PHARMACOGNOSY AND PLANT CHEMISTRY

PCOG 211 (Lecture)

(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023

TANNINS
➢ ANSWER: Brown or Black (the
color of leather)
TANNINS - Goldbeater's skin test – Soak a
small piece of goldbeater's skin in
2% hydrochloric acid; rinse with
● Historically, tannin containing drugs are
distilled water and place in the
related to their tanning property i.e. their
solution to be tested for 5 min.
ability to transform fresh hides into
Wash with distilled water and
imputrescible leather.
transfer to a 1% solution of
● astringent; tannin precipitates proteins;
ferrous sulfate. A brown or black
related to polyphenol and flavonoids
color on the skin denotes the
● difficult to extract, don’t crystallize
presence of tannins.
- Goldbeater's skin is a membrane
TRADITIONAL APPLICATIONS OF
prepared from the intestine of
TANNINS
the ox and behaves similarly to
an untanned hide.
❖ Pharmacological and medicinal
-
Treatment of different affections:
gastrointestinal, respiratory, urinary, TRUE TANNINS
inflammatory, skin problems, sexual
diseases, etc. ❖ HYDROLYSABLE TANNINS
❖ Nutritional - These are ester of sugars and
- Food ingredients of different dishes, phenolic acid molecules
revitalizing agents and food - Trihydroxybenzoic acid
supplements, etc.
- resp. for tart flavor
❖ Veterinarian
- Animal feed, treatment of fever,
urinary, and gastrointestinal
disorders, parasites external
application on wounds, etc.

CLASSIFICATION OF TANNINS

★ True Tannins and Pseudotannins

★ THEY ARE BASED ON GOLDBEATER'S
(OX) SKIN TEST
- positive tanning test = true
tannin
- negative tanning test = pseudo
tannin
- Upon knowing the characteristic
of Tannins, what is the logical
positive result with Goldbeater's
Skin Test?
- Hydrolysable tanning on heating
with hydrochloric or sulphuric acids
yield – ELLAGIC ACID or GALLIC ACID
➢ Gallic Acid = Gallotannins
(Rhubarb, Gall, Clove)
➢ Ellagic Acid = Ellagitannins
(Pomegranate, Eucalyptus)
- Myrobalan (Terminalia chebula
Combretaceae)
- Bahera (Terminalia belerica
Combretaceae)
- Witch hazel (hamamelidaceae)

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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023
-on dry distillation are converted to
PYROGALLOL derivatives.
- The hydrolysable tannins are
soluble in water and their solution
produces blue color with ferric
chloride.
❖ CONDENSED TANNINS
- Proanthocyanidins
- Non-hydrolyzable
- They consist of flavan-3-ol units
linked together by carbon-carbon
bonds
- most often 4-8 or 4-6
- Condensed tannins occur due to
polymerization (condensation)
reactions between flavonoids.
- The polymers may include up to 50
monomer units of flavonoids
- On treatment with acids or enzymes
condensed tannins are converted
into red insoluble compounds
known as phlobaphenes.
➢ give the characteristic red color
to many drugs such as red
cinnamon bark.
- On dry distillation, they yield
CATECHOL derivatives.
- Condensed tannins are also soluble
in water and produce green color
with ferric chloride.
- General test for CONDENSED
TANNINS is the MATCH STICK TEST:
➢ A match stick is dipped in tannin
extract followed by HCI &
warmed near a flame it turns
pink in color
➢ Upon hydrolysis of the tannins
due to HCI, phloroglucinol is
formed which reacts with the
lignin of the wood to produce the
pink color.
PSEUDOTANNINS
● They are compounds of lower
molecular weight than true tannins
and they do not respond to the
goldbeater's skin test.
● Examples of drugs containing
Pseudotannins are:
- Gallic acid: Rhubarb
- Catechins: Guarana, Cocoa
- Chlorogenic acid: Mate, Coffee
- Ipecacuanhic acid: ipecacuanha
PROPERTIES OF TANNINS
❖ Tannins are soluble in water*, dilute
alkalis, alcohol, glycerol and acetone,
but generally only sparingly soluble in
other organic solvents.
❖ Solutions precipitate heavy metals,
alkaloids, glycosides and gelatin. (can
be used as an antidote for poisoning)
- Universal antidote – MgO, activated
charcoal, tannic acid
❖ Acts as preservatives because of its
antiseptic qualities
USES OF TANNINS
❖ Industrially; in leather tanning, ink
manufacture.
❖ Medicinally; astringent, haemostatic,
antidiarrheal, antidote in alkaloid and
heavy metals toxicity.
❖ In labs; reagent for detection of
proteins, alkaloids and heavy metals
because of their precipitating
properties.
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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023
EXAMPLE OF HYDROLYSABLE TANNINS
❖ WITCH HAZEL / HAZEL NUT / SNAPPING
NUT
- BIOLOGICAL SOURCE: leaves of
Hamamelis virginiana
- Family: Hamamelidaceae
- Uses:
➢ 1. astringent
➢ 2. It is incorporated in
hemorrhoidal products
➢3. Preparations for treating
insect bites and stings and even
teething preparations
- hamamelitannin
- Celeteque Toner (With Witch Hazel
Extract)
➢ What is the effect of Celeteque
Toner (with Witch Hazel Extract)
to skin upon application?
➢ ANSWER: It will make the pores of
the skin smaller, since Tannins
constrict the proteins present.
❖ NUTGALLS
- BIOLOGICAL SOURCE - obtained
from gall wasps Quercus infectoria
- Family: fagaceae
- WASP: Cynips tinctoria (Cynipdae)
- CONSTITUENTS
➢ The principal constituent is
tannic acid which is found to the
extent of 50-70%
➢ The drug also contains gallic
acid, 2 to 4% Ellagic acid, Starch,
Resin
- USE/S
➢ Nutgall, the chief source of tannic
acid is used in the tanning and in
the dying industry and, formerly
in the properties manufacture of
ink. Medicinally, It has astringent
EXAMPLE OF CONDENSED TANNINS
❖ BLACK CATECHU
- BIOLOGICAL SOURCE -. Heart wood
of Acacia catechu /Acacia chundra
- Family- leguminosae
- Uses: Astringents, treatment of
ulcers, diarrhea, & in tanning
industry.
ALLIED PRODUCTS
❖ Tannic Acid/Gallotannic Acid/Tannin
- a tannin usually obtained from
nutgall.
- The powdered galls are extracted
with a mixture of ether, alcohol,
and water and the liquid separates
into two layers.
➢ aqueous layer contains
gallotannin
➢ ethereal layer contains free
gallic acid.
- After separation, the solution of
gallotannin is evaporated and the
tannin is purified in various ways
- Composition – Tannic acid is not a
single homogenous compound but
is a mixture of esters of gallic acid
with glucose whose exact
composition varies according to its
source
- DESCRIPTION – Tannic acid occurs
as amorphous powder, glistening
scales, or spongy masses that are
light brown to yellowish white.
- USES – ASTRINGENT
- Chinese galls / Japanese galls
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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023

