Multistriatin

Last updated
Multistriatin
Multistriatin.svg
Names
IUPAC name
5-ethyl-2,4-dimethyl-6,8-dioxabicyclo[3.2.1]octane
Other names
(1S,2R,4S,5R)-5-ethyl-2,4-dimethyl-6,8-dioxabicyclo[3.2.1]octane
Identifiers
3D model (JSmol)
PubChem CID
UNII
Properties
C10H18O2
Molar mass 170.25 g·mol−1
Density 0.959 g/mL
Boiling point 207.1 °C (404.8 °F; 480.2 K)
Hazards
Flash point 74.9 °C (166.8 °F; 348.0 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Multistriatin is a pheromone of the elm bark beetle. It is a volatile compound released by a virgin female beetle when she has found a good source of food, such as an elm tree. [1]

Pheromone secreted or excreted chemical factor that triggers a social response in members of the same species

A pheromone is a secreted or excreted chemical factor that triggers a social response in members of the same species. Pheromones are chemicals capable of acting like hormones outside the body of the secreting individual, to impact the behavior of the receiving individuals. There are alarm pheromones, food trail pheromones, sex pheromones, and many others that affect behavior or physiology. Pheromones are used from basic unicellular prokaryotes to complex multicellular eukaryotes. Their use among insects has been particularly well documented. In addition, some vertebrates, plants and ciliates communicate by using pheromones.

Contents

Potential applications

Males beetles, which carry the fungus which causes Dutch elm disease, are attracted to the pheromone. Hence multistriatin could be used to trap beetles and so prevent the spread of the disease. [1]

Dutch elm disease plant disease caused by Ophiostoma ulmi fungus

Dutch elm disease (DED) is caused by a member of the sac fungi (Ascomycota) affecting elm trees, and is spread by elm bark beetles. Although believed to be originally native to Asia, the disease was accidentally introduced into America and Europe, where it has devastated native populations of elms that did not have resistance to the disease. It has also reached New Zealand. The name "Dutch elm disease" refers to its identification in 1921 and later in the Netherlands by Dutch phytopathologists Bea Schwarz and Christine Buisman who both worked with Professor Johanna Westerdijk. The disease affects species in the genera Ulmus and Zelkova, therefore it is not specific to the Dutch elm hybrid.

Stereochemistry

The compound exists in several diastereomic forms, depending on the positions of the methyl groups. [2] Only the natural stereoisomer, α-multistriatin, attracts the elm bark beetles.

Multistriatin stereochemistry.png

Related Research Articles

Bark beetle subfamily of insects

A bark beetle is one of about 220 genera with 6,000 species of beetles in the subfamily Scolytinae. Traditionally, this was considered a distinct family Scolytidae, but is now understood to be very specialized members of the "true weevil" family (Curculionidae). Well-known species are members of the type genus Scolytus, namely the European elm bark beetle S. multistriatus and the large elm bark beetle S. scolytus, which like the American elm bark beetle Hylurgopinus rufipes, transmit Dutch elm disease fungi (Ophiostoma). The mountain pine beetle Dendroctonus ponderosae, southern pine beetle Dendroctonus frontalis, and their near relatives are major pests of conifer forests in North America. A similarly aggressive species in Europe is the spruce ips Ips typographus. A tiny bark beetle, the coffee berry borer, Hypothenemus hampei is a major pest on coffee plantations around the world.

A kairomone is a semiochemical, emitted by an organism, which mediates interspecific interactions in a way that benefits an individual of another species which receives it, and harms the emitter. This "eavesdropping" is often disadvantageous to the producer. The kairomone improves the fitness of the recipient and in this respect differs from an allomone and a synomone. The term is mostly used in the field of entomology. Two main ecological cues are provided by kairomones; they generally either indicate a food source for the receiver, or the presence of a predator, the latter of which is less common or at least less studied.

