Antifeedant

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Amygdalin, a cyanide-releasing compound, is produced by some plants to deter herbivores. Amygdalin skeletal.png
Amygdalin, a cyanide-releasing compound, is produced by some plants to deter herbivores.

Antifeedants are organic compounds produced by plants to repel herbivores through distaste or toxicity. These chemical compounds are typically classified as secondary metabolites in that they are not essential for the metabolism of the plant, but instead confer longevity. Antifeedants exhibit a wide range of activities and chemical structures as biopesticides. Examples include rosin, which inhibits attack on trees, and many alkaloids, which are highly toxic to specific insect species, [2] such as quassinoids (extracts from Quassia trees) against the diamondback moth ( Plutela xylostella ). [3] Samadera indica also has quassinoids used for insect antifeedant uses. [4]

Contents

Limonoids such as limonin are antifeedants produced by a number of plants of the families cucurbitaceae Rutaceae and Meliaceae. Limonin.svg
Limonoids such as limonin are antifeedants produced by a number of plants of the families cucurbitaceae Rutaceae and Meliaceae.

History

"Plant-derived insecticides (e.g., rotenone, veratridines, pyrethrins, and nicotine) have been used for insect control since antiquity." [6] The active ingredients in these plants have been purified and modified. For example, variations on pyrethrin have spawned a large number of synthetic insecticides called pyrethroids.

Culinary implications

In addition to their role defending the plant, antifeedants often confer taste or odors, enhancing the flavor of certain plants. Examples are provided by cruciferous vegetables including mustard, cabbage, and horseradish, which release pungent oils containing glucosinolates when the plant material is chewed, cut, or otherwise damaged. [7] The odorous components of garlic are thought to have evolved to deter insects. [8]

Related Research Articles

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

Brassicaceae or Cruciferae is a medium-sized and economically important family of flowering plants commonly known as the mustards, the crucifers, or the cabbage family. Most are herbaceous plants, while some are shrubs. The leaves are simple, lack stipules, and appear alternately on stems or in rosettes. The inflorescences are terminal and lack bracts. The flowers have four free sepals, four free alternating petals, two shorter free stamens and four longer free stamens. The fruit has seeds in rows, divided by a thin wall.

<i>Quassia</i> Genus of plants in the Simaroubaceae family found in the tropics of the world

Quassia is a plant genus in the family Simaroubaceae. Its size is disputed; some botanists treat it as consisting of only one species, Quassia amara from tropical South America, while others treat it in a wide circumscription as a pantropical genus containing up to 40 species of trees and shrubs.

<span class="mw-page-title-main">Horseradish</span> Species of flowering plants in the cabbage family Brassicaceae

Horseradish is a perennial plant of the family Brassicaceae. It is a root vegetable, cultivated and used worldwide as a spice and as a condiment. The species is probably native to Southeastern Europe and Western Asia.

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

Insecticides are pesticides used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Acaricides, which kill mites and ticks, are not strictly insecticides, but are usually classified together with insecticides. The major use of Insecticides is agriculture, but they are also used in home and garden, industrial buildings, vector control and control of insect parasites of animals and humans. 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">Azadirachtin</span> Chemical compound

Azadirachtin, a chemical compound belonging to the limonoid group, is a secondary metabolite present in neem seeds. It is a highly oxidized tetranortriterpenoid which boasts a plethora of oxygen-bearing functional groups, including an enol ether, acetal, hemiacetal, tetra-substituted epoxide and a variety of carboxylic esters.

Pyrethrum was a genus of several Old World plants now classified in either Chrysanthemum or Tanacetum which are cultivated as ornamentals for their showy flower heads. Pyrethrum continues to be used as a common name for plants formerly included in the genus Pyrethrum. Pyrethrum is also the name of a natural insecticide made from the dried flower heads of Chrysanthemum cinerariifolium and Chrysanthemum coccineum. The insecticidal compounds present in these species are pyrethrins.

