Pharmacognosy & Plant Chemistry (lec)

 Lipids (fixed oils, fats and waxes) – are esters of long- chain fatty acids and alcohols, or of
closely related derivatives.
◦ The chief difference between these substances is the type of alcohol
Fixed oils and fats – glycerol combines with fatty acids
Waxes – the alcohol has a higher molecular weight
 Fats and fixed oil - are obtained from either plants (olive oil, peanut oil) or animals (lard).
Their primary function is food (energy) storage.
◦ Fixed oils and fats are often separated from crude vegetable drugs (by expression) or the
crude animal drugs (by extraction).

 Fixed oils and fats differ only as to melting point;

◦ those that are liquid at normal temperatures are known as fatty or fixed
oils.
Example vegetable oil except for cocoa butter because it is solid vegetable oil.
◦those that are semisolid or solid at ordinary temperatures are known as fats.
Example animal fats except for cod liver oil because it is liquid animal fat.

Test based on the chemical constitution of fatty acids:

 Acid value or acid number
◦ the number of milligrams of potassium hydroxide required to neutralize the free fatty acids in
1 g of the substance)
◦ indicates the amount of the free fatty acids present in the oil;
 Saponification value
◦ indicates the number of milligrams of potassium hydroxide required to neutralize the free
acids and saponify the esters contained in 1 g of the substance
 Iodine number
◦ the number of grams of iodine absorbed, under
prescribed conditions, by 100 g of the substance
◦ indicates the degree of unsaturation.

 Fixed oil and fats – vegetable origin are obtained by expression in hydraulic presses.
◦ If the expression is carried out in the cold, the oil is known as a “virgin oil” or a “cold-pressed
oil”.
◦ In contrast, if the expression is carried out in heat, the oil is known as a “hot-pressed oil”.
 Organic solvents – are used for the extraction of oils.
 Animal fats – are separated from the other tissues by rendering with steam, with or without
pressure. The heat melts the fat, which rises to the top and may be separated by decantation.
 Oils – may be further clarified by filtration and bleached with ozone.
Stearins – are often removed by chilling and filtration.
 Seeds – are the usual source of fixed oils and, as a few examples, the following might be
mentioned: cottonseed, linseed, sesame seed, hemp seed, coconut, castor beans, almond, and
others.
 Chemically, the fixed oils and fats are glycerides of fatty acids that have the general formula:
CH2 –O–CO–R |
CH – O – CO – R’
|
CH2 –O–CO–R”
 If R, R’, and R” are the same fatty acid radical, the compound is called triolein, tripalmitin,
tristearin, and so forth. If R, R’, and R” are different fatty acids, a mixed glyceride results. The
composition of the glycerides in any fixed oil or fat is influenced by the amounts of various fatty
acids that are present during formation. Thus, the composition of fixed oils and fats from any
source can vary within certain limits.

 The glycerides of unsaturated fatty acids are liquid

 The glycerides of saturated fatty acids of sufficient
chain length are solid.
Some more common fatty acids:
Saturated fatty acids
 Caproic........................ CH3(CH2)4COOH
 Caprylic........................ CH3(CH2)6COOH
 Capric........................... CH3(CH2)8COOH
 Lauric........................... CH3(CH2)10COOH
 Myristic......................... CH3(CH2)12COOH
 Palmitic......................... CH3(CH2)14COOH
 Stearic.......................... CH3(CH2)16COOH
 Arachidic....................... CH3(CH2)18COOH

Unsaturated fatty acids

Oleic............................. CH3(CH2)7CH:CH(CH2)7COOH
Linoleic............ CH3(CH2)4CH:CHCH2 CH(CH2)7COOH
Linolenic... CH3CH2CH:CHCH2:CHCH2CH:CH(CH2)7COOH
Ricinoleic...CH3(CH2)5CHOHCH2CH:CH(CH2)7COOH

BIOSYNTHESIS OF LIPIDS
The synthesis of fats and fixed oils by living organisms was believed to be affected simply by a
reversal of the reactions responsible for their degradation.
 These include the hydrolysis of the glycerol-fatty acids esters by the enzyme lipase and the
subsequent removal of 2-carbon units as acetyl- CoA from the fatty acid chain by β-oxidation.

 Acetate first reacts with CoA, and the acetyl-CoA thus formed is converted by reaction with
carbon dioxide to malonyl-CoA.
 This, in turn, reacts with an additional molecule of actyl-CoA to form a 5-carbon intermediate,
which undergoes reduction and elimination of carbon dioxide to produce butyryl-CoA.
 Malonyl-CoA again reacts with this compound to form 7-carbon intermediate, which is
reduced to caporyl-CoA.
 Repetition of the reaction results in a fatty acid containing an even number of carbon atoms
in its chain.
 Thus, the malonyl portion of malonyl-CoA, a 3- carbon compound, is actually the source of the
2- carbon biosynthethic units of the fatty acids.

 Pathways of biosynthesis of unsaturated, branched-chain, odd-numbered.

the first step in the production of a mono- unsaturated acid is the formation of the acyl-CoA
derivative of its saturated analog.
 followed by enzymatic desaturation. Hydroxylation appears to be independent or to follow
desaturation.
 hydroxylation is not involved as an intermediate step in the desaturation process.
 Evidence suggests that the saturated acyl group of the acyl-CoA derivative is transferred to
the 2- positionof phiosphatidyl glycerol before the desaturation and additional reactions.

Enzymes present in certain fractions of unripe castor seeds (Ricinus communis, Fam.
Euphorbiaceace) can hydroxylate oleic acid to produce ricinole acid.
 The glycerol moiety utilized in lipid biosynthesis derives mainly from the L-isomer of α-
glycerophosphate (L-a-GP).

 Fixed oil – are sometimes classified into drying oils, semidrying oils, and nondrying oils. This
classification is based on their ability to absorb oxygen from the air. Oxygen saturates the
double bonds form oxides that may polymerize to form hard films. This property of drying oils is
of great importance in the paint industry. The double bonds in the unsaturated fatty acids also
take up hydrogen under the proper conditions.
Hydrogenation – of the liquid oils produces semisolid fats that are extensively used as cooking
fats and shortenings.

Fixed oils may be hydrogenated by passing hydrogen, in the presence of nickel of palladium,
through the oil heated to 160 to 200 ̊C. The unsaturated glycerides are more less converted to
saturated glycerides, which are solid at room temperature and stable. Many such oils are used
for culinary purposes.
Sulfated or sulfonated oils – are obtained by reacting sulfuric acid with the oil, keeping the
temperature down by chilling. The oil is then washed and neutralized. If the oil contains an
olefinic linkage, the acid molecule adds onto the double bond. The compound formed is a
sulfate of the fat.

 Fixed oils and fats are employed in pharmaceuticals for their emollient properties. They may
also serve, either in their natural form or in emulsions, as vehicles for other medicaments.
 Fats and oils – are used in the manufacture of soaps (sodium and potassium salts of the fatty
acids), as drying oils in the manufacturer of paints and varnishes, and as lubricants.
 Lipids also form an important class of foods; their high caloric value and low osmotic pressure
have prompted interest in some plant oils as parenteral nutrients in hyperalimentation for new
therapeutic agents and commercially important lipids.
 In addition, investigations are being undertaken to ascertain the most advantageous types of
antioxidants to prevent or to retard rancidity of fixed oils and fats.

CASTOR OIL
Castor bean or castor oil seed – (also known as tangan-tangan) is the ripe seed of Ricinus
communis Linne (Fam. Euphorbiaceae).
 Ricinus – is latin and means a tick or a bug, referring to the seed’s resemblance to some bugs
in shape and markings.
 The plant is an annual in temperature climates, or a tree, attaining the height of 15 meters, in
the tropics. There are many forms of the plant, with variations in the shape of the leaves and
the color, size, and markings of the seeds.
 The Fruit – is a 3-celled spiny capsule, each cell containing an avoid albuminous seed. The
plant is indigenous to India. It is extensively cultivated in India, Brazil, other South and Central
American countries, the Soviet Union, various parts of Africa, southern Europe, and the
southern United States.
 The seeds have been found in Egyptian tombs.

 Castor seeds – contain from 45 to 55% of the fixed oil; about 20% of protein substances
consisting of globulin, albumin, nucleoalbumin, glycoprotein, and ricin (a toxic lectin or
hemagglutin); an alkaloid, ricinine; and several enzymes.
Castor bean pomace contains an allergen that causes allergic reactions in hypersensitive
individuals.
 Castor Oil – is the fixed oil obtained from the seed of Ricinus communis. It is prepared by
passing the seeds through a decorticator, which has rollers with sharp cutting edges break the
estate but do not injure the kernel.
 The yield of the “cold-pressed” oil separated by hydraulic pressure is 60% and represents a
light- colored, good grade.

 Castor oil – a pale yellowish or almost colorless, transparent, viscid liquid.

 Castor oil – is a stimulant cathartic; the usual dose is 15 to 60 ml. The oil is also used as a
plasticizer in flexible collodion.
 Castor oil – is employed in the manufacture of soaps and as a lubricant for internal
combustion engines.
Hydrogenated castor oil – used as a stiffening agent in some pharmaceutic formulations.

OLIVE OIL
 Olive oil – the fixed oil obtained from the ripe fruit of Olea europea Linne (Fam. Oleaceae).
Olive oil is sometimes called sweet oil/ Oil of Europe.
 The generic name Olea is from the Latin olive, meaning olive or from the Greek elaion,
meaning oil.
 Olive oil – is miscible with ether, carbon disulfide, and chloroform and slightly soluble in
alcohol. Its specific gravity is 0.910 to 0.915 at 25 ̊C.
 Forms of olive oil:
◦ Virgin – prepared from cold press
◦ Technical – prepared from boiling water
◦ Tournant – prepared from fallen and decomposing fruit ◦ Sulfur – obtained by solvent
extraction wing CS2
 Olive oil is classed as a pharmaceutic aid. It is used as a setting retardant for dental cements
and in the preparation of soaps, plasters, and liniments. It is also a demulcent, an emollient,
and a laxative. Olive oil is a nutrient and is widely used as a salad oil.

PEANUT OIL
 Peanut – is the ripe fruit or seed of Arachis hyopogaea
 Are extensively used as food, both whole and when ground into a paste (peanut butter).
 Peanut oil – is the refined fixed oil obtained from the seed kernels of one or more of the
cultivated varieties of A. hypogaea.
 Peanut oil – is sometimes referred to as arachis oil.
It closely resembles olive oil and is used as a pharmaceutic acid. Its principal use is as a food
oil. It is nondrying and therefore has no value in paints but does have value as a lubricant. The
oil saponifies slowly but yields an excellent, firm, white soap.
 Peanut oil is a solvent for intramuscular injections.
 Peanut oil cake, the residue following expression of the fixed oil, is a valuable livestock food.
Linne (Fam. Leguminosae).

SOYBEAN OIL
 Soybean – is the ripe seed of Glycine soja Siebold at Zaccarini (Fam. Leguminosae), an
important food and forage crop.
Soybeans – are used medicinally as a food in diabetes and as a general food for humans and
livestock.
Soybean oil – is an ingredient in parenteral nutrients and is a source of lecithin.
 Lecithin – an ingredient in a number of proprietary products that are useful in controlling
deranged lipid and cholesterol metabolisms.
 The oil is used extensively in the manufacture of varnishes, insulators, and other products.

Partially hydrogenated soybean oil – is an ingredient in a number of combination products for

oral administrations that are described as balanced dietary supplements.
 Soybean Cake, the residue after pressing out the oil, has a high value as a livestock food.
Soybean meal – is the flour sifted from the decorticated, ground seed of Glycine soja deprived
of fat. It can be used for the detection of urea nitrogen in blood serum by the enzymatic action
of the urease in the soybean meal.

