M1: Introduction  Simultaneous application of various scientific

Introduction disciplines with the object of acquiring

Pharmacognosy is derived from two Latin words knowledge of drug from every point of view.
pharmakon, ‘a drug,’ and gignoso, ‘to acquire
knowledge of ’. It is defined as the science of Lesson 2: Scope and Practice of Pharmacognosy
pharmaceuticals that are derived from nature. It
deals with all medicinal plants, including those PLANT CHEMISTRY: is the art of resolving plants into
yielding complex mixtures, which are used in the form its chemical constituents or isolating the most
of crude herbs or extracts (phytotherapy), pure important components in the form of pure chemical
compounds such as morphine, and foods having compounds.
additional health benefits only in the context of having PHYTOCHEMISTRY: Study of the composition of
preventive effects (nutraceuticals) (Heinrich, M. et al, plant principle, their extraction, biosynthesis, and
2018). identification.
The history of pharmacy was for centuries PHYTOCHEMICALS: is a more recent evolution of
identical to the history of pharmacognosy, or the study the term that emphasizes the plant source of most
of materia medica, which were obtained from natural non-nutrient plant chemicals which are considered
sources – mostly plants, but also minerals, animals, protective, disease-preventing compounds.
and fungi. This introductory module will provide an PHYTOTHERAPY: use of plant extract for medicinal
overview of some historical aspects of medicinal purposes
plants used by different societies (ethnobotany, HERBS: leaves, roots, and flowers of plants grown
ethnopharmacology) and on the role of plants in a and processed for culinary, cosmetic, industrial,
variety of popular ‘nonscientific’ medical systems medicinal, landscaping, decorative and fragrant
(traditional medicine) and also provide scientific basis purposes; a plant that does not form the woody stem
for the use of plants in pharmacy. CRUDE DRUGS: Vegetable or animal drugs that
consist of natural substances that have undergone
only the process of collection and drying.
M1 Part 1: Introduction to Pharmacognosy and Plant MARC: Undissolved portion of the drug that remains
Chemistry after the extraction process is completed.
EXTRACTION: is the separation of medicinally active
Lesson 1: Origins of Pharmacognosy and Plant portions of plant or animal tissues using selected
Chemistry solvents through standard procedures
PHARMACOGNOSY: a study of natural drugs, EXTRACTIVES: product of extraction, single
including such factors as their botanical sources, substance or mixture of substances which are c
constituents, and biological, biochemical, and ETHNOBOTANY: coined by John William
economic characteristics; it is the science of biogenic Harshberger, 1895; it is a broad term referring to the
or nature-derived pharmaceuticals and poisons. study and relationship of plants by humans and their
1. Ancient Mesopotamia: Cuneiform writing culture. Richard Evans Schulte, father of modern
(baked clay tablets) ethnobotany
2. Ancient Egypt: Ebers Papyrus (700 drugs), ETHNOPHARMACOLOGY: the scientific study of
1550 B.C. the oldest, most complete, and material used by ethnic groups as medicines, aka
most important medical papyri of ancient TRADITIONAL MEDICINE: It is the sum total of all
Egypt non-mainstream medical practices.
3. Ayurveda: Ayur means life and Veda means ETHNOMEDICINE: it refers to the use of plants by
the study of humans as medicines
4. Ancient Greece and Rome ELUCIDATION: It is the determination of the chemical
 Pedanios Dioscorides: De Materia Medica is structure of a chemically uncharacterized substance.
an organized pharmaceutical and medical considered as their chief constituents of the drug
knowledge giving information pertaining to
drugs and their usage. Lesson 3: Plant Nomenclature and Taxonomy
 Claudius Galen: Greek Physician- Plant Nomenclature or Botanical Nomenclature is the
Pharmacist, described the method of formal, scientific naming of plants, although related, it
preparation of formula containing plant and is distinct from Taxonomy. Botanical nomenclature
animal drugs – GALENICALS has a long history, going back beyond the period
 Avicenna: Persian Galen when Latin was the universal language (lingua franca)
5. The 18th Century Pharmacognosy throughout Europe and the system of naming plants
 Johann Adam Schmidt(1759-1809), were based on their physical description or
Lehrbuch der Materia Medica characteristics. It can be dated back during the time of
 Carolus Linnaeus (naming and classifying Theophrastus, Pedanios Dioscorides and other
plants) Roman and Greek writers. The starting point of
 1803: Era of pure compounds (Narcotine) modern botanical nomenclature appears consistently
6. Pharmacognosy: regarding as “mother of all on the work of Carolous Linnaeus, Species Plantarum
science” in 1753. Botanical nomenclature is managed by the
 from two Greek words pharmakon (drug) and International Code of Nomenclature for algae, fungi
gnosis (knowledge) – C.A. Seydler and plants.
 pharmakon (drug) and gignosco - Evans
Classification of Vegetable drugs:
 applied science that deals with the biologic,
 Alphabetical
biochemical, and economic features of
natural drugs and their constituents – Tyler  Taxonomic
 Morphological
  Pharmacological or Therapeutic The medicinal effects of plants are due to metabolites
 Chemical or Biogenetic especially secondary compounds produced by plant
species.
M1 Part 2: Introduction to Pharmacognosy and Plant They include:
Chemistry  Primary Metabolites; and
Lesson 4: Plant Growth Regulators:  Secondary Metabolites
PLANT GROWTH REGULATORS:
Primary Metabolites Secondary
 Auxins Metabolites
 Gibberellins 1. Organic 1. Organic
 Cytokinins
compounds produced compounds produced
 Abscisic acid
in the plant kingdom in the plant kingdom
 Ethylene
These plant hormones are specific in their action:
2. Have metabolic 2. Don’t have
 Active in very low concentrations
 Regulate cell enlargement functions essential apparent functions
 Regulate cell division for plant growth and involved in plant
 Cell differentiation development growth and
 Organogenesis development.
 Senescence
 Dormancy
3. Produced in every 3. Produced in
Plant Chemistry plant. different or specific
groups of plant
This is the study of chemicals produced by the many families or in specific
diverse organisms of nature, including plants, tissues, cells, or
microbes (fungi and bacteria), marine organisms, and
developmental stages
more exotic sources such as frog skins and insects.
throughout plant
Why study medicinal plants? development.

 Many of the modern medicines are produced

indirectly from medicinal plants. Ex: aspirin 4. Examples are 4. Include terpenoids,
carbohydrates, amino alkaloids (non-protein
acids, nucleotides, amino acids, amines,
fatty acids, steroids, cyanogenic
and lipids. glycosides, and
glucosinolates), and
phenolics

Primary Metabolic Pathways

 Plants are directly used as medicines by a
majority of cultures around the world. Ex:  The building blocks for secondary
TCM, Ayurveda metabolites are derived from primary
metabolism.
 Many food crops have medicinal effects. Ex:
Garlic  The most important building blocks
employed in the biosynthesis of secondary
 Medicinal plants are sources of new drugs;
metabolites are derived from the
250, 000 flowering plants.
intermediates acetyl coenzyme A (acetyl-
 Studying medicinal plants helps to
CoA), shikimic acid, mevalonic acid, and 1-
understand plant toxicity and protect humans
deoxyxylulose 5-phosphate
and animals from natural poisons.
 Cultivation and preservation of medicinal
plants protect biological diversity.
Plant Constituents
 Plants remain the most important source of
natural drugs, however, only about 10%
have been fully studied.
 More than 30% of prescription drugs are
natural products (e.g colchicine).
 More than 60% of anticancer and anti-
infective drugs are natural products (e.g.
Taxol, Penicillin).
 Plant constituents comprise a wide variety of
organic substances that are formed and
accumulated by plants. M1 Part 3: Introduction to Pharmacognosy and Plant
Chemistry
 What are the common features of these organic
Lesson 1 Part 3: Ethnobotany compounds?
Shortly before the start of the 20th century (1896), the 1. All organic compounds contain carbon atoms
American botanist William Harshberger coined the and most contain hydrogen atoms. Carbon
term ‘ethnobotany’ – the study of plant use by always forms four covalent bonds, and
humans. hydrogen forms one covalent bond.
2. Carbon forms single, double, and triple
Ethnobotany studies the relationship between bonds to other carbon atoms.
humans and plants in all its complexity and is 3. Some compounds have chains of atoms and
generally based on detailed observation and study of some compounds have rings.
the use a society makes of plants, including all the 4. Organic compounds may also contain
beliefs and cultural practices associated with this use. elements other than carbon and hydrogen.
Any atom that is not carbon or hydrogen is
It is usual for ethnobotanists to live with indigenous called a heteroatom.
people, to share the everyday life of their community, FUNCTIONAL GROUPS
and, of course, to respect the underlying cultures. In addition to strong C- C and C -H bonds, organic
Ethnobotanists have a responsibility both to the molecules may have other structural. There are
scientific community and to the indigenous cultures. features as well. →structural features, called
functional groups
M2: Hydrocarbon and its Derivatives
Introduction
Hydrocarbons are compounds that contain only
the elements of carbon and hydrogen. All Ethanol (CH3CH2OH), for example, has two carbons
hydrocarbons other than alkanes contain multiple and five hydrogens in its carbon backbone, as well as
bonds. Alkanes, which have no functional groups and an OH group, a functional group called a hydroxyl
therefore no reactive sites. And hydrocarbons by the group. The hydroxyl group determines the physical
addition of functional groups and by interaction, all properties of ethanol as well as the type of reactions it
other natural compounds can theoretically be derived. undergoes. Moreover, any organic molecule
Among the most common functional groups are containing a hydroxyl group has properties similar to
carboxylic acids, alcohols, ketones, aldehydes and ethanol. Compounds that contain a hydroxyl group
phenols; biochemical interactions produce esters, are called alcohols.
lactones etc (Trease and Evans, 2010).

