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The terpenoids (), sometimes called isoprenoids, are a large and diverse class of naturally-occurring organic chemicals
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 similar to terpene
Terpene

Terpenes are a large and varied class of hydrocarbons, produced primarily by a wide variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium....
s, derived from five-carbon isoprene
Isoprene

Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. It is commonly used in industry, is an important biological material, and can be a harmful environmental pollutant and toxicant when present in excess quantities....
 units assembled and modified in thousands of ways. Most are multicyclic structures that differ from one another not only in functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
s but also in their basic carbon skeletons.






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Ipp
The terpenoids (), sometimes called isoprenoids, are a large and diverse class of naturally-occurring organic chemicals
Organic compound

An organic compound is any member of a large class of chemical compounds whose molecules contain carbon. For historical reasons discussed below, a few types of compounds such as carbonates, simple oxides of carbon and cyanides, as well as the allotropes of carbon, are considered Inorganic compound....
 similar to terpene
Terpene

Terpenes are a large and varied class of hydrocarbons, produced primarily by a wide variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium....
s, derived from five-carbon isoprene
Isoprene

Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. It is commonly used in industry, is an important biological material, and can be a harmful environmental pollutant and toxicant when present in excess quantities....
 units assembled and modified in thousands of ways. Most are multicyclic structures that differ from one another not only in functional group
Functional group

In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules....
s but also in their basic carbon skeletons. These lipid
Lipid

Lipids are broadly defined as any fat-soluble , naturally-occurring molecule, such as fats, oils, waxes, cholesterol, sterols, fat-soluble vitamins , monoglycerides, diglycerides, phospholipids, and others....
s can be found in all classes of living things, and are the largest group of natural products.

Plant terpenoids are used extensively for their aromatic qualities. They play a role in traditional herbal remedies and are under investigation for antibacterial, antineoplastic
Antineoplastic

Antineoplastics are drugs that inhibit and combat the development of neoplasms.In the Anatomical Therapeutic Chemical Classification System, they are classified under ATC code L01#L01D Cytotoxic antibiotics and related substances....
, and other pharmaceutical functions. Terpenoids contribute to the scent of eucalyptus
Eucalyptus

Eucalyptus is a diverse genus of Flowering plant trees in the Myrtus family, Myrtaceae. Members of the genus dominate the tree flora of Australia....
, the flavors of cinnamon
Cinnamon

Cinnamon is a small evergreen tree 10?15 metres tall, belonging to the family Lauraceae, and is native to Sri Lanka.The leaf are ovate-oblong in shape, 7?18 cm long....
, cloves, and ginger
Ginger

Ginger is a spice which is used for cooking and is also consumed whole as a delicacy or medicine. It is the rhizome of the Zingiber, Zingiber officinale....
, and the color of yellow flowers. Well-known terpenoids include citral
Citral

Citral, or 3,7-dimethyl-2,6-octadienal or lemonal, is either of a pair of terpenoids with the molecular formula Carbon10Hydrogen16Oxygen....
, menthol
Menthol

Menthol is an organic compound #Production or obtained from peppermint or other Mentha oils. It is a waxy, crystalline substance, clear or white in color, which is solid at room temperature and melts slightly above....
, camphor
Camphor

Camphor is a waxy, white or transparent solid with a strong, aromatic odor. It is a terpenoid with the chemical formula carbon10hydrogen16oxygen....
, Salvinorin A
Salvinorin A

Salvinorin A is the main active psychotropic molecule in Salvia divinorum, a Mexican plant which has a long history of use as an entheogen by indigenous Mazatec shamans....
 in the plant Salvia divinorum
Salvia divinorum

Salvia divinorum, also known as Diviner?s Sage, ska Mar?a Pastora, or simply by the genus name Salvia, is a Psychoactive drug herb which can induce strong dissociative drug effects....
, and the cannabinoids found in Cannabis
Cannabis

Cannabis is a genus of flowering plants that includes three putative species, Cannabis sativa L., Cannabis indica Lam., and Cannabis ruderalis Janisch....
.

The steroid
Steroid

A steroid is a terpenoid lipid characterized by a carbon skeleton with four fused rings, generally arranged in a 6-6-6-5 fashion.Steroids vary by the functional groups attached to these rings and the oxidation state of the rings....
s and sterol
Sterol

Sterols are an important class of organic molecules. They occur naturally in plants, animals and fungi, with the most familiar type of animal sterol being cholesterol, which has been shown to contribute to high blood pressure and heart disease....
s in animals are biologically produced from terpenoid precursors. Sometimes terpenoids are added to protein
Protein

Proteins are organic compounds made of amino acids arranged in a linear chain and joined together by peptide bonds between the carboxyl and amino groups of adjacent amino acid Residue ....
s, e.g., to enhance their attachment to the cell membrane
Cell membrane

The cell membrane is the interface between the cellular machinery inside the cell and the fluid outside.It is a semipermeable lipid bilayer found in all cell ....
; this is known as isoprenylation.