COTTONSEED OIL
 Cottonseed oil – is the refined, fixed oil obtained from the seed of cultivated plants of various
varieties of Gossypium hirsutum Linne or of other species of Gossypium (Fam. Malvaceae).
 The constituent gossypol is a very toxic principle that can cause male sterility or permanent
contraceptive for men.
Cottonseed oil – employed pharmaceutically 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 soap.
Cottonseed cake contains about 0.6% of a toxic principle, gossypol, which occurs in secretory
cavities in all parts of the plant. It is present in cold-pressed oil and can be removed by
treatment with alkalies.

SESAME OIL
 Sesasum seed or sesame seed – is the seed of one or more cultivated varieties of Sesamum
indicum Linne (Fam. Pedaliaceae).
 Sesasum – from the Greek sesamon, the original name of the plant; indicum refers to its
habitat, india.
 Sesame Oil – is the refined, fixed oil obtained from the seed of one or more cultivated
varieties of S. indicum. It is also referred to as teel oil or benne oil. The oil is a pale yellow, oily
liquid, almost odorless and bland tasting.
 Sesame oil is classed as a pharmaceutic aid and is used as a solvent for IM injections.

ALMOND OIL
 Sweet almond and bitter almond consist of the ripe seeds of different varieties of Prunus
amygdalus Batsch (Fam. Rosaceae).
 Prunus – the classic name of the plum tree; amygdalus is from the greek amygdolos, meaning
almond tree; amara and dulcis, the variety designations, are Latin and mean bitter and sweet,
respectively.
 Sweet almonds are extensively used as a food, but bitter almonds are not suitable for this
purpose. The seeds of the bitter almond were known to be poisonous in the days of antiquity.
 Almond oil, expressed almond oil, or sweet almond oil – is the fixed oil obtained by
expression from the kernels of varieties of P. amygdalus.
 Expressed almond oil is an emollient and an ingredient in cosmetics.

PERSIC OIL
 Persic Oil, apricot oil or peach kernel oil - is the oil expressed from the kernels of varieties of
Prunus armeniaca Linne (apricot kernel oil) or from the kernels of varieties of P. persica Siebold
et Zuccarini (peach kernel oil) (Fam. Rosaceae).
 Persic oil – is prepared in the same manner as is expressed almond oil. Its characteristics
closely resemble those of expressed almond oil, and it is is ued as a vehicle and pharmaceutic
necessity.

COCONUT OIL
Coconut oil – is the fixed oil obtained by expression or extraction from the seed kernels of the
coconut palm, Cocos nucifera Linne (Fam. Palmae).
 Coconut oil and medium chain triglycerides is used when conventional food fats are not well
digested or absorbed.
Coconut oil and medium chain triglycerides are ingredients in number of combination
products for oral administration that are described as balanced dietary supplements.
 Primary constituent: Lauric acid
◦ Antibacterial, antiaging, anticancer property

CORN OIL
 Corn oil – is the refined obtained from the embryo of
Zea mays Linne (Fam. Gramineae).
 The Germ Oil cake that remains is ground and sold as
cattle feed (oil cake meal).
 Corn oil – is a clear, light yellow , oily liquid that has a
faint characteristics odor and taste.
 Corn oil – used as a solvent for injection; it is also a solvent for irradiated ergosterol. It is an
edible oil and, 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. Corn oil is also an ingredient in a
number of combination products for oral administration that are described as balanced dietary
supplements. When hydrogenated, the oil becomes semisolid and is used as a shortening for
baking.

SAFFLOWER OIL
 Safflower seed oil – is the fixed oil obtained from the seeds of Carthamus tinctorius Linne
(Fam. Compositae).
SUNFLOWER OIL
 Sunflower oil is the fixed oil obtained from the seeds of cultivated varieties of Helianthus
annuus Linne (Fam. Compositae)
 The oil is used as an alternative to corn oil and safflower oil for culinary purposes.

ETHIODIZED OIL INJECTION

 Ethiodized oil is an iodine addition product of the ethyl estyer 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.
 Ethiodized oil is radiopaque and is used as a diagnostic aid in hysterosalpingography and
lymphography.
**Note** Official fixed oils used in IM injections  Cottonseed oil
 Corn oil
 Peanut oil
 Sesame oil

FATS
 THEOBROMA OIL
 Cacao seeds or cacao beans are the roasted seeds of Theobroma cacao Linne (Fam.
Sterculiaceae). Theobroma is Greek and means “food of gods”; cacao is from Aztec name of the
tree; “chocolate is from the Nahualt.
 The seeds are separated from the pod and allowed to ferment. During the process, they
change from white to dark reddish brown. They are roasted (not above 140C) to lose water and
develop their characteristic odor and taste.
◦ The roasted seeds are passed through a “nibbling” machine to crack the seed coats (cacao
shell), which separated from the kernels by winnowing. The broken kernels are called “ribs”

◦ When ground between hot rollers, they yield a paste containing up to 50% of fat, cacao
butter.
◦ The paste congeals at room temperature to form bitter chocolate.
◦ Sweet chocolate is bitter chocolate to which sugar and vanilla or other flavoring substances
have been added.
◦ After expressing cacao butter, the marc which retains some oil, is powdered and is known as
prepared cacao or breakfast cacao.
 Cocoa is a powder prepared from the roasted, cured kernels of the ripe seed of Theobroma
cacao. It occurs as a weak reddish to purplish brown to moderate brown powder that has
chocolatelike odor and taste that is not sweet. Cocoa is employed in making cocoa syrup, which
is a flavored vehicle. Cocoa, also known as “breakfast cocoa”, is a popular beverage and usually
contains more than 22% of “fat”.

HYDROGENATED VEGETABLE OIL

 Hydrogenated Vegetable Oil – is refined, bleached, hydrogenated, and deodorized vegetable
oil stearins and consists mainly of the triglycerides of stearic and palmitic acids.
 It is fine, white powder at room temperature and melts between 61 and 66 ̊C to give a pale
yellow, oily liquid.
 It is used as a tablet lubricant.

LANOLIN
 Lanolin - is the purified, fatlike substance from the wool of the sheep, Ovis aries Linne (Fam.
Bovidae). It contains between 25 and 30% of water and therefore is commonly called hydrous
wool fat (contains 20-25% moisture)
 Lanolin is used as a water-absorbable ointment base. ANHYDROUS LANOLIN
 Anhydrous Lanolin (0.21% moisture; best absorbed) – is lanolin that contains not more than
0.25% of water. After lanolin has been purified and bleached, it is dehydrated. Anhydrous
lanolin is usually referred to as wool fat.
 Anhydrous Lanolin is a water-absorbable ointment base. It is more readily absorbed through
the skin than any other known fat and is therefore valuable as a base for therapeutic agents
that are administered by inunction. In addition, it possesses emollient properties.

LANOLIN ALCOHOLS
 A mixture of aliphatic alcohols, triterpenoid alcohols, and sterols, obtained by the hydrolysis
of lanolin, is called lanolin alcohols. This product contains not less than 30% cholesterol and is
used as an emulsifying agent in ointment formulation.
• Volatile oils

 -  The odorous principles found in various plant

parts.

 -  They evaporate when exposed to air at ordinary temperature, hence, are called
volatile oils, ethereal oils, or essential oils (represent “essences” or the odoriferous
constituents of the plants.)
 -  Colorless when fresh, but on long standing they may oxidize and may resinify, thus
darkening in color.
 -  Should be stored in cool, dry place in tightly stoppered, preferably full (not half-
emptied), amber glass containers.

- May occur in specialized secretory structures such as glandular hairs (Labiatae), modified
parenchymal cells (Piperaceae), oil-tubes called vittae (Umbelliferae), or in lysigenous or
schizogenous passages (Pinaceae, Rutaceae).

 -  May be formed directly by the protoplasm, by decomposition of the resinogenous

layer of the cell wall, or by the hydrolysis of certain glycosides.
 -  Conifers contains volatile oils in all tissues, rose contain appreciable quantities only in
petals, in cinnamon, only in the bark and leaves, umbelliferous fruits in the pericarp, in
mints in the glandular hairs of the stems and leaves,

.... In the orange, one kind of oil occurs only in the flower petals and another kind only in the
rind.

- vol. oils may act as repellants to insects, thus preventing the destruction of the flowers and
leaves; or they may serve as insect attractants, thus aiding in cross-fertilization of the flowers.
2 broad classes of Chemical constituents of volatile

oils based on their biosynthetic origin:

1. Terpene derivatives formed via the acetate- mevalonic acid pathway

2. Aromatic compounds formed via the shikimic acid –phenylpropanoid route

Characteristics of volatile oils:

 -  They posses characteristic odors

 -  Characterized by high refractive indices
 -  Optically active
 -  Their specific rotation is a valuable diagnostic property
 -  Volatile oils are immiscible with water, but they are sufficiently soluble to impart their
odor to water, aromatic water are dependent on this slight solubility
 -  Volatile oils are soluble in ether, alcohol and most organic solvents

Difference between volatile oils and fixed oils:

Volatile Oils Fixed Oils
Obtained by expression and extraction using organic
Can be distilled from their natural sources
solvents
Do not consist of glyceryl esters of fatty consists of glyceryl esters of fatty acids upon
acids hydrolysis
Do not leave a permanent grease spot on
leaves a permanent grease spot on paper
paper
Cannot be saponified with alkalies Can be saponified with alkalies
Do not become rancid becomes rancid on
on exposure to light & exposure to light & air

• Methods of obtaining volatile oils:

1. Obtained by distillation of the plant parts

containing the oil.

 Types of distillation:

a. Water distillation – applied to plant material that is dried and not subject to injury by boiling.

e.g. turpentine oil

b. Water and steam distillation – employed for either dried or fresh substances that may be
injured by boiling.

e.g. cinnamon oil, clove oil

c. Direct steam distillation – applicable to fresh plant drugs.

e.g. peppermint, spearmint

Other Methods of obtaining volatile oils:

a. Enzymatic hydrolysis of the glycosides – e.g. Glycosidic volatile oils (mustard oil) from black
mustard seeds

- The glycoside sinigrin is hydrolyzed by myrosin with the production of volatile mustard oil.

b. Expression method – by mechanical means e.g. lemon oil, orange oil, lime, bergamot
• Oil was obtained by expressing the rind of the fresh fruit, also known as “hand pressed”

3 methods are practiced:

1. Sponge process – the rind is removed from the fruits and after dipping in water is pressed by
hand, the oil is collected in a bowl ; and transferred to a larger container for separation.

2. Ecuelle method – the fruit is rolled about in hollow bowls, the walls of which are covered
with spikes, the oil cells are punctured and the oil w/c exudes is collected in the hollow handle.

3. Machine process – either the sponge or ecuelle may be adapted to machines w/c perform
the operation on a larger scale.

Con’t. Other Methods of obtaining volatile oils: c. Extraction – the odorous principle may be

extracted by some form of solution or absorption.

*this may be effected by maceration, digestion, percolation with appropriate immiscible

solvent, enfleurage or extraction with a volatile solvent.

*Maceration – the odorous portions of the plant (generally fragrant flowers) are allowed to
remain in contact w/ bland, inodorous fixed oil or fat. The oil or fat absorbs that odor and after
a certain length of time that oil is strained & is used in the manufacture of perfumes in a similar
manner to pomades.
e.g. rose, violet, orange flowers, narcissus and lily of the valley

*Digestion – similar to maceration except that a moderate heat is employed.

*Enfleurage – a cold process consists of spreading a thin layer of purified inodorous fat (a
mixture of beef tallow 40% & lard 60%) upon both sides of sheets of glass held in frames known
as chasses.

24 hrs. for jasmine; 72 hrs for tuberose (pomade)

*Percolation w/ volatile solvents – solvent employed is a highly purified petroleum benzin.

