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Phytotoxins are substances that are poisonous or
toxic Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacterium, or plant, as well as the effect on a subst ...
to the growth of plants. Phytotoxic substances may result from human activity, as with
herbicide Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...
s, or they may be produced by plants, by microorganisms, or by naturally occurring chemical reactions. The term is also used to describe toxic chemicals produced by plants themselves, which function as defensive agents against their predators. Most examples pertaining to this definition of phytotoxin are members of various classes of specialised or secondary metabolites, including
alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...
s,
terpene Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predomi ...
s, and especially phenolics, though not all such compounds are toxic or serve defensive purposes. Phytotoxins may also be toxic to humans.


Toxins produced by plants


Alkaloids

Alkaloid Alkaloids are a broad class of natural product, naturally occurring organic compounds that contain at least one nitrogen atom. Some synthetic compounds of similar structure may also be termed alkaloids. Alkaloids are produced by a large varie ...
s are derived from
amino acids Amino acids are organic compounds that contain both amino and carboxylic acid functional groups. Although over 500 amino acids exist in nature, by far the most important are the Proteinogenic amino acid, 22 α-amino acids incorporated into p ...
, and contain
nitrogen Nitrogen is a chemical element; it has Symbol (chemistry), symbol N and atomic number 7. Nitrogen is a Nonmetal (chemistry), nonmetal and the lightest member of pnictogen, group 15 of the periodic table, often called the Pnictogen, pnictogens. ...
. They are medically important by interfering with components of the
nervous system In biology, the nervous system is the complex system, highly complex part of an animal that coordinates its behavior, actions and sense, sensory information by transmitting action potential, signals to and from different parts of its body. Th ...
affecting membrane transport,
protein synthesis Protein biosynthesis, or protein synthesis, is a core biological process, occurring inside cells, balancing the loss of cellular proteins (via degradation or export) through the production of new proteins. Proteins perform a number of critica ...
, and
enzyme An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
activities. They generally have a bitter taste. Alkaloids usually end in -ine (
caffeine Caffeine is a central nervous system (CNS) stimulant of the methylxanthine chemical classification, class and is the most commonly consumed Psychoactive drug, psychoactive substance globally. It is mainly used for its eugeroic (wakefulness pr ...
,
nicotine Nicotine is a natural product, naturally produced alkaloid in the nightshade family of plants (most predominantly in tobacco and ''Duboisia hopwoodii'') and is widely used recreational drug use, recreationally as a stimulant and anxiolytic. As ...
,
cocaine Cocaine is a tropane alkaloid and central nervous system stimulant, derived primarily from the leaves of two South American coca plants, ''Erythroxylum coca'' and ''Erythroxylum novogranatense, E. novogranatense'', which are cultivated a ...
,
morphine Morphine, formerly also called morphia, is an opiate that is found naturally in opium, a dark brown resin produced by drying the latex of opium poppies (''Papaver somniferum''). It is mainly used as an analgesic (pain medication). There are ...
,
ephedrine Ephedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to prevent hypotension, low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred ...
).


