PHARMACOGNOSY

Mark Miguel P. Latras, RPh

What is Pharmacognosy?
 “pharmakon” (drug) + “gnosis” (knowledge)

 dealswith the BIOLOGICAL, BIOCHEMICAL &

ECONOMIC features of drugs of biological origin
& their constituents
Focus of Pharmacognosy
 Identification of plants and animals
 Chemistry
 Evaluation, preservation and use or
application of crude drugs
 Toxicology
 History, distribution, collection and selection
 Preparation and commerce
BRIEF HISTORY

BABYLONIANS

HINDUS

EGYPTIANS GREEKS

GERMANS
DRUG CONSTITUENTS
 Natural - DIRECTLY OBTAINED from plants and
animals in nature (e.g. Natural camphor from
steam distillation of camphor tree)

 Synthetic
 Total synthesis – totally made in the lab
(cyclopentadiene  Camphor)

 Semi-synthesis – starting mats came from nature

(pinene from pine stumps  Camphor)
Terms to remember
1) Crude drugs – undergone only the process of
Collection and drying

2) Natural substance – found in nature

3) Derivatives/Extractives – chief principles of

crude drugs that are separated (e.g. through
extraction) and used in a specific manner

 Technical term for solvent: __________

 Undissolved portion: ____
Appropriate solvents/menstruum
CHIEF PRINCIPLE SOLVENT USED

Fat Hexane
Resins Alcohol
Chlorophyll Acetone
Chrysarobin HOT benzene
Inulin Alcohol
Pectin Dilute acid
Solanine Acetic acid
Terms to remember
4) Indigenous plants – plants growing in their
native country

5) Naturalized plants – plants growing in a

foreign land or locality OTHER THAN their
native source
PREPARATION OF CRUDE DRUGS
COLLECTION

HARVESTING

DRYING

CURING

GARBLING

PACKAGING, STORAGE AND PRESERVATION

COLLECTION
 Small-scale
 Select the species to cultivate
 Best time to collect?  when the
constituents of the certain plant part are
in their highest content
PECTIN – OBTAINED FROM RIND OF CITRUS FRUITS
Unripe fruit Protopectin
Just ripe Pectin
Overripe Pectic acid
MARIJUANA
Young leaves Cannabidiol
Mature leaves Cannabinol
COLLECTION TIMES
 Root crops – when the overground
parts are withering
 Flower – morning, when the flower
just bloomed
 Bark – between summer and spring
HARVESTING
 Large-scale
 Use of mechanical devices or manual
labor

DRYING
 Most important step
 Removes moisture content to prevent
microbial growth and enzymatic degradation

CURING
 Special drying process
 Enhances the property of the active
ingredient
GARBLING
 Final
step
 Removal of extraneous materials

PACKAGING, STORAGE &

PRESERVATION
 For
protection and marketability of crude drugs
 Ways:
1) Simplest method: Expose drug to 65OC
2) Fumigation with CH3Br
3) Add a drop of CHCl3 or CCl4
Classification of drugs
1) Morphologic – plant part or animal
used
2) Taxonomic* – natural relationship
or phylogeny (zoologic/botanic)
3) Pharmacologic/Therapeutic –
therapeutic effect
4) Chemical – chemical class,
preferred method
Evaluation of drugs
 Purpose: determine quality and purity

1) Organoleptic – organs of sense, macro

2) Microscopic – micro, presence of adulterants
3) Biologic – pharmacologic activity, bioassay
4) Chemical – determine potency
5) Physical – physical constants
BIOASSAY
Drug Animal used
Digoxin Pigeon
Atropine Cat
Glucagon Cat
Oxytocin Chicken (F)
Tubocurarine Rabbit (1), Rats
(Head-drop crossover test)
PTH Dogs
Heparin Sheep
Insulin Rabbit
CHEMISTRY OF NATURAL DRUG
PRODUCTS
1) Pharmaceutically-active – cause chemical
changes in the PREPARATION
2) Pharmacologically-active – responsible for
the THERAPEUTIC EFFECT
3) Inert constituents – NO DEFINITE
pharmacologic activity
4) Secondary plant substance – EXTRACTED,
CRYSTALLIZED AND PURIFIED
NEW FAMILY NAMES
OLD NEW MNEMONIC
Compositae Asteraceae COMP-AS
Cruciferacea Brassicaceae CRU-BRA
Graminae Poaceae GRA-PO
Guttiferae Clusiceae GUTT-CLUS
Umbelliferae Apiaceae UM-API
Labiatae Lamiaceae LA-LA
Palmae Arecaceae PAL-ARE
MINI-QUIZ
 Animal used for the bioassay of PTH
 Final step in the preparation of crude drugs
 Simplest method of preservation of crude drugs
 Plant part used to obtain cannabinol
 New name of the family Palmae
 Special drying process
 Undergone only the process the collection and
drying
 Solvent for extraction of fats
 Coined the term pharmacognosy
 Made clay models of the human body
BIOGENESIS/ Drug biosynthesis
 Theprocess of producing secondary
metabolites

Process:
1Ometabolite  2Ometabolite
Carbohydrates  Glycosides
Proteins  Tannins
Fats  Essences or Fixed oils

Influenced by: HOE

HOE
 Heredity
 Mentha arvensis vs M. piperita
 Ontogeny/Stage dev’t
 Young MJ vs Mature MJ
 Environment
Domesticated Catharanthus (Pink,
White, Yellow) vs Wild
Catharanthus (Purple)
 OVERVIEW
Carbohydrates
Gums, Mucilages and Plant extractives
Glycosides
Tannins
Lipids
Volatile oils
Resins
Alkaloids
CARBOHYDRATES
 Most abundant group of organic
molecules in nature
 First products of photosynthesis
 Also called polyhydroxyketones or
polyhydroxyaldehydes