(proceeds for 8 hrs.), the volatile solvent is removed by vacuum distillation & the resulting
product is known of concrete. These concretes or flower waxes are removed by dissolving the
odorous portion in strong alcohol & separate the insoluble waxes by filtration.

o
... small quantities of alcohol-soluble waxes are removed by chilling to 20 C. The resulting
products are known as “absolutes.” used in perfumery

*Destructive distillation – means of obtaining “empyreumatic oils”

e.g. wood or resin members of Pinaceae or Cupressaceous is heated w/o access to air,
decomposition takes place and volatile compounds are driven off. The resultant mass is
charcoal.

2 layers:

1. Aqueous layer containing wood naphtha (methyl alcohol)

2. Pyroligneous acid (crude acetic)
 Medicinal and commercial uses of volatile oils

 -  Used for flavoring purposes

 -  Possesses carminative action
 -  Analgesic (wintergreen oil)
 -  Used in perfumery
 -  For masking or providing odor to household cleaners, polishes and insecticides

• Volatile oils generally consists of:

1. Eleoptene – the hydrocarbon portion of the oil,

w/c is liquid

2. Stearoptene – the oxidized hydrocarbon portions of the oil, w/c are usually solid

 Chemistry of volatile oils:

Volatile oils consist of Terpenes – are natural products whose structures may be divided into
isoprene units. Serves as basis for the classification of compounds.

• Classification of terpenes:

1. Monoterpenes – composed of 2 isoprene units

 and have the mole formula: C H
10 16

2. Sesquiterpenes – contain 3 isoprene units (C H )

15 24
3. Diterpenes – have 4 isoprene units (C H )
20 32
4. Triterpenes - composed of 6 isoprene units

(C H )
30 48

Divisions in w/c volatile oils and volatile-containing drugs are placed:

1.Hydrocarbons – turpentine oil, rectified turpentine oil, terpene hydrate or terpinol

2. Alcohols – peppermint oil, menthol

3. Aldehydes – cinnamon, lemon peel/oil
4. Ketones – camphor, spearmint
5. Phenols – thymol, clove
6. Phenolic ethers – nutmeg oil or myristica oil 7. Oxides – eucalyptus oil
8. Esters – gaultheria oil

Plants containing volatile oil: see attached.

• Resins and Resin Combination

 -  Oxidative products of volatile oils

 -  Burn with characteristically smoky flame
 -  Forms: oleoresin, oleo-gum-resin, glucoresin, resin alcohol,
  -  Soluble in organic solvents
 -  Final products in destructive metabolism

Resin and resin combinations – compounds comprising resin, oleoresins, oleo gum resins, and
balsams.

• Resins – solid or semisolid amorphous products of complex chemical nature, rosin,

podophyllum resin, jalap resin.

• Oleoresins – resins and volatile oils in homogeneous mixtures: turpentine, copaiba

• Oleo-gum-resins – oleoresins and gums in homogeneous mixtures: asafetida, myrrh.

• Balsams – resins with mixtures of aromatic substances such as benzoic acid, cinnamic acid, or
both: benzoin, tolu balsam, peru balsam, styrax.

• Resin

a) Rosin

SN: Pinus palustris

-shiny, sharp, angular fragments, translucent & amber in color

CN: Abletic acid

Uses: adulterant for resinous products, stiffening agent in plasters

b) Podophyllum

BO: Podophyllum peltatum

CN: Podophyllum, peltatin, teniposide (etoposide) – antineoplastic

: American mandrake, American mayapple : European mandragora

c) Eriodictyon
BO: Eriodictyon californicum Use: masks bitterness

d) Jalap
BO: Exogonium purga CN: Jalapin, Ipurganol Use: Cathartic
e) Mastic
BO: Pistacia tentiscus Uses: dental varnish

f) Kava-kava
BO: Piper methysticum
Uses: skeletal muscle relaxant

g) Cannabis
BO: Cannabis sativa
Resin: hashish
CN: (-)-trans-Δ9-tetrahydrocannabinol – most active

euphoric component

2) Oleoresins
a) Turpentine
SN: Pinus palustris Use: counter-irritant

b) Capsicum
BO: Capsicum frutescens -African chillies

C. anuum var. conoides – tabasco pepper

C. anuum var. longum - Louisiana long pepper

C. capsaicin

c) Ginger
BO: Zingiber officinale
CN: Zingerone, Shogaol - pungency

Zingeberaceae Bisabolene

d) White pine
BO: Pinus strobus Use: expectorant CN: weymouth pine

e) Copaiba –balsam of copaiba

BO: Copaifera spicatta
- Contains neither benzene nor cinnamic acid - Not a true balsam

Peru Balsam – not an ingredient in compound benzoin tincture

3) Oleogumresins

a) Myrrh
SN: Commiphora molmol – available in 2 commercial var.

Use: ingredient in mouthwash (astring-osol) CN: Arabian or Yemen myrrh

African or Somali Myrrh

b) Asafetida
BO: Ferula foetida Devil’s dung

4) Balsams

-resinous mixtures that contain large proportions of benzoic acid, cinnamic acid or both or
esters of these acids

a) Storax
SN: Liquidambor orientalis – Levant

L. Styriciflua - American

CN: α- storesin – amorphous but forms a crystalline compound with potassium

β-storesin – whiteflakes do not form crystalline compound with K, cinnamic acid

b) Peru Balsam
SN: Myroxylon pereirae
CN: Cinnamen – benzyl cinnamate & benzyl benzoate Uses: local protectant , antiseptic,
parasiticide

c) Tolu balsam
SN: Myroxylon balsamum
CN: toluresinotannol cinnamate

Use: pharmaceutic aid for cpd benzoin tincture, flavorant in chewing gum

d) Benzoin

SN: Styrax benzoin – Sumatra benzoin – yield 75% alcohol soluble extractive

S. Tonkinensis – Siam benzoin yield 90% alcohol soluble extractive

CN: Coniferyl benzoate – Sumatra

Cinnamic acid – Siam benzoin

st
Benzoic acid – 1 obtained by sublimation from Sumatra benzoin
- w. salicylic acid – whitfield’s ointment

e) Compound benzoin tincture Ingredients: Benzoin

Storax
Tolu balsam Aloe

Use: topical protectant, expectorant when vaporized

Alkaloids

Definition
 Alkaloids are basic nitrogen containing compounds. They are generally obtained from plants,
animals and microorganisms and often demonstrate a marked physiological action

History
 The isolation of morphine from opium by the German Pharmacist Friedrich Serturner (1783-
1841); in 1805 series of isolation of other active materials from medicinal plants by French
Pharmacist Joseph Caventou (1795-1877) and Joseph Pelletier (1788-1842) combined their
talents and isolated quinine and cinchonine from cinchona and strychnine and brucine from
Nux vomica. Pelletier together with Pierre Robiquet (1780-1840) isolated caffeine and Robiquet
independently separated codeine from opium. Contemporary example drug containing alkaloid
isolated from natural source include vincaleukoblastine an antineoplastic drug from Vinca
rosea.

ALKALOID DESCRIPTION
 Contains nitrogen -usually derived from an amino acid.
 Bitter tasting, generally white solids (exception -nicotine is a brown liquid).
 They give a precipitate with heavy metal iodides.
 Caffeine, a purine derivative, does not precipitate like most alkaloids.
 Alkaloids are basic -they form water soluble salts. Most alkaloids are well-defined crystalline
substances which unite with acids to form salts. In plants, they may exist
 in the free state,
 as salts or
 as N-oxides.
 Occur in a limited number of plants. Nucleic acid exists in all plants, whereas, morphine exists
in only one plant species .

 Earliest alkaloids
 1. Nicotine-1803 ----Tobacco
 2. Morphine-1806 & 1816—Opium  3. Strychnine-1817
 4. Emetine—1817--- ipecac
 5. Brucine-1819 ---
 6. Piperidine– 1819
 7. Caffeine 1819--Coffee
 8. Quinine 1820--Cinchona
 9. Colchicine 1820
 10. Coniine -1826-Hemlock
Coniine - 1826 was the first to have its structure established .It was done by Schiff in1870 and
synthesized by Ladenburg in 1889

TESTS FOR ALKALOIDS

 Most alkaloids are precipitated from neutral or slightly acidic solution by
 Dragendorff's reagent (solution of potassium bismuth iodide)orange coloured precipitate.
 Mayer's reagent (potassio mercuric iodide solution) Cream coloured precipitate.
 Wagner’s reagent (iodine in potassium iodide) red-brown precipitate
 Hagers reagent (picric acid) yellow precipitate
 Caffeine does precipitate

 Tests for alkaloids

 Precipitation tests with reagents
 Mayer’s - mercuric potassium iodide (MAMEKI) most sensitive test for alkaloids
 Hager’s – saturated solution of picric acid / trinitrophenol test solution
 Wagner’s- iodine in potassium iodide (WIKI)
 Dragendorff ’s-solution of bismuth potassium iodide (BIKI)
 Valser’s – HgI2 (VMI)
 Marme’s cadmium potassium iodide (MarCadKI)
 Sonnenchein’s – phosphomolybdic acid (PMA)
 Scheibler’s – phosphotungstic acid (PTA)
 Gold compound
 Tannic acid

*Caffeine (a purine derivative ) does not precipitate with above reagents , hence it is detected
by mixing the alkaloid material with small amount of Potassium chlorate and a drop of
hydrochloric acid Purple color is obtained after evaporation of ammonia
 Functions of Alkaloids
 Poisonous agents protecting the plant against insects and herbivores
 End products of detoxification reactions representing a metabolic locking up of compounds
otherwise harmful to the plants
 Regulatory growth factor
 Reserve substance capable of supplying nitrogen or other elements necessary to the plant’s
economy

Chemical classification
 True (Typical) alkaloids that are derived from amino acids and have nitrogen in a heterocyclic
ring. e.g Atropine
 Proto alkaloids that are derived from amino acids and do not have nitrogen in a heterocyclic
ring. e.g Ephedrine
 Pseudo alkaloids that are not derived from amino acids but have nitrogen in a heterocyclic
ring. e.g Caffeine
 False alkaloids are non alkaloids give false positive reaction with alkaloidal reagents.

OCCURRENCE, DISTRIBUTION& LOCATION OF ALKALOIDS

 Occur in bacteria(Pseudomonas aeruginosa) and rarely in fungi (pscilocin from hallucinogenic
mushrooms).
 Some alkaloids occur in several genera from different species (caffeine), but most occur in
closely related species.
 Some occur in certain families (hyoscyamine), while others occur only in a specific species
(morphine).
 Rarely do plants contain more than 1 type of alkaloid.
 All alkaloids of one plant will have a common biogenenetic origin

• Alkaloids occur in all plant parts, but are usually localized in one organ (e.g. the bark or
seeds).
• Within the plant, [alkaloid] can vary widely from part to part –some parts may contain no
alkaloids.
• Occasionally, different alkaloids also form in different parts of the plant.
• Alkaloid concentrations occur in wide ranges –e.g. Madagascar periwinkle contains 3g per
(anti- cancer) alkaloids per tonne of leaves.

Typical alkaloid is derived from:

•plant source: They are basic
They contain one or more nitrogen atoms.
Have a marked physiological action either on man or on animal.
Animals all have been reproduced in the laboratory
•Fungi by chemical synthesis
•Bacteria

Alkaloids occur in various parts of the plant:

a.Seeds – physostigma, areca b.Fruits – conium
c.Leaves – belladonna, coca d.Roots – belladonna root e.Rhizomes and roots – ipecac,
hydrastis
f. Barks – cinchona
g.Fungi – ergot, Amanita citrina

PH YSICAL-CHEMICAL PROPERTIES OF ALKALOIDS

 MW: 100 –900
 Most bases which do not contain O2 are liquid at room temperature (nicotine), while those
that do are solids. In rare cases they are coloured.
 Most solid bases rotate the plane of polarized light, have high melting points.
 Normally are not soluble in water (occasionally slightly soluble).
 Soluble in a polar or slightly polar organic solvents. Soluble in concentrated hydroalcoholic
solutions

 The basicity of alkaloids depends on the availability of the lone pair of e-on the N2 atoms: e-
donating groups enhance basicity, while e-withdrawing groups decrease it.
 Because some alkaloids have a carbonyl group on the amide, they can also be neutral
(colchicine & piperine).
 Basic characteristic renders complex alkaloids unstable, so that in solution they are sensitive
to heat, light & oxygen.
 Basic character of alkaloids also allows them to form salts with mineral acids (such as
hydrochlorides, nitrates and sulphates) or inorganic acids (tartrates, sulfamates).
 Alkaloid salts are soluble in water and dilute alcohols.
 Solid salts can be conserved well and are a common commercial form of alkaloids.