Terpenes

Terpene Terpenes () are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predomi ...
s are made of water-insoluble
lipids Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins (such as vitamins Vitamin A, A, Vitamin D, D, Vitamin E, E and Vitamin K, K), monoglycerides, diglycerides, phospholipids, and others. The fu ...
, and synthesized from
acetyl-CoA Acetyl-CoA (acetyl coenzyme A) is a molecule that participates in many biochemical reactions in protein, carbohydrate and lipid metabolism. Its main function is to deliver the acetyl group to the citric acid cycle (Krebs cycle) to be oxidation, o ...
or basic intermediates of
glycolysis Glycolysis is the metabolic pathway that converts glucose () into pyruvic acid, pyruvate and, in most organisms, occurs in the liquid part of cells (the cytosol). The Thermodynamic free energy, free energy released in this process is used to form ...
They often end in -ol (
menthol Menthol is an organic compound, specifically a Monoterpene, monoterpenoid, that occurs naturally in the oils of several plants in the Mentha, mint family, such as Mentha arvensis, corn mint and peppermint. It is a white or clear waxy crystallin ...
) and comprise the majority of plant essential oils. *
Monoterpenes Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen funct ...
are found in
gymnosperms The gymnosperms ( ; ) are a group of woody, perennial Seed plant, seed-producing plants, typically lacking the protective outer covering which surrounds the seeds in flowering plants, that include Pinophyta, conifers, cycads, Ginkgo, and gnetoph ...
and collect in the
resin A resin is a solid or highly viscous liquid that can be converted into a polymer. Resins may be biological or synthetic in origin, but are typically harvested from plants. Resins are mixtures of organic compounds, predominantly terpenes. Commo ...
ducts and may be released after an insect begins to feed to attract the insect's natural enemies. *
Sesquiterpenes Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many combinations. Biochemical modifications s ...
are bitter tasting to humans and are found on glandular hairs or subdermal pigments. *
Diterpenes Diterpenes are a class of terpenes composed of four isoprene units, often with the molecular formula C20H32. They are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being a prima ...
are contained in resin and block and deter insect feeding.
Taxol Paclitaxel, sold under the brand name Taxol among others, is a chemotherapy medication used to treat ovarian cancer, esophageal cancer, breast cancer, lung cancer, Kaposi's sarcoma, cervical cancer, and pancreatic cancer. It is administered by ...
, an important anticancer drug is found in this group. *
Triterpenes Triterpenes are a class of terpenes composed of six isoprene units with the molecular formula C30H48; they may also be thought of as consisting of three terpene units. Animals, plants and fungi all produce triterpenes, including squalene, the pre ...
mimic the insect molting hormone
ecdysone Ecdysone is a prohormone of the major insect molting hormone 20-hydroxyecdysone, secreted from the prothoracic glands. It is of steroidal structure. Insect molting hormones (ecdysone and its homologues) are generally called ecdysteroids. Ecdy ...
, disrupting molting and development and is often lethal. They are usually found in
citrus fruit ''Citrus'' is a genus of flowering plant, flowering trees and shrubs in the family Rutaceae. Plants in the genus produce citrus fruits, including important crops such as Orange (fruit), oranges, Mandarin orange, mandarins, lemons, grapefruits, ...
, and produce a bitter substance called limonoid that deters insect feeding. *
Glycosides In chemistry, a glycoside is a molecule in which a sugar is bound to another functional group via a glycosidic bond. Glycosides play numerous important roles in living organisms. Many plants store chemicals in the form of inactive glycosides. ...
are made of one or more sugars combined with a non-sugar like
aglycone An aglycone (aglycon or genin) is the chemical compound remaining after the glycosyl group on a glycoside is replaced by a hydrogen atom. For example, the aglycone of a cardiac glycoside would be a steroid A steroid is an organic compoun ...
, which usually determines the level of
toxicity Toxicity is the degree to which a chemical substance or a particular mixture of substances can damage an organism. Toxicity can refer to the effect on a whole organism, such as an animal, bacteria, bacterium, or plant, as well as the effect o ...
.
Cyanogenic In chemistry, cyanide () is an inorganic chemical compound that contains a functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. Salt (chemistry), Ionic cyanides contain the cyanid ...
glycosides are found in many plant seeds like
cherries A cherry is the fruit of many plants of the genus ''Prunus'', and is a fleshy drupe (stone fruit). Commercial cherries are obtained from cultivars of several species, such as the sweet ''Prunus avium'' and the sour ''Prunus cerasus''. The name ...
,
apples An apple is a round, edible fruit produced by an apple tree (''Malus'' spp.). Fruit trees of the orchard or domestic apple (''Malus domestica''), the most widely grown in the genus, are agriculture, cultivated worldwide. The tree originated ...
, and
plums A plum is a fruit of some species in ''Prunus'' subg. ''Prunus'.'' Dried plums are often called prunes, though in the United States they may be labeled as 'dried plums', especially during the 21st century. Plums are likely to have been ...
. Cyanogenic glycosides produce
cyanide In chemistry, cyanide () is an inorganic chemical compound that contains a functional group. This group, known as the cyano group, consists of a carbon atom triple-bonded to a nitrogen atom. Ionic cyanides contain the cyanide anion . This a ...
and are extremely poisonous. Cardenolides have a bitter taste and influence NA+/K+ activated
ATPases ATPases (, Adenosine 5'-TriPhosphatase, adenylpyrophosphatase, ATP monophosphatase, triphosphatase, ATP hydrolase, adenosine triphosphatase) are a class of enzymes that catalysis, catalyze the decomposition of adenosine triphosphate, ATP into a ...
in human heart, they may slow or strengthen the heart rate.
Saponins Saponins (Latin ''sapon'', 'soap' + ''-in'', 'one of') are bitter-tasting, usually toxic plant-derived secondary metabolites. They are Organic compound, organic chemicals that become foamy when agitated in water and have high Molar mass, molecul ...
have lipid- and water-soluble components with detergent properties. Saponins form complexes with
sterols A sterol is any organic compound with a Skeletal formula, skeleton closely related to Cholestanol, cholestan-3-ol. The simplest sterol is gonan-3-ol, which has a formula of , and is derived from that of gonane by replacement of a hydrogen atom on ...
and interfere with their uptake.


