Iridomyrmecin

Last updated
Iridomyrmecin
Iridomyrmecin.svg
Names
Preferred IUPAC name
(4S,4aS,7S,7aR)-4,7-Dimethylhexahydrocyclopenta[c]pyran-3(1H)-one
Other names
Iridomyrmexin
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C10H16O2/c1-6-3-4-8-7(2)10(11)12-5-9(6)8/h6-9H,3-5H2,1-2H3/t6-,7-,8+,9+/m0/s1
  • O=C1OC[C@@H]2[C@H](CC[C@@H]2[C@@H]1C)C
Properties
C10H16O2
Molar mass 168.236 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Iridomyrmecin is a defensive chemical, classified as an iridoid, isolated from ants of the genus Iridomyrmex . [1] It has also evolved into a sex pheromone in wasps such as Leptopilina , [2] with host species using the smell of iridomyrmecin as a way of detecting the presence of the parasitoid wasps. [3] Iridomyrmecin is also found in a variety of plants including Actinidia polygama . [4]

See also

Related Research Articles

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<span class="mw-page-title-main">Venom</span> Toxin secreted by an animal

Venom or zootoxin is a type of toxin produced by an animal that is actively delivered through a wound by means of a bite, sting, or similar action. The toxin is delivered through a specially evolved venom apparatus, such as fangs or a stinger, in a process called envenomation. Venom is often distinguished from poison, which is a toxin that is passively delivered by being ingested, inhaled, or absorbed through the skin, and toxungen, which is actively transferred to the external surface of another animal via a physical delivery mechanism.

<span class="mw-page-title-main">Parasitism</span> Relationship between species where one organism lives on or in another organism, causing it harm

Parasitism is a close relationship between species, where one organism, the parasite, lives on or inside another organism, the host, causing it some harm, and is adapted structurally to this way of life. The entomologist E. O. Wilson characterised parasites as "predators that eat prey in units of less than one". Parasites include single-celled protozoans such as the agents of malaria, sleeping sickness, and amoebic dysentery; animals such as hookworms, lice, mosquitoes, and vampire bats; fungi such as honey fungus and the agents of ringworm; and plants such as mistletoe, dodder, and the broomrapes.

<span class="mw-page-title-main">Pheromone</span> Secreted or excreted chemical factor that triggers a social response in members of the same species

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<span class="mw-page-title-main">Aphid</span> Superfamily of insects

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<span class="mw-page-title-main">Parasitoid</span> Organism that lives with its host and kills it

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Chemical ecology is the study of chemically mediated interactions between living organisms, and the effects of those interactions on the demography, behavior and ultimately evolution of the organisms involved. It is thus a vast and highly interdisciplinary field. Chemical ecologists seek to identify the specific molecules that function as signals mediating community or ecosystem processes and to understand the evolution of these signals. The substances that serve in such roles are typically small, readily-diffusible organic molecules, but can also include larger molecules and small peptides.

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<span class="mw-page-title-main">Parasitoid wasp</span> Group of wasps

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<span class="mw-page-title-main">Ant mimicry</span> Animals that resemble ants

Ant mimicry or myrmecomorphy is mimicry of ants by other organisms. Ants are abundant all over the world, and potential predators that rely on vision to identify their prey, such as birds and wasps, normally avoid them, because they are either unpalatable or aggressive. Spiders are the most common ant mimics. Additionally, some arthropods mimic ants to escape predation, while others mimic ants anatomically and behaviourally to hunt ants in aggressive mimicry. Ant mimicry has existed almost as long as ants themselves; the earliest ant mimics in the fossil record appear in the mid Cretaceous alongside the earliest ants. Indeed one of the earliest, Burmomyrma, was initially classified as an ant.

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<span class="mw-page-title-main">Wasp</span> Group of insects

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<span class="mw-page-title-main">Major urinary proteins</span> Proteins found in the urine and other secretions of many animals

Major urinary proteins (Mups), also known as α2u-globulins, are a subfamily of proteins found in abundance in the urine and other secretions of many animals. Mups provide a small range of identifying information about the donor animal, when detected by the vomeronasal organ of the receiving animal. They belong to a larger family of proteins known as lipocalins. Mups are encoded by a cluster of genes, located adjacent to each other on a single stretch of DNA, that varies greatly in number between species: from at least 21 functional genes in mice to none in humans. Mup proteins form a characteristic glove shape, encompassing a ligand-binding pocket that accommodates specific small organic chemicals.

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

Chemical defense is a strategy employed by many organisms to avoid consumption by producing toxic or repellent metabolites or chemical warnings which incite defensive behavioral changes. The production of defensive chemicals occurs in plants, fungi, and bacteria, as well as invertebrate and vertebrate animals. The class of chemicals produced by organisms that are considered defensive may be considered in a strict sense to only apply to those aiding an organism in escaping herbivory or predation. However, the distinction between types of chemical interaction is subjective and defensive chemicals may also be considered to protect against reduced fitness by pests, parasites, and competitors. Repellent rather than toxic metabolites are allomones, a sub category signaling metabolites known as semiochemicals. Many chemicals used for defensive purposes are secondary metabolites derived from primary metabolites which serve a physiological purpose in the organism. Secondary metabolites produced by plants are consumed and sequestered by a variety of arthropods and, in turn, toxins found in some amphibians, snakes, and even birds can be traced back to arthropod prey. There are a variety of special cases for considering mammalian antipredatory adaptations as chemical defenses as well.

Insects have a wide variety of predators, including birds, reptiles, amphibians, mammals, carnivorous plants, and other arthropods. The great majority (80–99.99%) of individuals born do not survive to reproductive age, with perhaps 50% of this mortality rate attributed to predation. In order to deal with this ongoing escapist battle, insects have evolved a wide range of defense mechanisms. The only restraint on these adaptations is that their cost, in terms of time and energy, does not exceed the benefit that they provide to the organism. The further that a feature tips the balance towards beneficial, the more likely that selection will act upon the trait, passing it down to further generations. The opposite also holds true; defenses that are too costly will have a little chance of being passed down. Examples of defenses that have withstood the test of time include hiding, escape by flight or running, and firmly holding ground to fight as well as producing chemicals and social structures that help prevent predation.

References

  1. Cavill GW, Ford DL, Locksley HD (1956). "The chemistry of ants. I. Terpenoid constituents of some Australian Iridomyrmex species". Australian Journal of Chemistry. 9 (2): 288–293. doi:10.1071/CH9560288.
  2. Weiss I, Rössler T, Hofferberth J, Brummer M, Ruther J, Stökl J (2013-11-15). "A nonspecific defensive compound evolves into a competition avoidance cue and a female sex pheromone". Nature Communications. 4 (1): 2767. Bibcode:2013NatCo...4.2767W. doi:10.1038/ncomms3767. PMC   3868268 . PMID   24231727.
  3. Ebrahim SA, Dweck HK, Stökl J, Hofferberth JE, Trona F, Weniger K, et al. (December 2015). "Drosophila Avoids Parasitoids by Sensing Their Semiochemicals via a Dedicated Olfactory Circuit". PLOS Biology. 13 (12): e1002318. doi: 10.1371/journal.pbio.1002318 . PMC   4687525 . PMID   26674493.
  4. Sakan T, Isoe S, Hyeon SB, Katsumura R, Maeda T, Wolinsky J, et al. (1965). "Exact nature of matatabilactone and the terpenes of Nepeta cataria". Tetrahedron Letters. 6 (46): 4097–4102. doi:10.1016/s0040-4039(01)99572-3.