Diacetoxyscirpenol

Last updated
Diacetoxyscirpenol
Diacetoxyscirpenol.svg
Names
IUPAC name
3α-Hydroxy-12α,13-epoxy-trichothec-9-ene-4β,15-diyl diacetate
Systematic IUPAC name
(2R,2′R,3R,4S,5S,5aR,9aR)-5a-[(Acetyloxy)methyl]-3-hydroxy-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
anguidine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.159 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C19H26O7/c1-10-5-6-18(8-23-11(2)20)13(7-10)26-16-14(22)15(25-12(3)21)17(18,4)19(16)9-24-19/h7,13-16,22H,5-6,8-9H2,1-4H3/t13-,14-,15-,16-,17-,18-,19-/m1/s1
    Key: AUGQEEXBDZWUJY-ZLJUKNTDSA-N
  • CC1=C[C@@H]2[C@](CC1)([C@]3([C@@H]([C@H]([C@H]([C@]34CO4)O2)O)OC(=O)C)C)COC(=O)C
Properties
C19H26O7
Molar mass 366.410 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Diacetoxyscirpenol (DAS), also called anguidine, is a mycotoxin from the group of type A trichothecenes. It is a secondary metabolite product of fungi of the genus Fusarium and may cause toxicosis in farm animals. [1] The US Health and Human Services agency considers it a select agent for research purposes. [2]

Related Research Articles

<span class="mw-page-title-main">Biological warfare</span> Use of strategically designed biological weapons

Biological warfare, also known as germ warfare, is the use of biological toxins or infectious agents such as bacteria, viruses, insects, and fungi with the intent to kill, harm or incapacitate humans, animals or plants as an act of war. Biological weapons are living organisms or replicating entities. Entomological (insect) warfare is a subtype of biological warfare.

<span class="mw-page-title-main">Bioterrorism</span> Terrorism involving biological agents

Bioterrorism is terrorism involving the intentional release or dissemination of biological agents. These agents include bacteria, viruses, insects, fungi, and/or toxins, and may be in a naturally occurring or a human-modified form, in much the same way as in biological warfare. Further, modern agribusiness is vulnerable to anti-agricultural attacks by terrorists, and such attacks can seriously damage economy as well as consumer confidence. The latter destructive activity is called agrobioterrorism and is a subtype of agro-terrorism.

<span class="mw-page-title-main">Toxin</span> Naturally occurring organic poison

A toxin is a naturally occurring organic poison produced by metabolic activities of living cells or organisms. They occur especially as proteins, often conjugated. The term was first used by organic chemist Ludwig Brieger (1849–1919) and is derived from the word "toxic".

<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">Botulinum toxin</span> Neurotoxic protein produced by Clostridium botulinum

Botulinum toxin, or botulinum neurotoxin (BoNT), is a neurotoxic protein produced by the bacterium Clostridium botulinum and related species. It prevents the release of the neurotransmitter acetylcholine from axon endings at the neuromuscular junction, thus causing flaccid paralysis. The toxin causes the disease botulism. The toxin is also used commercially for medical and cosmetic purposes.

<span class="mw-page-title-main">Ricin</span> Type of toxic lectin

Ricin ( RY-sin) is a lectin (a carbohydrate-binding protein) and a highly potent toxin produced in the seeds of the castor oil plant, Ricinus communis. The median lethal dose (LD50) of ricin for mice is around 22 micrograms per kilogram of body weight via intraperitoneal injection. Oral exposure to ricin is far less toxic. An estimated lethal oral dose in humans is approximately 1 milligram per kilogram of body weight.

<span class="mw-page-title-main">Tetrodotoxin</span> Neurotoxin

Tetrodotoxin (TTX) is a potent neurotoxin. Its name derives from Tetraodontiformes, an order that includes pufferfish, porcupinefish, ocean sunfish, and triggerfish; several of these species carry the toxin. Although tetrodotoxin was discovered in these fish and found in several other animals, it is actually produced by certain infecting or symbiotic bacteria like Pseudoalteromonas, Pseudomonas, and Vibrio as well as other species found in animals.

<span class="mw-page-title-main">Foodborne illness</span> Illness from eating spoiled food

Foodborne illness is any illness resulting from the spoilage of contaminated food by pathogenic bacteria, viruses, or parasites that contaminate food, as well as prions, and toxins such as aflatoxins in peanuts, poisonous mushrooms, and various species of beans that have not been boiled for at least 10 minutes.

<span class="mw-page-title-main">Biological agent</span> Pathogen that can be weaponized

A biological agent is a bacterium, virus, protozoan, parasite, fungus, or toxin that can be used purposefully as a weapon in bioterrorism or biological warfare (BW). In addition to these living or replicating pathogens, toxins and biotoxins are also included among the bio-agents. More than 1,200 different kinds of potentially weaponizable bio-agents have been described and studied to date.

