This document discusses isoprenoids, which are organic compounds composed of two or more units of hydrocarbons with each unit consisting of five carbon atoms arranged in a specific pattern. Isoprenoids are found naturally in plants and animals and have a variety of functions including pigments, vitamins, hormones, and commercial products. They are classified based on the number of isoprene units, with monoterpenes containing two units and polyterpenes containing many units. Isoprenoids are synthesized via both the mevalonate and non-mevalonate pathways, which produce the universal building block isopentenyl diphosphate. Key isoprenoids and their uses are discussed, along with

1. ISOPRENOIDES
By
KAUSHAL KUMAR SAHU
Assistant Professor (Ad Hoc)
Department of Biotechnology
Govt. Digvijay Autonomous P. G. College
Raj-Nandgaon ( C. G. )

2. CONTENTS
INTRODUCTION
DEFFINATION
TERPENE- GENERAL INFORMATION
CHEMICAL COMPOUND
ISOPENOID OF PLANT AND ANIMAL
•NATURAL CCURANCE
•INDUSTRIAL PRODUCTS
NATUR OF ISOPRINOIDS
•NATURAL PRODUCTS
•SECONDARY METABOLITES
•BRANCHED CHAIN ALCOHOL
STRUCTURAL CLASSIFICATION OF ISOPRENOIDS
•HAID TO TAIL
•TAIL TO TAIL
TYPES OF ISOPRENOIDES
ISOLATION AND IDENTIFICATIN OF ISOPRENOIDES
•PURIFICATION
•DETERMINATION
BIOSYNTHESIS OF ISOPRINOIDS
•MEVOLANATED PATHWAY
•NAN- MEVOLANATED PATHWAY
USES OF ISOPRENOIDES
OTHER APPLICATION
•ISOPRINOID SYNTHESIS IN DNA REPLICATION AND CELL GROTH
•OTHER MEMBRANE ASSOSIATED ISOPRINOIDS
CONCLUSION
REFRANCES

3. (1) INTRODUCTION
•Isoprene (short for isoterpene), or 2-methyl-1,3-butadiene, is a
common organic compound with the formula CH2=C(CH3)CH=CH2.
•Under standard conditionsit is a colorless liquid. However, this
compound is highly volatile because of its low boiling point.
•The functional isoprene units in biological systems are dimethylallyl
diphosphate(DMADP) and its isomer isopentenyl diphosphate (IDP).
•These lipids are considered to be the largest group of natural
products, playing a wide variety of roles in physiological processes of
plants and animals, and having a number of commercial uses.
(2) DEFFINATION
“Any of a class of organic compounds (organic compound)
composed of two or more units of hydrocarbons (hydrocarbon), with
each unit consisting of five carbon atoms arranged in a specific
pattern.”

4. (4) TERPENE – GENERAL INFORMATION
•Geraniol (a contributor to rose perfumes; from geranium
oil)
•menthol (from peppermint oil),
•citral (from lemongrass oil),
•imonene (from lemon and orange oils),
• pinene(from turpentine), and camphor each have two
isoprene units.
•more units include phytol, a precursor ofchlorophyll;
•squalene, the precursor of cholesterol and othersteroids;
•lycopene, the red pigment in tomatoes and
•an important phytochemical; and carotene, the pigment
in carrots and a precursor of vitamin A.

5. (5) Chemical compound
• Isoprenoids in living organisms range in function
from pigments (pigment) and fragrances to
vitamins (vitamin) and precursors of sex
hormones (sex hormone).
•Other commercially valuable isoprenoids are
those used as flavourings, solvents, and raw
materials for chemicals.
•The name terpene specifically refers to naturally
occurring compounds that are derivatives of a
single isoprene unit, The word terpene comes
from an older spelling of turpentine (terpentine),
a cleaner that is a mixture of isoprenoids
(originally the resin of the terebinth plant).

6. (6) Iprenoids of plants and animals
In the essential oils which are found in the gummy exudates of many
trees and shrubs.
Plant isoprenoids effect growth (e.g., gibberellic acid (carotenoids).
In animals, fish liver oils, wool wax, and the yellow pigments in egg
yolk, butterfat, feathers, and fish scales.
The latices of a few species of plants contain the polyterpene
hydrocarbons rubber or gutta-percha.
The presence of menthol, citral, camphor, limonene, or α- pinene.
plant substances prevent the maturation of the insect,
Tetraterpene carotenoid pigments are the source of vitamin A.
isoprenoid include vitamin E, important in reproduction, and vitamin
K, necessary for the blood-clotting process.
The ubiquinones (ubiquinone) (coenzyme Q).
In insects (insect), certain isoprenoid substances influence maturation
and mating behaviour,
The so-called prenylated proteins do not function without the
isoprenoid.
Steroids (steroid), a class of compounds of great importance in both
plants and animals.