M2 Lesson 1: Introduction to Hydrocarbons and Its

Derivatives
Lesson 1: Introduction to Hydrocarbon and Its
Derivatives HYDROCARBONS
Hydrocarbons are compounds that contain only the
Hydrocarbons and derivatives elements of carbon and hydrogen, as shown in the
table below:
Monobasic Acids
 C1–C6 Monocarboxylic acids
 Fatty acids
 Aromatic acids
Dibasic and Tribasic Acids
Alcohols
 Monohydric aliphatic alcohols, Monohydric
terpene alcohols, Monohydric aromatic
alcohols, Dihydric alcohols, Trihydric
alcohols, Polyhydric aliphatic alcohols COMPOUNDS CONTAINING A SINGLE BOND TO A
Fats and Oils HETEROATOM
Waxes Several types of functional groups contain a carbon
Prostaglandins atom singly bonded to a heteroatom. Common
Notice the elements that make up the molecules of examples include alkyl halides, alcohols, ethers, and
capsaicin and caffeine. What are the common amines
features of these organic compounds?
Capsaicin, the
compound
responsible for
the characteristic
spiciness of hot
peppers, is the
active ingredient
in several topical
creams for pain
relief.

Caffeine is the bitter-tasting stimulant found in coffee,

tea, cola beverages, and chocolate.
M2 Lesson 2: Acids, Alcohols and Esters acid), Caffeic acid: (hydroxycinnamic acid),
Lesson 2: Drugs Containing Monocarboxylic, Dibasic Quinic acid: acid with an alcohol group
and Tribasic Acids, Alcohols and Esters (tetrahydroxyhexabenzoic acid), Mandelic
acid, Shikimic acid served as _____ sources
Hydrocarbons and derivatives star anise, needles of Pinaceae and gum
Monobasic Acids tree, Chlorogenic acid
 C1–C6 Monocarboxylic acids  Dibasic acids: Oxalic acid, Malonic acid,
 Fatty acids Succinic acid, Fumaric acid, Malic acid,
 Aromatic acids Tartaric acid (Tamarind)
Dibasic and Tribasic Acids  Tribasic acids: Citric acid (Citrus fruits),
Alcohols Isocitric acid, Aconitic acid (Aconitum spp.)
 Monohydric aliphatic alcohols, Monohydric
terpene alcohols, Monohydric aromatic
alcohols, Dihydric alcohols, Trihydric monobasic acid (aromatic acid):
alcohols, Polyhydric aliphatic alcohols chlorogenic acid (from coffee)
ORGANIC ACIDS
Carbon 1 to Carbon 6
Formic acid: from Red ant, Formica rufa and Stinging
nettle, Urtica dioica

Acetic acid, propionic acid, iso-butyric acid from

Ceratonia siliqua,
valeric/iso-valeric acid, crotonic and tiglic acid from
Croton tiglium, Angelic acid, and senecioic acid.
dibasic acid: malic acid (from
apple)

Acetic acid

tribasic acid: citric acid (citrus

fruits)

Formic acid

ALCOHOLS
Monohydric terpene alcohols (from MVA pathway)

 Non-cyclic: geraniol (otto of rose), nerol

(orange and bergamot ) and linalol (as linalyl
acetate in lavender and rosemary)
 Monocyclic: terpineol (neroli oil) and
menthol(peppermint oil)

Dicyclic: Sabinol (Juniperus sabina), borneol

Fatty acids: can be saturated (CnH2nO2) or
unsaturated (CnH2n - (2x) O2), important components Dihydric alcohols (glycols): 3,6-dihydroxytropane,
of plant oils, resins, and waxes; aliphatic Panaxadiol – component of ginseng steroid,
monocarboxylic acid. Obtained from hydrolysis of fats Polyenediol – oenanthotoxin – toxic component of
hemlock
 Cyclic fatty acid: hydnocarpic acid,
chaulmoogric acid, gorlic acid, Prostanoic Trihydric alcohol: glycerol
acid
 *Aromatic acids: Benzoic acid, Cinnamic Polyhydric alipathic alcohols: Meso-erythritol: found in
acid: Truxillic acid occurs in coca leaves, seaweeds and lichens; hexahydric sugar alchols like
Salicylic acid (o-hydroxybenzoic acid), sorbitol (rosaceous fruits), mannitol (manna), dulcitol
Protocatechuic acid (3,4-dihydroxybenzoic (Euonymus)
acid), Veratric acid (3,4-dimethoxybenzoic  Ethanol: 92.3% by weight of ethanol, 94.9%
acid), Gallic acid (3,4,5-trihyroxybenzoic by volume; 70 % which is used as local anti-
acid), P-coumaric acid: (p-hydroxycinnamic infective
acid), Ferulic acid: (hydroxymethoxycinnamic
  Diluted Alcohol: 4 % to 49.5% used as
solvent
 Brandy: distillation from wine
 Whisky: fermented malted grain
 Rum: fermented molasses
 Mannitol: from Fraxinus ornus (commercial
source), Lecanora esculenta used as
osmotic diuretic and laxative
 Sorbitol: from Sorbus aucuparia. Half as
sweet as sucrose, used as humectant

dihydric alcohol: oenanthotoxin

(poisonous constituent of
hemlock water dropsnow)

Although most vegetable oils are liquid at ordinary

temperatures and most animal fats are solid, there are
notable exceptions, such as cocoa butter, which is a‘
solid vegetable oil, and cod liver oil, which is a liquid
animal fat
LIPIDS: Collective term for fixed oil, fats and waxes,
are heterogeneous group of compounds (fats, oils,
steroids, waxes and related compounds), that are
related more by their physical than by their chemical
properties.
dicyclic terpene alcohol:
sabinol (from Juniperus Common properties:
sabina) (1) Relatively insoluble in water
(2) Soluble in non-polar solvents

