),
and shunts carbons back to the glycolytic or gluconeogenic pathway
● Malate Aspartate Pathway = 7 ATP
Glycolysis
● Glycerol Phosphate Pathway = 5 ATP

Formation of Acetyl CoA ● 5 ATP

Krebs Cycle ● 20 ATP

Total ● 30-32 ATP (Brain, Muscle-Heart, Liver, Kidney)

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 ● Drugs that are CONTRAINDICATED
○ Sulfonamides (Co-Trimoxazole)
○ Antimalarials (Primaquine)
○ Quinolones (Ciprofloxacin)
○ Nitrofurans (Metronidazole)

Gluconeogenesis
● Formation of new glucose units from non-carbohydrate precursors
● Precursors
○ Glycerol from fats
○ Glucogenic Amino Acids
○ Pyruvate or Pyruvic acid
○ Lactate or Lactic Acid (Cori Cycle, reversible)

Step Reaction Enzymes

1 Pyruvate → Oxaloacetate Pyruvate Carboxylase

2 Oxaloacetate → Phosphoenolpyruvate (PEP) PEP Carboxylase

3 Phosphoenolpyruvate ⇋ 2-Phosphoglycerate Enolase

4 2-Phosphoglycerate ⇋ 3-Phosphoglycerate Phosphoglycerate Mutase

5 3-Phosphoglycerate ⇋ 1,3-Bisphosphoglycerate Phosphoglycerate Kinase

Glucose-6-Phosphate Dehydrogenase Deficiency
● NADPH is the reducing agent of Glutathione Glyceraldehyde-3-Phosphate
6 1,3-Bisphosphoglycerate ⇋ Glyceraldehyde-3-Phosphate
● Glutathione protects RBCs (120 days life) from oxidative attack Dehydrogenase
● Absence or Deficiency of G6PD - Little or no NADPH → Glutathione is oxidized → RBs die 7 Glyceraldehyde-3-Phosphate ⇋ Fructose-1,6-Bisphosphate Aldolase
prematurely (Hemolytic Anemia)
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 8 Fructose-1,6-Bisphosphate → Fructose-6-Phosphate Fructose-1,6-Bisphosphatase Diseases on Carbohydrate Metabolism
Hyperglycemia
9 Fructose-6-Phosphate ⇋ Glucose-6-Phosphate Phosphoglucoisomerase (PGI) ● Too much glucose in the blood
● Complications
10 Glucose-6-Phosphate → Glucose Glucose-6-Phosphatase
○ Damage to the retina or Retinopathy
○ Damage to the nephrons or Nephropathy
Glycogenesis ○ Damage to the neurons or Neuropathy
● Formation of glycogen (2k-60k glucose units) from excess glucose Diabetes Mellitus
● Regulated by Insulin
Type 1 Type 2
Step Reaction Enzymes
● No insulin ● With insulin
1 Glucose ⇋ Glucose-6-Phosphate Hexokinase ● Damage to the 𝛃 cells ○ Not released fast enough
2 Glucose-6-Phosphate ⇋ Glucose-1-Phosphate Phosphoglucomutase ● Autoimmune ○ Target tissues have reduced
● Juvenile-onset responsiveness to hormone(insulin
3
Glucose-1-Phosphate → UDP-Glucose
Glucose-1-Phosphate Uridyl Transferase ● Aka Insulin-Dependent DM resistance)
● UDP → urine DIphosphate ● Treatment ● Adult onset
○ Insulin Preparations ● Aka Non-insulin Dependent DM
4 UDP-Glucose → Unbranched Glycogen Glycogen Synthase
→ Porcine Insulin (Sus scrofa) ● Treatment
Unbranched Glycogen → Branched Glycogen → Bovine Insulin (Bos taurus) ○ Oral Hypoglycemic Agents (OHAs)
● Unbranched Glycogen - All alpha-1,4-glycosidic → Human Insulin → Metformin
bond ⬩ Produced by Eli Lilly
5 Branching Enzyme
● Branched Glycogen - Have alpha-1,6-glycosidic ⬩ Via Recombinant DNA
bond between 2 glucoses
Technology
○ Stored in liver and skeletal muscles
⬩ Microbe - E. coli

Glycogenolysis
Glycogen Storage Diseases
● Breakdown of glycogen
● Formation of glucose from glycogen
● Regulated by GSD Type Other Name Enzyme Deficient
○ Glucagon - From 𝛂-cells of pancreas
0 Glycogen Synthase
○ Epinephrine or Adrenaline - Emergency hormone
I Von Gierke Glucose-6-Phosphatase
Step Reaction Enzymes
Alpha-1,4-Glucosidase or Acid Maltase
II Pompe
1 Branched Glycogen → Unbranched Glycogen Debranching Enzymes ● Glycogen accumulates in Lysosomes → Organ failure

2 Unbranched Glycogen → Glucose-1-Phosphate Phosphorylase III Cori Debranching Enzyme

3 Glucose-1-Phosphate ⇋ Glucose-6-Phosphate Phosphoglucomutase IV Andersen Branching Enzyme

4 Glucose-6-Phosphate → Glucose Glucose-6-Phosphatase V Mc Ardle Muscle Phosphorylase

VI Her Liver Phosphorylase

VII Tarui Muscle PFK

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 Lipid Metabolism Sphingolipids
Classification of Lipids Sphingomyelin
Fatty Acid
● Component of Myelin Sheath
Saturated
○ M.S. is for covering and insulation

Fatty Acid # of Carbon Atoms Fatty Acid # of Carbon Atoms

Capric 10 Palmitic 16

Lauric 12 Stearic 18

Myristic 14 Arachidic 20

Glycosphingolipids
Unsaturated ● Aka Glycolipids
● Component of neural tissues
Fatty Acid # of Carbon Atoms # of Double Bonds

Oleic 18 1 (#9) Cerebrosides Glucose or galactose

Linoleic 18 2 (#9, 12) (Omega-6) Globosides Glucose and galactose

Linolenic 18 3 (#9, 12, 15) (Omega-3) Gangliosides Oligosaccharide and sialic acid derivatives

Arachidonic 20 4 (#5, 8, 11, 14) (Omega-6)

Steroids
● Have CPPP nucleus
Glyceryl Esters
Fats Cholesteryl Esters
● Aka triglycerides, Triacylglycerols (TAGs) ● Cholesterol esterified with a fatty acids
● Esters of 1 glycerol and 3 fatty acids ● Transport form of a cholesterol in blood plasma and in cells
● Major form of Fatty Acids
● Functions Sterols
○ Protection of internal organs against
mechanical trauma ● Component of animal cell membrane
○ Insulators of body heat (maintain 37C) Cholesterol
● Controls membrane fluidity
○ Source of energy (temporarily stored in
ATP) Ergosterol ● Component of fungal cell membrane
Phosphoglycerides ● Component of plant cell membrane
Phytosterol (𝛃-Sitosterol)
● Example of glyceryl esters ● Most abundant
● Major component of biological membranes
Stigmasterol ● Found in soybeans and calabar bean
● Aka Glycerophospholipids

2 Types Bile Acids

1. Lecithin (Phosphatidylcholine) ● Cholic Acid - Emulsification of fats and cholesterol (from food) for absorption
2. Cephalin (Phosphatidylethanolamine) ○ Derived from cholesterol

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 Steroid Hormones
K Menadione ● Formation of Clotting Factors (II, VII, IX, X)

Sex Hormones Corticosteroids

Estrogen, Progesterone, and Testosterone Aldosterone Metabolism of Fats

● Development of secondary female and ● Reabsorption of Na+ and Water in kidneys Lipoproteins
male sexual characteristics ● Since triglycerides and cholesterol esters (non-polar) are insoluble in plasma (aqueous), and,
Cortisone to be transported to tissues where they are needed, such as muscle and adipose tissue, they
● Natural and anti-inflammatory agent must get packaged as lipoprotein particles
● Cholesterol
○ Synthesized in the liver through the mevalonic acid pathway
Vitamin D ○ Functions
● Aka Sunshine Vitamin → Regulate membrane fluidity
● Synthesis and Activation → Precursor for other steroids

Lipoprotein Function

● Aka Ultra Low-Density Lipoproteins

Chylomicrons ● Transports dietary triglycerides and cholesterol from the
intestines

Very Low-Density ● Transports triglycerides from the liver to the peripheral tissues
Lipoprotein (VLDL)

● Aka Bad Cholesterol

○ Plaque - Atherosclerosis or loss of elasticity that is
Low-Density
irreversible
Lipoprotein (LDL)
→ Continuous deposit in blood vessels → hypertension
● Transports cholesterol from the liver to the peripheral tissues

● Aka Good Cholesterol

High-Density
● Transports cholesterol from the peripheral tissues (excess in
Lipoprotein (HDL)
artery) back to the liver for metabolism

Lipogenesis
Terpenes ● Excess glucose is converted to fatty acids
● Formation of fats
● Regulated by Insulin
Vitamin Other Name Function
○ Excess glucose is converted to fats (De Novo Lipogenesis)
● Retinal, its aldehyde form, is needed for the ○ Condensation and decarboxylation steps are repeated until Palmitoyl CoA is synthesized
formation of Rhodopsin, a visual pigment ○ Enzyme - Fatty Acid Synthase
A Retinol ○ Co-enzyme - NADPH (Produced in PPP)
● Hastens cell turnover
● Oxidation - Retinol → Retinal → Retinoic Acid

𝛂-Tocopherol ● Anti-oxidant of biological membranes by

E
● Most active tocopherol preventing lipid peroxidation

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 ● After Step 5:
Step Reaction Reaction Product ○ Carried by the blood to a metabolizing cell (muscle cell or myocyte)
○ In the cytosol
1 Glucose → Acetyl CoA → Glycerol → glyceraldehyde-3-phosphate → glucose (gluconeogenesis)
→ FA are activated → use 2 ATP each to form fatty acyl CoA → enter the mitochondrion
2 Acetyl CoA + COO- Carboxylation Malonyl CoA

3 Malonyl CoA + Acetyl CoA In the Mitochondrion

1. Fatty Acids are activated to Fatty Acyl coA
4 5C - COO- Decarboxylation Butyryl CoA 2. Fatty Acyl coA enters the matrix with the help of L-carnitine (carrier molecule to transfer
the activated FA to the inner membrane)
5 Butyryl CoA + Malonyl CoA
3. Fatty Acyl coA undergoes beta oxidation
6 7C - COO- Decarboxylation Caproyl CoA
Beta Oxidation
7 Caproyl CoA + Malonyl CoA ● 4 Steps
8 9C - COO- Decarboxylation Caprylyl CoA
1. Dehydrogenation/Oxidation (Product - FADH2)
2. Hydration
9 Caprylyl CoA + Malonyl CoA 3. Dehydrogenation/Oxidation (Product - NADH)
4. Cleavage
10 11C - COO- Decarboxylation Capryl CoA ● Example - Caproyl CoA (6C)
11 Capryl CoA + Malonyl CoA