- Chinese galls – Rhus chinensis

(Anacardiaceae)
➢ Melaphis chinensis
(Pemphigidae) Aphids (plant
lice)

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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023

LIPIDS - Fatty or fixed oils are liquid at

normal room temperature except
BIOLOGICAL SIGNIFICANCE OF FATS cocoa butter (from plants but solid /
semi solid at room temp.
❖ Acts as fuel in the body (caloric value: - Fats are semi-solid or solid at
9kcals/gm) ordinary temperature expect cod
- Energy reservoir liver oil (from animal (fish) but liquid
❖ Deposits of fats underneath the skin that at room temp)
exerts insulating effects
❖ The mesenteric fat around organs
LIPID BIOSYNTHESIS
(kidney) acts as padding and
protecting internal organs
❖ Building materials
(cholesterol-hormone synthesis)

LIPIDS

● Consists of fixed oil, fats, and waxes

● Defined as esters of long chain fatty
acids and alcohols, or of closely related
derivatives
- Lipids are not classified based on
chemical structures. However, ★ Acetyl-COA acted upon Acetyl-COA
based on used carboxylase = Mantonyl-COA
- Alcohol in fats / lipids= Glycerol / ★ Mantonyl-COA + (enzyme:
Glycerin (3OH in structures) → can Mantonyl-COA: ACP acetyltransferase) =
undergo esterification to bind 3 fatty Mnatonyl-ACP
acid and form long chains ★ Enter Beta oxidation cycle
- Can be classified as fats (animals: ★ Lipid Biosynthesis is happened in
solid / semi solid at room temps.) endoplasmic reticulum (it used ATP)
and fixed oils (plants: liquid at room
temp.)
● Fats and fixed oils are obtained from
either plants (olive oil, peanut oil) or TYPES OF FATTY ACIDS
animals (lard)
SATURATED NO DOUBLE BOND

MONOUNSATURATED ONE DOUBLE BOND

POLYUNSATURATED MULTIPLE DOUBLE

BOND

● Their primary function if food (energy) ● Unsaturated Fatty Acid = Good Fats
storage ● Saturated Fatty Acid = Bad Fats
● Fixed oils and fats differs only as to
melting point

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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023

SATURATED FATTY ACIDS

❖ 5. Lauric
- Systematic Name: Dodecanoic
(12C)
- Formula: CH3(CH2)10COOH
- Common Source: Coconut and
Palm nut oils, butterfat
● SHORTHAND ❖ 6. Mystiric
● 8:0 - Systematic Name: Tetradecanoic
(14C)
-
Formula: CH3(CH2)12COOH
SATURATED FATTY ACIDS
-
Common Source: Coconut and
Palm nut oils, most animal and plant
fats
❖ 7. Palmitic
- Systematic Name: Hexadecanoic
(16C)
- Formula: CH3(CH2)14COOH
- Common Source: Practically all
animal and plant fats
● SHORT HAND ❖ 8. Stearic
● - 8:1 (Δ3) & 8:2 (Δ3,6) - Systematic Name: Octaadecanoic
(18C)
CLASSIFICATION OF FATTY ACIDS - Formula: CH3(CH2)16COOH
PRESENT AS GLYCERIDES IN FOOD FATS - Common Source: Animal fats and
minor component of plant fats
I. SATURATED FATTY ACIDS ❖ 9. Arachidic
(BuCaCaLaMyPaStAr) - Systematic Name: Eicosanoic (20C)
❖ 1. Butyric - Formula: CH3(CH2)18COOH
- Systematic Name: Butanoic (4C) - Common Source: Peanut oil
- Formula: CH3(CH2)2COOH
- Common Source: Butterfat II. UNSATURATED FATTY ACIDS
❖ 2. Caproic A. Monoethenoic Acid
- Systematic Name: Hexanoic (6C) ❖ 1. Oleic
- Formula: CH3(CH2)4COOH - Systemic Name: Cis
- Common Source: Butterfat, coconut, 9-octadecenoic (18C)
and palm nut oils - Formula: C17H33COOH
❖ 3. Caprylic - Common Source: plant and animal
- Systematic Name: Octanoic (8C) fats
- Formula: CH3(CH2)6COOH ❖ 2. Elaidic
- Common Source: Coconut and Palm - Systemic Name: Trans
nut oils, butterfat 9-octadecenoic (18C)
❖ 4. Capric - Formula: C17H33COOH
- Systematic Name: Decanoic (10C) - Common Source: animal fats
- Formula: CH3(CH2)8COOH - SHORTHAND – 18: 1 (Δ9)
- Common Source: Coconut and Palm
nut oils, butterfat

