Bergamotene

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Bergamotenes
A-cis-bergamotene.svg
α-cis-bergamotene
A-trans-bergamotene.svg
α-trans-bergamotene
B-cis-bergamotene.svg
β-cis-bergamotene
B-trans-bergamotene.svg
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
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • (α):CC1=CCC2CC1C2(C)CCC=C(C)C
  • (β) (β):CC(=CCCC1(C2CCC(=C)C1C2)C)C
Properties
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).

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.

Contents

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]

Related Research Articles

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Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. In plants, terpenes and terpenoids are important mediators of ecological interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.

<span class="mw-page-title-main">Nepetalactone</span> Chemical compound

Nepetalactone is a name for multiple iridoid analog stereoisomers. Nepetalactones are produced by Nepeta cataria (catnip) and many other plants belonging to the genus Nepeta, in which they protect these plants from herbivorous insects by functioning as insect repellents. They are also produced by many aphids, in which they are sex pheromones. Nepetalactones are cat attractants, and cause the behavioral effects that catnip induces in domestic cats. However, they affect visibly only about two thirds of adult cats. They produce similar behavioral effects in many other felids, especially in lions and jaguars. In 1941, the research group of Samuel M. McElvain was the first to determine the structures of nepetalactones and several related compounds.

Juvenile hormones (JHs) are a group of acyclic sesquiterpenoids that regulate many aspects of insect physiology. The first discovery of a JH was by Vincent Wigglesworth. JHs regulate development, reproduction, diapause, and polyphenisms.

<span class="mw-page-title-main">Fenchol</span> Chemical compound

Fenchol or 1,3,3-trimethyl-2-norbornanol is a monoterpenoid and an isomer of borneol. It is a colorless or white solid. It occurs widely in nature.

<span class="mw-page-title-main">Terpineol</span> Chemical compound

Terpineol is any of four isomeric monoterpenoids. Terpenoids are terpene that are modified by the addition of a functional group, in this case, an alcohol. Terpineols have been isolated from a variety of sources such as cardamom, cajuput oil, pine oil, and petitgrain oil. Four isomers exist: α-, β-, γ-terpineol, and terpinen-4-ol. β- and γ-terpineol differ only by the location of the double bond. Terpineol is usually a mixture of these isomers with α-terpineol as the major constituent.

The enzyme aristolochene synthase catalyzes the chemical reaction

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<span class="mw-page-title-main">Juvabione</span> Chemical compound

Juvabione, historically known as the paper factor, is the methyl ester of todomatuic acid. Both are sesquiterpenes (C15) found in the wood of true firs of the genus Abies. They occur naturally as part of a mixture of sesquiterpenes based upon the bisabolane scaffold. Sesquiterpenes of this family are known as insect juvenile hormone analogues (IJHA) because of their ability to mimic juvenile activity in order to stifle insect reproduction and growth. These compounds play important roles in conifers as the second line of defense against insect induced trauma and fungal pathogens.

<i>Nicotiana attenuata</i> Species of flowering plant

Nicotiana attenuata is a species of wild tobacco known by the common name coyote tobacco. It is native to western North America from British Columbia to Texas and northern Mexico, where it grows in many types of habitat. It is a glandular and sparsely hairy annual herb exceeding a meter in maximum height. The leaf blades may be 10 centimetres (4 in) long, the lower ones oval and the upper narrower in shape, and are borne on petioles. The inflorescence bears several flowers with pinkish or greenish white tubular throats 2 to 3 centimetres long, their bases enclosed in pointed sepals. The flower face has five mostly white lobes. The fruit is a capsule about 1 centimetre long.

<span class="mw-page-title-main">Bisabolene</span> Chemical compound

Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Bisabolenes are produced from farnesyl pyrophosphate (FPP) and are present in the essential oils of bisabol, and of a wide variety of other plants including cubeb, lemon, and oregano. Various derivates also function as pheromones in different insects, such as stink bugs and fruit flies. Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear.

β-Farnesene synthase (EC 4.2.3.47, farnesene synthase, terpene synthase 10, terpene synthase 10-B73, TPS10) is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase ((E)-β-farnesene-forming). This enzyme catalyses the following chemical reaction

(+)-α-Santalene synthase is an enzyme with systematic name (2Z,6Z)-farnesyl diphosphate lyase . This enzyme catalyses the following chemical reaction

(+)-endo-β-Bergamotene synthase (SBS) is an enzyme with systematic name (2Z,6Z)-farnesyl diphosphate lyase . This enzyme catalyses the following chemical reaction

(+)-endo-α-Bergamotene synthase (SBS) is an enzyme with systematic name (2Z,6Z)-farnesyl diphosphate lyase . This enzyme catalyses the following chemical reaction

exo-α-Bergamotene synthase (EC 4.2.3.81, trans-α-bergamotene synthase, LaBERS (gene)) is an enzyme with systematic name (2E,6E)-farnesyl diphosphate lyase (cyclizing, (–)-exo-α-bergamotene-forming). This enzyme catalyses the following chemical reaction:

(−)-α-Cuprenene synthase is an enzyme with systematic name (−)-α -cuprenene hydrolase . This enzyme catalyses the following chemical reaction

(−)-α-Pinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (−)-α-pinene-forming]. This enzyme catalyses the following chemical reaction

(−)-β-Pinene synthase (EC 4.2.3.120, β-geraniolene synthase, (−)-(1S,5S)-pinene synthase, geranyldiphosphate diphosphate lyase (pinene forming)) is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (−)-β-pinene-forming]. This enzyme catalyses the following chemical reaction

(+)-α-pinene synthase is an enzyme with systematic name geranyl-diphosphate diphosphate-lyase [cyclizing, (+)-α-pinene-forming]. This enzyme catalyses the following chemical reaction

β-Sesquiphellandrene synthase is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

References

  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.
  8. 1 2 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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