12 13C - COO- Decarboxylation Lauroyl CoA

13 Lauroyl CoA + Malonyl CoA

14 15C - COO- Decarboxylation Myristoyl CoA

15 Myristoyl CoA + Malonyl CoA

Palmitoyl CoA
16 17C - COO- Decarboxylation ● Humans can synthesize
until this

Lipolysis
● Breakdown of fats into glycerol and 3 fatty acids
● Regulated by the hormones: Norepinephrine, Cortisone, Glucagon, Growth Hormone and
ACTH (Adrenocorticotropic Hormone)

In Adipocyte
1. Hormones bind to their respective receptors.
2. cAMP, a secondary messenger is synthesized
3. cAMP activates protein kinase
4. Protein kinase activates hormone-sensitive lipase
5. Lipase converts fats into glycerol and 3 Fatty Acids

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 ○ Computation Protein Metabolism
→ 5 Acetyl CoA x 10 ATP = 50 ATP Amino Acids
→ 2 FADH2 x 1.5 ATP = 6 ATP ● Building blocks or monomer units of proteins
→ 4 NADH x 2.5 ATP = 10 ATP ● General Formula
→ Total - 66 ATP
→ Minus 2 ATP (From activation of FA) → 64 ATP Nett
● More Example - Palmitic Acid (16/2 = 8 Acetyl CoA)

# Product ATPs

8 Acetyl CoA (x 10) 80 Classification of Amino Acids

Based on Side Chains
7 FADH2 (x 1.5) 10.5
Simple Amino Acids
7 NADH (x 2.5) 17.5 ● Aliphatic
Total 108 ● R Group - Hydrogen atom
● Simplest amino acid
-2 ● Only amino acid that is NOT optically active (No Chiral C)
○ Requirement - Chiral carbon/asymmetric carbon (4 different
Energy Yield 106
functional groups binded)
● Biologically important for the synthesis of creatine and purine
Lipid Storage Diseases ● Major inhibitory neurotransmitter in the spinal cord
● Converted to Heme - Non-protein portion of hemoglobin
Glycine (G, Gly)
Disease Enzyme Deficiency Lipid Accumulating

Hexosaminidase A
Tay-Sach’s Disease ● Breakdown of excess Gangliosides
● No treatment gangliosides in ● → organ failure
mesosomes

Fabry’s Disease 𝛂-galactosidase Globosides

Galactosylceramide or
Krabbe’s Disease 𝛃-galactosidase ● R Group - Methyl (CH3)
Galactocerebrosides Alanine (A, Ala)
● Next simplest amino acid
Glucosylceramide or
Gaucher’s Disease 𝛃-glucosidase
Glucocerebrosides Aromatic Amino Acids
Niemann-Pick Disease Sphingomyelinase Sphingomyelin ● Said to be hydrophobic with the exception of Tyrosine
● R Group - Methyl group substitution = Phenyl + alanine
Faber’s Disease Ceramidase Ceramide ● Converted to tyrosine (Enzyme - Phenylalanine)
● Phenylketonuria
Phenylalanine ○ Absence of phenylalanine hydroxylase (genetic disease)
(F, Phe) ○ Phe is converted to Phenylketones then excreted in the urine
(musty odor)
→ Phenylketones will reach the brain → slow down Krebs Cycle
in brain cells → mental retardation

14
 ● R Group - Phenol ring structure
○ Phenol - Benzene ring with OH group in para position Aspartic Acid ● Aka Aspartate
● Converted to Catecholamines - Epinephrine, Norepinephrine, (Asp, D)
Dopamine
● Converted to Melanin (Enzyme - Tyrosinase) ● Aka Glutamate
Glutamic Acid
Tyrosine (Y, Tyr) ○ Melanin - Protects the skin from harmful effects of ultraviolet light ● Converted to Gamma Amino Butyric Acid (GABA)
(Glu, E)
→ Brown pigment present in skin and hair ○ Major inhibitory neurotransmitter in the brain
○ Albinism - Absence of tyrosinase
● Converted to Thyroid Hormones (T3 and T4) Imino Acid
○ T3 - Triiodothyronine
○ T4 - Thyroxine
● No amino (NH2) group
● R Group - Indole
● Converted to 5-hydroxytryptamine or serotonin Proline (Pro, P)
● Converted to melatonin (regulates sleep-wake patterns)
Tryptophan
● Converted to Niacin (Vitamin B3)
(W, Trp)
○ Pellagra - Vitamin B3 deficiency (Diarrhea, dementia, dermatitis)
● Hartnup’s Disease - Inability to absorb
Amidic Amino Acids
○ Pellagra-like symptoms

Asparagine (Asn, N)
Sulfur-Containing Amino Acids
● With sulfur → polar amino acid cause S is electronegative Glutamine (Gln, Q)

● R Group - Thiol (SH) Branched-Chain Amino Acids

Cysteine
● Synthesis of Glutathione ● Substituent at the 𝛃-Carbon
(Cys, C)
○ 3 Amino Acids in Glutathione - Glutamic acid, cysteine, glycine

Methionine ● R Group - Thioether (RSR) Leucine (Leu, L)

(Met, M) ● Biologically important for homocysteine synthesis
Isoleucine (Ile, I)

Basic Amino Acids Valine (Val, V)

● Positively charged → polar
Alcoholic Amino Acids
Histidine (His, H) ● Converted to histamine
Serine (Ser, S)
Arginine (Arg, R) ● Converted to nitric oxide (natural vasodilator)
Threonine (Thr, T)
Lysine (Lys, K)

Acidic Amino Acids

● Negatively charged (polar)
● Have carboxyl functional group

15
 ○ Need vitamin B6 (Pyridoxine)
Based on Source

Essential Amino Acids (10) Non-Essential Amino Acids (10)

1. Phenylalanine 1. Glycine
2. Valine 2. Alanine
3. Threonine 3. Aspartic Acid
4. Tryptophan 4. Asparagine
5. Isoleucine 5. Glutamic Acid
6. Methionine 6. Glutamine
7. Histidine 7. Serine
8. Arginine - Conditionally essential 8. Proline
(Essential during stress and illness) 9. Cysteine
9. Lysine 10. Tyrosine
10. Leucine

Based on Metabolism

Ketogenic Amino Acids (2) Glucogenic Amino Acids (13) Both Ketogenic and
Glucogenic Amino Acids (5)

● Converted to ● Converted to pyruvate ● Converted to

acetoacetate (ketone and then to glucose acetoacetate, pyruvate
body) and then to acetyl ● Converted to Krebs Cycle and Krebs Cycle
coA intermediates intermediates

1. Leucine 1. Glycine 1. Phenylalanine

2. Lysine 2. Glutamic Acid 2. Isoleucine
3. Alanine 3. Tryptophan
4. Glutamine 4. Tyrosine Urea Cycle
5. Methionine 5. Threonine ● Aka Ornithine Cycle
6. Cysteine ● Removes ammonia from the blood and converts it to urea
7. Asparagine ○ Ammonia (NH3) - One of the products of the breakdown of proteins
8. Aspartic Acid → Toxic - Encephalopathy
9. Proline
10. Valine
11. Serine
12. Histidine
13. Arginine

Transamination
● Transfer of an amino group from one amino acid to another 𝛂-keto acid by Transaminase
(aminotransferase)
● Enzymes - Aspartate Aminotransferase (AST), Alanine Aminotransferase (ALT)
● Co-enzyme - Pyridoxal Phosphate (PLP)
16
 Chromoproteins ● Melanin - Brown pigment (skin, hair, and eyes)
(Color-producing) ● Hemoglobin - Red pigment (RBCs)

● Actin - Thin and moving filament

Contractile Proteins ○ Binds to myosin to initiate muscle contraction
● Myosin - Thick and stationary filament

● Immunoglobulins or Antibodies
○ IgG - Smallest (Monomer)
→ Can cross placenta → protect fetus from infection
→ Most abundant in serum
○ IgA - Abundant in secretion (tears, saliva, breastmilk) (Dimer)
Protective or
○ IgM - Largest (Pentamer)
Defensive Proteins
→ First to be produced
○ IgE - Allergic reaction mediator (Type I) (Monomer)
○ IgD - Non-specific function (Monomer)
● Fibrinogen - Converted to fibrin that binds together platelets and
other plasma proteins in a hemostatic plug
Peptide Bond Formation
● Dehydration reaction Enzymes
● Bond between NH2 group of one amino acid ● Catalyst/catalytic proteins
and carboxylic acid group of the next amino ● Properties
acid ○ Their action is dependent on temperature and pH
● NOT easily hydrolyzed (unlike esters) → Optimal Temperature - 37oC
● Electrically UNcharged (neutral) ⬩ Too High - Denaturation
● Peptide Bond - Bond between amino acids → pH Considerations
⬩ Pepsin - Active in acidic medium, like stomach (HCl)
⬩ Trypsin - Neutral (small intestine)
Classification of Proteins Based on Functions ○ Some enzymes are very specific
● Theories
○ Lock and Key Theory - The active site of an enzyme is complementary to the
● Collagen - Skin and cartilage conformation of the substrate
Structural ● Keratin - Hair and nails ○ Induced-Fit Theory - The substrate induces a conformational change to the enzyme
● Elastin - Dermis, arteries, tendons → Conformational Change - Conformation of active site changes to fit the enzyme
● HDL, LDL - Transports cholesterol
○ HDL - To the liver
○ LDL - Form the liver
Transport ● Hemoglobin - Transports oxygen, found in RBC
● Myoglobin - Transport oxygen, found in muscle tissues
● Albumin - Transports neutral and acid drugs
● Alpha-1 Acid Protein - Transport basic drugs

● Casein - Major protein in milk

Nutrient/Storage
● Ovalbumin - Major protein in egg white

17
 Parts of an Enzyme Triose Phosphate
● Apoenzyme - Protein portion Intramolecular Group Isomerase
● Co-Factor - Non-Protein portion Transfer ● Interconversion of
○ Prosthetic Group - Inorganic elements 5 Isomerases ● Transfer of glyceraldehyde-3-p
→ Tightly bound to the apoenzyme functional groups hosphate to
→ Example - Copper in cytochrome within the molecule dihydroxyacetone
○ Coenzymes - Derived from vitamins phosphate
→ Examples
⬩ NAD - B3 Citrate Synthase
⬩ FAD - B2 ● Joins acetyl CoA
⬩ PLP - B6 and oxaloacetate to
● Holoenzyme - Protein and non-protein portion Join functional groups synthesize citrate
○ Catalytically active 6 Ligases by forming new covalent
● Zymogen or Proenzyme - Inactive form of an bonds Pyruvate Carboxylase
enzyme ● Carboxylation of
○ Examples Pyruvate to form
→ Pepsinogen - Pepsin (HCl) oxaloacetate
→ Trypsinogen - trypsin (Enterokinase) 7 Translocase
6 Major Groups on Enzymes
Nucleic Acids
Enzyme Group Function Example
Commission #
Deoxyribonucleic Acid (DNA) Ribonucleic Acid (RNA)
NADH Dehydrogenase
● Remove electrons
1 Oxidoreductases Redox Reactions
and hydrogen from
NADH Pentose Sugar

