Artemisia maritima

Artemisia maritima (Asteraceae), Salma lavandulaefolia (Lamiaceae), Eucalyptus globulus, E. spp., Melaleuca leucadendron (Myrtaceae) [oil], Alpinia, Curcuma (Zingiberaceae)... 

Cineole Artemisia maritima (Asteraceae), Ocimum Insect repellent (OD-R)... 

The various plant species uptake non-equivalent amounts of boron from soils. An unlimited uptake, proportional to soil content, is common for Artemisia maritima,... 

Artemisin. 3a,5,5a,9b-Tetrahydro-4-hydroxy-3,5a, 9.trimethylnaphlho[l, 2-bffu ran-2,8(3H,4H l-dione 6a,8ct-dihydroxy-3-oxoeudesma-l,4-dien-12-oie acid 12,6-lactone 8-hydroxysantonin. C jH S04 mol wt 262.29, C 68.68%, H 6.92%, O 24.40%. From the closed, unexpanded flower heads of several Artemisia spp, especially Artemisia maritima L., and A. clna Berg., Compositae ( wormseed ). Found in the mother liquors from the extraction of santonin. Isoln E. Merck, Merck s Jahresber. 1894, 3 Chem. Zentr. 1895, I, 436. Structure Sumi. J. Am. Chem. Soc. 80, 4869 (1958) Cocker, McMurry, Tetrahedron 8, l8l (1960). Stereochemistry Bolt et of., J. Chem. Soc 1963, 5235. Synthesis of (+) -artemisin Nakazaki, Naemura, Tetrahedron Letters 1966, 2615. 

Oil of Levant Wormseed. Volatile oil from the flowers of Artemisia maritima var stechmanniana Bess (A. pauciflora Weber), Compositae. Constit Largely eucalyptol (cineol)... 

Santonica. Levant wormseed. Dried, unexpanded flower heads of Artemisia maritima L., sens, lat., Compasitae. Habit, Iran, Turkestan. Constit. 2-4% santonin, 2-3% volatile oil artemisin, resin. 

Santonin (7.30) occurs in the oil known as Levant Wormseed Oil. This oil is not extracted from the seeds, but from the unopened flower heads of several herbs of the family Artemisia, principally from Artemisia maritima. Its use in folk medicine for the treatment of intestinal worms stems from the anthelmintic properties of santonin. Santonin undergoes a number of very interesting reactions, three of which are summarised in Figure 7.9. 

Artemisin (2) is an 8-hydroxy-functionalized eudesmanolide that is isolated from Artemisia maritima and is closely related to santonin, and is a compound that has been successfully used by our group in several syntheses of sesquiterpenolides functionalized at C(8) or C(9). For example, artemisin (2) has been transformed into the cytotoxic compounds artapshin (147) and dihydro-8a-hydroxybalchanin (148) [28] in a synthetic sequence (Scheme 19) in which the transformation of the A ring was achieved in a similar way to that described previously in the synthesis of dihydrosantamarin (see Scheme 8). 

Santonin (130), a sesquiterpene lactone from Artemisia maritima (Asteraceae) has been used as an ascaricide, and is especially active against roundworms (Ascaris spp.). 

Isol. from Artemisia maritima. Prisms (EtOH). Mp 228° K +70° (CHCI3). 

Derivation By extraction from Artemisia cina, Artemisia maritima, or other species of Artemisia. 

Artemisia maritima is a drug that was widely used in the past as anthelmintic and was later removed based on its severe side effects. Its biosynthesis is based on the methylene reduction of costunolide (23) and its proton activation and cyclization of germacrane core to provide eudesmyl cation (14). Sequential oxidative steps at C-1 and C-3 positions, followed by elimination of water, complete the route to a-santonin [19]. 

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