The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound

isoprene Isoprene, or 2-methyl-1,3-butadiene, is a common volatile organic compound with the formula CH2=C(CH3)−CH=CH2. In its pure form it is a colorless volatile liquid. Isoprene is an unsaturated hydrocarbon. It is produced by many plants and animals ...

and its derivatives called

terpene Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n > 1. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes ...

diterpene Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ...

s, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional

functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the r ...

s, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known

natural products A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical sy ...

. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists. Plant terpenoids are used for their aromatic qualities and play a role in traditional herbal remedies. Terpenoids contribute to the scent of

eucalyptus ''Eucalyptus'' () is a genus of over seven hundred species of flowering trees, shrubs or mallees in the myrtle family, Myrtaceae. Along with several other genera in the tribe Eucalypteae, including '' Corymbia'', they are commonly known as ...

, the flavors of

cinnamon Cinnamon is a spice obtained from the inner bark of several tree species from the genus '' Cinnamomum''. Cinnamon is used mainly as an aromatic condiment and flavouring additive in a wide variety of cuisines, sweet and savoury dishes, breakf ...

cloves Cloves are the aromatic flower buds of a tree in the family Myrtaceae, ''Syzygium aromaticum'' (). They are native to the Maluku Islands (or Moluccas) in Indonesia, and are commonly used as a spice, flavoring or Aroma compound, fragrance in fi ...

, and

ginger Ginger (''Zingiber officinale'') is a flowering plant whose rhizome, ginger root or ginger, is widely used as a spice and a folk medicine. It is a herbaceous perennial which grows annual pseudostems (false stems made of the rolled bases of ...

, the yellow color in

sunflower The common sunflower (''Helianthus annuus'') is a large annual forb of the genus ''Helianthus'' grown as a crop for its edible oily seeds. Apart from cooking oil production, it is also used as livestock forage (as a meal or a silage plant), ...

s, and the red color in

tomato The tomato is the edible berry of the plant ''Solanum lycopersicum'', commonly known as the tomato plant. The species originated in western South America, Mexico, and Central America. The Mexican Nahuatl word gave rise to the Spanish word ...

es. Well-known terpenoids include citral,

menthol Menthol is an organic compound, more specifically a monoterpenoid, made synthetically or obtained from the oils of corn mint, peppermint, or other mints. It is a waxy, clear or white crystalline substance, which is solid at room temperature ...

camphor Camphor () is a waxy, colorless solid with a strong aroma. It is classified as a terpenoid and a cyclic ketone. It is found in the wood of the camphor laurel (''Cinnamomum camphora''), a large evergreen tree found in East Asia; and in the k ...

, salvinorin A in the plant ''

Salvia divinorum ''Salvia divinorum'' (Latin: "sage of the diviners"; also called ska maría pastora, seer's sage, yerba de la pastora, magic mint or simply salvia) is a plant species with transient psychoactive properties when its leaves are consumed by che ...

'', ginkgolide and

bilobalide Bilobalide is a biologically active terpenic tri lactone present in ''Ginkgo biloba''. Chemistry Bilobalide is a main constituent of the terpenoids found in Ginkgo leaves. It also exists in minor amounts in the roots. It is a sesquiterpenoid, i ...

found in ''

Ginkgo biloba ''Ginkgo biloba'', commonly known as ginkgo or gingko ( ), also known as the maidenhair tree, is a species of tree native to China. It is the last living species in the order Ginkgoales, which first appeared over 290 million years ago. Fossils ...

'' and the

cannabinoids Cannabinoids () are several structural classes of compounds found in the cannabis plant primarily and most animal organisms (although insects lack such receptors) or as synthetic compounds. The most notable cannabinoid is the phytocannabinoid tet ...

found in cannabis. The provitamin

beta carotene Beta (, ; uppercase , lowercase , or cursive ; grc, βῆτα, bē̂ta or ell, βήτα, víta) is the second letter of the Greek alphabet. In the system of Greek numerals, it has a value of 2. In Modern Greek, it represents the voiced labio ...

is a terpene derivative called a

carotenoid Carotenoids (), also called tetraterpenoids, are yellow, orange, and red organic pigments that are produced by plants and algae, as well as several bacteria, and fungi. Carotenoids give the characteristic color to pumpkins, carrots, parsnips, ...

