A New Phenylpropanoid Glucoside from the Fruits of Illicium verum

  • 발행 : 2003.08.01

초록

One new phenylpropanoid glucoside (3), along with one known phenylpropanoid (1), and one known alkyl glucoside (2) were isolated from the fruits of Illicium verum and their chemical structures were elucidated on the basis of spectroscopic studies.

키워드

참고문헌

  1. Claus, E. P. and Tyler, V. E., Pharmacognosy 5th ed. Lea and Febiger, Philadelphia, (1965)
  2. Crout, D. H. G., MacManus, D. A., and Critchley, P., Enzymatic synthesis of glycosides using the $\beta$-galactosidase of Escherichia coli: regio- and stereo-chemical studies. J. Chem. Soc., Perkin Trans. 1: Organic and Bio-Organic Chemistry, 7, 1865-1868 (1990)
  3. Enoki, A., Goldby, G. P., and Gold, M. H., $\beta$-Ether cleavage of the lignin model compound 4-ethoxy-3-methoxyphenylglycerol-$\beta$-guaiacyl ether and derivatives by Phanerochaete chrysosporium. Arch. Microbiol., 129, 141-145 (1981) https://doi.org/10.1007/BF00455350
  4. Hara, S., Okabe, H., and Mihashi, K., Gas-liquid chromatographic separation of aldose enantiomers as trimethylsilyl ethers of methyl 2-(polyhydroxyalkyl)-thiazolidine-4(R)-carboxylates. Chem. Pharm. Bull., 35, 501-506 (1987) https://doi.org/10.1248/cpb.35.501
  5. Harborne, J. B., The Flavonoids: Advances in Research. Chapman and Hall, London, pp. 464, (1993)
  6. Hottori, M., Hada, S., Shu, Y., Kakiuchi, N., and Namba, T., New acylic bis-phenylpropanoids from the aril of Myristica fragrans. Chem. Pharm. Bull., 35, 668-674 (1987) https://doi.org/10.1248/cpb.35.668
  7. Ishida, T., Bounds, S. V. J., Caldwell, J., Drake, A., and Takeshita, M., The absolute configuration of the four stereoisomers of trans-anethole diol (1-(4'-methoxyphenyl)-1,2-propanediol), a metabolite of anethole in the rat. Tetrahedron Asymm., 7, 3113-3118 (1996) https://doi.org/10.1016/0957-4166(96)00411-9
  8. Ishimaru, K., Nonaka, G., and Nishioka, I., Phenolic glucoside gallates from quercus mongolica and Q. acutissima. Phytochemistry, 26, 1147-1152 (1987) https://doi.org/10.1016/S0031-9422(00)82367-5
  9. Miki, K., Renganathan, V., Mayfield, M. B., and Gold, M. H., Aromatic ring cleavage of a $\beta$-biphenyl ether dimer catalyzed by lignin peroxidase of phanerochaete chrysosporium. FEBS Lett., 210, 199-203 (1987) https://doi.org/10.1016/0014-5793(87)81337-6
  10. Mohamed, K. M., Phenylpropanoid glucosides from Chrozophora obliqua. Phytochemistry, 58, 615-618 (2001) https://doi.org/10.1016/S0031-9422(01)00262-X
  11. Nakamura, T., Okuyama, E., and Yamazaki, M., Neurotropic components from Star Anise (Illicium verum Hook. Fil.). Chem. Pharm. Bull., 44, 1908-1914 (1996) https://doi.org/10.1248/cpb.44.1908
  12. Okuyama, E., Nakamura, T., and Yamazaki, M., Convulsants from star anise (Illicium verum HOOK. F.). Chem. Pharm. Bull., 41, 1670-1671 (1993) https://doi.org/10.1248/cpb.41.1670
  13. Sakamoto, Y., Shiraishi, A., Jeong, S. H., and Nakata, T., Stereoselective syntheses of cytoxazone, a novel cytokine modulator, and its stereoisomers. Tetrahedron Lett., 40, 4203-4206 (1999) https://doi.org/10.1016/S0040-4039(99)00712-1
  14. Sigurskjold, B. W., Haunstrup, I. B., and Bock, K., Hydrolysis of substrate analogues catalysed by $\beta$-D-glucosidase from Aspergillus niger. Part III. Alkyl and aryl $\beta$-D-glucopyranosides. Acta. Chem. Scand., 46, 451-458 (1992) https://doi.org/10.3891/acta.chem.scand.46-0451
  15. Sy, L. K. and Brown, G. D., A seco-cycloartane from Illicium verum. Phytochemistry, 48, 1169-1171 (1998a) https://doi.org/10.1016/S0031-9422(98)00150-2
  16. Sy, L. K. and Brown, G. D., Novel phenylpropanoids and lignans from Illicium verum. J. Nat. Prod., 61, 987-992 (1998b) https://doi.org/10.1021/np9800553
  17. Veibel, S. and Lillelund, H., Synthesis and properties of several O-alkyl glucosides. II. Glucosides of the 5 butanols and the tertiary pentanhexan- and heptanols. Bull. Soc. Chim., 5, 494-502 (1938)