Lactones artemisia

Teoh KH, Polichuk DR, Reed DW, Nowak G Covello PS. (2006) Artemisia annua L. (Asteraceae) trichome-specific cDNAs reveal CYP71AV1, a cytochrome P450 with a key role in the biosynthesis of the antimalarial sesquiterpene lactone artemisinin. FEBS Lett 580 1411-1416. 

Foglio MA, Dias PC, Antonio MA, Possenti A, Rodrigues RA, da Silva EF, Rehder VL, de Carvalho JE. (2002) Antiulcerogenic activity of some sesquiterpene lactones isolated from Artemisia annua. Planta Med 68 515-518. 

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. 

Ruiz-Cancino, A., Cano, A.E., and Delgado, G., Sesquiterpene lactones and flavonoids from Artemisia ludoviciana ssp. mexicana. Phytochemistry, 33, 1113, 1993. 

There are only few references on odd-numbered lactones in the literature. The first reports on the natural occurrence of y-nonalactone and y-undecalactone are known from the early flavour literature [28-30], long before sophisticated analytical techniques, such as enantio-cGC-MS, became available. These data have to be reevaluated, should the situation arise. Worner et al. [31] provided the first report on y-nonalactone among the volatile constituents of Artemisia vulgaris L. herb, revealing an amount between 1 andlO pg/kg and an enantiomeric distribution of (i )-y-nonalactone to (S)-y-nonalactone of 34 66 using en-antio-MDGC, coupled online with MS. 

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. 

Although the first survey listed 45 natural chlorinated sesquiterpene lactones, several such compounds were omitted in that coverage (1) and are described here. The novel sesquiterpene lactone chlorochrymorin (239) was isolated from Chrysanthemum morfolium (499), and the chlorohydrin graminichlorin (240) is found in Liatris graminifolia (500). The antibacterial AA-57 (241), which is related to pentalenolactone, is produced by a Streptomyces sp. (501). The plant Eupatorium chinense var. simplicifolium has yielded eupachifolin D (242) (502) (side-chain double bond stereochemistry revised (518)), and the new guaianolide andalucin (243) was characterized from Artemisia lanata (503). The previously known chlorohyssopifolins (1) have been studied for cytostatic activity, and the presence of one and even two chlorine atoms amplifies this activity (504). 

The Chinese Eupatorium chinense has afforded ten new sesquiterpenoids, three of which are chlorinated, eupachinilides C (263), E (264), and F (265) (518). The Chinese medicinal plant Eupatorium lindleyanum contains the chlorinated guaianes eupalinilides A (266), D (267), E (268), and H (269), amongst other non-chlori-nated eupalinilides and nine known sesquiterpenoids (579). The Oregon coastal perennial plant Artemisia suksdorfii contains four novel chlorinated sesquiterpene lactones 270-273 520). 

Aguilar JM, Collado IG, Macias FA, Massanet GM, Rodriguez-Luis F, Fronczek FR, Waikins SF (1988) Sesquiterpene Lactones from Artemisia lanata. Phytochemistry 27 ... 

Ahmed AA, El-Moghazy SA, El-Shanawany MA, Abdel-Ghani HF, Karchesy J, Sturtz G, Dailey K, Pare PW (2004) Polyol Monoterpenes and Sesquiterpene Lactones from the Pacific Northwest Plant Artemisia suksdorfii. J Nat Prod 67 1705... 

Stiles, L. H., Leather, G. R., and Chen, P. K. 1994. Effects of two sesquiterpene lactones isolated from Artemisia annua on physiology of Lemna minor. J. Chem. Ecol. 20, 969-978... 

Artemisinin (23), isolated from a Chinese medicinal plant, annual wormwood Artemisia annua L.), is a unique sesquiterpene lactone bearing an endoperoxide moiety. This compound displays a strong antimalarial activity and inhibits seed germination and plant growth.11... 

Absinthin, the active principle of wormwood, Artemisia absinthium L. (Compositae), is a dimeric guaianolide containing two lactone rings and two hydroxy groups per molecule.162 Thelephoric acid (76b), isolated from fungi of several Thelephora species, has been synthesized by oxidative condensation of two molecules of sodium 3,4-dimethoxy-phenoxide with one of chloranil in the presence of hydrobromic acid.162a... 

Jeremic, D. Jokic, A. Behbud, A. Stefanovic, M. A new t)fpe of sesqiterpene lactone isolated from artemisia annua L. arteannuin B Tetrahedron Lett., 1973, 32 3039-3042. 

Misra, L. N. Arteannuin C, a sesquiterpene lactone from Artemisia annua. Phytochemistry, 1986, 25(12) 2892-2893. 

Acton, N. Klayman, D. L. Artemisitene, a new sesquiterpene lactone endoperoxide from Artemisia annua. Planta Med., 1985, 5 441-442. 

Brown, G. D. Annulide, a sesquiterpene lactone from Artemisia-Annua. Phytochemistry, 1993, 32(2) 391-393. 

A crystalline lactone obtained from the dried unexpanded flowerheads of Artemisia cina and other species of Artemisia (Compositae). 

Artemisia cina (wormseed) contains the toxic lactone, santonin, which was formerly used as an antihelminthic drug, but has now been superseded by other less toxic compounds. 

Artemisia vulgaris (common wormwood) contains the toxic lactone, santonin, which was formerly used as an antihelminthic drug, but has now been superseded by other less toxic compounds. Depending on the origin of the plant, 1,8-cineole, camphor, hnalool, and thujone may all be major components. Allergic skin reactions (12) and abortive activity have been described. 

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