Microtropins J-P: 6’-O-(2”S,3”R)-2”-Ethyl-2”,3”-Dihydroxybutyrates of Phenolic Alcohol ß-D-Glucopyranosides from the Branches of Microtropis japonica

Yuka Uemura, Sachiko Sugimoto, Katsuyoshi Matsunami, Hideaki Otsuka, Yoshio Takeda

Department of Natural Products Chemistry, Faculty of Pharmacy, Yasuda Women’s University, Hiroshima, Japan..
Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, Hiroshima, Japan;.

DOI: 10.4236/ajps.2013.410242                

Abstract

From the branches of Microtropis japonica (Celastraceae), seven phenolic alcohol glucosides, named microtropins J-P (1-7), were isolated. The 6-position of glucose was esterified with 2-ethyl-2,3-dihydroxybutyric acid. Microtropin K (2) was hydrolyzed under a mild basic condition to give methyl (2S,3R)-2-ethyl-2,3-dihydroxybutyrate, whose absolute structure was determined by the comparison of NMR data and the optical rotation value with that reported.

Keywords

Microtropis japonica; Celastraceae; Microtropin; (2S, 3R)-2-Ethyl-2, 3-Dihydroxybutyrate

Conflicts of Interest

The authors declare no conflicts of interest.

References

[1]	S. M. Kapchan, Y. Komoda, W. A. Court, G. J. Thomas, R. M. Smith, A. Karim, C. J. Gilmore, R. C. Haltiwagner and B. F. Bryan, “Maytansine, a Novel Antileukemic Ansa Macrolide from Maytenus ovate,” Journal of American Chemical Society, Vol. 94, No. 4, 1972, pp. 1354-1956. http://dx.doi.org/10.1021/ja00759a054
[2]	J. M. Cassady, K. K. Chan, H. G. Floss and E. Leistner, “Recent Developments in the Maytansinoid Antitumor Agents,” Chemical and Pharmaceutical Bulletin, Vol. 52, No. 1, 2004, pp. 1-26. http://dx.doi.org/10.1248/cpb.52.1
[3]	Y. Koyama, S. Sugimoto, K. Matsunami and H. Otsuka, “Microtropiosides A-F: ent-Labdane Diterpenoid Glucosides from the Leaves of Microtropis japonica (Celastraceae),” Phytochemistry, Vol. 71, No. 5-6, 2010, pp. 67-681. http://dx.doi.org/10.1016/j.phytochem.2010.01.004
[4]	Y. Uemura, S. Sugimoto, K. Matsunami, H. Otsuka, Y. Takeda, M. Kawahata and K. Yamaguchi, “Microtropins A-I: 6’-O-(2”S,3”R)-2”-ethyl-2”,3”-dihydroxy-butyrates of Aliphatic ß-D-Glucopyranosides from the Branches of Microtropis japonica,” Phytochemistry, Vol. 87, No. 1, 2013, pp. 140-147. http://dx.doi.org/10.1016/j.phytochem.2012.11.007
[5]	A. Sakushima, M. Coskun and T. Maoka, “Hydroxy-Benzoic Acids from Boreava orientalis,” Phytochemistry, Vol. 40, No. 1, 1995, pp. 257-261. http://dx.doi.org/10.1016/0031-9422(95)00059-G
[6]	Y. Asakawa, M. Toyota and L. Harrison, “Isotachin A and Isotachin B, Two Sulphur-Containing Acrylates from the Liverwort Isotachis japonica,” Phytochemistry, Vol. 24, No. 7, 1985, pp. 1505-1508. http://dx.doi.org/10.1016/S0031-9422(00)81055-9
[7]	B. A. A. A. Balboul, A. A. Ahmed, H. Otsuka and A. de Adams, “4-Hydroxyphenylpropan-7,8-diols and Derivatives from Narvalina domingensis,” Phytochemisty, Vol. 42, No. 4, 1996, pp. 1191-1193. http://dx.doi.org/10.1016/0031-9422(96)00116-1