UNIT–4: BrIef oUTlINe of ImporTaNT

plaNT coNsTITUeNTs

Points to be covered in this topic

➡ INTRODUCTION
❖ Alkaloids
❖ Glycoside
❖ Terpenoids
❖ Volatile oil
❖ Tannins
❖ Resins

4. INTRODUCTION
Natural products (i.e. plant-derived chemicals) are important sources for drug
development. Since the chemical constituents of plants are complicated, pure
compounds must be obtained from extraction and isolation before structure
identification, bioactivity screening, and so on. New extraction, isolation, and
structural identification techniques and technologies have emerged in recent years,
speeding up the extraction and analysis of phytochemicals. In phytochemistry
research, extraction is the initial stage in separating the desired natural products
from the raw materials. Its goal is to obtain the objective chemical constituents to
the greatest extent possible while avoiding or reducing the solution of undesirable
compounds. Taking into consideration their utility in day-to-day life, following are
the few Phyto-pharmaceuticals of therapeutic importance that can be Studied
4.1 ALKALOIDS
4.1.1 Introduction of Alkaloids
Definition: Alkaloids may be defined as a class of naturally
occurring organic compounds mostly of plant origin and mostly
are basic in nature and contain at least one nitrogen atom in their
heterocyclic nucleus.
The term “alkaloid” was coined by Meissner, a German pharmacist, in 1819.
Examples include morphine, strychnine, quinine, ephedrine, nicotine, etc.
4.1.2 Alkaloids have following properties:
1. They are basic in nature.
2. They are mostly colorless, crystalline solids.
3. They are insoluble in water but soluble in organic solvents.
4. Alkaloids react with acids; as a consequence, they form water soluble salts.
5. Alkaloids are optically active compounds.
Exceptions:
• Some alkaloids are amorphous gums, while others are liquid and volatile in nature
like coniine, sparteine, nicotine etc.
• Some alkaloids are coloured in nature, e.g. betanidin is red, berberine is yellow
and salts of sanguinarine are copper red in colour.
• Some alkaloids are optically inactive e.g. Papaverine and Atropine.
4.1.3 Isolation of alkaloids
The specificity of the method of extraction depends upon the chemical nature of the
alkaloid to be extracted.
There are a few examples of isolation of alkaloids on a commercial scale.
Stas Otto process:
The powdered drug is moistened with water and mixed with lime, which combines
with acids, tannins and other phenolic substances.
The extraction is then completed using either crude petroleum ether or benzene.
Alkali that is aqueous is used to shake the organic layer. The remaining alkaloidal
salts in the aqueous solution are isolated, basified, and chloroform-extracted for
further purification.

4.1.4 Classification of alkaloids:

 Based on heterocyclic ring system:
BASIC RING
TYPE EXAMPLES
STRUCTURE
Pyridine and Piperidine Areca, Lobelia, Tobacco
Tropane (Piperidine + N- Belladonna, Coca, Duboisia, Datura,
methyl pyrrolidine) Hyoscyamus, Stramonium
Quinoline Camptotheca, Cinchona
Curare, Daruhaldi, Ipecacuanha,
Isoquinoline
Opium
Ergot, Nux-vomica, Physostigma,
Indole
Sarpagandha, Vinca