NAMING OF ALKALOIDS
Numerous methods can be used to name alkaloids 1-Generic plant name –atropine from Atropa
belladonna 2-Specific name of the plant –cocaine from Erythroxylum coca. 3-Common name of
the herb –ergotamine from ergot (rye) 4-Physiological action of the plant –emetine producing
emesis
5-Other –e.g. morphine derived from ancient Greek mythology – Morpheus –god of dreams

EXTRACTION OF ALKALOIDS
 Extraction is based on the basicity of alkaloids and on the fact that they normally occur in
plants as salts (i.e.: on the solubility of bases and salts in water and organic solvents).
 Herbs often contain other materials which can interfere with extraction such as large amounts
of fat, waxes, terpenes, pigments and other lipophilic substances (e.g by forming emulsions) –
avoided by defatting the crushed herb (using petroleum ether and hexane.
 Extraction method normally depends on the raw material, the purpose of extraction & the
scale on which is to be performed.
 For research purposes: chromatography allows for quick and reliable results.
 If larger amounts of alkaloids need to be extracted, one of the following methods can be
used.

GENERAL METHOD
• Powdered, defatted herb is mixed with an alkaline aqueous solution.
• Free bases are then extracted with organic solvents.
• Normally aqueous ammonia is used, but a carbonate solution is used when alkaloids contain
fragile elements such as a ester or lactone.
• In some cases, e.g. Cinchona bark, a mixture of calcium hydroxide & sodium hydroxide should
be used as the alkaloids are bound to tannins.
• Organic solvent: chloroform, dichloromethane or ethyl acetate – depends on the toxicity,
safety, cost & ease of recovery and recycling of the solvent).

Step II
  Organic solvent containing alkaloids (bases) is separated from residue & concentrated by
distillation under pressure if needed.
 Solvent is stirred with an acidic aqueous solution: alkaloids go into the solution as salts.
Impurities remain in the organic phase.

• Aqueous solution of alkaloid salts is washed with an apolar solvent (hexane)

• Alkalinized with a base using an organic solvent not miscible with water.
• Alkaloids precipitate and dissolve in the organic phase.
• Extraction of aqueous phase continues till all alkaloids have moved into the organic phase
(tested when Mayer’s reaction on the aqueous phase becomes negative).
• This purification step may be carried out in a separation funnel or in centrifugal extractors

 Step III
 Organic solvent containing alkaloid bases is decanted, freed from water traces (drying over
anhydrous salt e.g. sodium sulphate) and evaporated under reduced pressure.
 A dry residue remains: total basic alkaloids.

Extraction of liquid alkaloids

2 Methods possible
1-Plant powder is extracted directly with acidified water
2-Plant powder is extracted with acidified alcoholic or a hydroalcoholic solution. This is then
followed by distillation under vacuum (eliminates that alcohol, leaving behind and acidic
aqueous solution of alkaloid salts)

Classification of Alkaloids
1. Biological origin
Sedatives : Morphine
Vasodilatation : Ephedrine, Ergonovine . Local anesthetic : Cocaine
Hallucinating : Mescaline, Psilocybin.

2-Biosynthetic pathway
Ornithine- Tropane, Pyrrolidine, Pyrrolizidine Tyrosine-Benzyl isoquinoline
Tryptophane- Indole alkaloids, Quinoline Pyridine- Pyridine
Lysine- Quinolizidine, Piperidine

3- Chemical classification
 True (Typical) alkaloids that are derived from amino acids and have nitrogen in a heterocyclic
ring. e.g Atropine
 Proto alkaloids that are derived from amino acids and do not have nitrogen in a heterocyclic
ring. e.g Ephedrine
 Pseudo alkaloids that are not derived from amino acids but have nitrogen in a heterocyclic
ring. e.g Caffeine
 False alkaloids are non alkaloids give false positive reaction with alkaloidal reagents.
A. Proto alkaloids
 These are also called Non heterocyclic or Atypical alkaloids or Biological amines.
 These are less commonly found in nature.
 These molecules have a nitrogen atom which is not a part of
any ring system.
 Examples of these include ephedrine, colchicine, erythromycin and taxol etc.
 Table below shows the chemical structure and biological significance of these compounds:

Name
Structure
Biological Significance
Ephedrine
Adrenergic agent- used for asthma and hay fever
Colchicine
Relieves gout
Erythromycin
Antibiotic

Taxol (Paclitaxel)
Used in the treatment of ovarian cancer, breast cancer and non-small cell lung
cancer

B. Heterocyclic Alkaloids or Typical Alkaloids:

 Structurally these have the nitrogen as a part of a cyclic ring system.
 These are more commonly found in nature.
 Heterocyclic alkaloids are further subdivided into 14 groups based on the ring structure
containing the nitrogen

No. Heterocycle Example

1.
Pyrrole and Pyrrolidine
Hygrine, Stachydrine
Pyrrolizidine
Senecionine, Symphitine, Echimidine, Seneciphylline
2.

Pyridine and Piperidine

Quinoline
Quinine, Quinidine, Cinchonine, Cinchonidine
Lobeline, Nicotine, Piperine, Conine, Trigonelline
3.
Tropane (piperidine/N-methyl- pyrrolidine)
Cocaine, Atropine, Hyoscyamine, Hyoscine
4.
5.

Isoquinoline
Morphine, Emetine, Papaverine, Narcotine, Tubocurarine, Codeine
6.
Aporphine (reduced isoquinoline/naphthalene)
Boldine
7.
Quinolizidine
Lupanine, Cytisine, Laburnine, Sparteine
8.

Indole or Benzopyrole
Imidazole or glyoxaline
Pilocarpine, Pilosine
Ergometrine, Vinblastine, Vincristine, Strychnine, Brucine, Ergotamine, Yohimbine,
Reserpine, Serpentine, Physostigmine
9.
Indolizidine
Castanospermine, Swainsonine
10.
11.

Purine (pyrim idine/im idazole)

Caffeine, Theobromine
Steroidal (some combined as glycosides)*
Conessine, Solanidine
T erpenoid*
Aconitine, lycaconitine, Aconine
12.
13.
14.
*Note- Steroidal and terpenoid classes are also treated as separate classes or along with
glycosides.

• HORMONES – are mammalian metabolites produced by endocrine or ductless glands,

released directly into the blood, and are involved in eliciting responses by specific body organs
and tissues.
- either steroidal or derived from amino acids.
- non-peptide metabolites known are epinephrine and thyroxine
Historical development
- Present therapeutic use of endocrine products is an outgrowth organotherapy (use of organic
substances derived from plants and animals). of the primitive practice of
- During the 13th century, Magnus utilized powdered hog testis to treat male impotence and
rabbit uterus to treat female sterility.
- The basic philosophy for the use of mammalian organs was expressed by Vicary during the
16th century, stating:“in what part of the body the faculty you would strengthen lies, take the
same part of the body of another creature in whom the faculty is strong, as a medicine.”
- Standardized powdered glands and glandular extracts provided more reproducible effects and
better therapeutic control than randomly selected glands.

- modern technology has permitted the ready synthesis of many hormones including a number
of peptides and the preparation of substances that mimic the actions of natural hormones (e.g.
prednisone-cortisone);
- A more precise comprehension of their physiologic functions and improved diagnostic
procedures have contributed significantly to therapeutic advancement.

• Hormones function as a chemical transmitters of selective stimuli between the various

endocrine glands and specific body organs and tissues.
• Hormones that control membrane permeability, either directly or indirectly include:
1. estrogens
2. growth hormone
3. glucagon
4. glucocorticoids
5. insulin
6. testosterone
7. vasopressin

• Physiologic control of hormone formation or release to regulate hormone level - is a vital

aspect of maintaining metabolic homeostasis and integrity of body function.
• Two general regulatory mechanisms currently recognized are:
a. Feedback mechanism – responds to change in concentration of some substance in the blood.
e.g. an increase in blood glucose in normal persons stimulates the release of insulin, and
increased levels of triiodothyronine-thyroxine cause a decrease in thyrotropin secretion owing
to an inhibition of the secretion of thyrotropin-releasing factor by the hypothalamus.

b. The second mechanism involves external stimuli and is mediated by the hypothalamus; the
hypothalamus secretes releasing factors that act on the anterior pituitary to increase the
release of specific tropic hormones.
*disturbance in the function of the endocrine gland may take the form of excessive activity
(hyperfunction) or diminished activity (hypofunction), to any degree.

*use of hormones for replacement purposes is usually long-term therapy, and because these
potent substance are normal body metabolites, serious side-effects are usually minimal if
caution is taken to balance the administered dosage with replacement needs.
e.g. insulin utilization provides a good example of this type of approach to a hypofunctioning
endocrine system.

 Endocrine products are by-products of the meat- packing industry w/c includes: thyroid,
pancreas, adrenal and pituitary glands of bovine and porcine origin.
 Endocrine glands are technically fresh meat and must be processed in a manner that prevents
deterioration.
The glands are subjected to extraction and fractionation treatments to yield purified
hormones.
 Frozen thyroid gland is simply dehydrated, defatted, powdered, standardized and made into
suitable dosage forms.

1. Adrenal glands
Adrenals (suprarenals) in humans are a pair of small glands; one is situated over the superior
medial aspect of each kidney. Each average gland measures 5 x 25 x 50mm; together, the
adrenals weigh 4 to 18g.
- First described by Eustachio in 16th century
- functions in the inhibition of fetal urination and in
the prevention of renal stones in adult.
Composition: each adrenal consists embrologically, histologically, and functionally of 2 distinct
glandular entities that are grossly combined into one organ.

- Cells of the adrenal cortex secrete steroid hormones.

- The adrenal medulla is composed of cells that migrated out from the embryonic neural crest.
Secretes epinephrine and norepinephrine (ratio of 17:3) and functions as a sympathetic
postganglionic structure.
- Epinephrine elicits vasoconstrictor and vasopressor responses, acting in general as a
sympathomimetic agent of rapid onset but brief duration of action. Administered by IV or
intramyocardial inj. in cardiac arrest.

 Bronchodilation resulting from epinephrine’s beta- receptor adrenergic activity is useful in

alleviating acute asthmatic attacks.
Biosynthesis of epinephrine:
- Epinephrine is an alkaloidal amine of the
phenylpropanoid type, derived from tyrosine.
- Tyrosine is oxidized to dihydroxyphenylalanine (dopa), which is decarboxylated and oxidized in
the side chain. The norepinephrine produced is converted to epinephrine by transfer of a
methyl group from active methionine. The rate-limiting step appears to be the conversion of
tyrosine to dopa.