<span class="mw-page-title-main">T-2 mycotoxin</span> Chemical compound

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.

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

Abrin is an extremely toxic toxalbumin found in the seeds of the rosary pea, Abrus precatorius. It has a median lethal dose of 0.7 micrograms per kilogram of body mass when given to mice intravenously. The median toxic dose for humans ranges from 10 to 1000 micrograms per kilogram when ingested and is 3.3 micrograms per kilogram when inhaled.

Yellow rain was a 1981 political incident in which the United States Secretary of State Alexander Haig accused the Soviet Union of supplying T-2 mycotoxin to the communist states in Vietnam, Laos and Cambodia for use in counterinsurgency warfare. Refugees described many different forms of "attacks", including a sticky yellow liquid falling from planes or helicopters, which was dubbed "yellow rain". The U.S. government alleged that over ten thousand people had been killed in attacks using these supposed chemical weapons. The Soviets denied these claims and an initial United Nations investigation was inconclusive.

Under United States law, Biological select agents or toxins (BSATs) — or simply select agents for short — are bio-agents which have been declared by the U.S. Department of Health and Human Services (HHS) or by the U.S. Department of Agriculture (USDA) to have the "potential to pose a severe threat to public health and safety". The agents are divided into (1) HHS select agents and toxins affecting humans; (2) USDA select agents and toxins affecting agriculture; and (3) overlap select agents and toxins affecting both.

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

The trichothecenes are a large family of chemically related mycotoxins. They are produced by various species of Fusarium, Myrothecium, Trichoderma/Podostroma, Trichothecium, Cephalosporium, Verticimonosporium, and Stachybotrys. Chemically, trichothecenes are a class of sesquiterpenes.

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

Zearalenone (ZEN), also known as RAL and F-2 mycotoxin, is a potent estrogenic metabolite produced by some Fusarium and Gibberella species. Specifically, the Gibberella zeae, the fungal species where zearalenone was initially detected, in its asexual/anamorph stage is known as Fusarium graminearum. Several Fusarium species produce toxic substances of considerable concern to livestock and poultry producers, namely deoxynivalenol, T-2 toxin, HT-2 toxin, diacetoxyscirpenol (DAS) and zearalenone. Particularly, ZEN is produced by Fusarium graminearum, Fusarium culmorum, Fusarium cerealis, Fusarium equiseti, Fusarium verticillioides, and Fusarium incarnatum. Zearalenone is the primary toxin that binds to estrogen receptors, causing infertility, abortion or other breeding problems, especially in swine. Often, ZEN is detected together with deoxynivalenol in contaminated samples and its toxicity needs to be considered in combination with the presence of other toxins.

Virulence factors are cellular structures, molecules and regulatory systems that enable microbial pathogens to achieve the following:

Microbial toxins are toxins produced by micro-organisms, including bacteria, fungi, protozoa, dinoflagellates, and viruses. Many microbial toxins promote infection and disease by directly damaging host tissues and by disabling the immune system. Endotoxins most commonly refer to the lipopolysaccharide (LPS) or lipooligosaccharide (LOS) that are in the outer plasma membrane of Gram-negative bacteria. The botulinum toxin, which is primarily produced by Clostridium botulinum and less frequently by other Clostridium species, is the most toxic substance known in the world. However, microbial toxins also have important uses in medical science and research. Currently, new methods of detecting bacterial toxins are being developed to better isolate and understand these toxin. Potential applications of toxin research include combating microbial virulence, the development of novel anticancer drugs and other medicines, and the use of toxins as tools in neurobiology and cellular biology.

<span class="mw-page-title-main">Enterotoxin type B</span>

In the field of molecular biology, enterotoxin type B, also known as Staphylococcal enterotoxin B (SEB), is an enterotoxin produced by the gram-positive bacteria Staphylococcus aureus. It is a common cause of food poisoning, with severe diarrhea, nausea and intestinal cramping often starting within a few hours of ingestion. Being quite stable, the toxin may remain active even after the contaminating bacteria are killed. It can withstand boiling at 100 °C for a few minutes. Gastroenteritis occurs because SEB is a superantigen, causing the immune system to release a large amount of cytokines that lead to significant inflammation.


The Division of Select Agents and Toxins (DSAT) of the Centers for Disease Control and Prevention is responsible for the Select Agent Program and the Etiologic Agent Import Permit Program. They inspect the laboratories of more than 300 organizations approved to use and transfer select agents, and put regulations in place to minimize risk in the use of these bacterial agents and toxins.

References

  1. Hoerr FJ, Carlton WW, Yagen B (1981). "Mycotoxicosis caused by a single dose of T-2 toxin or diacetoxyscirpenol in broiler chickens". Vet. Pathol. 18 (5): 652–664. doi: 10.1177/030098588101800510 . PMID   7281462. S2CID   22715425.
  2. "Select Agents and Toxins list".