<span class="mw-page-title-main">Pyrethrin</span> Class of organic chemical compounds with insecticidal properties

The pyrethrins are a class of organic compounds normally derived from Chrysanthemum cinerariifolium that have potent insecticidal activity by targeting the nervous systems of insects. Pyrethrin naturally occurs in chrysanthemum flowers and is often considered an organic insecticide when it is not combined with piperonyl butoxide or other synthetic adjuvants. Their insecticidal and insect-repellent properties have been known and used for thousands of years.

<span class="mw-page-title-main">Pyrethroid</span> Class of insecticides

A pyrethroid is an organic compound similar to the natural pyrethrins, which are produced by the flowers of pyrethrums. Pyrethroids are used as commercial and household insecticides.

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

Allyl isothiocyanate (AITC) is a naturally occurring unsaturated isothiocyanate. The colorless oil is responsible for the pungent taste of cruciferous vegetables such as mustard, radish, horseradish, and wasabi. This pungency and the lachrymatory effect of AITC are mediated through the TRPA1 and TRPV1 ion channels. It is slightly soluble in water, but more soluble in most organic solvents.

<span class="mw-page-title-main">Glucosinolate</span> Class of chemical compounds

Glucosinolates are natural components of many pungent plants such as mustard, cabbage, and horseradish. The pungency of those plants is due to mustard oils produced from glucosinolates when the plant material is chewed, cut, or otherwise damaged. These natural chemicals most likely contribute to plant defence against pests and diseases, and impart a characteristic bitter flavor property to cruciferous vegetables.

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

Sinigrin or allyl glucosinolate is a glucosinolate that belongs to the family of glucosides found in some plants of the family Brassicaceae such as Brussels sprouts, broccoli, and the seeds of black mustard. Whenever sinigrin-containing plant tissue is crushed or otherwise damaged, the enzyme myrosinase degrades sinigrin to a mustard oil, which is responsible for the pungent taste of mustard and horseradish. Seeds of white mustard, Sinapis alba, give a less pungent mustard because this species contains a different glucosinolate, sinalbin.

<i>Barbarea vulgaris</i> Species of flowering plant

Barbarea vulgaris, also called wintercress, or alternatively winter rocket, rocketcress, yellow rocketcress, yellow rocket, wound rocket, herb barbara, creases, or creasy greens, is a biennial herb of the genus Barbarea, belonging to the family Brassicaceae.

<span class="mw-page-title-main">Diamondback moth</span> Species of moth

The diamondback moth, sometimes called the cabbage moth, is a moth species of the family Plutellidae and genus Plutella. The small, grayish-brown moth sometimes has a cream-colored band that forms a diamond along its back. The species may have originated in Europe, South Africa, or the Mediterranean region, but it has now spread worldwide.

<span class="mw-page-title-main">Nitenpyram</span> Insecticide

Nitenpyram is a chemical frequently used as an insecticide in agriculture and veterinary medicine. The compound is an insect neurotoxin belonging to the class of neonicotinoids which works by blocking neural signaling of the central nervous system. It does so by binding irreversibly to the nicotinic acetylcholine receptor (nACHr) causing a stop of the flow of ions in the postsynaptic membrane of neurons leading to paralysis and death. Nitenpyram is highly selective towards the variation of the nACHr which insects possess, and has seen extensive use in targeted, insecticide applications.

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

Gluconasturtiin or phenethyl glucosinolate is one of the most widely distributed glucosinolates in the cruciferous vegetables, mainly in the roots, and is probably one of the plant compounds responsible for the natural pest-inhibiting properties of growing crucifers, such as cabbage, mustard or rape, in rotation with other crops. This effect of gluconasturtiin is due to its degradation by the plant enzyme myrosinase into phenethyl isothiocyanate, which is toxic to many organisms.

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

Acetamiprid is an organic compound with the chemical formula C10H11ClN4. It is an odorless neonicotinoid insecticide produced under the trade names Assail, and Chipco by Aventis CropSciences. It is systemic and intended to control sucking insects (Thysanoptera, Hemiptera, mainly aphids) on crops such as leafy vegetables, citrus fruits, pome fruits, grapes, cotton, cole crops, and ornamental plants. It is also a key pesticide in commercial cherry farming due to its effectiveness against the larvae of the cherry fruit fly.

