Germacranolide lactones

A. artemlsllfolla (8), we had isolated the germacranolide 11,13-dihydroparthenolide (16) the germination activity effects of which will be discussed in the following section together with the other sesquiterpene lactones. 

The cyclobutanone (201) also underwent smooth oxidation to afford the y-lactone (202), which was not isolated and was allowed to react further to yield the cytotoxic germacranolide eucannabinolide (203) in a number of steps 70 (... 

In 1959-61, a Czech group [8,9] reported the isolation of a new sesquiterpene lactone from Chrysanthemum (Tanacetum) parthenium as part of a study of the sesquiterpene lactones of the Compositae family. They named it parthenolide. The initial structure for parthenolide was later revised [10,11] and the accepted structure for parthenolide today is represented by structure (1). Parthenolide is a germacranolide-type sesquiterpene lactone. The crystal structure for parthenolide has also been reported [12]. Extractions of C. (T.) parthenium grown in Mexico, known locally as santamaria, did not yield parthenolide [13], but a closely related compound was isolated and named santamarine (3). This suggests that regional variations in the chemical constituents may occur. 

In summary, feverfew appears to be a source of a range of sesquiterpene lactones of three different types germacranolides, eudesmanolides and guaianolides. 

A few individual terpenoids, as well as less expensive mixtures of these compounds, find practical applications. Some examples are the tli terpenoid Vitamin A, the sesquiterpenoid santonin (as an anthelmintic), and the pyrcthnns, pyrctholonc esters of the monoterpenoid chrysanthcmic acid (used as an insecticide). A number of sesquiterpenoid lactones of the germacranolide. guaianolide and elemanolide types have shown promise as rumor inhibitors. 

The plant Achillea clusiana from the mountains of Bulgaria contains the new 2-epi-chIoroklotzchin (256), which is the first report of a halogenated sesquiterpene lactone from Achillea genus (512). Chloroform was used to process the plant. The Egyptian medicinal plant Ambrosia maritima, which is still used to treat renal colic and other aliments, has afforded 1 lp-hydroxy-13-chloro-l 1,13-dihydrohymenin (257) (513). Eupaglehnins E (258) and F (259) are novel germacranolides isolated... 

B. gaudichaudiana, which is commonly used for diabetes. Elephantopus scaber contains hydroxylated germacranolides, such as molephantin and molephantinin, which cause diuresis, antipiresis, eliminate bladder stones, and have cytotoxic and antitumor properties. From the Tithonia genus, T, diversifolia is widely used in Mexico and often has been identified erroneously as Arnica montana. Because of this confusion it is used as European arnica to treat hematomas and muscular cramps. The genus is rich in sesquiterpene lactones.11... 

Acetoxy-eremantholide B (germacranolide sesquiterpene lactone) Costunolide (germacranolide sesquiterpene lactone)... 

Epoxy-5,10-dihydoxy-6a-angeloyloxy-9 (3-isobutyloxy germacran-8a, 12-olide (germacranolide sesquiterpene lactone) Carpesium divaricatum (Asteraceae) l iNOS expression [per inhibiting NFkB activation]... 

Isovaleroyl 15-(2-methylbutyryl)-2a-acetoxymiguanin (germacranolide sesquiterpene lactone) Asteraceae NFkB activation blocked (1) ( hence cytokine, TNF-a iNOS expression)... 

Alatolide (germacranolide sesquiterpene lactone) Jurinea alata (Asteraceae) Insect antifeedant... 

The structural elucidation and total synthesis of sesquiterpenoid lactones such as the germacranolides [cf. (310)] and eudesmanolides [cf. (311)] continues to be a very... 

The isolation and identification of germacrane lactones from a host of plant sources is an area of continuing interest particularly in the laboratories of Professors Herz and Bohlmann. The search for biologically active compounds and the chemotaxonomic classification of plant species are the two major driving forces for this research. The sub-division of these lactones into germacranolides (479)—... 

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