Phenolics

Phenolics are made of a hydroxyl group bonded to an aromatic
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and Hydrophobe, hydrophobic; their odor is usually fain ...
.
Furanocoumarin The furanocoumarins, or furocoumarins, are a class of organic chemical compounds produced by a variety of plants. Most of the plant species found to contain furanocoumarins belong to a handful of plant families. The families Apiaceae and Rutacea ...
is a phototoxic phenolic, and is non-toxic until activated by light. Furanocoumarin blocks the transcription and repair of
DNA Deoxyribonucleic acid (; DNA) is a polymer composed of two polynucleotide chains that coil around each other to form a double helix. The polymer carries genetic instructions for the development, functioning, growth and reproduction of al ...
.
Tannins Tannins (or tannoids) are a class of astringent, polyphenolic biomolecules that bind to and precipitate proteins and various other organic compounds including amino acids and alkaloids. The term ''tannin'' is widely applied to any large po ...
are another group of phenolics important in
tanning leather Tanning may refer to: *Tanning (leather), treating animal skins to produce leather *Sun tanning, using the sun to darken pale skin **Indoor tanning, the use of artificial light in place of the sun **Sunless tanning, application of a stain or dye t ...
. Lignins, also a group of phenolics, are the most common compounds on Earth, and help conduct water in plant stems and fill spaces in the cell.


Substances toxic to plants


Herbicides

Herbicide Herbicides (, ), also commonly known as weed killers, are substances used to control undesired plants, also known as weeds.EPA. February 201Pesticides Industry. Sales and Usage 2006 and 2007: Market Estimates. Summary in press releasMain page f ...
s usually interfere with plant growth and often imitate plant hormones. *ACCase Inhibitors kill grasses and inhibit the first step in lipid synthesis,
acetyl-CoA carboxylase Acetyl-CoA carboxylase (ACC) is a biotin-dependent enzyme () that catalyzes the irreversible carboxylation of acetyl-CoA to produce malonyl-CoA through its two catalytic activities, biotin carboxylase (BC) and carboxyltransferase (CT). ACC ...
, thus affecting cell membrane production in the meristems. They do not affect dicots plants. *ALS Inhibitors affect grasses and dicots by inhibiting the first step in some amino acid synthesis, acetolactate synthesis. The plants are slowly starved of these amino acids and eventually DNA synthesis stops. *ESPS Inhibitors affect grasses and dicots by inhibiting the first step in the synthesis of
tryptophan Tryptophan (symbol Trp or W) is an α-amino acid that is used in the biosynthesis of proteins. Tryptophan contains an α-amino group, an α-carboxylic acid group, and a side chain indole, making it a polar molecule with a non-polar aromat ...
,
phenylalanine Phenylalanine (symbol Phe or F) is an essential α-amino acid with the chemical formula, formula . It can be viewed as a benzyl group substituent, substituted for the methyl group of alanine, or a phenyl group in place of a terminal hydrogen of ...
and
tyrosine -Tyrosine or tyrosine (symbol Tyr or Y) or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a conditionally essential amino acid with a polar side group. The word "tyrosine" is ...
, enolpyruvylshikimate 3-phosphate synthase enzyme. *
Photosystem II Photosystem II (or water-plastoquinone oxidoreductase) is the first protein complex in the light-dependent reactions of oxygenic photosynthesis. It is located in the thylakoid membrane of plants, algae, and cyanobacteria. Within the photosystem ...
Inhibitors reduce the
electron The electron (, or in nuclear reactions) is a subatomic particle with a negative one elementary charge, elementary electric charge. It is a fundamental particle that comprises the ordinary matter that makes up the universe, along with up qua ...
flow from water to NADPH2+ causing electrons to accumulate on
chlorophyll Chlorophyll is any of several related green pigments found in cyanobacteria and in the chloroplasts of algae and plants. Its name is derived from the Greek words (, "pale green") and (, "leaf"). Chlorophyll allows plants to absorb energy ...
molecules and excess
oxidation Redox ( , , reduction–oxidation or oxidation–reduction) is a type of chemical reaction in which the oxidation states of the reactants change. Oxidation is the loss of electrons or an increase in the oxidation state, while reduction is ...
to occur. The plant will eventually die. *Synthetic
Auxin Auxins (plural of auxin ) are a class of plant hormones (or plant-growth regulators) with some morphogen-like characteristics. Auxins play a cardinal role in coordination of many growth and behavioral processes in plant life cycles and are essent ...
mimics plant hormones and can affect the plant cell membrane.