• Related products:
1. Epinephrine – (-)-3,4-dihydroxy-α[(methylamino)
methyl] benzyl alcohol.
- Isolated as a hormone from adrenal medulla or may be prepared synthetically.
- Occurs as a white to nearly white, microcrystalline, odorless powder that gradually darkens
when exposed to light and air.
Prescription products: Adrenalin, Epifrin, Eppy/N, Epitrate, Glaucon, and Sus-Phrine

•
a.
b. c.
•
Proprietary products: Adrenalin, Asthmal Nefrin, Bronitin-Mist, Bronkaid Mist, Medihaler-Epi,
Primatane Mist, and Vaponefrin.
Incorporation of epineprhine to various pharmaceutic formulations for therapeutic utilization
such as:
Solubilization of epinephrine in aqueous prep’ns using HCl or tartaric acid (bitartrate) to form
water-soluble borate complex used in Ophthalmology.
1:1000 aqueous solution of epinephrine for topical purposes;
1:100 aqueous sol’n for inhalation, metered-dose aerosol products

c. Sterile aqueous solution (1:1,000; 1:10,000; and 1:100,000) for parenteral administration
d. A sterile 1:200 suspension in oil for prolonged systemic action and several ophthalmic
solutions (1:50 to 1:400) for use in open-angle glaucoma and other ophthalmic purposes.
2. Levarterenol – or (-)-norpinephrine – is (-)-α- (aminomethyl)3,4-dihydroxybenzyl alcohol.
- Used as bitartrate salt, w/c is a white or faintly gray, crystalline powder, slowly darkens when
exposed to air and light.

Uses: a sympathetic stimulant, contains dominant alpha-receptor adrenergic activity. A strong

peripheral vasoconstrictor and especially useful in the restoration of blood pressure in acute
hypotensive situations.
Usual dose: administered via IV infusion. The equivalent of 4mg of levarterenol is placed in
1000mL of 5% dextrose injection and infused at a rate adjusted to maintain blood pressure.
Prescription product: Levophed

3. Dopamine or 3,4-dihydroxyphenyl-ethylamine
- A biosynthetic precursor of norepinephrine and epinephrine w/c posesses sympathomimetic
properties.
- Acts directly to stimulate alpha and beta-1 receptors and indirectly by causing the release of
stored norepinephrine.
- Used to treat cardiac decompensation administered by IV infusion.
- Initial infusion rates are 0.5 to 5μg per kg of body weight per minute.
Prescription product: Dopastat, Intropin

2. Thyroid gland
- Consist of 2 lobes that are lateral and inferior to the anterior aspect of the larynx and are
connected across the larynx by an isthmus to produce a U- shaped structure averaging 30g in
weight.
- Its identity as a ductless gland was first described by Holler in 1776.
- Roger of Palermo used sponges and seaweed high in iodine content in the treatment of goiter
(thyroid enlargement) in the 12th century.
- It mobilizes dietary iodine converting it to an organic compound that accelerates metabolic
processes.

 Manifestations of hypothyroidism may be caused by an iodine deficiency and a resulting lack

of precursor moities for the hormonal substances (simple hyperplastic goiter, char. by a
compensatory enlargement of the gland); by a deficiency of thyrotropic factors, or by other
metabolic irregularities.
 The first two causes may be corrected by adding iodine to the diet or administering
thyrotropin.
 A hypothyroid condition results in some degree of Cretinism in infants and myxedema in
adults.
Cretinism – char. by retarded and abnormal growth; arrested sexual development; mental
deficiency;

Con’t..... cretinism
- thickened, dry skin; thickened tongue; coarsened features; and a fall in the metabolic rate.
- The features of myxedema include general lethargy, retarded mental processes, increased
body fat, susceptibility to cold and fatigue, cardiac dilatation, dry, thickened skin, and
coarsened features with a thickened protruding tongue.
*thyroid hyperactivity results in thyrotoxicosis char by increased heart rate, blood pressure,
nervous excitability, and metabolic rate; muscular weakness with tremor; loss of body weight
and fat; and an increased tolerance to cold but intolerance to heat.

 When accompanied by protrusion of the eyeballs (exopthalmos), the condition is known as

exopthalmic goiter (Grave’s or Basedow’s disease).
 The course of the disease is marked by occasional crises or ”storms,” which may result in
abrupt death.
 Treatment of organic hyperthyroidism is principally surgical, aided by radioactive iodine and
by antimetabolites such as propylthioracil.
Preparation of thyroid hormones are useful for replacement therapy in cretinism or
myxedema.

 Are also employed to prevent myxedema in cases when the thyroid gland must be surgically
removed.
 Biosynthesis of Thyroid Hormone. The first stepin the biosynthesis is a peroxidation of iodide
to “active iodine” which then reacts with tyrosine to first form 3-monoiodotyrosine and
subsequently3,5-diiodotyrosine.
 Two molecules of the latter compound react to form thyroxine.
 Alternative, a molecule of the diiodotyrosine may react with a molecule of monoiodotyrosine
to form triiodothyronine (liothyronine), which is then iodinated to yield thyroxine.
 Deiodination –is the major catabolic pathway for thyroxine and triiodothyronine.
The β-glucuronide is the major of conjugation product of thyroxine, but the sulfate ester is
more common for triiodothyronine.
Thyroid- is the cleaned, dried, and powdered thyroid gland previously deprived of connective
tissue and fat.
 - is obtained from domesticated animals that are used for food by humans.

Thyroid contains not less than 0.095% and not more than 0.125% of total thyroxine and
triiodothyronine, and the ratio of thyroxine to triiodothyronine is not less than 5.
 USE AND DOSE. Thyroid is effective in oral therapy. The usual dose is 15 to 180 mg daily. The
effect of a single dose of thyroidorally, or of thyroxine orally or intravenously, is not manifest
for some 24 to 48 hours; it reaches a maximum in 8 to 10 days and decreases slowly over a
period of several weeks. Hence, accumulation may occur, and dosage schedules must be
adjusted individually to the needs of the patient.

PRESCRIPTION PRODUCTS. S-P-T®, Thyrar®, and

thyro-Teric®.
Thyroglobulin – is obtained by fractionation of procine thyroid gland. It contains thyroxine and
triiodothyrine in ratio of not less than 2.8.
 The source is restricted - Sus scrofa Linne var. domesticusi Gray (Fam. Sudae) because the hog
accumulates especially high levels of the thyroid hormones and has a higher proportion of
triiodothyronine.

 USE AND DOSE. Thyroglobinis used in essentially the same manner as thyroid. The usual daily
dose is 16 to 200 mg.
PRESCRIPTION PRODUCT
 Sodium levothyroxine - is the sodium salt of the levo isomer of thyroxine, an active
physiologic principle obtained from the thyroid gland of domesticated animals used for food for
by humans. It can also be prepared synthetically.

USES AND DOSE

Sodium levothyroxine is classed as a thyroid hormone. It is used for replacement therapy of
reduced or completely absent thyroid function (manifested as myxedema, cretinism,and mild
forms of hypothyroidism).
PRESCRIPTION PRODUCTS
 Levothroid, Synthroid, Synthrox,and Syroxine.

 SODIUM LIOTHYRONINE – is the sodium salt of the levoratory isomer of 3,3`,5-

triiodothyronine. This physiologically active compound is a naturally occuring thyroid hormone,
but quantities needed for commercial purposes are provided by chemical synthesis.
USE AND DOSE. Sodium liothyronine is used for the same purposes as sodium levothyroxine.
Liothyronine, compared to other tyroid agents, has better gastrointestinal absorption, a more
rapid onset of action, and a shorter duration of action. The usual dose is the equivalent of 5 to
100 μg of liothyronine, once a day.
 Liotrix – is a 4:1 mixture of synthetic sodium levothyroxine and sodium liothyronine. The
effects of this mixture are claimed to resemble closely those of endogenous thyroid secretion
and to give laboratory protein-bound iodine test results that are more consistent with clinical
response than are the results obtained with other preparations. However, recognition of the
conversion of thyroxine to triiodothyronine in peripheral tissues raises questions about any
theraupic advantage of this mixture over its individual components.

Sodium dextrothyroxine – is the salt of the synthethically prepared dextrorotatory isomer of

thyroxine. This substance is effective in a high dose (up to 8 mg daily) for the treatment of
hypothyroidism, but its occasional use to patients with cardiac disease who cannot tolerate
thyroid medications.
 Detrothyroxine also reduces serum cholesterol and low indensity lipoproteins, and it has been
classed a hypocholesterolemic agent. Its greatest therapeutic utility is in this area, but patients
must be monitored carefully for ischemic myocardial changes and other adverse reactions.

PITUITARY
 The human pituitary gland hypophysis is situated in a small cavity in the sphenoid bone at the
base of the skull and is attached to the base of the brain by a short stalk. It weighs about
0.5g.galen considered it a strainer for spinal fluid, and Vesalius later thought it was the source
of mucus, lubricating the nasopharynx. Pituitary is from the Latin pituita, meaning slime or
mucus.

1.
The pituitary body is in reality 2 glands by origin and function:
The anterior lobe is ectodermal in origin- derived from an out pounching from the primitive
pharnyx.
The posterior lobe is neural in origin – derived from an outpounching of the base of the brain.
2.

Posterior Pituitary
Extracts of posterior pituitary lobe exhibit the following effects in experimental animals and in
humans.
1. A pressor effect, owing to arteriolar and capillary vasoconstriction;
2. Direct stimulation of smooth muscle, seen in the intact animal or in preparations of isolated
muscles;
3. An antidiuretic action, effected by increasing the tubular and collecting duct resorption of
water in the kidney.

Oxytocin (α-hypophamine)
– is the uterine-stimulating fraction, and it is relatively free from action on other smooth
muscle. It is especially active on the pregnant uterus, which has been sensitized by estrogens.
- appears to increase the permeability of uterine cell membranes to sodium ion with an
effective augmentation of the contracting myofibrils.
 Vasopressin (β-hypophamine)
- is the antidiuretic principle; the pressor effects of this hormone are observed only when large
quantities are administered.
- regulates the threshold for resorption of water by the epithelium of the renal tubules.
 Hormones - is released into the blood when osmoreceptors in the hypothalamic nuclei detect
an increased blood volume. The resulting fluid conservation contributes to maintenance of
homeostasis.
 Oxytocin by using chickens or the isolated uterus of nulliparous guinea pigs and vasopressin
by using rats.

 Vasopressin injection – is a sterile solution in water for injection of the water-soluble, pressor
principle prepared by synthesis or obtained from the posterior lobe of the pituitary. Either 8-L-
arginine- vasopressin (beef vasopressin) or 8-L-Lysine- vasopressin (hog vasopressin) meets
monographic requirements.
- It is used to control neurohypophyseal diabetes insipidus but is ineffective in the nephrogenic
form of the disease.
- used as a peristaltic stimulant in postoperative ileus and to control acute hemorhage in the
gastrointestinal tract and esophagus.

 Lypressin or lysine-vasopressin – is a synthetically prepared peptide hormone that occurs

naturally in the posterior lobe of the hog pituitary gland.
- It has the properties of causing the contraction of vascular and other smooth muscles and of
producing antidiuresis.
 Depression or 1-deamino-8-D-arginine- vasopressin – is a synthetic analog of arginine-
vasoprissin. It possesses very little of the undersirable pressor effect of the parent hormone and
has a relatively long duration of action.

 Desmopressin – is used for the same purposes as vasopressin and is available as an injection
and a nasal solution. The usual parenteral dosage for diabetes insipidus is 2 to 4 μg daily in 2
divided doses.
 Oxytoxin – is a synthethically prepared peptide hormone that occurs naturally in the posterior
lobe of the pituitary gland. Glandular material is no longer used as a commercial source of this
hormone.

- The oxytoxic principle – is available as an injection for induction of labor for medical
indications (use for elective induction is in appropriate) and for control of postpartum
hemorrhage. A nasal spray is available to promote milk ejection on the infrequent occasions
when this is a problem in breast feeding.

Anterior Pituitary
the anterior lobe of the pituitary exerts a profound influence on the growth and development
of the body and on its sex characteristics through its stimulating actions on the other endocrine
glands. The Anterior Pituitary has been referred to as the “master gland,” the “conductor of the
endocrine symphony.” Primary disturbances in anterior pituitary function may result in
widespread endocrine involvement and generalized secondary disturbances. Therapy in such
complex situations is far from simple and is associated with unusual potential for undesirable
side effects. Effective therapeutic utilization of the hormones of the anterior pituitary is still in
an early stage of development.