7. (7) OCCURRENCE
(A)Natural occurrence
Isoprene is produced and emitted by many species of trees into the atmosphere
(major producers are oaks, poplars, eucalyptus, and some legumes).
•Isoprene production from plants
Isoprene emission increases dramatically with temperature and maximizes at
around 40 °C. (thermotolerance hypothesis).
•Regulation of isoprene emission
Isoprene emission in plants is controlled both by the availability of substrate
(DMADP) and by enzyme (isoprene synthase) activity
•Biological roles
•sunny days, up to 25 μg/(g dry-leaf-weight)/hour in many oak species.
•Isoprene in other organisms
The estimated production rate of isoprene in the human body is 0.15 µmol/(kg•h),
equivalent to approximately 17 mg/day for a person weighing 70 kg.

8. (B)Industrial production
About 800,000 tonnes are produced annually. About 95% of isoprene production is used to
produce cis-1,4-polyisoprene—a synthetic version of natural rubber.
•Aims
1. Engineer yeast and E. coli cells for efficient production of isoprenoid compounds
(isoprenoid pathway engineering
2. Develop efficient isoprene production strains
3. Develop strains which produce isoprenoids with aviation fuel properties.
•They are all produced from common five-carbon building blocks, isopentenyl
pyrophosphate (IPP) and dimethylallyl phyrophosphate (DMAPP).
We are interested in two types of isoprenoids:
(1) Isoprene, a chemical feedstock which is polymerized to make rubbers and
elastomers.
(2) Higher-order isoprenoid compounds with aviation fuel properties
.

10. Application Example Details/Applications Isoprenoid Group
Pharmaceu
tical
Taxol
Limonene
Artemisinin
Chemotherapeutic
Anti-cancer agent
Anti-malarial agent
Diterpene derivitive
Monoterpene
Sesquiterpene
Food
Additive/
Supplemen
t
Carotenoids
Menthol
Tocopherol
Coenzyme Q10
Colourants
Flavour
Antioxidant
Antioxidant
Tetraterpenes
Monoterpene
Diterpene derivative
Sesquiterpene derivitive
Agriculture
/
Floriculture
Abscisic acid
Eucalyptol,
limonene
Gibberellin
Plant propagation
Insecticidal
Increases life of cut
flowers
Tetraterpene
Monoterpenes
Diterpene
Isoprenoid compounds (downstream products) with industrial applications

11. Industrial
chemical
Isoprene
Various
monoterpenes
Feedstock for synthetic
rubbers
Fragrances
Hemiterpene
Monoterpenes
Fuels/ fuel
replacements
Squalene
Isopentenol
Fernesene,
farnesol
Bio-crude
Gasoline replacement
Jet fuel
Sesquiterpene
derivitive
Hemiterpene
alcohol
Sesquiterpene
Fuel additives
Isoprenoid
alkenes, alkanes,
alcohols
Increase octane ratings,
anti-corrosives, lubricants
Several different
classes

12. (8) NATURE OF ISOPRENOIDS
(A) NATURAL PRODUCTS :
Natural products are secondary metabolites of an organism.
“natural products” can be sub-divided in to terpenoids, alkaloids, shikimates, and
polyketides
(B) SECONDARY METABOLITES
Terpenoids (come from semiterpene oligomerization)
Azadirachtin, (Neem tree)
Artemisinin, present in Artemisia annua Chinese wormwood
tetrahydrocannabinol, present in Cannabis
Steroids (Terpenes with a particular ring structure)
Saponins (plant steroids, often glycosylated)
(C) BRANCHED CHAIN ALCOHAL
- Polyisoprenoid alcohols
A - Saturated polyisoprenoids (Isopranols)

13. B - Unsaturated polyisoprenoids (prenols or polyprenols)
Polyprenols are present in several bacteria, where they act as lipid carriers in the
biosynthesis of cell surface polymers.
- 1. all trans forms :
Geraniol (from rose oil) also an effective mosquito repellent. it is produced by the scent
glands of honey bees .
Farnesol is prenol. It is present in many essential oils such as citronella, neroli,
cyclamen, lemon grass, rose, and others.
Geranylgeraniol is the acylation of proteins and the synthesis of vitamins (Vitamins E
and K). .
Phytol is a partially saturated diterpene:
n
Number of isoprene unit Number of carbons Name
0
2 10 Geraniol
1
3 15 Farnesol
2
4 20 Geranylgeraniol
3
5 25 Geranylfarnesol
7
9 45 Solanesol
8
10 50 Spadicol

14. 2. ditrans-polycis-prenols,
Bacteriaprenol type
• 3. tritrans-polycis-prenols,
Ficaprenol type
4. dolichol types,

15. (9) STRUCTURAL CLASSIFICATION OF ISOPRINOIDS
Haid to tail coupling
Tail-to-tail coupling

16. Sesquiterpenes
(10) TYPES OF ISOPRINOIDS
Monoterpenes
It has been found in other fish liver oils, in vegetable oils, in fungi (fungus), and in human
earwax and sebaceous secretions.
They are volatile oils, less dense than water, and have normal boiling points (boiling
point) in the range of 150 to 185 °C (300 to 365 °F)

17. Diterpenes
phytol, an oxygenated acyclic diterpene, is an important building block of the chlorophyll
molecule.
Triterpenes
The biochemical importance of squalene as a metabolic intermediate in the biosynthesis of
cholesterol .
Tetraterpenes
The yellow, orange, or red fat-soluble plant and animal pigments, known as carotenoids
(carotenoid), are classed as tetraterpenes.
Polyterpenes
rubber, which occurs in the latex of the rubber tree, is a polyterpene hydrocarbon, in which n is
4,000–5,000.

