Shikimic Acid as a Marker Compound from Ludwigia alternifolia L.

Ludwigia alternifolia L belongs to the Onagraceae family and is distributed throughout the Northeast, Midwest and Southern US. Shikimic acid (Fig. 1) was first isolated in 1885 by Eijkman from the fruit of the Japanese plant Illicium religiosum Sieb [1]. The elucidation of its structure nearly 50 years later [2,3] and the discovery that shikimic acid was found to play an important role in the biosynthesis of the three aromatic amino acids phenylalanine, tyrosine, and tryptophan [4] resulted in an intensified research effort towards its synthesis [5–9], isolation from other organisms [10], identification of its metabolites [11,12] and its transformation into potential chemotherapeutics. This latter area of research has lead to the syntheses of various bioactive compounds from shikimic acid. The research outlined in this presentation is the first report for the isolation of shikimic acid from this plant.

Acknowledgements: The work was supported by the United States Department of Agriculture, Agricultural Research Service Specific Cooperative Agreement Number 58-6408-06-067. Thanks to Mr. Frank Wiggers for NMR, Dr. Barathi Avula for HRESIMS, Dr. Vaishali C Joshi for plant identification at the National Center for Natural Products Research. References: [1] Eijkman JF, (1885) Recl Trav Chim 4: 32. [2] Fischer HOL, Dangschat G (1934) Helv Chim Acta 17: 1200. [3] Fischer HOL, Dangschat G. (1935) Helv. Chim. Acta 18: 1204. [4] Davis BDJ (1951) Biol Chem, 191: 315. [5] Campbell MM, et al. (1993) Synthesis 1. [6] Jiang S, Singh G, (1998), Tetrahedron 54: 4697. [7] Shinada T, et al. (1998) Tetrahedron Lett 39: 6027 [8] Mehta G, Mohal N (1998) Tetrahedron Lett 39: 3285 [9] Yoshida N, Ogasawara K (2000) Org. Lett 2: 1461. [10] Hattori S, Yoshida S, Hasegawa M. (1954) Physiol. Plantarum 7: 283 [11] Bohm, BA (1965) Chem. Rev 65: 435 [12] Haslam E. Shikimic Acid Metabolism and Metabolites; John Wiley and Sons: New York, 1993.