Bergamotenes are a group of chemical compounds with the molecular formula C15H24. The bergamotenes are found in a variety of plants, particularly in their .
There are two structural isomers, α-bergamotene and β-bergamotene, which differ only by the location of a double bond. Both of these isomers have , the most common of which are known as the cis and trans-isomers (or endo- and exo-isomers).
α-Bergamotene is found in the oils of carrot, Bergamot orange, lime, citron, cottonseed, and kumquat.
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 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
biosynthesis 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,
ovalicin, and related antibiotics.