Intermolecular group Hexokinase

transfer ● Transfer a
● Transfer of phosphate or
2 Transferases
functional groups phosphoryl group
from one molecule from ATP to
to another Glucose
Number of
Hydrolytic reactions
RNAse A Strands
● Transfer if
3 Hydrolases ● Cleaves PDE bonds
functional groups to
in RNA
water

Fumarase
Non-hydrolytic Bond
4 Lyases ● Interconversion of
Cleavage
fumarate to malate

18
 A-DNA mRNA Nucleoside vs Nucleotide
● Right-handed ● Carries genetic code or
information from the DNA Nucleoside Nucleotide
B-DNA template
● Right-handed ○ Ribosome for protein Base + Sugar Base + Sugar + Phosphate
● Most abundant form synthesis
1. Guanine + Ribose = Guanosine 1. Guanosine Monophosphate
2. Adenine + RIbose = Adenosine 2. Adenosine Monophosphate
Z-DNA tRNA
3. Cytosine + Ribose = Cytidine 3. Cytidine Monophosphate
● Least abundant form ● Folded structure (looks like a
4. Uracil + Ribose = Uridine 4. Uridine Monophosphate
Types ● Left-handed cloverleaf)
5. Thymine + Deoxyribose = 5. Thymidine Monophosphate
● Temporary carriers of amino
Deoxythymidine
acids, bringing the appropriate
amino acids to the ribosome
based on the messenger RNA
(mRNA) nucleotide sequence

rRNA
● Structural components of
ribosomes

Purines Purines
● Guanine ● Guanine The DNA Double Helix
● Adenine ● Adenine
● Elucidated by by James Watson and Francis Crick based on X-ray
Pyrimidines Pyrimidines
Discovery crystallography image of the DNA by Rosalind Franklin and Maurice
● Cytosine ● Cytosine
Wilkins
● Thymine ● Uracil
● Amount of adenine (A) is usually similar to the amount of thymine
Nucleobases (T)
(N-Bases) ● Amount of guanine (G) usually approximates the amount of
cytosine (C)
● The total amount of purines (A + G) and the total amount of
pyrimidines (C + T) are usually nearly equal.

Chargaff’s Rule

19
 Central Dogma of Molecular Biology

Complementarity of
Bases

Replication
● DNA-directed DNA synthesis
● Site - Nucleus

Important Enzymes

Helicase ● Opens or unwinds the DNA double helix

(Unzipping Enzyme)

● Anneals a primer
Primase
○ Primer - Short chain of nucleotides

● Adds complementary nucleotides to the elongating DNA strand

DNA Polymerase
○ Can only add to the 3’ end

DNA Ligase ● Joins discontinuous strands

Anti-parallelism ● Removes or tangles/supercoils in the DNA

Topoisomerase
● Topoisomerase I and Topoisomerase II

Steps of Replication
1. Helicase unwinds the double helix. Each of the strands will be replicated to form new
DNA strands.
2. Primase will attach a primer, which is complementary to the nucleotides present in
the original DNA strand (3’ – 5’)
● Primer will be 5’ – 3’
● Direction of reading stars from the right to the left
3. DNA Polymerase will add complementary nucleotides to the primer
● Can only add nucleotides at the 3’ end
● Complementary to original DNA strand
● Will produce the 1st copy of original DNA - Leading Strand (5’ – 3’)
4. For the 5’ – 3’ strand from the original DNA, the same process will occur
● Primer - 3’ – 5’
○ Problem - DNA Polymerase can only add enzymes to the 3’ end
○ Solution - Add more primers so that a 3’ end is exposed
● Add Okazaki Fragments (Short sequences of nucleotides) via DNA Polymerase
● 2nd copy of the original DNA will be called the Lagging Strand, to be joined by DNA ligase
20
 Transcription
● DNA-directed RNA synthesis
○ 2 Strands of DNA
→ Sense strand
→ Antisense Strand - Will be transcribed to form mRNA
● Key Enzyme - RNA polymerase
○ Adds complementary nucleotides
● Site - Nucleus

The Genetic Code

● Important Codons
○ Start - AUG (Met)
○ Stop - UAG, UGA, UAA

Steps of Transcription
1. RNA Polymerase binds to a specific part of the antisense strand
● Being adding complementary nucleotides to the strand
● Synthesize mRNA
2. mRNA undergoes post-transcriptional modifications
● mRNA - Intron and Exon
○ Intron - Not needed in translation → Removed by Heterogeneous Nuclear RNA (hnRNA)
● Once only exons are found on mRNA, it can proceed to the ribosomes for translation

Translation
● RNA-directed Protein synthesis
○ By mRNA
● Site - Ribosomes

● Codon - Has 3 nucleotides, is the basis for synthesis of a specific amino acid
● Anticodon - Complementary to codon

21
 Mutation VITAMINS
Point Mutation ● Biotin and Vitamin K may be obtained from the gut bacteria, while other vitamins are
● 2 Types of Point Mutation obtained from external sources

Fat Soluble (ADEK)

● Purine base replaces a purine base
● Pyrimidine base replaces a pyrimidine base
● Examples ● Aka Retinol
Transitional
Original Strand Mutated Strand ○ Oxidation of Retinol - Retinol (Alcohol) → Retinal (Aldehyde) → Retinoic
ACGGCG ATGGCG Acid (Carboxylic Acid)
GACCTA GGCCTA ● Importance
○ Retinal - For Rhodopsin to work (a visual pigment)
● Purine bases replaces a pyrimidine base and vice versa ○ Increase Cell Turnover - Removal of dead cells → promote growth of
● Examples new ones
Transversional Original Strand Mutated Strand Vitamin A ● Deficiency States
ACGGCG TCGGCG ○ Nyctalopia - Night blindness
GACCTA TACCTA ○ Xerophthalmia - Dryness of the eyes
● Precursor - Beta-carotene
● Results of Point Mutation ○ Yellow/orange fruits and vegetables
● Other Information
○ Most stable
● Codon containing the changed base codes for the SAME amino acid
Silent ○ Most teratogenic
● Example - UCA (Serine) → UCU (Serine)
● Aka Sunshine Vitamin - UV is needed for its synthesis and activation
● Codon containing the changed base codes for a DIFFERENT amino acid
Missense ● Precursors
● Example - UCA (Serine) → CCA (Proline)
○ Ergosterol - D2 Ergocalciferol
● Codon containing the changed base becomes a STOP codon ○ 7-Dehydrocholesterol - D3 Cholecalciferol
Nonsense Vitamin D ● Importance - Absorption of calcium ions from food
● Example - UCA (Serine) → UAA (Stop)
● Deficiency States
○ Rickets - Abnormal bone mineralization in children
Frameshift Mutation ○ Osteomalacia - Bone resorption in adults
● Insert or delete 1 or more nucleotides in the sequence → Nutrients fo to the blood → soft bones

● Aka 𝛂-Tocopherol - Most active tocopherol

● Examples
Original Strand Mutated Strand ● Importance - Antioxidant of biological membranes
Insertion Mutation Vitamin E
ACG GCG ACU CCA ACG AGC GAC UCC ○ Protect against effects of free radicals
Thr Ala Thr Pro Thr Ser Asp Ser ● Other Information - Synergistic with Se (Selenium)

● Examples ● Forms
Original Strand Mutated Strand ○ K1 - Phytonadione (Phylloquinone)
Deletion Mutation ○ K2 - Prenyl Menaquinone
ACG GCG ACU CC AACG _CGA CUC
Thr Ala Thr Pro Thr Arg Leu Vitamin K ○ K3 - Menadione
○ K4 - Menadiol
● Importance - Formation of Clotting Factors (II, VII, IX, X) - Important for
blood coagulation

22
 Water Soluble (BC)
● Most active cobalamin
● Importance
● Deficiency States Vitamin B12: ○ Maturation of RBCs
○ Beri-beri - Muscle weakness Cyanocobalamin ● Deficiency States
Vitamin B1: Thiamine
○ Wernicke-Korsakoff Syndrome - Neuropsychiatric disorder ○ Macrocytic Anemia
→ Due to chronic alcohol intake (excretes Vitamin B1) ○ Pernicious Anemia - Neurologic effects

● Importance - Formation of FAD ● Aka Antiscorbutic Vitamin, Cevitamic Acid

○ Deficiency - Metabolic disorders ● Importance
● Deficiency States ○ Anti-oxidant
Vitamin B2: Riboflavin ○ Cheilosis - Dryness and cracking of the corners of the Vitamin C ○ Formation of collagen
mouth ● Deficiency State - Scurvy (Muscle weakness, bleeding, inflamed
○ Glossitis - Inflammation of the tongue gums)
○ Stomatitis - Mouth sores ● Least stable vitamin (reducing agent = easily oxidized)

● Importance - Formation of NAD, NADP

○ Deficiency - Metabolic disorders
● Deficiency State - Pellagra
Vitamin B3: Niacin ○ Diarrhea
○ Dementia
○ Dermatitis
○ Left Untreated - Death

● Aka Chick Anti-dermatitis Factor

Vitamin B5:
● Importance - Formation of Coenzyme A
Pantothenic Acid
● Deficiency State - Burning foot syndrome (red, warmth, pain)

● Importance - Formation of Pyridoxal Phosphate (PLP) -

Vitamin B6: Pyridoxine Coenzyme in transamination reaction
● Deficiency State - Peripheral neuropathy

● Aka Vitamin H
Vitamin B7: Biotin ● Importance - Co-factor in carboxylation reactions (Pyruvate +
COO- → Oxaloacetate)

● Importance
○ Maturation of RBCs
○ Neural tube formation
● Deficiency States
Vitamin B9: Folic Acid ○ Megaloblastic Anemia (Macrocytic Anemia) - RBC are larger
than normal
○ Neural Tube Defects
→ Anencephaly - Skill is not fully developed
→ Spina Bifida - Lump in the spine

23
PHARMACOGNOSY Belladonna
Atropa belladonna
Solanaceae
● Atropine
Mydriatic
-
agent
MODULE 2 (Beautiful Lady) (Nightshade)
(Dilation)
● Knowledge of drugs from natural sources
○ Pharmakon - Drugs ● Ergotamine -
○ Gnosis - Knowledge Treatment of
migraine
Ergot (sclerotium) Claviceps purpurea Clavicipitaceae
● Ergonovine -
Plants Animals Microbes
Oxytocic agent
Digoxin (Leaves of Digitalis Cod Liver Oil (Gadus Griseofulvin (Penicillium (induce labor)
lanata) morrhua) griseofulvum)
Opium (Stone of Papaver somniferum ● Morphine -
● (+) inotropic agent (force) ● Source of vitamins A and ● Antifungal antibiotic
Immortality - (Exudate from unripe Papaveraceae Narcotic
● Increase the contractility D, and essential fatty (treatment of ringworm)
Paracelsus) capsule) analgesic
of the heart acids (Linoleic and
𝛂-Linolenic acid)
Claudius Galen
HISTORY OF PHARMACOGNOSY ● Father of Pharmaceutical Compounding
Babylonians ● Prepared formula of drugs containing plant and animal constituents (GALENICALS)
● Made clay models of human organs ○ Examples
● Evaluate the color, size, and condition of the liver to diagnose diseases → Toothache Drops
⬩ Clove Oil - Eugenol (Dental Analgesic)
Egyptians ⬩ Capsicum
● Adept in the process of Embalming ⬩ Camphor
● Used as an oleogum resin to mask the odor of dead bodies (Myrrh Astringent) → Cold Cream - Galen’s Cerate
● George Ebers - Archeologist who discovered the Paper Scroll (Now: Papyrus Ebers)
Germans
○ Contains medicines used by ancient Egyptians
C.A. Seydler
● Coined the term pharmacognosy from pharmakon and gnosis and used it in his dissertation,
Greeks
Analectica Pharmacognostica
Pedanius Dioscorides
● Wrote the book De Materia Medica Libri Clinique (The Medicinal Material in 5 Volumes)
J.A. Schmidt
● Wrote Lehrbuch Der Materia Medica where he used the term Pharmacognosy
Plant Scientific Name Family Name Uses
F.A. Fluckiger
● Treatment of
● Described the most comprehensive scope of pharmacognosy - “Simultaneous application of
burns
Aloe Aloe barbadensis Liliaceae various scientific disciplines with the object of acquiring drugs in every point of view”
● Emollient - Lock
moisture

