Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n. 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), etc. A well known monoterpene is alpha-pinene, a major component of turpentine.
Caryophyllene, more formally (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene and α-humulene, a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.
Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds, two of them being triply substituted and one being doubly substituted. It was first found in the essential oils of Humulus lupulus (hops), from which it derives its name. Humulene is an isomer of β-caryophyllene, and the two are often found together as a mixture in many aromatic plants.
Zingiberene is a monocyclic sesquiterpene that is the predominant constituent of the oil of ginger, from which it gets its name. It can contribute up to 30% of the essential oils in ginger rhizomes. This is the compound that gives ginger its distinct flavoring.
Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is an intermediate in both the mevalonate and non-mevalonate pathways used by organisms in the biosynthesis of terpenes, terpenoids, and sterols.
Baldwin's rules in organic chemistry are a series of guidelines outlining the relative favorabilities of ring closure reactions in alicyclic compounds. They were first proposed by Jack Baldwin in 1976.
Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be acyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids.
Carrot seed oil is the essential oil extract of the seed from the carrot plant Daucus carota. The oil has a woody, earthy sweet smell and is yellow or amber-coloured to pale orange-brown in appearance. The pharmocologically active constituents of carrot seed extract are three flavones: luteolin, luteolin 3'-O-beta-D-glucopyranoside, and luteolin 4'-O-beta-D-glucopyranoside. Rather than the extract the distilled (ethereal) oil is used in perfumery and food aromatization. The main constituent of this oil is carotol.
In enzymology, a (+)-delta-cadinene synthase is an enzyme that catalyzes the chemical reaction
Squalene synthase (SQS) or farnesyl-diphosphate:farnesyl-diphosphate farnesyl transferase is an enzyme localized to the membrane of the endoplasmic reticulum. SQS participates in the isoprenoid biosynthetic pathway, catalyzing a two-step reaction in which two identical molecules of farnesyl pyrophosphate (FPP) are converted into squalene, with the consumption of NADPH. Catalysis by SQS is the first committed step in sterol synthesis, since the squalene produced is converted exclusively into various sterols, such as cholesterol, via a complex, multi-step pathway. SQS belongs to squalene/phytoene synthase family of proteins.
In enzymology, an aristolochene synthase is an enzyme that catalyzes the chemical reaction
In enzymology, a pentalenene synthase is an enzyme that catalyzes the chemical reaction
In enzymology, a vetispiradiene synthase is an enzyme of Egyptian henbane that catalyzes the following chemical reaction:
In enzymology, a geranyltranstransferase is an enzyme that catalyzes the chemical reaction
Damascenones are a series of closely related chemical compounds that are components of a variety of essential oils. The damascenones belong to a family of chemicals known as rose ketones, which also includes damascones and ionones. beta-Damascenone is a major contributor to the aroma of roses, despite its very low concentration, and is an important fragrance chemical used in perfumery.
Botrydial is a phytotoxic sesquiterpene metabolite secreted by the fungus Botrytis cinerea. Botrydial was first isolated and described in 1974. Botrytis Cinerea is the causal agent of gray mold disease and is known to attack a wide range of plants producing leaf-spot diseases and mildews on lettuces and tomatoes as well as rotting berries. For this reason, botrydial, as well as other Botrytis Cinerea originated sesquiterpene metabolites, represent an economically important disease for ornamental and agriculturally important crops. From all the metabolites produced by this fungus, Botrydial exhibits the highest phytotoxic activity.
Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid, both of which 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.
Thujopsene is a natural chemical compound, classified as a sesquiterpene, with the molecular formula C15H24.
(+)-epicubenol synthase (EC 4.2.3.64, farnesyl pyrophosphate cyclase) is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase ((+)-epicubenol-forming). This enzyme catalyses the following chemical reaction
Arglabin is a sesquiterpene lactone belonging to the guaianolide subclass bearing a 5,7,5-tricyclic ring system which is known to inhibit farnesyl transferase. It is characterized by an epoxide on the cycloheptane as well as an exocyclic methylene group that is conjugated with the carbonyl of the lactone. Arglabin is extracted from Artemisia glabella, a species of wormwood, found in the Karaganda Region of Kazakhstan. Arglabin and its derivatives are biologically active and demonstrate promising antitumor activity and cytoxocity against varying tumor cell lines.
