Annonin

Last updated

Annonins are a group of chemical compounds classified as acetogenins. They are found in the extracts of Annona seeds ( A. squamosa and A. muricata ). [1] [2] Annonin-based bioinsecticides are used to control Coleoptera (beetle) pests commonly found in stored organic cereal and beans in the country of Brazil. [3] Other different types of annonin-based insecticides, derived from A. mucosa, fight off lepidopteran (moth) pests that infest cabbage leaves, also found in the tropical climates of Brazil. The benefit of using these bioinsecticides is their relatively low cost and no phytotoxicity. [4] These annonin molecules act as overpowering inhibitors of complex I (NADH: ubiquinone oxidoreductase) in the electron-transport chain in the mitochondria of quarry pests. In cell membranes of these same pests, annonins also inhibit coenzyme NADH, causing these arthropods to die. [5]

Chemical structure of annonin I Annonin I.svg
Chemical structure of annonin I

Related Research Articles

<span class="mw-page-title-main">Phenothiazine</span> Heterocyclic compound containing a ring of four carbon, one nitrogen and one sulfur atom

Phenothiazine, abbreviated PTZ, is an organic compound that has the formula S(C6H4)2NH and is related to the thiazine-class of heterocyclic compounds. Derivatives of phenothiazine are highly bioactive and have widespread use and rich history. The derivatives chlorpromazine and promethazine revolutionized the fields of psychiatry and allergy treatment, respectively. An earlier derivative, methylene blue, was one of the first antimalarial drugs, and derivatives are under investigation as possible anti-infective drugs. Phenothiazine is a prototypical pharmaceutical lead structure in medicinal chemistry.

<span class="mw-page-title-main">Pesticide</span> Substance used to destroy pests

Pesticides are substances that are meant to control pests. This includes herbicide, insecticide, nematicide, molluscicide, piscicide, avicide, rodenticide, bactericide, insect repellent, animal repellent, microbicide, fungicide, and lampricide. The most common of these are herbicides which account for approximately 80% of all pesticide use. Most pesticides are intended to serve as plant protection products, which in general, protect plants from weeds, fungi, or insects. As an example, the fungus Alternaria solani is used to combat the aquatic weed Salvinia.

<span class="mw-page-title-main">Respiratory complex I</span>

Respiratory complex I, EC 7.1.1.2 is the first large protein complex of the respiratory chains of many organisms from bacteria to humans. It catalyzes the transfer of electrons from NADH to coenzyme Q10 (CoQ10) and translocates protons across the inner mitochondrial membrane in eukaryotes or the plasma membrane of bacteria.

<span class="mw-page-title-main">Insecticide</span> Pesticide used against insects

Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to be a major factor behind the increase in the 20th-century's agricultural productivity. Nearly all insecticides have the potential to significantly alter ecosystems; many are toxic to humans and/or animals; some become concentrated as they spread along the food chain.

<span class="mw-page-title-main">Pesticide resistance</span> Decreased effectiveness of a pesticide on a pest

Pesticide resistance describes the decreased susceptibility of a pest population to a pesticide that was previously effective at controlling the pest. Pest species evolve pesticide resistance via natural selection: the most resistant specimens survive and pass on their acquired heritable changes traits to their offspring. If a pest has resistance then the pesticide lacks efficacy – efficacy and resistance are inversely related.

<span class="mw-page-title-main">Annonaceae</span> Family of flowering plants

The Annonaceae are a family of flowering plants consisting of trees, shrubs, or rarely lianas commonly known as the custard apple family or soursop family. With 108 accepted genera and about 2400 known species, it is the largest family in the Magnoliales. Several genera produce edible fruit, most notably Annona, Anonidium, Asimina, Rollinia, and Uvaria. Its type genus is Annona. The family is concentrated in the tropics, with few species found in temperate regions. About 900 species are Neotropical, 450 are Afrotropical, and the remaining are Indomalayan.

<i>Annona</i> Genus of fruits and plants

Annona is a genus of flowering plants in the pawpaw/sugar apple family, Annonaceae. It is the second largest genus in the family after Guatteria, containing approximately 166 species of mostly Neotropical and Afrotropical trees and shrubs.