18. (11) ISOLATION AND IDENTIFICATIN OF ISOPRENOIDES
•PURIFICATION
•DETERMINATION
(12) BIOSYNTHESIS OF ISOPRINOIDES
 Isopentenyl diphosphate (IPP), the universal building block for all isoprenoids is
formed by two different biosynthetic routes: the well known acetate/mevalonate
pathway and the non mevalonate pathway starting from pyruvate and
grycereldihyde 3-phosphate.
 In contrast to the classical mevalonate pathway of isoprenoid biosynthesis,
plants and apicomplexan protozoa such as malaria parasites have the ability to
produce their isoprenoids (terpenoids) using an alternative pathway, the non-
mevalonate pathway, which takes place in their plastids. In addition, most bacteria
including important pathogens such as Mycobacterium tuberculosis synthesize IPP
and DMAPP via the non-mevalonate pathway.

21. Reactants Enzyme Product
Pyruvate and
glyceraldehyde 3-
phosphate
DOXP synthase (Dxs)
1-Deoxy-D-xylulose 5-phosphate
(DOXP)
DOXP DOXP reductase (Dxr, IspC)
2-C-methylerythritol 4-
phosphate (MEP)
MEP
4-diphosphocytidyl-2-C-
methyl-D-erythritol synthase
(YgbP, IspD)
4-diphosphocytidyl-2-C-
methylerythritol (CDP-ME)
CDP-ME
4-diphosphocytidyl-2-C-
methyl-D-erythritol kinase
(YchB, IspE)
4-diphosphocytidyl-2-C-methyl-
D-erythritol 2-phosphate (CDP-
MEP)
CDP-MEP
2-C-methyl-D-erythritol 2,4-
cyclodiphosphate synthase
(YgbB, IspF)
2-C-methyl-D-erythritol 2,4-
cyclopyrophosphate (MEcPP)
MEcPP
HMB-PP synthase (GcpE,
IspG)
(E)-4-Hydroxy-3-methyl-but-2-
enyl pyrophosphate (HMB-PP)
HMB-PP HMB-PP reductase (LytB, IspH) IPP and DMAPP

22. Inhibition
Fosmidomycin specifically inhibits DOXP reductoisomerase, a key
enzyme in the non-mevalonate pathway, and therefore represents an
attractive candidate as antibiotic or antimalarial drug.
T cell activation
The intermediate HMB-PP is the natural activator for human Vγ9/Vδ2 T
cells, the major γδ T cell population in peripheral blood.
(13) Uses of isoprenoids
(15) OTHERS IMPORTANCE
•Role of isoprenoid synthesis in DNA replication and cell growth

23. (b) OTHER MEMBRANE-ASSOCIATED ISOPRENOIDS
STRUCTURES, BIOCHEMISTRY AND FUNCTION
1.
1. Plastoquinone
2. Ubiquinone (Coenzyme Q)
3. Phylloquinone (Vitamin K)
Phylloquinone or 2-methyl-3-phytyl-1,4-naphthoquinone is synthesised in the chloroplasts of plants
where it is a key component of the photosystem I complex and serves as an electron acceptor.

24. 5. Retinol (Vitamin A)
The term ‘vitamin A’ is used to denote retinol or all-trans-retinol and
a family of biologically active retinoids derived from this. These are
only found in animal tissues, the biosynthetic precursors of these
compounds are plant carotenoids (provitamin A).
6. Undecaprenyl Phosphate and Lipid II
Undecaprenyl phosphate (a C55 isoprenoid), also referred to as
bactoprenol, is a lipid intermediate that is essential for the
biosynthesis of peptidoglycan and many other cell-wall
polysaccharides, and for N-linked protein glycosylation in prokaryotes
(both in Gram-negative and Gram-positive bacteria).

25. 7. Farnesy Pyrophosphate and Related Compounds
Farnesyl pyrophosphate is a key intermediate in the biosynthesis of
sterols such as cholesterol and it is the donor of the farnesyl group for
isoprenylation of many proteins (see the web page on proteolipids).

26. (1 ) Lehninger Principle of biochemistry:
David L.Nelson Michael M.Cox
(2) TODD & HOWARDS MASON –
BIOCHEMISTRY ,4th EDITION
Websites:
www.kbiotech.com
www.wikipedia.com