Properties of Lipids:
(1) Greasy to touch, leaves a permanent oily stain on
paper
(2) Lighter than water
(3) Soluble in an organic solvent, insoluble in water
(4) When pure, colorless with bland odor and taste;
(5) Yellow color in fat is due to carotene (provitamin
A)
(6) When heated strongly, undergoes decomposition
forming acrid flammable vapors and when ignited,
they burn with a sooty flame.
monocyclic terpene alcohol:
geraniol (from otto of rose) Classification of Lipids:
and nerol (from oil of • Simple lipid – ester of fatty acid and alcohol
orange) • Fats/fixed oil – ester of fatty acid and glycerol
• Triglycerides – esters of three molecules of fatty
acids plus one molecule of glycerol, found in adipose
tissue, butterfat, lard, suet, fish oils, olive oil, corn oil
• Waxes – ester of fatty acid and HMW monohydric
alcohol, beeswax, head oil of sperm whale, cerumen,
carnauba oil, and lanolin
• Compound Lipid: Esters of fatty acid, alcohol and
another compound.
M2 Lesson 3: Lipids and Its Properties A. PHOSPHOLIPIDS: Fatty acid and alcohol plus a
Lesson 3: Lipids and Its Properties phosphoric acid residue, frequently have nitrogen-
Lipids are esters of long-chain fatty acids and containing bases and other substituent,
alcohols, or of closely related derivatives. glycerophospholipids, sphingophospholipids
Includes: fixed oils and fats; waxes
B. GLYCOLIPIDS: Glycosphingolipids, fatty acid and
Waxes - the alcohol has a higher molecular weight, sphingosine plus carbohydrate.
e.g., cetyl alcohol
C. OTHER COMPLEX LIPIDS: sulfolipids and
Fixed oils and fats - glycerol combines with fatty aminolipids, lipoproteins
acids. Derived Lipid – product of simple and compound lipid
Fats and Oils are triacylglycerols. upon hydrolysis.
Remember the following:  Second Grade: crushed pulp with more
 Hydroxyl Acid: Ricinoleic acid pressure
C17H32(OH)COOH Source: Castor  Technical Grade: pulp mixed with hot water
Cerebronic acid C23H46(OH)COOH Source: that is pressed again
Phrenosin  Sulfur Grade: pulp is extracted with carbon
 Dihydroxystearic acid C17H33(OH)COOH disulphide
Source: Castor  Tournant Grade: obtained when fallen,
Cyclic Acid: Hynocarpic C15H27COOH decomposed or refuse olives are allowed to
 Chaulmoogric C17H31COOH ferment
 Soap – metallic salts of fatty acid: Fatty acid
+ KOH--> K soap-->Soft soap  Peanut Oil aka Arachis Oil SN: Arachis
Fatty acid + NaOH--> Na soap--> Hard soap hypogaea FN: Fabaceae Use: solvent for IM
 Tristearin (Fat): Glycerol + 3 stearic: injection
Oleopalmitostearin  Rapeseed Oil SN: Brassica campestris
Glycerol + oleic acid/ palmitic acid/ stearic  Canola oil: bland taste no clouding upon
acid refrigeration, used as salad oil/dressing
Triacylglycerol: it can be, simple triacylglycerol or
mixed triacylglycerol SOURCES of POLYUNSATURATED FIXED OILS
 Soybean oil SN: Glycine soja FN: Fabaceae
M2 Lesson 4: Fixed Oils, Fats, and Waxes and their Source: lecithin, stigmasterol
Properties  Cottonseed oil SN: Gossypium hirsutum FN:
Lesson 4: Pharmaceutical Fixed Oils, Fats, and Malvaceae Use: solvent for injection
Waxes and their Properties  Sesame Oil aka Teel Oil or Benne Oil SN:
Sesamum indicum FN: Pedaliaceae
Classification of Fats and Fixed Oils o Constituent: Sesamolin – synergist
• Non – Drying oils (< 100): constituent compose more for pyrethrum insecticide
oleic acid, examples are coconut oil, peanut oil, olive
 Almond Oil aka Expressed Almond Oil or
oil
Sweet Almond Oil FN: Rosaceae
• Semi Drying oils (100 – 120): constituent compose
o SN: Prunus amygdalus Persic Oil
more oleic acid and linoleic, examples are Corn,
aka Apricot Kernel Oil or Peach
cottonseed, wheat, sesame, brazil, soybean
Kernel Oil; Apricot – Prunus
• Drying Oils (> 120): constituent compose more
armeniaca Linne Peach – Prunus
linoleic and linolenic, examples are linseed,
persica Siebold et Zuccarini
sunflower., poppyseed
 Corn Oil SN: Zea mays FN: Poaceae
TEST FATS AND FIXED OILS o Use/s: Solvent for injection; solvent
Physical Test: Specific Gravity, Refractive index, for erradiated ergosterol ; salad oil ;
Viscosity, Melting/Solidification point ingredient of high dietary
Chemical Tests (Quantitative Tests): supplement ; ingredient for enteral
 Acid Number – the amount of free fatty acid nutrition therapy ; margarine
 Saponification Number – indicates  Safflower Oil SN: Carthamus tinctorius FN:
saponification of the ester, ester number, Asteraceae
 Iodine Number – degree of unsaturation ,  Sunflower Oil SN: Helianthus annus FN:
Volatile acidity, Unsafonifiable matter, Acetyl Asteraceae
value, Hydroxyl value, Peroxide value and  Linseed Oil aka Flaxseed Oil SN: Linum
anisidine value, Rancidity usitatisimum FN: Linaceae
Hydrolysis of Fats and Fixed oil: Fats/Fixed Oil   Cod Liver Oil SN: Gadus morrhua FN:
glycerol + Fatty Acid Gadidae Source of vitamin A and D
SOURCES of SATURATED FIXED OILS o Use: Antirachitic
 Coconut Oil SN: Cocos nucifera FN:  Germ Oils (Wheat grain) SN: Triticum
Arecacea aestivum L. Constituents: Linoleic acid (52 –
 Palm Oil and Palm Kernel Oil SN: Elaeis 59%), Palmitic acid (14 – 19%), Oleic acid
guineensis FN: Arecaceae (12 – 23%), Linolenic acid (3 – 10
%)Hydnocarpus wightiana
SOURCES of MONOUNSATURATED FIXED OILS  Evening Primrose Oil SN: Oenothera spp.
 Castor Oil SN: Ricinus communis FN: (O. biennis, O. lamarkiana) Family:
Euphorbiaceae Use: Cathartic Onagraceae Constituents: Gamma linolenic
o Composed of: Triricinolein – 75%, acid (GLA) Use/s: Dietary supplement,
Ricinoleic acid component of cosmetics, Tx of atopic
 Olive oil aka Sweet oil SN: Olea europea FN: eczema, Tx of pre-menstrual syndrome
Oleaceae  Borage Oil or Star flower SN: Borago
o Use/s: Pharmaceutical aid, Dental officinalis FN: Boraginaceae
retardant, Demulcent, Laxative, o Constituent/s: Linoleic acid, GLA,
Emollient Oleic acid, Palmitic acid Use/s:
Same as evening primerose
OLIVE OIL GRADES OF PURITY  Saw Palmetto Fruit SN: Serenoa repens FN:
 First Grade: crushed pulp with less pressure Arecaceae Constituent/s: Oleic acid, Lauric
acid, Myristic acid, Palmitic acid
  Hydnocarpus oil SN: FN: Flacourtiaceae trimester pregnancy. SIDE EFFECTS: Vomiting;
Constituent/s: Hydnocarpic acid – (48%), pyrexia; diarrhea; nausea; HA; chills.
Chaumoolgric acid – (27%), Gorlic acid  ADVERSE EFFECT: Lack of
o Use/s: Treatment for leprosy vasoconstriction that result to HTN.
ALPROSTADIL (PGE1) ACTION: Produces
FATS AND RELATED COMPOUNDS vasodilation; inhibits platelet aggregation and
stimulates intestinal and uterine smooth muscle.
 Theobroma Oil or Cacao Butter SN:  USE: Palliative therapy to maintain
Theobroma cacao FN: Sterculiaceae temporarily neonates with patent ductus
o Use: suppository base arteriosus and congenital heart defects that
Constituents/s: 37% oleic acid, 34% restrict the pulmonary or systemic blood flow.
stearic acid, 26% palmitic acid, 2% MISOPROSTOL ACTION: Inhibits gastric acid
linoleic acid secretion; also produces uterine contractions that may
 Lanolin aka Hydrous Wool Fat (25%-30% endanger pregnancy by causing abortion. USE: Used
water) from Ovis aries (Bovidae) aka orally in patients that are at high risk for developing
Anhydrous Lanolin aka Wool Fat contains ulcers during NSAID activity.
NMT 0.25% water used as emollient
M3: Carbohydrates
WAXES: Esters resulting from the high-molecular Introduction
weight, straight chain alcohol. This module covers carbohydrates which consist of
 Spermaceti SN: Physeter macrocephalus carbon, hydrogen, and oxygen having the last two
FN: Physeteridae elements present in the same proportions as in water.
o Use: Quality emollient and Carbohydrates are among the first products to arise
ingredient in cold creams and other as a result of photosynthesis. They constitute a large
cosmetics proportion of the plant biomass and are responsible
o Substitute: Synthetic spermaceti or (i.e. cellulose) for the rigid cellular framework and for
providing an important food reserve (e.g. starch). One
cetyl esters wax.
special pharmacognostic importance is the fact that
 Jojoba Oil SN: Simmondsia chinensis FN:
sugars unite with a wide variety of other compounds
Buxaceae
to form glycosides. Mucilages, as found in
 Beeswax SN: Apis mellifera FN: Apidae marshmallow root and psyllium seeds, act as water-
Principal constituents: myricyl palmitate, retaining vehicles, whereas gums, which are similar in
myricyl cerotate, myricyl hypogaeate and composition and properties, are formed in the plant by
ceryl 2-hydroxypalmitate injury or stress and usually appear as solidified
 Yellow wax use as stiffening agent; exudates; both are typically composed of uronic acid
ingredient in yellow ointment; base for and sugar units. The cell walls of the brown seaweeds
cerates and plasters; cosmetics and polishes and the middle lamellae
 White wax: Bleached yellow wax; purified
wax; used in compounding ointments and M3 Lesson 1: Introduction to Carbohydrates
cold creams. Lesson 1: Introduction to Carbohydrates
 Carnauba wax SN: Copernicia prurifera FN: Carbohydrates and related compounds
Arecacea Sugars (saccharides)
 Monosaccharides
PROSTANOIDS: part of a family of biologically active  Di-, tri- and tetrasaccharides
lipids derived from the twenty-carbon essential fatty  Polysaccharides
acids or eicosanoids, relates to the products of the o Sugars and Sugar-Containing
cyclooxygenase pathway, prostanoic acid as the
Drugs
central structural element
o Polysaccharides and
Three main groups: Polysaccharide-Containing Drugs
• Prostaglandins (PGs) o Cellulose (Fibers)
• Prostacyclins (PGIs) o Gums and Mucilages
• Thromboxanes (TXs)
CARBOHYDRATES: are aldehydes or ketone
PROSTAglandins: acts as local hormones, derivatives of polyhydric alcohols consisting of
synthesized from eicosanoic polyunsaturated fatty carbon, hydrogen, oxygen “hydrate of carbon”.
acids (arachidonic acid) to form cyclopentane ring  the first products formed in photosynthesis.
PG1, PG2, and PG3– numbers are based on the  the products from which, by subsequent
double bonds in the side chain organic reactions, the plant synthesizes a
The letter component identifies the functional groups greater number of other constituents.
of the cyclopentane ring  constitute a large proportion of the plant
CARBOPROST (PGF2α) ACTION: Stimulates biomass and are responsible, as cellulose,
contraction of the gravid uterus similar to the for the rigid cellular framework and, as
contractions of the full term uterus at labor USE: Used starch, for providing an important food
in terminating second trimester pregnancy. reserve.
 SIDE EFFECTS: Vomiting and/or diarrhea,
elevation of BP.  IMPORTANCE
DINOPROSTONE (PGE2) ACTION: Uterine stimulant
approved for termination of 12th week to the 2nd
  Provide a significant fraction of the energy in Cellulose- a polysaccharide composed of glucose
the diet of most organisms, transport energy units joined by -1,4 linkages, forms the primary cell
and the building block of the cell wall; walls in plants.
 Cell membrane components that mediate
some forms of intercellular communication; Hemicelluloses – occur with cellulose; more soluble
 Serves as a structural component of many and more easily hydrolyzed than cellulose.
organisms
o Cell walls of bacteria Gums and mucilages - Closely related to the
o Exoskeleton of many insects hemicelluloses which constitute an important group of
o Fibrous cellulose of plants drugs both from the pharmaceutic and the therapeutic
viewpoint
 Plant metabolites contain sugar as an
essential feature of their structure;
Pentoses – applied to a group of sugars that has the
 Play an ecological role in plant-animal
general formula C5H10O5, ( Examples arabinose,
interaction, protection from wound and xylose, ribose).
infection and detoxification of foreign
substances; and
 Sugar and starch are used as food and
pharmaceutical

Classification of Carbohydrates
 Monosaccharide: cannot be hydrolyzed to
simple sugar
 Disaccharide: hydrolyzed into 2 Pentoses - are products resulting from the hydrolysis
monosaccharide of the pentosans.
 Trisaccharide: yields 3 monosaccharide
Xylan, which occurs in the wood of deciduous trees, is
 Tetrasaccharide: Yields 4 monosaccharide
also an example of a pentosan.
 Polysaccharide: Contains more than 10
monosaccharide units
Pentoses also result from the hydrolysis of gums and
 Monosaccharides mucilages.
Sugars are crystalline, soluble in water, and sweet M3 Lesson 2: Monosaccharides, Di-, Tri- and
tasting. Such as: Tetrasaccharides
 Monosaccharides – compounds that cannot Lesson 2: Monosaccharides, Di-, Tri- and
be hydrolyzed to simpler sugars. Tetrasaccharides
 Disaccharides - yield 2 monosaccharide Carbohydrates and related compounds
molecules on hydrolysis Sugars (saccharides)
 Trisaccharides – yield 3. And so on…  Monosaccharides
 Monosaccharides – tioses (has 3 carbons),  Di-, tri- and tetrasaccharides
tetroses (4 carbons), pentoses (5 carbons)  Polysaccharides
and so on… Sugars and Sugar-Containing Drugs
Polysaccharides and Polysaccharide-Containing
Drugs
Cellulose (Fibers)
Gums and Mucilages

MONOSACCHARIDES
Xylose: Wood sugar, the main building block of
hemicellulose; Source: corn cobs; Use: Diagnostic
agent to evaluate intestinal absorption.

