ALCALOIDS AND GLYCOSIDES
Alkaloids are naturally occurring, nitrogen-bearing organic compounds that are basic.
These compounds have a wide range of biological activities and physiological effects on humans
and animals. Plants are the oldest known sources of alkaloids. Glycosides are naturally occurring
substances in which a sugar is bound to another functional group via a glycosidic bond. The
glycosidic bond joining these two components is usually through an oxygen (O), sulfur (S) or a
nitrogen atom (N). The main difference between alkaloid and glycoside is that alkaloids react
with acids forming a salt whereas glycosides show no reaction with acids.
Alkaloids and glycosides are chemical components that can be found in plants.
Alkaloid essentially contains nitrogen atoms, along with carbon and hydrogen. Glycosides may
or may not contain nitrogen. The main difference between alkaloid and glycoside is that
alkaloids react with acids forming a salt whereas glycosides show no reaction with acids.
ALKALOIDS
The medicinal properties of alkaloids are quite diverse. Morphine is a powerful
narcotic used for the relief of pain. Codeine, the methyl ether derivative of morphine found in
the opium poppy, is an excellent analgesic that is relatively nonaddictive. Certain alkaloids act as
cardiac or respiratory stimulants. Quinidine, which is obtained from plants of the genus
Cinchona, is used to treat irregular rhythms of the heartbeat. Many alkaloids affect respiration,
but in a complicated manner such that severe respiratory depression may follow stimulation. The
drug lobeline (from Lobelia inflata) is safer in this respect and is clinically useful. Ergonovine
(from the fungus Claviceps purpurea) and ephedrine (from Ephedra species) act as blood-vessel
constrictors. Ergonovine is used to reduce uterine hemorrhage after childbirth, and ephedrine is
used to relieve the discomfort of common colds, sinusitis, hay fever, and bronchial asthma.
Many alkaloids possess local anesthetic properties, though clinically they are seldom
used for this purpose. Cocaine (from Erythroxylon coca) is a very potent local anesthetic.
Quinine (from Cinchona species) is a powerful antimalarial agent that was formerly the drug of
choice for treating that disease, though it has been largely replaced by less toxic and more
effective synthetic drugs. The alkaloid tubocurarine is used as a muscle relaxant in surgery.
Two alkaloids, vincristine and vinblastine (from Vinca rosea), are widely used as
chemotherapeutic agents in the treatment of many types of cancer.
Nicotine obtained from the tobacco plant (Nicotiana tabacum) is the principal alkaloid
and chief addictive ingredient of the tobacco smoked in cigarettes, cigars, and pipes. Some
alkaloids are illicit drugs and poisons. These include the hallucinogenic drugs mescaline (from
Anhalonium species) and psilocybin (from Psilocybe mexicana). Synthetic derivatives of the
alkaloids morphine and lysergic acid (from C. purpurea) produce heroin and LSD, respectively.
The alkaloid coniine is the active component of the poison hemlock (Conium maculatum).
Strychnine (from Strychnos species) is another powerful poison.
Alcaloids are present in the following parts of the plants:
- The leaves: tobacco (Nicotiana tabacum) or tea (Camellia Sinensis);
- The seeds: caffeine that appears in coffee (Arabian Coffea);
- The roots: phytolaccine from pokeweed (Phytolacca Americana), the poisonous root of
monkshood (Aconitum napellus); atropine mainly appears in the root belladonna (Atropa
Belladonna);
- The fruits: hemlock (Conium maculatum) or berries of deadly nightshade (Atropa
Belladonna).
GLYCOSIDES
Glycoside, any of a wide variety of naturally occurring substances in which a
carbohydrate portion, consisting of one or more sugars or a uronic acid (i.e., a sugar acid), is
combined with a hydroxy compound. The hydroxy compound, usually a non-sugar entity
(aglycon), such as a derivative of phenol or an alcohol, may also be another carbohydrate, as in
cellulose, glycogen, or starch, which consist of many glucose units.
Many glycosides occur in plants, often as flower and fruit pigments; for example,
anthocyanins.
Various medicines, condiments, and dyes from plants occur as glycosides; of great value
are the heart-stimulating glycosides of Digitalis and Strophanthus, members of a group known as
cardiac glycosides. Several antibiotics are glycosides (e.g., streptomycin). Saponins, widely
distributed in plants, are glycosides that lower the surface tension of water; saponin solutions
have been used as cleansing agents.
The richest plant is common soapwort (Saponaria officinalis). Among other saponin-rich
plants there are ivy (Hedera helix), butcher’s broom (Ruscus aculeatus), asparagus (Asparagus
officinalis), sarsaparilla (Smilax aspera) etc.
Glycosides derived from glucuronic acid (the uronic acid of glucose) and steroids are
constituents of normal animal urine. Compounds (nucleosides) derived from the partial
breakdown of nucleic acids are also glycosides.
While there are many plant sources of cardiac glycosides, common ones include the following:
Purple foxglove (Digitalis purpurea);
Woolly foxglove (Digitalis lanata);
Ouabain (Strophanthus gratus);
Lily-of-the-valley (Convallaria majalis);
Common oleander (Nerium oleander).
The cyanogenic glycosides belong to the products of secondary metabolism, to
the natural products of plants. These compounds are composed of an alpha-hydroxynitrile type
aglycone and of a sugar moiety (mostly D-glucose). The distribution of the cyanogenic
glycosides (CGs) in the plant kingdom is relatively wide, the number of CG-containing taxa is at
least 2500, and a lot of such taxa belong to families Fabaceae, Rosaceae, Linaceae, Compositae
and others.
