Alkaloids

Introduction

Alkaloid, any of a class of naturally occurring organic nitrogen-containing bases.

Alkaloids have diverse and important physiological effects on humans and other
animals. Well-known alkaloids include morphine, strychnine, quinine, ephedrine,
and nicotine. Alkaloids are found primarily in plants and are especially common in
certain families of flowering plants. In fact, as many as one-quarter of higher plants are
estimated to contain alkaloids, of which several thousand different types have been
identified. In general, a given species contains only a few kinds of alkaloids, though both
the opium poppy (Papaver somniferum) and the ergot fungus (Claviceps) each contain
about 30 different types. Certain plant families are particularly rich in alkaloids; all
plants of the poppy family (Papaveraceae) are thought to contain them, for example. The
Ranunculaceae (buttercups), Solanaceae (nightshades), and Amaryllidaceae (amaryllis)
are other prominent alkaloid-containing families. A few alkaloids have been found
in animal species, such as the New World beaver (Castor canadensis) and poison-dart
frogs (Phyllobates). Ergot and a few other fungi also produce them.

The function of alkaloids in plants is not yet understood. It has been suggested that they
are simply waste products of plants’ metabolic processes, but evidence suggests that
they may serve specific biological functions. In some plants, the concentration of
alkaloids increases just prior to seed formation and then drops off when the seed is ripe,
suggesting that alkaloids may play a role in this process. Alkaloids may also protect
some plants from destruction by certain insect species.

The chemical structures of alkaloids are extremely variable. Generally, an alkaloid

contains at least one nitrogen atom in an amine-type structure—i.e., one derived
from ammonia by replacing hydrogen atoms with hydrogen-carbon groups
called hydrocarbons. This or another nitrogen atom can be active as a base in acid-base
reactions. The name alkaloid (“alkali-like”) was originally applied to the substances
because, like the inorganic alkalis, they react with acids to form salts. Most alkaloids
have one or more of their nitrogen atoms as part of a ring of atoms, frequently called a
cyclic system. Alkaloid names generally end in the suffix -ine, a reference to their
chemical classification as amines. In their pure form most alkaloids are colourless,
nonvolatile, crystalline solids. They also tend to have a bitter taste.

Interest in the alkaloids stems from the wide variety of physiological effects (both
wanted and unwanted) they produce in humans and other animals. Their use dates back
to ancient civilizations, but scientific study of the chemicals had to await the growth of
organic chemistry, for not until simple organic bases were understood could the intricate
structure of the alkaloids be unraveled. The first alkaloid to be isolated and crystallized
was the potent active constituent of the opium poppy, morphine, in about 1804.
Functions of Alkaloids

Although their biogenesis and metabolism have been studied in many cases, function of
alkaloids is still vague and not really understood by the chemist. There are some
proposed roles of alkaloids in plant metabolism, plant catabolism or plant physiology as
listed below:-

 As end product of the metabolism or waste products

 As storage reservoir of nitrogen for protein synthesis
 As protective agent for the plants against attack by predators (parasites or
herbivore)
 As plants stimulants and regulators in activities such as growth, metabolism and
reproduction.
 As a detoxification agent, which renders harmless certain substances,
accumulation of which might cause damage to the plant.

Alkaloid Classification

Alkaloids are often divided into the following major groups:

1-True alkaloids: contain nitrogen in the heterocycle and originate from amino acids.

Their characteristic examples are atropine, nicotine, and morphine. This group also
includes some alkaloids that besides the nitrogen heterocycle
contain terpene (e.g., evonine) or peptide fragments (e.g. ergotamine). The piperidine
alkaloids coniine and coniceine may be regarded as true alkaloids (rather than
pseudoalkaloids: see below) although they do not originate from amino acids.

2-Protoalkaloids: which contain nitrogen (but not the nitrogen heterocycle) and also

originate from amino acids. Examples include mescaline, adrenaline and ephedrine.

3-Polyamine alkaloids: derivatives of putrescine, spermidine, and spermine.

