PHARMACOGNOSY

Mocule 1t
 PHARMACOGNOSY
Pharmakon Gnosis

• Literal translation “Knowledge of Drugs”

• Study of DRUGS from NATURAL SOURCES
o Plants
§ Metformin
• isolated from the ___________of Galega officinalis, __________
(Common name: Goat’s Rue or _____________)
• Use: OHA (treatment of ________)
§ Morphine
• Isolated from Opium- air-dried, milky ___________ of the unripe
capsules of ______________ _______________, Papaveraceae
• Use: narcotic analgesic

o Animals
§ Porcine Insulin
• Pancreas of ___________ _____________, Suidae
§ Bovine Insulin
• Pancreas of ___________ _____________, Bovidae
Use: Treatment of DM ____
HUMAN INSULIN (Recombinant DNA technology)
• Eli Lilly
• Microbe: _________

o Microbes
§ Mevastatin
• Penicillium ___________, P. ______________
• 1st statin to be discovered (HMG coA reductase inhibitor)
§ Penicillin
• From Penicillium ___________, P. ________________
• Use: Antibacterial Antibiotic

Penicillin was accidentally discovered by Sir ____________________, but it was

successfully isolated by Florey and Chain using the technique, ___________________
or lyophilization.

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 HISTORY OF PHARMACOGNOSY:
1. BABYLONIANS
o made ___________models of the human body
o Babylonian Healers: examine the color, size and condition of the liver to
diagnose a disease
o aware of the medicinal effects of a number of plants

2. EGYPTIANS
o A document, known as the
_________________
was found in a tomb of a The Papyrus Ebers, previously the “Paper
mummy. It proved that Scroll” was discovered by an archaeologist.
Egyptians possessed an His name is________________.
understanding of the
human anatomy as well as a knowledge of
medicinal uses of many
plants.
In embalming, Egyptians used
o Adept in embalming the ______________, an oleo-gum-resin to mask
dead. the odor of the dead body

3. GREEKS
a. PEDANIOS DIOSCORIDES
• wrote the
book_________________________________________________________________________
(The Medicinal Material in 5 volumes)

NATURAL PRODUCTS
Aloe Extract from the leaves of Aloe __________________.
Uses: treatment of ________
Colchicum Seeds and corms of Autumn Crocus Colchicum ________________.
Use: treatment of ________(acute)
Belladonna Leaves of Atropa _______________.
Constituent: Atropine
Use:_____________, antidote for organophosphate insecticide poisoning
Ergot Dried sclerotium from Claviceps _____________.
Constituents:
Ergotamine- treatment of ____________

2
 Ergonovine- Oxytocic agent (induces __________)
Opium Stone of ______________(Paracelsus)
Air-dried milky exudate from Papaver _________________

Most important alkaloid:

MORPHINE (MORPHEUS: Greek god of DREAMS)
Use:

b. CLAUDIUS GALEN
• Father of Pharmaceutical COMPOUNDING
• Described the methods of preparing formulas containing plant and animal constituents
• Introduced Galenical Pharmacy
GALENICALS
• Example:
Cold Cream aka ____________Cerate
Rose Water (Tannins:___________ precipitants)
Lanolin (emollient)

4. GERMANS
Scientist Contributions
C. A. SEYDLER coined the term pharmacognosy from Pharmakon and Gnosis;
(Crr (Christian) Anotheus used it in his dissertation entitled Analectica Pharmacognostica
Seydler) (______)
J. A. SCHMIDT wrote_______________- first to use the term Pharmacognosy
(Johan Adam Schmidt)
F.A. FLUCKIGER described the most comprehensive idea of the____________of
(Friedrich August) pharmacognosy

“Simultaneous application of various scientific disciplines in

order to acquire drugs in every point of view”

Pharmacognosy is an applied science that deals with the

Biologic, Economic and Biochemical features of natural drugs
and their constituents
1. Biologic
Cascarosides
__________ __________ ___________ ___________
Plant part Genus Specie Name
Carolus Linnaeus
• Father of Modern Taxonomy
• Proposed the BINOMIAL System
• Genus specie

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 2. Economic
Acacia gum is exported by:___________ and ___________
Senna- must be planted in______lands resembling rice paddies

3. Biochemical
Active Constituents: responsible for the therapeutic effects
Inert Constituents: mainly used as excipients; may cause
incompatibilities

QUICK QUIZ
1. Dried sclerotium of Claviceps purpurea on rye
A. Opium
B. Alum
C. Ergot
D. Aloe
2. An agent that increases the force of contraction of the heart
A. (-) chronotropic agent
B. (+) inotropic agent
C. (+)chronotropic agent
D. (-) chronotropic agent
3. The simplest method to avoid insect attack
A. Fumigate with methyl bromide
B. Add a drop of chloroform
C. Add a drop of carbon tetrachloride
D. Expose the drug to 65 degree Celsius
4. It is the stone of immortality
A. Morphine
B. Opium
C. Ergot
D. Metamphetamine
5. Father of Pharmaceutical Compounding
A. Seydler
B. Fluckiger
C. Dioscorides
D. Galen

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 CRUDE DRUGS
Are vegetable or animal drugs that consist of natural substances that have undergone only the
processes of ______________and ________________.
Crude Derivatives or Extractives- principles separated from crude drugs.

PREPARATION of CRUDE DRUGS

1. Collection
o to ensure a TRUE and RELIABLE product
Digitalis lanata Digitalis purpurea
__________, ___________, __________flowers ____________flowers
DIGOXIN DIGITOXIN
• L
• L

Collection Time
1. Solanaceous Alkaloids (Atropine)
Must be collected when the fruits ____________________.
2. Pectin
Unripe Fruits:
Just ripe Fruits:
Overripe Fruits:

2. Harvesting
Manual Mechanical
• Aka Hand Labor • Less labor ______
• Needs skillful selection of plant
parts
• Employed when harvesting potent
drugs (Digoxin from Digitalis,
Atropine from Belladonna)

3. Drying
Reasons for drying:
o ensure good keeping qualities
o avoid molding, action of enzymes and
bacteria on the crude drug

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 4. Garbling
o FINAL STEP in the preparation of crude
drugs
o Removal of extraneous matter: other parts of the plant, ______, adulterants

5. Packaging, Storage and Preservation

Packaging
o Packaging must offer
ample protection against
heat and moisture
Storage and Preservation
o to prevent insect attack
a. Simplest: expose to ________
b. Fumigate with _________
c. Add a drop of _______and ________

METHODS OF EXTRACTION
Terms:
1. Menstruum- ______________used in extraction
Substance Menstruum
1. Fats
2. Resins
3. Chlorophyll
4. Solanine
5. Chrysarobin

2. Marc- undissolved portion

3. Extractive- product of extraction

Method Description
Percolation The process in which a comminuted drug is extracted of its soluble
constituents by the slow passage of suitable solvent through a column of
drug
Maceration solid ingredients are placed in a stoppered container with the prescribed
menstruum and allowed to stand for a period of at least __________ in a
warm place with frequent agitation, until soluble matter is dissolved
Infusion macerate solids for a period of time in either __________ or
_________water
Decoction drugs are subjected to boiling in water for __________; cooling, straining
and passing sufficient cold water through the drug

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 EVALUATION of CRUDE DRUGS

Quality Purity Identity

Intrinsic value of the Absence of adulterants Uniqueness
drug Example:
Example: Cottonseed Oil
Benedict’s Test:
______________

Method of Evaluation Description

Organoleptic Evaluation “Impression on the organs”
Aka Example:
________________Evaluation 1. color of the flowers
Digitalis lanata Digitalis purpurea

2. odor
Lemon oil with _______________odor should not be
dispensed.
3. Alkaloids- ______ taste

Microscopic Evaluation Use of ______________to determine the purity and identity of

the drug
Sample: ___________
Ex: Starches

Potato Starch Rice Starch

ü Simple granules
ü Hatchet, wedged or
mussel-shaped
ü Size ranges from __-
___ micrometers
ü Concentric striations,
well-marked
ü Compound granules
with angular outline.
ü Size ranges from __-
___ micrometers
ü Hilum located
centrally
ü No striations

FILTH- any rodent parts including hair, urine and ________.

