1.Terpenoids introduction
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This document discusses terpenoids, which are secondary plant metabolites derived from isoprene units. It defines terpenoids and notes that they are optically active and composed of isoprene units, called isoprenoids. The document classifies terpenoids based on the number of isoprene units they contain, such as monoterpenoids containing two isoprene units. It also discusses the biosynthesis of terpenoids from acetyl CoA and mevalonic acid. In summary, the document provides background information on terpenoids, including their definition, classification, biosynthesis, and importance.
![• Terpene represents only
hydrocarbon of molecular fomula
[C5H8]2
.
• Terpenoids with general formula
[C5H8] n as well as their
oxygenated, hydrogenated and
dehydrogenated derivatives.
• Terpenoids are optically active.](https://image.slidesharecdn.com/1-170223052431/85/1-Terpenoids-introduction-4-320.jpg)
![Classification based on number of isoprene unit
Terpenoids no of isoprene Molecular formula
Hemiterpene or isoprene 1 C5H8
Monoterpenoids 2 C10H16
Sesquiterpenoids 3 C15 H24
Diterpenoids 4 C20 H32
Sesterterpenoids 5 C25H40
Triterpenoids 6 C 30 H48
Tetraterpenoids 8 C40H64
Polyterpenoids n [C5H8]n](https://image.slidesharecdn.com/1-170223052431/85/1-Terpenoids-introduction-12-320.jpg)
![Dimethyl Allyl Pyrophosphate
Geranyl Pyrophosphate [Monoterpenoid
c1O]
Farnesyl pyrophosphate [
Sesquiterpenoids- C15]
GGPPDiterpenoids
C20
Carotenoids
C40
Polyterpenoids
C40](https://image.slidesharecdn.com/1-170223052431/85/1-Terpenoids-introduction-15-320.jpg)
1.Terpenoids introduction
- 1. Terpenoids Prepared by Dr. N.GOPINATHAN ASSISTANT PROFESSOR DEPARTMENT OF PHARMACEUTICAL CHEMISTRY FACULTY OF PHARMACY SRI RAMACHANDRA UNIVERSITY CHENNAI-116 TAMILNADU INDIA
- 2. Primary Metabolite Secondary Metabolites 1) Primary metabolites are essential for life process. (Growth of the cells) These are non-essential. 2)These are identified universally, throughout the source. These are seldom, like in some portions of the source, like steam, bark, etc. 3) These are produced continuously during the growth phase and are involved in primary metabolic processes such as respiration and photosynthesis, etc These compounds do not have a continuous production. However they are produced during non-growth phase of cells. (Synthetically). 4) Heavy mol.wt compounds. Low mol.wt compounds. 5) Structure cannot be drawn.(Undefined) Can be drawn. (Defined) 6) DNA, Proteins, carbohydrates, and lipids are the main primary metabolites. Alkaloids, Terpenoid, phenolics, sterols, steroids, essential oils and lignins, etc
- 3. Definition • Terpene – german word – terpentin – mixture of isomeric hydrocarbon occur in turpentine. • The oxygenated derivatives of these hydrocarbon like alcohol, aldehydes, ketones were called as camphor. • When terpenes are modified chemically the resulting compounds are terpenoids.
- 4. • Terpene represents only hydrocarbon of molecular fomula [C5H8]2 . • Terpenoids with general formula [C5H8] n as well as their oxygenated, hydrogenated and dehydrogenated derivatives. • Terpenoids are optically active.
- 5. • The suffix ene signifies unsaturated hydrocarbon so it is inappropriate to include the compounds such as alcohols, aldehydes and ketones. • The terpenoids composed of isoprene units they are called as isoprenoids. • Major terphenoids occur in plant kingdom but few obtain from other source.
- 6. • Most of the fragrance component of plant are volatile and isolated by steam distillation is called as essential oil. • Due to their pleasant smelling nature the mono and sesquiterpenoids are of considerable commercial importance particularly in perfumery.
- 7. Essential oil Terpenoids Turpentine Pinene Caraway Carvone Coriander Linalol, pinene Eucalyptus Cineole Lemon D-Limonene Peppermint Menthol
- 8. • The di and tri terpenoids are non volatile obtained from gums and resins of plant without perfumery value. • The tetra terpenoids constitute a group of compounds called carotenoids • Rubber is the most important polyterpenoid
- 9. Why terpenoids in pharmacy? • Terpenoids shows biological activity like insecticidal, anthelmintic and antiseptic action thus useful in pharmacy.
- 10. Properties • Colorless liquid lighter than water. • Boils between 150 – 180 ◦ C • Few are solids • Optically active • Unsaturated compound with one or more double bond. • It undergoes addition reaction, Polymerization and dehydrogenation
- 11. • Thermal decomposition yield isoprene.
- 12. Classification based on number of isoprene unit Terpenoids no of isoprene Molecular formula Hemiterpene or isoprene 1 C5H8 Monoterpenoids 2 C10H16 Sesquiterpenoids 3 C15 H24 Diterpenoids 4 C20 H32 Sesterterpenoids 5 C25H40 Triterpenoids 6 C 30 H48 Tetraterpenoids 8 C40H64 Polyterpenoids n [C5H8]n
- 13. Terpenoids subdivided into subclasses according to number of rings present in the molecule • Acyclic terpenoid– open chain-citral • Monocyclic terpenoid – one ring - limonene • Bicyclic terpenoid – two ring - camphor • Tricyclic terpenoid- three ring • Tetracyclic terpenoid – four ring
- 14. Acetyl COA Acetoacetyl COA HMG COA Mevalonic acid Isopentenyl pyrophosphate
- 15. Dimethyl Allyl Pyrophosphate Geranyl Pyrophosphate [Monoterpenoid c1O] Farnesyl pyrophosphate [ Sesquiterpenoids- C15] GGPPDiterpenoids C20 Carotenoids C40 Polyterpenoids C40
- 16. Geranyl farnesyl pyrophospate Sesterpenoids C25 Geranyl pyrophosphate act as a key intermediate in the biosynthesis of about 40 terpenoids
- 17. Thank you