Polysaccharides are complex, high-molecular-weight

carbohydrates are represented by:
 starch
 inulin
 celluloses
Hexosan – a polysaccharide that is hydrolyzed to
hexose.
Glucosans – a starch that is hydrolyzed to glucose.
DISACCHARIDES: meaning "two sugars“, are
Fructusans – inulin that is hydrolyzed to fructose.
commonly found in nature as sucrose, lactose, and
Cellulose - a polysaccharide composed of glucose
maltose
units joined by -1,4 linkages, forms the primary cell
Formed by a condensation reaction where one
walls in plants.
molecule of water condenses or is released during the
joining of two monosaccharides, the type of bond that
The plant also builds its structural skeleton from
is formed between the two sugars is called a
carbohydrate material.
glycosidic bond.
  Maltose – malt sugar, it is a fructosan, joined  Dextrans: Leuconostoc mesenteroides, Used
by an alpha glycosidic bond. in 6% solution as a plasma expander in
cases of trauma, burns to reduce blood
Use in alcohol production, Disaccharides viscosity.
 Sucrose – Table Sugar, An excellent  Cellulose: most abundant organic compound
preservative because it has no "reducing on earth, a principal structural element of
end" or reactive group like the other sugars, higher plant cell wall linear β- 1,4 glycosidic
hydrolysis of sucrose yields mixtures of bonds
glucose and fructose called “invert sugars”  Purified Cotton/Absorbent Cotton:
 Lactose – Milk Sugar, joined by beta Gossypium hirsutum (Malvaceae) used as a
glycosidic bond, many people are lactose surgical dressing, absorbs blood, pus, mucus
intolerant and suffer from intestinal cramping & keeps bacteria from infecting a wound.
and bloating due to the incomplete digestion  Powdered Cellulose: the purity of cellulose is
of the substance. defined by measuring its solubility in NaOH
solution, cellulose that remains insoluble is
called α-cellulose. Used as a pharmaceutical
exicipient

Cellulose Derivative
OLIGOSACCHARIDES  Methylcellulose – artificial tears or contact
 Important oligosaccharides are raffinose and lens solution
stachyose (found in beans and legumes)  Ethylcellulose – tablet binder and film coating
 Raffinose and stachyose, because of their  Hydroxyethylcellulose – thickening agent and
unique glycosidic bonds, cannot be broken ingredient in the formulation of artificial tears
down into their simple sugars.  Hydroxypropylcellulose – stabilizer,
thickener, binder
Trisaccharides: Raffinose  Pyroxylin or soluble guncotton – product
 With acid – sucrose + galactose obtained by the action of the mixture of Nitric
 With yeast – melobiose + fructose acid and sulfuric acid in cotton.
 Gentianose  Purified Rayon: a fibrous, bleached,
 With acid – 2 glucose + fructose regenerated cellulose and it is used as a
 With emulsin – sucrose + glucose surgical aid
 With invertase – fructose + gentiabiose Other Homoglycan
 Glycogen: animal starch, important reserved
carbohydrates of animal tissue
 Xylans, mannans and galactans: difficult to
isolate in a pure form
Tetrasaccharides: Stachyose With acid will yield  Hemicellulose: occurs in the cell wall with
2 galactose + glucose + fructose cellulose and pectic substances
 Lichenin or lichen starch: resembles
M3 Lesson 3: Polysaccharides and Polysaccharide- cellulose but molecule contains 25% β- 1,3
containing Drugs glycosidic bonds

Lesson 3: Polysaccharides and Polysaccharide- HETEROGLYCAN

containing Drugs  Gum - dissolve in water readily’ plant
POLYSACCHARIDES hydrocolloids classified as anionic or non-
Glycan: Monosaccharide polymer ionic polysaccharide, consist of linear
polymer or branched polymer
HOMOGLYCAN: one type of monosaccharide units  A linear polymer is less soluble, yields
Starch: solution with greater viscosity, its solution is
Amylose (β – amylose), about 20%; more soluble in less stable (tend to precipitate) è could
water, with I2 TS ___ significantly influence the shelf life of product
 200-300 units of glucopyranose formulation
Amylopectin (α – amylose), about 80% , soluble in  Branched hydrocolloids – form gels rather
water, branched α- 1,4 glycosidic bonds than viscous solution at higher concentration
 (20-26 units), with I2 TS _________1000 tend to be tacky when moist and rehydrate
units of glucopyranose more readily

 Hetastarch: semisynthetic- 90% amylopectin, COMMON SOURCES

plasma expander, adjunct therapy in the  Exudate from trees and shrub – seal damage
treatment of shock caused by hemorrhage, bark and preserve from dehydration (acacia,
burn, surgery, sepsis karaya, tragacanth)
 Inulin: D- fructofuranose abundant in  Seed gum – serve as polysaccharide food
Asteraceae, used in culture media as a reservoir (guar, locust bean, psyllium)
fermentative identifying agent for certain  Microbial gum – fermentation(dextran,
bacteria and in special laboratory methods xanthan)
for the evaluation of renal function
  Marine gum - reserve food (agar, algin, M4 Glycosides
carrageenan) Introduction
 Plant extract - pectins
Glycoside 1.JPG

EXAMPLES OF GUM

Tragacanth: SN: Astragalus gummifer FN: Fabaceae bookmark_lg.svgOverview

 contains 60%-70% bassorin that swell in
water but do not dissolve
 Contains 30% tragacanthin more water
soluble
 used as emulsifying, suspending agent,
demulcent and an emollient (oil in resin, The term glycoside is a generic term for a natural
insoluble powders, hand lotion, cloth printing) product that is chemically bound to a sugar. Thus the
Acacia: SN: Acacia senegal FN: Fabaceae glycoside is composed of parts: the sugar and the
 contains arabin (Ca, Mg and K salts Arabic aglycone. The aglycone may be a terpene, a
acid) flavonoid, a coumarin, or practically any other natural
 used as suspending agent, demulcent and product. If the aglycone is a triterpene, it is sometimes
emollient, adhesive & binder referred to as a genin (e.g. protoaescigenin)
 Substitute for tragacanth
Ghatti Gum or Indian Gum SN: Anogeissus latifolia - Glycosides are very common in nature and
Combretaceae provide extra chemical diversity and structural
 substitute for acacia, forms dispersion with complexity in natural products. There are two basic
cold water, dispersion is more viscous. classes of glycosides: the C-glycosides, in which the
Karaya gum SN: Sterculia urens – Sterculiaceae sugar is attached to the aglycone through a carbon-
 least soluble among exudates carbon bond, and the O-glycosides in which the sugar
 bulk laxative, suspending agent, used in is connected to the aglycone through an oxygen-
wave set solution and skin lotion carbon bond. Glycosides are usually more polar than
Sodium Alginate - algin (alginic acid): principal the aglycone, and glycoside formation generally
constituent of brown algae increases water solubility. This may allow the
SN: Macrocystis pyrifera – Lessoniaceae producing organism to transport and store the
 suspending agent, tablet binder, thickening glycoside more effectively (Heinrich, M et al, 2018).
agent formation of a firm gel
Agar / Japanese isinglass SN: Gelidium cartilagineum M4 Lesson 1: Introduction to Glycosides
or Gracilaria confervoides FN: Gelidiaceae Lesson 1: Introduction to Glycosides
 laxative, suspending, emulsifying and Glycosides are compounds that yield one or more
gelating agent, tablet excipient & disintegrant sugar among the product of hydrolysis.
 used as bacteriologic culture media
Carrageenan SN: Chondrus crispus / Gigartina
mamillosa FN: Gigartinaceae
 forms gel & give stability to emulsion &
suspension, demulcent bulk laxative.
Plantago seed: SN: Plantago psyllium FN:
Plantaginaceae
 the husk is cathartic- swelling of the gum of An example is the glycoside, salicin:
the seed coat thus giving bulk & lubrication
should be taken w/ considerable amount of
water
Guar Gum SN: Cyamopsis tetragonolobus FN:
Fabaceae
 Galactomannan from powdered seed
 bulk laxative, tablet and disintegrator Glycosides are considered sugar ethers. The
nonsugar component is known as the aglycone; the
Locust bean gum SN: Ceratonia siliqua- Fabaceae sugar component is called the glycone.
 Used as a substitute for chocolates >Both alpha and beta glycosides are possible,
 thickener and stabilizer depending on the stereo configuration of the
Xanthan gum SN: Xanthomonas campestris glycosidic linkage. However, only beta forms occur in
 pseudoplastic properties, plants.
Pectin: middle lamella of seed-bearing plants; the
 insoluble form is called protopectin. Obtained Emulsin and most other natural enzymes hydrolyze
by dilute acid extraction of the inner portion only the beta varieties.
of the rind of citrus fruit. A solution of pectin
can be precipitated by alcohol (salting out). CLASSIFICATION OF GLYCOSIDES BASED ON
Used as a protectant, suspending agent; AGLYCON
anti-diarrheal formulation (Kaopectate).
 Alcoholic and/or phenolic Glycosides
 Aldehyde Glycosides
  Cyanogenic Glycosides Other phenolics include: (1) Eugenol – phenolic
 Anthracene or anthraquinone Glycosides phenylpropane (2) Vanillin – phenolic aldehydes (3)
 Steroidal Glycosides Salicylic acid (4) Ferulic acid (5) Caffeic acid

