Names | |
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IUPAC name 12α,13-Epoxytrichothec-9-ene-4β,15-diyl diacetate | |
Systematic IUPAC name (2R,2′S,4R,5S,5aR,9aR)-5a-[(Acetyloxy)methyl]-5,8-dimethyl-2,3,4,5,5a,6,7,9a-octahydrospiro[[2,5]methano[1]benzoxepine-10,2′-oxiran]-4-yl acetate | |
Other names 12,13-Epoxy-trichothec-9-ene-4,15-diol diacetate; 4,15-Diacetylverrucarol; Antibiotic A 2; Di-O-acetylverrucarol | |
Identifiers | |
3D model (JSmol) | |
ChemSpider | |
ECHA InfoCard | 100.164.354 |
PubChem CID | |
CompTox Dashboard (EPA) | |
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Properties | |
C19H26O6 | |
Molar mass | 350.411 g·mol−1 |
Hazards | |
GHS labelling: | |
Warning | |
H300, H310, H315, H319, H330, H335 | |
P260, P261, P262, P264, P270, P271, P280, P284, P301+P310, P302+P350, P302+P352, P304+P340, P305+P351+P338, P310, P312, P320, P321, P322, P330, P332+P313, P337+P313, P361, P362, P363, P403+P233, P405, P501 | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
Diacetylverrucarol is a natural trichothecene produced by the fungus Myrothecium verrucaria . Chemically, it is an acetate derivative of verrucarol.
Trichothecenes have been found to cause growth retardation, wilting, chlorosis, and necrosis in some plants. [1] It can work in poor conditions, even where there is very little or no moisture. Diacetylverrucarol is undergoing study for its successful effects at reducing or killing the kudzu weed. It is prepared through liquid fermentation of Myrothecium verrucaria mycelium after which it can be used as a pesticide. This causes very little harm to the plants that the kudzu plant displaces. Results appeared within 24 hours and the kudzu plant's roots were diseased after 14 days. In greenhouse experiments the fungus killed 100 percent of the kudzu seeds, and, in outdoor trials, 90-100 percent of older plants. The fungus is undergoing study to reduce the diacetylverrucarol presence to reduce side effects. [2]
Because it is a trichothecene, it has significant toxicity. If swallowed by humans, the initial symptoms are general discomfort, dry eyes, and drowsiness. If a larger dose is consumed, symptoms of a hemorrhagic fever will occur, as well as mental impairment. Other animals are susceptible as well, and can experience growth retardation, reproductive disorders, and vomiting if the substance is consumed. [1] [3]
Kudzu is a group of climbing, coiling, and trailing deciduous perennial vines native to much of East Asia, Southeast Asia, and some Pacific islands, but invasive in many parts of the world, primarily North America.
Pueraria montana is a species of plant in the botanical family Fabaceae. At least three sub-species are known. It is closely related to other species in the genus Pueraria and the common name kudzu is used for all of these species and hybrids between them. The morphological differences between them are subtle, they can breed with each other, and it appears that introduced kudzu populations in the United States have ancestry from more than one of the species.
Mycoprotein is a form of single-cell protein, also known as fungal protein, derived from fungi for human consumption. The only commercial mycoprotein is marketed under the brand name Quorn, currently sold in 17 countries. It is a fermented product with a doughy consistency and slight mushroom flavor.
A mycotoxin is a toxic secondary metabolite produced by organisms of kingdom Fungi and is capable of causing disease and death in both humans and other animals. The term 'mycotoxin' is usually reserved for the toxic chemical products produced by fungi that readily colonize crops.
Fusarium/fjuˈzɛəriəm/ (help·info) is a large genus of filamentous fungi, part of a group often referred to as hyphomycetes, widely distributed in soil and associated with plants. Most species are harmless saprobes, and are relatively abundant members of the soil microbial community. Some species produce mycotoxins in cereal crops that can affect human and animal health if they enter the food chain. The main toxins produced by these Fusarium species are fumonisins and trichothecenes. Despite most species apparently being harmless, some Fusarium species and subspecific groups are among the most important fungal pathogens of plants and animals.
T-2 mycotoxin is a trichothecene mycotoxin. It is a naturally occurring mold byproduct of Fusarium spp. fungus which is toxic to humans and animals. The clinical condition it causes is alimentary toxic aleukia and a host of symptoms related to organs as diverse as the skin, airway, and stomach. Ingestion may come from consumption of moldy whole grains. T-2 can be absorbed through human skin. Although no significant systemic effects are expected after dermal contact in normal agricultural or residential environments, local skin effects can not be excluded. Hence, skin contact with T-2 should be limited.
Sooty mold is a collective term for different Ascomycete fungi, which includes many genera, commonly Cladosporium and Alternaria. It grows on plants and their fruit, but also environmental objects, like fences, garden furniture, stones, and even cars. The mold benefits from either a sugary exudate produced by the plant or fruit, or honeydew-secreting insects or sap suckers the plant may be infested by.
Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug. The molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).
Athelia rolfsii is a corticioid fungus in the family Atheliaceae. It is a facultative plant pathogen and is the causal agent of "southern blight" disease in crops.