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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023

B. Diethenoic Acids ● Richest source of polyunsaturated fatty

❖ 3. Linoleic (Omega-6) acid
- Systemic Name: 9,12-octadecanoic - Vegetable oils: corn, sunflower,
(18 C) cottonseed oils
- Formula: C17H31COOH ● Omega rich foods – cold fish (salmon,
- Common Source: peanut, linseed, tuna)
and cottonseed oils
- SHORT HAND – 18: 2 (Δ9,12) EFA OMEGA 3 AND 6 FATTY ACIDS
❖ 4. Linolenic (Omega-3)
- Systemic Name: ❖ Omega indicated the position of the first
9,12,15-octadecatrienoic (18 C) double bond from the methyl group
- Formula: C17H29COOH ❖ The first point of unsaturation if next to
- Common Source: linseed and other the third carbon (omega 3 fatty acid)
seed oils ❖ The first point of unsaturation if next to
- SHORT HAND – 18: 3 (Δ9,12,15) the sixth carbon (omega 6 fatty acid)
❖ 5. Eleostearic ❖ Great significance on human nutrition
- Systemic Name: and health issues
9,11,13-octadecatrienoic (18 C)
- Formula: C17H29COOH IMPORTANCE OF LIPIDS
- Common Source: peanut seed oils
- SHORTHAND – 18: 3 (Δ9,11,13) ❖ Energy storage
❖ Signaling molecule
C. Tetraethenoid Acid (4 double ❖ Structural component of cell membrane
bonds)
PROPERTIES OF LIPIDS
❖ 6. Moroctic
- Systemic Name:
❖ Greasy
4,8,12,15-octadecatetraenoic (18 C)
❖ Lighter than water
- Formula: C17H27COOH
❖ Insoluble in water
- Common Source: fish oils
❖ Soluble in organic solvents
❖ 7. Arachidonic
❖
- Systemic Name:
5,8,11,14-eicosatetraenoic (20 C)
- Formula: C19H31COOH CHEMICAL PROPERTIES OF LIPIDS
- Common Source: traces in animal
fats
HYDROLYSIS - means addition
POLYUNSATURATED FATS (PUFA) of water.
Triglycerides
yield glycerol
● Two or more double bonds and fatty acid.
● Members of omega 3 and omega 6 EFA Opposite of
(essential fatty acid) esterification
- Linolenic acid (Omega 3 fatty acid) - Example:
- Linoleic acid (Omega 6 fatty acid) Triglycerides + 3
water → (lipase)

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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023

→ glycerol + 3 in 1 g of the
fatty acid substance
- Treatment of fatty
RANCIDITY - Initial products acids with bases
of oxidation are (e.g., potassium
aldehydes and hydroxide)
ketones. Final - Triglyceride +
products of 3KOH → (lipase) →
oxidation are glycerol + 3K salt
acid (RCOOH)
- The number of
ACROLEIN TEST - Presence of grams of Iodine
glycerol and absorbed, under
formation of prescribed
propenal conditions, by
100g of substance
indicated the
IODINE NUMBER degree of
unsaturation
- Higher iodine
number = more
TESTS FOR FIXED OILS
double bond
- Lower iodine
number =
- The number of saturated fatty
milligrams of acids
potassium
ACID VALUE hydroxide
OR required to
ACID NUMBER neutralize the free METHODS OF OBTAINING FIXED OILS OF
fatty acids in 1g of VEGETABLE AND ANIMAL ORIGIN
the substance
- Indicates the ❖ 1. Fixed oils and fats of vegetable origin
amount of free are obtained by expression in hydraulic
fatty acids present presses
in the oil - Virgin oil or a cold-pressed-oil if the
expression is carried out in cold
- The number of - Hot-pressed-oil if the expression is
milligrams of carried out in heat
potassium ❖ 2. Sometimes organic solvents are used
SAPONIFICATION hydroxide for extraction of oils
VALUE required to
neutralize the free
fatty acids and
saponify the
esters contained

