Pharmacognosy I College of Pharmacy
2nd Year 2nd Semester Al Noor University
Lec.7
Chemistry of natural drug products
Assist. Lect. Sara Kutaiba
BSc Pharmacy
MSc Pharmacognosy and Medicinal Plants
Chemistry of Natural Drug Products
Natural drug products, primarily derived from plants, owe their therapeutic properties to a
diverse array of secondary metabolites. These compounds can be categorized into several
major classes:
1) Alkaloids
2) Glycosides
3) Terpenoids and Steroids
4) Phenolics
5) Resins and Oleoresins
6) Essential Oils (Volatile Oils)
7) Carbohydrates and Polysaccharides (Primary metabolites included due to their therapeutic
and pharmaceutical importance).
Alkaloids
Alkaloids are nitrogen-containing organic compounds that are mostly derived from plant sources.
They are typically basic (alkaline) in nature and exhibit strong physiological activity, often on the
nervous system.
General Characteristics:
1) Contain at least one nitrogen atom, usually in a heterocyclic ring.
2) Most are alkaline in reaction, hence the name "alkaloid".
3) In plants, alkaloids are typically found in the form of salts combined with organic acids, such as
oxalic or citric acid. This enhances their water solubility and stability, making it easier for the
plant to store and regulate these biologically active substances.
4) Typically bitter in taste and crystalline solids.
5) Usually found in specific plant families such as:
a) Solanaceae (e.g., atropine)
b) Papaveraceae (e.g., morphine)
c) Rubiaceae (e.g., quinine)
Classification of Alkaloids:
1) True Alkaloids
a) Derived from amino acids
b) Contain nitrogen in a heterocyclic ring.
c) Examples:
Morphine (from Papaver somniferum)
Quinine (from Cinchona)
Atropine (from Atropa belladonna)
2) Protoalkaloids
a) Derived from amino acids.
b) Nitrogen is not in a ring.
c) Examples:
Ephedrine (from Ephedra sinica)
Mescaline (from Lophophora williamsii)
3) Pseudoalkaloids
a) Not derived from amino acids.
b) Nitrogen introduced late in biosynthesis.
c) Examples:
Caffeine and Theobromine (from Camellia sinensis and Theobroma cacao)
Pharmacological Actions:
1) CNS stimulants: e.g., caffeine.
2) CNS depressants: e.g., morphine.
3) Antimalarial: e.g., quinine.
4) Anticholinergic: e.g., atropine.
5) Sympathomimetic: e.g., ephedrine.
Glycosides
Glycosides are an organic compounds, usually of plant origin, that composed of a sugar
molecule (such as glucose, fructose, ribose, etc.) and non-sugar molecule bonded via a
glyosidic bond.
Glycosides are composed of two portions:
1) Glycone portion that refer to the sugar part of the glycoside, the sugar component of
glycosides may be mono, di, tri or tetra saccharides.
2) Aglycone (Genin) portion that refer to the non-sugar part of glycoside which is mainly
lipophilic molecule.
Inside the body the glycosides will be cleaved to glycone and aglycone parts,
the glycone part confers on the molecule solubility properties, thus is
important in the absorption and distribution in the body, while the aglycone
part is responsible for the pharmacological activity.
Properties of Glycosides
Water-soluble due to the sugar portion.
Hydrolysable: can be broken down into sugar and aglycone by enzymes (glycosidases) or acids.
Found mainly in vacuoles of plant cells.
They are inactive in the plant until hydrolyzed, which activates the aglycone.
Classification Based on Aglycone Nature
1) Phenolic glycosides
Aglycone is phenol.
e.g., Arbutin (Bearberry) → urinary antiseptic.
2) Anthraquinone glycosides
Aglycone is anthraquinone.
e.g., Sennosides (Senna, Rhubarb) → laxatives.
3) Cardiac glycosides
Aglycone is steroidal structure.
e.g., Digoxin (Digitalis lanata) → used for heart failure.
4) Flavonoid glycosides
Aglycone is flavonoid compound.
e.g., Rutin (Buckwheat), Quercetin derivatives → antioxidant.
5) Saponin glycosides
Aglycone is steroid or triterpenoid.
Soap-like foam in water, used as expectorants.
6) Cyanogenic glycosides
Compounds that are chemically bound to sugars and release cyanide in the form of
hydrogen cyanide (HCN) (known as prussic acid) under certain conditions.
e.g., Amygdalin (Bitter almonds, Apricot kernels).
7) Isothiocyanate glycosides (Glucosinolates)
Isothiocyanate glycosides, commonly referred to as glucosinolates, are sulfur-
containing glycosides that yield isothiocyanates (mustard oils) upon enzymatic
hydrolysis (Myrosinase).
These compounds are responsible for the pungent taste and smell of mustard,
horseradish, and other cruciferous vegetables.
