Mass Spectrometric Analysis for Discrimination of Diastereoisomers



Manshoor, Nurhuda;Weber, Jean-Fré

  • 투고 : 2015.08.12
  • 심사 : 2015.09.09
  • 발행 : 2015.12.31


A liquid chromatography mass spectrometry (LC-MS) system was used to identify and distinguish oligostilbene diastereoisomers. A polyphenolic extract from Neobalanocarpus heimii known to be rich in oligostilbenes of various degrees of condensation was used as test material. Fourteen oligostilbenes were isolated from this extract on a fully automated semi-preparative HPLC system. Out of these, two pairs of dimers, one pair of trimers, two pairs of tetramers and a group of four tetramers with similar skeleton were identified as diastereoisomers. Their structures and configurations were established by spectroscopic methods. All isolated compounds were subjected to an LC-MS/MS to study their fragmentation patterns. The experiments were performed on a liquid chromatography-mass spectrometry (LC-MS) with electrospray-ionization (ESI) interface in positive mode. MS/MS spectra of each pure compound were recorded by direct infusion in identical conditions and their product ion spectra were analysed. Some subtle yet significant differences were observed between the spectra of oligostilbenes from the various diastereoisomeric series.


HPLC;LCMS;Dipterocarpaceae;Neobalanocarpus heimii;oligostilbene


  1. Morikawa, T.; Xu, F.; Matsuda, H.; Yoshikawa, M. Heterocycles 2002, 57, 1983.
  2. Shen, T.; Wang, X. N.; Lou, H. X. Nat. Prod. Rep. 2009, 26, 916.
  3. Lin, M; Yao, C. S. Nat. Prod. Rep. 2006, 33, 601.
  4. Ma, D. Y.; Luo, H. P.; Hu, C. Q. Chinese J. Chem. 2004, 22, 207.
  5. Lee, E. O.; Lee, H. J.; Hwang, H. S.; Ahn, K. S.; Chae, C.; Kang, K. S. Carcinogenesis 2006, 27, 2059.
  6. Kitanaka, S.; Ikezawa, T.; Yasukawa, K.; Yamanouchi, S.; Takido, M.; Sung, H. K. Chem. Pharm. Bull. 1990, 38, 432.
  7. Lu, Y. H.; Lin, C. N. Helv. Chim. Acta 2003, 86, 2566.
  8. Seo, E. K.; Chai, H.; Constant, H. L.; Santisuk, T.; Reutrakul, V.; Beecher, C.W.W. J. Org. Chem. 1999, 64, 6976.
  9. Bala, A. E. A.; Kollmann, A.; Ducrot, P. H.; Majira, A.; Kerhoas, L.; Leroux, R.; Einhorn, J. J. Phytopathol. 2000, 148, 29.
  10. Ngoc, T. M.; Hung, T. M.; Thuong, P. T.; Na, M. K.; Kim, H. J.; Ha, D. T. Biol. Pharm. Bull. 2008, 31, 1809.
  11. Jonathan, M.; Michael, J. O. J. Clin. Psychiat. 2003, 5, 70.
  12. Billoa, M.; Cabalionb, P.; Waikedreb, J.; Fourneaua, C.; Bouttierc, S.; Hocquemillera, R.; Fournet, A. J. Ethnopharmacol. 2005, 96, 195.
  13. Bayach, I; Manshoor, N; Sancho-Garcia, J. C; Choudhary, M. I; Trouillas, P; Weber, J. F. F. Chem. Asian. J. 2015, 10, 198.