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Pharmacologic Evaluation Aka ____________________
Assays on living animals or on excised or intact organs to
indicate the strength of the drug.
Drug Animal
Digoxin
Oxytocin
Heparin
Tubocurarine (Head Drop
Assay)

Chemical Evaluation BEST METHOD to determine official potency

Use of CHEMICALS or REAGENTS

1. Fehling’s
2. Benedict’s
3. Keller-Kiliani
4. Phloroglucinol
5. Osazone
Physical Evaluation use of Physical constants—Optical Rotation

____________-emits plane polarized light

CLOCKWISE:
COUNTERCLOCKWISE:
Racemic Mixture:

Natural Camphor Synthetic Camphor

+ 41à +43 ______________-not
______________ optically active

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 CLASSIFICATION of DRUGS
1. Morphologic
• based on plant part
Sennosides
Digoxin
Glycyrrhizin
Gingerol
Acacia gum
Tragacanth gum

2. Taxonomic
• based on phylogeny
Phylogeny- ___________relationship among plants and animals
Cucurbitaceae ___________Family
Alternate Leaves
Have _________
Fruits: __________
Examples:

Labiatae _______ceae
_______Family
square stems, opposite leaves, bilabiate flowers
Examples:
__________mint and __________mint
Solanaceae ____________Family
Alternate leaves
Cymose flowers
Fruits are berries or capsules
Examples:
Belladonna, ___________, Stramonium

3. Pharmacologic
• based on drug effects
Ex: Cascara Sagrada, Psyllium, Castor Oil are _____________.

4. Chemical
• Since the therapeutic use of drugs are based on chemical constituents,
CHEMICAL CLASSIFICATION is the preferred method of classification

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 QUICK QUIZ
1. Halphen test
A. Sesameseed oil
B. Cottonseed oil
C. Rapeseed oil
D. Almond oil
2. Animal employed for the assay of Tubocurarine, known as the head drop assay.
A. Cats
B. Rabbits
C. Pigeons
D. Sheep
3. Organoleptic Evaluation is also known as ___________.
A. Microscopic Evaluation
B. Chemical Evaluation
C. Physical Evaluation
D. Macroscopic Evaluation
4. Technical term for the solvent used in extraction
A. Marc
B. Menstruum
C. Crude Drug
D. Extractive
5. Lemon oil with a characteristic _________odor must not be dispensed.
A. Putrid
B. Aromatic
C. Terebinthinate
D. Acrid

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 CARBOHYDRATES
______________aldehydes or _____________ketones

Polyhyroxyaldehyde Polyhydroxyketone
Glucose Fructose

Classification of Carbohydrates
Monosaccharides aka Simple Sugars ____sugar unit
Disaccharides ____sugar units
Oligosaccharides ____sugar units
Polysaccharides ____sugar units

MONOSACCHARIDES aka SIMPLE SUGARS

# of C Name Example
2 Dioses Hydroxyacetaldehyde
3 Trioses Glyceraldehyde and Dihydroxyacetone
4 Erythrose, Erythrulose
5 Pentoses Arabinose, Xylose, Xylulose, Ribose, Ribulose
6 Hexoses
7 Heptoses Heptulose
8 Octoses D-glycero-D-Mannoctulose
9 Nonoses

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 HEXOSES
most important MONOSACCHARIDES
Glucose Blood Sugar, Grape Sugar and
(Dextrose) _______Sugar
Uses:
1. Source of ____________
2. Sweetening Agent
• Liquid Glucose
• Dextrose Excipient
Fructose Aka ________ Sugar
Isolated from sweet fruits, honey or mel
Uses:
1. Source of _____________(DM)
2. Sweetening agent

Galactose Reacts with HNO3 to form Mucic Acid Crystals

___Epimer of D- Glucose

Mannose ____Epimer of D- Glucose

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 Products of Oxidation
Glucoseà Plant Acids
1. Citric Acid-isolated by ____________
From Lemon Juice (Citrus limon,
_______________)
Use:___________in effervescent
formulations
2. Tartaric Acid- by product of
___________
Use:___________in effervescent
formulations
3. Lactic Acid- acidulant in
4. Fumaric Acid + Ferrous = Ferrous
Fumarate
Use:
5. Malic Acid- Flavorant
From Cherry Juice (Prunus __________,
Rosaceae)
Use:
Products of Reduction
1. Glucoseà_____________
Aka Sorbitol-
From berries of Mountain Ash (Sorbus
aucuparia, ________________)
H_____________, Half as sweet as sucrose
2. Mannoseà__________
From leaves of Manna Ash (Fraxinus
ornus, ________________)
Uses:
Osmotic ____________(_______ edema)
Osmotic ____________
Diluent in _______________ tablets

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 PENTOSES

Arabinose Xylose Xylulose Ribose and

Deoxyribose

Sugar in Gum ________Sugar

Arabic or isolated by boiling
____________ corn cobs and straw
with dilute acids
use:
___________________

Other Chemical Tests for Monosaccharides:

Bial’s Test Pentoses Orcinol + Pentoses= _________ color
Tauber’s Test Pentoses Benzidine + Pentoses= _____________color
Tollen’s Test Pentoses Phloroglucinol + Pentoses= _____________color

DISACCHARIDES
• Formed by dehydration reaction

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 Structure Bond

Disaccharide Sources and Uses

Sucrose Aka_____________
Sources:
a) Sugar Cane-Saccharum officinarum, _____________
b) Sugar Beets- B______ vulgaris, Amaranthaceae
c) Sugar Maple- A______ saccharum, Aceraceae
Uses:
a) Demulcent
b) Preservative
c) Sweetening agent
d) Manufacture of syrups

Maltose Aka ______________

Partial breakdown of starch
germination of Barley (Hordeum vulgare, ____________)
ingredient of energy drinks
Lactose Aka __________
Isolated from Cow’s milk _________

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 Steps:
1. Let cow’s milk stand for a while.
2. Fat globules rise on top:_______________.
3. Cream is churned to form _____________.
4. Leaving behind a supernatant liquid: ______________.

5. Separate the cream layer:______________.

6. Treat with RENNIN (milk coagulating enzyme from the stomach
of mammals)
7. Skimmed milk separates
8. Upper Layer: _____________--> Cheese
9. Lower Layer: _____________--> part of milk where Lactose is
isolated.

Uses of Lactose:
1. tablet diluent
(Chewable Tablet: ________________)
2. ingredient of infant’s milk
Food for Lactobacilli

Lactulose Semi-synthetic disaccharide (___________and ___________)

Produced by the _____________rearrangement of Lactose
Uses:
Cathartic
MOA: converted to _____________+____________ by microbes in
the colon leading to irritation

Prevent PSE (Portal Systemic Encephalopathy)

The acidified stool traps ammonia from the blood
Cellobiose and
Trehalose

____________+____________ ______________+____________
GB: GB

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 TESTS FOR REDUCING SUGARS
Fehling’s Test Cupric Sulfateà_________
Cu+2à_________
Blueà_________
Sequestrant: NaK Tartrate (Rochelle Salt)

Benedicts’s Test Cupric Sulfateà_________

Cu+2à_________
Blueà_________
Cupric Sulfate
Sequestrant: Na Carbonate
Tollen’s Silver Mirror Test Silver Nitrateà___________
Ag+1à__________
Colorlessà___________

Barfoed’s Test Cupric Acetateà__________

Cu+2à__________
Blueàred

Reducing Monosaccharides: _______

Reducing Disaccharides: _________

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 QUICK QUIZ
1. Milk left after the separation of cream
A. Buttermilk
B. Skimmed milk
C. Butter
D. Coagulum

2. Test for reducing sugars, except

A. Tollen’s Test
B. Phloroglucinol Test
C. Barfoed’s Test
D. Fehling’s Test

3. Semi-synthetic disaccharide formed by the alkaline rearrangement of lactose

A. Maltose
B. Trehalose
C. Cellobiose
D. Lactulose

4. Last chiral C in a linear structure

A. Penultimate C
B. Asymmetric C
C. Hydroxy Group
D. Anomeric C

5. Phloroglucinol test
A. Trioses
B. Hexoses
C. Pentoses
D. Nonoses

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 OLIGOSACCHARIDES:
3-10 Sugar Units

Gentianose Glu-

Raffinose Gal-

Maltotriose Glu-

Melezitose Glu-

Stachyose Gal-

POLYSACCHARIDES

Homoglycans Heteroglycans
Polysaccharides Polysaccharides

Same type of Sugar units Different types of Sugar Units

Starchà Glucose units Gums and Mucilages
Inulin à Fructose units
Example:
Carrageenan
1.
2.
3.
4.