● Colchicine -
Treatment of
Colchicum Colchicum autumnale Liliaceae ACUTE gout
○ Chronic Gout
- Allopurinol

24
Scope of Pharmacognosy
CRUDE DRUGS
● Sources of chemical constituents
Biologic Economic Biochemical
● Natural substances (parts of plants and animals)
● Carolus Linneus - Father ● Acacia gum (Suspending ● Constituents
of Taxonomy Agent) is imported from 1. Pharmacologically Crude Extract
○ Proposed the Sudan and Senegal Active - Have effect ● Mixture of constituents isolated from CRUDE DRUGS
binomial system of in body
naming (Genus a. Digoxin (+ Methods of Extraction
Name + Species inotropic Percolation
Name) agent) ● “To put through a sieve”
→ Oryza + sativa 2. Pharmaceutically ● The movement and filtering of fluids through porous materials
Active - Excipients ● Use a percolator with cotton, sand, and filter paper inside
a. Starch
(Tablet Solvent used in extraction
binder) ● Fats - Hexane
● Chlorophyll - Acetone
Menstruum
BIOGENESIS or DRUG BIOSYNTHESIS ● Resins - Ethanol
● Conversion of primary metabolites to secondary metabolites, used as drugs ● Solanine - Acetic acid
● Chrysarobin - Hot benzene
Primary Metabolite Pathway Secondary Metabolite Marc Undissolved portion that’s left in the percolator after extraction
Glucose Shikimic Acid (SA) Amygdalin and Prunasin Product of extraction
Extractive
● Constituents from crude drug + solvent (can be evaporated)
Fatty Acids Mevalonic Acid (MVA) Sterols, Terpenes

Amino Acids Shikimic Acid (SA) Atropine, Morphine Maceration

● Solid ingredients are placed in a stoppered container with the prescribed menstruum and
Affected by: allowed to stand for a period of at least 2-3 days in a warm place with frequent agitation, until
1. Ontogeny or the Stage of Development soluble matter is dissolved
● Young Leaves of Cannabis - Cannabidiol (Not a hallucinogen)
● Mature Leaves of Cannabis - Cannabidiol (THC - Tetrahydrocannabinol) Infusion
○ Marijuana - Cannabis sativa, C. indica, S. ruderalis ● Macerate solids for a period of time in either hot or cold water

2. Heredity or Genetic Composition Decoction

● Drugs are subjected to boiling in water for 5-10 minutes
Solanaceous Alkaloids
● Hyoscyamus niger, Solanaceae ● Cooling, straining and passing sufficient cold water through the drug
● Hyoscyamine
● Atropa belladonna, Solanaceae
● Atropine
● Datura stramonium , Solanaceae
● Scopolamine
3. Environment
● Senna - Must be placed in wetlands, otherwise it cannot produce Sennosides - Responsible
for its cathartic effect

25
 Preparation of Crude Drugs Microscopic Evaluation
● Use of microscope determine the
● To ensure the true natural source of the drug purity and identity of the drug
○ Examples ● Example - Rice starch has smaller
→ D. purpurea (Purple Flower) - Digitoxin granules than Potato starch
⬩ Lipid-soluble
⬩ Long T½ (Toxic)
→ D. lanata (White, Yellow, Brown Flower) - Digoxin
● Collection Time - To isolate the right type and right amount of
Collection
constituents
○ Example - Apples
→ Unripe Fruits - Protopectin (Not antidiarrheal) Pharmacologic Evaluation
→ Just Ripe Fruits - Soluble Pectin (Antidiarrheal) ● Used of live animals or excised organs of animals to evaluate the effect of drugs
→ Overripe Fruits - Pectic Acid (Oxidized) ● Aka Bioassay
→ Solanaceous Alkaloids (SHAt) are most abundant when the ● Animals Commonly Used:
fruits begin to form (get the leaves of the plant)

● Large scale collection Digoxin Pigeon

Harvesting ● Maybe mechanical or manual
Atropine Cat
● If the drug collected is potent → harvest manually
Oxytocin Chicken (Female domesticated)
● To ensure good keeping qualities
Drying ● Remove Water - Less prone to microbial attack, stop enzymatic Heparin Sheep (Blood)
degradation of constituents present in the plant
Cod Liver Oil Rachitic Rats
● Final step in the preparation of crude drugs
Garbling ● Remove - Other parts of the plant, dirt, adulterants Tubocurarine (Head Drop Assay) Rabbits
○ Lagundi - Only need leaves

● To prevent insect attack Physical Evaluation

Packaging, ● Applies physical constants to the active constituents of drugs
○ Expose to 65oC (simplest method)
Storage, and ● Example - Optical Rotation (Use Polarimeter)
○ Fumigate with methyl bromide
Preservation ○ Natural Camphor - +41 → +43 (Dextrorotatory
○ Add a drop to chloroform of CCl4
○ Synthetic Camphor - 0 (Racemic Mixture - Equal D and L)

Evaluation of Crude Drugs CLASSIFICATION OF DRUGS

● Quality - Intrinsic value of the drug Morphology
● Purity - Absence of adulterants ● Based on form or plant part where the constituents are isolated

Organoleptic Evaluation
Leaves Sennosides, Digoxin, Atropine
● Use of sense, the macroscopic appearance of the drug its odor and taste, the sound or
“snap” of the fracture, and the feel of the drug to the touch. Bark Cascarosides, Frangulin, paclitaxel
● Aka Macroscopic Evaluation
● Example Seeds Fixed oils
○ Lemon Oil - Terebinthinate Odor → Must not be dispensed
→ Oil has decomposed
→ Adulterated with turpentine oil
26
 Taxonomy Classification of Carbohydrates
● Based on phylogeny
○ Phylogeny - Natural relationship among plants and animals ● Sweet taste, soluble in water
1. Monosaccharides - 1 sugar unit (simple sugars)
Sugars
Old Family Name New Family Name 2. Disaccharides - 2 sugar units
3. Oligosaccharides - 3-10 sugar units
Grass Family Gramineae Poaceae
● Complex sugars
Mustard Family Cruciferae Brassicaceae ● Bland taste, insoluble in water
1. Homoglycans - Yield only 1 type of sugar upon hydrolysis
Mint Family Labiatae Lamiaceae
Polysaccharides (Starch → Glucose)
Carrot Family Umbelliferae Apiaceae 2. Heteroglycans - Yield different types of sugar units upon
hydrolysis [Hydrolysis of Carrageenan (Gum) → Glu, Fru, Gal,
Arabinose]
Pharmacologic
● Based on drug action
Monosaccharides
● Simple sugars
Cascarosides, Lactulose, Castor Oil Cathartic

Hammamelitannin, Myrrh Astringent ● Glucose - Aldohexose

● Erythrose - Aldotetrose
● Xylose - Aldopentose
Chemical
● Based on chemical type of constituents Aldose
○ Best method

Amygdalin, Salicin, Arbutin Glycosides

Morphine, Atropine, Caffeine Alkaloids ● Fructose (Levulose) - Ketohexose

● Erythrulose - Ketotetrose
Artemisinin, Taxanes, Camphor Terpenes ● Xylulose - Ketopentose
Ketose
CARBOHYDRATES
● Aldehyde or ketone alcohols that contain C, H,
and O
● Polyhydroxy Aldehydes or Polyhydroxy Ketones Classification Based on the Number of Carbon Atoms
● H and O have the same ratio as water, thus they
are Hydrates of Carbon
○ General Formula - CnH2nOn # of C Name Example
○ Hydrated of Carbon - Cn(H2O)n
2 Diose Hydroxyacetaldehyde
● First product of Photosynthesis - Plants need
CO2 and water to produce glucose and oxygen 3 Triose Dihydroxyacetone and Glyceraldehyde
𝐶𝑂2 + 𝐻2𝑂 𝑐ℎ𝑙𝑜𝑟𝑜𝑝ℎ𝑦𝑙𝑙
> 𝐶6𝐻12𝑂6 + 𝑂2
4 Tetrose Erythrose, Erythrulose
○ Chlorophyll - Green pigment found in plants
→ Trap ultraviolet light from the sun 5 Pentose Xylose, Arabinose, Ribose, Deoxyribose

27
 6 Hexose Glucose, Fructose, Galactose, Mannose Products of Carbohydrate Metabolism
Products of Oxidation
7 Heptose Sedoheptulose

8 Octose D-glycero-D-mannoctulose (Avocado Pulp)

Malic Acid From cherry juice (Prunus cerasus)
9 Nonose Sialic Acid
Citric Acid Isolated by Scheele from lemon juice
Hexoses ● Acidulant of effervescent formulations
● Most important monosaccharides
Tartaric Acid Product of wine industry
● Acidulant of effervescent formulations
● An Aldohexose
● Also known as Lactic Acid Acidulant in infant feeding formulas
○ Dextrose - Dextrorotatory Glucose
○ Blood Sugar Reduction
Glucose ○ Grape Sugar - Vitis vinifera
○ Physiologic Sugar - Converted to ATP (Energy), fuel for physiologic
activities ● From Mountain Ash (Sorbus
● Uses - Nutrient and sweetening agent aucuparia)
○ Nutrient 5% Dextrose in Water (D5W) ● Aka D-Glucitol - Product of
Sorbitol reduction of D-Glucose
● An Ketohexose ● Humectant, ingredient of toothpaste
Fructose ● Sweetest naturally-occuring sugar and chewing gums
(Levulose) ○ Can be isolated from sweet fruits, honey ● Taste half as sweet as table sugar
● Uses - Food for diabetes nutrient (Fructose injection), sweetening agent
● From Mountain Ash (Sorbus
● An Aldohexose aucuparia)
● Rapidly absorbed in the small intestines ● Aka D-Glucitol - Product of
Galactose ● C4 Epimers - Different arrangement of H and oH in Carbon 4 Sorbitol reduction of D-Glucose
D-Glucose D-Galactose ● Humectant, ingredient of toothpaste
H-C-OH HO-C-H and chewing gums
● Taste half as sweet as table sugar
● An Aldohexose
Mannose
● Readily forms insoluble osazone crystals
Disaccharides