Adrenocorticotropin, ACTH,or cortocotropin – is a straight-chain polypeptide containing 39

amino acid residues. A portion of the peptide molecule with 20 amino acid residues has the full
biologic activity of this hormone. Corticotropin injection is a sterile preparation of the peptide
hormone that is derived from the anterior lobe of the pituitary of mammals used for food by
humans and that exerts a tropic influence in on the adrenal cortex. Its tropic effects involve
primarily glucocorticoids. Corticotropin may be used in collagen disease, particularly in
rheumatoid arthritis and acute rheumatic fever, when the adrenal cortex is functional.

 Cosyntropin (Controsyn) – is a synthetically prepared peptide subunit of corticotropin and is

used as a diagnostic aid in suspected adrenal insufficiency. It contains 24 amino acid residues
and presents a lesser risk of allergic reactions than the natural hormone.
 Chorionic gonadotropin (HCG or choriogonadotropin) – is a gonad stimulating polypeptide
hormone obtained from the urine of pregnant women. This anteriorpituitary like substance
resembles LH in its response and is used as replacement therapy to stimulate descent of the
testes in cryptorchidism and to stimulate

the development of interstitial cells of the testes in delayed adolescence and hypogonadotropic
eunuchoidism.
 The major indication for withdrawal of therapy or reduction of dosage is sexual
precociousness.
 Gonadorelin – is a synthetic decapeptide that is identical to the gonadotropin-releasing factor
of the hypothalamus. It is used diagnostically in suspected gonadotropin deficiency to evaluate
thefunctional capacity and response of the gonadotropes of the anterior pituitary. The test in
females should be conducted in the early follicular phase of the menstrual cycle. The usual test
dose is 100 μg intravenously or subcutaneously.

 Somatropin, somatotropin, or growth hormone influences a number of essential growth

processes. It stimulates linear growth of bones during development, and its anabolic effects
include an increased intracellular transport of amino acids and a net body retention of nitrogen,
phosphorus, and potassium. Hypofunction of the growth- stimulating activity in children results
in the pituitary dwarf; in adults, such deficiency often produces an increased delicacy of
structure, referred to as acromicria.

 Thyrotropin – is the thyrotropic principle of the anterior pituitary. A glycoprotein the 28,000
to 30, 000 molecular weight range, it is obtained from bovine glands and is purified to remove
significant amounts of corticotropic, gonadotropic, and other hormones. Theoretically, it can be
used in replacement therapy, but it is used primarily as a diagnostic aid in evaluating thyroid
function, including distinction between primary and secondary hypothyroidism, or as
supportive therapy to facilitate the uptake of I treatment of toxic goiter or thyroid carcinoma.
Thyrotropin is available as a lyophilized powder and is administered intramuscularly
orsubcutaneously, usually in daily doses of 10 international units.

 Protirelin - is the synthethic tripeptide, Lpyroglutamyl-L-histidyl-L-prolinamide. Identical to

the thyrotropin-releasing factor from the hypothalamus, it is used diagnostically to assist in
distinguishing secondary and tertiary hypothyroidiam. The usual adult dose is 500 μg given
intravenously.

Pancreas - is an exocrine gland that supplies digestive enzymes to the duodenum. Isolated
groups of cells, the islets of Langerhans constituting about 3% of the gland, produce the
hormonal substances.
 Glucagon – is produced by the α-cells
 Insulin – is formed by the β-cells. Glucagon and insulin, both polypeptide hormones, exert
counterbalancing actions on carbohydrate metabolism in the body.

 Insulin – is a polypeptide with a molecular weight of 5734. it contains 48 amino acid residues
(including3cystine residues) that are arranged in 2 linear chains connected by disulfide linkages.
Insulin tends to form dimeric and hexameric forms, a characteristics that resulted in an initial
estimateof about 35, 000 for the molecular weight of the hormone.

Glucagon for injection – is a mixture of the hydrochloride with one or more suitable, dry
diluents. When the aqueous injection is reconstituted , it has a pH between 2.5and 3.0 and is
usually formulated to contain 1 mg in each mL. The usual parenteral dose is 500 μg to 1 mg,
repeated in 20minutes, ifnecessary.

 Insulin injection or insulin- is a sterile , neutral solution of the active principle of the pancreas
that affects metabolism of glucose. Insulin injection contains 40, 100, or 500 USP insulin units in
each ml. It is a prompt-acting preparation with a peak of action at 2 to 5 hours. This is the
preparation of choice when glucose tolerance fluctuates rapidly; such situations may include
the presence of a severe infection, shock, surgical trauma, or unstable diabetes. Insulin
preparations, including insulin injection , must be labeled to indicate the nature (beef and pork,
beef, pork, or human) of the insulin; when a products meets the standards for purified insulin,
this must also be indicated on the label.

The usual dose, for diabetes acidosis, in travenously is 1 to 2 units per kg of the body weight,
repeated in 2 hours in necessary; for diabetes, 10 to 20 units, subcutaneously, 3 or 4 times a
day according to the needs of the patient.

Protamine zinc insulin suspension or protamine zinc insulin – is a sterile suspension, in a

phosphate buffer, of insulin modified by the addition of zinc chloride and protamine. The
protamine is prepared from the sperm or from the mature testes of fish belonging to the genus
OncorhynchusSuckley, or Salmo Linne (Fam.salmonodae). Protamine zinc insulin suspension
provides 40 or 100 USP insulin units in each ml. It is a prolonged-acting insulin preparation. The
usual dose, subcutaneously, is 7 to 20 units once a day.

 Isophane insulin suspension, isophane insulin, or NPH insulin – is a sterile suspension, in a

phosphate buffer, of insulin made from zinc- insulin crystal modified by the addition of
protamine in such a manner that the solid phase of the suspension consists of crystals
composed of insulin, protamine, and zinc. It provides 40 or 100 USP insulin units in each ml. it is
an intermediate- acting insulin preparation. The usual dose, subcutaneously, is 10 to 20 units, 1
or 2 times a day.

 Insulin zinc suspension or lente insulin – is a type of intermediate-acting insulin preparation.

It consists of a mixture of crystalline and amorphous materials (approximately a 7:3 ratio)
suspended in an acetate buffer. It provides 40 or 100 USP insulin units of each ml. The usual
dose, subcutaneously, is 10 to 20 units, once a day.

 Extended insulin zinc suspension or ultralente insulin – is a sterile suspension, in an acetate

buffer, of insulin modified by the addition of zinc chloride in such a manner that the solid phase
of the suspension is crystalline. It provides 40 or 100 USP insulin units in each ml. It is long-
acting insulin preparation; the duration of action is determined by the particle size and persists
for over 36 hours. The usual dose, subcutaneously, is 7 to 20 units, once a day.

 Prompt insulin zinc suspension or semilente insulin -is a sterile suspension, in an acetate
buffer, of insulin modified by the addition of zinc chloride in such a manner that the solid phase
of the suspension is amorphous. It provides 40 or 100 USP insulin units in each ml. It is a rapid-
acting insulin preparation; however, its duration of action extends from 12 to16 hours. The
usual dose, subcutaneously,is 10 to 20 units,1 or 2 times a day.

PARATHYROID HORMONE AND CALCITONIN – in man are usually 4 in number, oval, 5 to 6 mm

in length, and situated upon or imbedded in the dorsal surface of the thyroid gland. They
develop and function independently of thyroid tissue. For a number of years, after their
discovery by Sandstorm in 1880, the parathyroid were considered to be remnants of embryonic
thyroid tissue.

 Parathyroid hormone (parathyrin) – is a straight- chain polypeptide containing 83amino acid

residues and has a molecular weight of approximately 9500. A portion of the molecule that
contains only 35 amino acids residence can elicit the significant physiologic activity of the
hormone. The essential 35-amino-acid subunit of human parathyroid hormone differs in 5 or 6
of its amino acid residues from the animal parathyroid hormones that are available through the
meat-packing industry. Immunologic recognition of this factor may contribute to the high
incidence of tolerance noted in therapy. The hormone has a hypercalcemic action. Its principal
effect involves bone resorption and calcium release, but it also promotes absorption of calcium
from the gut the renal tubules.

 GASTROINTESTINAL HORMONES
The intestinal mucosa secretes such peptide hormones as cholecystokinin, gastrin, and secretin.
These hormones facilitate digestion by stimulating the release by the gastrointestinal tract or
the pancreas of various enzymes and other exocrine substances. There is no therapeutic
indication for these hormones, but cholecystokinin (CCK) and secretin (Secretin-Kabi and
Secretin-Boots) from porcine duodenal mucosa are used in the diagnosis of pancreatic
disorders. Cholecystokinin is also used as diagnostic aid in chlocystography and
chloangiography.

 Cholecystokinin – contains 33 amino acid residues in a linear chain.

- Stimulates the secretion of pancreatic digestive enzymes, the flow of bile and the contraction
of the gallbladder.
*Secretin – normally increases the bicarbonate content and volume of secretion from the
pancreas.
*Pentagastrin (Peptavlon) - a synthetic pentapeptide with effects similar to natural gastrin,
used for diagnostic purposes.
- Increases GI motility and stimulates the secretion of gastric acid, pepsin and intrinsic factor;
used to test gastric secretory function.

ENZYMES

• Enzymes are biologic catalysts produced by the activity of living organisms as such as plants,
animals, and micro-organisms – and which modify the speed of reaction without being used to
or appearing as one of the end products.

Chemical nature of enzymes

All enzymes isolated and studied were proven to be protein

 enzymes are soluble in water, glycerol and alcohol.

They are precipitated by protein precipitants (alcohol, ammonium sulfate, trichloroacetic

acid) 29-30 26-28

In solution, they are colloidal in nature and are non dialyzable.

Biological importance of enzymes

• Most chemical reactions characteristic of living matter are accelerated by enzymes.

• Enzymes are responsible for the different reactions in living matter: synthesis, oxidation,
hydrolysis, tautomeric changes ( necessary during digestion, metabolism, respiration, energy
release, and energy transfer)
Nomenclature of enzymes

A. Upon the substance they act upon.. Suffix “ase” is added. Ex:

1. amylase 2.maltose 3. cellulase 4.urease 5.lipase

B. Upon the reaction enhanced. Suffix ‘ase ‘ is added. Ex:

1. oxidase
2. decarboxylase
3. transaminase
4. hydrolase
5. hydrase or dehydrase

Classification of enzymes

A. HYDROLASES 1. estrases

2. glycosides
3. peptidase
4. amidase
5. deaminase
6. phosphatases

B.DESMOLASES OR LYASES: enzymes that add or remove sspecific groups from subs:

1. dehydrase, hydrase 2. desulfhydrases 3.decarboxylases 4.deaminases 5.synthases

6.aldolases

C. TRANSFERASES: enzymes that transfer specific groups from one compound to another.

1. transglycolases 2.transamidases 3.transpeptidase 4.transaminases 5.transphhophorylases

6.transmethylases

7. transformylases 8. transacylases 9.transamidinases

10.transaldolases

D.OXIDO-REDUCTASE: enzymes that bring about oxidation and reduction.

1. oxidasess
2. dehydrogenases
3. reluctases
4. flavoprotein transhydrogenases 5. transelectronases
6. hydroperoxidases

a. Peroxidase

b. Catalase 7.hydroxylase

E.LIGASES :enzymes that catalyze bond formation between two substrate molecules.

1. synthetase 2.carboxylase

F. ISOMERASES : catalyzes intramolecular rearrangement.

1. epimerase 2. mutase

Terminologies in eznyme chemistry

   Substrate - the subs. Acted upon by the enzyme

   Zymogen 20 (proenzyme30) - the inactive form of enzyme.
   Activator – subs. 21 That convert the proenzyme into the active enzyme.
   Coenzyme – help or assist in the activation of a chemical reaction.
   Apo-enzyme -29 protein part to which the coenzyme attaches itself.
   Holo-enzyme 22 – combination of apo and co-enzyme.
   Anti-enzyme – subs. That inhibit enzyme activity.

ex: ascaris (intestinal parasite) contains anti-trypsin w/c prevent enzymes from digesting
worm.