 Empiric formula: (CH2O)n

Functions
 Provide significant amount of energy
(e.g. glucose)
 Serve as storage form of energy in the
body (e.g. starch and glycogen)
 Cell components (e.g. glycoproteins)
 Structural components (e.g. chitin)
CARBOHYDRATES
Monosaccharides
Disaccharides
Oligosaccharides
Polysaccharides
MONOSACCHARIDES*
 Simplest
carbohydrate unit
 Cannot be hydrolyzed to simpler sugars

No. of Carbon units General Name

2 Diose
3 Triose
4 Tetrose
5 Pentose
6 Hexose
7 Heptose
8 Octose
9 Nonose
PENTOSE
SUGAR DESCRIPTION
RIBOSE Product of gum hydrolysis
XYLOSE “Wood sugar” Simplest sugar found in
plants but not in free form
(as xylan polymer)

Can be obtained from

hydrolysis of xylan in corn
cobs and straw w/ dilute
acid

Diagnostic aid for intestinal

malabsorption and cystic
fibrosis
HEXOSE – most important
SUGAR DESCRIPTION
Glucose B-D-glucose – most abundant
Dextrose form in nature, structural Body
Grape sugar polysaccharide as in cellulose
Physiologic sugar
Blood sugar a-D-glucose – storAge
polysaccharide as in starch

Obtained from controlled

hydrolysis of starch

Used as nutrient given by

mouth, by enema, by SC or IV
HEXOSE
SUGAR DESCRIPTION
Fructose Sweetest monosaccharide
Levulose w/ bitter aftertaste
Fruit sugar
From inversion of aqueous
sucrose solution and
hydrolysis of inulin
Galactose C4 epimer of glucose

Found in milk as lactose and

in neuronal fibers as
galactosides
DISACCHARIDES
 Composed of two monosaccharides
linked a glycosidic bond

A glycosidic bond is an ether bond

(COC)
DISACCHARIDES
DISACCHARIDE Composition Linkage
Trehalose Glu-Glu a-1,1
Sucrose Glu-Fru a-1,2
Maltose Glu-Glu a-1,4
Lactose Gal-Glu B-1,4
Lactulose Gal-Fru B-1,4
Sophorose Glu-Glu B-1,2
Cellobiose Glu-Glu B-1,4
DISACCHARIDES
SUGAR DESCRIPTION
Sucrose Only disaccharide that
Saccharum occurs free in nature
Cane sugar
Beet sugar Non-reducing sugar
Table sugar

Official sources: Uses:

Beet - Used in the manuf of
(Beta vulgaris) syrup
Sugar cane - Nutrient
(Saccharum officinarum) - At 85% = bacteriostatic
Sugar maple (self-preserving)
(Acer saccharum) - Masks disagreeable taste
How to obtain sucrose?
DISACCHARIDES
SUGAR DESCRIPTION
Maltose From germination of barley
Malt sugar
Lactose Source: Cow’s milk (Bos
Milk sugar taurus)

Uses: Tablet diluent, infant

feeding  important to
establish intestinal flora
MILK PRODUCTS
 Butter: formed when fat globules unite
 Buttermilk: liquid left after fat globules unite
 Skimmed milk: milk left after separation of cream
 Coagulum: formed when skimmed milk is treated
with RENNIN
 Cheese: treated coagulum
 Condensed milk: formed by partial evaporation
of milk in a vacuum with consequent sterilization
in a hermetically-sealed container by autoclaving
 Malted milk: evaporation of milk with malt extract
 Kumyss: fermented milk
DISACCHARIDES
SUGAR DESCRIPTION
Lactulose Semisynthetic sugar
Brand: Duphalac, Lilac
Alkaline rearrangement of
lactose

Used as laxative to reduce

straining of defecation for MI
patients

MOA: Metabolized by
colonic flora to lactic acid
and acetic acid
OLIGOSACCHARIDES
 Composed of 3-10 monosaccharides
SUGAR DESCRIPTION

Dextrin Several glucose units

Browning of bread

Maltotriose Glu-Glu-Glu

Melitriose/Melitose/Raffinose Glu-Fru-Gal

Gentianose/Melezitose Glu-Glu-Fru
TERMS TO REMEMBER:
Products of Starch Hydroylsis
 Liquid glucose - INCOMPLETE product of starch
hydrolysis
 Dextrin - PARTIAL product of starch hydrolysis
 Maltotriose - INTERMEDIATE product of starch
hydrolysis
 Maltose - COMPLETE OR MAJOR product of starch
hydrolysis
POLYSACCHARIDES
 Aka“Glycans”
 More than 10 monosaccharide units
 complete, high MW polymers of
monosaccharides linked by GLYCOSIDIC
BONDS

 Can be:
 Homoglycan/Homopolysaccharide
 Heteroglycan/Heteropolysaccharide
HOMOGLYCANS
 Composed of only ONE TYPE of monosaccharide
 Starch
 Glycogen
 Dextran
 Cellulose
 Inulin
 Chitin
STARCH
 Official sources:
Corn (Zea mays)
Potato (Solanum tuberosum)
Wheat (Triticum aestivum)
Rice (Oryza sativa)
Others: Arrowroot (Maranta arundinacea)

 Uses of starch
 Tabletfiller, binder and disintegrant
 Antidote for iodine poisoning (starch suspension)
 Permanent reserve food material in plants
STARCH
 Storagepolysaccharide in plants
 Glucosan

AMYLOSE AMYLOPECTIN
Linearity Linear, helical (a-1,4) Branched, every 25
to 30 units (a-1,4 and
a-1,6)