. The

steroid A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and ...

s and

sterol Sterol is an organic compound with formula , whose molecule is derived from that of gonane by replacement of a hydrogen atom in position 3 by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the go ...

s in animals are biologically produced from terpenoid precursors. Sometimes terpenoids are added to

protein Proteins are large biomolecules and macromolecules that comprise one or more long chains of amino acid residues. Proteins perform a vast array of functions within organisms, including catalysing metabolic reactions, DNA replication, res ...

s, e.g., to enhance their attachment to the

cell membrane The cell membrane (also known as the plasma membrane (PM) or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane that separates and protects the interior of all cells from the outside environment (t ...

; this is known as isoprenylation. Terpenoids play a role in plant defence as prophylaxis against pathogens and attractants for the predators of herbivores.

Structure and classification

Terpenoids are modified

s, wherein

methyl group In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula . In formulas, the group is often abbreviated as Me. This hydrocarbon group occurs in ma ...

s have been moved or removed, or

oxygen Oxygen is the chemical element with the symbol O and atomic number 8. It is a member of the chalcogen group in the periodic table, a highly reactive nonmetal, and an oxidizing agent that readily forms oxides with most elements ...

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

units that comprise the parent terpene: Terpenoids can also be classified according to the type and number of cyclic structures they contain: linear, acyclic, monocyclic, bicyclic, tricyclic, tetracyclic, pentacyclic, or macrocyclic. The Salkowski test can be used to identify the presence of terpenoids. File:Taxol.svg,

Paclitaxel Paclitaxel (PTX), sold under the brand name Taxol among others, is a chemotherapy medication used to treat a number of types of cancer. This includes ovarian cancer, esophageal cancer, breast cancer, lung cancer, Kaposi's sarcoma, cervical ca ...

is a diterpenoid anticancer drug. File:Terpineol alpha.svg,

Terpineol Terpineol is any of four isomeric monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol. Terpineols have been isolated from a variety of sources such as cardamom, cajuput oil ...

s are monoterpenoids. File:(S)-Humulone.svg, Humulones are classified as sesquiterpenoids. File:All-trans-Retinol2.svg,

Retinol Retinol, also called vitamin A1, is a fat-soluble vitamin in the vitamin A family found in food and used as a dietary supplement. As a supplement it is used to treat and prevent vitamin A deficiency, especially that which results in xeroph ...

is a diterpenoid. File:Beta-thujaplicin.png, Hinokitiol is a monoterpenoid, a tropolone derivative. File:Limonin.svg, Limonin, a common limonoid, is a triterpenoid. File:Geosmin_Structural_Formulae.svg,

Geosmin Geosmin ( ) is an irregular sesquiterpenoid, produced from the universal sesquiterpene precursor farnesyl pyrophosphate (also known as farnesyl diphosphate), in a two-step -dependent reaction. Geosmin, along with the irregular monoterpene 2-met ...

is a sesquiterpenoid.

Biosynthesis

Terpenoids, at least those containing an alcohol functional group, often arise by hydrolysis of carbocationic intermediates produced from geranyl pyrophosphate. Analogously hydrolysis of intermediates from

farnesyl pyrophosphate Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is an intermediate in the biosynthesis of terpenes and terpenoids such as sterols and carotenoids. It is also used in the synthesis of CoQ (part of the electron transport c ...

gives sesquiterpenoids, and hydrolysis of intermediates from

geranylgeranyl pyrophosphate Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of diterpenes and di terpenoids. It is also the precursor to carotenoids, gibberellins, tocopherols, and chlorophylls. It is also a precursor to geranylgeranylated proteins, wh ...

gives

diterpenoid Diterpenes are a class of chemical compounds composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being ...

s, etc.

References

External links

IUPAC definition of terpenoids
{{Authority control Plant communication cs:Izoprenoidy es:Terpenoides it:Terpeni

Structure and classification

Biosynthesis

See also

References

External links