Classification of Glycosides based on aglycone  Meadowsweet SN: Filipendula ulmaria

 Coumarin glycosides Spirea ulmaria FN: Rosaceae; Use/s:
 Chromone glycosides diuretic; traditionally used as anti-
 Flavonoidal glycosides inflammatory, astringent and stomachic
 Sulfur-containing or thioglycosides agent
 Alkaloidal glycosides  Oil of Wintergreen: SN: Gaultheria
procumbens; Gaultheria fragrantissima;
 Physical and Chemical Properties
Betula lenta; Use/s: Counterirritant, Soothing
effect
MEDICINAL IMPORTANCE OF GLYCOSIDES
1. Cardiac drugs: cardiotonic glycosides e.g:  Willow bark: Salix purpurea (purple)
digitalis glycosides, strophanthus, squill. Constituents: (1) Salicin – phenolic
2. Laxatives: anthraquinone glycosides e.g: glycosides
senna, aloes, rhubarb, cascara, frangula.  Black haw bark SN: Viburnum prunifolium
3. Counter-irritants: thioglycosides and their FN: Caprifoliaceae Constituents: 0.2%
hydrolytic products e.g: allylisothiocyanate Salicin, Iso-valeric acid Reported use/s: Tx of
4. Analgesics: methylsalicylate a hydrolytic dysmenorrhea, Threatened abortion, asthma
product of gaultherin.  Hops SN: Humulus lupulus FN:
5. Anti-rheumatic: e.g: salicin. Caprofoliaceae Constituents: Humulene,
6. Some glycosides are claimed to reduce the Phloroglucinol derivatives like humulone,
capillary fragility: e.g: flavonoidal glycosides, lupulone, Xanthohumol; Use/s: Anti –
rutin, hisperidin. estrogen, Anti – oxidant, Mild sedative
7. Anti-inflammatory: the glycoside glycyrrhizin  Male Fern (Filix Mas) SN: Dryopteris filix-
has a demulcent, expectorant and mas FN: Polypodiaceae; Constituent:
antispasmodic action. Phloroglucinol derivatives; Use:
8. More recently as an anticancer agent e.g., Anthelmintic (tapeworm)
amygdalin known in the U.S. as Laetrile.  Kamala: SN: Mallotus philippinensis
FN: Euphorbiaceae Constituents:
CLASSIFICATION AND NOMENCLATURE Phloroglucinol derivative like rottlerin and
ACCORDING TO THE FOLLOWING: isorottlerin, Resins, Wax Use:
1. The types of glycosidic linkage: α- glycoside, Anthelmintic
β-glycosides  Wood tar (Stockholm tar) FN: Pinaceae;
2. The chemical group of the aglycone involved Characteristics: prepared by destructive
in the acetal union: O-glycoside (OH group), distillation (methanol, acetone), blackish
S-glycoside (SH group), N-glycoside (NH semi liquid, characteristics odor Use: Tx
group), C-glycoside (C group). psoriasis
3. the nature of the simple sugar component of  Coal tar: Prepared by destructive distillation
the glycoside. of bituminous coal; Characteristics: Black
4. The number of the monosaccharides in the viscous liquid, Forms alkaline solution with
sugar moiety: Monoside (one water, Petroleum spirit extract has a blue
monosaccharide) e.g., salicin; Biosides (two fluorescence enhanced by UV light
monosaccharide) e.g., gentobioside; Use: Treatment of psoriasis
Triosides (three monosaccharide) e.g.,  Vanilla (Vanilla Pods): SN: Vanilla fragrans
strophanthotriose. FN: Orchidaceae; Constituents:
5. The physiological or pharmacological Glucovanillin (vanilloside), glucovanillic
activity/therapeutic classification: laxative alcohol; Vanillin BP: aldehyde corresponding
glycosides; cardiac glycosides. to methyl-protocathechuic acid Uses:
6. The correlation to the parent natural Flavoring agents, Coloring agents
glycoside: Primary glycosides e.g.,  Bearberry (Uva ursi) SN: Arctostaphylos uva-
amygdalin, purpurea glycoside A; Secondary ursi FN: Ericaceae; Constituents:
glycosides e.g., prunasin, digitoxin. Arbutin, Corilagin, Pyroside, several esters of
7. The plant families. arbutin, quercitin, gallic acid. Elagic acid, and
ursolic acid. Arbutin: When hydrolysed with
M4 Lesson 2 Part 1: Plants-containing Glycosides acids or with emulsin it yields glucose and
Lesson 2: Plants-containing Glycosides hydroquinone. Methylarbutin, contributes to
the diuretic and urinary antiseptic action of
SIMPLE PHENOLIC COMPOUNDS the leave; Use/s: Urinary Antiseptic, Diuretic
 Catechol: present in Kola seeds and leaves (due to hydroquinone), Astringents
of Gaultheria spp.; the derivatives are the  Capsicum (Red Peppers) SN: Capsicum
urushiol phenols of the poison oak and annuum, frutescens FN: Solanaceae;
poison ivy Constituents: Capsaicin, Vitamin C,
 Resorcinol: Constitute the narcotic principle Thiamine, Red carotenoids – capsanthin and
of cannabis capsorubin.; Use/s: Condiments – cayenne
 Hydroquinone pepper; Internally as atonic dyspepsia;
 Externally as a counter-irritant (plaster, secretion of water and electrolyte into the
ointment); Used as a relief for rheumatism large intestine.
 Hesperidin: Occurs in various citrus fruits;  Stimulant laxative: habit-forming, may result
Found in the root bark of rasaceous plants; in laxative dependence and loss of normal
Rutin – Rutaceae – Vitamin P bowel function.
Official anthraquinone drugs in B.P and U.S.P.: Senna
leaf & senna fruit (pod), Aloes, Cascara tablets, elixir,
dry extract, liquid extract, Rhubarb powdered, tincture,
Danthrone, Frangula bark

Cascara Sagrada: Rhamnus purshianus Decandolle

FN: Rhamnaceae
aka ”sacred bark”; Cathartic used in the correction of
COUMARIN GLYCOSIDES: Derivative of benzo-α- habitual constipation; Obtained by percolation and
pyrone, Lactone of O-hydroxycinnamic acid. evaporation; Bitter taste and activity may be reduced
by treating extract with alkaline earth or Magnesium
Umbelliferone [7-hydroxy coumarin] is the lactone of oxide
umbellic acid which occurs both in the free state and
 Casanthranol – purified, water-soluble
in the form of glycosides in some resins of the
mixture of anthranol glycosides extracted
Umbelliferae.
from cascara sagrada. the dried bark of
cascara sagrada specified that the collection
In ammoniacal solution, these compounds produce
must be made at least one year before the
blue, blue-green, or violet fluorescence (conjugated
bark is used (fresh bark contains an emetic
double bond system).
principle).
 Constituents: Four primary glycosides:
Furanocoumarins – responsible for the effect on the
Cascarosides A&B (glycosides of barbaloin)
drug's bioavailability resulting from the consumption of
grapefruit juice.
Cascarosides C & D (glycosides of chrysaloin)
 Angelica Roots SN: Angelica archangelica L.
FN: Umbelliferae; Constituents:
 Two aloins (secondary glycosides):
Furanocoumarins, Bergapten, Angelicin,
o Barbaloin derived from (C-10-C-
Archangelicin, Apterin, Marmesin and
psoralen glycoside) of aloe-emodin anthrone
o Chrysaloin derived from (C-10-C-
 Melilot SN: Melilotus officinalis
FN: Leguminosae; Constituent/s: Melilotic glycoside) of chrysophanol
acid, Caffeic acid, o-Coumaric acid anthrone.
 Tonco seed: SN: Dipteryx odorata,  Frangula (Buckthorn Bark) SN: Rhamnus
oppositifolia FN: Leguminosae; frangula Linne FN: Rhamnaceae;
Constituents: 1 – 3% coumarin, to liberate Constituents: Frangulins A & B,
the coumarin, maceration of beans for 24 glucofrangulins A & B
hours and drying, whereby a fermentation o It should be aged 1 year to reduce
process takes place. Coumarin crystals are harsh action of the glycosides to a
visible below the epidermis of the seed. milder form.
OTHER LACTONE o Frangulin (frangula emodin
 Cantharides/Blistering Flies/Spanish flies rhamnoside); Glucofrangulin
SN: Cantharis vesicatoria FN: Meloidae; (frangula emodin glucorhamnoside).
Constituent: Cantharidin Use: Vesicating  Aloe or Aloes: Aloe barbadensis Miller
agents, irritants (Curacao aloe), Aloe ferox Miller (Cape
 Dicumarol: MOA: competitive inhibitor of aloe), Aloe africana Miller Aloe spicata Baker
Vitamin K, preventing the formation of FN: Liliaceae
prothrombin; USE: Anticoagulant o Reddish black or brownish-black
with a nauseating and bitter taste
and a disagreeable characteristic
odor.
o Dried latex of the leaves of Aloe
barbadensis
o Constituent/s: Aloin A
(Barbaloin); Aloin B (Isobarbaloin)
o USE: A pharmaceutic aid for
Compound Benzoin Tincture and
Cathartic
 Rhubarb aka Rheum / Chinese Rhubarb SN:
Melilotus officinalis Cantharis vesicatoria Rheum officinale Baillon, Rheum plamatum
Linne FN: Polygonaceae
ANTHRAQUINONE GLYCOSIDE o Constituent: Rhein anthrones
 Stimulant cathartic: exert their action by o Use: Drastic cathartic action
increasing the tone of the smooth muscle in (purgative)
the wall of the colon and stimulate the
Indian rhubarb aka Himalayan rhubarb SN: Rheum o Constituent & use: Alkannin - Red
emodi Wallion, Rheum webbianum Royle FN: naphthoquinones
Polygonaceae
o Constituents: Rhein, rhein anthrone,
chrysophanol and aloe emodin,
Dianthrones of heteroanthrone Alkanna tinctoria
types are palmidin A,B,C, rheidins,
sennosides A&B and their oxalate
esters (sennosides E&F).
o Tannins present in rhubarb makes
the drug constipating.
o Small doses: no purgative action
but acts as intestinal astringent, FLAVONOIDAL GLYCOSIDES: The largest group of
Large doses: purgation naturally occurring phenols.
 Senna/Senna leaves SN: Cassia acutifolia
Delile – Alexandria or Cassia SennaCassia It includes anthocyanin and leucoanthocyanin;
angustifolia , Vahl – Tinnevelly Senna Derived from flavan, have a basic C-15 skeleton
FN: Fabaceae
o Constituent: Sennosides A and B Classified according to the oxidation level of central
((Sennidin A+B))→ rhein dianthrone pyran ring: Flavones, isoflavones, flavonols,
o Use/s: Purgative (liquid extract, flavanones, (true flavanoids) anthocyanidins,
elixir or as tablets prepared from dry chalcones, and aurones. True flavones are 2-phenyl
extract) chromones, while isoflavones are 3-phenyl
o Danthrone: an only compound chromones derivative.
which is used to some extent in
current medicine; used as a Chalcones: have no central pyrone ring; not true
standard in colorimetric assays of flavonoidal compounds; chemically phenyl-styryl
anthraquinone glycosides. ketone, or benzylidene acetophenone