Solubility Insoluble in water Soluble in water

Size 250-300 units Above 1000 units

Iodine Dark blue Purple

STARCH PRODUCTS
 Starch paste – dispersed starch in cold water

 Pregelatinized
starch – all the granules have
been ruptured in the presence of water

 Na starch glycolate – semi-synthetic sodium

salt of carboxymethyl ether of starch;
disintegrant

 Hydroxyethylstarch/Hetastarch – water-soluble
starch with >90% amylopectin; plasma
expander (6% Hetastarch) in shock patients
GLYCOGEN
 Storage polysaccharide in animals
 Glucosan
 Linkage: a-1,4 and a-1,6

 More branched than starch (every 12-15 units)

 Stored in the liver (8-12 hr supply) and skeletal
muscles

 Glycogen storage diseases

Glycogen storage diseases
0 – Glycogen synthase deficiency
Ia (Von Gierke) – Glucose-6-phosphatase deficiency
Ib – Glu-6-Phosphate ER transporter deficiency
II (Pompe’s) – Lysosomal α-1,4 & 1,6 glucosidase deficiency
IIIa (Forbes-Cori) – Liver & muscle debranching enzyme deficiency
IIIb (Limit dextrinosis) – liver debranching enzyme deficiency
IV (Andersen/Amylopectinosis) – branching enzyme deficiency
V (McArdle) – Muscle phosphorylase deficiency
VI (Hers) – Liver phosphorylase deficiency
VII (Tarui) – Muscle & Erythrocyte PFK-1 deficiency
VIII – Liver phosphorylase kinase deficiency
IX – Liver and muscle phosphorylase kinase deficiency
XI (Fanconi-Bickel syndrome) – GLUT 2 deficiency
DEXTRAN
 Glucosan
 a-1,6and a-1,3 bonds
 Plasma expander in shock patients
 Obtained through:

 Glucose as primer
 Dextran sucrase aka transglucosylase enzyme
CELLULOSE
 Structural
polysaccharide in plants
 Chief constituent in cell walls
 Glucosan
 B-1,4 bonds
CELLULOSE PRODUCTS
 Purified cotton – from the hair of the
seeds of Gossypium hirsutum, used
as surgical dressing
 Powdered cellulose – mechanically
disintegrated a-cellulose
 Microcrystalline cellulose – purified,
partially depolymerized a-cellulose
 Purified rayon – bleached,
regenerated cellulose w/ nmt 1.25%
of Titanium dioxide
CELLULOSE DERIVATIVES
 Methylcellulose – suspending agent, protectant in
artificial tears
 Ethylcellulose – tablet binder, film coating
 Hydroxyethylcellulose – thickener, ingredient in
artificial tears
 HPMC – ingredient in artificial tears, suspending
agent
 Pyroxylin/Cellulose trinitrate/Soluble guncotton –
made by the action of nitric and sulfuric acid on
cellulose, used in collodion
 Oxidized cellulose – local hemostatic
 CAP – tablet coating
 Na CMC – suspending agent, bulk laxative
INULIN
 Fructosan
 Linkage: B-2,1 bonds
 Obtained from the cell sap of the
underground organs of the plants in the
family Compositae (Asteraceae)

 Improves digestion
 Used as diagnostic agent to estimate GFR
since it is neither secreted nor reabsorbed
CHITIN
 Exoskeleton of mollusks and arthropods
and fungi
 Homoglycan of N-acetylglucosamide
HETEROGLYCAN
 Morethan one monosaccharide present
upon hydrolysis
 Hyaluronic acid – vitreous humour, synovial
fluid
 Chondroitin sulfate – cartilages, tendons,
ligaments
 Dermatan sulfate – skin
 Keratan sulfate – nail
 Heparan/Heparin sulfate - Anticoagulant
Drugs metabolically related
to carbohydrates (aldoses)
OXIDATION OF ALDOSES
NOMENCLATURE
 At the Aldehyde group = Aldonic acids
 At the Terminal Alcohol group = Uronic
acids
 At both aldehyde and terminal alcohol
groups = Aldaric acids

 Example: Glucose
Cherry juice
 From the fresh ripe cherry fruits (Prunus
cerasi)
 >1% Malic acid
 Used to prepare cherry syrup
PLANT ACIDS
 Citric acid – Tricarboxylic acid discovered
from lemon juice by Scheele
 Tartaric acid- Dicarboxylic acid and
byproduct of wine industry
 Lactic acid – from lactic fermentation of
sugars and acidulant in infant feeding
formula

 Test to differentiate Citric and Tartaric: ____

ALCOHOLS
> 92.3% by weight or 94.9% by volume
ethanol at 15.56OC
 Obtained via fermentation and distillation
 70% w/v – local anti-infective
 Diluted alcohol – 48.4 to 49.5% by volume
at 15.56OC, solvent
ALCOHOL PRODUCTS
 Brandy – distillation of wine
 Whiskey - distillation of fermented malted grain
 Rum – distillation of fermented molasses
 D-mannitol – from manna, dried saccharine
exudate of Fraxinus ornus; used to estimate GFR;
osmotic diuretic
 Sorbitol/D-glucitol – from the berries of mountain
ash, Sorbus aucuparia; half as sweet as sucrose;
humectant
 Galactitol/Dulcitol – reduction product of
galactose
Mini-quiz
 Also known as Physiologic sugar
 Fermented milk
 True or False. Sorbtiol is twice as sweet as sucrose.
 Used to decolorize brown sucrose
 Found in the exoskeleton of mollusks and
arthropods
 Enzyme employed to convert sucrose to dextran
 True or False. Amylopectin is branched and
insoluble in water.
 General test for carbohydrates
 Formed when fat globules unite
 Tacky proteins that may impede the flow of starch
 OVERVIEW
Carbohydrates
Gums, Mucilages and plant extractives
Glycosides
Tannins
Lipids
Volatile oils
Resins
Alkaloids
GUMS AND MUCILAGES
 natural plant hydrocolloids that maybe
classified as anionic or non-ionic