Pentoses

● Aka Wood Sugar

● Boil corn sobs and straw with dilute acids of isolate xylan polymer
Xylose
● Uses - Diagnostic aid for intestinal malabsorption
○ Must be completely absorbed
● Formed by Dehydration Reaction
● Sugar in RNA ○ Remove a water molecule → glycosidic bond is formed between 2 sugars
Ribose
● DNA - 2-Deoxyribose ● Haworth - Structure of glucose (Cyclic)
● Fischer Structure - Linear

28
 Sucrose Isolation of Lactose
1. Let it stand for a period of time, fat globules will rise on top, forming a layer called as
● Aka Table Sugar
● Sources “cream”. The cream is churned to form “butter”.
○ Sugar Cane (Stem) - Saccharum officinarum a. Cream - Fat globules
○ Sugar Beets (Roots) - Beta vulgaris b. Buttermilk - Supernatant liquid
○ Sugar Maple (Fruits) - Acer saccharum 2. Need to remove the cream layer, which will be used to make butter. Now called
● Uses of Sucrose “Skimmed Milk”, it will not be treated with the enzyme bRennin → Separate into
○ Demulcent - Soothe inflammation layers.
○ Sweetening agent 1 Fructose + 1 Glucose a. Skimmed Milk - Milk left after separation of cream
○ Manufacture of Syrups - Simple Syrup, NF (Alpha-1,2 Glycosidic Bond)
(85% Sucrose → 85g Sucrose + 100 mL H2O) b. Rennin - Milk coagulating or curdling enzyme from the stomach of young
mammals
Maltose
c. Coagulum - Upper layer
● Aka Malt Sugar d. Whey - Part of milk where lactose is isolated
● Barley - Hordeum vulgare
● Common Ingredient of Energy Drinks Oligosaccharides
○ Hydrolysis - Maltase

Gentianose Glu - Glu - Fru

1 Glucose + 1 Glucose Raffinose Gal - Glu - Fru

(Alpha-1,4 Glycosidic Bond)
Maltotriose Glu - Glu - Glu
Lactose
Melezitose Glu - Fru - Glu
● Aka Milk Sugar
● From cow’s milk, Bos taurus
● Uses of Lactose Chemical Test for Sugars
○ Tablet diluent
○ Infant feeding formula (substrate or food for Reagents Positive Result Test
Lactobacilli)
● Lactase - Hydrolytic enzyme 1 Galactose + 1 Glucose Molisch Test Purple ring at the
General test for
● Aka Purple Ring Alpha Naphthol + HCl junction between 2
(Beta-1,4 Glycosidic Bond) carbohydrates
Test liquids
Lactulose
● Glu, Fru, Man -
● Semisynthetic Sugar - Produced by the alkali Needle-shaped
rearrangement of lactose ● Galactose -
● Brand Names - LiLac, Duphalac, Movelax Phenylhydrazine + Sugar Rhombic plates
Osazone Crystals
● Uses (MS, DS) ● Lactose - Powder
puff/hedgehog
○ Cathartic - Converted to lactic acid and acetic acid
1 Galactose + 1 Fructose ● Maltose - Sunflower
that cause irritation of the colon
or /Maltsazone
→ Increase osmotic pressure into the colon →
draw water → laxative effect Resorcinol and HCl
Seliwanoff’s Test Cherry red color Ketose
○ Prevent Portal Systemic Encephalopathy (for (Dehydrating Agent)
patients with Liver Failure)
Cupric Sulfate, Rochelle
→ Caused by Ammonia Accumulation Fehling’s Test Brick Red Precipitate
Salt (Sequestrant) Reducing Sugars

29
 ● Principle - ● All MS and DS Cassava Manihot esculenta Euphorbiaceae
Reduction of Cupric (except sucrose) are
Cupric Sulfate, Sodium
Benedict’s Test ions reducing sugars
Carbonate (Sequestrant)
Cupric (Cu2+, blue) → Constituents
Cuprous (Cu+, red))

Reducing sugars
Tollens Silver Mirror Ammoniated Silver
Silver Mirror (With aldehyde
Test Nitrate
functional group)

Reducing sugars
● Reducing MS - Ppt
Barfoed’s Test Cupric Acetate Red < 2 min
● Reducing DS - > 2
min

Tollens Phloroglucinol Amylose Amylopectin

Phloroglucinol
Test

Bial’s Orcinol test Orcinol

Pentoses ● Composed of 250-300 ● Composed of 1000 or
● Glu units linked by more Glu units linked by
Tauber’s Benzidine Test Benzidine 𝛂-1,4-glycosidic bonds 𝛂-1,4-glycosidic bonds
Chemical Composition ● Aka Linear Starch and 𝛂-1,6-glycosidic
Glacial Acetic Acid, bonds at every 25
Keller-Killiani Test 2-deoxy Sugars
Ferric Chloride
Glucose units
● Aka Branched Starch
Polysaccharides
Water Solubility Water soluble Water insoluble

Homoglycans Heteroglycans Iodine Test Deep blue Purple or violet

● Polysaccharides that yield SAME or ONE ● Polysaccharides that yield DIFFERENT or Percentage (in Starch) 25 75
type of sugar unit upon hydrolysis SEVERAL types of sugar unit upon
● Glucosans - Starch, Cellulose, Dextran hydrolysis
Uses of Starch
● Fructosan - Inulin ● Gums and Mucilages
1. Tablet Filler, Binder, and Disintegrant
● Glycosides
2. Antidote for Iodine Poisoning (Starch Slurry) or Suspension
● Principle - Formation of Starch-Iodo Complex, which is insoluble in body fluids → excreted
Homoglycans
Starch
Enzymes
Sources

● Breaks down starch to glucose units

Plant Scientific Name Family Name
Alpha Amylase 1. Salivary amylase or ptyalin (mouth)
Corn Zea mays Poaceae 2. Pancreatic amylase or amylopsin (small intestines)

Rice Oryza sativa Poaceae Beta Amylase ● Breaks down starch to nearly pure maltose

Potato Solanum tuberosum Solanaceae

Wheat Triticum aestivum Poaceae

30
Starch Preparations Plant Exudates or Shrub/Tree Exudates

● Starch that is mechanically or chemically processed (+ H2O) to ● Gum Arabic - Gum was extensively used by arabic physicians
rupture all or part of granules ● Arabin
Pregelatinized Starch
● Gelatinous solution ● Incompatible with Alcohol - Especially if the alcohol concentration is
● Use - Tablet binder Acacia (Acacia >60%
senegal) ○ Alcohol, USP (NLT 95% Ethanol) is incompatible
Sodium Starch Glycolate ● Use - Disintegrant
1. Acacia Gum + Bi → Swelling component
Hetastarch ● Use - Plasma volume expander (6%)
2. Acacia Gum + Fe → Gelatinization

Inulin ● Constituents
Tragacanth
● Use - Diagnostic aid for renal dysfunction ○ Bassorin - Swelling component
(Astragalus
● From ○ Tragacanth - Non-swelling
gummifer)
○ Blue Dandelion or Chicory - Cichorium intybus ● Most resistant to hydrolysis (→ more stable)
○ Cone Flower - Echinacea purpurea
● Aka Sterculia Gum
→ Flowers - Treatment of flu and common colds
Karaya (Sterculia ○ Sterculia - Has fetid odor
● Broken down into fructose → is a fructosan
urens) → Sterculius - Deity that presides over manuring
● Movicol - Karaya (Laxative) + Frangulin (Frangula, Cathartic)
Dextran
● Produced by a microbe Leuconostoc mesenteroides - Produced the enzyme Dextran
Sucrase → Catalyze conversion of sucrose to dextran Seed Gums
● Plasma Expander (6%) - Blood volume → Cardiac output → Lowered BP → Hypotension
Psyllium ● Use - Bulk laxative (Husk or Seed Coat)
Cellulose ● Plantago psyllium (Spanish)
● Hair of Cotton - Soft, fluffy staple fiber from Gossypium hirsutum, Malvaceae ● Plantago ovata (Blonde)
○ Chemical component of Cotton
● Use - Mechanical or topical protectant, used to prepared flexible collodion Cydonium (Cydonia vulgaris) ● Aka Quince Seed
● Preparations
○ Absorbent or Purified Cotton Guar (Cyamopsis tetragonolobus) ● Aka Guaran
○ Flexible Collodion
Locust Bean Gum (Ceratonia siliqua) ● Aka St. John’s Bread, Carob Pulp

Marine Gums

● Aka Japanese Isinglas

Agar ● Constituents - Agarose, Agaropectin
GUMS AND MUCILAGES ● Red Algae ● Uses
● Natural plant hydrocolloids (tablet binder, suspending agent, emulsifying agent, thickeners, ○ Gelidium cartilagenium ○ Solidifying agent in microbial culture media (petri
laxatives) ○ Gracilaria confervoides dish)
● Heteroglycans that yield fructose, glucose, mannose, xylose and various uronic acid ○ Laxative
derivatives
Algin/Sodium Alginate ● Algina - Antacid (Adjunct for treatment of PUD)
● Brown Seaweeds - ●
Macrocystis pyrifera

31
 Sources
● Forms
Carrageenan
○ Kappa - Gelling (Gelating Agent)
● Red Seaweed - Chondrus
○ Iota - Gelling (Gelating Agent) ● Aka Sacred Bark
crispus
○ Lambda - Non-Gelling (Thickener) ● Constituents
○ Cascarosides
● Resembles - Kappa Carrageenan Cascara Sagrada
Danish Agar → A and B - Isomers of Burbaloin
○ Can be used as gelatin agent Rhamnus purshianus
(Furcellaria fastigiata) → C and D - Isomers of Chrysarobin
● Aka Furcellarian (Friedrich Pursh)
○ Casanthranol - Purified mixture of anthranol glycosides from
Cascara Sagrada
Microbial Gum ● Use - Drastic cathartics

Frangula ● Aka Buckthorn Bark

● Has Pseudoplastic Property - Shear-thinning Rhamnus frangula ● Movicol - Karaya + Frangula
Xanthan Gum
● Added to toothpaste and ointments to hold shape and
(Xanthomonas campestris)
can spread easily ● 2 Types
1. Aloe barbadensis (Curacao Aloe)
2. Cape Aloe - Hybrid of Aloe spicata and Aloe ferox
Plant Extract Aloe
● Constituents - Aloe Emodin and Barbaloin
○ Have cathartic effects (taken internally)
● Isolated from the inner rind of Citrus Fruits and Apple Pomace ● Uses - Gel is used as treatment of burns, emollient
● Use - Antidiarrheal agent
● Collection Time ● 2 Types
Pectin 1. Cassia acutifolia (Alexandria Senna)
○ Unripe - Protopectin
○ Just Ripe - Soluble pectin Senna 2. Cassia angustifolia (Tinnevelly Senna)
○ Overripe - Pectic acid ● Constituents - Sennosides
● Must be planted in square lots of lands resembling rice paddies
GLYCOSIDES ● 2 Types
● Acetals in which the hydroxy group of 1. Rheum officinale (Chinese)
Senna
sugar is condensed with the hydroxy 2. Rheum emodi, Rheum webbianum (Indian, Himalayan)
group of non-sugar moeity ● Constituents - Rhein anthrones (Bark)
● Aka Sugar-Ethers - General formula is
● Constituent - Chrysarobin
ROR
Chrysarobin ● Very irritating
Andira araroba ● Use - Keratolytic agent
1. Sugar Portion - Glycine portion
● Solvent - Hot benzene
2. Non-sugar Portion - Aglycone/genin;
Basis of classification of glycosides
Saponin Glycosides
● Aglycone - Sapogenin
Anthraquinone Glycosides ○ Steroidal or Triterpenoidal
● Soap-like
● Aglycone Portion - Anthracene
● Identification Test - Modified Borntrager’s Test
● Screening test
● Use - Drastic cathartics (stimulate smooth muscles in the colon,
Froth Test ● Positive Result - Honeycomb froth that persists for more than 10
increasing peristalsis)
minutes
○ Except - Chrysarobin
→ Very irritating, used as a keratolytic agent