Aradidae Family of insects

Aradidae bear the appropriate common name, flat bugs, in reference to their (usually) extremely flattened body. With few exceptions, these often cryptic insects are of no economic importance. Common temperate genera include Aradus, Mezira, Neuroctenus, and Aneurus.

<i>Thanasimus formicarius</i> species of beetle

The ant beetle, also known as the European red-bellied clerid, is a medium size insect, rather soft-bodied, with strong mandibles that can tear between the hard sclerotized integument of bark beetles. Larvae and adults are common predators of bark beetles in Europe.

The Chinese Elm cultivar Ulmus parvifolia 'Matthew' is one of three American introductions selected for their cold hardiness.

The Chinese Elm cultivar Ulmus parvifolia 'Milliken' is another American introduction.

The Chinese Elm cultivar Ulmus parvifolia 'Pathfinder' is another development by A. M. Townsend of the USDA National Arboretum registered in 1990.

<i>Ulmus parvifolia</i> Kings Choice

The Chinese Elm cultivar Ulmus parvifolia 'King's Choice' is one of the early American selections best known for its winter hardiness, able to withstand temperatures of -30 deg. Celsius. 'King's Choice' was patented in 1985.

The Chinese Elm cultivar Ulmus parvifolia 'Cork Bark' is a North American clone.

The Chinese Elm cultivar Ulmus parvifolia 'State Fair' was cloned from a tree growing in the grounds of the Oklahoma State Fair, Oklahoma City.

The Chinese Elm cultivar Ulmus parvifolia 'Stone's Dwarf' was commercially released in the USA in 1978.

The Chinese Elm cultivar Ulmus parvifolia 'The Thinker' was selected by M. Hayman from a tree on the campus of the University of Louisville, Kentucky.

The Chinese Elm cultivar Ulmus parvifolia 'Burnley Select' was grown from seed taken from a tree at the Burnley (horticultural) College, University of Melbourne and selected by Dr Peter May.

Elm leaf beetle species of insect

Xanthogaleruca luteola, commonly known as the elm-leaf beetle, is an invasive beetle pest species in the family Chrysomelidae.

Pheromone trap

A pheromone trap is a type of insect trap that uses pheromones to lure insects. Sex pheromones and aggregating pheromones are the most common types used. A pheromone-impregnated lure, as the red rubber septa in the picture, is encased in a conventional trap such as a bottle trap, Delta trap, water-pan trap, or funnel trap. Pheromone traps are used both to count insect populations by sampling, and to trap pests such as clothes moths to destroy them.

<i>Scolytus</i> genus of insects

Scolytus is a genus of bark beetles. It includes several species notorious for destroying trees in the forests. The Dutch elm disease is spread in North America by two species : the native elm bark beetle, Hylurgopinus rufipes, and the European elm bark beetle, Scolytus multistriatus. In Europe, while the aforementioned Scolytus multistriatus again acts as vector for infection, it is much less effective than the large elm bark beetle Scolytus scolytus.

The Chinese Elm Ulmus parvifolia cultivar 'Small Frye' is to be released by Plant Introductions Inc. of Georgia

European spruce bark beetle species of insect

The European spruce bark beetle, is a species of beetle in the weevil subfamily Scolytinae, the bark beetles, and is found from Europe to Asia Minor and some parts of Africa.

<i>Ips</i> (beetle) genus of insects

Ips is a genus of beetles in the family Curculionidae, the true weevils. They are bark beetles, members of the subfamily Scolytinae. Species are distributed throughout the Northern Hemisphere. Some are known as introduced species in Australia and Africa. Many species are pests of forest trees, especially pines and spruces. They are known commonly as engraver beetles, ips engraver beetles, and pine engravers.

References

  1. 1 2 Warren, Stuart (1982). Organic synthesis : the disconnection approach.
  2. Beck, Keith (1 September 1978). "Pheromone chemistry of the smaller European elm bark beetle". Journal of Chemical Education. 55 (9): 567. doi:10.1021/ed055p567.