Aurones: are oxidized forms that are obtained by

enzymatic oxidation; have five membered ring
(instead of the central pyrone ring of the normal
flavonoidal structure)

Properties of Flavonoids
 Dissolve in alkalis give an intense yellow
Rhamnus purshianus Cassia acutifolia Rheum officinale
color solution, on the addition of acid
become colorless.
NAPHTHOQUINONE GLYCOSIDES: produced by  Exhibit strong fluorescence under UV light.
higher plants, fungi, and actinomycetes  Soluble in water and alcohol.
Uses: Fungicidal, antibacterial, insecticides,
 Ethylacetate is the solvent of choice for the
phytotoxic, cytostatic, and anticarcinogenic
extraction of flavonoids from aqueous
solution.
 Juglans regia: FN: Juglandaceae 4β-D-
 Buchu leaves: SN: Barosma crenulata
glucoside of α hydroguglone (leaves of
FN: Rutaceae; Constituent/s: Diosmin
walnut tree)
- flavone glycoside; Use/s: Diuretic and
 Henna SN: Lawsonia inermis FN: diaphoretic action
Lythraceae o Rutin and quercetrin (flavonol
o Constituent/s: Lawsone
glycosides): Rutin occurs in the
(hydroxynaphthoquinone) –colorant; leaves of buckwheat; It is the 3-
Isoplumbagin – anti-inflammatory rhamnoglucoside (called rutinose)
o Use/s: hair dye, astringent (stem- of the genin quercitin.
bark), Tx for jaundice, enlargement o It gives on hydrolysis the aglycone
of the liver and spleen (quercitin) beside one molecule of
 Lithospermus (Family Name: Boraginaceae): glucose, and one molecule of
reported hormonal activities; Shikonin – rhamnose. Use: Rutin is used to
naphthoquinone derivative; Scyllitol – cyclitol decrease capillary fragility; It is a
Cyanoglucoside – lithospermocide biflavonoids that plays a true
o Use – Purple roots tx burns, vitamin function.
inflammation, wounds and ulcers  Quercitrin is quercitin 3-O-rhamnoside from
 Lithospermum arvense (L. rudelare) – oral Quercus tinctoria bark
contraceptive agents, suppress estrus cycle.  Quercitrin yield upon acid hydrolysis
 Alkana root (Alkanet/Anchusae radix) SN: rhamnose and quercetin.
Alkanna tinctoria  Hesperidin: it is the main flavonoidal
FN:Boraginaceae glycoside of citrus fruits; upon hydrolysis by
acid, hesperidin gives rhamnose, glucose
and hesperitin.
 o Uses: Hesperidin appears to be  Forms colloidal solution in water that foams
identical to vitamin P (citrin); It is upon shaking, colorless and optically active.
necessary for absorption and  Have bitter, acrid taste; irritating to the
retention of vitamin C that lead to mucous membrane; destroy red blood cell by
decrease capillary fragility; s and are toxic especially to cold-blooded
Decrease CVD and HTN. animals
o Increase capillary resistance and  Sapotoxin- poisonous saponin used for
decrease vitamin C & P deficiency. controlling schistosomiasis snails.
o They are recommended in the  2 types of sapogenin: Steroidal (25)- in
treatment of thrombopenia (blood monocot families; Triterpenoidal (30)- in dicot
coagulation). families
o They are reported of value in the  Both types of saponins have the glycosidic
treatment of influenza when given linkage at position 3.
with ascorbic acid.  Test: Froth test - formation of bubbles;
 Silymarin: SN: Silybum marianum FN: Hemolytic test - halozone
Compositae Effective lipotropic and
hepato-protective therapy; It is a free radical MEDICINAL IMPORTANCE OF SAPONINS
scavenger (anti-oxidant); supportive  The steroidal saponins are structurally
treatment of acute and chronic alcoholic related to modern synthetic compounds that
poisoning and toxin induce hepatitis; It is have a therapeutic significance, such as
used for the treatment of liver cirrhosis adrenocortecoids and sex hormones.
caused by plant toxins (mushroom, amanita),  They are suitable precursors in the partial
silymarin IV synthesis of these hormones, e.g., Diosgenin
o Available in the market in the form (sapogenins) isolated from the rhizome of
of tablets, effervescent granules. Dioscoria
o Trade name Legalon®  Saponins increase the rate of absorption of
many pharmacologically active substances
ANTHOCYANIDIN AND ITS GLYCOSIDE (e.g., cardiac glycosides).
 Anthocyanidins are flavonoids structurally  Many saponin-containing drugs are used as
related to flavones. expectorants (e.g., Ipecac, Senaga and
 Anthocyanins – glycosides of anthocyanidins liquorice) as their contents of saponins
Etiolohy: antho – flower & kyanos – blue stimulate the bronchial secretion and also
 Responsible for the permanent blue, purple, activate the ciliary epithelium of the bronchi
violet, mauve, and red color of flower, fruits  The triterpenoidal saponin glycoside,
and leaves of higher plants. Also known as glycyrrhizin, is the main sweet principle of
sap pigments. liquorice it is also used as demulcent,
 Leucoanthocyanin: upon hydrolysis yields expectorant, and antispasmodic action.
sugar and leucoanthocyanidin  It is calcium and potassium salts of
 Plant materials boiled with diluted acids glycyrrhizic acid, which is the diglucuronic
gives intense red or violet color acid glycoside of glycyrrhitinic acid.
 Lignans and Lignins: dimeric compounds
formed essentially by the union of 2 SAPONINS DRUGS OFFICIALLY B.P AND U.S.P:
molecules of phenylpropene derivatives.  Quillaia bark: used as an emulsifier.
Optically active; arise by stereospecific,  Liquorice root: used as flavoring agent and
reductive coupling between the middle expectorant
carbons of the side-chain monomer  Glycyrrhiza (Licorice root); Glycyrrhiza glabra
 Neolignans - derived same as lignans, but Linne (Fabaceae): Glycyrrhizin- 50x as
the C6-C3 moieties are linked head to tail or sweet as sugar but once converted to its
head to head and not through β-β’carbons. algyone glycyrrhetic acid its loses its
sweetness; Use/s: Demulcent, expectorant,
increase fluid retention.
o Glycyrrhetic acid- used in
dermatological practice as anti
inflammatory.
o Licorice root extract- use in the tx of
peptic ulcer & Addison’s disease.
 Ginseng SN: Panax quinquefolius Linne
(American ginseng) ginseng (Asian ginseng)
M4 Lesson 2 Part 2: Plants-containing Glycosides o Constituent/s: Ginsenosides,
Lesson 2 Part 2: Plants-containing Glycosides panaxoside and
chikusetsusaponins
SAPONIN GLYCOSIDES NOTE: very difficult to purify o Use/s: Tonic, stimulant, diuretic and
 Saponins are a group of amorphous colloidal carminative, adaptogenic (anti
glycosides which is widely distributed in the stress) in the Orient-anemia,
higher plants. diabetes, insomnia, neurasthenia,
 They are excellent emulsifying agents gastritis and sexual impotence
(modify surface tension); Formerly used as ADAPTOGENIC
detergents to replace soap (e.g., quillaia).
  Sarsaparilla SN: Panax quinquefolius ; mustard and white mustard seed
Constituent/s: Sarsaponin, smilagen Use: respectively.
flavoring agent  Importance in treatment of cancer:
 Dioscorea: Dioscin- diosgenin o Mustard: idole 3-carbinol derived
from indolylmethyl glucosinolate
reduce risk of estradiol- linked
mammary cancer
o Brocolli: 4-methyl sulfinyl
isothiocyanate induce carcinogenic
protective enzyme.
 Sinigrin gives upon hydrolysis, glucose,
Panax quinquefolius Panax quinquefolius Glycyrrhiza glabra allylisothiocyanate (volatile oil of mustard)
and potassium acid sulphate.
 Hydrolysis of the glycoside sinalbin gives a
CYANOGENIC GLYCOSIDES: Yields HCN upon phenolic isothiocyanate (Acrinyl
hydrolysis, therefore, making it toxic isothiocyanate), glucose and the acid
 The aglycone part is a derivative of sulphate of a quaternary alkaloid, sinapine.
benzaldehyde cyanohydrin of a carbonyl  Black and white mustard seeds are used as
compound (condensation product of HCN rubefacients and counter irritants.
with an aldehyde or ketone);  Major role in plants: Feeding deterrents
 Detected with Guignard’s reagent gives against insect and mammals Sulfur – Atom:
yellow to maroon Brassicaceae
 Picrate paper test – brown to brick red color  Reported to have anticancer property indole
 Amygdalin (D-Mandelonitrile gentiobioside): 3-carbinol derived from indolylmethyl
the most widely distributed cyanophore glucosinolate reduce the risk of estrogen
glycoside. linked breast cancer.
 Amygdalin - in Laetrile or vitamin B17  Methylsulfinyl isothiocyante induce
claimed to be anticancer and control sickle anticarcinogenic protective enzymes
cell anemia.  Black mustard SN: Sinapis nigra or
 It occurs in several Prunus species, and is brown/black mustard Brassica nigra Linne
obtained from bitter almonds (Prunus Koch; Brassica juncea Linne czerniaew
amygdalus amara Family Rosaceae). FN: Brassicaceae; Constituent/s: Sinigrin-
 Acid hydrolysis of amygdalin split two mustard oil S=C=N-CH2-CH=CH2,
molecules of glucose and one molecule of Use/s: Local irritant & emetic
mandelonitrile. The latter decomposes  White mustard SN: Brassica alba Hooker
spontaneously to form benzaldehyde and fillius or Sinapis alba FN:
HCN. Brassicaceae; Sinalbin upon hydrolysis by
 Wild cherry SN: Prunus virginiana Wild black enzyme Myrosinase yields p-
cherry tree SN: Prunus virginiana, hydroxybenzyl isothiocyanate
Prunus serotina Ehrhart (Rosaceae);  Garlic (other organosulfur drugs)SN: Allium
Constituent: Prunasin- formed by partial sativum line Family Name: Liliaceae; Alliin
hydrolysis of amygdalin; Prunase, p- [(+)-S-allyl-L-cysteine sulfoxide]; Comes with
coumaric acid; Use/s: Sedative, has reported contact with enzyme alliinase when garlic
anticancer claims cells are crushed and is converted to Allicin
 Apricot pits SN: Prunus armeniaca (diallyl thiosulfate)
(Rosaceae) Contains amygdalin and emulsin  Allicin- has a potent antibacterial effect,
o Emulsin- an enzyme that antihyperlipidemic and inhibits platelet
hydrolyzes glycoside releasing toxic aggregation
cyanides
o Not use for tx cancer because of its ALCOHOL GLYCOSIDES
potential danger.  Salicin (salicyl alcohol) Species of Salix and
Populus; Salix pupurea and Salix fragilis
FN: Salicaceae
 Prunus virginianas Salicin is classified as:
o Alcoholic glycoside, as it contains
free primary alcoholic group.
o A phenolic glycoside, as its
aglycone is phenolic in nature.