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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023
CLASSES OF LIPIDS BASED ON ITS ABILITY
TO ABSORB OXYGEN FROM AIR
❖ Drying Oils – linseed oil, used for oil
base painting
❖ Semi Drying Oils – cottonseed and
sesame oil
❖ Non Drying Oils – olive and almond oil
SATURATED FIXED OILS
❖ COCONUT OILS
- Fixed oil obtained by expression of
extraction from the seed kernels of
the coconut palm, Cocos nucifera
- Consists of a mixture triacylglycerols
in which 80-85% of the acids are
saturated
- Coconut oil yield quality soaps and
shampoos
- Coconut oils has the highest
saponification value and lowest
iodine value among the common
fixed oils
- Semisolid at 20C
- Lauric and mystiric are the major
fatty acids. These low molecular
weight acids give the oil a high
saponification value and coconut oil
yields quality soaps and shampoos
- It also contains acyl glycerols of
caprylic (8:0) and capric (10:0) acids
❖ PALM OIL
- obtained from freshly part
{mesocarp) of the fruit of Elaeis
guineensis (Fam. Lo Arecaceae)
- Elaeis - derived from the Greek word
elaion meaning oil
- Guineensis - indicates its origin of
Guinea Coast of Africa
- It is one of the worlds most widely
consumed edible oils, next to
soybean oil
- It is mostly used as shortening,
margarine and frying fat.
- Used in soap and candle
manufacture
-The oil consists of a mixture of
triacylglycerol whose component
acids are almost equal proportions
of saturated and unsaturated fatty
acids.
❖ PALM KERNEL OIL
- From palm kernels or seeds after
separation, drying and cracking of
the shell of the nut.
- A hard oil and closely resembles
coconut oil with which it is easily
interchangeable
- Composed mostly of saturated fatty
acids and is solid at ambient
temperatures
- Cooking oil, margarine, and
shortening formulations,
confectionery and baking products
and in the preparation of ice cream
and mayonnaise.
MONOUNSATURATED FIXED OILS
❖ CASTOR OIL
- From the ripe seed of Ricinus
communis (Fam. Euphorbiaceae)
- Castor seeds contain 45 - 55% of
fixed oil
- 20 % of protein substance {globulin,
albumin, nucleo albumin,
glycoprotein and ricin- a toxic lectin
hematogglutin , alkaloid ricinine and
other enzymes
- Composed of triacylglycerols, about
85% of which is triricinoleoylglycerol.
- Triricinoleoylglycerol is hydrolyzed
by pancreatic lipase in the
duodenum to release ricinoleic acid
which exerts a cathartic effect.
- RICIN-(POISON) Is not removed by
the extraction of the castor oil but
remains in the oil cake.
- Castor bean pomace contains an
allergen that causes allergic
reaction in hypersensitive
individuals. This powerful allergen is
in the nontoxic protein
polysaccharide fraction
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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023

- USES: - Fatty acids present: Oleic acid,

➢ stimulant cathartic Palmitic acid, Linoleic acid, Stearic
➢ Emollient effect and a plasticizer in acid, Myristic acid, Hexadecanoic
flexible collodion
acid, Arachidic acid
➢ manufacture of soaps and as a
❖ PEANUT
lubricant for internal combustion
engines - Arachis hypogaea (Fam. demulcent
➢ Hydrogenated castor oil is used as Fabaceae)
stiffening agent - contain about 45% fixed oil, 20%,
➢ Ricinoleic acid is an ingredient in a protein and thiamine;
vaginal jelly for restoration and - highly nutritious.
maintenance for -aginal acidity.
- used as food, both whole and when
❖ OLIVE OIL
ground into paste (PEANUT BUTTER)
- FROM THE RIPE FRUIT OF Olea
- aka. arachis oil
europea Fam. Oleaceae)
- colorless liquid or a yellowish liquid
- Known as SWEET OIL
with a slightly nutlike odor and a
- GRADES OF PURITY:
bland taste
- 1) Virgin oil - obtained by gently
- resembles olive oil
pressing the peeled pulp with
- Used as food oil
greater pressure
❖ PEANUT OIL
- 2) First Class or First Grade oil is
- It is a non- drying and therefore has
pressed from crushed pulp with less
no value in paints but does have
pressure
value as lubricant
- 3.) Second Grade of edible oil is
- The oil saponifies slowly but yields
pressed from crushed pulp with
an excellent, firm, white soap.
greater pressure. Hand- picked
- slightly nutlike odor and a bland
olives are used, and the oil is
taste.
obtained promptly before
- INTRAMUSCULAR – CoCoPeaSe
decomposition produces fatty acids.
- Use:
Finally, the pulp, mixed with hot
➢ Solvent for intramuscular
water, is pressed again
injections
- 4.) Technical oil: or the pulp is
➢ PEANUT OIL CAKE, the residue
extracted with Carbon Disulfide to
following expression of the fixed
obtain “Sulfur” Olive oil of inferior
oil, is valuable livestock food.
quality. The fallen, decomposed or
❖ RAPESEED OIL
refused leaves that are allowed to
- Brassica campestris, B. Jjuncea and
ferment furnish a low grade
B. napus (Fam. Brassicaceae)
“tournant oil” which contains large
- Consist of triacylglycerols that are
amounts of free fatty acids
rich in unsaturated fatty acids
- USES:
- contained up to 50% erucic acid
➢ pharmaceutical aid
- Oil obtained from these varieties is
➢ setting retardant for dental
termed canola oil
cements and in the preparation
- CANOLA OIL – CANada Oil Low Acid
of soaps, plasters and liniments
Oil
➢ demulcent
- USES:
➢ emollient
➢ Refined canola oil has bland tast:
➢ laxative
and resist clouding at
➢ nutrient
refrigeration temperature;
➢ salad oil

