Bergamotenes are a group of
isomeric chemical compounds with the molecular formula C
15H
24. 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