4-Peptide and cyclopeptide alkaloids.

5-Pseudoalkaloids: alkaloid-like compounds that do not originate from amino
acids. This group includes terpene-like and steroid-like alkaloids, as well as purine-like
alkaloids such as caffeine, theobromine, theacrine and theophylline. Some authors
classify as pseudoalkaloids such compounds such as ephedrine and cathinone. Those
originate from the amino acid phenylalanine, but acquire their nitrogen atom not from
the amino acid but through transamination.

Distribution of alkaloids in nature

Alkaloids are generated by various living organisms, especially by higher plants – about

10 to 25% of those contain alkaloids. Therefore, in the past the term "alkaloid" was
associated with plants.The alkaloids content in plants is usually within a few percent and
is inhomogeneous over the plant tissues. Depending on the type of plants, the maximum
concentration is observed in the leaves (black henbane), fruits or seeds (Strychnine tree),
root (Rauvolfia serpentina) or bark (cinchona). Furthermore, different tissues of the
same plants may contain different alkaloids.

Beside plants, alkaloids are found in certain types of fungi, such as psilocybin in the
fungus of the genus Psilocybe, and in animals, such as bufotenin in the skin of some
toads  and a number of insects, markedly ants. Many marine organisms also contain
alkaloids. Some amines, such as adrenaline and serotonin, which play an important role
in higher animals, are similar to alkaloids in their structure and biosynthesis and are
sometimes called alkaloids.

Biological role of alkaloids

The role of alkaloids for living organisms that produce them is still unclear. It was
initially assumed that the alkaloids are the final products of nitrogen metabolism in
plants, as urea in mammals. It was later shown that alkaloid concentrations varies over
time, and this hypothesis was refuted. Most of the known functions of alkaloids are
related to protection. However, some animals are adapted to alkaloids and even use them
in their own metabolism. Such alkaloid-related substances as serotonin, dopamine and
histamine are important neurotransmitters in animals. Alkaloids are also known to
regulate plant growth. Another example of an organism that uses alkaloids for protection
is the Utetheisa ornatrix, more commonly known as the ornate moth. Pyrrolizidine
alkaloids render these larvae and adult moths unpalatable to many of their natural
enemies like coccinelid beetles, green lacewings, insectivorous hemiptera and
insectivorous bats.

Applications of alkaloids in medicine

Medical use of alkaloid-containing plants has a long history, and, thus, when the first
alkaloids were isolated in the 19th century, they immediately found application in
clinical practice. Many alkaloids are still used in medicine, usually in the form of salts,
including the following:

Alkaloid Action
Ajmaline antiarrhythmic
Atropine, scopolamine, hyoscyamine anticholinergic
Caffeine stimulant, adenosine receptor antagonist
Codeine cough medicine, analgesic
Colchicine remedy for gout
Emetine antiprotozoal agent
Ergot alkaloids sympathomimetic, vasodilator,
antihypertensive
Morphine analgesic
Nicotine stimulant, nicotinic acetylcholine receptor
agonist
Physostigmine inhibitor of acetylcholinesterase
Quinidine antiarrhythmic
Quinine antipyretics, antimalarial
Reserpine antihypertensive
Tubocurarine muscle relaxant
Vinblastine vincristine antitumor
Vincamine vasodilating, antihypertensive
Yohimbine stimulant, aphrodisiac
Many synthetic and semisynthetic drugs are structural modifications of the alkaloids,
which were designed to enhance or change the primary effect of the drug and reduce
unwanted side-effects. For example, naloxone, an opioid receptor antagonist, is a
derivative of the baine that is present in opium.

Conclusion

Alkaloids are very important compounds for human beings. For ages their extracts were
used as a cure to rescue people from pain like morphine and some illnesses like quinine
in malaria and colchicine in gout. Thanks to alkaloids during ages, people can cure the
diseases and improve their life. Alkaloids showed quite diverse medicinal properties.
Many of them possess local anesthetic properties, but their practical use is limited for
clinical purpose. 

References

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