PROPERTIES OF SALICIN
ISOTHIOCYANATE GLYCOSIDES  Principal commercial source is Salix fragilis.
 A number of plants of the family Cruciferae  Salicin is used for many years as a remedy
yield glycosides containing sulphur. in the treatment of fever and rheumatism.
 Hydrolysis of these, yield volatile genins of  Now used as an analgesic-antipyretic in case
thiocyanate structure e.g., mustard oils. of periodic fever.
 The best known compounds Sinigrin and  Better tolerated in the stomach than sodium
Sinalbin, two glycosides occurring in black salicylate, asprin and other antipyretics and
 anti-inflammatory agents, which have largely  Black Indian Hemp aka Dog bane/ Canadian
displaced in medical practice. hemp SN: Apocynum cannabinum Linne
 Salicin is hydrolyzed by the enzyme emulsin FN: Apoynaceae
into saligenin (Salicyl alcohol) and glucose. o Principal constituents: cymarin
 Acid hydrolysis of salicin gives glucose and a  Adonis/ Pheasant Eye SN: Adonis aestivalis
phenolic ether called saliretin which is a FN: Ranunculaceae; Constituent/s:
condensation product of two molecules of Adonitoxin Cymarin K-stophantin
 Black Hellerebore/ Christmas rose SN: Dried
rhizosomes and root of Helleborus niger
 Salix pupurea Linne FN: Ranunculaceae) Possesses
cardiac stimulant properties in contrast to
Green Hellebore
 Oleander (Adelfa) SN: Nerium oleander
Linne FN: Apocynaceae Principal
constituents: Oleandrin Used to treat
ALDEHYDE cardiac insufficiency.
GLYCOSIDES  Strophanthus Dried, ripe seed of
Vanilla aka vanilla bean Strophanthus kombe Oliver, Strophantus
 Mexican or Bourbon Vanilla- Vanilla hispidus FN: Apocynaceae;
planifolia Andrews (FN: Orchidaceae) Principal constituent: K-strophanthoside
 Tahiti Vanilla- Vanilla tahitensis W Moore (stroposide); Strophanthidin
 Constituent/s: Glucovanillin (avenein) and  Ouabain aka G-strophanthin From seed of
glucovanillic alcohol; Glucovanillin is a Strophanthus gratus Wall et Hook. Baillon or
glycosidal constituent of green vanilla from wood of Acokanthera FN:
pods.Use: Vanillin is widely used as a Apocynaceae extremely poisonous
flavoring agent.  Squill/ Squill bulb Dried, fleshy, inner scales
of the bulb of the white variety of Urginea
 Vanilla planifolia maritime Linne Baker or Urginea indica
Kunth (Liliaceae) aka Mediterrian Squill
respectively
o Principal constituent: scillaren A;
glucoscillaren A; proscillaridin A.
o Uses: expectorant, emetic,
cardiotonic and diuretic.
 Red squill Bulb or bulb scales of red variety
of Urgenea maritime linne Baker (Liliaceae)
M4 Lesson 2 Part 3: Plants-containing Glycosides o Use: rat poison
Lesson 2 Part 3: Plants-containing Glycosides
CARDIAC GLYCOSIDE CARDIAC GLYCOSIDES ADDITIONAL
 Steroidal in character with CPPP nucleus.  The genins of all cardiac glycosides are
 Powerful action on the cardiac muscle: steroidal in nature that acts as cardiotonic
increase muscle contractility or tone of agents.
cardiac muscle.  They are characterized by their highly
 Steroid aglycones: specific action cardiac muscle, increasing
o Cardenolides/ C23 steroid/ 5 tone, excitability and contractility of this
member lactone ring. muscle, thus allowing the weakened heart to
o Bufadenolides/ C24 steroid/ 6 function more efficiently.
member lactone ring.  Cardiac glycosides that α-β unsaturated 5-
 Identification Test: membered lactose rings in position C-17 are
o Keller Killiani – 2-deoxy sugar; known as cardenolides. Represented by the
reddish brown color turn to blue digitalis and strophanthus group.
purple  Digitalis glycosides contain angular methyl
o Liebermann Burchard – steroid; group at C-10,
blue green to pink purple or violet;  Strophanthus glycoside is characterized by
o Kedde test - lactone unsaturated; the presence of either an aldehydic (CHO) or
purple. primary alcoholic (C`H2OH) group at C-10.
 Digitalis or Foxgloves SN: Digitalis purpurea  Cardiac agents that have a doubly
FN: Scrophulariaceae; Constituent/s: unsaturated 6-membered lactone ring in
Digitoxin; Gitoxin; Gitaloxin; Animal used in position C-17 are referred to as
the assay: guinea pig, frog, cats, pigeon. Bufadienolides.
 Grecian Foxglove SN: Digitalis lanata  This group includes the squill glycosides and
Ehrhart FN: Scophulariaceae the toad venom, Bufotoxin.
 Lily of the Valley SN: Convallaria majalis  The glycone portion at position C-3 of
Linne FN: Liliaceae cardiac glycosides may contain four
o Principal glycosides: Convallatoxin monosaccharide molecules linked in series.
(strophanthidin and rhamnose) Thus, from a single genin one may have a
monoside, a bioside, a trioside or a tetroside.
  With the exception of D-glucose and L- 3.Digoxin injection contain 0.0025% digoxin
rhamnose, all the other sugars that are found 4.Digoxin tablets contain 250μg/tablet
in cardiac glycosides are uncommon deoxy- 5.Gitalin, lanatoside C, deslanoside,
sugars e.g., Digitoxose, Cymarose, strophanthus, strophanthin, ouabain and
Thevetose. squill.
CYSTEINE DERIVATIVES
The Cardenolides – Digitalis Group  Occur as sulfoxides in the genus Allium
 Digitis purpurea, D. lanata, D. lutea and D.  Responsible for the lachrymatory factor of
thapsi onions and garlic.
 The primary glycosides Lanatoside A,  S-(trans-propen-1-yl)-cysteine sulfoxide –
Lanatoside B, Lanatoside C are acted by a present in onion
specific enzyme which split the terminal  S-allyl derivative – present in garlic.
glucose, give the secondary glycosides
acetyldigitoxin, acetylgitoxin and
acetyldigoxin Garlic – Allium sativum, Liliaceae Constituents:
 The deacetyl-lanatosides A, B, and C can be Alliin (Alliin –Allinaseè allicin.)
obtained by the alkaline hydrolysis of the  Diallydisulfide, diallyltrisulfide – gives the
corresponding lanatosides. characteristic garlic odor
 Digitoxin, gitoxin and digoxin are obtained by MISCELLANEOUS GLYCOSIDES
the action of alkali on their acetyl-derivatives.
 Steroidal alkaloidal glycosides
The Cardenolides – Strophanthus Group o Solanaceae and Liliaceae
 The glycoside K-strophanthoside (a trioside), o With hemolytic property
K-strophanthin B (bioside) and cymarin (a o α- solanin – Present in potato
monoside) were isolated from different (Solanum tuberosum)
strophanthus species. o Soladulcin - Bitter-sweet (Solanum
 The primary glycoside K-strophanthoside dulcamara)
gives by hydrolysis one molecule of glucose o Tomatin – Tomato (Lycopersicon
and the secondary glycoside K- esculentum)
strophanthoside B or K- strophanthin B; o Rubijervin – (Veratrum spp.)
 The later gives by hydrolysis one molecule of  Glycosidal resins from Convolvulaceae
glucose and the tertiary glycoside cymarin, o Jalap and scammony
which on turn hydrolyze into the genin K-
o Upon hydrolysis will yield glucose,
strophanthidin and the deoxysugar
rhamnose, fucose, fatty acids and
cymarose.
hydroxyl derivatives
 The seeds of Strophanthus gratus contain
another glycoside named Ouabain or (G-
Glycosidal bitter principles
strophanthin), which yield on hydrolysis
 Glycosides with bitter taste, also referred to
rhamnose and the aglycone ouabagenin.
as “bitter principle”
 Ouabagenin differs from K-strophanthidin in
 Gentian root – gentiopicrin, gentiopicroside
having 2 additional (OH) groups at C-1 and
C-11 and having a 1ry alcoholic group at C-  Saffron – Picrocrocin/picrocroside
10 instead of the aldehydic group.  Cucurbitacins present in Cucurbitaceae
Betalains – give the bright color of flowers and fruits of
Bufadienolides: This group of cardioactive agents Cactaceae
includes the squill glycosides (the scillarins) and the  Nitrogenous anthocyanins
Toad poison (Bufotoxin).  Betacyanins – red – violet
 Betaxanthins – yellow
 The genins of squill glycosides differ from  Betanin – upon hydrolysis will yield
those of the cardenolides in two important betanidin(aglycone); indicaxanthin
aspects: Antibiotic glycosides
o They have six membered doubly  Streptomycin
unsaturated lactone ring in position  Streptidin (aglycone) – a nitrogen –
C-17. containing cyclohexane derivative
o They have at least one double bond  Streptobiosamine – glycine
in the steroid nucleus.

