Illicium religiosum Shikimic acid

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. 

Shikimic acid, for which the pathway is named, was first discovered in the plant Illicium religiosum in 1885 and was named after the Japanese name for the plant, shikimi-no-ki. The compound makes up 20% of the dry weight of the fruits of this plant. For many years, chemists considered this com-... 

A related unsaturated compound, shikimic acid (Fig. 2), was found in the star anise (Illicium verum and I, religiosum) (72), Its presence has... 

A compound of unsuspected importance was isolated in 1885 from the fruit of Illicium religiosum. To this compound was given the name shikimic acid, a name derived from shikimi-no-ki which is the Japanese name for the plant. Shikimic acid (5.7), it transpired from the very elegant studies of much later investigators, is a key intermediate in the biosynthesis of the aromatic amino acids, L-phenylalanine, L-tyrosine and L-tryptophan, in plants and micro-organisms (animals cannot carry out de novo synthesis using this pathway). These three aromatic amino acids are individually important precursors for numerous secondary metabolites, and so to some extent are earlier biosynthetic intermediates related to shikimic acid, as the ensuing discussion in this chapter and in Chapters 6 and 7 will show. 

Shikimic add was first described as a natural product from the plant Illicium religiosum Sieb. by Eykmann in 1885 and it was from the Japanese name of this plant, shikimi-no-ki, that the name shikimic acid was derived. Eykmann s own investigations coupled with the detailed structural emd stereochemical studies of Fischer and Dangschat " , Freudenberg and Karrer led to the formulation of both (—)-shikimic acid and the closely related natural product (—)-quinic acid as (4) and (5) respectively. Fischer and Dangschat also remarked on the close structural similarity of known aromatic... 

Shikimic acid (XV) was first found in star anise Illicium religiosum) and later in many other plants. In recent times it has been experimentally established as a biogenetic key link in the elaboration of aromatic amino-acids and lignin in vivo, and it appears to be involved in other biosynthetic reactions. The total synthesis of shikimic acid has only recently been accomplished. ... 

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