Terpenes & Terpenoids 4.

Slides:



Advertisements
Similar presentations
Terpenes.
Advertisements

Ultraviolet-Visible (UV-VIS) Spectroscopy
Chapter 25 Lipids Jo Blackburn Richland College, Dallas, TX Dallas County Community College District  2006,  Prentice Hall Organic Chemistry, 6 th Edition.
Essential Oils Composition KIMIA MINYAK ATSIRI. ESSENTIAL OIL COMPOSITION Essential Oils are complex mixture of sometimes hundreds of chemicals compounds.
Chapter 2. Fundamental Concepts in Understanding Bioenergy and Biobased Products Organic Chemistry.
N ATURE ’ S C HEMISTRY Fragrances and Skin Care. E SSENTIAL O ILS Essential oils are the concentrated extracts of volatile, non-water-soluble aroma compounds.
Madcasim, Nasser Jr. M. Galan, Pitt Shaughn Mikho.
Terpenes. Terpenes are a large and diverse class of organic compounds, produced by a variety of plants, particularly conifers, though also by some insects.
Wood Chemistry PSE 406 Lecture 121 Wood Chemistry PSE 406/Chem E 470 Lecture 12 Wood Extractives Introduction Terpenes and Sesquiterpenes.
Unsaturated Hydrocarbons
Biochemistry. Organization Human body Organ systems Organs Tissues Cells Organic Molecules.
1 Electrophilic Reactions. 2 3 Electrophilic Reactions Addition to unsaturated carbon Alkenes + Alkynes Unsaturated hydrocarbon Unsaturated hydrocarbon:
Online Counseling Resource YCMOU ELearning Drive… School of Architecture, Science and Technology Yashwantrao Chavan Maharashtra Open University, Nashik.
26.11 Steroids: Cholesterol. Structure of Cholesterol Fundamental framework of steroids is the tetracyclic unit shown.
200 pt 300 pt 400 pt 500 pt 100 pt 200 pt 300 pt 400 pt 500 pt 100 pt 200 pt 300 pt 400 pt 500 pt 100 pt 200 pt 300 pt 400 pt 500 pt 100 pt 200 pt 300.
Lipids.
© 2011 Pearson Education, Inc. 1 Organic Chemistry 6 th Edition Paula Yurkanis Bruice Chapter 27 The Organic Chemistry of Lipids.
26.7 Terpenes: The Isoprene Rule
1 TERPENES. 2 TERPENES The Czech chemist Leopold Ruzicka ( born 1887) showed that many compounds found in nature were formed from multiples of five carbons.
Mevalonic Acid Pathway Many constituents are unsaturated hydrocarbons Ketons, alcohols, simple hydrocarbons are formed Through acetate-mevalonate pathway.
TerpenesTerpenes. Terpenes are a class of molecules that typically contain either ten or fifteen carbon atoms built from a five-carbon building block.
Photosynthesis Chapter 3.
PTT103 BIOCHEMISTRY LIPID Pn Syazni Zainul Kamal School of Bioprocess Engineering.
Organic Chemistry 4 th Edition Paula Yurkanis Bruice Irene Lee Case Western Reserve University Cleveland, OH ©2004, Prentice Hall Chapter 26 Lipids.
Chapter 23 Lipids Created By Prof. Gary F. Porter, Ph.D. Copyright © 2014 by John Wiley & Sons, Inc. All rights reserved.
Terpenes: The Isoprene Rule. Terpenes Terpenes are natural products that are structurally related to isoprene. H2CH2CH2CH2C C CH 3 CH CH 2 or Isoprene.
5-1 5 Organic Chemistry William H. Brown & Christopher S. Foote.
5-1 5 Copyright © 2000 by John Wiley & Sons, Inc. All rights reserved. Introduction to Organic Chemistry 2 ed William H. Brown.
Organic Molecules and Biomolecules
HC CHEMISTRY HC CHEMISTRY NATURES’ CHEMISTRY (E) Fragrances.
PHOTOSYNTHESIS. All organisms use energy to carry out the functions of life. They obtain this energy directly or indirectly from the sun. sun Which organisms.
Volatile oil. Volatile oils different from fixed – secreted in oil cells in specialised structures ducts, gland, cell or glandular hairs – frequently.
Lipids Fatty Acids Fats Phospholipids Steroids Waxes.
6.4 The Building Blocks of Life
Chapter 4 Alkenes: Structure, Nomenclature, Stability, and an Introduction to Reactivity (Part I) Essential Organic Chemistry Paula Yurkanis Bruice.
VOLATILE OILS & RELATED TERPENES
Terpenes & Terpenoids 4.

