Thermal rearrangement and decomposition products of artemisinin (qinghaosu)

Lin, Ai Jeng; Klayman, Daniel L.; Hoch, James M.; Silverton, J. V.; George, Clifford

doi:10.1021/jo00223a017

Cited by 92 publications

(81 citation statements)

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“…Unlike ascaridole, which is very sensitive to heat (31), QHS shows a remarkable thermal stability. It does not explode at its melting point, as one might expect, but rather can exist unchanged for about 3 minutes at 50°C above its melting point and can be purified by sublimation (32).…”

Section: Ch3mentioning

confidence: 92%

Qinghaosu (Artemisinin): an Antimalarial Drug from China

Klayman

1985

Science

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The herb Artemisia annua has been used for many centuries in Chinese traditional medicine as a treatment for fever and malaria. In 1971, Chinese chemists isolated from the leafy portions of the plant the substance responsible for its reputed medicinal action. This compound, called qinghaosu (QHS, artemisinin), is a sesquiterpene lactone that bears a peroxide grouping and, unlike most other antimalarials, lacks a nitrogen-containing heterocyclic ring system. The compound has been used successfully in several thousand malaria patients in China, including those with both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum . Derivatives of QHS, such as dihydroqinghaosu, artemether, and the water-soluble sodium artesunate, appear to be more potent than QHS itself. Sodium artesunate acts rapidly in restoring to consciousness comatose patients with cerebral malaria. Thus QHS and its derivatives offer promise as a totally new class of antimalarials.

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Section: Ch3mentioning

confidence: 92%

Qinghaosu (Artemisinin): an Antimalarial Drug from China

Klayman

1985

Science

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“…Artemisinin can be easily extracted with petroleum ether (bp ¼ 458C), hexane (bp ¼ 608C), or other miscible solvents such as chloroform, acetonitrile and ether which have boiling points lower than the critical temperature for artemisinin stability. Artemisinin was established to be stable up to 1508C in neutral solvents (Lin et al, 1985). However, during tea preparation artemisinin decreases when leaves are boiled for as little as 5 min, but seems to remain stable if leaves are extracted with water before the boiling point (Magalhães, 1996).…”

Section: Laboratory and Commercial Extraction Of Artemisininmentioning

confidence: 99%

Cultivation and genetics ofArtemisia annuaL. for increased production of the antimalarial artemisinin

Ferreira¹,

Laughlin²,

Delabays

et al. 2005

Plant Genet. Resour.

111

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Malaria has been treated for over 350 years with quinine and quinine-derived drugs. However, in several areas of the world, some strains of the malarial parasite Plasmodium falciparum have developed resistance against these drugs. Recently, the World Health Organization (WHO) recommended the use of artemisinin-combination treatments (ACT) as the first-line treatment for multidrug-resistant falciparum malaria. The WHO estimates that current supplies of artemisinin are sufficient for only 30 million ACT, and is foreseeing the need for 130-220 million ACT in 2005 (WHO, 2004. Current research on the production of synthetic artemisinin-like compounds by the Roll Back Malaria project, pharmaceutical companies and academia resulted in a promising synthetic artemisinin-like compound (OZ277) which is currently undergoing phase I clinical trials. In about 5 years this drug is expected to be approved and made available to the public, however, meeting current global demands for ACT depends on the immediate availability of affordable artemisinin-derived drugs. This will involve expansion of the area under cultivation of Artemisia annua and improved methods of cultivation and processing of raw material, associated with more efficient methods for extraction and purification of artemisinin from plant material. This review addresses the agricultural, environmental and genetic aspects that may be useful in the successful large-scale cultivation of A. annua and for producing the antimalarial artemisinin in areas where it is urgently needed today. It also includes geographic aspects (latitude and altitude), which will help make decisions about crop establishment in tropical countries, and includes a list of Good Agricultural and Collection Practices for A. annua.

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“…The metabolism, chemical transformation, thermal rearrangement and decomposition studies of artemisinin were well established [3,4]. Among known antimalarial compounds, artemisinin has a novel structure with a unique 1,2,4-trioxane ring system.…”

Section: Introductionmentioning

confidence: 99%

Biotransformation of Artemisinin Mediated through Fungal Strains for Obtaining Derivatives with Novel Activities

et al. 2009

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Artemisinin, a sesquiterpene lactone, is the active antimalarial constituent of Artemisia annua. Several fungal strains Saccharomyces cerevisiae, Aspergillus flavus, Aspergillus niger and Picchia pastoris were used to biotransform artemisinin. Among these strains, A. flavus was the only microorganism capable of transforming artemisinin to deoxyartemisinin in higher yields than the previous reports. The structure of deoxyartemisinin was elucidated by spectroscopy. Deoxyartemisinin showed antibacterial activity against Staphylococcus aureus, S. epidermidis and S. mutans at a minimum inhibitory concentration (MIC) of 1 mg/mL compared to artemisinin whose MIC was >2 mg/mL. Keywords

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Thermal rearrangement and decomposition products of artemisinin (qinghaosu)

Cited by 92 publications

References 0 publications

Qinghaosu (Artemisinin): an Antimalarial Drug from China

Qinghaosu (Artemisinin): an Antimalarial Drug from China

Cultivation and genetics ofArtemisia annuaL. for increased production of the antimalarial artemisinin

Biotransformation of Artemisinin Mediated through Fungal Strains for Obtaining Derivatives with Novel Activities

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