Gibberella zeae, also known by the name of its anamorph Fusarium graminearum, is a fungal plant pathogen which causes fusarium head blight (FHB), a devastating disease on wheat and barley. The pathogen is responsible for billions of dollars in economic losses worldwide each year. Infection causes shifts in the amino acid composition of wheat, resulting in shriveled kernels and contaminating the remaining grain with mycotoxins, mainly deoxynivalenol (DON), which inhibits protein biosynthesis; and zearalenone, an estrogenic mycotoxin. These toxins cause vomiting, liver damage, and reproductive defects in livestock, and are harmful to humans through contaminated food. Despite great efforts to find resistance genes against F. graminearum, no completely resistant variety is currently available. Research on the biology of F. graminearum is directed towards gaining insight into more details about the infection process and reveal weak spots in the life cycle of this pathogen to develop fungicides that can protect wheat from scab infection.
Myrothecium verrucaria is a species of fungus in the order Hypocreales. A plant pathogen, it is common throughout the world, often found on materials such as paper, textiles, canvas and cotton. It is a highly potent cellulose decomposer.
Verticillium longisporum, also known as Verticillium Wilt, is a fungal plant pathogen that commonly infects canola. V. longisporum can attack other brassica plants as well as woody ornamentals. A main symptom of the infected plant is wilting. In America, V. longsiporum primarily effects eudicot plants. This pathogen can be very devastating and hard to eradicate, responding only to expensive fumigation or fungal resistant plants.
Vomitoxin, also known as deoxynivalenol (DON), is a type B trichothecene, an epoxy-sesquiterpenoid. This mycotoxin occurs predominantly in grains such as wheat, barley, oats, rye, and corn, and less often in rice, sorghum, and triticale. The occurrence of deoxynivalenol is associated primarily with Fusarium graminearum and F. culmorum, both of which are important plant pathogens which cause fusarium head blight in wheat and gibberella or fusarium ear blight in corn. The incidence of fusarium head blight is strongly associated with moisture at the time of flowering (anthesis), and the timing of rainfall, rather than the amount, is the most critical factor. However, increased amount of moisture towards harvest time has been associated with lower amount of vomitoxin in wheat grain due to leaching of toxins. Furthermore, deoxynivalenol contents are significantly affected by the susceptibility of cultivars towards Fusarium species, previous crop, tillage practices, and fungicide use. It occurs abundantly in grains in Norway due to heavy rainfall.
Red thread disease is a fungal infection found on lawns and other turfed areas. It is caused by the corticioid fungus Laetisaria fuciformis and has two separate stages. The stage that gives the infection its name is characterised by very thin, red, needle-like strands extending from the grass blade. These are stromata, which can remain viable in soil for two years. After germinating, the stromata infect grass leaf blades through their stomata. The other stage is visible as small, pink, cotton wool-like mycelium, found where the blades meet. It is common when both warmth and humidity are high.
Kudzu is an invasive plant species in the United States, introduced from Asia with devastating environmental consequences, earning it the nickname "the vine that ate the South". It has been spreading rapidly in the Southern United States, "easily outpacing the use of herbicide, spraying, and mowing, as well increasing the costs of these controls by $6 million annually". Estimates of the vine's spread vary, from the United States Forest Service's 2015 estimate of 2,500 acres per year to the Department of Agriculture's estimate of as much as 150,000 acres annually.
Podostroma cornu-damae, also known as the poison fire coral, is a species of fungus in the family Hypocreaceae. The fruit bodies of the fungus are highly toxic, and have been responsible for several fatalities in Japan. The fungus contains several trichothecene mycotoxins.
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.
Undernutrition in children, occurs when children do not consume enough calories, protein, or micronutrients to maintain good health. It is common globally and may result in both short and long term irreversible adverse health outcomes. Undernutrition is sometimes used synonymously with malnutrition, however, malnutrition could mean both undernutrition or overnutrition. The World Health Organization (WHO) estimates that malnutrition accounts for 54 percent of child mortality worldwide, which is about 1 million children. Another estimate, also by WHO, states that childhood underweight is the cause for about 35% of all deaths of children under the age of five worldwide.
Trichothecium roseum is a fungus in the division Ascomycota first reported in 1809. It is characterized by its flat and granular colonies which are initially white and develop to be light pink in color. This fungus reproduces asexually through the formation of conidia with no known sexual state. Trichothecium roseum is distinctive from other species of the genus Trichothecium in its characteristic zigzag patterned chained conidia. It is found in various countries worldwide and can grow in a variety of habitats ranging from leaf litter to fruit crops. Trichothecium roseum produces a wide variety of secondary metabolites including mycotoxins, such as roseotoxins and trichothecenes, which can infect and spoil a variety of fruit crops. It can act as both a secondary and opportunistic pathogen by causing pink rot on various fruits and vegetables and thus has an economical impact on the farming industry. Secondary metabolites of T. roseum, specifically Trichothecinol A, are being investigated as potential anti-metastatic drugs. Several agents including harpin, silicon oxide, and sodium silicate are potential inhibitors of T. roseum growth on fruit crops. Trichothecium roseum is mainly a plant pathogen and has yet to show a significant impact on human health.
Nivalenol (NIV) is a mycotoxin of the trichothecene group. In nature it is mainly found in fungi of the Fusarium species. The Fusarium species belongs to the most prevalent mycotoxin producing fungi in the temperate regions of the northern hemisphere, therefore making them a considerable risk for the food crop production industry.