32
 ● Confirmatory Test
● Blood Agar Medium
● Saponin Glycosides are Beta Hemolytic
a. Alpha Hemolysis - Partial breakdown of RBC → Bilirubin →
Hemolysis Test Biliverdin (Green color)
b. Beta Hemolysis - Complete breakdown of RBC (Red → Clear)
c. Gamma hemolysis - No effect on RBC (Red → Red)
○ Toxic to RBC of fish and cold-blooded animals
→ Saponin Glycosides are fish poisons

Sources

● Plant Parts - Roots and rhizomes

● Constituents
○ Glycyrrhizin - 50x as sweet as sugar
○ Glycyrrhetic Acid - Steroid, anti-inflammatory
Glycyrrhiza or ● Uses
Licorice ○ Anti-inflammatory
(Glycyrrhiza glabra) ○ Treatment of Addison’s disease (severe glucocorticoid Amygdalin and Prunasin Laetrile or Vitamin B17
deficiency)
○ Mask the bitterness of Quinine ● Amygdalin → Prunasin → Hydrocyanic Acid ● Has anti-cancer claims
○ Added to rootbeer to impart a bitter after taste + Benzaldehyde ○ Cyanide is toxic to other cancer cells
○ Added to beer to increase its foaminess ● Enzymes - Collectively called Emulsin - ● Already banned
Are 𝛃-Glucosidases (Can only hydrolyze ○ Also kills normal cells
Dioscorea or Yam ● According to US DoA, D. floribunda is the best source of steroids 𝛃-Glyco/Glucosidases)
(Dioscorea ● Constituents - Diosgenin and Botogenin ○ Amygdalase
floribunda, D. ○ Prunase
spiculiflora)

1. Panax ginseng - Korean or Asian ginseng Sources

2. Panax quinquefolius - American ginseng
● Constituents - Panaxosides, Ginsenosides, Chikusetsusaponins Plant Scientific Name Family Name
Ginseng
● Uses
○ Adaptogen - Helps the body to ADAPT to stress Prunus amygdalus (seeds)
○ Aphrodisiac - Increase sexual drive ● Amara - Bitter
Almond ○ Contains cyanogenic glycosides
Cyanogenic/Cyanophoric Glycosides ○ Roast → not toxic anymore
● Dulcis - Sweet Rosaceae
● Cyanide-forming glucosides (toxic)
○ Cyanide - Inhibits Cytochrome Oxidase (important for ETC) Apricot Prunus armeniaca (seeds)
● Identification test - Guignard test
Wild Cherry Prunus serotina (stems, leaves, bark)

33
 Cardioactive Glycosides Converted to (Mustard Oils) Allyl isothiocyanate Acrinyl isothiocyanate
● Use - Positive inotropic agents → increase force of contraction of the heart
● Aglycones - Both have CPPP nucleus → cardioactive glycosides are steroidal in nature Enzyme Myrosin Myrosin
○ Cardenolide - Most common; plants
○ Bufadienolide - Skin of toads and bullfrogs
● Effects of Mustard Oils - Local irritant, emetic, rubefacient (redness of skin), vesicant (blister
Sources formation), and condiment

Flavonol Glycosides
Plant Scientific Name Constituent
● From Rutaceae or Citrus Family
Digitalis lanata Digoxin (Lanoxin®) ● Flavonoids - Aglycone portion of
Grecian Foxglove ● White/yellow/brown ● Used in pharmacy for heart non-sugar glycosides
flower failure ○ 15C atoms
○ Polyphenolic - Soluble in water
Digitoxin
● Lipid-soluble - Completely 1. Rutin and Hesperidin (VITAMIN P,
Digitalis purpurea
Foxglove absorbed after oral Permeability Factors)
● Purple flower
administration 2. Hesperetin and Naringen
● Long half-life

Lilly of the valley or Lactone Glycosides

Convallaria majalis Convallatoxin (Toxic)
Convallaria

Adonis or Pheasant’s Eye Aodnis vernalis Adonitoxin (Toxic) ● From Tonka Beans (Dipteryx odorata)
● Used in Rodenticides (like Racumin)
Black Hellebore Helleborus niger Hellebrin (Toxic) Coumarin ● Anticoagulant
● Chemically related to warfarin
Strophanthus Strophantus kombo Strophanthin and Ouabain (Toxic) ● Antidote - Vitamin K
Apocynum or Black Indian ● Aka Blistering Fly, Russian Fly, or Spanish Fly
Hemp Apocynum cannabinum Apocynin (Toxic → Cardiac arrest) ● From Cantharis vesicatoria
● Indian Hemp - Cannabis ● Constituents - Cantharidin
Cantharides
○ Priapism - Happens when Cantharidin is taken internally
Adelfa Nerium oleander Oleandrin (Toxic)
→ Uncontrollable penile erection
Squill Urgenia maritima Scillaren A (Toxic, bulb) → Used as aphrodisiac

Night Blooming Cereus Selenicereus grandiflorus Tyramine ● Photosensitizing furocoumarins

○ Carcinogen - No longer used
Psoralens
○ Increase sensitivity of melanocytes to UV → Produces
Isothiocyanate Glycosides (Methoxalen)
melatonin
● Sulfur-containing glycosides from plants of family Cruciferae (Brassicaceae) ● Treatment of Vitiligo - Melanocytes are insensitive to UV light

Black Mustard White Mustard

Scientific Name Brassica nigra Brassica alba

Constituent Sinigrin (Seeds) Sinalbin (Seeds)

34
 Others
● Phlobaphenes - Red insoluble
Alcohol Glycoside
compounds
● Salicin - Bark of Salix purpurea and S. fragilis
○ Aglycone - Salicyl alcohol ● FeCl3 T.S. - Bluish Black Precipitate ● FeCl3 T.S. - Greenish Black Precipitate
○ Use - Antirheumatic agent
● Bromine Water Test - No Precipitate ● Bromine Water Test - Precipitate

● Bloom Leather ● Tanner’s Red Leather

Aldehyde Glycoside
● Vanillin or Glucovanillin - Cured fruits of Vanilla planifolia ● Uses
○ Aglycone - Vanillin ○ Industrial - Manufacture of dyes, Leather
○ Use - Flavorant ○ Medicinal
○ IUPAC Name - 4-hydroxy-3-methoxybenzaldehyde → Astringent - To constrict pores of skin → Won’t release sebum/oil
→ Precipitate - Glycosides, alkaloids, proteins
⬩ In Universal Antidote, Tannic Acid is the precipitating agent
Phenol Glycoside
Sources
● Arbutin - Leaflets of Arctostaphylos uva ursi
○ Aglycone - Hydroquinone
● Aka Witch Hazel Leaves
○ Use - Astringent and depigmenting agent
Hamamelis ● Leaves of Hamamelis virginiana
○ Bearberry
● Constituent - Hamameli tannin (Astringent)

● Excrescence produced by Cynips tinctoria (insect) on Quercus infectoria

TANNINS Nutgall
(plant)
● Polyphenolic compounds that are difficult to separate because they do not crystallize

LIPIDS
Hydrolyzable Non-Hydrolyzable or Condensed
● Polyphenolic compounds that are difficult to separate because they do not crystallize
● Chemically related to Pyrogallol ● Chemically related to Catechol
Fats Fixed Oils Waxes

● Esters of glycerol and ● Esters of glycerol and ● Esters of high molecular

saturated fatty acids unsaturated FA weight alcohols and fatty
● Solid at room ● Liquid at room acids
temperature temperature ○ HMW Alcohol - Cetyl,
● From Animals ● From Plants Stearyl (18C) Alcohols
○ Lard - Sus scrofa
○ Tallow - Bos taurus

● Exceptions
○ Cod Liver Oil - Liquid animal fat
○ Theobroma Oil (Cacao Butter) - Solid vegetable oil
● Uses
○ Emollients - Sunflower oil
+ HCl → Phenolic Acids and Sugars + HCl → Polymerize, forming Phlobaphenes ○ Cathartics - Castor oil
● Phenolic Acids - Gallic acid/ellagic acid → Has Triricinolein, which can be converted in the colon to Ricinoleic Acid → Can
cause irritation of colon → Peristalsis
35
 ○ Solvents for IM Injection - Corn, Cottonseed, Peanut, Sesame Oil Fats
○ Soap Production
→ Saponification - Alkali-catalyzed esterification of fatty acids ● Aka Cocoa Butter
○ Nutrient ● From Theobroma cacao seeds
→ 1g Carbs = 4 kcal energy ● Use - Suppository base
→ 1g Protein = 4 kcal energy
● Forms and Melting Points
→ 1g Fat = 9 kcal energy Theobroma Oil
○ 𝛂 - 22
○ 𝛃 - 34.5 (most ideal)
Fixed Oils
○ 𝛃’ - 28
○ 𝛄 - 18
Plant Scientific Name Use
● From wool of sheep, Ovis aries
Cottonseed Oil Gossypium hirsutum ● Lanolin - Contains 25% water
● Test - Halphen test (Seeds) Lanolin
● Woolfat (Anhydrous Lanolin) - Contains 0.25% water
Solvent for IM Injection ● Use - Ointment base
Sesameseed Oil (Linga)
● Test - Baudouin test Sesamum indicum
● Aka Teel Oil or Benne Oil ● From Gadus morrhua
● Rich source of Vitamins A and D, and Essential Fatty Acids (LL)
Cod Liver Oil
Coconut Oil
Cocos nucifera Soap production
● Sodium Morrhuate (Salt Form) - Sclerosing agent for obliterating
● Contains Lauric Acid (50%) and Myristic Acid (20%) varicose veins
Castor Oil (Tandan-tangan)
● Contains Ricin (Toxic Lectin) and Triricinolein Ricinus communis Cathartic Waxes
(Ricinoleic Acid)

