1,2,4-trioxane in the context of "Artemisia annua"

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⭐ Core Definition: 1,2,4-trioxane

1,2,4-Trioxane is one of the isomers of trioxane. It has the molecular formula C3H6O3 and consists of a six membered ring with three carbon atoms and three oxygen atoms. The two adjacent oxygen atoms form a peroxide functional group and the other forms an ether functional group. It is like a cyclic acetal but with one of the oxygen atoms in the acetal group being replaced by a peroxide group.

1,2,4-Trioxane itself has not been isolated or characterized, but rather only studied computationally. However, it constitutes an important structural element of some more complex organic compounds. The natural compound artemisinin, isolated from the sweet wormwood plant (Artemisia annua), and some semi-synthetic derivatives are important antimalarial drugs containing the 1,2,4-trioxane ring. Completely synthetic analogs containing the 1,2,4-trioxane ring are important potential improvements over the naturally derived artemisinins. The peroxide group in the 1,2,4-trioxane core of artemisinin is cleaved in the presence of the malaria parasite leading to reactive oxygen radicals that are damaging to the parasite.

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1,2,4-trioxane in the context of Artemisinin

Artemisinin (/ˌɑːrtɪˈmiːsɪnɪn/) and its semisynthetic derivatives are a group of drugs used in the treatment of malaria due to Plasmodium falciparum. It was discovered in 1972 by Tu Youyou, who shared the 2015 Nobel Prize in Physiology or Medicine for her discovery. Artemisinin-based combination therapies (ACTs) have become standard treatment worldwide for P. falciparum malaria as well as malaria due to other species of Plasmodium. Artemisinin can be extracted from the herb Artemisia annua (sweet wormwood), which is used in traditional Chinese medicine. Alternatively, it can be prepared by a semi-synthetic method from a precursor compound that can be produced using a genetically engineered yeast, which is much more efficient than extraction from the plant.

Artemisinin and its derivatives are all sesquiterpene lactones containing an unusual peroxide bridge. This endoperoxide 1,2,4-trioxane ring is responsible for their antimalarial properties. Few other natural compounds with such a peroxide bridge are known.

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LINKED FROM (PARENTS)
← Artemisinin
LINKS TO (CHILDREN)
Isomer → Trioxane → Molecular formula → Carbon → Oxygen → Organic peroxide → Ether → Acetal → Organic compound → Artemisinin → Artemisia annua → Semi-synthetic → Antimalarial drug → Bond cleavage → Malaria → Parasitic disease → Reactive oxygen species → Radical (chemistry) →