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

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.

[1] "Metabocard for alpha-Bergamotene (HMDB0036678)". Human Metabolome Database.

[2] 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.

[3] "Semiochemical - beta-trans-bergamotene". pherobase.com.

[4] 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.

[5] 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.

[6] 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.

[7] "Bergamotene—alluring and lethal for Manduca sexta". Max-Planck-Gesellschaft. April 24, 2017. Retrieved August 16, 2019.

[Cane-8] 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.

[9] 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.

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