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).
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]
^"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.
^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. PMC1347987. 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. doi:10.1016/j.cub.2017.03.017. PMID 28434859.
^"Bergamotene—alluring and lethal for Manduca sexta". Max-Planck-Gesellschaft. April 24, 2017. Retrieved August 16, 2019.
^ abCane, 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.
August 25, 2023
bergamotene, confused, with, bergamottin, group, isomeric, chemical, compounds, with, molecular, formula, c15h24, bergamotenes, found, variety, plants, particularly, their, essential, oils, bergamotene, trans, bergamoteneβ, bergamotene, trans, bergamotenenames. Not to 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 Bergamotenes a cis bergamotene a trans bergamoteneb cis bergamotene b trans bergamoteneNamesIUPAC names a 2 6 Dimethyl 6 4 methylpent 3 enyl bicyclo 3 1 1 hept 2 ene b 6 Methyl 2 methylidene 6 4 methylpent 3 en 1 yl bicyclo 3 1 1 heptaneIdentifiersCAS Number a 17699 05 7 a trans 13474 59 4 a cis 23971 87 1 b 6895 56 3 b trans 15438 94 5 b cis 15438 93 43D model JSmol a Interactive image b b Interactive imageChEBI a trans CHEBI 62756 a cis CHEBI 61679 b cis CHEBI 61678KEGG a trans C20811 a cis C19735 b cis C19737PubChem CID a trans 6429302 a cis 6429303 b trans 12300073 b cis 12300069UNII a trans 599TK2712C a trans Y b 2H330CKD1Z YCompTox Dashboard EPA a trans DTXSID901017570SMILES a CC1 CCC2CC1C2 C CCC C C C b b CC CCCC1 C2CCC C C1C2 C CPropertiesChemical formula C 15H 24Molar mass 204 357 g mol 1Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references There are two structural isomers a bergamotene and b 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 a Bergamotene is found in the oils of carrot bergamot lime citron cottonseed and kumquat 1 2 Pheromones EditThe bergamotenes are pheromones for some insects For example b 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 a 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 a trans bergamotene to lure predatory insects to feed on any larvae and eggs that the pollinator may have produced 6 7 Biosynthesis EditAll 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 b trans bergamotene is a precursor in the biosynthesis of fumagillin ovalicin and related antibiotics 8 9 References Edit 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 Kugler Anke McGale Erica Haverkamp Alexander Knaden Markus Guo Han Beran Franziska Yon Felipe Li Ran Lackus Nathalie Kollner Tobias G Bing Julia Schuman Meredith C Hansson Bill S Kessler Danny Baldwin Ian T Xu Shuqing 2017 Tissue Specific Emission of E a Bergamotene Helps Resolve the Dilemma when Pollinators Are Also Herbivores Current Biology 27 9 1336 1341 doi 10 1016 j cub 2017 03 017 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 b trans bergamotene Tetrahedron Letters 28 52 6545 6548 doi 10 1016 S0040 4039 00 96909 0 Retrieved from https en wikipedia org w index php title Bergamotene amp oldid 1042894079, wikipedia, wiki, book, books, library,
