Illicium species

CHEMISTRY AND NEUROTROPHIC ACTIVITY OF S C0-PREZIZAANE- AND ANISLACTONE-TYPE SESQUITERPENES FROM ILLICIUM SPECIES... 

The fruits of the Illicium species are distinctive star-shaped follicles which emit a characteristic refreshing flavor. The fruits of I. vernum Hook, in particular, are the source of the only economically important product derived from the genus Chinese star anise, which is widely used as a spice for flavoring food and beverages. Hence, essential oils have been the primary subject of chemical research on Illicium species and the presence of volatile phenols have been reported as constituents of various parts of all Illicium studied so far. On the other hand, the fruits of /. anisatum, Japanese star anise, have been known to be very toxic for several centuries. Many researchers had been involved in the attempt to isolate the toxic substance since the middle of the 19th century. In 1952, Lane et al. succeeded in the isolation of the 0 pure toxic principle named anisatin (1) [4]... 

Small, E. 1996. Confusion of common names for toxic and edible "star anise" (Illicium) species. Econ. Bot. 50(3) 337-339. 

The closely related Japanese star anise, I. anisatum, is highly toxic. It contains a poisonous sesquiterpene lactone, called ani-satin, and also shikimin and sikimitoxin, which causes severe inflammation of the kidneys, urinary tract and digestive organs, as well as affecting the nervous system (Lederer et al., 2006). Other compounds present in this toxic species of Illicium are saffole and eugenol, which are not present in I. verum and are used to identify its adulteration. 

The family of Illiciaceae contains a single genus, Illicium, the star anise species. 

Our own work on structure-activity relationships of convulsant sesquiterpene lactones was initiated after isolation of a variety of seco-prczizaanc type compounds from Illicium floridanum and I. parviflorum, both endemic to the southern United States [157, 179-181]. A study on the in-vivo toxicity of several of these compounds [182] showed that anisatin, major constituent in leaves and fruits of I. floridanum (as in those of other previously studied toxic Illicium (=star anise) species, review see [3]), was apparently the only derivative in the tested series which was toxic to mammals, although further compounds, such as pseudoanisatin (PSA, structure 4 in Fig. (27)) were accumulated in the plant in similarly high amounts [179, 180]. In the light of reports that indicated an identical mechanism of action and -possibly- the existence of a common binding site for anisatin and picrotoxinin [156-161] the question arose which structural features in these compounds were similar enough to warrant an identical mode of molecular recognition at the channel protein. 

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