Research ArticleOpen AccessGoogle Scholar indexed
Microtropins J-P: 6’-O-(2”<i>S</i>,3”<i>R</i>)-2”-Ethyl-2”,3”-Dihydroxybutyrates of Phenolic Alcohol <i>ß</i>-D-Glucopyranosides from the Branches of <i>Microtropis japonica</i>
Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, Hiroshima, Japan;
Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, Hiroshima, Japan;
Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, Hiroshima, Japan;
Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, Hiroshima, Japan;
Department of Natural Products Chemistry, Faculty of Pharmacy, Yasuda Women’s University, Hiroshima, Japan.
- 1 Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, Hiroshima, Japan;
- 2 Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, Hiroshima, Japan;
- 3 Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, Hiroshima, Japan;
- 4 Department of Pharmacognosy, Graduate School of Biomedical and Health Sciences, Hiroshima University, Hiroshima, Japan;
- 5 Department of Natural Products Chemistry, Faculty of Pharmacy, Yasuda Women’s University, Hiroshima, Japan.
American Journal of Plant Sciences·Volume 04 (2013)·Pages 1954–1959·Published 25 September 2013·DOI10.4236/ajps.2013.410242
Copy link · social · email
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 (2 S ,3 R )-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<i>Microtropis japonica</i>CelastraceaeMicrotropin(2S3R)-2-Ethyl-23-Dihydroxybutyrate
- 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
- 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
- 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
- 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
- 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
- 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
- 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