Many of these are substrate
Substrate (biochemistry)

In biochemistry, a substrate is a molecule upon which an enzyme acts. Enzymes catalysis chemical reactions involving the substrate. The substrate binds with the enzyme active site, and an enzyme-substrate complex is formed....
s for plant Cytochrome P450.

Structure and classification


Terpene
Terpene

Terpenes are a large and varied class of hydrocarbons, produced primarily by a wide variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium....
s are hydrocarbon
Hydrocarbon

In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. With relation to chemical terminology, aromatic hydrocarbons or arenes, alkanes, alkenes and alkyne-based compounds composed entirely of carbon or hydrogen are referred to as "pure" hydrocarbons, whereas other hydrocarbons with bonded com...
s resulting from the combination of several isoprene
Isoprene

Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. It is commonly used in industry, is an important biological material, and can be a harmful environmental pollutant and toxicant when present in excess quantities....
 units. Terpenoids can be thought of as modified terpenes, wherein methyl group
Methyl group

In chemistry, a methyl group is a hydrophobic alkyl functional group named after methane . It has the chemical formula -3 and is often abbreviated -Me....
s have been moved or removed, or oxygen
Oxygen

Oxygen no O2 produced; 2) O2 produced, but absorbed in oceans & seabed rock; 3) O2 starts to gas out of the oceans, but is absorbed by land surfaces and formation of ozone layer; 4-5) O2 sinks filled and the gas accumulates]]...
 atoms added. (Some authors use the term "terpene" more broadly, to include the terpenoids.) Just like terpenes, the terpenoids can be classified according to the number of isoprene units used:
  • Monoterpenoids, 2 isoprene units
  • Sesquiterpenoids, 3 isoprene units
  • Diterpenoids, 4 isoprene units
  • Sesterterpenoids, 5 isoprene units
  • Triterpenoids, 6 isoprene units
  • Tetraterpenoids, 8 isoprene units
  • Polyterpenoids with a larger number of isoprene units
Terpenoids can also be classified according to the number of cyclic structures they contain.

Biosynthesis

There are two metabolic pathway
Metabolic pathway

In biochemistry, a metabolic pathway is a series of chemistry reactions occurring within a cell . In each pathway, a principal chemical is modified by chemical reactions....
s of creating terpenoids:

Mevalonic acid pathway


Many organisms manufacture terpenoids through the HMG-CoA reductase pathway
HMG-CoA reductase pathway

The mevalonate pathway or HMG-CoA reductase pathway or mevalonate-dependent route or isprenoid pathway, is an important cell metabolic pathway present in all higher eukaryotes and many bacteria....
, the pathway that also produces cholesterol
Cholesterol

Cholesterol is a lipidic, waxy alcohol found in the cell membranes and transported in the blood plasma of all animals. It is an essential component of mammalian cell membranes where it is required to establish proper membrane permeability and membrane fluidity....
. The reactions take place in the cytosol
Cytosol

The cytosol or intracellular fluid is the liquid found inside cell . In eukaryotes this liquid is separated by cell membranes from the contents of the organelles suspended in the cytosol, such as the mitochondrial matrix inside the mitochondrion....
. The pathway was discovered in the 1950s.

MEP/DOXP pathway


The 2-C-methyl-D-erythritol 4-phosphate/1-deoxy-D-xylulose 5-phosphate pathway (MEP/DOXP pathway), also known as non-mevalonate pathway
Non-mevalonate pathway

The non-mevalonate pathway or 2-C-methyl-D-erythritol 4-phosphate/1-deoxy-D-xylulose 5-phosphate pathway of isoprenoid biosynthesis is an alternative metabolic pathway leading to the formation of isopentenyl pyrophosphate and dimethylallyl pyrophosphate that has been elucidated only recently....
 or mevalonic acid
Mevalonic acid

Mevalonic acid is a key organic compound in biochemistry. The anion of mevalonic acid, the predominant form in biological media, is known as mevalonate....
-independent pathway, takes place in the plastid
Plastid

Plastids are major organelles found in plants and algae. Plastids are the site of manufacture and storage of important chemical compounds used by the cell....
s of plants and apicomplexa
Apicomplexa

The Apicomplexa are a large group of protists, characterized by the presence of a unique organelle called an apical complex . They are unicellular, spore-forming, and exclusively parasites of animals....
n protozoa, as well as in many bacteria
Bacteria

The Bacteria are a large group of unicellular microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals....
. It was discovered in the late 1980s.