Imidazole Pilocarpus

Purine (pyrimidine / imidazole) Cocoa, Coffee, Kola, Tea

Steroidal Ashwagandha, Kurchi, Veratrum

Diterpene Aconite

Alkylamine (Amino alkaloid) Colchicum, Ephedra

Quinazoline Vasaka
Based on origin:
(a) True alkaloid – Nitrogen is present in the heterocyclic ring and originates from
amino acid.
E.g. Atropine, Morphine, Nicotine.
(b) Proto alkaloid – Contain nitrogen but not in ring system and originates from
amino acid.
E.g. Mescaline, Ephedrine, Colchicine.
(c) Pseudo alkaloid – Nitrogen is present in the heterocyclic ring but does not
originate from amino acid.
E.g. Purine (Caffeine, Tea), Terpenes.
4.1.5 Occurrence and distribution of Alkaloids
• In the animal and plant kingdoms, alkaloids are discovered to be widely dispersed,
but they are not found in algae or the lower groups of plants, with the exception of
one or two genera of fungi.
• The occurrence of alkaloids is not specific to certain parts of the plants, they are
found in multiple parts of a plant.
(i) Leaves – Hyoscyamus, Belladonna
(ii) Seeds – Areca, Nux-vomica
(iii) Stem – Camptotheca
(iv) Bark – Cinchona
(v) Roots – Aconite, Ipecac
(vi) Every part of plant – Vinca, Ephedra
4.1.6 Identification tests
(a) General test
1. Mayer’s test – Mayer’s reagent (Potassium mercuric iodide solution) →
Creamy precipitate
2. Wagner’s test – Wagner’s reagent (Iodine potassium iodide solution) →
Reddish brown precipitate
3. Hager’s test – Hager’s reagent (Picric acid) → Yellow precipitate
4. Dragendorff’s test – Dragendorff’s reagent (Potassium bismuth iodide solution)
→ Reddish brown precipitate
4.1.7 Therapeutic activity or Pharmacological application
Alkaloids are having different types of therapeutic effects: –
• Belladonna (Antispasmodic) – parasympatholytic in action and used to reduce the
secretion of saliva, gastric juice and also sweat.
• Rauwolfia (Anti-hypertensive) – The main constituent is reserpine which is used
to lower high blood pressure.
• Ergot (Oxytocic) – Have oxytocic effect due to the presence of ergotamine.

4.2 GLYCOSIDE
4.2.1 Introduction of Glycoside
Definition: It may be defined as the organic compounds from
plant or animal sources which on enzymatic or acid
hydrolysis give one or more sugar and non-sugar moiety. The
glycone and aglycone portions can be chemically separated
by hydrolysis in the presence of acid.
4.2.2 Glycoside have following general properties:
• The aglycone part is soluble in organic solvents like benzene or ether.
• They are hydrolysed by water, enzymes and mineral acids.
• They are optically active.
• They are crystalline or amorphous substances that are soluble in water or alcohol
and insoluble in organic solvents like benzene and ether.
4.2.3 Isolation of Glycoside
A Soxhlet apparatus is used to extract the finely powdered
plant portion using either water or alcohol. Heating at the right
temperature destroys the enzymes found in plant tissue. For
thermolabile glycosides, greater caution should be used, and
low temperatures should be used for extraction.
Stass-Otto Method:
Powdered drug
↓
Extract below 45°C
(extracted by continuous hot percolation using Soxhlet apparatus with alcohol as
solvent)
↓
Eliminate other compounds
↓
Addition of lead acetate
(to precipitate tannins)
↓
Precipitation of tannins
(non glycosidal impurities also removed)
↓
Separate the non glycosidal impurities
↓
 Pass H₂S gas for the removal of excess lead acetate
↓
Eliminate excess lead sulphide
↓
Crude Glycoside
4.2.4 Classification of Glycosides:
Classification on the basis of Glycosidic bond
1. C-glycosides: In these glycosides, the sugar is linked (condensed) directly to the
Carbon atom of aglycone. They are not hydrolysed by heating with dilute acid or
alkalis but by oxidative hydrolysis with ferric chloride. E.g. Aloe, Cascara,
Cochineal (carminic acid).
Aglycone – CH + OH – C₆H₁₁O₅ → Aglycone – C – C₆H₁₁O₅ + H₂O
2. O-glycosides: In these glycosides, the sugar part is linked with an oxygen atom
of aglycone. E.g. Senna, Rhubarb
Aglycone – OH + OH – C₆H₁₁O₅ → Aglycone – O – C₆H₁₁O₅ + H₂O
3. S-glycosides: In these glycosides, the sugar attached to a Sulphur atom of
aglycone. E.g. Sinigrin from black mustard.
Aglycone – SH + OH – C₆H₁₁O₅ → Aglycone – S – C₆H₁₁O₅ + H₂O
4. N-glycosides: In these glycosides the sugar linked with Nitrogen atom of amino
group of aglycone. E.g. Nucleoside
Aglycone – NH + OH – C₆H₁₁O₅ → Aglycone – N – C₆H₁₁O₅ + H₂O
Classification on the basis of Aglycone part
1. Anthraquinone glycosides – Senna, Aloe, Cascara, Rhubarb, Hypericum
2. Cardiac glycosides – Digitalis, Strophanthus, Ouabain, Thevetia, Squill
 3. Saponin glycosides – Dioscorea, Shatavari, Brahmi, Ginseng, Liquorice,
Senega, Sarsaparilla, Gokhru, Quillaia bark, Jal Brahmi, Momordica, Safed
musali
4. Cyanogenetic glycosides – Bitter almond, Wild cherry bark
5. Isothiocyanate glycosides – Black mustard
6. Flavanol glycosides – Buckwheat, Ginkgo, Silymarin
7. Coumarin glycosides – Ammi, Visnaga, Psoralea, Tonka bean, Mylabris
8. Aldehyde glycosides – Vanilla
9. Phenol glycosides – Bear berry
10. Steroidal glycoalkaloids – Solanum
11. Bitter glycosides – Gentian, Picrorhiza, Chirata, Quassia, Gymnema, Henna
4.2.5 Occurrence and distribution of Glycoside
Dicot plants of families like Leguminosae, Liliaceae, Rhamnaceae, Polygonaceae,
Rubiaceae, Scrophulariaceae. Fungi, lichens, and insects, where it serves as a basic
skeleton for their pigments. Lower plants bryophytes, pterodophytes and
gymnosperms are devoid of such glycosides.
4.2.6 Identification tests
Test for Anthraquinone Glycosides
1. Borntrager’s test:

2. Modified Borntrager’s test: specific for C-type of anthraquinone glycosides.

Test for Saponin Glycosides
1. Haemolysis test: A drop blood on slide + Saponin solution → RBC’s becomes
ruptured
2. Foam test: Drug + 10–20 ml of water, shakes → Formation of froth
4.2.7 Therapeutic activity or Pharmacological application
Glycosides find to possess a variety of therapeutic uses. The following are some
important uses: –
• Senna – Senna leaves are used as laxative. It causes irritation of large intestine and
have some griping effect.
• Aloe – The drug Aloes is one of the safest and stimulating purgatives.
• Rhubarb – The roots contain anthraquinones, which have a purgative effect, and
also tannins and bitters, which have an opposite astringent effect.
• Digitalis – It has a profound tonic effect upon a diseased heart, enabling the heart
to beat more slowly, powerfully and regularly without requiring more oxygen.
• Thevetia – Seeds are used in the treatment of rheumatism, dropsy and also used as
abortifacient and purgative.
• Squill – It is largely used for its stimulating, expectorant and diuretic properties,
and is also a cardiac tonic.
• Brahmi – The plant is used as tonic, in diseases of skin, nerves, blood and also to
improve memory.
• Vanilla – Vanilla pods are widely used in confectionery and in perfumery.
• Glycyrrhiza – Glycyrrhiza is widely used as a sweetening agent.
• Gokhru – It has cooling, anti-inflammatory, antiarthritic, diuretic, tonic,
aphrodisiac properties.
 4.3 TERPENOIDS
4.3.1 Introduction of Terpenoids
Definition: A large class of organic compounds including
terpenes, diterpenes, and sesquiterpenes. They have
unsaturated molecules composed of linked isoprene units,
generally having the formula (C₅H₈).
4.3.2 General properties of Terpenoids: –
• Terpenoids occurs only in volatile oils.
• They are normally colorless liquid or solids with pleasant smell.
• They are insoluble in water and soluble in alcohol, organic solvents and fixed oils.
• Most of the terpenoids are optically active and they get oxidized by oxidizing
agents.
4.3.3 Classification of Terpenoids: –
DRUGS
FORMULA NAME OF CRUDE DRUG
CONTAINING
Fennel, Palmarosa, Citronella, Chenopodium,
Eucalyptus oil, Lemon grass oil, Peppermint oil,
Monoterpenoids C₁₀H₁₆ Caraway, Anise, Cummin, Cardamom, Dill, Lemon
peel, Orange peel, Nutmeg, Cinnamon, Tulsi, Musk
Sesquiterpenoids C₁₅H₂₄ Artemisia, Sandal wood oil, Clove
Diterpenoids C₂₀H₃₂ Taxus, Coleus
Triterpenoids C₃₀H₄₈ Ambergris
Tetraterpenoids C₄₀H₆₄ Annatto, Saffron
4.3.4 Therapeutic effects of Terpenoids: –
Terpenoids are present in all types of volatile oils so the therapeutic effects possess
by the terpenoids similar as the volatile oils. Terpenoids are used in cosmetics,
perfumes, soaps, and in foods also.