Terpenoids and Steroids
These two major classes of natural products are structurally related and biologically
important.
Both are biosynthesized from isoprene units and found in a wide variety of medicinal
plants.
Terpenoids (Isoprenoids)
Terpenoids are a large class of naturally occurring organic compounds derived from
isoprene units (C₅H₈).
They are also known as isoprenoids and may be modified by oxidation or rearrangement of
the carbon skeleton.
General formula: (C₅H₈)ₙ, where n indicates the number of isoprene units.
Pharmacological Importance:
Antimicrobial and decongestant: Volatile oils (essential oils) like Menthol, camphor and
cineole.
Antimalarial: Artemisinin.
Anti-inflammatory and anticancer: Boswellic acid.
Expectorant and bronchodilator: Terpenoids in eucalyptus, thyme.
Pigments (e.g., carotenoids).
Hormones (e.g., gibberellins in plants).
Steroids
Steroids are a subclass of terpenoids, derived from triterpenes.
They have a core structure of four fused carbon rings: (three 6-membered rings and
one 5-membered ring (cyclopentanoperhydrophenanthrene nucleus).
Examples:
Cholesterol: structural component of cell membranes.
Steroid hormones:
Sex hormones: testosterone, estrogen, progesterone.
Corticosteroids: cortisol, aldosterone.
Bile acids: aid in fat digestion.
Vitamin D: important for calcium metabolism.
Functions:
1) Regulate metabolism, immune response, water balance, reproduction.
2) Structural roles in cell membranes (cholesterol).
Feature Terpenoids Steroids
Derived from Isoprene units Squalene (a triterpenoid)
Structure Various open or cyclic structures Four fused carbon rings
Functions Provide fragrance in essential oils. Act as hormones regulating
Act as pigments (carotenoids) in metabolism and growth.
plants. Important components of cell
Serve as precursors of important membranes (cholesterol).
vitamins (A, E, K).
Examples Menthol, carotenoids, retinol Cholesterol, testosterone,
cortisol
Phenolics
Phenolics are a large group of secondary plant metabolites characterized by the
presence of one or more hydroxyl groups attached directly to an aromatic ring. They
play a major role in plant defense and human health.
Classification of Phenolics:
1) Simple Phenols and Phenolic Acids
Examples: Hydroquinone, Gallic acid, Caffeic acid.
2) Coumarins
Characterized by a benzopyrone structure.
Examples: Coumarin, Umbelliferone, Scopoletin.
3) Tannins
Astringent, water-soluble polyphenols.
Divided into:
1) Hydrolysable tannins (e.g., Gallotannins, Ellagitannins).
2) Condensed tannins (e.g., Proanthocyanidins)
4) Flavonoids
Large group with a common C6-C3-C6 structure.
Subgroups:
1) Flavones (e.g., Apigenin).
2) Flavonols (e.g., Quercetin).
3) Flavanones (e.g., Naringenin).
4) Flavanols (Catechins) (e.g., Epicatechin).
5) Anthocyanidins (e.g., Cyanidin).
6) Isoflavones (e.g., Genistein)
5) Lignans and Lignins
Lignans
Small phenolic compounds formed by the dimerization of two phenylpropanoid units
(C6–C3).
Usually found in seeds, roots, and some medicinal plants.
Often have biological and pharmacological activities.
Example: Podophyllotoxin.
Lignins
Large, complex polymers made of many phenylpropanoid units.
Found in plant cell walls, especially in wood and bark.
Their main role is structural support and rigidity in plants.
6) Stilbenes (C6-C2-C6)
Occurrence: They are mainly found in grapes (especially the skin), berries, peanuts,
and some medicinal plants. The most famous example is resveratrol.
Function: In plants, stilbenes act as defense compounds (phytoalexins) that protect the
plant against fungi, bacteria, and environmental stress.
Benefits for humans: They show antioxidant, anti-inflammatory, cardioprotective, and
potential anticancer effects.
Note (Why they are less common): Stilbenes are considered less common because they
are produced by a limited number of plant species and are often synthesized only in
response to stress or pathogen attack, rather than being constantly present like many
other phenolic compounds.
Properties
1) Antioxidant.
2) Antimicrobial.
3) Anti-inflammatory.
4) Astringent.
5) Pigment (coloring of fruits, flowers).
6) Protective agents against UV radiation and herbivores.
Resins and Oleoresins
Resins are solid or semi-solid, amorphous substances that are usually formed as
plant exudates.
They are insoluble in water, but soluble in alcohol, ether, and oils.
Origin:
Secreted by specialized schizogenous or schizolysigenous glands in plants.
Commonly found in conifers and some dicotyledonous plants.
Characteristics:
Brittle and transparent or translucent.
Usually aromatic and non-volatile.
