Oosporein

Last updated
Oosporein
Oosporein.svg
Names
IUPAC name
2-(2,5-dihydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-3,6-dihydroxy-5-methylcyclohexa-2,5-diene-1,4-dione
Other names
    • NSC 88466 [1]
    • Chaetomidin [2]
    • Iso-Oosporein [2]
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C14H10O8/c1-3-7(15)11(19)5(12(20)8(3)16)6-13(21)9(17)4(2)10(18)14(6)22/h15,17,20,22H,1-2H3
    Key: DHMPJEGFPQTNFX-UHFFFAOYSA-N
  • Key: DHMPJEGFPQTNFX-UHFFFAOYSA-N
  • CC1=C(C(=O)C(=C(C1=O)O)C2=C(C(=O)C(=C(C2=O)O)C)O)O
Properties
C14H10O8
Molar mass 306.226 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Oosporein is a toxic, bronze colored dibenzoquinone with the molecular formula C14H10O8. [2] [3] Oosporein was first extracted from various molds and has antibiotic, [4] antiviral, cytotoxic, antifungal, and Insecticide properties. [3] [5] [2]

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">Symbiosis</span> Close, long-term biological interaction between distinct organisms (usually species)

Symbiosis is any type of a close and long-term biological interaction, between two organisms of different species. The two organisms, termed symbionts, can be either in a mutualistic, a commensalistic, or a parasitic relationship. In 1879, Heinrich Anton de Bary defined symbiosis as "the living together of unlike organisms".

<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">Cicada</span> Superfamily of insects

The cicadas are a superfamily, the Cicadoidea, of insects in the order Hemiptera. They are in the suborder Auchenorrhyncha, along with smaller jumping bugs such as leafhoppers and froghoppers. The superfamily is divided into two families, the Tettigarctidae, with two species in Australia, and the Cicadidae, with more than 3,000 species described from around the world; many species remain undescribed. Nearly all of cicada species are annual cicadas with the exception of the few North American periodical cicada species, genus Magicicada, which in a given region emerge en masse every 13 or 17 years.

<span class="mw-page-title-main">Capsaicin</span> Pungent chemical compound in chili peppers

Capsaicin (8-methyl-N-vanillyl-6-nonenamide) is an active component of chili peppers, which are plants belonging to the genus Capsicum. It is a potent irritant for mammals, including humans, and produces a sensation of burning in any tissue with which it comes into contact. Capsaicin and several related amides (capsaicinoids) are produced as secondary metabolites by chili peppers, likely as deterrents against certain mammals and fungi. Pure capsaicin is a hydrophobic, colorless, highly pungent crystalline solid.

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<span class="mw-page-title-main">Convergent evolution</span> Independent evolution of similar features

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

Aphids are small sap-sucking insects and members of the superfamily Aphidoidea. Common names include greenfly and blackfly, although individuals within a species can vary widely in color. The group includes the fluffy white woolly aphids. A typical life cycle involves flightless females giving live birth to female nymphs—who may also be already pregnant, an adaptation scientists call telescoping generations—without the involvement of males. Maturing rapidly, females breed profusely so that the number of these insects multiplies quickly. Winged females may develop later in the season, allowing the insects to colonize new plants. In temperate regions, a phase of sexual reproduction occurs in the autumn, with the insects often overwintering as eggs.

<span class="mw-page-title-main">Chitin</span> Long-chain polymer of a N-acetylglucosamine

Chitin (C8H13O5N)n ( KY-tin) is a long-chain polymer of N-acetylglucosamine, an amide derivative of glucose. Chitin is the second most abundant polysaccharide in nature (behind only cellulose); an estimated 1 billion tons of chitin are produced each year in the biosphere. It is a primary component of cell walls in fungi (especially filamentous and mushroom-forming fungi), the exoskeletons of arthropods such as crustaceans and insects, the radulae, cephalopod beaks and gladii of molluscs and in some nematodes and diatoms. It is also synthesised by at least some fish and lissamphibians. Commercially, chitin is extracted from the shells of crabs, shrimps, shellfish and lobsters, which are major by-products of the seafood industry. The structure of chitin is comparable to cellulose, forming crystalline nanofibrils or whiskers. It is functionally comparable to the protein keratin. Chitin has proved useful for several medicinal, industrial and biotechnological purposes.

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

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<span class="mw-page-title-main">Animal</span> Kingdom of living things

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<span class="mw-page-title-main">Fungus</span> Biological kingdom, separate from plants and animals

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<span class="mw-page-title-main">Plant use of endophytic fungi in defense</span>

Plant use of endophytic fungi in defense occurs when endophytic fungi, which live symbiotically with the majority of plants by entering their cells, are utilized as an indirect defense against herbivores. In exchange for carbohydrate energy resources, the fungus provides benefits to the plant which can include increased water or nutrient uptake and protection from phytophagous insects, birds or mammals. Once associated, the fungi alter nutrient content of the plant and enhance or begin production of secondary metabolites. The change in chemical composition acts to deter herbivory by insects, grazing by ungulates and/or oviposition by adult insects. Endophyte-mediated defense can also be effective against pathogens and non-herbivory damage.

<span class="mw-page-title-main">Marine fungi</span> Species of fungi that live in marine or estuarine environments

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References

  1. "Oosporein (CAS 475-54-7)". www.caymanchem.com.
  2. 1 2 3 4 Eisenbrand, Gerhard; Schreier, Peter (14 May 2014). RÖMPP Lexikon Lebensmittelchemie, 2. Auflage, 2006 (in German). Georg Thieme Verlag. p. 824. ISBN   978-3-13-179282-2.
  3. 1 2 Feng, Peng; Shang, Yanfang; Cen, Kai; Wang, Chengshu (8 September 2015). "Fungal biosynthesis of the bibenzoquinone oosporein to evade insect immunity". Proceedings of the National Academy of Sciences. 112 (36): 11365–11370. Bibcode:2015PNAS..11211365F. doi: 10.1073/pnas.1503200112 . PMC   4568701 . PMID   26305932.
  4. Handbook of Applied Mycology: Volume 2: Humans, Animals and Insects. CRC Press. 25 July 1991. p. 626. ISBN   978-0-8247-8435-5.
  5. Ramesha, Alurappa; Venkataramana, M.; Nirmaladevi, Dhamodaran; Gupta, Vijai K.; Chandranayaka, S.; Srinivas, Chowdappa (1 September 2015). "Cytotoxic effects of oosporein isolated from endophytic fungus Cochliobolus kusanoi". Frontiers in Microbiology. 6: 870. doi: 10.3389/fmicb.2015.00870 . PMC   4556033 . PMID   26388840.

Further reading