Physical and chemical properties of cardiac M5: Introduction

glycosides Introduction
 Medicinal Importance Overview
o Cardiotonics, CHF, rheumatic heart The term tannin (from tanna, an Old High German
disease, atherosclerosis, HTN. word for oak or fir tree, as in Tannenbaum refers to
o Diuretics (capillary of the kidneys the use of wood tannins from oak in tanning animal
are dialated). hides into leather; hence the words "tan" and
"tanning" for the treatment of leather. Heterogenous
Cardiac drugs Official in B.P. and USP group of HMW polyphenolic compounds with the
1. Digitalis leaf (digitalis tablets) capacity to from reversible and irreversible complexes
2. Digitoxin tablets 200μg/tablet
with proteins, polysaccharides, alkaloids, nucleic Lesson 2: Classification of Tannins
acids and minerals etc.
Hydrolyzable tannins – pyrogallol tannins
Tannins are secondary metabolites of plants,  these esters are easily hydrolyzed by
heterogenous, non-nitrogenous, HMW polyphenolic in tannase or HCl and H2SO4 to yield phenolic
nature. Complex substance usually occurs as acid and sugar; gallic acid or ellagic acid and
mixtures of polyphenols that are difficult to separate hexahydroxydiphenic acid
because they do not crystallize.  blue-black in color with FeCl3
 do not precipitate with Bromine T.S
1796: Seguin use tannin to denote substances in  Examples of hydrolyzable tannins:
plant extracts which were able to combine with protein o Gallitannins – gallic acids
of animal hides, prevent their putrefaction and convert o Ellagitannins - hexahydroxy-
them into leather. diphenic acid; ex: geraniin;
tellimagrandins 1 and 2
M5 Lesson 1: Introduction to Tannins  Examples: Myrobalon Bahera
Lesson 1: Introduction to Tannins Witch hazel

Tannins: are secondary metabolites of plants, non- Nonhydrolyzable or Condensed tannins

nitrogenous, phenolic in nature. The complex
substance usually occurs as mixtures of polyphenols  Heating with HCl acid yield phlobaphenes
that are difficult to separate because they do not like phloroglucinol/ dark green color with
crystallize. FeCl3
 They are not readily hydrolyzed to simpler
 1796: Seguin uses tannin to denote molecules and they do not contain a sugar
substances in plant extracts that are able to moiety.
combine with the protein of animal hides,  Can form phlobaphenes – give the
prevent their putrefaction and convert them characteristic red color to many drugs such
into leather. as red cinchona;
 Detection: Qualitatively by tanning test  The dark green color produced with FeCl3 –
(Goldbeater’s skin test); Quantitatively by catechol - tannins
adsorption on standard hide powder.  precipitate with Bromine T.S
o True tannins – MW ranging from
 Examples: black catechu, pale catechu, kino
1000 – 5000
o Solvent for extraction: water – M5 Lesson 3: Plant-containing Tannins
acetone or water-alcohol mixture. Lesson 3: Plant-containing Tannins
 Separation: Chromatography
 Properties of Tannin PLANTS CONTAINING CONDENSED TANNINS
o Non – crystallizable  Black Catechu (Heartwood) SN: Acacia
o Tannin + water = produce sharp catechu /Acacia chundra FN: Leguminosae
puckering taste, o Constituents: Contains catechin &
o They cause precipitation of gelatin quercetin
and alkaloids thus making it a o Chemical Test: it gives a pink color
protein precipitant. with vanillin & HCl; aqueous extract
o Protein precipitant/protein inhibitor of drug when treated with lime
o Present in greatest quantity in dead water gives a brown color
or drying cells o Use/s: Astringents, treatment of
o Contribute a protective function in ulcers, diarrhea, & in tanning
barks and heartwoods industry.
o Upon polymerization, it will produce  Pale Catechu Leaves SN: Uncaria gambir
an insoluble red-colored product FN: Rubiaceae
called as o Chemical Constituents: Chlorophyll,
o They form dark blue or greenish- catechu red & gambier fluorescein;
black soluble compounds with 7.33% catechins, 22-50%
FeCl3 and deep red with potassium catechutannic acid
ferricyanide and ammonia o Chemical Test: Alcoholic extract of
o They are precipitated by salts of Cu, drug when treated with NaOH &
Pb, Sn, and strong aqueous light petroleum ether shows green
potassium dichromate (or 1% fluorescence.
chromic acid) solution  Kinos (juice obtained from trunk of
 Commercial tannins: used in the leather Pterocarpus marsupium) FN: Leguminosae
industry: Obtained from quebracho, wattle, o Occurs as small shiny reddish black
chestnut and myrobalsams pieces Chemical Constituents &
Uses: Same as catechu
 Pharmaceutical tannins: prepared from oak
galls and yield glucose and gallic acid upon
hydrolysis
 PLANTS CONTAINING HYDROLYSABLE
M5 Lesson 2: Classification of Tannins TANNINS
 caffeol, enzymes & other phenolic
 Galls obtained from gall wasps Adleria principles. Use/s: Stimulant,
gallaetinctoria Family: Fagaceae diuretic
o Collection: Summer gall wasps lay o Chemical Test:
eggs on the twigs  It penetrates o Murexide test- caffeine when Δ with
the soft epidermis of the plant & HCl & potassium chlorate gives a
soon forms a larvae which residue which on exposure to
eventually develops into galls  ammonia vapors gives purple color.
Ideally galls should be collected o Caffeine forms a white precipitate
before the mature insect comes out. with tannin solution
o Chemical Constituents:
o Chinese galls contain 75% tannic  Tea - prepared leaves of Camelia sinensis
acid as compared to 60% in Turkish [Thea sinensis] Family: Theaceae
galls. Use: Astringent o Chemical Constituents: Caffeine,
o Extraction of tannic acid from gall: A theobromine, theophylline, oxidase
mixture of alcohol-ether is added to enzyme & tannins
galls  When water is added to this o Uses & chemical Tests: Same as
extract the tannic acid enters the coffee
alcohol layer  The ether layer can
be discarded  After precipitation OTHER PLANTS CONTAINING TANNINS
with a non-polar solvent it occurs as
a white shiny powder.  Hawthorn - from dried false fruit of Crataegus
 Nutgall Quercus infectoria (twig) – monogyna & C. laevigata Family: Rosaceae
(Fagaceae) Cynips tinctorius (insect) o Constituent/s: Fruits – 1 – 3%
o Larva- starch grains; oligomeric procyanidins
o Chrysalis stage - gallic acid( 3,4,5 o Use/s: Mild cardiac tonic
trihdroxy benzoic acid) a phenolic
acid  Alchemilla – Alchemilla xanthochloratannis
o Wings develop- tannic acid formed; Family: Rosaceae
o Insects emerge from the gall- tannic o Constituent/s: NLT 6% tannins
acid becomes more porous and expressed as pyrogallol;
called white gall. Ellagitannins
o Constituents: tannic acid (50-70%) o Use/s: Astringent against bleeding;
– it is a mixture of esters of gallic Diarrhea Menorrhagia
acid with glucose whose exact
composition varies according to its
source.– treatment of bedsores,
minor ulceration Galic acid 2-4 %
o Ellagic acid; Starch and resins
Gallotannic acids – mixture of
esters of gallic acid with glucose

 Myrobalon Fruits SN: Terminalia chebula

FN: Combretaceae
o Chemical Constituents: Gallic acid,
ellagic acid, glucose, fructose,
sorbitol & active constituent
chebulic acid.
o Uses: Astringent, wound healing
antiseptics
 Bahera Fruits SN: Terminalia belerica
FN: Combretaceae
o Chemical Constituents:
Gallic acid, ellagic acid
o Uses: Same as myrobalon

 Hamamelis leaf (Witch Hazel/ Hazel nut)

Leaves of Hamamelis virginiana FN:
Hamamelidaceae
o Constituents: Hamamelitannin –
astringent and hemostatic; Gallic
acid, resins, fats and bitter principle

PLANTS CONTAINING PSEUDO-TANNINS

 Coffee seeds SN: Coffee arabica Family:
Rubiaceae
o Chemical Constituents: Caffeine
which is salt of chlorogenic acid,