Made of protein

Present in all living cells

Enzymes

Biological catalysts

Converts substrates into products

Cells & Enzymes

Increase the rate of chemical reactions

Remain unchanged by chemical reaction

METABOLISM
• This term really means two things:

ANABOLISM and CATABOLISM

ANABOLISM
“ TO BUILD” molecules as in the biosynthesis of polymers..

We ingest food digest to monomers and THEN via ANABOLISM we make larger molecules

Catabolism ...then is to..

• “TOBREAKAPART“

• Example: Glycogen, (starch) stored in the liver when needed for energy, is converted to
glucose ( monomers).

So during catabolism 31 19 large molecules are broken into smaller molecules.

Chemical Reactions

A chemical reaction takes place when one or substances is chemically changed into one or more
different substances.
Chemical reactions take place in cells all the time.

Catalyst

Enzyme

Manganese dioxide

Catalase

Substrate

Product

Hydrogen peroxide

Water + oxygen

Catalysts

A catalyst is a substance which speeds up a chemical reaction, without itself being changed by
the reaction.

1. When a catalyst is present, less energy is needed to get the chemical reaction started.
2. When a catalyst is present, the speed of the chemical reaction is faster.
3. Although a catalyst helps a chemical reaction to happen, it is unchanged at the end of
the reaction.

Biological Catalysts
The biological catalyst present in the cytoplasm of plant and animal cells that speeds up the
breakdown of hydrogen peroxide is called CATALASE.

Hydrogen peroxide

REACTANTS

Catalase 15
Oxygen + water enzyme

PRODUCTS

2.2 Nature of Enzymes

The biological catalyst present in the cytoplasm of plant and animal cells that speeds up the
breakdown of hydrogen peroxide is called CATALASE.

Hydrogen peroxide

Catalase

Catalase cannot speed up any other reaction. It is SPECIFIC to this reaction.

Water + oxygen

One Enzyme – One Reaction

There are thousands of different enzymes in your body.

Why are there so many different enzymes?

Each enzyme has its own unique protein structure and shape, which is designed to match or
COMPLEMENT its substrate.
Different enzymes for different jobs

Enzymes involved in breakdown reactions

Enzyme and substrate separate Enzyme-substrate complex Enzyme and products separate

Enzymes involved in synthesis reactions

Enzyme and substrates separate Enzyme-substrates complex Enzyme and product separate

2.3 Using a Control

Why is it necessary to include a control experiment in an investigation?

A control is an experiment that allows a comparison within an investigation in order to ensure

that the conclusions drawn from the results are valid.

Enzymes involved in breakdown reactions

Hydrogen peroxide Catalase 35 Water + Oxygen

Starch Fat

Protein

Amylase 18 32 Maltose

Lipase 1633 Pepsin 17 34

Fatty acids + Glycerol Amino acids

2.5 Effect of High Temperature

• Optimum conditions are the conditions at which an enzymes works best

• Rate of reactions may be affected by temperature and pH

Enzyme Summary

Enzyme Substrate Product(s) Degradation or synthesis?

Amylase Starch Maltose
Oxygen and
Catalase Hydrogen peroxide
water
Pepsin Protein Amino acids
Glucose-1-
Phosphorylase Starch
phosphate
Lipase Fat Fatty acids

Organic substances, not synthesized within the body, that are essential in small amounts for
the maintenance of normal metabolic functions.
The term vitamins was derived in 1911 when an amine thought to prevent beriberi was isolated
from rice bran; this essential or vital amine was called vitamins.
1. Which of the following vitamins is a precursor of coenzyme A?
a. cobamide b. panthothenate c. thiamine d. riboflavin

2. Which vitamin is formed in the body by exposure to ultraviolet irradiation or

sunlight?
a. vitamin E c. vitamin A b. vitamin D d. vitamin C
3. Free vitamin A does not occur in plants, but in its place are compounds that are converted
into vitamin A in the small animal body. These precursors of vitamin A are called:
a. provitamin B b. neovitamin A c. B-carotene d. b and c

C 4. Which of the following is a precursor of vitamin D? a. prostaglandin c. cholesterol b.

linoleic acid d. aldosterone
C 5. Excess vit. A & D is stored in the body, but excess vit. C & D is readily excreted. What
property shows this? a. vit C & D are water soluble c. both a & b b. vit. A & D are fat soluble d.
none of these
B 6. The vitamin which is used in the prevention of degenerative changes in the central nervous
system. a. vit. A c. vit. C b. vit. B complex d. vit. D

D 7. Deficiency in this vitamins causes red blood cell fragility a. vitamin A c. vitamin D b.
vitamin K d. vitamin E
D 8. What vitamin deficiency causes pellagra? a. riboflavin c. pantothenic acid b. thiamine d.
nicotinic acid
B 9. This vitamin easily undergoes oxidation a. vitamin A c. vitamin B12 b. vitamin C
d. vitamin B1
A 10. Night blindness is a symptom of a deficiency in this vitamin. a. vitamin A c. vitamin B b.
vitamin C d. vitamin D

A 11. The conversion of beta carotene to vitamin A is carried out in the a. liver c. lungs b. small
intestine d. pancreas

Fat-Soluble Vitamins
• Vitamins A, D, E, and K
Water-Soluble Vitamins
• Vitamin B1,B2, B3,B5,B6, B9, B12, and C 12-19

• Retinol is the major natural form of vitamins.

• A yellow to red oily liquid that may solidify when
refrigerated and should be protected from air and light.
Common dietary source: Animal organs (heart, kidney, liver), eggs, dietary products, and fish.
Defficiency: Nyctalopia, xerophthalmia, hyperkeratosis of skin, growth retardation, and
decreased resistance to infection.
Prescription product: Retin-A, Accutane, and Solatene.
 • A term that is used for several related steroids and their metabolites that are essential for
the absorption and utilization of calcium.
Cholecalciferol 20 or vitamin D3 – The primary form of the vitamin encountered in zoologic
species.
Ergocalciferol or vitamin D2- derived form plant steroid. Used to fortify such foods as milk,
bread, and cereals.
• Absorbed readily from small intestine of normal individuals.
• Aids in the utilization of Calcium and Phosphate and is essential to the development and
maintenance of strong teeth and bones.
• Antirachitic vitamin, indicated for prevention and treatment of deficiency states.
• Used to treat familial hypophosphatetemi and hypoparathroidism.
Dietary sources: Butter cream, and liver
Deficiency: Children-Rickets 21 & Adults-Osteomalacia
Prescription products: Delta-D, Deltalin, Calciferol, Drisdol, Calderol, Rocaltrol, DHT, and
Hytakerol.

•
•
•
•
A term that refers to various forms of alpha-tocopherol. 22
Requires bile salts and dietary lipids for efficient absorptions from the
intestinal tract.
Used primarily forprophylactic purpose to prevent deficiency states in conditions in which
reduced absorption is likely.
Stored in adipose tissue of the body.
Dietary sources: Plant oils, green vegetables, whole grains, egg yolks, and meats.
Deficiency: muscular dystrophy, coronary disease, and sterility.
Beneficial effect: Cancer, fibrocystic disease of breast, sickle-cell, and lung
toxicity.
Prescription products: Aquasol E, CEN-E, E-Ferol, E-Vitaal,Epsinal-M, Pheryl-E and Viterra E.

• A term that refers to 2-methyl-1, 4-naphthoquinone 23 and derivatives of this compound

that exhibit an antihemorrhagic activity. 24
• Vitamin K1 ocurs in green leafy vegetables
• Vitamin K2 has a larger aliphatic side chain than Vit. K1.
• Vit. K3 is a synthetic material with Vit K activity
• The lymphatic system is the major means of transporting vit. K to the liver where it tends to
concentrate.
Dietary products: fruits and vegetables Deficiency: Hemmorhagic disease
Prescription product: Konakion, and Mephyton

• Known as Thiamine
• Final steps in both the biosynthesis and chemical synthesis of this vitamin
involve linkage of the two ring system.
• Stable in acidic environment
• Required for carbohydrates metabolism and for neurologic functions.
• Used to supplement an adequate diet.
• Used as the hydrochloride and monoitratesalts and is available in tablet, elixir, and injection.
Dietary sources: whole grains, legumes, and meats.
Deficiency: hypersensitivity, loss of appetite, fatigue, and muscular
weakness)
Prescription products: Betalin S and Biamine

• Known as Riboflavin 25
• A yellow, heat-stable substance that is
slightly soluble in water.
• Treatment for acne, migraine headaches and muscle cramps.
Dietary products: eggs, legumes and meats.
Deficiency: rarely encountered in healthy persons receiving a balanced diet.
Prescription products: Rionin-50

• Known as Niacin, Nicotinic acid

• A simple, naturally occurring pyridine derivative that prevent
pellagra.
• Used for dietary and therapeutic purpose.
• Causes direct peripheral vasodilatation of warmth, especially in the area of face, neck and
ears.
• Used to prevent or treat deficiency conditions. Dietary sources: lean meats, fish and dairy
products
Deficiency: inadequate nutrition, intestinal malabsorption, genetic errors of metabolism.
Prescription products: Niac, Nico-400, Nicobid, Nicolar, Nico- span, Nicotinex, and tega span.

• Also known as Pantothenic acid 26

• A components of vit. N complex that is sometimes known as the “chick antidermatitis factor”
• A viscous, oily liquid, used as the calcium salt.
Dietary sources: Deficiency: Prescription products:

• A term that is applied to pyridoxol, pyridoxal, and pyridoxamine. Term used for pyridoxol in
pharmacy and medicine. Occur in plant materials.
• Used for exogenous dietary supplementation and therapeutic purpose.
• Readily absorbed in the jenunum, but the vitamin synthesized by the microflora
of the colon is largely excreted in feces.
• Available as the hydrochloride salt in tablet, sustained released, and injection.
Dietary sources: Meats, bananas, whole cereal grains, nuts, and potatoes.
Deficiency: neurologic abnormalities, skin lesions, and hhypochromic microcytic anemia.
Prescription products: Beesix, Hexa Betalin, Nestrex, and Vitabee-6
 • Known as folic acid, folacin, and pteroylglutamic acid 44-45 are terms that refer to a
material with antiamenia properties.
• Naturally occurring biochemical metabolite of folic acid that finds special use in an anticancer
drug regimen employing folate antagonist.
• Available as tablet and injection dosage forms.
Dietary sources: Leafy vegetables and liver Deficiency: Megaloblastic anemia
Prescription products: folvite and wellcovorin

 Vitamin B12 and cobalamins 42 are terms that refer to a series of porphyrin-related
corrinoid derivatives that function as extrinsic factors to prevent pernicious anemia.
 Cyanocobalamin – a red crystalline material, is the most stable of the cobalamins; most
frequently utilized in theraphy.
 Hydroxocobalamin – finds some therapeutic use; in the cyano group is replaced with a
hydroxyl substituent.
 Stored in the liver and liver extract has been the classic source of the vitamin.
 Absorbed in the lower half of the ileum.
 Essentials to cell reproduction, growth hematopoiesis, and synthesis of myelin and
nuceoprotein.

 Unicellular organisms that are well-known for their ability to metabolize sugar into alcohol
and Carbon dioxide.
 The yeasts cells are dried and marketed as a granular powder or compressed tablets.
 Representative dried yeast contains approximately 45% protein 41, in each gram.