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HOMOGLYCANS
1. STARCH
Zea mays, Poaceae Oryza sativa, Poaceae
Solanum tuberosum, Manihot esculenta,
__________________ ________________
Triticum aestivum, Poaceae

Composition
Amylose Amylopectin

Composed of ___________Glucose Composed of ___________Glucose units

units linked by __________glycosidic linked by __________glycosidic bonds and
bonds __________ glycosidic bonds at every 25
Glucose

Aka ________ starch or Aka ________ starch

_________starch
Water ___________ Water _________
Forms a ________ color with Iodine Forms a ________ color with Iodine TS
TS
25% (20-30%) 75% (70-80%)

Uses of Starch
Pharmaceutics Pharmacologic
1. Pregelatinized Starch 3. Hetastarch
chemically or mechanically processed to 6% _______________
rupture all or part of the granules
use: _____________ 4. Antidote for Iodine Poisoning

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 2. Sodium Starch Glycollate
use: ______________

2. INULIN
yields Fructose units only when hydrolyzed (FRUCTOSAN)
use: ___________________ for renal dysfunction

Chicory or Chicorium intybus, Asteraceae

___________ (root)
Cone Flower Echinaceae angustifolia, ______________

Traditional use:

3. DEXTRAN
Microbial product: Leuconostoc mesenteroides

Produces:
Dextran Sucrase or _____________
SUGARSà______________

Use:__% Plasma Expander

4. CELLULOSE
Cellulose Fibers:
Soft, fluffy staple fiber that grows around the seeds of Gossypium
hirsutum, Malvaceae
Pyroxylin or A flammable mixture of cellulose nitrates, usually with less than
Soluble 12.5% nitrogen, that is soluble in a mixture of ether and alcohol or
Guncotton other organic solvents

Cotton (cellulose)

Pyroxylin/ Soluble Guncotton

Collodion

Flexible Collodion
Use: ____________protectant

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 QUICK QUIZ
1. A polysaccharide that maintains the integrity of the plant cell wall
A. Cellulase
B. Cellulose
C. Amylopectin
D. Amylose

2. If starch is a glucosan, Inulin, which is converted to Fructose units only is a

___________.
A. Galactosan
B. Mannosan
C. Fructosan
D. Heteroglycan

3. An oligosaccharide containing 3 Glucose units

A. Maltotriose
B. Melezitose
C. Stachyose
D. Maltose

4. Soluble Starch
A. Amylopectin
B. Dextrin
C. Amylose
D. Inulin

5. Starch which is chemically or mechanically processed to rupture all or part of the

granules.
A. Hetastarch
B. Iodine Tincture
C. Pregelatinized Starch
D. Sodium starch glycollate

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 HETEROGLYCANS
Gums and Mucilages
-natural plant ______________that may be classified as anionic or non-ionic polysaccharides
-translucent, amorphous substances that are produced by plants as a protective after injury
-upon hydrolysis, they yield arabinose, galactose, glucose, mannose, xylose and various uronic
acid derivatives

Pharmaceutic Uses Pharmacologic Uses

Binders, emulsifiers, gelating agents, Bulk laxative
suspending agents, stabilizers, thickeners Demulcent
and adhesives Emollient

CLASSIFICATIONS:
A. Plant (Shrub or Tree) Exudates
Acacia _________ ________, Principal constituent: __________ (complex
Aka _________ Fabaceae mixture of Ca, Mg and K salts of Arabic Acid
Remains in solution at alcohol concentration
below _____%
Tragacanth Astragalus Contains
_____________, 60-70% ___________-swells in water but does
Fabaceae not dissolve
30% _____________- more water soluble
component
Karaya gum or ___________ urens, _______odor of trees
__________ Sterculiaceae (Sterculius- diety that presides over manuring)

least soluble, absorbs water, swells several

times its original bulk and forms a
discontinuous type of mucilage

Present in __________Ò
Ghatti Gum or Anogeissus latifolia, Substitute for ________
______Gum ________________ Produces dispersions that are more viscous
than Acacia gum

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B. Seed Gums
Plantago Seed Plantago ________ Seed part: ______(outer seedcoat)
• Psyllium Seed Plantago ________ Bulk cathartic
• Plantain Seed Plantaginaceae Lubricant cathartic

Cydonium or __________vulgaris Seed part: Epithelium

________Seed Rosaceae Has thixotropic property
Guar Gum or ________ Cyamopsis Seed part: endosperm
tetragonolobus, Hydrates in cold water and stable in
_____________ acidic solutions
Locust Bean Gum Ceratonia siliqua, Seed part: endosperm
_______________ CAROB- Flour from the seed pods
Aka
______________
______________

C. Marine Gums
Sodium Alginate or ______________ Purified carbohydrate product extracted from
______ pyrifera, __________seaweeds by the use of dilute
Lessoniaceae alkali

FUCOIDAN
• from _____________
• treatment of ______________
Agar or Japanese Gelidium From _____Algae
Isinglas cartilagineum, Bulk laxative
Gelidiaceae Gel in bacteriological culture media
Gracilaria confervoides,
Gracilariaceae
Carrageenan or Gigartina mamillosa, From _____Algae or Seaweeds
Irish moss Chondrus crispus, 3 Types:
__________________ K______- Gelating agent
I_______- Gelating agent
L______- non-gelling; __________

Hydrolyzed to:
1.
2.
3.
4.

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 Uses:

Danish Agar Furcellaria fastigiata Similar to ________-carrageenan

Or Furcellarian
Furcellariaceae

D. Microbial Gum
Xanthan Gum Xanthomonas ____________property- enables toothpaste
campestris and ointments to hold shape and to spread
readily
Xanthomonadaceae

E. Plant Extract
Pectin Citrus grandis Purified carbohydrate product obtained from
C. __________, the dilute acid extract of the inner portion of
Rutaceae the rind of __________ or from apple
Unripe Fruit: __________
Just ripe Fruit: Pyrus malus,
Overripe Fruit: _____________ Uses: protectant, suspending agent and anti-
diarrheal agent (adsorbs toxins)

SUMMARY:
PLANT EXUDATES

SEED GUMS

MARINE GUMS

MICROBIAL GUMS

PLANT EXTRACT

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 QUICK QUIZ
1. Pectin
A. Shrub or Tree Exudate
B. Marine Gums
C. Seed Gums
D. Plant Extracts
2. Xanthan
A. Shrub or Tree Exudate
B. Marine Gums
C. Microbial Gums
D. Plant Extracts
3. Tragacanth
A. Shrub or Tree Exudate
B. Marine Gums
C. Seed Gums
D. Plant Extracts
4. Locust Bean
A. Shrub or Tree Exudate
B. Marine Gums
C. Seed Gums
D. Plant Extracts
5. Algin
A. Shrub or Tree Exudate
B. Marine Gums
C. Seed Gums
D. Plant Extracts

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 GLYCOSIDES
Are acetals in which the hydroxyl group of the _____________is condensed with the hydroxyl
group of the ___________ portion

Sugar: _________
Non-Sugar: _________or GENIN
Linked by an ______bond (SUGAR-ETHERS)

SALICIN

A. Anthraquinone Glycosides
Aglycone: ______________

Use: cathartics (drastic)

MOA: ________smooth muscle tone in the wall of the large intestine

Plant Constituents and Uses

Cascara Sagrada aka
________________
bitter taste: treat with
__________________
Dried bark of
Rhamnus Purshianus, __________________
Bark aged for 1 year
(__________is oxidized for a milder cathartic effect)
Constituents:
1. O-glycosides (10-20%)
a. Emodin
2. C-glycosides (80-90%)
a. Barbaloin

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 (optical isomer of Cascarosides _and _)
b. Chrysaloin
(optical isomer of Cascarosides _ and _)

Casanthranol- purified mixture of anthranol glycosides

Frangula or Dried bark of Rhamnus frangula, _________________
_________________ Cons: _____________
Present in __________Ò
Aloe Dried latex of the leaves of:

CURACAO ALOE: Aloe barbadensis, _______________

CAPE ALOE- Aloe ferox + Aloe Africana, ___________or
Aloe spicata, ____________

Cons: Barbaloin

Aloe Vera Gel:

Treatment of _____
Emollient (softens the skin)
Cathartic

Rhubarb/Rheum Dried roots and rhizomes of

_________Rhubarb:
• Rheum officinale, ______________
_________or Himalayan Rhubarb:
• Rheum emodi, ______________
• Rheum webbianum _________________

Cons: Rhein Anthrones

Senna Dried leaflets of
SenokotÒ Cassia acutifolia, ___________- ____________ Senna
Cassia angustifolia, ___________-___________ Senna

Cultivated in wet lands resembling _________

Cons: Sennosides A, B, C and D

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 Goa powder Lysigenous wood of Andira araroba, ______________

Cons: _______________
(extracted using: ____ benzene)

keratolytic agent (psoriasis, trichophytosis and chronic

eczema)

very irritating especially to mucous membranes

B. Saponin Glycosides
• Form colloidal solutions that foam upon shaking
• Bitter acrid taste
• Sternutatory, irritating to mucous membranes
• Destroy red blood cells by hemolysis
• Toxic to cold-blooded animals
• Aglycone: SAPOGENIN (_______________: toxic aglycone)

2 types of Saponins
1. neutral saponins are ___________

CycloPentanoPehydroPhenanthrene Nucleus

2. acid saponins are triterpenoidal

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 Plants Source Constituents and Uses
Glycyrrhiza or Roots and Rhizomes Cons:
___________ of Glycyrrhizin- ____times as sweet as
Glycyrrhiza glabra, sugar
_________________ Glycyrrhetic acid- anti-inflammatory
agent in dermatologicals

Uses:
1. Expectorant, demulcent
2. Mask the taste of bitter drugs
(Quinine)
3. Added to _________to increase its
foaminess
4. Added to _________ to impart a bitter
taste
5. Treatment of Addison’s disease and
PUD

Precaution:
May cause Na+ and H2O retention

Dioscorea or _____ Roots of Dioscorea Cons: Diosgenin or Botogenin (major

(Mexican Yam) spiculiflora, precursor of glucocorticoids)
________________

Dioscorea
floribunda,
_______________

BEST source of
steroids (according
to US Department
of Agriculture)
Ginseng ASIAN or KOREAN Cons: Panaxosides, Ginsenosides and
Panax ginseng, Chikusetsusaponins
_________________
AMERICAN Uses:

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 Panax quinquefolius 1. Aphrodisiac
_________________ 2. Adaptogen
3. Tonic
improve sense of well being

C. Cyanophore or Cyanogenic Glycosides

• Yield hydrocyanic acid/ cyanide- inhibits ______________
• Were used as flavorants and anti-cancer agents
Amygdalin Mandelonitrile Mandelonitrile Hydrocyanic
Glucose + + Glucose Acid +
Glucose Benzaldehyde

Enzymes: _________________ + ________________= _________________

Glycosides:
AMYGDALIN

PRUNASIN- product of the partial breakdown of amygdalin

LAETRILE
Aka Vitamin ____
Was used for the treatment of ________________
Banned by US FDA

PLANT SOURCES:
Almond kernels Prunus _____________, ______________
Bitter almond: var ___________
Sweet almond: var __________
Apricot kernels Prunus _____________, _____________

31
Wild Cherry Stems and Prunus _____________, _____________
Syrup: leaves
flavored vehicle
sedative-expectorant
Cherry kernels Prunus _____________, ______________

QUICK QUIZ
1. Alexandria Senna
A. Cassia alata
B. Cassia angustifolia
C. Cassia acutifolia
D. Quassia amara
2. Adaptogen and Tonic
A. Cascara Sagrada
B. Chrysarobin
C. Dioscorea
D. Ginseng
3. Use of Chrysarobin
A. Cathartic
B. Keratolytic Agent
C. Hemolytic Agent
D. Tonic
4. Purified Anthranol Glycosides derived from Cascara Sagrada
A. Cascarosides
B. Senokot
C. Sennosides
D. Casanthranol
5. Added to rootbeer to impart a bitter after-taste
A. Dioscorea or Yam
B. Ginseng
C. Glycyrrhiza or Licorice
D. Senna

32
 D. Cardiac or Cardioactive Glycosides

Sugar Non-sugar (STEROIDAL)

MECHANISM OF ACTION
(+) Inotropic agent
MOA: ____-_____ ATPase Pump

Increase ________________ of the heart

More complete emptying of __________

Shorter systole

Heart can rest between contractions

AGLYCONES:
• Cardenolide- __________
• Bufadienolide- skin of ___________ and _____________

Cardenolide and Bufadienolide

33
Plant Sources:
Common Name Scientific Name Glycoside
Grecian Foxglove Digitalis lanata,
_____________________
Foxglove Digitalis purpurea,
_____________________
Convallaria or Lilly of Convallaria _________,
the Valley _____________________
Adonis or Pheasant’s Adonis _________,
eye _____________________
Black Hellebore or Helleborus _________,
_________________ _____________________
Apocynum or Apocynum ________,
____________ _____________________
Strophanthus Strophanthus kombe,
____________________
Oleander (Adelfa) Nerium oleander,
___________________
Squill Urginea maritima,
___________________

E. Isothiocyanate Glycosides (Mustard Oils)

Family: Cruciferae (now: ______________)
Uses: local irritant, emetic, rubefacient, vesicant, condiment

Sinigrin Sinalbin Gluconapin

______Mustard ________Mustard Rapeseed

Brassica_______ Brassica _______ Brassica __________

Sinigrin Sinalbin

34
 _______Isothiocyanate _______Isothiocyanate

F. Flavonol Glycosides/Flavonoids
Yellow pigments
Examples: Vitamin P
Rutin, Quercitrin Rutin and Hesperidin
Citrus Bioflavonoids: Hesperidin,
Hesperetin, Diosmin, Naringen Uses:
1. treatment of bleeding due to capillary
fragility
Family Rutaceae 2. treatment of the symptoms of
common colds

G. Alcohol Glycosides
Salicin Salix and Populus
Populin (benzoyl salicin) Salix purpurea, _______________
Salix fragilis, _______________

Salicin Saligenin (Salicyl alcohol) Uses:

+ Salicyl alcoholàSalicylic acid
Glucose Anti-rheumatic agent

35
H. Lactone Glycosides
Coumarin
(ortho-hydroxycinnamic acid)
Dicumarol
(bishydroxycoumarin)
Synthetic: Warfarin
Cantharides
Aka
1. ____________fly
2. ____________fly
3. ____________fly
Psoralens
Tonka Beans
Dipteryx odorata, ________________
Flavoring agents
Use:___________
Yellow Sweet Clover
Melitotus officinalis, __________________
Use: anti__________
Cantharis vesicatoria, ________________
Cons: Cantharidin
Effects: irritant, vesicant and rubefacient
Internal Effecrs: excreted in the kidneys, irritates the
urinary tract causing _________________
Topical: treatment of warts
Photosensitizing furocoumarins
36
 1. Methoxsalen (8-methoxypsoralen, or xanthotoxin)

Laceflower
Ammi majus, ___________________
Repigmentation in ________

2. Trioxsalen- synthetic

I. Phenol Glycoside
Arbutin Uva ursi or Bear berry
(yields hydroquinone and glucose) Arctostaphylos uva ursi,
_________________
Astringent and diuretic

J. Aldehyde Glycosides
Vanillin
-cured fruits of Vanilla planifolia, __________________

SWEATING
Exposed to the sun during the day, covered with woolen blankets and stored in
wooden blankets at night

Use: flavorant
IUPAC: _____________________________

37
 Qualitative Tests for Glycosides
Chemical Test Substances Identified
Modified Borntrager’s Test ________________glycosides
(+) result:
Guignard Test ________________glycosides
(+) result:
Keller-Killiani Test ________________glycosides
(+) result:
Froth Test ________________glycosides
(+) result:
Hemolysis Test ________________glycosides
(+) result: REDà ______(Beta hemolysis)

QUICK QUIZ
1. 4-hydroxy-3-methoxybenzaldehyde
A. Salicin C. Vanillin
B. Arbutin D. Rutin
2. Scillaren A
A. Cardioactive
B. Steroidal
C. Flavonol
D. A and B
3. Rutin and Hesperidin are
A. Vitamin R
B. Vitamin P
C. Vitamin H
D. Vitamin F
4. Sinigrin and Sinalbin are
A. Isothiocyanate Glycosides
B. Flavonol Glycosides
C. Alcohol Glycosides
D. Phenol Glycosides
5. Salicin is
A. Isothiocyanate Glycosides
B. Flavonol Glycosides
C. Alcohol Glycosides
D. Phenol Glycosides