The mustard oil bomb, formerly known as the glucosinolate–myrosinase complex, is a chemical herbivory defense system found in members of the Brassicaceae. The mustard oil bomb requires the activation of a common plant secondary metabolite, glucosinolate, by an enzyme, myrosinase. The defense complex is typical among plant defenses to herbivory in that the two molecules are stored in different compartments in the leaves of plants until the leaf is torn by an herbivore. The glucosinolate has a β-glucose and a sulfated oxime. The myrosinase removes the β-glucose to form mustard oils that are toxic to herbivores. The defense system was named a "bomb" by Matile, because it like a real bomb is waiting to detonate upon disturbance of the plant tissue.

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

Dioscorine is an alkaloid toxin isolated from the tubers of tropical yam on several continents. It has been used as a monkey poison in some African countries, and as an arrow poison to aid in hunting in several parts of Asia. It was first isolated from Dioscorea hirsute by Boorsma in 1894 and obtained in a crystalline form by Schutte in 1897, and has since been found in other Dioscorea species. Dioscorine is a neurotoxin that acts by blocking the nicotinic acetylcholine receptor. Dioscorine is generally isolated in tandem with other alkaloids such as dioscin but is usually the most potent toxin in the mixture. It is a convulsant, producing symptoms similar to picrotoxin, with which it shares a similar mechanism of action.

<i>Samadera</i> Genus of flowering trees

Samadera is a genus of four species of plants belonging to the family Simaroubaceae in the order Sapindales. Its range is from eastern Africa through tropical Asia to eastern Australia.

<i>Samadera indica</i> Species of plant

Samadera indica, the bitter wood or Niepa bark tree, is a species of plant in the family Simaroubaceae. It is a shrub or tree and grows primarily in wet tropical regions, from west Africa, through India, then down through Indonesia to Malesia.

References

  1. Gleadow, RM; Møller, BL (2014). "Cyanogenic glycosides: synthesis, physiology, and phenotypic plasticity". Annual Review of Plant Biology. 65: 155–85. doi:10.1146/annurev-arplant-050213-040027. PMID   24579992.
  2. Richard N. Bennett; Roger M. Wallsgrove (1994). "Secondary metabolites in plant defence mechanisms". New Phytologist. 127 (4): 617–633. doi:10.1111/j.1469-8137.1994.tb02968.x. PMID   33874382.
  3. Daido, M.; Ohno, N.; Imamura, K.; Fukamiya, N.; Hatakoshi, M.; Yamazaki, H.; et al. (1995). "Antifeedant and insecticidal activity of quassinoids against the diamondback moth (Plutela xylostella) and structure-activity relationships". Biosci. Biotechnol. Biochem. 59 (6): 974–9. doi:10.1271/bbb.59.974.
  4. Govindachari, T.R.; Krishnakumari, G.N.; Gopalakrishnan, G.; Suresh, G.; Wesley, S.D.; Sreelatha, T. (2001). "Insect antifeedant and growth regulating activities of quassinoids from Samadera indica". Fitoterapia. 72 (5): 568–71. doi:10.1016/S0367-326X(00)00342-7. PMID   11429258.
  5. Amit Roy and Shailendra Saraf (2006). "Limonoids: Overview of Significant Bioactive Triterpenes Distributed in Plants Kingdom". Biol. Pharm. Bull. 29 (2): 191–201. doi: 10.1248/bpb.29.191 . PMID   16462017.
  6. Metcalf, Robert L. (2000). "Insect Control". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a14_263. ISBN   978-3-527-30673-2.
  7. Johnson, I. T (2002). "Glucosinolates: Bioavailability and importance to health". International Journal for Vitamin and Nutrition Research. 72 (1): 26–31. doi:10.1024/0300-9831.72.1.26. PMID   11887749.
  8. Macpherson, Lindsey J.; Geierstanger, Bernhard H.; Viswanath, Veena; Bandell, Michael; Eid, Samer R.; Hwang, SunWook; Patapoutian, Ardem (May 24, 2005). "The Pungency of Garlic: Activation of TRPA1 and TRPV1 in Response to Allicin" (PDF). Current Biology . 15 (10): 929–34. Bibcode:2005CBio...15..929M. doi: 10.1016/j.cub.2005.04.018 . PMID   15916949.