TERPENES AND

THEIR CLASSES

BY HUMAIRA JAMIL
EH-2109015
 INTRODUCTION:

Plants can manufacture many different types of secondary metabolites," Terpenes

belong to the biggest class of secondary metabolites and basically consist of five
carbon isoprene units.
Terpenes are simple hydrocarbons, while terpenoids are modified class of terpenes
with different functional groups. The terpenoids, sometimes known as isoprenoids, a
huge and diverse class of naturally occurring organic chemicals derived from the 5-
carbon compound isoprene, and the isoprene polymers known as terpenes.
More than 60% to 70% of the chemotherapeutic drugs for cancer and infectious
disease, respectively, are of herbal products.
Many compounds from terpenes are used as flavors, fragrances, and spices, and are
also used in perfumery and cosmetics products and food additives.
Many terpenes have biological activities and are used for medical purposes. For
example, the antimalarial drug Artemisinin and the anticancer drug paclitaxel
(TaxolR) are two of a few terpenes with established medical applications.
 OCCURENCE

Terpenoids are a group of naturally occurring compounds majority of which occur in

plants, a few of them have also been obtained from other sources. Terpenoids are
volatile substances which give plants and flowers their fragrance. They occur widely
in the leaves and fruits of higher plants, conifers, citrus and eucalyptus.
The term ‘terpene’ was given to the compounds isolated from terpentine, a volatile
liquid isolated from pine trees. The simpler mono and sesquiterpene is chief
constituent of the essential oils obtained from sap and tissues of certain plant and
trees. The di and tri terpenoids are not steam volatile. They are obtained from plant
and tree gums and resins. Tertraterpenoids form a separate group of compounds called
‘Carotenoids’.
The term ‘terpene’ was originally employed to describe a mixture of isomeric hydrocarbons
of the molecular formula C 10H16 occurring in the essential oils obtained from sap and tissue
of plants, and trees. But there is a tendency to use more general term ‘terpenoids’ which
include hydrocarbons and their oxygenated derivatives.
The provitamin beta carotene is a terpene derivative referred to as carotenoid. Terpenoids,
such as the carotenoids, contribute to the color of many fruits. They additionally make a
contribution to most of the flavors in our foods, and are important components of many
medicinal recipes.
Monoterpenoids are widely studied for their antiviral property. Terpenoids have ability to
function as anti-cancer and anti-diabetic reagents. They also show interest in biological
activity like insecticidal, antiseptic action, and consequently beneficial in pharmacy.
 The pharmaceutical properties of aromatic plants are partially attributed to essential oils (EO’s),
which can also be visible as an important group of plant secondary metabolites. Although the usage of
EO’s has been ordinarily associated with food flavorings, cosmetics, and perfumes because of their
aroma, the use of volatile monoterpene constituents to cure and prevent human diseases.
 CLASSIFICATION OF TERPENOIDS

Terpenoids No. of isoprene No. of carbon Molecular Examples

units atoms formula

Hemiterpenoids 1 5 C5H8 Isovaleric acid, isoprenol

Monoterpenoids 2 10 C10H16 Linalool, menthol

Sesquiterpenoid 3 15 C5H24 Humulone

Diterpenoids 4 20 C20H32 Retinol

Sesterterpenoids 5 25 C25H40 Manoalide

Triterpenoids 6 30 C30H48 Sterols, squalene

Tetraterpenoids 8 40 Geranial
C40H64 Neral
Carotenoids

Polyterpenoids >8 >40 (C5H8 )n Natural rubber

 CLASSIFICATION

Acyclic Terpenoids: Monocyclic Terpenoids: Bicyclic Terpenoids:

They contain open structure. They contain one ring in the structure. They contain 2 rings in the structure.

Geranial Neral
 ISOPRENE RULE

Thermal decomposition of terpenoids provide isoprene as one of the product. Otto

Wallach mentioned that terpenoids may be constructed up of isoprene unit. Isoprene
rule states that the terpenoid molecules are constituted of two or more isoprene unit.
Further Ingold suggested that isoprene units are joined in the terpenoid via ‘head to
tail’ fashion. Special isoprene rule states that the terpenoid molecule is built of two
or more isoprene units joined in a ‘head to tail’ fashion.
.
 ISOLATION OF MONO AND
SESQUITERPENOIDS

Both mono and sesquiterpenoids have common source i.e., essential oils. Their isolation is
carried out in two steps:
i) Isolation of essential oils from plant parts
ii) Separation of Terpenoids from essential oils.
Isolation of essential oils from plant parts
The plants having essential oils normally have the highest concentration at some particular
time. Therefore, higher yield of essential oil plant material need to be accumulated at this
particular time. E.g. From jasmine at sunset. There
are four methods of extractions of oils.
a) Expression method
b) Steam distillation method
c) Extraction by means of volatile solvents
d) Adsorption in purified fats
 Steam distillation:
Steam distillation is most widely used method. In this method macerated plant
material is steam distilled to get essential oils into the distillate form these are
extracted by using pure organic volatile solvents. If compound decomposes during
steam distillation, it may be extracted with ether at 50 C. After extraction solvent is
removed under reduced pressure.
Separation of Terpenoids from essential oil
A wide variety of terpenoids are found in essential oil obtained from the extraction,
definite physical and chemical methods may be used for the separation of terpenoids.
They are separated with the aid of fractional distillation. The terpenoid hydrocarbons
distill over first followed by the oxygenated derivatives. More recently different
chromatographic techniques have been used both for isolation and separation of
terpenoids.
 GENERAL PROPERTIES OF TERPENOIDS

1. Most of the terpenoids are colorless, aromatic liquids which are lighter than water
and volatile with steam. A few of them are solids e.g. camphor.
2. Most of them are optically active.
3. They undergo polymerization and dehydrogenation.
4. Terpenoids are unsaturated compounds composed of linked isoprene units.
5. They consist of complicated combination of terpenes or sesquiterpenes, alcohols,
aldehydes, ketones, acids and esters.
6. On thermal decomposition, terpenoid gives isoprene as one of the product.
 EXAMPLES OF TERPENOIDS

Lemon grass Lemon Rose

Citral Limonene Geranial

Medicine & flavouring agent Flavouring agent perfumes
Eucalyptus Turpentine tree

cineole pinene
Medicine Paint thinner
 APPLICATIONS

Terpenoids are the important constituents of essential oils that can be used ass flavouring agent.
A. Menthol:
One of the most important flavouring compound and is extensively used in pharmaceuticals,
toothpastes, chewing gum, soaps as well as in ciggerattes.
Menthol is introduced in confectionaries and beverages not only for its minty odour but also as a
cooling and refreshing agent.
B. Carvone:
Carvone is the compound liable for the taste of caraway, dill and spear mint, has been used for
millenia in compound. Carvone is present in two enantiomeric forms:
R (+) carvne smells like a spear mint.
S (-) carvone smells like a caraway.
 C. Linalool
Because of flavorful and aromatic properties, linalool is added to processed food and
beverages, perfumes, cosmetics, and soaps as well as household, detergents and
waxes.
The food and drug administration allows the use of linalool and their esters in baked
goods, candy, beverages and ice-cream.
linalool ha a chiral center at C3 carbon and forms two stereoisomers.
Plant produce both R and S.
(S) Linalool found as a major constituent in essential oil, in coriander seed.