 Appears as translucent and amorphous

 Upon hydrolysis, they yield arabinose,

galactose, glucose, mannose, xylose and
other uronic acid derivatives.
GUMS AND MUCILAGES
General uses:

 Ingredient in dental and other

adhesives
 Bulk laxatives
 Pharmaceutic necessity
GUMS AND MUCILAGES
Shrubor Tree exudates
Marine gums
Seed gums
Microbial gums
SHRUB OR TREE EXUDATES
PLANT Scientific name
Tragacanth Astragalus gummifer

Acacia/Gum Acacia senegal

arabic/Egyptian
gum

Ghatti/Indian Anogiessus latifolia

gum
Karaya/Sterculia Sterculia urens
gum
SHRUB OR TREE EXUDATES
PLANT Active constituent USES/COMMENTS
Tragacanth* 66% Bassorin (swells) Suspending agent at
34% Tragacanthin 5-6%, emulsifier, best
(non-gelling; thickener) mucilage (resistant
to acid h ydrolysis)
Acacia/Gum Arabin Stable below 60%
arabic/Egyptian gum alcohol, contains 12-
15% water,
suspending agent at
35-38%
Ghatti/Indian gum - Acacia substitute
Karaya/Sterculia gum D-galacturonic acid Laxative, suspending
D-glucuronic acid agent, has fetid
(fecal) odor
MARINE GUMS
PLANT Scientific name

Algin/Sodium alginate Macrocystis pyrifera

Agar/Japanese isinglas Gelidium cartilagineum

Gracilaria confervoides

Carageenan/ Chondrus crispus

Chondrus/Irish moss Gigartina mamillosa

Danish agar/Furcellaran Furcellaria fastigiata

G. cartilagenium
M. pyrifera
MARINE GUMS
PLANT Active constituent USES/COMMENTS
Algin/Sodium alginate D-mannuronic acid Suspending
agent, tablet
binder
Agar/Japanese Agarose* Laxative, tablet
isinglas Agaropectin* diluent, solidifying
agent in culture
media
Carageenan/ Carageenan forms: Demulcent, bulk
Chondrus/Irish moss laxative
Κ & ι – gelating

λ - non-gelling, thickener

Danish Similar to k-carageenan Suspending agent

agar/Furcellaran
SEED GUMS
PLANT Scientific name
Plantago Spanish: Plantago psyllium
seed/Psyllium/Plantain
seed Indian: Plantago ovata

Cydonium/Quince seed Cydonia vulgaris

Guar gum/Guaran Cyamopsis tetragonolobus

Locust bean gum/Carob Ceratonia siliqua

pulp/St. John’s bread
C. siliqua
SEED GUMS
PLANT Active constituent USES/COMMENTS
Plantago - Ripe seed coat is
seed/Psyllium/ used as bulk-
Plantain seed forming laxative
(MOA: gum in the
seed swells)
Cydonium/Quince L-arabinose Thixotropic
seed Aldobiouronic acid hydrocolloid in
lotions
Guar gum/Guaran Galactomannan Bulk laxative,
thickener,
disintegrant
Locust bean Galactomannan Chocolate
gum/Carob pulp/ substitute,
St. John’s bread thickener
MICROBIAL GUMS
Gum Microbe employed
Xanthan gum Xanthomonas campestris

Dextran gum Leuconostoc mesenteroides

MICROBIAL GUMS
Gum USES/COMMENTS
Xanthan gum High MW gum from the action
of X. campestris on a suitable
carbohydrate

Pseudoplastic/Shear-thinning
flow – allows toothpastes and
ointments to hold shape and
spread readily

Dextran gum Plasma expander

PLANT EXTRACTIVES: PECTIN
 Intercellular
cementing material
 Obtained from the dilute acid extract of
the inner portion of the rind of citrus fruits
or pomace
 Contains a partially methoxylated
galacturonic acid – has swelling property
PECTIN SOURCES
PLANT SCIENTIFIC NAME*
Pomelo ?
Orange ?
Dalanghita ?
Ponkan ?
Kalamansi ?
Grapefruit ?
Lemon ?
Apple pomace ?
PECTIN USE/S
 Kaopectate© (Kaolin + Pectin) – used
before as an anti-diarrheal
Types of Pectin
PHARMACEUTIC COMMERCIAL
PECTIN PECTIN
Pure pectin Contains added
substances like
sugars or organic
acids
Mini-quiz
 Scientific name of Dalanghita
 Non-gelling component of carageenan
 Similar to k-carageenan
 Best-grade tragacanth
 True or false. Agarose contains a higher
sulfate content than agaropectin
 Active constituent of Acacia
 Chocolate substitute
 Japanese isinglas
 Percentage of acacia used as suspending
agent
 Plant part used to obtain pectin
 OVERVIEW
Carbohydrates
Gums, Mucilages and plant extractives
Glycosides
Tannins
Lipids
Volatile oils
Resins
Alkaloids
GLYCOSIDES
 Plant constituents which produce sugars
as products of hydrolysis
 “Sugar ethers”
 Regulatory, protective and sanitary
compounds

