Pseudoanisatin

Illicium lanacedatum A. S. Smith Hong Hui Xiang Gen (Japanese star anise) (fruit) Anisatin, neoanisatin, shikimic acid, pseudoanisatin 33 This herb is toxic. ... 

The details of the isolation of prezizaene (393), and its implication in the biogenesis of the tricyclovetivane group, have been published.The structure of a new sesquiterpenoid, pseudoanisatin (394), related to anisatin has been... 

Illicium anisatum contains sesquiterpenoids, such as anisatin, anisotin, neoanisatin, and pseudoanisatin. Illicium religiosum (Japanese star anise) contains shikimic acid, anisatin and neoanisatin. Illicium verum (Chinese star anise) contains the monoterpenoid transanethole. Chinese star anise has been used to treat infant colic, but can be confused with Japanese star anise, which contains the neurotoxin anisatin. 

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. 

Fig. (30). Pseudoanisatin (PSA, insect-selective A) and veranisatin A (VER, non-selective, B) shown inside the fly (top) and rat (bottom) receptor surface models (from [163]).

Pseudoanisatin was first isolated as a nontoxic compound from I. anisatum by Lane et al [4]. The wrong structure of pseudoanisatin was first proposed on the basis of the spectral data [17], but later it was revised as 12 with a 7-membered 11,14-lactone by an X-ray crystal... 

Fig. (4). Ketone and acetal equilibrium of pseudoanisatin-type sesquiterpenes 12 and 25 - 26, and acetal sesquiterpenes 27 - 29...

The structures of the sesquiterpenes, which belong to pseudoanisatin-subtype having a hydroxyl group at the C-7 position, seem to be confused. The structure of 7-deoxy-7 3-... 

Pseudoanisatins derivatives, which have been checked to this point, are non-toxic substances unlike anisatin, but it is worthy to note that isodunnianin (32) not only promote neurite outgrowth in primary cultured fetal rat cortical neurons at 10 pM but also increase the choline acetyltransferase activity [28]. 

Although anisatin (1) and its related seco-prezizaane-subtypes such as pseudoanisatin (12) have been postulated to be biosynthesized... 

Compounds 4 and 5, together with three known sesquiterpenes, i.e., pseudoanisatin, pseudomajucin and illicinolide A, were isolated from the acetone extract (50 g) of the fresh fruits by column chromatographies over Chromatorex ODS, Bondapak ODS and silica gel. Both 4 and 5 are white amorphous powders, showed [M+Na]" ion peaks at m/z 495 in the... 

Prostanoic acid, A25 Protoanemonin, A12 Protoaphins, YIO Protoemetine, K2 Protostanes, T50, T15 Protostemonine, K29 Protoverine, K35 Pseudoanisatin, T30 Pseudoclovenes, T6 Pseudoconhydrine, K19 Pseudocopsinine, K4 Pseudoecgonine, K28 Pseudoguaianolides, T24, T9 Pseudoheliotridane, K22 Pseudohygroline, K19 Pseudoivalin, T9 ... 

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