38
 TANNINS
• Complex substances
• mixtures of _____________
• difficult to separate because they do not ____________

Types Hydrolyzable Tannins Condensed Tannins

Chemically related Pyrogallol Catechol
to

Products of condensation
of CATECHIN

Composition Hydrolyzed to form Phenolic acids When treated with

and sugars hydrolytic agents, these
tannins tend to polymerize,
Gallic Acid yielding insoluble, red-
colored products known as
_____________

Aka NON- ______________

Ellagic Acid tannins

Ferric Chloride ___________ppt _________ppt

Test
Bromine Water TS

39
 Medicinal Use of Tannins Industrial Use of Tannins
A. Astringents 1. Tanning of Leather
1. skin
2. GI Animal HidesàLeather

B. Treatment of BURNS Type of Leather:

(The proteins of the exposed tissues are _______: hydrolysable tannins
precipitated and form a mildly antiseptic,
protective coat under which the _______: condensed tannins
regeneration of new
tissues may take place)

C. Antidote for ____________Poisoning 2. manufacture of _______

Goldbeater Skin Test

• to differentiate a _______tannin from a ________tannin
• (+) dark discoloration- ___________ tannin
• (-) dark discoloration- ____________ tannin
• PRINCIPLE: Protein precipitation

Example of Pseudotannin:
Arecatannin
• Carcinogen (may cause ___________,__________ cancer)
• Seed of Areca catechu, Arecaceae

Tannin-containing Plant Materials

Hamamelis or Leaves of Hamamelis virginiana, Hammamelidaceae
Witch Hazel Cons: _____________tannin and 2-hexen-1-al (aldehyde
volatile oil)

Uses: astringent, hemostatic

40
 Nutgall Excrescense obtained from the young twigs of Quercus
infectoria, Fagaceae when the insect ________________,
Cynipidae punctures the plant

Principal cons: _______________

Use: alkaloidal precipitant

QUICK QUIZ
1. Red, insoluble compounds formed when Condensed Tannins are treated with
hydrolytic agents
A. Prontosil
B. Phlobaphenes
C. Clofazimine
D. Erythromycin
2. Excrescence produced by Cynips tinctoria
A. Peanut
B. Coconut
C. Witch Hazel
D. Nutgall
3. Medicinal use of Tannins
A. Astringent
B. Cathartic
C. Analgesic
D. Tanning of Leather
4. Principle behind Goldbeater Skin Test
A. Reduction
B. Oxidation
C. Dehydration
D. Protein Precipitation
5. Hydrolyzable Tannins
A. Produce a greenish black precipitate with FeCl3 TS
B. Produce a bluish black precipitate with FeCl3 TS
C. Converted to sugars and phenolic acids when hydrolyzed
D. B and C

41
 LIPIDS
• esters of long chain fatty acids and alcohols

Fixed oils Fats Waxes

Esters of _______fatty acids Esters of _______fatty acids Esters of long chain fatty
and ___________. and ___________. acids and high molecular
weight alcohols

(Cetyl and Stearyl Alcohol)

From ________ From __________ From_______ or _______
Ex: Olive oil, Peanut oil Ex: ________, Tallow Ex: Beeswax

__________at room ________at room

temperature temperature
Theobroma oil/Cacao butter Cod Liver Oil

Uses of Fats and Fixed Oils

1. Emollients
2. Solvent for IM injections
• Co
• Co
• Pe
• Se
3. Castor Oil- Cathartic
4. Manufacture of soaps
5. High caloric value- nutrient

Uses of Waxes
1. ______________ agents
2. Manufacture of

A. FIXED OILS
FIXED OIL SOURCE AND USES
Castor Oil Seeds of ___________ communis, Euphorbiaceae
LOCAL NAME:
___________- toxic lectin or hemagglutin
TRIRICINOLEIN- converted to ___________________(cathartic effect)

42
 Other uses:
1. plasticizer in flexible collodion
2. restoration and maintenance of vaginal acidity
3. hydrogenated oil: stiffening agent
Olive Oil Ripe fruits of Olea europaea, _______________
Aka Sweet oil

Grades:
1. Virgin oil
a. First grade- less pressure
b. Second grade- more pressure
2. Technical grade- extracted using __________
3. Sulfur grade- extracted using ___________
4. Tournant oil (low grade)- fallen and ___________fruits
Peanut Oil Seeds of Arachis hypogaea, _______________
Use: solvent for __________
Soybean Oil Seeds of Glycine soja, ____________
Source of
Lecithin- control deranged lipid and cholesterol metabolism
Stigmasterol-precursor of steroidal hormones
Cottonseed Oil Seeds of Gossypium hirsutum, _______________
Use: solvent for __________

Sesame Oil Seeds of Sesamum indicum, ________________

Aka Benne oil or Teel oil
Use:
Solvent for _________; nutrient
Almond Oil Seeds of Prunus amygdalus, _______________
dulcis: sweet
amara: bitter
use: emollient
Persic Oil Seeds of Prunus armeniaca, ______________
(Apricot Kernel Oil)
Coconut oil Seeds of Coconut, Cocos nucifera, _____________
Constituents: 50% ___________, 20%_____________
Use: nutrient
Corn Oil Embryo of Zea mays, ______________
Use: solvent for ___________; nutrient

Safflower oil Seeds of Carthamus tinctorius, ______________

43
 Use: ________
Sunflower oil Seeds of Helianthus annuus, ____________
Use: ________
Ethiodized oil Iodine addition product of the ethyl ester of the fatty acids of poppy
injection seed oil (Papaver somniferum, Papaveraceae)
Use: ________in hysterosalpingography and lymphography

B. Fats and Related Compounds

FAT SOURCE USES
Theobroma oil Seeds of Theobroma cacao, Theobroma- Theo (____);broma (______)
_________________
Theobroma oil or ____________
-fat obtained from the seeds
Use:

Physical Forms:
Alpha
Beta
Beta Prime
Gamma

Cocoa- powder prepared from the

roasted seeds

Lanolin fat-like substance from the Water content: 25-30%

wool of sheep, ______ Aka hydrous _________
_________, Bovidae Use: ointment base

Woolfat Aka __________ Lanolin

Water content: 0.25%
Use: ointment base
Cod Liver Oil Cod- Gadus morrhua, Cod Liver Oil
Gadidae • only liquid animal fat
• source of Vitamin __,__ and
EFA’s

Sodium morrhuate
• Sodium salt of the fatty acids Cod
liver oil

44
 • Use: sclerosing agent

C. Waxes
Esters resulting from the condensation of high molecular weight, straight chain acids and high
molecular weight, straight-chain alcohols

Use: stiffening agent- harden cerates, ointments or cosmetic creams

WAX SOURCE USES

Spermaceti head of Sperm whale Physeter Alternatives:
____________, Physeteridae Cetyl ester wax- synthetic
(endangered) Hydrogenated jojoba oil

Jojoba oil seeds of Simmondsia chinensis, -hydrogenated form-

B____________ alternative to Spermaceti;
emollient
Beeswax aka Yellow wax Principle constituent:
-honeycomb of bees, Apis___________, ___________________
Apidae Use: stiffening agent
White wax: bleached yellow
wax

Carnauba wax leaves of Copernicia prunifera, manufacture of candles, wax

________________ varnishes, leather and
furniture polishes

ASSAY OF LIPIDS

ACID VALUE Aka ACID NUMBER

mg of alcoholic ________needed to _________the free fatty
acids in 1 gram sample
Degree of _______________
ESTER VALUE Aka ESTER NUMBER
mg of alcoholic ________needed to _________the free fatty
acids in 1 gram sample
Degree of _______________
SAPONIFICATION Aka __________________NUMBER
VALUE mg of alcoholic ________needed to _________ and
__________the free fatty acids in 1 gram sample

