MetaCyc Pathway: bergamotene biosynthesis II
Inferred from experiment

Enzyme View:

Pathway diagram: bergamotene biosynthesis II

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Superclasses: BiosynthesisSecondary Metabolites BiosynthesisTerpenoids BiosynthesisSesquiterpenoids BiosynthesisBergamotene Biosynthesis

Some taxa known to possess this pathway include : Betula, Betula pubescens, Solanum habrochaites

Expected Taxonomic Range: Viridiplantae

Bergamotenes are sesquiterpenoids that are components of volatile oils from a number of plants. They function as insect repellents in some plants, although they may also function as attractants for certain organisms. There are several isomers of bergamotene, including (-)-endo-α-bergamotene, (+)-endo-β-bergamotene, (-)-exo-α-bergamotene and (+)-exo-β-bergamotene.

(-)-exo-α-bergamotene and (+)-exo-β-bergamotene have been identified as the active compounds of the sex attractant of male Melittobia digitata wasps [Cĵnsoli02].

In members of Solanaceae bergamotenes play a role in defense against insects [Sallaud09]. The domesticated Solanum lycopersicum plant does not produce bergamotenes, but its wild relative Solanum habrochaites does [vanDer00]. Many plants have lost some of their inherent survival traits during domestication.

This pathway depicts the steps of bergamotene biosynthesis in the wild tomato Solanum habrochaites. The enzyme santalene and bergamontene synthase, which is encoded by the SBS gene, acts specifically on (2Z,6Z)-farnesyl diphosphate to produce three major terpenes (-)-endo-α-bergamotene, (+)-endo-β-bergamotene and (+)-α-santalene [Sallaud09].

These three compounds, along with their epoxy derivatives, have also been isolated from Birch bark Betula pubescens [Abyshev07].

Variants: bergamotene biosynthesis I

Created 18-May-2009 by Pujar A, Boyce Thompson Institute
Revised 27-May-2011 by Caspi R, SRI International


Abyshev07: Abyshev, A. Z, Agaev, E.M, Guseinov, A.B (2007). "Studies of the chemical composition of birch bark extracts (Cortex betula) from the Betulaceae family." Pharmaceutical Chemistry Journal, 41, 419-423.

Cĵnsoli02: Cĵnsoli FL, Williams HJ, Vinson SB, Matthews RW, Cooperband MF (2002). "Trans-bergamotenes-male pheromone of the ectoparasitoid Melittobia digitata." J Chem Ecol 28(8);1675-89. PMID: 12371819

Sallaud09: Sallaud C, Rontein D, Onillon S, Jabes F, Duffe P, Giacalone C, Thoraval S, Escoffier C, Herbette G, Leonhardt N, Causse M, Tissier A (2009). "A novel pathway for sesquiterpene biosynthesis from Z,Z-farnesyl pyrophosphate in the wild tomato Solanum habrochaites." Plant Cell 21(1);301-17. PMID: 19155349

vanDer00: van Der Hoeven RS, Monforte AJ, Breeden D, Tanksley SD, Steffens JC (2000). "Genetic control and evolution of sesquiterpene biosynthesis in Lycopersicon esculentum and L. hirsutum." Plant Cell 12(11);2283-94. PMID: 11090225

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
Page generated by Pathway Tools version 19.5 (software by SRI International) on Thu May 5, 2016, biocyc13.