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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023
therefore it is 1 extensively used
as salad oil
➢ Used as shortenings, margarines
and as a frying oil
POLYUNSATURATED FIXED OILS
❖ SOYBEAN
- Glycine soja( Fam. Fabaceae)
- The seeds contain:
➢ 35% of carbohydrates
➢ 50% of protein
➢ 20% of the fixed oil
➢ UREASE
- Used medicinally as a food for
diabetes and a general food for
humans and livestock.
❖ SOYBEAN OIL
- A drying oil, with an IODINE VALUE
between 120-141 and is not useful as
cooking oil
- Ingredient in parenteral nutrients
and is the source of LECITHIN and
lipid fraction of soybeans yield
STIGMASTEROL
- The oil is used in the manufacture of
varnishes, insulators and other
products.
- FATTY ACIDS:
➢ Linoleic acid (50%)
➢ Oleic acid (30%)
➢ Linolenic acid (7%)
➢ Palmitic acid and Stearic acid
(14%)
- SOYBEAN CAKE
➢ The residue after pressing the oil
➢ Used as a livestock food
➢ 5% of the ash consists largely of
potassium and phosphorus.
- SOYBEAN MEAL
➢ the flour sifted from the seed
Glycine soja deprived of fat
➢ Used for the detection of urea
nitrogen in blood serum by the
enzymatic action of the urease in
the soybean meal.
❖ COTTONSEED OIL
- From Gossypium hirsutum (Fam.
Malvaceae).
- Used as a solvent for a number of
injections.
- A considerable quantity is
hydrogenated and used to make
substitutes for lard.
- A large amount is also used in the
manufacture of soaps.
-FATTY ACIDS PRESENT:
➢ Linoleic acid (45%)
➢ Oleic acid (30%)
➢ Palmitic acid { 20%)
➢ Myristic acid { 3%)
➢ Stearic acid {1%)
➢ Arachidic acid (1%)
❖ COTTONSEED CAKE
- Contains about 0.6% of a toxic
principle, GOSSYPOL which occurs in
secretory cavities in all parts of the
plants. It is present in cold-pressed
oil and can be removed by
treatment with alkalies.
❖ SESAMUM SEED OR SESAME SEED
- is the seed of one or more cultivated
varieties of Sesamum indicum
(Family Pedaliaceae)
- The seeds are small, flattened, oval
or ovate, smooth and shiny, and
whitish, yellow or reddish brown.
Their taste is sweet and oily. They
contain 45-55% of fixed oil, 22% of
proteins (aleurone), and 4% of
mucilage. The seeds are nutritious
and form an important form in India.
- Used as poppy seeds on breads and
rolls.
❖ SESAME OIL
- From Sesamum indicum Linne
(Family Pedaliacease)
- It is also referred to as TEEL OIL or
BENNE OIL.
- The oil is pale yellow, oily liquid,
almost odorless and bland tasting.
- The excellent stability of the oil is
due to the phenolic constituent
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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023
sesamol, which is produced by
hydrolysis of sesamolin, a lignan
present in the unsaponifiable
fraction of the oil.
- SESAME OIL FATTY ACIDS PRESENT:
➢ 1. Oleic acid (43%)
➢ 2. Linoleic acid (43%)
➢ 3. Palmitic (9%)
➢ 4. Stearic acid (4%)
- USES:
➢ Used as solvent
intramuscular injections.
➢ It has nutritive, laxative,
demulcent, and emollient
properties.
➢ SESAMOLIN, contained in the
unsaponifiable fraction of the oil,
is an effective synergist for
pyrethrum insecticides
❖ ALMOND OIL
- Sweet almond and bitter almond
consist of the ripe seeds of the
different varieties of Prunus
amygdalus { Fam. Rosaceae)
- Both bitter and sweet almonds are
expressed for their fixed oil (45 to
50%)
- Sweet almonds are extensively used
as food but bitter almonds are not
suitable for this purpose
❖ ALMOND OIL, EXPRESSED ALMOND OIL,
OR SWEET ALMOND OIL
- Is the fixed oil obtained by
expression from the kernels of
varieties of Prunus amygdalus.
- FATTY ACIDS PRESENT:
➢ 1. Oleicacid (77%)
➢ 2. Linoleic acid (17%)
➢ 3. Palmitic acid {5%)
➢ 4. Myristic acid {1%)
- USES
➢ Used as an emollient
➢ Used as an ingredient
cosmetics
❖ PERSIC OIL, APRICOT KERNEL OIL, OR
PEACH KERNEL OIL
- Is the oil expressed from the kernel
varieties of Prunus armeniaca Linne’
(Apricot Kernel Oil) or from the
kernel varieties of P. persica (Peach
Kernel Oil) (Fam. Rosaceae)
- Persic oil is prepared in the same
manner as is expressed almond oil.
Its characteristic closely resembles
for those of expressed almond oil, and it
is used as a vehicle and a
pharmaceutical necessity.
❖ CORN OIL
- Refined oil obtained from the
embryo of the Zea mays (Fam.
Poaceae)
- The oil-rich embryos (Often called
GERMS) are separated by a
FLOTATION during the preparation of
CORN STARCH.
- The corn oil is a clear, light yellow,
oily liquid that has a faint
characteristic odor and taste.
- USES:
➢ Solvent for injections
➢ It is a solvent for irradiated
ergosterol
➢ It is edible oil, as such, is used in
salads and in the preparation of
food.
➢ An emulsion containing 67% of
corn oil is used as a high-calorie
dietary supplement.
➢ When hydrogenated, the oil
becomes semi-solid and is used
as a shortening for baking.
- FATTY ACIDS PRESENT:
➢ Linoleic acid (50%)
➢ Oleic acid (37%)
➢ Palmitic acid (10%)
➢ Stearic acid (3%)
❖ SAFFLOWER OIL
in
- Is the fixed oil obtained from the
seeds of Carthamus tinctorius Linn’
(Fam. Asteraceae)
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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023
-Linoleic acid 75%, Oleic acid 18%,
Saturated fatty acids about 6%
- Used as high-calorie dietary
supplement
❖ SUNFLOWER OIL
- Linoleic acid 66%, Oleic acid 23%
- Is fixed oil obtained from the seeds
of cultivated varieties of Helianthus
annuus Linne’ (Family Asteraceae).
The oil is used as an alternative to
corn oil and safflower oil for culinary
purposes.
❖ LINSEED OIL
- Also called Flaxseed oil
- A fixed oil obtained from the dried
ripe seed of Linum usitatissimum
Linne’ { Fam. Linaceae)
- It is a yellow liquid having a distinct
odor and disagreeable taste. When
exposed to air it gradually thickens
and darkens in color
- FATTY ACIDS PRESENT:
➢ 1. 52% Linolenic acid
➢ 2. 15% Linoleic acid
➢ 3. 19% oleic acid
➢ 4. 7% stearic acid
➢ 5. 6% palmitic acid
❖ COD LIVER OIL
- Partially destearinated fixed oil
obtained from the fresh livers of
Gadus morhua Linne {Gadidae)
- It is a thin, oily liquid that has a
distinctive, slightly fishy but not
rancid odor and a fishy taste.
- Medicinal grade cod liver oil must
contain, not less than 255 ug (85
units) of vitamin D
- USES
➢ Sources of Vitamin A and D
➢ Topical emollient
ETHIODIZED OIL INJECTION
● Ethiodized oil is an lodine addition
product of the Ethyl ester of the fatty
acids of poppy seed oil.
● It contains not less than 35.2% and not
more than 38.9% of organically
combined iodine.
● It decomposes when exposed to air and
sunlight, becoming dark brown in color.
Ethiodized oil is packaged in sterile form.
● Ethiodized oil is radiopaque and is used
as a diagnostic aid in
hysterosalpingography and
lymphography.
COMPOUNDS RELATED TO FATS
❖ CACAO SEEDS OR CACAO BEANS
- SN: Theobroma Cacao
- FN: Sterculiaceae
- Part used: Seeds
- Collection: seeds —ferment
{change of color from WHIte to
reddish brown)— roasted nibbling
and winnowing — grinding— paste
(cacao butter- 50 % fat)
- Bitter chocolate is the paste that
congeals at room temperature.
- Sweet chocolate is a bitter
chocolate to which wafer and
vanilla and other flavoring
substances have been added.
- Prepared cacao or breakfast cacao
is the residue after the expression of
the oil that is powdered.
- Cacao red is responsible for the red
coloration of the seed, which is
formed through the action of an
enzyme to a glycoside.
- When the seeds are roasted, the
theobromine in the kernel passes
into the shell. The shell is the
commercial source of this xanthine
derivative.
- COCOA is the powder prepared from
the roasted, cured kernels of the ripe
seed of Theobroma cacao
- It occurs as a weak reddish to
purplish brown that has a
chocolate like odor and a taste that
is not sweet.
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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023