45
 SV= AV + EV

IODINE VALUE Aka IODINE NUMBER

amount of Iodine absorbed by 100g sample
Degree of ________________

Type Iodine Number Examples

Non-Drying Oils

Semi-Drying Oils

Drying Oils

HALPHEN TEST
BAUDOUIN TEST

QUICK QUIZ
1. Aka Hydrous Woolfat
A. Lanolin
B. Beeswax
C. Anhydrous Lanolin
D. Carnauba wax
2. Olive oil isolated from fallen and decomposing Olive fruits
A. Technical grade
B. Virgin
C. Tournant
D. Sulfur grade
3. Official solvents for IM injection, except:
A. Coconut oil
B. Corn oil
C. Sesame oil
D. Peanut oil
4. Esters of high molecular weight alcohols and long chain fatty acids
A. Fats

46
 B. Fixed oils
C. Waxes
D. Prostaglandins
5. Jojoba oil is isolated from the seeds of Simmondsia chinensis, ____________.
A. Boranginaceae
B. Bovidae
C. Buxaceae
D. Fabaceae

VOLATILE OILS
• Odorous principles
• Aka
o Ethereal oils
o Essential oils

ROLE IN PLANTS: Insect ___________and insect repellants

Specialized Secretory Structures

Glandular hairs Labiatae
Ex: Mentha piperita, Lamiaceae (Peppermint)
Modified ___________Cells Piperaceae
Ex: Piper nigrum, Piperaceae (Black Pepper)
_________(oil tubes) Umbelliferae
Ex: Foeniculum vulgare, Apiaceae (Fennel)
Lysigenous and Pinaceae and Rutaceae
Schizogenous Passages Ex:
Pinus palustris, Pinaceae (Pine Tree)
Citrus limon, Rutaceae (Lemon)

METHODS OF OBTAINING VOLATILE OILS

A. Distillation
Type Sample Examples
Water Distillation dried _________ oil
Water and Steam Distillation Either dried or _________ oil
fresh _________ oil

Direct Steam Distillation Fresh _________ oil

47
 Spearmint oil

Destructive Distillation Empyreumatic Tar oil

(High _________without air) oils

B. Enzymatic Hydrolysis
Glycosidic Volatile Oils _________Oils
Enzyme: Myrosin

C. Expression
Ecuelle Puncturing the oil glands by rolling the Lemon Oil
fruit over a trough lined with sharp Orange Oil
projections that are long enough to
reach the epidermis and pierce the oil
glands located in the outer portion of
the peel
Enfleurage An odorless, bland, fixed oil or fat is Rose Oil
spread in a thin layer on glass plate.
The flower petals are placed on the fat
for a few hours; then, repeatedly old
petals are removed, and a new layer of
petals is introduced. After the fat has
absorbed as much fragrance as
possible, the oil may be removed by
extraction with alcohol

MEDICINAL AND COMMERCIAL USES OF VOLATILE OILS

In Medicine: flavorants, carminatives
CLOVE OIL
THYME OIL
PINE OIL
WINTERGREEN OIL

48
 In the industry,
Fabrication of Perfumes
Top Notes Middle Notes Base Note
Most volatile Intermediate Low volatility and high tenacity
(leave skin ___________and (FIXATIVES- Staying Power)
easily) ____________
L_______ Thyme Vanillin
Anise Neroli Musk- dried secretion from the preputial
Lavender Rose follicles of the male musk deer of Asia
Civet- a glandular secretion appearing in an
outwardly discharging pocket underneath
the posterior appendage of both the male
and female civet cats
Ambergris- pathologic product formed in
the stomach of the _______________when it
is feeding on squid or cuttlefish.

CONSTITUENTS OF VOLATILE OILS

Parts Description
Eleoptene Hydrocarbon portion of the oil, which is __________
Ex: E_________, E___________ and Methylsalicylate
Stereoptene Oxidized hydrocarbon portion of the oil, which is __________
Ex: M________, T_________and A___________

Isoprene

Monoterpenes ___Isoprene units

Sesquiterpenes ___Isoprene units
Diterpenes ___Isoprene units
Triterpenes ___Isoprene units

49
 BIOSYNTHESIS OF VOLATILE OIL CONSTITUENTS
(NOTE: ANETHOLE IS A PHENYLPROPANOID)
Terpene derivatives _______________Acid Pathway
(Alicyclic or
Aliphatic Menthol Camphor
Compounds)

Phenylpropanoids _______________Acid Pathway

(Aromatic
Compounds ) Thymol Eugenol

Anethole Methylsalicylate

DIFFERENCES BETWEEN VOLATILE AND FIXED OILS

Volatile Oils Fixed Oils

_________from natural sources Extraction

Isoprenes Esters of __________and fatty acids

Do not leave a permanent grease spot Leave a permanent grease spot

50
 Cannot be saponified by alkalis Can be saponified by alkalis

Do not become rancid; they oxidize and Become___________

____________

QUICK QUIZ
1. Modified Parenchymal Cells
A. Mentha piperita
B. Piper nigrum
C. Mentha spicata
D. Citrus limon
2. Lysigenous and Schizogenous Passages
A. Mentha piperita
B. Piper nigrum
C. Mentha spicata
D. Citrus limon
3. Glandular Hairs
A. Mentha piperita
B. Piper nigrum
C. Pinus palustris
D. Citrus limon
4. Oil tubes or Vittae
A. Coriandrum sativum
B. Mentha piperita
C. Piper nigrum
D. Pinus strobus
5. Isolation of volatile oils from flower petals
A. Enfleurage
B. Ecuelle
C. Water Distillation
D. Water and Steam Distillation

51
1. MONOTERPENES
A. HYDROCARBON
Hydrocarbon Source Volatile Oil Notes
a and b _______ Turpentine
PINENE _________, Oil
Pinaceae

___________Turpentine Oil
(+ NaOH)
use: expectorant

Terpene Hydrate or _________

(Rectified Turpentine Oil + HNO3
use: expectorant
LIMONENE _______ _______, Lemon Oil
Rutaceae

__double bonds, 1 cycle

B. ALCOHOL
Alcohol Source Volatile Oil Notes
MENTHOL Mentha___________, Peppermint Oil Use: _________
Lamiaceae

MENTHOL Mentha _________, Japanese Use:_________

(more in quantity Lamiaceae Peppermint Oil
but has inferior
flavor)

52
 TERPINEOL Pinus palustris, Pine Oil Disinfectant
Pinaceae

LINALOOL Coriandrum Coriander Oil

sativum, Apiaceae

Citrus aurantium, Orange Flower Oil

Rutaceae (_________Oil)

GERANIOL Rosa gallica, Rose Oil

Rosaceae

C. ALDEHYDE
Acyclic (Aliphatic and Alicyclic)- Terpenoids
Aldehyde Source Volatile Oil Notes
CITRAL Citrus limon, Lemon Oil CITRAL
Rutaceae 3 parts Geranial +
1 Part Neral

uses:
flavorant
carminative
stomachic

53
Cyclic- Phenylpropanoids
Aldehyde Source Volatile Oil Notes
Cinnamaldehyde Cinnamon Oil Cinnamon “sweet
Cinnamomum ____________oil wood”
loureirii
Use: flavorant
Cinnamomum
____________

Lauraceae

Vanillin Vanilla planifolia Vanilla 4-hydroxy-3-

methoxybenzaldehyde
Orchidaceae

Use: flavorant

D. KETONE
Ketone Source Volatile Oil Notes
Camphor Cinnamomum Camphor Oil “Kafur”- ______
___________,
Lauraceae

54
 Uses: antipruritic,
rubefacient and
anti-infective
(-)-Carvone Mentha Spearmint Oil Uses: flavor,
__________, carminative
Lamiaceae

(+)-Carvone Carum carvi, Caraway oil Uses: flavor

______________

E. PHENOL
Ketone Source Volatile Oil Notes
Thymol Thymus Thyme Oil IUPAC:
__________,
Lamiaceae
(leaves)

Use: antifungal and

antibacterial agent
Eugenol ____________ Clove oil IUPAC:
caryophyllus,
Myrtaceae
(dried flower buds)

55
 Use: flavorant and
dental analgesic

F. PHENOLIC ETHER
Phenolic Ether Source Volatile Oil Notes
Myristicin Myristica Nutmeg Oil or Uses: flavorant, carminative
fragrans, Myristica Oil and hallucinogen
Myristicaceae

Trans-anethole Anise Anise oil

Pimpinella Fennel oil
anisum,
Apiaceae

Fennel
Foeniculum
vulgare,
Apiaceae

G. OXIDE
Oxide Source Volatile Oil Notes
Cineole or Eucalyptus Eucalyptus Oil Use: flavorant
Eucalyptol globulus,
Myrtaceae