Peanut Oil ● Waxy substance isolated from the head of sperm whale, Physeter
Arachis hypogaea macrocephalus
● Aka Arachis oil
Solvent for IM injection
Spermaceti ● Synthetic Alternatives
Corn Oil Zea mays ○ Cetyl ether wax
Safflower Oil Carthamus tinctoria
○ Hydrogenated jojoba oil
Source of nutrient,
Emollient ● Wax, not fixed oil
Sunflower Oil Helianthus anuus
Jojoba Oil ● Seeds of Simmondsia chirensis
Diagnostic aid ● Use - Hydrogenated form used as a n alternative to spermaceti
Ethiodized Oil Injection
● Disorders of
● Iodine addition product of the ethyl ester derived Papaver somniferum
ovaries and ● From the honeycomb of Apis mellifera
from Poppy seed
uterus Beeswax ● Use - Stiffening agent
Olive Oil
● Constituent - Myricyl palmitate
● Only pericarp (exocarp, mesocarp, and endocarp)
● Leaves of Copernicia prunifera
oil Carnauba Wax
● Grades ● Use - Polishing agent (gel capsule)
Diagnostic aid
1. First Grade Virgin Olive oil
● Disorders of
2. Second Grade Virgin Olive Oil - Cold-pressed Papaver somniferum VOLATILE OILS
ovaries and
(extracted without heat)
uterus ● Aka essential oils or ethereal oils
3. Technical Grade - Use hot water in extraction
4. Sulfur Grade - Carbon disulfide ● Odoriferous principles released by plants
5. Tournant Oil - Fallen, decomposing olives; ● Produced as insect repellents or insect attractants
Cheapest

36
 Volatile Oil Fixed Oil Methods of Isolation

Made up of terpenes Esters of Glycerol and (Unsaturated) Fatty ● Not for heat-sensitive materials (use Expression Method)
Acids ● Fresh Sample - Steam distillation
○ Example - Peppermint oil, Spearmint oil
Cannot be saponified Can be saponified (alkali + fatty acid)
● Dried Sample - Water distillation
No permanent spot on grease test With permanent spot on grease test ○ Example - Turpentine oil (Pine trees)
Distillation
● Fresh or Dried Sample - Water and Steam Distillation
Distilled from natural sources Solvent extraction ○ Example - Clove Oil, Cinnamon Oil
● Empyreumatic Oils - Destructive Distillation (High temperature without
Decomposition - Oxidize and resinify (Darken) Decomposition - Rancidity air)
○ Example - Tar oil
● Medicinal Uses
○ Carminatives Enzymatic ● Example - Mustard oils are produced in the presence of Myrosin
○ Antiseptic Action
○ Antipruritic (Camphor)
● For heat-sensitive material
○ Counterirritants - Methyl Salicylate (Wintergreen Oil) Expression a. Ecuelle - For volatile oils from rind of citrus fruits
b. Enfleurage - For volatile oils from flower petals
Special Anatomical Structures in Plants

Chemistry of Volatile Oils

Labiatae (Lamiaceae)
● Terpenes are made up of Isoprene Units - Have double bonds, there is branching on 2nd
● Mint family Glandular hairs carbon (C5H8)
● Peppermint - Mentha piperita
Number of Isoprene Units General Formula
Piperaceae
Modified Parenchymal Cells Monoterpene 2 C10H16
● Pepper family
● Black Pepper - Piper nigrum
Sesquiterpene 3 C15H24
Umbelliferae (Apiaceae)
Diterpene 4 C20H32
● Carrot family Oil Tubes (Vitae)
● Fennel - Foeniculum vulgare Triterpene 6 C30H48
Rutaceae and Pinaceae Tetraterpene 8 C40H64
● Citrus and Pine family
Lysigenous and Schizogenous Passages
● Lemon - Citrus limon
● Pine - Pinus polustris Monoterpenes

● Synthesized by plants via the MVA Pathway

Hydrocarbon 1. Pinene from Turpentine Oil (Pine TRees - Pinus palustris)
2. Limonene from Lemon Oil (Lemon - Citrus limon)

● Synthesized via the MVA Pathway

1. Menthol
Alcohol a. Mentha piperita (Peppermint)
b. Mentha arvensis (Japanese Peppermint)
2. Linalool from Lavender oil (Lavandula angustifolia)

37
 Diterpenes
● Synthesized via the MVA Pathway (1) and Shikimic Acid Pathway (2)
Aldehyde 1. Citral from Lemon (Citrus limon)
2. Cinnamaldehyde from CInnamon Oil (CInnamomum cassia) Paclitaxel (Taxol), Cabazitaxel ● Use - Anti-cancer agent (brast, ovarian)
(Pacific Yew, bark of Taxus ● Taxanes - Paclitaxel, Docetaxel, Cabazitaxel
● Synthesized via the MVA Pathway brevifolia)
1. Carvone
a. (d/+) Caraway Oil - Carum carvi ● Constituents - Ginkgolides and Bilobalides
b. (l/-) Spearmint Oil - Mentha spicata Ginkgo ● Increase cerebral blood flow (memory enhancer)
Ketone
2. Camphor from Cinnamomum camphora (Ginkgo biloba) ● Adverse Drug Reaction - Bleeding by inhibiting PAF
a. Natural - Dextrorotatory (Platelet Aggregation Factor)
b. Synthetic - Racemic
3. Diosphenol from Buchu Oil (Barosma betulina)
Triterpenes
● Ar → SA
Phenol 1. Eugenol from Clove Oil (Eugenia caryophyllus) - Dental analgesic ● Uses
2. Thymol from Thyme Oil (Thymus vulgaris) - Antifungal Quassinoids
○ Mosquito repellant (anti-feedant)
(Neem Tree, Azadirachta indica)
○ Pediculides
● Ar → SA
1. Myristicin Oil/Myristica Oil from Nutmeg (Myristica fragrans)
Phenolic Ether Tetraterpenes
a. Use - Flavorant
b. Excess - Hallucinogen
1. Beta Carotene
● Synthesized via the MVA Pathway 2. Lycopene
Oxide 1. Eucalyptol or Cineole from Eucalyptus globulus leaves
2. Ascaridol (Chenopodium spp.) RESINS
● Complex substances (composed of resin acids, resin alcohols and resinotannols and
1. Methyl Salicylate (Aromatic) from Wintergreen Oil (Gaultheria resenes)
Ester procumbens) ● Amorphous - No definite form
2. Linalyl Acetate (MVA) from Lavender Oil (Lavandula angustifolia) ● Melts when heated
● Insoluble in water
Sesquiterpenes
Rosin or Colophony Pinus palustris Stiffening agent
● Aka GInseng of Europe
Chamomile Anti-mitotic
● Calming effect
(Matricaria chamomilla) Mayapple or Mandrake, ● Arrest cell division (Anti-cancer
● Carminative Podophyllum
Podophyllum peltatum agent)
● Aka Quinghaosu ○ Etoposide, teniposide
Artemisinin
● Common Name - Sweet wormwood
(Artemisia annua) Eriodictyon or Yerba Santa Eriodictyon californicum Disguise bitterness of Quinine
● New or novel antimalarial agent
Jalap Exogonium purga Cathartic
Velerian ● Sedative
(Veleriana officinalis) Mastic Pistacia lentiscus Dental varnish
Feverfew ● Parthenolides (Antipyretic) Kava or Kava-Kava Piper methysticum Muscle relaxants
(Tanacetum parthenium) ● Treatment of migraine
Cannabis sativa,
Hashish Contains THC (Hallucinogen)
Marijuana

38
 Oleoresins (Volatile Oils + Resins) Alkaloidal Base + H2SO4 Alkaloidal Salt
● Neutralization
Turpentine of Gum Turpentine ● Pinus palustris Atropine ● Add acid Atropine sulfate

● Capsicum frutescens ✗ (Sparingly soluble) Polar (Water, Alcohol) ✓

Capsicum or Cayenne Pepper
● Constituent - Capsaicin
✓ Non Polar (Ether, Benzene, ✗
White Pine ● Pinus strobus CCl4)

● Zingiber officinale
Ginger ○ Forms salts or precipitates with these reagents
● Constituent of Gingerol

● Copaifera spp. Mayer’s Reagent Mercury in Potassium Iodide

Balsam of Copaiba
● Not a true balsam
Wagner’s Reagent Iodine in Potassium Iodide
Oleogumresins (Volatile Oils + Gums + Resins)
Dragendorff’s Reagent Potassium Bismuth Iodide

● Commiphora molmol Valser’s Reagent Red Mercuric Iodide

Myrrh
● Medicinal Use - Astringent
Hager’s Reagent Picric Acid Solution
● Ferula asafetida
Asafetida (Devil’s Tongue)
● Medicinal Use - Carminative, Flavorant Pyridine-Piperidine Alkaloids

Balsams Alkaloids Source Use

● Cinnamic Acid and Benzoic Acid Derivatives → SA Pathway
Nicotine Tobacco, Nicotiana tabacum (Leaves) Smoking deterrent
Storax ● Liquidambar orientalis Taenicide
Betel Nut (Areca catechu)
Arecoline ● Kill tapeworms (taenia)
Peru ● Myroxylon pereirae (Jonathan Pereira) ● Tannin content causes esophageal cancer
● Anthelmintic
Tolu ● Myroxylon balsamum
Lobeline Indian Tobacco, Lobelia inflata Smoking deterrent
● Styrax benzoin
● Active ingredient in CBT (Compound Benzoin Tincture) Tropane Alkaloids
Benzoin
○ Other Ingredients - Ethanol, Aloe vera, Storax, Tolu ● Tropine ring
● Use - Wound antiseptic
Sources
ALKALOIDS
● Bitter, basic, nitrogenous substances that are physiologically active Belladonna Atropa belladonna, Solanaceae
● From the word ALKALINE that means Basic - Alkaloids are chemically AMINES
● Other Properties Hyoscyamus or Henbane Hyocyamus niger, Solanaceae
○ End with -ine
○ All are solids except Coniine, Nicotine, Sparteine, which are liquids Stramonium Datura stramonium, Solanaceae
○ Free alkaloids are sparingly soluble in water ● Jimson Weed, Jamestown Weed
●
European Mandrake Mandragora officinarum, Solanaceae

39
 Erythroxylum coca, Erythroxylaceae Morphine Codeine
Coca
● Source of Cocaine (local anesthetic, CNS stimulant)
● Most abundant ● Methylmorphine - Product of methylation of
● Most important morphine
Solanaceous Alkaloids ● Narcotic analgesic ● Most widely used
● Use - Antitussive

● Anti-cholinergic agent Heroin Noscapine

● Aka Racemic Hyoscyamine
● Uses ● Product of diacetylation of morphine ● Aka Narcotine
○ Mydriatic Agent - Dilation (Pupils) ● Aka Diacetyl Morphine ● No narcotic properties
Atropine ○ Antidote for Malathion and Parathion (Organophosphate) Poisoning ● Hallucinogen - Prohibited drug ● Use - Antitussive
○ Antidiarrheal
→ Lomotil® - Previously Diphenoxylate + Atropine, now Loperamide
○ + Inotropic agent Quinoline Alkaloids
○ Antisialagogue - Decrease salivary secretions
Alkaloid Sources Use
● Uses
Scopolamine or
○ Treatment of Motion Sickness - Transdermal
Hyoscine Quinine Bark of Cinchona succirubra (RED) Anti-malarial
○ Antispasmodic agent
Quinidine Bark of Cinchona calisaya (YELLOW) Anti-malarial, Anti-arrythmic
● Naturally a levorotatory
Hyoscyamine
● Use - Antispasmodic/spasmolytic agent
Imidazole Alkaloids
Isoquinoline Alkaloids
Alkaloid Sources Use
Source Scientific Name Alkaloid
Pilocarpine Leaves of Pilocarpus jaborandi Treatment of glaucoma
Ipecac Cephaelis ipecacuanha Emetine (Emetic)