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

Malathion is an organophosphate insecticide which acts as an acetylcholinesterase inhibitor. In the USSR, it was known as carbophos, in New Zealand and Australia as maldison and in South Africa as mercaptothion.

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

Diazinon, a colorless to dark brown liquid, is a thiophosphoric acid ester developed in 1952 by Ciba-Geigy, a Swiss chemical company. It is a nonsystemic organophosphate insecticide formerly used to control cockroaches, silverfish, ants, and fleas in residential, non-food buildings. Diazinon was heavily used during the 1970s and early 1980s for general-purpose gardening use and indoor pest control. A bait form was used to control scavenger wasps in the western U.S. Diazinon is used in flea collars for domestic pets in Australia and New Zealand. Residential uses of diazinon were outlawed in the U.S. in 2004 because of human health risks but it is still approved for agricultural uses. An emergency antidote is atropine.

<i>Annona squamosa</i> Species of tree

Annona squamosa is a small, well-branched tree or shrub from the family Annonaceae that bears edible fruits called sugar-apples or sweetsops. It tolerates a tropical lowland climate better than its relatives Annona reticulata and Annona cherimola helping make it the most widely cultivated of these species. Annona squamosa is a small, semi-(or late) deciduous, much-branched shrub or small tree 3 to 8 metres tall similar to soursop.

<span class="mw-page-title-main">Aldicarb</span> Chemical compound (insecticide)

Aldicarb is a carbamate insecticide which is the active substance in the pesticide Temik. It is effective against thrips, aphids, spider mites, lygus, fleahoppers, and leafminers, but is primarily used as a nematicide. Aldicarb is a cholinesterase inhibitor which prevents the breakdown of acetylcholine in the synapse. In case of severe poisoning, the victim dies of respiratory failure.

A Biopesticide is a biological substance or organism that damages, kills, or repels organisms seens as pests. Biological pest management intervention involves predatory, parasitic, or chemical relationships.

<i>Asimina triloba</i> Species of tree

Asimina triloba, the American papaw, pawpaw, paw paw, or paw-paw, among many regional names, is a small deciduous tree native to the eastern United States and Canada, producing a large, yellowish-green to brown fruit. Asimina is the only temperate genus in the tropical and subtropical flowering plant family Annonaceae, and Asimina triloba has the most northern range of all. Well-known tropical fruits of different genera in family Annonaceae include the custard-apple, cherimoya, sweetsop, ylang-ylang, and soursop.

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

Spinosad is an insecticide based on chemical compounds found in the bacterial species Saccharopolyspora spinosa. The genus Saccharopolyspora was discovered in 1985 in isolates from crushed sugarcane. The bacteria produce yellowish-pink aerial hyphae, with bead-like chains of spores enclosed in a characteristic hairy sheath. This genus is defined as aerobic, Gram-positive, nonacid-fast actinomycetes with fragmenting substrate mycelium. S. spinosa was isolated from soil collected inside a nonoperational sugar mill rum still in the Virgin Islands. Spinosad is a mixture of chemical compounds in the spinosyn family that has a generalized structure consisting of a unique tetracyclic ring system attached to an amino sugar (D-forosamine) and a neutral sugar (tri-Ο-methyl-L-rhamnose). Spinosad is relatively nonpolar and not easily dissolved in water.

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

Annonacin is a chemical compound with toxic effects, especially in the nervous system, found in some fruits such as the paw paw, custard apples, soursop, and others from the family Annonaceae. It is a member of the class of compounds known as acetogenins. Annonacin-containing fruit products are regularly consumed throughout the West Indies for their traditional medicine uses.

<span class="mw-page-title-main">Acetogenin</span> Group of chemical compounds

Acetogenins are a class of polyketide natural products found in plants of the family Annonaceae. They are characterized by linear 32- or 34-carbon chains containing oxygenated functional groups including hydroxyls, ketones, epoxides, tetrahydrofurans and tetrahydropyrans. They are often terminated with a lactone or butenolide. Over 400 members of this family of compounds have been isolated from 51 different species of plants. Many acetogenins are characterized by neurotoxicity.