Bacterial phytotoxins

* Tabtoxin is produced by '' Pseudomonas syringae pv. tabaci'' that may cause toxic concentrations of
ammonia Ammonia is an inorganic chemical compound of nitrogen and hydrogen with the chemical formula, formula . A Binary compounds of hydrogen, stable binary hydride and the simplest pnictogen hydride, ammonia is a colourless gas with a distinctive pu ...
to build up. This buildup of ammonia causes leaf
chlorosis In botany, chlorosis is a condition in which leaves produce insufficient chlorophyll. As chlorophyll is responsible for the green color of leaves, chlorotic leaves are pale, yellow, or yellow-white. The affected plant has little or no ability to ...
.Strobel, Gary A. 1977. Annual Review Microbiology "Bacterial Phytotoxins. 31:205-224 *Glycopeptides are produced by a number of bacteria and have been indicated in disease development. A glycopeptide from ''Corynebacterium sepedonicum'' causes rapid wilt and marginal
necrosis Necrosis () is a form of cell injury which results in the premature death of cells in living tissue by autolysis. The term "necrosis" came about in the mid-19th century and is commonly attributed to German pathologist Rudolf Virchow, who i ...
. A toxin from ''Corynebacterium insidiosum'' causes plugging of the plant stem interfering with water movement between cells. Amylovorin is a
polysaccharide Polysaccharides (), or polycarbohydrates, are the most abundant carbohydrates found in food. They are long-chain polymeric carbohydrates composed of monosaccharide units bound together by glycosidic linkages. This carbohydrate can react with wat ...
from '' Erwinia amylovora'' and causes wilting in rosaceous plants. A polysaccharide from '' Xanthomonas campestris'' obstructs water flow through
phloem Phloem (, ) is the living tissue in vascular plants that transports the soluble organic compounds made during photosynthesis and known as ''photosynthates'', in particular the sugar sucrose, to the rest of the plant. This transport process is ...
causing black rot in cabbage. *Phaseolotoxin is a modified tripeptide δ-(N′-sulfodiaminophosphinyl)-ornithyl-alanyl-homoarginineproduced by certains strains of ''Pseudomonas syringae'' pv. ''phaseolicola'', ''Pseudomonas syringae'' pv. ''actinidiae'' and strain ''Pseudomonas syringae'' pv. ''syringae'' CFBP 3388. Phaseolotoxin is a reversible inhibitor of the enzyme ornithine carbamoyltransferase (OCTase; EC 2.1.3.3), which catalyzes the formation of citrulline from ornithine and carbamoylphosphate in the arginine biosynthetic pathway. Phaseolotoxin is an effective inhibitor of OCTase activity from plant, mammalian, and bacterial sources and causes a phenotypic requirement for arginine. Additionally, phaseolotoxin inhibits the enzyme ornithine decarboxylase (EC 4.1.1.17), which is involved in the biosynthesis of
polyamine A polyamine is an organic compound having two or more amino groups. Alkyl polyamines occur naturally, but some are synthetic. Alkylpolyamines are colorless, hygroscopic, and water soluble. Near neutral pH, they exist as the ammonium derivatives. ...
s.Bachmann AS, Matile P, Slusarenko AJ, 1998. Inhibition of ornithine decarboxylase activity by phaseolotoxin: Implications for symptom production in halo blight of French bean. Physiological and Molecular Plant Pathology 53, 287-299. *Rhizobiotoxine, produced by '' Rhizobium japonicum'', causes the root nodules of some soy bean plants to become chlorotic.


See also

* *


References

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