 Ascorbic Acid
 Naturally occuring substance that prevents scurvy and
has useful antioxidant properties.
 Derived biosyntheticaly from D-glucose, D-galactose, or other sugars with the correct chiral
centers at C-4 and C-5 of ascorbic acid.
 Good dietary sources of ascorbic acid includes citrus fruits, tomatoes, strawberries, and other
fresh fruits and vegetables.
 Used to prevent or treat deficiency conditions and to enhance wound healing. 27

 D-biotin; vitamin H
 Physiologically active substance that consists of fused imidazolidone and tetrahydrothiopbene
rings and a valeric acid side chain.
 When biotin deficiency is encountered, it is usually caused by avidin.
 Symptoms of biotin deficiency include alopecia, erythroderma desquamative and seborrheic
dermatitis.
 Generally considered to be well tolerated by humans and free of side effects, even at high
doses.

 Para-aminobenzoic acid 36
 Precursor of folic acid occurs in nature.
 It si not an essential nutrient for humans and should not be considered a vitamin.
 Choline 35
 β-hydroxyethyltrimethylammonium hydroxide
 Component of lecithin, a phospholipid and a precursor of acethylcholine, a neurotransmitter.

 Inositol
 Meso-inositol, myoinositol, or cis-1,2,3,5-trans-4,6-
cyclohexanehexol
 Sweet tasting, optically inactive substance that is sometimes associated with the B vitamin.
 Added to a number of multiple vitamin products.

 Poor absorptions of ingested vitamins occurs frequently in elderly persons, chronically ill
persons, and others who suffer from infections, reduced bile flow, intestinal disease, diarrhea
and the like. 38-40
 Decavitamin capsules and decavitamin tablets – model multivitamin preparations, providing
10 vitamins 37 for which recommended dietary allowances have been established and one
vitamin for which there is no such recommendation.
 Hexavitamin capsules and hexavitamin tablets – contain the following specified amounts of 6
vitamins: vitamin A 1.5mg; B1, 2mg; B2, 3mg; C, 75mg; D, 10 μg; niacinamide, 2mg.

Organic substances, not synthesized within the body, that are essential in small amounts for
the maintenance of normal metabolic functions.
The term vitamins was derived in 1911 when an amine thought to prevent beriberi was isolated
from rice bran; this essential or vital amine was called vitamins.
1. Which of the following vitamins is a precursor of coenzyme A?
a. cobamide b. panthothenate c. thiamine d. riboflavin

2. Which vitamin is formed in the body by exposure to ultraviolet irradiation or

sunlight?
a. vitamin E c. vitamin A b. vitamin D d. vitamin C
3. Free vitamin A does not occur in plants, but in its place are compounds that are converted
into vitamin A in the small animal body. These precursors of vitamin A are called:
a. provitamin B b. neovitamin A c. B-carotene d. b and c

C 4. Which of the following is a precursor of vitamin D? a. prostaglandin c. cholesterol b.

linoleic acid d. aldosterone
C 5. Excess vit. A & D is stored in the body, but excess vit. C & D is readily excreted. What
property shows this? a. vit C & D are water soluble c. both a & b b. vit. A & D are fat soluble d.
none of these
B 6. The vitamin which is used in the prevention of degenerative changes in the central nervous
system. a. vit. A c. vit. C b. vit. B complex d. vit. D
 D 7. Deficiency in this vitamins causes red blood cell fragility a. vitamin A c. vitamin D b.
vitamin K d. vitamin E
D 8. What vitamin deficiency causes pellagra? a. riboflavin c. pantothenic acid b. thiamine d.
nicotinic acid
B 9. This vitamin easily undergoes oxidation a. vitamin A c. vitamin B12 b. vitamin C
d. vitamin B1
A 10. Night blindness is a symptom of a deficiency in this vitamin. a. vitamin A c. vitamin B b.
vitamin C d. vitamin D

A 11. The conversion of beta carotene to vitamin A is carried out in the a. liver c. lungs b. small
intestine d. pancreas

Fat-Soluble Vitamins
• Vitamins A, D, E, and K
Water-Soluble Vitamins
• Vitamin B1,B2, B3,B5,B6, B9, B12, and C 12-19

• Retinol is the major natural form of vitamins.

• A yellow to red oily liquid that may solidify when
refrigerated and should be protected from air and light.
Common dietary source: Animal organs (heart, kidney, liver), eggs, dietary products, and fish.
Defficiency: Nyctalopia, xerophthalmia, hyperkeratosis of skin, growth retardation, and
decreased resistance to infection.
Prescription product: Retin-A, Accutane, and Solatene.

• A term that is used for several related steroids and their metabolites that are essential for
the absorption and utilization of calcium.
Cholecalciferol 20 or vitamin D3 – The primary form of the vitamin encountered in zoologic
species.
Ergocalciferol or vitamin D2- derived form plant steroid. Used to fortify such foods as milk,
bread, and cereals.
• Absorbed readily from small intestine of normal individuals.
• Aids in the utilization of Calcium and Phosphate and is essential to the development and
maintenance of strong teeth and bones.
• Antirachitic vitamin, indicated for prevention and treatment of deficiency states.
• Used to treat familial hypophosphatetemi and hypoparathroidism.
Dietary sources: Butter cream, and liver
Deficiency: Children-Rickets 21 & Adults-Osteomalacia
Prescription products: Delta-D, Deltalin, Calciferol, Drisdol, Calderol, Rocaltrol, DHT, and
Hytakerol.

•
•
•
•
A term that refers to various forms of alpha-tocopherol. 22
Requires bile salts and dietary lipids for efficient absorptions from the
intestinal tract.
Used primarily forprophylactic purpose to prevent deficiency states in conditions in which
reduced absorption is likely.
Stored in adipose tissue of the body.
Dietary sources: Plant oils, green vegetables, whole grains, egg yolks, and meats.
Deficiency: muscular dystrophy, coronary disease, and sterility.
Beneficial effect: Cancer, fibrocystic disease of breast, sickle-cell, and lung
toxicity.
Prescription products: Aquasol E, CEN-E, E-Ferol, E-Vitaal,Epsinal-M, Pheryl-E and Viterra E.

• A term that refers to 2-methyl-1, 4-naphthoquinone 23 and derivatives of this compound

that exhibit an antihemorrhagic activity. 24
• Vitamin K1 ocurs in green leafy vegetables
• Vitamin K2 has a larger aliphatic side chain than Vit. K1.
• Vit. K3 is a synthetic material with Vit K activity
• The lymphatic system is the major means of transporting vit. K to the liver where it tends to
concentrate.
Dietary products: fruits and vegetables Deficiency: Hemmorhagic disease
Prescription product: Konakion, and Mephyton

• Known as Thiamine
• Final steps in both the biosynthesis and chemical synthesis of this vitamin
involve linkage of the two ring system.
• Stable in acidic environment
• Required for carbohydrates metabolism and for neurologic functions.
• Used to supplement an adequate diet.
• Used as the hydrochloride and monoitratesalts and is available in tablet, elixir, and injection.
Dietary sources: whole grains, legumes, and meats.
Deficiency: hypersensitivity, loss of appetite, fatigue, and muscular
weakness)
Prescription products: Betalin S and Biamine

• Known as Riboflavin 25
• A yellow, heat-stable substance that is
slightly soluble in water.
• Treatment for acne, migraine headaches and muscle cramps.
Dietary products: eggs, legumes and meats.
Deficiency: rarely encountered in healthy persons receiving a balanced diet.
Prescription products: Rionin-50

• Known as Niacin, Nicotinic acid

• A simple, naturally occurring pyridine derivative that prevent
pellagra.
• Used for dietary and therapeutic purpose.
• Causes direct peripheral vasodilatation of warmth, especially in the area of face, neck and
ears.
• Used to prevent or treat deficiency conditions. Dietary sources: lean meats, fish and dairy
products
Deficiency: inadequate nutrition, intestinal malabsorption, genetic errors of metabolism.
Prescription products: Niac, Nico-400, Nicobid, Nicolar, Nico- span, Nicotinex, and tega span.

• Also known as Pantothenic acid 26

• A components of vit. N complex that is sometimes known as the “chick antidermatitis factor”
• A viscous, oily liquid, used as the calcium salt.
Dietary sources: Deficiency: Prescription products:

• A term that is applied to pyridoxol, pyridoxal, and pyridoxamine. Term used for pyridoxol in
pharmacy and medicine. Occur in plant materials.
• Used for exogenous dietary supplementation and therapeutic purpose.
• Readily absorbed in the jenunum, but the vitamin synthesized by the microflora
of the colon is largely excreted in feces.
• Available as the hydrochloride salt in tablet, sustained released, and injection.
Dietary sources: Meats, bananas, whole cereal grains, nuts, and potatoes.
Deficiency: neurologic abnormalities, skin lesions, and hhypochromic microcytic anemia.
Prescription products: Beesix, Hexa Betalin, Nestrex, and Vitabee-6

• Known as folic acid, folacin, and pteroylglutamic acid 44-45 are terms that refer to a
material with antiamenia properties.
• Naturally occurring biochemical metabolite of folic acid that finds special use in an anticancer
drug regimen employing folate antagonist.
• Available as tablet and injection dosage forms.
Dietary sources: Leafy vegetables and liver Deficiency: Megaloblastic anemia
Prescription products: folvite and wellcovorin

 Vitamin B12 and cobalamins 42 are terms that refer to a series of porphyrin-related
corrinoid derivatives that function as extrinsic factors to prevent pernicious anemia.
 Cyanocobalamin – a red crystalline material, is the most stable of the cobalamins; most
frequently utilized in theraphy.
 Hydroxocobalamin – finds some therapeutic use; in the cyano group is replaced with a
hydroxyl substituent.
 Stored in the liver and liver extract has been the classic source of the vitamin.
 Absorbed in the lower half of the ileum.
 Essentials to cell reproduction, growth hematopoiesis, and synthesis of myelin and
nuceoprotein.
  Unicellular organisms that are well-known for their ability to metabolize sugar into alcohol
and Carbon dioxide.
 The yeasts cells are dried and marketed as a granular powder or compressed tablets.
 Representative dried yeast contains approximately 45% protein 41, in each gram.

 Ascorbic Acid
 Naturally occuring substance that prevents scurvy and
has useful antioxidant properties.
 Derived biosyntheticaly from D-glucose, D-galactose, or other sugars with the correct chiral
centers at C-4 and C-5 of ascorbic acid.
 Good dietary sources of ascorbic acid includes citrus fruits, tomatoes, strawberries, and other
fresh fruits and vegetables.
 Used to prevent or treat deficiency conditions and to enhance wound healing. 27

 D-biotin; vitamin H
 Physiologically active substance that consists of fused imidazolidone and tetrahydrothiopbene
rings and a valeric acid side chain.
 When biotin deficiency is encountered, it is usually caused by avidin.
 Symptoms of biotin deficiency include alopecia, erythroderma desquamative and seborrheic
dermatitis.
 Generally considered to be well tolerated by humans and free of side effects, even at high
doses.

 Para-aminobenzoic acid 36
 Precursor of folic acid occurs in nature.
 It si not an essential nutrient for humans and should not be considered a vitamin.
 Choline 35
 β-hydroxyethyltrimethylammonium hydroxide
 Component of lecithin, a phospholipid and a precursor of acethylcholine, a neurotransmitter.

 Inositol
 Meso-inositol, myoinositol, or cis-1,2,3,5-trans-4,6-
cyclohexanehexol
 Sweet tasting, optically inactive substance that is sometimes associated with the B vitamin.
 Added to a number of multiple vitamin products.

 Poor absorptions of ingested vitamins occurs frequently in elderly persons, chronically ill
persons, and others who suffer from infections, reduced bile flow, intestinal disease, diarrhea
and the like. 38-40
 Decavitamin capsules and decavitamin tablets – model multivitamin preparations, providing
10 vitamins 37 for which recommended dietary allowances have been established and one
vitamin for which there is no such recommendation.
 Hexavitamin capsules and hexavitamin tablets – contain the following specified amounts of 6
vitamins: vitamin A 1.5mg; B1, 2mg; B2, 3mg; C, 75mg; D, 10 μg; niacinamide, 2mg.