CHAPTER 11 Terpenes.
6 Lipids, Membranes and Cells. Table 3.1 The Building Blocks of Organisms 15% 7% 2% 26% 2% Water 70%
Lipids. The lipids are organic molecules, present in nature; are insoluble in water (hydrophobic), while they are soluble in organic solvents non-polar,
Hydrocarbons Systematic naming Alcohols. P,S,T.
The Organic Chemistry of Lipids
Chemical Principles.
Created By Prof. Gary F. Porter, Ph.D.
Chapter 28 (Secondary) Natural Products
Carbon Structures, and Lipids.
Higher Chemistry Perfumes – Smelly Chemistry
The Organic Chemistry of the Metabolic Pathways • Terpene Biosynthesis
Chloroplasts Chromoplasts Leucoplasts Plastids
Lipids Lipids are hydrophobic, nonpolar organic molecules. They are insoluble in water and highly soluble in one or more of the following solvents:
Lipids Section 3.3.
Alkenes: Structure and Nomenclature
Natural Product The organic compounds isolated from the living organism i.e plants, animals and micro organism are generally known as Natural products.
Alkenes 12/1/2018 Dr seemal Jelani.
Fragrances 04/12/2018.
Cells and Energy How does a cell obtain energy?
Terpenes.
Terpenes: The Isoprene Rule
Carbon Compounds and Biomolecules -Most of the compounds that make up your body contain carbon. -Carbon containing compounds are often called “organic”
CHAPTER 11 Terpenes.
Introduction to Biochemistry. Objectives  Know what biochemistry is and its principle.  Know the components of a cell and its major types of bio- molecules.
The main functions of food are:
Bioorganic Lipids 4/6/2019 Dr Seemal Jelani Chem-160.
Photosynthesis 4C.
PHOTOSYNTHESIS.
PHOTOSYNTHESIS.
Fragrances 22/05/2019.
Alkenes: Structure and Nomenclature
Bioorganic Lipids 12/5/2019 Dr Seemal Jelani Chem-160.
Presentation transcript:

Terpenes & Terpenoids 4

Terpenes - class of >20,000 compounds containing carbon atoms in multiples of five Terpenoids - oxygen-containing terpenes (alcohols, ketones, aldehydes

The name "terpene" is derived from the word "turpentine" Terpenes and terpenoids are the primary constituents of the essential oils of many types of plants and flowers.  rose oil (zencefil) (kereviz)

Isoprene (2-methyl-1,3-butadiene) Terpenes Terpenes are natural products that are structurally related to isoprene. H2C C CH3 CH CH2 or Isoprene (2-methyl-1,3-butadiene)

Terpenes Myrcene (isolated from oil of bayberry) is a typical terpene. CH2 CH3 CH3C CHCH2CH2CCH or

The Isoprene Unit An isoprene unit is the carbon skeleton of isoprene (ignoring the double bonds) Myrcene contains two isoprene units.

The Isoprene Unit The isoprene units of myrcene are joined "head-to-tail." head tail tail head

Classification of Terpenes Class Number of carbon atoms Monoterpene 10 Sesquiterpene 15 Diterpene 20 Sesterpene 25 Triterpene 30 Tetraterpene 40

a-Phellandrene (eucalyptus) Representative Monoterpenes OH O H a-Phellandrene (eucalyptus) Menthol (peppermint) Citral (lemon grass)

a-Phellandrene (eucalyptus) Representative Monoterpenes OH O H a-Phellandrene (eucalyptus) Menthol (peppermint) Citral (lemon grass)

a-Phellandrene (eucalyptus) Representative Monoterpenes a-Phellandrene (eucalyptus) Menthol (peppermint) Citral (lemon grass)

Representative Sesquiterpenes H a-Selinene (celery)

Representative Sesquiterpenes H a-Selinene (celery)

Representative Sesquiterpenes a-Selinene (celery)

Representative Diterpenes OH Vitamin A

Representative Diterpenes OH Vitamin A

Representative Diterpenes Vitamin A

Squalene (shark liver oil) Representative Triterpene tail-to-tail linkage of isoprene units Squalene (shark liver oil)

Finding the isoprene building block - cyclic compounds Finding the isoprene building block - sesquiterpenes (C15)

Finding the isoprene building block - triterpenes (C30) - Squalene has a natural and vital part in the synthesis of all plant and animal sterols, including cholesterol, steroid hormones, and vitamin D in the human body

Finding the isoprene building block - tetraterpenes (C40) Lycopene is responsible for the red color in tomatoes and watermelon

 -carotene is the compound that causes carrots and apricots to be orange

” C10 terpenoids The precursor to C10 terpenoids (monoterpenes) is Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), which consists of two C5 “isoprene units” that are joined “head-to-tail PP head - tail head - tail

Geranyl pyrophosphate

C15 sesquiterpenoids are derived from Farnesyl diphosphate, which consists of three C5 “isoprene units” that are joined “head-to-tail”

C20 diterpenoids are derived from Geranylgeranyl diphosphate, which consists of four C5 “isoprene units” that are joined “head-to-tail”

Terpenoid nomenclature Groups and subgroups Based on pathways Classification IUPAC CAS Trivial name(derived from the structural family Or relate to natural source)