- Constituents: ❖ LANOLIN
➢ Theobromine 1-4% - SN: Ovies aries
➢ Solid fat 40-60% - FN: Bovidae
➢ Starch- 15 % - It contains between 25 to 30% of
➢ Caffeine 0.07-0.36% water and therefore is commonly
➢ Proteins 15% called hydrous wool fat.
- USES: - a Yellowish white, ointment like mass
➢ 1. Ingredient in cosmetic that has a slight characteristic odor.
ointments When heated on a steam bath, it
➢ 2. In pharmacy for coating pills separates at first into 2 layers.
➢ 3. Preparation of suppositories Continued heating with frequent
➢ 4. Diuretic cacao stirring drives off the water that
➢ 5. Employed in making cocoa makes up the lower layer.
syrup - The chief constituents are
➢ 6. A popular beverage cholesterol and isocholesterol.
❖ THEOBROMA OIL OR COCOA BUTTER Lanolin also contains the esters of
- Fat obtained from the roasted seed lanopalmitic, lanoceric, carnaubic,
of Theobroma cacao oleic, myristic and other fatty acids.
- Characteristics: syrup - USES
➢ 1. Yellowish white solid ➢ 1. Cosmetics
➢ 2. Has a faint, agreeable odor ➢ 2. Rust proof coatings and
➢ 3. Abland and chocolate like lubricants
taste ➢ 3. Raw material in the
➢ 4. Melts between 30 and 35°C cholecalciferol production
- FATTY ACIDS PRESENT: ➢ 4. As a water absorbable
➢ 1) Oleic acid 3% ointment base **but can cause
➢ 2) Steric Acid 34% allergenic reactions to
➢ 3) Palmitic acid 26% hypersensitive persons
➢ 4) Linoleic acid 2% ❖ ANHYDROUS LANOLIN
- The sharp melting point, the - It contains not more than 0.25% of
brittleness and the non-greasiness water. After lanolin has been purified
is due to its glyceride structure and bleached, it is dehydrated.
which is the oleopalmitostearin. Anhydrous lanolin is usually
- Used as a suppository base. referred as wool fat
❖ HYDROGENATED VEGETABLE OIL - Used as water absorbable ointment
- It is refined, bleached, base
hydrogenated, and deodorized
vegetable stearins and consists
tiktok break
mainly of the triglycerides of stearic
and palmitic acids.
- It is a fine, white powder at room
★ What is the advantage of Sodium
temperature and melts between 61
stearate to anhydrous Lanolin?
to 66C to give a pale yellow, oily
★ Answer: Sodium sterate has lower
liquid.
potential to cause allergies
- It is used as tablet lubricant

