Activity of Artemisinin-Type Compounds Against Cancer Cells
Clinical Oncology strives for complete remission of patients with cancer, but still crusades against multidrug resistance of various cancers. Scientists and clinicians have been challenged to identify new potent anticancer compounds with new targeting str
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Activity of Artemisinin-Type Compounds Against Cancer Cells Serkan Sertel, Peter K. Plinkert, and Thomas Efferth
8.1 8.1.1
Introduction Botany and Geographical Distribution
Artemisia annua L. (Chinese: 青蒿; pinyin: qı¯ngha¯o), also known as sweet annie, sweet sagewort, or armoise annuelle, belongs to the medicinal plants derived from Traditional Chinese Medicine (TCM). This annual plant belongs to the family of Asteraceae. It is native to China and grows naturally as a part of steppe vegetation in northern parts of China at 1,000–1,500 m above the sea level (Wang 1961). It has a single stem of 50–200 cm in height with fern-like leaves, bright yellow blossoms, and a camphor-like scent. The reproduction occurs through cross-pollination by insect or wind distribution. The plant represents a typical neophyte in lowlands and hill countries in Asia and Europe continental to subcontinental climate.
8.1.2
Phytochemistry
Artemisinin is a sesquiterpene lactone with an internal peroxide bridge (Fig. 8.1) essential for its antiparasitic effect (Klayman 1985). Its systematical nomenclature is [3R-(3a, 5a b, 6 b, 9 a, 12 b, 12aR*)]-octahydro-3,6,9-trimethyl-3,12-epoxy12H-pyrano[4,3-j]-1,2 benzodioxepin-10(3H)-one. S. Sertel • P.K. Plinkert Department of Otorhinolaryngology, Head and Neck Surgery, University Heidelberg, Im Neuenheimer Feld 400, 69120 Heidelberg, Germany T. Efferth (*) Department of Pharmaceutical Biology, Institute of Pharmacy and Biochemistry, Johannes Gutenberg University, Staudinger Weg 5, 55128 Mainz, Germany e-mail: [email protected] H. Wagner and G. Ulrich-Merzenich (eds.), Evidence and Rational Based Research on Chinese Drugs, DOI 10.1007/978-3-7091-0442-2_8, # Springer-Verlag Wien 2013
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H O O O H O
H3C
H
CH3
H3C H CH3
O H
H CH3 OH
Artemisinin
Dihydroartemisinin
CH3
H H3C
H O
O O O H O
O
O O
H3C
CH3
H
CH3 OCO(CH2)2CO2Na
Sodium artesunate
CH3
O O O H
H H3C
H O
CH3 OCH3
Artemether
CH3
O O O H
H O
CH3 O-CH2-CH3
Arteether
Fig. 8.1 Chemical structures of artemisinin and its semi-synthetic derivatives, artesunate, artemether, arteether, and dihydroartemisinic acid
Artemisinin is the lead compound of a novel class of antimalarial drugs of importance in the treatment of malaria in areas with multidrug-resistant Plasmodium falciparum. Relevant semi-synthetic derivatives of artemisinin with actual therapeutic application in malaria treatment are artesunate (ART), artemether (ARM), and arteether (ARE) (Fig. 8.1).
8.1.3
History
Qı¯ngha¯o has been used as a medicinal plant for at least 2,000 years in China. The earliest written record in silk so far discovered is the “Recipes for 52 kinds of diseases,” which was found in the Mawangdui tomb of the West Han Dynasty (168 BC) in Changsha, Hunan Province (van Agtmael et al. 1999). The first record of qı¯ngha¯o for the treatment of fever and chills was “The Handbook of Prescriptions for Emergency Treatments” by Ge Hong (281–340 BC). The next historical source stems from the year 1,086 written by Shen Gua
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