4.4 VOLATILE OILS

4.4.1 Introduction of Volatile oil:
Definition: The term "volatile oils" refers to the pungent
components found in both plant and animal sources. They are also
referred to as "Ethereal oils" since they evaporate when exposed
to air at room temperature. They are also referred to as "Essential
oils".
4.4.2 General properties of Volatile oil: –
• Lighter, less viscous, optically active with a specific optical rotation value.
• High refractive index.
• They do not leave stains as opposed to fixed oils.
• Partially soluble in H₂O and soluble in organic solvent like ether, CHCl₃, ethanol
etc.
• The odour and taste of the oils is due to the oxygenated terpenoids.
4.4.3 Isolation of Volatile oil: –
Volatile oils are extracted by steam-distillation, solvent extraction or mechanical
means such as Ecuelle and Effleurage techniques.
➢ Hydro-distillation method (for leaf drugs) – The fresh material is subjected to
hydro-distillation use for the leaf drugs.
➢ Effleurage method (for fresh flower petals) is used for extraction of delicate
perfumes. The fresh flower petals are spread over the layer of fatty material,
allowing for imbibing.
➢ Ecuelle method (for citrus oils) is used for extraction of citrus oils, wherein oil
cells in rind are ruptured mechanically.
➢ Liquid carbon dioxide – Liquefied under pressure, it acts as a solvent reserving
back to gaseous nature when pressure is reduced leaving no residue of solvent.
4.4.4 Classification of Volatile oil: –
• Aldehyde volatile oils – Bitter almond, Orange peel, Cinnamon, Lemon grass,
Citronella oil, Lemon peel.
• Alcohol volatile oils – Coriander, Peppermint, Sandalwood, Cardamom
• Hydrocarbon volatile oils – Black pepper, Turpentine
• Ketone volatile oils – Buchu, Caraway, Camphor, Dill, Musk, Spearmint, Civet
oil
• Phenolic ether volatile oils – Anise, Calamus, Fennel, Nutmeg
• Oxide volatile oils – Chenopodium, Eucalyptus
• Ester volatile oils – Lavender, Valerian, Gaultheria
• Phenol volatile oil – Clove, Thyme
4.4.5 Occurrence of Volatile oil: –
Volatile oils are present in entire plants or almost in any part of the plant as
• Leaf – Eucalyptus
• Bark – Cinnamon
• Seed – Cardamom
• Fruit – Fennel, Coriander
4.4.6 Identification tests: –
1. To the thin section of the drug, add an alcoholic solution of Sudan III.
Red colour obtained by globules indicates the presence of volatile oil.
2. To the thin section of the drug, add a drop of tincture alkane.
Red colour indicates the presence of volatile oil.
4.4.7 Therapeutic effects of Volatile oil: –
Therapeutically volatile oils are used as
• Fennel – Fennel is used as a stomachic, aromatic, diuretic, carminative,
diaphoretic, as a digestive, pectoral, and flavouring agent.
• Coriander – Aromatic, carminative, stimulant, alterative, antispasmodic,
diaphoretic and flavouring agent.
• Chenopodium oil – Chenopodium oil is used as an anthelmintic especially in
tapeworm, round worms, and hook worms.
• Eucalyptus oil – It is also used in the treatment of lung diseases, sore
• Clove – Clove is used as a dental analgesic, carminative, stimulant, flavouring
agent, an aromatic.
It is utilized in pharmaceutical formulations as a flavoring and fragrance component
to cover up the disagreeable smell of the medications.

