Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. Terpenes are further classified by the number of carbons: monoterpenes (C10), sesquiterpenes (C15), diterpenes (C20), as examples. The terpene alpha-pinene, is a major component of the common solvent, turpentine.
Pharmacognosy is the study of crude drugs obtained from medicinal plants, animals, fungi, and other natural sources. The American Society of Pharmacognosy defines pharmacognosy as "the study of the physical, chemical, biochemical, and biological properties of drugs, drug substances, or potential drugs or drug substances of natural origin as well as the search for new drugs from natural sources".
Diterpenes are a class of terpenes 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 a primary intermediate. Diterpenes form the basis for biologically important compounds such as retinol, retinal, and phytol. They are known to be antimicrobial and anti-inflammatory.
Phytochemistry is the study of phytochemicals, which are chemicals derived from plants. Phytochemists strive to describe the structures of the large number of secondary metabolites found in plants, the functions of these compounds in human and plant biology, and the biosynthesis of these compounds. Plants synthesize phytochemicals for many reasons, including to protect themselves against insect attacks and plant diseases. The compounds found in plants are of many kinds, but most can be grouped into four major biosynthetic classes: alkaloids, phenylpropanoids, polyketides, and terpenoids.
Linalool refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. Linalool has multiple commercial applications, the majority of which are based on its pleasant scent. A colorless oil, linalool is classified as an acyclic monoterpenoid. In plants, it is a metabolite, a volatile oil component, an antimicrobial agent, and an aroma compound. Linalool has uses in manufacturing of soaps, fragrances, food additives as flavors, household products, and insecticides. Esters of linalool are referred to as linalyl, e.g. linalyl pyrophosphate, an isomer of geranyl pyrophosphate.
Myrcene, or β-myrcene, is a monoterpene. A colorless oil, it occurs widely in essential oils. It is produced mainly semi-synthetically from Myrcia, from which it gets its name. It is an intermediate in the production of several fragrances. α-Myrcene is the name for the isomer 2-methyl-6-methylene-1,7-octadiene, which has not been found in nature.
Geranyl pyrophosphate (GPP), also known as geranyl diphosphate (GDP), is the pyrophosphate ester of the terpenoid geraniol. Its salts are colorless. It is a precursor to many natural products.
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, as well as dehydrodolichol diphosphate.
Geranylgeranyl pyrophosphate is an intermediate in the biosynthesis of diterpenes and diterpenoids. It is also the precursor to carotenoids, gibberellins, tocopherols, and chlorophylls.
Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids.
Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen functionality or missing a methyl group, are called monoterpenoids. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries.
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, pine oil, and petitgrain oil. Four isomers exist: α-, β-, γ-terpineol, and terpinen-4-ol. β- and γ-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with α-terpineol as the major constituent.
In enzymology, bornyl diphosphate synthase (BPPS) (EC 5.5.1.8) is an enzyme that catalyzes the chemical reaction
Absinthin is a naturally produced triterpene lactone from the plant Artemisia absinthium (Wormwood). It constitutes one of the most bitter chemical agents responsible for absinthe's distinct taste. The compound shows biological activity and has shown promise as an anti-inflammatory agent, and should not to be confused with thujone, a neurotoxin also found in Artemisia absinthium.
Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid. Both are sesquiterpenes (C15) found in the wood of true firs of the genus Abies. They occur naturally as part of a mixture of sesquiterpenes based upon the bisabolane scaffold. Sesquiterpenes of this family are known as insect juvenile hormone analogues (IJHA) because of their ability to mimic juvenile activity in order to stifle insect reproduction and growth. These compounds play important roles in conifers as the second line of defense against insect induced trauma and fungal pathogens.
Abietane is a diterpene that forms the structural basis for a variety of natural chemical compounds such as abietic acid, carnosic acid, and ferruginol which are collectively known as abietanes or abietane diterpenes.
Levopimaric acid is an abietane-type of diterpene resin acid. It is a major constituent of pine oleoresin with the chemical formula of C20H30O2. In general, the abietene types of diterpene resin acid have various biological activities, such as antibacterial, cardiovascular and antioxidant. Levopimaric acid accounts for about 18 to 25% of pine oleoresin. The production of oleoresin by conifer species is an important component of the defense response against insect attack and fungal pathogen infection.
Sugiol is a phenolic abietane derivative of ferruginol and can be used as a biomarker for specific families of conifers. The presence of sugiol can be used to identify the Cupressaceae s.1., podocarpaceae, and Araucaraiaceae families of conifers. The polar terpenoids are among the most resistant molecules to degradation besides n-alkanes and fatty acids, affording them high viability as biomarkers due to their longevity in the sedimentary record. Significant amounts of sugiol has been detected in fossil wood dated to the Eocene and Miocene periods, as well as a sample of Protopodocarpoxylon dated to the middle Jurassic.
Avarol is a hydroquinone first isolated from the Mediterranean marine sponge Dysidea avara 1974 Avarol represented the first sesquiterpenoid with a rearranged drimane skeleton and its structure was established by standard analytical methods, chemical degradation and later by stereocontrolled synthesis. Intrigued by the wide range of biological activities of this metabolite, Avarol has inspired the development of many synthetic derivatives and the study of their applications.
Cannabis (/ˈkænəbɪs/) is commonly known as marijuana or hemp and has two known strains: Cannabis sativa and Cannabis indica, both of which produce chemicals to deter herbivory. The chemical composition includes specialized terpenes and cannabinoids, mainly tetrahydrocannabinol (THC), and cannabidiol (CBD). These substances play a role in defending the plant from pathogens including insects, fungi, viruses and bacteria. THC and CBD are stored mostly in the trichomes of the plant, and can cause psychological and physical impairment in the user, via the endocannabinoid system and unique receptors. THC increases dopamine levels in the brain, which attributes to the euphoric and relaxed feelings cannabis provides. As THC is a secondary metabolite, it poses no known effects towards plant development, growth, and reproduction. However, some studies show secondary metabolites such as cannabinoids, flavonoids, and terpenes are used as defense mechanisms against biotic and abiotic environmental stressors.
Paclitaxel is a diterpenoid anticancer drug.
Terpineols are monoterpenoids.
Humulones are classified as sesquiterpenoids.
Retinol is a diterpenoid.
Hinokitiol is a monoterpenoid, a tropolone derivative.
Geosmin is a sesquiterpenoid.