56
 Ascaridole Chenopodium Chenopodium oil
______________,
______________

H. ESTER
Ester Source Volatile Oil Notes
Methylsalicylate Gaultheria Gaultheria Oil Flavorant (toxic to
procumbens, _____________Oil children)
Ericaceae Local irritant
Antiseptic
Betula________, Betula Oil Anti-rheumatic
Betulaceae Sweet Birch Oil

Other ESTER MONOTERPENES

(-) Linalyl acetate
Bornyl acetate
Allyl and Acrinyl
Isothiocyanate

57
2. SESQUITERPENES
Plant Source Sesquiterpene Uses
Feverfew Tanacetum Parthenolide Treatment
parthenium, of_________,
______________ arthritis, migraine,
menstrual
problems
Chicory Chicorium intybus, Inulin ____________,
______________ Chicorioside treatment of liver
ailments
Fish berries Anamirta cocculus, Picrotoxin Antidote for
Menispermaceae _____________and
other narcotics
Santonica/Wormseed Artemisia cina, Santonin _____________
_____________
Sweet Annie Artemisia annua, Artemisinin/ Anti___________
_______________ ___________
Cotton Plant Gossypium Gossypol Contraceptive
hirsutum,
Malvaceae

3. DITERPENES
Plant Source and Uses
Ginkgo Ginkgo _________, Ginkgoaceae
Cons: Ginkolides
Use: improve cerebral circulation (___________)
ADR: ___________(inhibit Platelet aggregating factor)
Pacific Yew Taxus brevifolia, Taxaceae
Paclitaxel_________Ò
Use: ____________

10-deacetylbaccatin
(Taxus __________)

58
 TRITERPENES
Plant Source and Uses
Neem Tree Azadirachta indica, Meliaceae
Use: ____________
Quassia wood Quassia amara, Simaroubaceae
cons: Quassinoids
use: anti-feedant

QUICK QUIZ
1. Which of the following is produced via Shikimic Acid Pathway?
A. Terpineol
B. Methylsalicylate
C. Vanillin
D. B and C
2. Which of the following is produced via Mevalonic Acid Pathway?
A. Menthol
B. Camphor
C. Terpineol
D. All of the above
3. Which of the following is a sesquiterpene?
A. Paclitaxel
B. Quassinoids
C. Menthol
D. Artemisinin
4. Which diterpene is employed in the treatment of ovarian and breast cancer?
A. Ginkgolides
B. Parthenolides
C. Paclitaxel
D. Santonin
5. Which of the following is a dental analgesic?
A. Thymol
B. Menthol
C. Camphor
D. Eugenol

59
 RESINS and RESIN COMBINATIONS
• natural products with ______________chemical nature (mixture of resin acids,
resin alcohols, resinotannols, esters and resenes)
• amorphous compounds
• hard, transluscent or transparent
• easily melts when heated

A. Resins
Common Scientific Name and Resin Uses
Name Family Name
Pine Trees Pinus palustris, Rosin or Use:_____________agent
Pinaceae _____________
Podophyllum, Podophyllum Podophyllin Use: _____________
__________, peltatum,
__________ Berberidaceae Derivatives:
Etoposide, Teniposide
Eriodictyon or Eridictyon Eriodictyol Disguise bitterness of
____________ californicum, QUININE
________________
Jalap Exogonium purga, Jalap Resin Use:___________
________________
Mastic Pistacia lentiscus, Mastichic Acid Use:___________
______________
Kava or Piper methysticum, Yangonin and Use: ___________
______________ ________________ Methysticin
Marijuana Cannabis sativa, Hashish Resin:___________
______________ (flowering tops)
(Tyler: Moraceae)
Euphoric
Agent:____________

Fiber: ____________

60
 B. OLEORESIN
Resin + __________
Oleoresin Source Uses
Turpentine Pinus palustris, ______________
Gingerol Ginger or Luya
Zingiber officinale,
_________________
Balsam of Copaiba Copaifera spp, ________________
Capsaicin Capsicum/Cayenne Pepper
Capsicum frutescens, ______________

C. OLEOGUMRESIN
Resin + Gum + ___________
Oleogumresin
Myrrh or Gum Myrrh
Asafetida or _____________
Source and Uses
Commiphora molmol, __________________
Use: embalming fluid, astringent
Ferula asafetida, __________________
Use: flavorant, ___________

D. Balsams
Balsam Source Uses
Storax/Styrax Liquidambar orientalis, Pharmaceutic aid in CBT
____________________ (Compound Benzoin Tincture)
“fluid from amber”
Peruvian Balsam Myroxylon pereirae, Parasiticide (Scabicide)
or Peru Balsam ___________________
(discovered by J. Pereira)
Tolu Balsam Myroxylon balsamum, Pharmaceutic aid in CBT
____________________
Benzoin Styrax benzoin, Antiseptic
_________________

Compound Benzoin Tincture

_________, Aloe, __________, Tolu Balsam, Benzoin

61
 QUICK QUIZ
1. Rosin
A. Resin
B. Oleoresin
C. Oleogumresin
D. Balsam
2. Myrrh
A. Resin
B. Oleoresin
C. Oleogumresin
D. Balsam
3. Storax
A. Resin
B. Oleoresin
C. Oleogumresin
D. Balsam
4. Gingerol
A. Resin
B. Oleoresin
C. Oleogumresin
D. Balsam
5. Hashish
A. Resin
B. Oleoresin
C. Oleogumresin
D. Balsam

ALKALOIDS
• bitter, basic, ____-containing compounds with marked physiologic activities
• AMINES (end with –______)
o Primary(RNH2)
o Secondary (R2NH)
o Tertiary (R3N)

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 o Quaternary (R4N+)
o
SOLUBILITY
Alkaloidal Bases (Free Bases)
Ex: __________
Insoluble or Sparingly soluble in water (POLAR SOLVENTS)
Soluble in ether, chloroform and benzene (NON-POLAR SOLVENTS)

Alkaloidal Salts
Ex: __________ __________
Insoluble in non-polar solvents
Soluble in water

A. PYRIDINE-PIPERIDINE ALKALOIDS
• Synthesized from Ornithine and Nicotinic Acid

Pyridine Piperidine

Plant Scientific Name Alkaloid Uses

1. Tobacco Leaves of
Nicotiana
tabacum
Solanaceae N_________
2. Betel nut Fruits of
Areca catechu
Arecaceae
A________
3. Indian Leaves of
tobacco Lobelia inflata
Campanulaceae
L________

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B. TROPANE ALKALOIDS
Biosynthesis of Tropane Alkaloids
Tropane- dicyclic compound formed by the condensation of pyrrolidine precursor (Ornithine)
with 3 acetate derived carbon atom

Pyrrolidine from Ornithine

Tropine
Tropine
(feeding studies with labeled
ornithine have revealed that
this amino acid is incorporated
steriospecifically to form
pyrrolidine ring of tropine)

The remaining 3 carbons are

Tropic Acid
derived from acetate

Phenylalanine

(-) Tropic Acid

(-) Hyoscyamine
Racemic: ___________

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 SOLANACEOUS ALKALOIDS
Principal:

1. (-) Hyoscyamine • ester of tropine and

tropic acid

2. Atropine • aka _________

hyoscyamine

3. Scopolamine (aka • abundant in Datura

hyoscine) ______, D. fastuosa,
D. alba
• upon hydrolysis, it
yields scopoline and
tropic acid

USES:
Competitive inhibitors of Ach in post ganglionic synapse (muscarinic receptors)
Anti-__________________ agents
1. Anti-spasmodic
• ulcerative colitis
• gastroenteritis
2. Anti-sialogogue- decrease ____________
• adjunct to anesthesis
3. Mydriatic
• Iritis- inflammation of the iris
4. Antidote for _______________ insecticide poisoning (esp. _________)
5. Scopolamine- CNS _________(treatment of motion sickness)

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 PLANTS CONSTITUENTS
1. Belladonna or ____________Leaf Principal alkaloid: (-) Hyoscyamine
leaves of Atropa belladonna Less abundant: atropine

Characteristics:
1. The stems are cut about halfway down
WHEN THE FRUITS BEGIN TO FORM
and the Belladonna Alkaloids are most
abundant
2. The genus name ATROPA was derived
from____________, the Greek Fate that
cuts the thread of life. The plant is
TOXIC.