<span class="mw-page-title-main">Environmental impact of pesticides</span> Environmental effect

The environmental effects of pesticides describe the broad series of consequences of using pesticides. The unintended consequences of pesticides is one of the main drivers of the negative impact of modern industrial agriculture on the environment. Pesticides, because they are toxic chemicals meant to kill pest species, can affect non-target species, such as plants, animals and humans. Over 98% of sprayed insecticides and 95% of herbicides reach a destination other than their target species, because they are sprayed or spread across entire agricultural fields. Other agrochemicals, such as fertilizers, can also have negative effects on the environment.

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

Uvaricin is a bis(tetrahydrofuranoid) fatty acid lactone that was first isolated in 1982 from the roots of the Annonaceae Uvaria acuminata. Uvaricin was the first known example in a class of compounds known as acetogenins. Acetogenins, which are found in plants of the family Annonaceae, seem to kill cells by inhibiting NADH dehydrogenase in the mitochondrion. A method to synthesize uvaricin was first published in 1998, and an improved stereoselective synthesis published in 2001.

<i>Tuta absoluta</i> Pest worm of tomato, potato, and others

Tuta absoluta is a species of moth in family Gelechiidae known by the common names South American tomato pinworm, tomato leafminer, tomato pinworm and South American tomato moth. It is well known as a serious pest of tomato crops in Europe, Africa, western Asia and South and Central America, with larvae causing up to 100% loss if not effectively controlled.

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

Novaluron, or (±)-1-[3-chloro-4-(1,1,2-trifluoro-2-trifluoro- methoxyethoxy)phenyl]-3-(2,6-difluorobenzoyl)urea, is a chemical with pesticide properties, belonging to the class of insecticides called insect growth regulators. It is a benzoylphenyl urea developed by Makhteshim-Agan Industries Ltd.. In the United States, the compound has been used on food crops, including apples, potatoes, brassicas, ornamentals, and cotton. Patents and registrations have been approved or are ongoing in several other countries throughout Europe, Asia, Africa, South America, and Australia. The US Environmental Protection Agency and the Canadian Pest Management Regulatory Agency consider novaluron to pose low risk to the environment and non-target organisms and value it as an important option for integrated pest management that should decrease reliance on organophosphorus, carbamate and pyrethroid insecticides.

References

  1. Londershausen, Michael; Leicht, Wolfgang; Lieb, Folker; Moeschler, Heinrich; Weiss, Hanns (1991). "Molecular mode of action of annonins". Pesticide Science. 33 (4): 427. doi:10.1002/ps.2780330405.
  2. Wani JA, Wali AF, Majid S, Rasool S, Rehman MU, Rashid SM, Ali S, Farooq S, Rasool S, Ahmad A, Qamar W (2020). "Bio-pesticides: Application and possible mechanism of action". Bioremediation and Biotechnology. 2: 97–119. doi:10.1007/978-3-030-40333-1_6. ISBN   978-3-030-40332-4. S2CID   218939420.
  3. Ribeiro, L. P.; Zanardi, O. Z.; Gonçalves, G. L. P.; Ansante, T. F.; Yamamoto, P. T.; Vendramim, J. D. (2017-03-28). "Toxicity of an Annonin-Based Commercial Bioinsecticide Against Three Primary Pest Species of Stored Products". Neotropical Entomology. 47 (1): 145–151. doi:10.1007/s13744-017-0510-6. PMID   28353149 . Retrieved 2020-04-26.
  4. Souza, Camila M.; Baldin, Edson L. L.; Ribeiro, Leandro P.; Silva, Ivana F.; Morando, Rafaela; Bicalho, Keylla U.; Vendramim, José D.; Fernandes, João B. (2018-12-10). "Lethal and growth inhibitory activities of Neotropical Annonaceae-derived extracts, commercial formulation, and an isolated acetogenin against Helicoverpa armigera". Journal of Pest Science. 90 (2): 701–709. doi:10.1007/s10340-016-0817-9. hdl: 11449/169236 . S2CID   37487656 . Retrieved 2020-04-26.
  5. Lewis, M.A.; Arnason, J.T.; Philogene, B.J.R.; Rupprecht, J.K.; Mclaughlin, J.L. (January 1993). "Inhibition of Respiration at Site I by Asimicin, an Insecticidal Acetogenin of the Pawpaw, Asimina triloba (Annonaceae)". Pesticide Biochemistry and Physiology. Volume 45, Issue 1. 45: 15–23. doi:10.1006/pest.1993.1003 . Retrieved 2020-04-27.