Examples of the co-existence of systematics Semi-systemetic and trivial names

Menthol – a cyclic terpenoid This terpene has been oxidised to a terpenoid

Absinthe – a cyclic terpenoid a potent green aniseed-flavoured liqueur, originally made with the shrub wormwood.(the seed of the anise, used in cooking and herbal medicine) This terpene has been oxidised to a terpenoid

Camphor – a cyclic terpenoid

a-Selinene – a cyclic terpene 3 isoprene units 15 carbon atoms

β-carotene – a linear terpene 8 isoprene units 40 carbon atoms

Which unit makes up every terpene? Isoprene Unit Questions Which unit makes up every terpene? Isoprene Unit How many carbons are there in an isoprene unit? Five What is the systematic name for isoprene? 2-methylbuta-1,3-diene What is an oxidised terpene known as? Terpenoid

Carvone Occurs in Enantiomeric forms Also known as Meridian fennel, Persian carrot Uses Carvone –Latin name for Caraway, carum carvi Basic carbon skeleton 1-isopropyl-4-methylcyclohexane common in nature the genus mentha includes various types of mint

saturated ketone of the p- menthane family of monoteroenoids Greek letters Use to distinguish between isomeric terpenoids Depends on In order in which the isomers were discovered Their abundance

α- Pinene ¾ component of turpentine oil by weight β- Pinene next most significant component

Cyclic Terpenoids α, β, and γ refers to the location of double bond in isomeric olefins α - endocyclic tri substituted double bond β- A tetra substituted olefinic bond γ- exocyclic methylene function Example E1 reaction

α - endocyclic tri substituted double bond A trisubstituted alkene is an alkene in the molecule of which the doubly bonded carbons are bonded to a total of three carbon atoms excluding each other.

A tetrasubstituted alkene is an alkene in the molecule of which the doubly bonded carbons are bonded to a total of four carbon atoms excluding each other.

Methylene group γ- exocyclic methylene function

THE ROLE OF TERPENOIDS IN NATURE Terpenoids are produced by a wide variety of plants, animals and micro-organisms. As for all metabolites, the synthesis of terpenoids places a metabolic load on the organism which produces them and so, almost invariably, there is a role which the material plays and for which it is synthesized.

The roles which the terpenoids play in living organisms can be grouped into three classes: Functional Defense and (producing resins and gums Acacia gummiferae) Communication.

Examples Vitamin A, or retinol, is the precursor for the pigment in eyes which detects light and is therefore responsible for the sense of sight. Vitamin E, or tocopherol, is an important antioxidant which prevents oxidative damage to cells.

Vitamin D2, also known as calciferol, regulates calcium metabolism in the body and is therefore vital for the building and maintenance of bone. Chlorophyll-a is a green pigment found, for example, in plant leaves and is a key factor of photosynthesis through which atmospheric carbon dioxide is converted to glucose.

Calciferol

Tocopherol

Chlorophyll

Communication Terpenoids are also used as chemical messengers. If the communication is between different parts of the same organism, the messenger is referred to as a hormone. Giberellic acid is a hormone used by plants to control their rate of growth. Testosterone and oestrone are mammalian sex hormones. .

Oesteron

Semiochemicals Chemicals that carry signals from one organism to another are known as semiochemicals. These can be grouped into two main classes. Pheromones Allelochemicals

Pheromones If the signal is between two members of the same species, the messenger is called a pheromone. Pheromones carry different types of information.

Not all species use pheromones. In those which do, some may use only one or two pheromones while others, in particular the social insects such as bees, ants and termites, use an array (arrangement)of chemical signals to organise most aspects of their lives.

Ants and termites use trail pheromones to mark a path between the nest and a food source. This explains why ants are often seen walking in single file over long distances. One such trail pheromone is Neocembrene-A which is produced and used by termites of the Australian species Nasutitermes exitiosus..

The social insects also use alarm, aggregation, dispersal and social pheromones to warn of danger and to control group behaviour.

Allelochemicals Chemicals which carry messages between members of different species are known as Allelochemicals. Within this group, Allomones benefit the sender of the signal, Kairomones its receiver and with Synomones both the sender and receiver benefit.

Examples Camphor and d-limonene are Allomones in that the trees which produce them are protected from insect attack by their presence. These trees are protected from termite attack because the d-limonene they produce is an alarm pheromone for termites that live in the same area.

Similarly, antifeedants (a naturally occurring substance in certain plants that adversely affects insects or other animals that eat them.)could be considered to be Allomones since the signal generator, the plant, receives the benefit of not being eaten

Myrcene is a Kairomone, in that it is produced by the ponderosa pine and its presence attracts the females of the bark beetle, Dendroctonous brevicomis

Geraniol is found in the scent of many flowers such as the rose. Its presence attracts insects to the flower and it can be classified as a Synomone since the attracted insect finds nectar and the plant obtains a pollinator.