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PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023
FATTY ACIDS
● This is usually obtained by hydrolysis of
fats and oils.
● 1. STEARIC ACID
- These are hard, white or faintly
yellow solids or powders and
considered to be insoluble in water.
- Used as an emulsion adjunct and
tablet lubricant.
- SALTS:
➢ 1. Calcium stearate used as
tablet lubricants
➢ 2. Magnesium stearate
➢ 3. Zinc sterate – dusting powder
➢ 4. Sodium sterate – as an
emulsifying and stiffening agent
➢ 5. Aluminum monostearate — a
suspending agent
➢ 6. Glyceryl monostearate
emulsifying
➢ 7. Propylene glycol monostearate
agents
● ISOPROPYL MYRISTATE AND ISOPROPYL
PALMITATE
- Are mixtures consisting of the esters
of isopropyl alcohol and saturated
high molecular weight fatty acids.
- The respective semisynthetic
products contain not less than 90%
of the designated esters.
- These products are used as
ingredients in topical ointment and
creams
- They offer some advantage over
vegetable oils, including freedom
from oxidation and rancidity and a
less oleaginous (greasy) character.
- In addition, they lack the
hypersensitization potential
encountered with lanolin.
● OLEIC ACID
- Obtained from edible fats and fixed
oils
- Often obtained as a by product in
the production of stearic acid
- Consists chiefly of
cis-9-octadecenoic acid
- Pale yellow oily liquid
- It is practically insoluble in water but
is miscible with alcohol
- It gradually absorbs oxygen and
darkens when exposed to air
- An emulsion adjunct
● ETHYL OLEATE
- Is used as a pharmaceutical vehicle
- Compared with fixed oil vehicle is
less viscous and more rapidly
absorbed by the body tissues
● OLEYL ALCOHOL
- Emollient
- Emulsifying agent
● LINOLEIC AND LINOLENIC ACIDS
- Polyunsaturated octadecenoic
acids
- Essential for human nutrition and
have been called rapidly absorbed
by the body tissues Vitamin F.
- A mixture of essential unsaturated
fatty acids that contains primarily
linoleic and linolenic acids can be
obtained from - soybean oil and
other suitable vegetable oils. This
mixture is used as a dietary
supplement
● UNDECYLENIC ACID
- Is 10-UNDECENOIC ACID
- It is prepared by the pyrolysis of
ricinoleic acid, which is obtained
from castor oi
- Has antifungal properties
- Often combined with zinc
undecylenate or other agents to
treat athlete's foot
● Ca Undecylenate
- Used in powder for diaper rash and
similar skin irritations
● Sodium Morrhuate
- Sodium salt of the fatty acids of cod
liver
- Available as sterile solution
- Used as sclerosing agent to
obliterate varicose veins
15
PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023
● Prepared Suet NF (1950)
- Mutton Suet, Sebo de macho
- Origin: internal fat from the
abdominal part of Ovis aries
(Bovidae)
- Use: ointment base
● Lard NF X (1955)
- Synonyms: Hogs Lard, Manteca,
Grasa
- Origin: fatty matter of the abdomen
of the hog Suis scrofa (Suidae)
- Use: ingredient in the preparation of
ointment and cerates- emollient
WAXES
● Are usually defined as esters resulting
from the condensation of
high-molecular weight, straight-chain
acids and high molecular weight,
primary straight chain alcohols.
● In plants, waxes are found in
connection with the outer cell walls of
epidermal tissue particularly in fruits
and leaves.
● The function of wax appears to be
protection against the penetration or
loss of water
● Insects also secrete waxes for various
purposes
● What is the importance of waxes in
plants and animals?
- ANSWER: to prevent water loss in
plants and to water-proof the
animal
● Vegetable wax – Carnauba and
Bayberry wax
● Insect wax – Lac and Bees wax
● saponification and acid value are both
high, low iodine value
SPERMACETI
● A waxy substance obtained from the
head of the sperm whale Physeter
macrocephalus (Family Physeteridae)
● Formerly recognized as a quality
emollient and a desirable ingredient in
cold creams and other cosmetics
● However, the sperm whale is an
endangered species.
● What is the most obvious
disadvantage of using SPERMACETI? –
endangered species
● yiee miras ya keni tiktok ka pa kanyan
WAXES
❖ Synthetic Spermaceti or esters wax
- Is a mixture consisting primarily of
esters of saturated fatty alcohols
(C14 to C18) and saturated fatty
acids (C14 to C18)
❖ Cetyl Alcohol
- Is a mixture of solid alcohols
consisting chiefly (not less than
90%) of cetyl alcohol or
1-hexadecanol
- It is used as an emulsifying aid and
a stiffening agent in pharmaceutics
preparations
❖ Stearyl Alcohol
- Is a mixture of solid alcohols
consisting chiefly (not less than
90%) of stearyl alcohol or
1-octadecanol
- It is used as an alternative to cetyl
alcohol, as in cetosteryl alcohol
- Cetosteryl alcohol contains not less
than 40% of stearyl alcohol and not
less than 90% of cetyl and stearyl
alcohols pr
❖ JOJOBA OIL
- It is a liquid wax expressed from
Seeds of Simmondsia chinensis
(Family Simmondsiaceae).
- The plant is bushy shrub native to
the arid regions of northern Mexico
and to the western United States.
- Jojoba seeds contain 45-55% of an
ester mixture {not triglycerides) that
is liquid at ambient temperatures
16
PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023
- COMPONENTS:
➢ 1. 35% of eicosenoic acid {a C,5
unsaturated acid)
➢ 2. 2.22% of eicosenol (a Cy
unsaturated alcohol)
➢ 3. 21% of decosenol {a C22
unsaturated alcohol)
- Hydrogenation of the oil yields a
crystalline wax
- USES: emollient and pharmaceutic
necessity.
❖ YELLOW WAX OR BEESWAX
- It is the purified wax from the
honeycomb of the bee, Apis
mellifera (Fam. Apidae)
- Wax is secreted on the ventral
surface of the last 4 segments of the
abdomen of the worker bees. The
wax excretes through pores in the
chitinous plates and is employed by
the bees in the construction of the
comb.
- The honeycomb, after separation
from the honey, is melted in water,
then cooled and remelted, and
finally strained and allowed to
harden in molds.
- Beeswax is solid, varying in color
from yellow to grayish brown,
- It has an agreeable, honey-like odor,
and a faint characteristic taste.
- When cold, beeswax is somewhat
brittle and exhibits a dull, granular,
noncrystalline fracture.
- COMPONENTS:
➢ 1. myricyl palmitate (72 %)
➢ 2. cerotic acid (14%)
➢ 3. Hydrocarbons (12%)
➢ 4. Moisture
➢ 5. Pollen
➢ 6. Propolis (Bee glue)
- USES
➢ Yellow wax is a stiffening agent
and an ingredient in yellow
ointment.
➢ It is used as a base for cerates
and plasters.
➢ Commercially, it is contained in a
number of polishes.
❖ WHITE WAX
- It is bleached, purified wax from the
honeycomb of the bee. A. mellifera
Linne’ {Family Apidae)
- The bleaching process is
accomplished by allowing the
melted wax to flow slowly into a
revolving wetted cylinder, upon
which it hardens in thin, ribbon-like
layers.
- These layers are removed and
exposed to sunlight and air until
they are bleached. {The process
usually is repeated). The bleached
wax is finally melted and cast into
cakes of various shapes.
- White wax is also referred to as
bleached beeswax
- SAPONIFICATION CLOUD TEST – It is
a rapid, reliable and expensive
method of detecting the presence
of certain adulterants of natural
beeswax.
- USES – Employed pharmaceutically
in ointments and cold creams.
- What is the natural source of White
wax? – Since it is also known as
bleached beeswax, it is naturally
from Apis melifera (Apidae)
❖ CARNAUBA WAX
- Obtained from the leaves of
Copernicia prunifera (Family
Arecaceae), a palm growing from
northern Brazil to Argentina.
- COMPONENTS:
➢ 1. myricyl cerotate (80%) –
candles, wax varnishes, leather
and
➢ 2. free monohydric alcohols
(10%) – furniture polishes
➢ 3. a lactone – beeswax
➢ 4. a resin
➢ 5. other minor constituents.
- It is used in the manufacture of
candles, wax varnishes, leather and
17
PHARMACOGNOSY AND PLANT CHEMISTRY
PCOG 211 (Lecture)
(BS Pharmacy) | PROF. APRIL LINGAT | MIDTERMS SEM 2 2023

