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Terpenes and Terpenoids: Principles of Biochemistry BIOC-301 Dr. Gull-E-Faran

This document discusses different classes of terpenes and terpenoids. It explains that terpenes are simple hydrocarbons made of repeating five-carbon isoprene units, while terpenoids contain additional functional groups. The classes are defined based on the number of isoprene units and include monoterpenes, sesquiterpenes, diterpenes, sesterpenes, triterpenes, and meroterpenes. Many terpenoids have biological activities such as antimicrobial, anti-inflammatory, and anticancer properties.

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146 views10 pages

Terpenes and Terpenoids: Principles of Biochemistry BIOC-301 Dr. Gull-E-Faran

This document discusses different classes of terpenes and terpenoids. It explains that terpenes are simple hydrocarbons made of repeating five-carbon isoprene units, while terpenoids contain additional functional groups. The classes are defined based on the number of isoprene units and include monoterpenes, sesquiterpenes, diterpenes, sesterpenes, triterpenes, and meroterpenes. Many terpenoids have biological activities such as antimicrobial, anti-inflammatory, and anticancer properties.

Uploaded by

Fahad Naeem
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Terpenes and Terpenoids

PRINCIPLES OF BIOCHEMISTRY
BIOC-301
DR. GULL-E-FARAN
TERPENES
• Natural products are the compounds which are isolated from different
natural sources such as;
plants, animals, microbes, insects, plant pathogens, and endophytes
and marine.
These all are known as secondary metabolites since they are formed
due to the enzymatic resections of primary metabolites (amino acids,
sugars, vitamins, etc.).
Terpenes belong to the biggest class of secondary metabolites and
basically consist of five carbon isoprene units which are assembled to
each other (many isoprene units) by thousands of ways.
TERPENOIDS
• Terpenes are simple hydrocarbons, while terpenoids are modified
class of terpenes with different functional groups and oxidized methyl
group moved or removed at various positions.
• Terpenoids are divided into 1-monoterpenes 2-sesquiterpenes,
3diterpenes, 4- sesterpenes, and 5- triterpenes depending on its
carbon units. Most of the terpenoids with the variation in their
structures are biologically active and are used worldwide for the
treatment of many diseases.
• Many terpenoids inhibit different human cancer cells and are used as
anticancer drugs such as Taxol and its derivatives.
• Many flavorings and nice fragrances contain terpenes because of its
nice aroma. Terpenes and its derivatives are used as antimalarial
drugs such as artemisinin and related compounds. Meanwhile,
terpenoids play a diverse role in the field of foods, drugs, cosmetics,
hormones, vitamins, and so on. This chapter provides introduction
and information on the bioactive terpenes isolated currently from
different natural sources.
1. Monoterpenes
• Monoterpenes consist of 10 carbon atoms with two isoprene units and
molecular formula C10H16. These are naturally present in the essential and fixed
oils of plants and related sources.
• Monoterpenes are structurally divided into the acyclic, monocyclic, and bicyclic
type of compound. The compounds belong to this class usually have strong
aroma and odor and are used in many pharmaceutical companies.
• Mixture of different monoterpene-based oils is used as fragrances for making
perfumes and in other cosmetics. Most of the monoterpenes are active
biologically with strong antibacterial activities. Several studies have shown in
vitro and in vivo antitumor activity of many essential oils obtained from plants.
• The antitumor activity of essential oils of many species has been related to the
presence of monoterpenes in their composition.
2. Sesquiterpenes

• Sesquiterpenes are the class of secondary metabolites consisting of


three isoprene units (C15H24) and found in linear, cyclic, bicyclic, and
tricyclic forms.
• Sesquiterpenes are also found in the form of lactone ring. Many of
the latex in latex-producing plants contain sesquiterpene and these
are potent antimicrobial and anti-insecticidal agent.
• Artemisinin, a sesquiterpene lactone, one of the most active
compounds in Artemisia annua shoots and roots
3. Diterpenes

• Diterpenoids belong to a versatile class of chemical constituents


found in different natural sources having C20H32 molecular formula
and four isoprene units.
• This class of compounds showed significant biological activities
including anti-inflammatory, antimicrobial, anticancer, and antifungal
activities. Some of the diterpenes also have cardiovascular activity,
such as grayanotoxin, forskolin, eleganolone, marrubenol, and 14-
deoxyandrographolide.
• Kaurane and pimarane-type diterpenes are also biologically active
metabolites isolated from the roots and leaves of different plants
4. Sesterpenes

• Sesterpenes consist of 25 carbon atoms with 5 isoprene units and


molecular formula C25H40. These are naturally present in the fungus,
marine organism, insects, sponges, lichens, and protective waxes of
insects.
• These types of compounds are biologically active having anti-
inflammatory, anticancer, antimicrobial, and antifungal activities
5. Triterpenes

• A major class of secondary metabolites are known as triterpenes and


it usually contains 30 carbon atoms consisting of 6 isoprene units. It is
derived from the squalene biosynthetic pathway.
• Triterpenes have many methyl groups and it can be oxidized into
alcohols, aldehydes, and carboxylic acids, which make it complex and
differentiate it biologically.
• Triterpenes have many active sites for the glycosylation which
converts it into another big class of compounds, namely, saponins
(triterpene glycoside). Herein, we are discussing some recently
published bioactive triterpenes
6. Meroterpenes

• Meroterpenes are the secondary metabolites with partial terpenoid


skeleton. Meroterpenoids were partially derived from mevalonic acid
pathways and widely derived from animals, plants, bacteria, and
fungi.
• Meroterpene biosynthesis expands the diversity available to
isoprenoid pathways alone and allows for the assembly of natural
products with highly unique structural attributes.
• Organisms belonging to the fungal kingdom have become proficient at
exploiting this broad chemical synthesis platform for complex
metabolite production.

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