Pyruvate and glyceraldehyde 3-phosphate
Glyceraldehyde 3-phosphate

Glyceraldehyde 3-phosphate, also known as triose phosphate or 3-phosphoglyceraldehyde and abbreviated as G3P, GADP, GAP, TP, GALP or PGAL, is a chemical compound that occurs as an intermediate in several central metabolic pathways of all organisms....
 are converted by DOXP synthase (Dxs) to 1-deoxy-D-xylulose 5-phosphate, and by DOXP reductase (Dxr, IspC) to 2-C-methyl-D-erythritol 4-phosphate (MEP). The subsequent three reaction steps catalyzed by 4-diphosphocytidyl-2-C-methyl-D-erythritol synthase (YgbP, IspD), 4-diphosphocytidyl-2-C-methyl-D-erythritol kinase (YchB, IspE), and 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase (YgbB, IspF) mediate the formation of 2-C-methyl-D-erythritol 2,4-cyclopyrophosphate (MEcPP). Finally, MEcPP is converted to (E)-4-hydroxy-3-methyl-but-2-enyl pyrophosphate (HMB-PP) by HMB-PP synthase (GcpE, IspG), and HMB-PP is converted to isopentenyl pyrophosphate
Isopentenyl pyrophosphate

Isopentenyl pyrophosphate is an intermediate in the classical, HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids....
 (IPP) and dimethylallyl pyrophosphate
Dimethylallyl pyrophosphate

Dimethylallyl pyrophosphate is an intermediate product of both mevalonic acid pathway and DOXP/methylerythritol phosphate pathway. It is an isomer of isopentenyl pyrophosphate and exists in virtually all life forms....
 (DMAPP) by HMB-PP reductase (LytB, IspH).

IPP and DMAPP are the end-products in either pathway, and are the precursors of isoprene
Isoprene

Isoprene is a common synonym for the chemical compound 2-methyl-1,3-butadiene. It is commonly used in industry, is an important biological material, and can be a harmful environmental pollutant and toxicant when present in excess quantities....
, monoterpenoids (10-carbon), diterpenoids (20-carbon), carotenoid
Carotenoid

Carotenoids are organic compound pigments that are naturally occurring in chromoplasts of plants and some other photosynthesis organisms like algae, some types of fungus and some bacterium....
s (40-carbon), chlorophyll
Chlorophyll

Chlorophyll is a green pigment found in most plants, algae, and cyanobacteria. Its name is derived from Greek language: ?????? and f????? ....
s, and plastoquinone
Plastoquinone

Plastoquinone is a quinone molecule involved in the electron transport chain in the light-dependent reactions of photosynthesis. Plastoquinone is reduced , forming plastoquinol....
-9 (45-carbon). Synthesis of all higher terpenoids proceeds via formation of geranyl pyrophosphate
Geranyl pyrophosphate

Geranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of farnesyl pyrophosphate, geranylgeranyl pyrophosphate, cholesterol, terpenes and terpenoids....
 (GPP), farnesyl pyrophosphate
Farnesyl pyrophosphate

Farnesyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids.It is the immediate precursor of squalene , dehydrodolichol diphosphate , and geranylgeranyl pyrophoshate ....
 (FPP), and geranylgeranyl pyrophosphate
Geranylgeranyl pyrophosphate

Geranylgeranyl pyrophosphate is an intermediate in the HMG-CoA reductase pathway used by organisms in the biosynthesis of terpenes and terpenoids....
 (GGPP).

Although both pathways, MVA and MEP, are mutually exclusive in most organisms, interactions between them have been reported in plants and few bacteria
Bacteria

The Bacteria are a large group of unicellular microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals....
 species.

OrganismPathways
Bacteria
Bacteria

The Bacteria are a large group of unicellular microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals....
MVA or MEP
Archaea
Archaea

The Archaea are a group of single-celled microorganisms. A single individual or species from this domain is called an archaeon . Archaea, like bacteria, are prokaryotic....
MVA
Green Algae
Algae

Algae are a large and diverse group of simple, typically autotrophic organisms, ranging from unicellular to multicellular forms. The largest and most complex marine forms are called seaweeds....
MEP
Plant
Plant

Plants are Life organisms belonging to the Kingdom Plantae. They include familiar organisms such as trees, herbs, bushes, grasses, vines, ferns, mosses, and green algae....
s		 MVA and MEP
Animal
Animal

Animals are a major group of multicellular, eukaryotic organisms of the Kingdom Animalia or Metazoa. Their body plan eventually becomes fixed as they develop, although some undergo a process of metamorphosis later on in their life....
s		 MVA
Fungi MVA


See also

  • Pharmacology
    Pharmacology

    Pharmacology is the study of drug action. More specifically it is the study of the interactions that occur between a living organism and exogenous chemicals that alter normal biochemical function....


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