Sanguinaria or Bloodroot Sanguinaria canadensis Sanguinarine (Emetic) Indole Alkaloids

Hydrastis (Goldenseal) Hydrastis canadensis Hydrastine (Antiseptic)

Alkaloid Source Scientific Name Description
Morphine (Narcotic Analgesic,
Opium (Exudate) Papaver somniferum Vinca Alkaloids
Severe pain)
● Vincristine Catharantus Catharanthus roseus ● Use - Anticancer
Tubocurarine (Non-depolarizing ● Vinblastine
Curare Strychnos castelnaui
Muscle Relaxant)
● Use - Hypotensive
agent
Opium Alkaloids Reserpine Rauvolfia Rauwolfia serpentina ● MOA - Depletes
reserves of
catecholamines

Physostigma or Calabar ● Use - Treatment of

Physostigmine Physostigma venenosum
Bean glaucoma

● Use - Treatment of
Ergotamine
migraine
Ergot Claviceps purpurea
● Air-dried milky exudate from Papaver somniferum ● Use - Oxytocic
Ergonovine
agent

40
 ● Causes tetanus-like ENZYME PREPARATIONS
Strychnine
effect (lock-jaw)
Nux Vomica Strychnos nux vomica
Enzyme Preparation Source Uses/Effects
Brucine ● Alcohol denaturant
Papain Latex of Carica papaya Skin lightening agent
Steroidal Alkaloids Protein digesting and milk coagulating
Bromelain Pineapple, Ananas comosus
enzyme
Alkaloid Source Scientific Name Use
Streptokinase Streptococcus (Group C, Beta Hemolytic) Thrombolytic (Dissolve clot)
Veratridine Green Hellebore Veratrum viride
Wound debridement
Cardiac Depressant
Veratridine White Hellebore Veratrum album Collagenase Clostridium histolyticum ● Remove dead tissues from
wound to promote wound healing
Hellebrin Black Hellebore Cardiac Stimulant
Sutilains Bacilllus subtilis Wound debridement

Alkaloidal Amines L-Asparaginase Escherichia coli Anti-tumor

Alkaloid Source Uses/Effects SAMPUNG HALAMANG GAMOT

Ephedrine or Ma
Ephedra sinica Potent vasoconstrictor Common name Scientific Name Use
Huang/Yellow Astringent

Seeds and corms of Colchicum Bayabas Psidium guajava Anti-septic

Colchicine Treatment of acute gout
autumnale
Akapulko (Ringworm Bush) Cassia alata Anti-fungal (RIngworm infection)
Mescaline Peyote Cactus, Lophophora williamsii Hallucinations
Allium sativum Antihypertensive, Treatment of
Bawang
Cathinone Khat or Abyssinian Tea, Catha edulis Amphetamine-like effects ● Contains allicin hypercholesterolemia

Yerba Buena Metha cordifolia (Mint) Analgesic

Purines or Methylxanthines
Pansit-pansitan or
Peperomia pellucida Treatment of gout
Ulasimang Bato
Alkaloid Source Uses/Effects
Ampalaya
Treatment of diabetes
Caffeine Seeds of coffea arabica ● Bitter melon cause of Momordica charantia
Mild CNS stimulant ● Due to charantin
(1,3,7- trimethylxanthine) Cotyledons of Cola nitida (Kola nuts) Momordicin

Theophylline Bronchodilator Niyog-niyogan Quisqualis indica Anthelmintic

Leaves of Camellia sinensis
(1,3-dimethylxanthine) ● Management of asthma
Tsaang Gubat Ehretia microphylla Antidiarrheal
Theobromine Was used as a diuretic, deplaces
Seeds of Theobroma cacao Blumea balsamifera
(3,7-dimethylxanthine) by safer ones Sambong Diuretic, dissolve kidney stones
● Or Carmona retusa

41
PHARMACOGNOSY: PLANT CHEMISTRY
MODULE 2
● Biogenesis - Conversion of primary metabolites to secondary metabolites which are used as
drugs.
○ Glucose → Amygdalin and Prunasin (SA Pathway)
○ Fatty Acids → Terpenoids (MVA and MEP Pathway)
○ Amino Acids → Atropine and Scopolamine (SA Pathway)

SHIKIMIC ACID PATHWAY

● 7-step metabolic pathway
● Occurs in bacteria, archaea, fungi, algae, some protozoans and plants
● Biosynthesis of folates and aromatic amino acids (Tryptophan, Phenylalanine and Tyrosine)
● Does not occur in animal cells
○ Essential for humans

Step Reaction Enzyme

1 Condensation DAHP Synthase

2 Cyclization 3-Dehydroquinate Synthase

3 Dehydration 3-Dehydroquinate Dehydratase

4 REDOX Shikimate Dehydrogenase

5 Phosphorylation Shikimate Kinase

6 Condensation EPSP Synthase

7 Elimination of Inorganic Phosphate (Pi) Chorismate Synthase

42
Products of the Shikimic Acid Pathway (And Their Secondary Metabolites)
PABA Phenylalanine Tyrosine Tryptophan

● Folates ● Cinnamic Acid ● Tocopherols ● Auxin

● Coumarins ● Tyramine ● Serotonin
● Condensed Tannins ● Cyanogenic ● Indole Alkaloids
● Salicylates Glycosides ○ Vincristine
● Stilbenes ○ Prunasine ○ Vinblastine
● Suberin ○ Amygdalin ○ Reserpine
● Anthocyanins ● Isoquinoline ○ Physostigmine
● Vanillin Alkaloids ○ Ergotamine
(Glucovanillin) ○ Sanguinarine ○ Ergonovine
● Phenylpropanoids ○ Emetine ○ Brucine
○ Methyl ○ Hydrastine ○ Strychnine
Salicylate ○ Morphine
○ Eugenol ○ Tubocurarine
○ Thymol
○ Myristicin
○ Trans-anethole
○ Cinnamaldehyde
● Tropane Alkaloids
○ Scopolamine
○ Atropine

SHIKIMIC ACID PATHWAY

● Occurs in plants, animals and fungi
● Site - Cytosol
● Products
○ Isoprenoids/Terpenoids
○ Steroids
○ Carotenoids

Step Reaction Enzyme

Acetyl CoA (2C) + Acetyl CoA (2C)

1 Condensation Acetoacetyl CoA Thiolase
= Acetoacetyl CoA (4C)

Acetoacetyl CoA (4C) + Acetyl CoA

2 Condensation HMG CoA Synthase
(2C) = HMG CoA (6C)

3 Reduction HMG CoA → Mevalonic Acid hMG CoA Reductase

Mevalonic Acid
4 Phosphorylation Phosphate/Mevalonate Mevalonate Kinase
5-Phosphate

5 Phosphorylation Mevalonate 5-Pyrophosphate Phosphomevalonate Kinase

6C - 1C = 5C → Isopentenyl
6 Decarboxylation Mevalonate Decarboxylase
Pyrophosphate

43
 Isopentenyl Pyrophosphate
7 Isomerization Dimethyl Allyl Pyrophosphate
Isomerase METHYLERYTHRITOL PHOSPHATE PATHWAY
● Aka Non-Mevalonate Pathway
● DMAPP (5C) + DMAPP (5C) = Geranyl Pyrophosphate (10C) ● Occurs in eubacteria, green algae and higher plants
8 Condensation ● Geranyl-PP (10C) + DMAPP (5C) = Farnesyl Pyrophosphate (15C)
● Site - Plastids
● Farnesyl-PP (15C) + Farnesyl-PP (15C) = Squalene (30C)
● Products - Same products MVA
○ Isopentenyl pyrophosphate
○ Dimethylallylpyrophosphate

1. In MEP Pathway, the precursor, 1-deoxy-D-xyluloss-5-phosphate is formed by the

condensation of pyruvate and glyceraldehyde-3-phosphate. [TRUE]
2. Subsequent steps in MEP Pathway including skeletal rearrangement, yield isopentenyl
pyrophosphate. [TRUE]
3. The MEP Pathway was identified in eubacteria, green algae, and higher plants. [TRUE]
4. Plants both have MEP and MVA. [TRUE]
5. The Shikimate pathway is both found in plants and animals. [FALSE: not animals]
6. The Shikimate pathway is a seven step metabolic pathway for the biosynthesis of folates
and aromatic amino acids[TRUE]
7. Products of the Shikimate pathway represents essential amino acids [FALSE: Tyrosine is
a conditionally essential amino acids; only when low phenylalanine in diet]
8. Lower forms of organisms like bacteria, fungi, algae, protozoans do not have shikimate
pathway [FALSE.]
9. MEP is a metabolic pathway for the biosynthesis of isoprenoid precursors, while MVA is
for the biosynthesis of phenylpropanoids [FALSE: SA]
10. MEP pathway occurs in plastids of plants while MVA occurs in the cytosol of plants
[TRUE]
11. MVA pathway stars with the condensation of two molecules of acetyl CoA to form
acetoacetyl coA, while MEP pathway starts with the condensation of pyruvate and
Steroids Carotenoids Isoprenoids (Terpenoids)
glyceraldehyde-3-phosphate [TRUE]
● Sterols - Cholesterol ● Lycopene ● Alcohols (Menthol, Linalool, 12. The end product of MEP is a geranyl pyrophosphate while the end product of MVA is
(Animals), Phytosterol ● Beta-carotene Terpineol) isopentenyl diphosphate. [FALSE: only intermediate products]
(Plants), Ergosterol (fungi) ● Lutein ● Aldehydes (Citral) 13. Which of the following consituents are produced by the Shikimate Pathway: Ergosterol,
● Bile Acid - Cholic Acid ● Ketones (Carvone, Camphor, Sitosterol, Morphine, Prunasin, Vanillin [Prunasin, morphine, vanillin]
● Steroid Hormones - Diosphenol) 14. Which of the following consituents are produced via Mevalonate Pathway: Terpineol,
Estrogen, Progesterone, ● Oxides (Eucalyptol, Camphor, Hyoscyamine, Squalene, Methyl salicylate [Terpineol, Camphor, Squalene]
Testosterone Ascaridol)
15. Determine the immediate precursor of phenylalanine
● Corticoids - Aldosterone, ● Hydrocarbons (Pinene,
Cortisone Limonene) a. Anthranilic acid
● Vitamin - Vitamin D b. Chorismic acid
● Squalene c. Phenylpyruvic acid
● Lanosterol d. Para-hydroxyphenylpyruvic acid
● Cholesterol - Most abundant
sterol in animals
● Ergosterol - Most abundant
sterol in fungi
● Phytosterol - Most abundant
sterol in plants
● Stigmasterol

44
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