Bergamotene

Bergamotenes
α-cis-bergamotene	α-trans-bergamotene
β-cis-bergamotene	β-trans-bergamotene
Names
	IUPAC names (α): 2,6-Dimethyl-6-(4-methylpent-3-enyl)bicyclo[3.1.1]hept-2-ene; (β): 6-Methyl-2-methylidene-6-(4-methylpent-3-en-1-yl)bicyclo[3.1.1]heptane
Identifiers
CAS Number	(α): 17699-05-7; (α-trans): 13474-59-4; (α-cis): 23971-87-1; (β): 6895-56-3; (β-trans): 15438-94-5; (β-cis): 15438-93-4;
3D model (JSmol)	(α): Interactive image; (β) (β): Interactive image;
ChEBI	(α-trans): CHEBI:62756; (α-cis): CHEBI:61679; (β-cis): CHEBI:61678;
ChemSpider	(α-trans): 78115;
KEGG	(α-trans): C20811; (α-cis): C19735; (β-cis): C19737;
PubChem CID	(α-trans): 6429302; (α-cis): 6429303; (β-trans): 12300073; (β-cis): 12300069;
UNII	(α-trans): 599TK2712C (α-trans) ; (β): 2H330CKD1Z ;
CompTox Dashboard (EPA)	(α-trans): DTXSID901017570;
	SMILES (α): CC1=CCC2CC1C2(C)CCC=C(C)C; (β) (β): CC(=CCCC1(C2CCC(=C)C1C2)C)C;
Properties
Chemical formula	C15H24
Molar mass	204.357 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

The printable version is no longer supported and may have rendering errors. Please update your browser bookmarks and please use the default browser print function instead.

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]

References

^ "Metabocard for alpha-Bergamotene (HMDB0036678)". Human Metabolome Database.
^ Koyasako, A.; Bernhard, R. A. (1983). "Volatile Constituents of the Essential Oil of Kumquat". Journal of Food Science. 48 (6): 1807–1812. doi:10.1111/j.1365-2621.1983.tb05090.x.
^ "Semiochemical - beta-trans-bergamotene". pherobase.com.
^ Kessler, A.; Baldwin, I. T. (2001). "Defensive Function of Herbivore-Induced Plant Volatile Emissions in Nature". Science. 291 (5511): 2141–2144. Bibcode:2001Sci...291.2141K. doi:10.1126/science.291.5511.2141. PMID 11251117.
^ Schnee, C.; Kollner, T. G.; Held, M.; Turlings, T. C. J.; Gershenzon, J.; Degenhardt, J. (2006). "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. Bibcode:2006PNAS..103.1129S. doi:10.1073/pnas.0508027103. PMC 1347987. PMID 16418295.
^ 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 (2017). "Tissue-Specific Emission of (E)-α-Bergamotene Helps Resolve the Dilemma when Pollinators Are Also Herbivores". Current Biology. 27 (9): 1336–1341. Bibcode:2017CBio...27.1336Z. doi:10.1016/j.cub.2017.03.017. hdl:11858/00-001M-0000-002D-1838-C. PMID 28434859.
^ "Bergamotene—alluring and lethal for Manduca sexta". Max-Planck-Gesellschaft. April 24, 2017. Retrieved August 16, 2019.
^ ^a ^b Cane, David E.; McIlwaine, Douglas B.; Harrison, Paul H. M. (1989). "Bergamotene biosynthesis and the enzymic cyclization of farnesyl pyrophosphate". Journal of the American Chemical Society. 111 (3): 1152–1153. doi:10.1021/ja00185a068.
^ Cane, David E.; McIlwaine, Douglas B. (1987). "The biosynthesis of ovalicin from β-trans-bergamotene". Tetrahedron Letters. 28 (52): 6545–6548. doi:10.1016/S0040-4039(00)96909-0.