4.5 TANNINS
4.5.1 Introduction of Tannins
Definition: Tannins are complex organic, polyphenolic, non
nitrogenous plant products, which generally have astringent
properties, used in tanning of animal skins or precipitation of
proteins.
4.5.2 Isolation of Tannins
Isolation of myrobalan:
Fully matured and well dried fruits are selected.
↓
Seed-free fruits are powdered and dried once again.
↓
Dried powdered is subjected to the treatment of four times of its weight of ethyl
alcohol on a shaker for 4 to 6 hours.
 ↓
Extract is filtered and kept aside for one hour
↓
Drug is re-extracted with alcohol
↓
Both the extracts are mixed together. The extract is vacuum concentrated to a
semisolid mass.
↓
Semisolid mass is diluted with distilled water in the proportion of 1:40, preserve it
over-night at 5°C
↓
Filter the extract and reject the flocculated precipitate
↓
Clean filtrate is extracted three times with equal quantity of ethyl acetate
↓
Concentrate the combined ethyl acetate extracts in vacuum
Tannic acid obtained
4.5.3 Classification of Tannins: –
1. Hydrolysable tannins – On treatment with acid or enzyme it produces gallic acid
and ellagic acid. When these tannins are heated pyrogallol is produced.
E.g. Nutgall, Oak, Myrobalan, Pomegranate bark.
2. Condensed tannins or non-hydrolysable – Also known as phlobatannin. Resistant
to hydrolysis. On treatment with acid, it produces Phlobaphene. Related to
flavonoids pigments.
E.g. Ashoka Bark, Black catechu, Pale catechu, Pterocarpus, Cinchona bark,
Cinnamon bark.
3. Pseudo tannins – They are low molecular weight phenolic compounds. They do
not obey to goldbeater’s skin test.
E.g. Catechin, Tea, Cocoa – Chlorogenic acid, Nuxvomica, Coffee.
4.5.4 Occurrence of Tannins: –
Several different chemical groups that are commonly present in the plant world
make up the category of chemicals known as tannins. Families of plants that are
particularly high in both hydrolysable and non-hydrolysable groups of tannins
include the Rosaceae, Leguminosae, Combretaceae, and Polygonaceae among
others.
Tannins are usually localized in specific parts of the plants like
• Leaves – Pale catechu
• Steam – Ashoka
• Fruits – Amla, Bahera
• Bark – Arjuna bark etc.
4.5.5 Identification test: –
1. Goldbeater’s Skin Test:
A piece of goldbeaters skin soaked in 2% hydrochloric acid + washed
↓
Placed in a solution of tannin for 5 minutes
↓
Transferred to 1% ferrous sulphate solution
↓
The skin acquires brown or black colour
2. Match Stick Test (Catechin test):
Dip a matchstick in the dilute extract of the drug
↓
dry + moisten it with conc. HCl
↓
warm it near a flame
↓
Wood turns purple due to formation of Phloroglucinol
3. Ferric Chloride Test:

4. Phenazone Test:

5. Gelatin Test:

4.5.6 Therapeutic activity or pharmacological applications: –

A variety of therapeutic effects of tannins includes:
• Bahera – Bahera is used as an astringent and in the treatment of dyspepsia and
diarrhoea. It is a constituent of Triphala.
• Myrobalan – Because of antiseptic and healing properties of tannins, it is used
externally in chronic ulcers, wounds, piles, and as a stomachic.
• Arjuna bark – It causes decrease in blood pressure and heart rate.
• Amla – It has antioxidant, antibacterial, antifungal, and antiviral activities.
• Ashoka bark – It stimulates the uterus by the prolonged and frequent uterine
contractions.
• Nutgalls – It is used medicinally as a local astringent in ointments and
suppositories.
• Pale catechu – In diarrhoea, it is used as general astringent.
• Black catechu – Cutch is used in medicine as astringent. It cures troubles of
mouth, diseases of the throat and diarrhoea.
In medicine, tannins have astringent characteristics that hasten wound healing and
the growth of new tissue.
Different ulcers, hemorrhoids, mild burns, frostbite, etc. are treated with tannins.
4.6 RESINS
4.6.1 Introduction of resin
Definition: Resins are amorphous products of a complex
chemical nature. These are mixtures of essential oils,
oxygenated products of terpene and carboxylic acids found
as exudations from the trunk of various trees. They are
transparent or translucent solids, semi-solids or liquid
substances containing large number of carbon atoms.
4.6.2 Isolation of resins:
Pharmaceutical resins are obtained from the plants and animals by any of these
methods:
• By extraction with alcohol and precipitation with water – Jalap, Podophyllum,
Ipomoea
• By distillation for separation of oil – Copaiba, Colophony
• By heating the plant part – Guaiacum
• As plant exudates by incisions – Myrrh, Asafoetida, Balsams
• By processing the encrustations – Shellac
4.6.3 Classification of Resins:
Depending upon the type of the constituents of the resin, they are further classified
as:
(a) Acid resin –
This type of resins consists acids. E.g. Colophony (abietic acid), Copaiba (copaivic
and oxycopaivic acids), Myrrh (commiphoric acid), Shellac (allerutic acid).
(b) Ester resin –
This type of resin consist ester. E.g. Benzoin (coniferyl benzoate) and storax
(cinnamyl cinnamate).
(c) Resin alcohols –
The contents are the complex alcohols of high molecular weight. They are either
found in free state or as esters. E.g. balsam of peru (peruresinol), Gurjan balsam
(gurjuresinol) and Guaiacum resin (guaic-resinol).
(d) Resin combination –
• Oleo-resin: Resin in homogenous mixture with volatile oils. E.g. Capsicum,
Turmeric, Ginger, Copaiba
• Gum resin: Resin in homogenous mixture with gum. E.g. Ammoniacum
• Oleogum resin: Resin in homogenous mixture with gum and volatile oil. E.g.
Myrrh, Asafoetida, Gamboge
• Balsam resin: Resin in combination with aromatic acid like cinnamic and benzoic
acid. E.g. Tolu balsam, Peru balsam, Storax, benzoin.
• Glycoresins: Resin in combination with sugars by glycosylation. E.g. Jalap,
Ipomoea, Podophyllum.
4.6.4 Occurrence and distribution of resins:
The glands or cavities of the plants called schizogenous or schizolysigenous are
where resin is made and stored. At each distinct place, glands are present. For
example, Blood root resin cells, guaiacum heartwood components, Indian hamp
external glands, male fern internal glands, or the gland on the surface of the lac bug
are just a few examples of where this resin can be found.
4.6.5 Therapeutic activity and pharmacological applications:
The pharmaceutical applications of resins are: –
• Asafoetida – Asafoetida is used as carminative, expectorant, antispasmodic, and
laxative.
• Peru Balsam – Peru Balsam is used as scabicide and parasiticide, in skin catarrh,
diarrhoea, ulcer therapy, as a local protectant.
• Tolu Balsam – Balsam of Tolu is used as an expectorant, stimulant, and antiseptic.
• Capsicum – Capsicum has been used externally as stimulant, counter irritant, and
rubefacient.
• Jalap – Jalap can stimulate the intestinal secretion, it act as a laxative.
• Ipomoea – Ipomoea resin is strong cathartic.
• Podophyllum – Podophyllum resin or podophyllin shows cytotoxic activity.
• Cannabis – Cannabis resin is tonic, sedative, analgesic, intoxicant, stomachic,
antispasmodic, antianxiety, anticonvulsant, antitussive, and narcotic.
• Myrrh – Myrrh is used as carminative and in incense and perfumes.
• Ginger – It is prescribed in dyspepsia, flatulent colic and vomiting spasms.
• Colophony – Colophony is used as stiffening agent in ointments, adhesives,
plasters and cerates and as a diuretic in veterinary medicine.