Chemically composed of resin acids, alcohols, and esters.
Types of Resins:
1) Pure Resins – e.g., Colophony (pine resin).
2) Gum-Resins – e.g., Myrrh (contains gum and resin).
3) Oleo-Resins – e.g., Turpentine (contains oil and resin).
4) Balsams – e.g., Balsam of Peru (resin + benzoic/cinnamic acid).
5) Gum-oleo-resins – e.g., Asafoetida.
Uses:
1) Antiseptic.
2) Stimulant.
3) Expectorant.
4) Ingredients in varnishes and adhesives.
Oleoresins are natural mixtures of oil and resin extracted from plants, especially spices
and medicinal herbs.
They combine the properties of essential oils and resins.
Source:
Found in resin ducts or glands of various plants.
Extracted using solvent extraction or steam distillation.
Characteristics:
Semi-solid or liquid.
Aromatic and flavorful, often used in foods, medicines, and perfumes.
Examples:
Capsicum oleoresin (from chili).
Ginger oleoresin.
Turmeric oleoresin.
Uses:
Flavoring agent.
Anti-inflammatory and analgesic in topical formulations.
Aromatherapy and perfumery.
Active components in pharmaceuticals.
Note: Resins and oleoresins are complex natural mixtures made of many
different substances. Because of this, they do not have a single, well-
defined chemical structure, although the individual compounds within
them may have known structures.
Feature Resins Oleoresins
Nature Solid or semi-solid Semi-solid or liquid
Composition Mainly resin acids Resin + essential oils
Water Solubility Insoluble Insoluble
Uses Varnishes, medicine, Flavoring, medicine,
incense cosmetics
Examples Colophony, Myrrh Capsicum, Ginger,
Turmeric oleoresins
Essential Oils (Volatile Oils)
Volatile oils (also called essential oils) are odorous, volatile constituents of plants that are
evaporated easily when exposed to air at ordinary temperatures.
They are responsible for the fragrance of many plants.
Characteristics:
1) They are liquid at room temperature (though some may solidify in cold).
2) Not greasy like fixed oils, and they evaporate without leaving a stain.
3) Composed mainly of terpenes, terpenoids, and other aromatic compounds.
4) Insoluble in water, but soluble in alcohol, ether, and fixed oils.
Storage:
Volatile oils are sensitive to light, heat, and air, so they must be stored in tightly sealed,
amber-colored bottles to prevent oxidation and loss of aroma.
Extraction Methods:
1) Steam Distillation – most common and traditional method.
2) Expression – mainly for citrus oils (e.g., orange, lemon).
3) Solvent Extraction – used when delicate aromas would be destroyed by heat.
Classification (Based on Chemical Constituents):
1) Hydrocarbons (e.g., limonene, pinene).
2) Alcohols (e.g., menthol, geraniol).
3) Aldehydes (e.g., citronellal).
4) Ketones (e.g., carvone).
5) Phenols (e.g., eugenol).
6) Oxides (e.g., cineole).
7) Esters (e.g., linalyl acetate)
Note: Volatile oils do not have a single, specific structure because they are complex mixtures of
various chemical compounds, primarily derived from plants. The exact composition and structure
of a volatile oil depend on the plant source, the method of extraction, and the specific part of the
plant used (such as flowers, leaves, stems, or roots).
Pharmacological Uses:
1) Antimicrobial.
2) Carminative.
3) Stimulant.
4) Expectorant.
5) Topical analgesic.
Carbohydrates and Polysaccharides
Carbohydrates are organic compounds composed of carbon, hydrogen, and oxygen, typically
with the general formula Cₙ(H₂O)ₙ.
They are classified based on their complexity into:
1) Monosaccharides – the simplest form (e.g., glucose, fructose).
2) Disaccharides – formed by the condensation of two monosaccharides (e.g., sucrose,
lactose).
3) Oligosaccharides – short chains of monosaccharide units.
4) Polysaccharides – high-molecular-weight carbohydrates made up of many monosaccharide
units.
Polysaccharides are divided into:
1) Homoglycans (homopolysaccharides): composed of only one type of monosaccharide (e.g.,
starch, cellulose).
2) Heteroglycans (heteropolysaccharides): composed of more than one type of
monosaccharide (e.g., gum acacia, heparin).
They serve various pharmacognostic purposes:
Starch: a major plant storage carbohydrate, used as a pharmaceutical excipient.
Cellulose: provides structural support in plants and is used as a binder or filler in tablets.
Mucilages and gums: hydrophilic polysaccharides used as demulcents, emulsifying agents,
and stabilizers.
Inulin: a storage polysaccharide in some plants, used for testing renal function and as a
prebiotic.
Polysaccharides also exhibit biological activities, such as immunomodulatory, antioxidant,
and anti-inflammatory effects, making them important in herbal medicines.
Thank you