furniture polishes in place of system causing elevation in blood

beeswax
PROSTAGLANDINS
● Are C20 lipid metabolites formed in the
body from essential, unsaturated fatty
acids in the diet.
● Apparently occur in all mammalian
tissues, but they are present in low
concentrations
● Responsible for pain, swelling, fever
pressure.
● Is rapidly inactivated in the lungs and
other body tissues.
● The short duration of action is
desirable for its oxytocic action.
15-METHYL PROSTAGLANDIN F2A,
(15S)-METHYL PGF2A OR CARBOPROST
● Is the 15-methyl analog of PGF2a
● USE: terminating the 2nd trimester of
pregnancy.
● Given as IM injection
● no cause of nausea, diarrhea, and high
blood pressure

PROSTAGLANDIN E2 OR PGF2 OR
DINOPROSTONE

● USE: termination of second trimester of

pregnancy
● Given as vaginal suppository
● AE: vomiting, nausea, headache and
chills

PROSTAGLANDINS F1, PGE1 OR

ALPROSTADIL

● USE: vasodilator, inhibits platelet

aggregation, and stimulates intestinal
and uterine smooth muscle
● For palliative therapy to temporarily
● FOUR CLASSES OF PROSTAGLANDINS maintain neonates with patent ductus
- Prostaglandin A arteriosus and certain congenital heart
- Prostaglandin B defects.
- Prostaglandin E ● Given as IV continuous infusion
- Prostaglandin F

PROSTAGLANDINS F2A PGF2A

● DINOPROST
● Uterine stimulant
● USE: terminating second trimester of
pregnancy.
● AE: Extension of contractile effect to
muscle of the GIT action is desirable for
producing vomiting and/or diarrhea
and to smooth muscle of the vascular

18