 Betaform – most common

 Alpha form – less common
2 COMPONENTS
GLYCOSIDES
 Cardiac glycosides
 Anthraquinone glycosides
 Saponins
 Cyanophore glycosides
 Isothiocyanate glycosides
 Flavonol glycosides
 Alcohol glycosides
 Aldehyde glycosides
 Phenol glycosides
 Lactone glycosides
Cardiac glycosides

 Exert
action on cardiac muscle
 MOA: Inhibits Na+/K+ ATPase pump
 Increased intracellular Na+
 Reduction of Ca2+ expulsion

 (+) inotropic = ↑ cardiac contractility

 (-) chronotropic= ↓ heart rate
TYPES OF CARDIAC GLYCOSIDES
Cardenolide Bufadienolide

More common Less common, from

toad (Bufo spp.)skin

Optimum activity Less activity

C23, 5-membered C24, 6-membered

lactone ring lactone ring
Tests for cardiac glycosides
 Aglycone portion: Unsaturated steroidal
nucleus
– tested by Libermann-Burchard and
Salkowski tests

 Glycone portion: 2-deoxy sugar fx group

– tested by Keller Killiani test
PLANT ORIGIN AC COMMENTS

Grecian foxglove Digitalis lanata Digoxin – water soluble, less toxic

Digitoxin – lipid-soluble, more toxic
Foxglove Digitalis Desacetyl-lanatoside (Deslanoside) –
purpurea for rapid initial loading (digitalization)
Convallaria/ Convallaria Convallatoxin
Lily of the Valley majalis

Adonis/ Adonis vernalis Adonitoxin

Pheasant’s eye

Strophanthus Strophanthus K-strophanthin

kombe G-strophantin (ouabain) – toxic form

Apocynum/ Apocynum Cymarin

Black Indian hemp/ cannabinum
Dog Bane/
Cannadian hemp
D. lanata C. majalis
 ORIGIN AC COMMENTS

Oleander/ Nerium oleander Oleandrin

Adelfa/
Rose bay/

Squill/ Urginea maritima Should not contain the red moiety (very
Mediterranean or toxic)
White Squill
Scillarenin – only bufadienolide
Cactus Selenicereus
grandiflorus/ grandiflorus
Night blooming
cereus

Black hellebore/ Helleborus niger Hellebrin – cardiac stimulant

Christmas rose
***White & Green Hellebore – cardiac
depressant
H. niger
Anthraquinone glycosides
 Commonly employed as cathartics
except chrysarobin

 Aglycone portion: Anthracene

 Color
of anthraquinone derivatives:
orange

 ID Test: Bornträger test

PLANT ORIGIN ACTIVE CONSTITUENT/COMMENTS

Cascara Rhamnus purshianus Cascarosides A,B – optical isomers of

sagrada/ barbaloin
Sacred bark Cascarosides C,D – optical isomers of
chrysaloin

Lane’s Pill – contains casanthrol

(purified mixture of anthranol
glycosides)

Frangula Rhamnus frangula Movicol© - Karaya + Frangula

Buckthorn bark (Cathartic)

Aloe (dried Curacao – A. Barbaloin – chief cathartic

latex juice of barbadensis, A. vera
leaves) Aloe-emodin (O-glycoside)
Cape – A. spicata, A. Aloin (C-glycoside)
ferox

Other uses: emollient, tx for burns

(2%)
R. pushianus
PLANT ORIGIN ACTIVE CONSTITUENT/COMMENTS

Rhubarb (dried Chinese- Rheum Rhein anthrones

rhizome or root) officinale, R.
palmatum

Indian/Himalayan –
R. emodi, R.
webbianum

Senna (dried Tinnevelly – Cassia Tinnevelly – full leaves are used

leaflets) angustifolia
Alexandria – broken leaves are used
Alexandria – C.
acutifolia Sennosides A and B

More potent than cascara

Chrysarobin Powder obtain from Not cathartic but a keratolytic when

Andira araroba dissolved in benzene
C. angustifolia
SAPONINS
 Soap-like, foams upon shaking
 Steroidal in nature (CPPP)
 Sternutatory (irritating to mucous membranes)

 Aglycone portion: Sapogenin

 Neutral – with spiroketal side chains
 Acid – with triterpenoid structures
 Toxic: Sapotoxin
SAPONINS
 Readily crystallizes upon acetylation

 Precursor of steroidal hormones like

cortisone

 Destroy RBCs of cold-blooded animals

(fish poison)
 (+) B hemolysis
Complete partial none
TESTS FOR SAPONINS
 Froth test – persists for 10 minutes

 Keller-killiani – reddish brown

 Libermann-Burchard- blue-green
PLANT ORIGIN ACTIVE CONSTITUENT/COMMENTS

Glycyrrhiza/ Glycrrhiza glabra Glycyrrhizin/Glycyrrhic acid –

Licorice root 50x as sweet as sugar, can mask
Quinine’s bitterness

Uses: Sweetener, anti-

inflammatory for PUD

CI: CHF and HTN (Na & Water

retention)
Dioscorea Dioscorea floribunda Diosgenin – precursor for steroid
Mexican Yam (best source) synthesis
Ginseng American: Panax Panaxosides, Ginsenosides,
quinquefolius Chikusetsusaponins
- Fave remedy
in Chinese
Asian: Panax Uses: Aphrodisiac, adaptogen
medicine
ginseng (anti-stress)
G. glabra
CYANOPHORE GLYCOSIDES
 Cyanogenic – produces cyanide upon
hydrolysis
 Found in Rosaceae plants
 Cyanide-containing compounds: Prunasin,
Laetrile/Vit B17 and Amygdalin

 Amygdalin – most common

 Emulsin – composite enzyme composed of
Amygdalase and Prunase

 ID Test: Guignard test/Prussic acid test

(+) = various shades of red
/ PRUNASIN

Benzaldehyde – responsible
for flavor and odor

HCN - toxic
Sources

Wild cherry (Prunus serotina)

