Bergamotene Explained

Bergamotene should not be confused with bergamottin.

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. Both of these isomers have stereoisomers, 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, lime, citron, cottonseed, and kumquat.^{[1] [2]}

Pheromones

The bergamotenes are pheromones for some insects. For example, β-trans-bergamotene is a pheromone for the wasp Melittobia digitata.^[3] Plants can defend themselves against attack by herbivorous insects by producing pheromones such as bergamotenes that attract predators of those herbivores.^{[4] [5]} 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.^{[6] [7]}

Biosynthesis

All the bergamotenes are biosynthesized from farnesyl pyrophosphate^[8] 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.^{[8] [9]}

Notes and References

1. Web site: Metabocard for alpha-Bergamotene (HMDB0036678) . Human Metabolome Database .
2. 10.1111/j.1365-2621.1983.tb05090.x . Volatile Constituents of the Essential Oil of Kumquat . Journal of Food Science . 48 . 6 . 1807–1812 . 1983 . Koyasako . A. . Bernhard . R. A. .
3. Web site: Semiochemical - beta-trans-bergamotene . pherobase.com .
4. 10.1126/science.291.5511.2141 . 11251117 . Defensive Function of Herbivore-Induced Plant Volatile Emissions in Nature . Science . 291 . 5511 . 2141–2144 . 2001 . Kessler . A. . Baldwin . I. T. . 2001Sci...291.2141K .
5. 10.1073/pnas.0508027103 . 16418295 . 1347987 . The products of a single maize sesquiterpene synthase form a volatile defense signal that attracts natural enemies of maize herbivores . Proceedings of the National Academy of Sciences . 103 . 4 . 1129–1134 . 2006 . Schnee . C. . Kollner . T. G. . Held . M. . Turlings . T. C. J. . Gershenzon . J. . Degenhardt . J. . 2006PNAS..103.1129S . free .
6. 10.1016/j.cub.2017.03.017 . 28434859 . Tissue-Specific Emission of (E)-α-Bergamotene Helps Resolve the Dilemma when Pollinators Are Also Herbivores . Current Biology . 27 . 9 . 1336–1341 . 2017 . Zhou . Wenwu . Kügler . Anke . McGale . Erica . Haverkamp . Alexander . Knaden . Markus . Guo . Han . Beran . Franziska . Yon . Felipe . Li . Ran . Lackus . Nathalie . Köllner . Tobias G. . Bing . Julia . Schuman . Meredith C. . Hansson . Bill S. . Kessler . Danny . Baldwin . Ian T. . Xu . Shuqing . free . 11858/00-001M-0000-002D-1838-C . free .
7. Web site: Bergamotene—alluring and lethal for Manduca sexta . . April 24, 2017 . August 16, 2019 .
8. 10.1021/ja00185a068 . Bergamotene biosynthesis and the enzymic cyclization of farnesyl pyrophosphate . Journal of the American Chemical Society . 111 . 3 . 1152–1153 . 1989 . Cane . David E. . McIlwaine . Douglas B. . Harrison . Paul H. M. .
9. 10.1016/S0040-4039(00)96909-0 . The biosynthesis of ovalicin from β-trans-bergamotene . Tetrahedron Letters . 28 . 52 . 6545–6548 . 1987 . Cane . David E. . McIlwaine . Douglas B. .