Qinghaosu

New chemistry of quinghao, a marvelous herb of antiquity, and antimalarial trioxane qinghaosu 97ACR73. 

Liu H. J., Chew S. Y., Yeh W. L. Facile Selective Diels-Alder Reactions of Chiral 5,5-Dimethyl-4,6-Methano-2-Methoxycarbonyl-2-Cyclohexenone. Application to the Total Synthesis of Qinghaosu. Youji Huaxue 1993 13 314 321 Keywords (-)-/f-pinene, asymmetric synthesis... 

Classen, W., Altmann, B., Gretener, P., Souppart, C., Skelton-Stroud, P. and Krinke, G. (1999) Differential effects of orally versus parenterally administered qinghaosu derivative artemether in dogs. Experimental and Toxicologic Pathology, 51, 507-516. 

A new medicine that seems to be promising in this field is artimisinine (19) isolated from Artimisia annua. Extracts of this plant have been known for centuries in Chinese folk medicine under the name of Qinghaosu or Qinghao. For solubility reasons and hydrolysis stability, artimisinine is converted via the dihydro compound into water-soluble artesunate or oil soluble artemether and arteether (Scheme 5.12) [43]. 

Klayman DL. (1985) Qinghaosu (Artemisinin) — an antimalarial drug from China. Science 228 1049-1055. 

Zheng MY, Li L, Chen SF. (1983) Chemical transformations of qinghaosu, a peroxidic antimalarial. Tetrahedron 39 2941-2946. 

Zhao SS, Zeng MY. (1985) Spektrometrische Hochdruck-Fliissigkeits-Chromatographische (HPLC) Untersuchungen zur Analytik von Qinghaosu. Planta Med 51 233-237. 

The success in determining the chemical structure of qinghaosu is only one example of the accomplishments of chemists in attaining a better understanding of the relationship between the chemical structure of natural drugs and their pharmacological effects. Those accomplishments have formed the basis of a whole new phase of the pharmaceutical industry in which natural products and their derivatives provide an extensive source of new drugs. 

Artemisinin ( qinghaosu ) (18), a sesquiterpene lactone antimalarial compound with an endoperoxide group, discovered in the Peoples Republic of China as a constituent of Artemisia annua L., has created great interest in the biomedical community, owing to its unique mechanism of action on the heme complex. Artemisinin serves as an option for the treatment of chloroquine (4l)-resistant malaria and is used in some Asian countries as an antimalarial. However, the use of artemisinin as a single agent anti-malarial is a potential risk since the malaria parasite may become resistant to this compound class. 

Li Y, Wu YL, How Chinese scientists discovered qinghaosu (artemisinin) and developed its derivatives. What are the future perspectives Med Trap (Mars) 58 9-12, 1998. 

Isotopically labeled artemisinin or hydroxylated derivatives thereof, which are required in order to investigate the metabolism of qinghaosu, have been prepared starting from... 

The isolation and structural determination of the naturally occurring potent antimalar-ial sesquiterpene endoperoxides, artemisinin (qinghaosu) (6)28-31.439 recogni-... 

In 1972, Chinese researchers isolated, by extraction at low temperature from a plant, a crystalline compound that they named qinghaosu [the name artemisinin (la) is preferred by Chemical Abstracts, RN 63968-64-9]. The plant source of artemisinin is a herb, Artemisia annua (Sweet wormwood), and the fact that artemisinin is a stable, easily crystallizable compound renders the extraction and purification processes reasonably straightforward. The key pharmacophore of this natural product is the 1,2,4-trioxane unit (2) and, in particular, the endoperoxide bridge. Reduction of the peroxide bridge to an ether provides an analogue, deoxyartemisinin 3, that is devoid of antimalarial activity. ... 

Artemisinin (qinghaosu) antimalarial activity, 1309, 1313 biological targets, 1311-13 ESR spin-trapping agents, 1291 Feai) degradation, 1283, 1293, 1295-6 heme adducts, 1298, 1311-12 heterolyhc cleavage of peroxide bond, 1301-2, 1309... 

QCISD, density functional theory, 3, 34-5, 43 Qinghaosu see Artemisinin (qinghaosu) Quahty, deterioration evaluation, 656, 664 Quantum chemical calculations,... 

A very well-studied compound which falls within the remit of this chapter is the natural product, artemisinin 9a, the traditional Chinese medicine known as qinghaosu. In this chapter, as in the CHEC-II(1996) chapter <1996GHEC-II(7)625>, we will not attempt to provide a full account of artemisinin research, but the main features of its unique, 3/7,677-pyrano[2,3-( ]-l,2,4-trioxine, ring system will be summarized. 

White NJ Qinghaosu (artemisinin) The price of success. Science 2008 320 330. [PMID 18420924]... 

Anonymous. 1992. Rediscovering wormwood qinghaosu for malaria. Lancet. March 14, 1992. p. 649-651. 

Artemisinin 1, a naturally occurring sesquiterpene peroxy-lactone, has been isolated in up to 0.25% yield from the dry leaves of Artemisia annua L.1 Interest in artemisinin is based on its phytomedicinal properties. In 168 b.c. China, as described in a Treatment of 52 Sicknesses, the leaves of A. annua (Qinghao) were used for the treatment of chills and fever.2 It was not until 1972 that the active antimalarial agent qinghaosu was isolated in pure form. This allowed for the unequivocal elucidation of its structure through the use of x-ray crystallography. This complex tetracyclic peroxide is now referred to as artemisinin in various sources such as Chemical Abstracts or the Merck Index. 

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