Apricot (P. armeniaca)
Almond (P. amygdalus)
ISOTHIOCYANATE GLYCOSIDES
 Aka Glucosinolates or Mustard glycosides
 Found in cruciferous plants (Brassicaceae)
Brassica spp.
FLAVONOL GLYCOSIDES
 Aglycone portion: flavonoid

 Yellow pigments – rutin and

quercetin
 Citrus bioflavonoids (tx symptoms of
common colds) – hesperidin,
hesperitin, diosmin, naringen
 Vitamin P (Permeability factor) –
Rutin + Hesperidin
 Treat capillary bleeding and fragility
Sources of flavonol glycosides
 Elm (Ulmus spp.) – quercetin

 Buckwheat plant (Fagopyrum esculentum) –

Rutin

 Milk thistle (Silybium marianum) – silibinin,

silymarin (hepatoprotective)

 Ginkgo(G. biloba) – ginkgolides and bilolabides

(memory enhancement)
ALCOHOL GLYCOSIDES
 Salicin
 Source: Willow bark (Salix purpurea, S.
fragilis)
 Use: Antirheumatic, anti-inflammatory
same as salicylic acid
 Hydrolyzed to Saligenin (Salicyl
alcohol) and D-glucose by Emulsin
 Populin
 Source: Poplar bark (Populus spp.)
S. purpurea
ALDEHYDE GLYCOSIDES
 Vanilla
 Source: Vanilla plantifolia
 AC: Vanillin (4-hydroxy-3-methoxybenzaldehyde or
methylprocatechuic aldehyde)
 Semi-synthesized from:
 coniferin (pine tree)
 eugenol (clove)
 lignin (by product of pulp industry)
 Use: Flavorant
VANILLA
 Other info
 MEXICAN OR VERA CRUZ VANILLA – best-
grade
 BOURBON VANILLA –blacker, with coumarin
odor
 TAHITI AND HAWAII VANILLA – red-brown,
unpleasant odor, less suitable for flavoring
 GREEN VANILLA (inactive form)- composed
of glucovanillin (avenein) and glucovanillic
alcohol, when hydrolyzed yields vanillin
PHENOL GLYCOSIDES
 Uva-ursi/Bearberry
 Source: Arctostaphylos uva-ursi
 AC: Arbutin/Ursin (antiseptic and astringent)
 Other uses: Mild diuretic (present in teas)
 Poison ivy and oak
 Source: Ivy – Rhus radicans
Oak – R. toxicodendron
 AC: Uroshiol – caues delayed contact dermatitis
 Other phenol glycosides:
 Hesperidin (also a flavonol glycoside)
 Phloridzin (from root bark of rosaceous plants)
 Baptisin (from Baptisia)
 Iridin (from Iris spp.)
LACTONE GLYCOSIDES
 Coumarin
 Fragrant odor, bitter aromatic and burning
taste
 AC: bishydroxycoumarin/dicumarol
 Sources:
 Tonka beans (Dipteryx odorata)
 Sweet vernal grass (Anthoxanthum
odoratum)
 Sweet clover (Melilotus albus, M. officinalis)
 Sweet-scented bedstraw (Galium triflorum)
 Red clover (Trifolium pratense)
 Use: Anticoagulant, precursor of Warfarin
LACTONE GLYCOSIDES

 Cantharides
 Source: Cantharis vesicatoria (Russian flies,
blistering flies, spanish flies) – mature insects
with green metallic luster
 AC: Cantharidin
 Preparation: insects are killed with fumes of hot
vinegar, NH3 or CHCl3
 Uses: Irritant, Vesicant, Aphrodisiac, Wart-
removal
LACTONE GLYCOSIDES
 Psoralens
 Photosensitizing furocoumarins
 Source: Ammi majus (Bishop’s flower)
 Methoxsalen/Xanthotoxin/8-methoxypsoralen
– repigmentation in vitiligo
 Trioxsalen – synthetic furocoumarin
 Therapy requires cautious exposure to UV light
 Risks: Carcinogenesis, cataract, actinic
degradation of skin (thickened, dry skin)
Other lactone glycosides

 Santonin (from Artemisia cina)

 Use: Anthelmintic
 Scopoletin(from Blackhaw, Viburnum
prunifolium)
 Use: Antispasmodic
 OVERVIEW
Carbohydrates
Gums, Mucilages and plant extractives
Glycosides
Tannins
Lipids
Volatile oils
Resins
Alkaloids
TANNINS
 Group of complex phenolic compounds
capable of combining with proteins
 Has acidic, puckering taste
 Difficult to separate because they do
not crystallize
 Precipitate proteins, alkaloids and
glycosides
 Medicinal use: Astringent
 Industrial use: Manufacture of leather
from animal hides
TANNINS
Found in universal antidote
 1 Tannic acid: 2 Activated charcoal : 1 MgO

Carcinogenicpotential (oral and

esophageal cancer)
 Chewing of betel nut (Areca catechu)
 Tea (Camelia sinensis) without milk
Danish (higher incidence) vs British
(lesser)
CLASSES OF TANNINS

