Bergamotenes are a group of isomeric chemical compounds with the molecular formula C₁₅H₂₄. The bergamotenes are found in a variety of plants, particularly in their essential oils. There are two structural isomers, α-bergamotene and β-bergamotene, which differ only by the location of a

double bond In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betwee ...

. Both of these isomers have

stereoisomer In stereochemistry, stereoisomerism, or spatial isomerism, is a form of isomerism in which molecules have the same molecular formula and sequence of bonded atoms (constitution), but differ in the three-dimensional orientations of their atoms in ...

s, the most common of which are known as the ''

cis Cis or cis- may refer to: Places * Cis, Trentino, in Italy * In Poland: ** Cis, Świętokrzyskie Voivodeship, south-central ** Cis, Warmian-Masurian Voivodeship, north Math, science and biology * cis (mathematics) (cis(''θ'')), a trigonome ...

'' and ''

trans Trans- is a Latin prefix meaning "across", "beyond", or "on the other side of". Used alone, trans may refer to: Arts, entertainment, and media * Trans (festival), a former festival in Belfast, Northern Ireland, United Kingdom * ''Trans'' (fil ...

''-isomers (or endo- and exo-isomers). α-Bergamotene is found in the oils of carrot, bergamot,

lime Lime commonly refers to: * Lime (fruit), a green citrus fruit * Lime (material), inorganic materials containing calcium, usually calcium oxide or calcium hydroxide * Lime (color), a color between yellow and green Lime may also refer to: Botany ...

citron The citron (''Citrus medica''), historically cedrate, is a large fragrant citrus fruit with a thick rind. It is said to resemble a 'huge, rough lemon'. It is one of the original citrus fruits from which all other citrus types developed throu ...

cottonseed Cottonseed is the seed of the cotton plant. Composition The mature seeds are brown ovoids weighing about a tenth of a gram. By weight, they are 60% cotyledon, 32% coat and 8% embryonic root and shoot. These are 20% protein, 20% oil and 3.5% sta ...

, and

kumquat Kumquats (; zh, 金桔), or cumquats in Australian English, are a group of small fruit-bearing trees in the flowering plant family Rutaceae. Their taxonomy is disputed. They were previously classified as forming the now-historical genus ''For ...

Pheromones

The bergamotenes are pheromones for some insects. For example, β-''trans''-bergamotene is a pheromone for the wasp '' Melittobia digitata''. Plants can defend themselves against attack by herbivorous insects by producing pheromones such as bergamotenes that attract predators of those herbivores. In a more complex relationship, the tobacco plant ''

Nicotiana attenuata ''Nicotiana attenuata'' is a species of wild tobacco known by the common name coyote tobacco. It is native to western North America from British Columbia to Texas and northern Mexico, where it grows in many types of habitat. It is a glandular a ...

'' emits α-''trans''-bergamotene from its flowers at night to attract the tobacco hawk moth (''Manduca sexta'') as a pollinator; however, during the day the leaves produce α-''trans''-bergamotene to lure predatory insects to feed on any larvae and eggs that the pollinator may have produced.

Biosynthesis

All the bergamotenes are

biosynthesized Biosynthesis is a multi-step, enzyme- catalyzed process where substrates are converted into more complex products in living organisms. In biosynthesis, simple compounds are modified, converted into other compounds, or joined to form macromolecules ...

from farnesyl pyrophosphate via a variety of enzymes including exo-alpha-bergamotene synthase, (+)-endo-beta-bergamotene synthase, (-)-endo-alpha-bergamotene synthase, and others. Bergamotenes, in turn, are intermediates in the biosynthesis of more complex chemical compounds. For example, β-''trans''-bergamotene is a precursor in the biosynthesis of

fumagillin Fumagillin is a complex biomolecule and used as an antimicrobial agent. It was isolated in 1949 from the microbial organism ''Aspergillus fumigatus''. Uses In animals It was originally used against microsporidian parasites ''Nosema apis'' infecti ...

, ovalicin, and related antibiotics.

References

{{reflist Sesquiterpenes