2. Hyoscyamus or ___________ Principal alkaloid: (-) Hyoscyamine

leaves of Hyoscyamus niger Less abundant: Scopolamine

3. Stramonium aka Jimson Weed or Principal alkaloid: (-)Hyoscyamine

Jamestown Weed Less abundant: Scopolamine and
leaves of Datura stramonium Atropine

4. Coca or Coca Leaves

dried leaves of
Erythroxylum coca,
_____________________
Principal alkaloid: Cocaine Cocaine HCl
a. local anesthetic
b. ingredient of Brompton’s cocktail
(manage severe pain)
c. CNS stimulation (cerebral stimulation,
euphoria, psychic dependence and
tolerance)

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 C. QUINOLINE ALKALOIDS
Tryptophan Quinoline

Cinchona Cinchona ________ Q_________ Q_________-

Bark (RED Cinchona) streoisomer of
Quinine
Cinchona ________
(YELLOW Cinchona)

Cinchonaceae use:

use:

QUICK QUIZ

1. Tropane Alkaloids are derived from:

A. Tryptophan C. Phenylalanine
B. Tyrosine D. Histidine
2. Alkaloid from Areca catechu, used as a taenicide.
A. Nicotine C. Arecoline
B. Lobeline D. Arecatannin
3. Tropane alkaloids are most abundant when
A. the fruits are ripe C. the fruits begin to form
B. the fruits begin to rot D. the flowers begin to bloom
4. Quinine and Quinidine are
A. Isoquinoline Alkaloids C. Tropane Alkaloids
B. Pyridine-Piperidine Alkaloids D. Quinoline Alkaloids
5. Cocaine is
A. Isoquinoline Alkaloids C. Tropane Alkaloids
B. Pyridine-Piperidine Alkaloids D. Quinoline Alkaloids

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D. ISOQUINOLINE ALKALOIDS

Phenylalanine or Tyrosine Isoquinoline

Plant Scientific Name Alkaloid Uses

1. Ipecac Dried roots and Ipecac_____-
rhizomes of emetic in cases of
Cephaelis poisoning
_______________,
E_________ or
Rubiaceae Ipecac fluidextract-
methylcephaeline
______x more
potent than Ipecac
syrup
2. Hydrastis or Dried roots and
Goldenseal rhizomes of
Hydrastis
_______________,
H___________
Ranunculaceae
3. Sanguinaria or Dried rhizome of
____________ Sanguinaria
_______________,
Papaveraceae
S___________
4. Curare Bark and stems of Non-depolarizing
Strychnos neuromuscular
castelnaei, blocking agent
Loganiaceae
T______________

Opium

68
 Air-dried milky exudate obtained from the unripe capsules of Papaver somniferum,
Papaveraceae

Phenanthracene

Preparations:
1. Paregoric or ___________Opium Tincture
2. Laudanum or Opium __________
use: anti-peristaltic

Morphine Most __________ Use:

“MORPHEUS” Most __________ Narcotic
Greek god of _________
__________

Codeine Most widely used Use:

Semi-synthetic ___________
Aka ___________

Heroin Aka ___________ Effect:

____________

Apomorphine Dehydration of Emetic

HCl __________

Papaverine Antitussive

Noscapine No narcotic Antitussive

Aka properties=___________
__________

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E. INDOLE ALKALOIDS
Tryptophan Indole

Plant Scientific Name Alkaloids and Uses

Rauwolfia serpentina Dried root and rhizome of
Rauvolfia
_______________,
Apocynaceae
R_____________
Use:_____________
Catharanthus or Vinca Dried whole plant of
_______________ roseus,
Apocynaceae

Vinblastine, Vincristine
Use:______________
Nux Vomica Dried ripe seed of Strychnine- poison; causes
Strychnos nux vomica, convulsions
Loganiaceae

Brucine-______________

Physostigma or Calabar Dried ripe seed of Physostigmine or _______

bean _______________a
venenosum, Fabaceae

70
 Ergot Dried sclerotium of Ergotamine- treatment of
Claviceps __________
_______________,
Clavicipitaceae on rye,
Secale _______________,
Poaceae
Ergonovine- _______agent

LSD___________________;
Most active and most
specific psychotomimetic
agent

F. IMIDAZOLE ALKALOIDS
Histidine Imidazole

Plant Scientific Name Alkaloid and Use

Pilocarpus Leaflets of Pilocarpus Pilocarpine or ________
jaborandi, Use:_________________
_______________

G. STEROIDAL ALKALOIDS
Cholesterol

71
 Plant Scientific Name Alkaloid and Use
Green Hellebore Dried roots and rhizomes Veratridine- cardiac
of Veratrum depressant
________Melanthiaceae
White Hellebore Dried roots and rhizomes
of Veratrum _______
Melanthiaceae

H. ALKALOIDAL AMINES
Phenylalanine and Tyrosine Amine
RNH2
R2NH

Plant Scientific Name Alkaloid and Use

Ephedra or Ma Huang Overground portion of Ephedrine
Ephedra sinica, Gnetaceae Effect: ______________

Autumn Crocus Seeds and corms Colchicine

Colchicum autumnale, Use: _____________
Liliaceae

72
 Khat or Abyssinian Tea Fresh leaves of (-) cathinone (similar to
_______________ edulis, amphetamines)
Celastraceae effect:

Peyote or Mescal Buttons Dried tops of Lophophora Mescaline or

williamsii,_______________ _______________

Effect: _____________

I. PURINE BASES
Methylxanthines

Phosphodiesterase Inhibitors
Effect: Increase in cAMP and release of Epinephrine

73
1. relaxation of smooth muscles of the bronchi and pulmonary blood vessels (____________)
2. CNS stimulation
3. induction of diuresis (_____________)
4. increase in gastric acid secretion
5. inhibition of uterine contractions (_______________)
6. positive chronotropic and inotropic effect on the heart

Plant Scientific Name Alkaloid IUPAC Name and

uses
Kola, Cola and Dried cotyledon of Caffeine IUPAC:
Kolanuts Cola nitida, Malvaceae ________-
Coffee Bean Dried ripe seeds of trimethylxanthine
Coffea _________,
Rubiaceae use:___________
Thea or Tea Leaves and leaf buds Theophylline IUPAC:
of Camellia _________, ________-
Theaceae dimethylxanthine

use:___________

Cacao Ripe seed of Theobromine IUPAC:

Theobroma cacao, ________-
Malvaceae dimethylxanthine

use:___________

SUMMARY OF ALKALOIDS
Pyridine Piperidine Lobeline
Alkaloids Arecoline
Nicotine

Tropane Alkaloids Hyoscyamine

Atropine
Scopolamine
Cocaine

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 Quinoline Alkaloids Quinine
Quinidine

Isoquinoline Alkaloids Emetine

Hydrastine
Sanguinarine
Morphine
Tubocurarine
Imidazole Pilocarpine

Indole Alkaloids Reserpine

Vincristine, Vinblastine
Physostigmine
Ergotamine, Ergonovine
Strychnine, Brucine
Steroidal Veratridine

Alkaloidal Amines Ephedrine RNH2-Primary AMINES

Mescaline R2NH- Secondary AMINES
Colchicine
Cathinone
Methylxanthines or Purines Caffeine
Theophylline
Theobromine

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MATCH!
Column A Column B
A. Cocaine
B. Morphine
C. Caffeine
D. Quinine
E. Reserpine
1. F. Pilocarpine

2.

3.

4.

5.

6.

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 QUICK QUIZ
1. Reserpine
A. Isoquinoline Alkaloids
B. Indole Alkaloids
C. Tropane Alkaloids
D. Quinoline Alkaloids
2. Morphine
A. Isoquinoline Alkaloids
B. Indole Alkaloids
C. Tropane Alkaloids
D. Quinoline Alkaloids
3. 1,3,7- trimethylxanthine
A. Caffeine
B. Theobromine
C. Theophylline
D. Purine
4. Pilocarpine
A. Isoquinoline Alkaloids
B. Purine Alkaloids
C. Tropane Alkaloids
D. Imidazole Alkaloids
5. Uses of Tropane Alkaloids, except:
A. Antidote for Organophosphate insecticide poisoning
B. Anti-sialogogue
C. Anti-emetic
D. Anti-spasmodic

77