PHLOBAPHENES
 Origin Active constituent Use
Hamamelis Hamamelis Hamamelitannin Astringent
leaf/ virginiana Hemostatic
Witch Hazel Incorporated in
leaf anti-
hemorrhoidal
preparations
Nutgall Hardened Tannic Most important
excrescence from acid/Gallotannic source of tannic
the young twigs of acid acid, Astringent
Quercus infectoria Treatment of
when a Elagic acid + burns, Alkaloidal
hymenopterous Gallic acid = poisoning,
insect, Cynips Tannic acid topical
tinctoria bores holes application for
to deposit its ova bed sores and
minor wounds
Japanese Formed on Rhus Gallic acid/3,4,5- Bismuth
and chinensis by the trihydroxybenzoic subgallate –
Chinese stings of a plant lice, acid used to help
galls Aphis spp. control odors
Q. infectoria
TEST FOR TANNINS
 Gelatin test
 (+) = precipitation of proteins
 Goldbeater test
 (+) = Brown or black ppt
TEST FOR TANNINS
 Phenazone test
 (+) – bulky colored ppt
Mini-quiz
 Digitalis lanata
 True or false. Cascara is more potent than Senna.
 Used for repigmentation in vitiligo
 Other name of vanillin
 ID test for Anthraquinone glycoside
 Official source of Silymarin
 50x as sweet as sugar
 General use of anthraquinone glycoside
 Destroy RBCs of cold-blooded animals
 Test for Cyanogenic glycosides
 Solvents used for cantharidin preparation
 Other name of uva-ursi
 Leather produced by hydrolyzable tannin
 Polymerization product of condensed tannins
 Color produced by hydrolyzable tannins with FeCl3
 Most common medicinal use of tannins
 OVERVIEW
Carbohydrates
Gums, Mucilages and plant extractives
Glycosides
Tannins
Lipids
Volatile oils
Resins
Alkaloids
LIPIDS
 Estersof long-chain fatty acids and
alcohols or closely related
derivatives
 Also called Lipins or Lipoids
 Can be fixed oils, fats and waxes
Fixed oils vs Fats vs Waxes
Fixed oils Fats Waxes
Description Ester of FA and glycerol Ester of FA
and High MW
monohydric
alcohol
Physical Liquid at RT Solid at RT Solid or semi-
state except exept Cod solid
Myristica and liver oil except
Theobroma oil Jojoba oil
Composition Mainly Mainly -
Unsaturated FA Saturated FA
Source From plants From animals From plants
and animals
Function Energy storage Protection
Some USP tests for Lipids
Acid value or Acid number - mg of KOH required to
NEUTRALIZE free FAs in 1g of sample

Saponification value or Kὅettsdorfer number - mg of

KOH needed to NEUTRALIZE the free FAs and SAPONIFY
the esters in 1g of sample

Iodine value - g of iodine absorbed under prescribed

conditions by 100g of sample

Ester value – mg of KOH needed to saponify 1g of FA

LIPID EXTRACTION
 Expression
 Rendering
 Solvent extraction
EXPRESSION
 Uses
hydraulic process, usually for
vegetable sources

 Types:
 Cold-pressed oil: carried out in the
cold, produces virgin oils
 Hot-pressed oil: carried out in the heat
RENDERING
 Usuallyfor fats
 Process:
 Steamed with or without pressure
 Fats melts and rises to the top
 Separation by decantation
 Clarified by filtration
 Bleached with ozone
 Stearins are removed by winter-chilling and
filtration
Solvent extraction
 Extraction
of fats using hexane or
petroleum ether
Drying, semidrying & non-drying oils
• Based on the ability of the lipid to absorb
oxygen
• Oxygen saturates the double bonds to form
oxides that may polymerize to form hard films

Iodine Value Range Examples

Non-drying <100 Peanut, almond,
olive
Semidrying 100-120 Cottonseed, sesame,
corn
Drying >120 Linseed, Cod liver
REACTIONS WITH LIPIDS
 Hydrogenation
 Liquid oils  semisolid fats
 Done by passing H2 in the presence of Ni or Pd
through the oil heated at 160-200OC
 Sulfation
 Reacting with sulfuric acid
 Temperature kept down by chilling
 Produces sulfated or sulfonated oils – used as
surfactants
General uses of Lipids
 Emollient
 Lubricant laxatives as emulsions
 Vehicles for other medicaments
 Manufacture of soaps
 Parenteral nutrient in TPN
SATURATED FA
 Acetic -2
 Butyric - 4
 Valeric - 5
 Caproic - 6
 Caprylic - 8
 Capric - 10
 Lauric -12
 Myristic - 14
 Palmitic – 16 – Most abundant FA
 Stearic - 18
 Arachidic - 20
UNSATURATED FA
SYMBOL # OF C / Lipid Double bond
# OF position
DOUBLE
BONDS

ω7 16:1 Palmitoleic 9
ω9 18:1 Oleic 9
ω6 Dietary precursor 18:2 Linoleic 9, 12
of PGE (Vit. F)

ω3 18:3 Linolenic α- 9, 12 ,15

ω6 (Vit. F) γ – 6, 9, 12
ω6 Precursor of PGE 20:4 Arachidonic 5, 8, 11, 14
ω3 20:5 Timnodonic 5, 8, 11, 14, 17
ω3 22:6 Cervonic 4, 7, 10, 13,
16, 19
LIPIDS: FATTY ACIDS
 Sodium morrhuate
 Source: Fatty acids from Atlantic cod, Gadus morhua
 Use: Sclerosing agent for varicose veins

 Azelaic acid
 Source: Ozonolysis of castor oil, Ricinus communis
 Use: Anti-acne
LIPIDS:FIXED OILS
Fixed oil Source Active constituent/
Use/Comments

Castor oil Tangan-tangan, AC:

Ricinus communis Triricinolein –(lipase in duodenum) 
Ricinoleic acid (Stimulant cathartic)

Ricin – toxic principle

Ricinine - alkaloid
Olive oil/Sweet Olea europea AC: Oleic acid
oil/Oil of Europe Use: Pharmaceutic aid
Forms:

First grade virgin – less pressure

Second grade – more pressure
Technical grade – hot water
Sulfur grade – CS2, inferior quality
Tournant oil – decomposing, high FA
Olea europea
LIPIDS:FIXED OILS
Fixed oil Source Active constituent/
Use/Comments

Peanut oil/Arachis Arachis hypogea AC: 75% Oleic acid, 25% Linoleic
oil
Use: Solvent for IM injection, nutritive
Sesame oil/Teel Linga, Sesamum AC: Oleic acid, Linoleic acid
oil/Benne oil indicum
Sesamolin –(hydrolysis) Sesamol
(stability)

Use: Solvent for IM injection, nutritive

Corn oil Zea mays AC: Linoleic acid, oleic acid

Use: Solvent for IM injection, nutritive

Cottonseed oil Gossypium AC: Linoleic, oleic, malvalic acid
hirsutum Use: Solvent for IM injection, nutritive

0.6% Gossypol – male sterility

LIPIDS:FIXED OILS
Source Active constituent/
Fixed oil Use/Comments

Soybean oil Glycine soja AC: Linoleic, Oleic

Use: Nutrient

Lecithin – used to control deranged

lipid metabolism

Stigmasterol – precursor of steroid

synthesis
Almond oil Prunus amygdalus AC: Oleic acid

Persic oil Apricot, Prunus AC: Oleic acid

armeniaca

Coconut oil Cocos nucifera AC: 80-85% Lauric and Myristic acid
 LIPIDS:FIXED OILS
Source Active constituent/
Fixed oil Use/Comments

Palm kernel oil Elaeis guineensis AC: Lauric and myristic acids

Safflower oil Carthamus tinctorius AC: Linoleic

Believed to be anit-lipemic (false
claim)
Sunflower oil Helianthus annuus AC: Linoleic, Oleic
Use: Alternative to corn or
safflower oil
Linseed oil / Linum usitatissimum AC: Linoleic acid
Flaxseed oil

Ethiodized oil Iodine addition product of the Use: Radiopaque, diagnostic aid
injection ethyl esters of FA from poppy
seed oil, Papaver somniferum

Hydrogenated Refined, bleached, hydrogenated and decolorized vegetable oil

vegetable oil
H. annuus
 LIPIDS:FIXED OILS
Source Active constituent/
Fixed oil Use/Comments

Theobroma oil Cacao seeds, Use: Food, beverage, pharmaceutic

Theobroma cacao aid, suppository base (as cocoa
butter)
AC: Oleopalmitostearin
Seeds
Roasted, nibbled
Cacao shells
winnowed
Kernels / “nibs”
ground
Cacao butter Congealed at RT
expressed
Marc + Some oil Bitter chocolate Sweet chocolate
powdered
Prepared cacao/Breakfast cacao Sugar, Vanilla
FOUR POLYMORPHS OF
THEOBROMA OIL/COCOA
BUTTER
 Same chemical but different melting
points
 Alpha – 17 degrees C
 Gamma – 23 degrees C
 Beta’ – 26 degrees C
 Beta stable – 34.5 degrees C (best)
FIXED OILS FOR IM INJECTION
Corn Oil
Cottonseed oil
Peanut oil
Sesame oil
TESTS FOR FIXED OILS
 Oliveoil: Millon’s Test (may be contaminated with
tea tree oil or camellia oil )

 Sesame Oil: Baudouin Test

 (+)pink color with fuming HCl and furfural

 Cottonseed oil: Halphen or Bevan Test

 Hydrogenated Vegetable Oil: Serger Test

FATS & RELATED COMPOUNDS
Fats Source Active constituent/
Use/Comments

Lanolin Purified fat-like Aka Hydrous Woolfat, contains 25-

substance from 30% water
sheep wool, Ovis
aries Use: Ointment base,
Anhydrous lanolin Aka woolfat, contains 0.25% water
Use: Water absorbable ointment base,
emollient
Cod liver oil Gadus morhua Liquid fat

Rich source of Vitamin A and D

Butterfat Bos taurus AC: Palmitic acid, Oleic acid

Lard Sus scrofa AC: Oleic, palmitic, stearic

Suet Bos taurus, Ovis AC: Oleic, palmitic, palmitoleic,

aries stearic
O. aries
G. morhua
S. scrofa
B. taurus
WAXES
Wax Source Active constituent/
Use/Comments

Spermaceti Physiologic product AC: Cetyl esters wax

of the head of
sperm whale, Use: Emollient, ingredient in creams
Physeter and ointments
macrocephalus
Beeswax From the Yellow wax – unbleached
honeycomb of bee, White wax – bleached
Apis mellifera
AC: Myricyl palmitate
Use: Ointment base
Jojoba oil Simmondsia AC: Esters of eicosenoic acid and
chinensis eicosenol, docosenol
Use: Emollient
Carnauba wax Copernicia AC: Myricyl cerotate
prunifera Use: In candles, wax varnish and
polishes, substitute for beeswax
SAPONIFICATION CLOUD TEST
 A rapid, reliable, and inexpensive method of detecting the
presence of certain adulterants of natural beeswax
Mini-quiz
 Oil of Europe
 Test for the purity of natural beeswax
 True of False. Jojoba oil is not a wax.
 The only liquid fat
 Scientific name for Soybean
 Substitute to corn oil
 Other name for anhydrous lanolin
 Other name for lanolin
 Main constituent of theobroma
 Oils that are produced via cold-press
 Most important dietary precursor of PGE
 Number of C of Valeric acid
 True or False. Coconut oil is used a solvent for IM injection.
 Other names for Sesame oil
 Confers stability of Sesame oil
 Toxic component in Cottonseed oil
 Test for hydrogenated vegetable oil