DETERMINATION OF THE ABSOLUTE CONFIGURATION OF NEW PIPERIDIN-4-ONE DERIVATIVE FROM Pellacalyx saccardianus BY NOESY SPECTROSCOPY

Authors

  • Salam Ahmed Abed Department of Chemistry, Faculty of Science Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia
  • Hasnah Mohd Sirat Department of Chemistry, Faculty of Science Universiti Teknologi Malaysia, 81310 UTM Johor Bahru, Johor, Malaysia

DOI:

https://doi.org/10.11113/jt.v78.7806

Keywords:

Pellacalyx saccardianus, Pellacalyxin, Absolute configuration, X-ray crystallography, NOESY spectroscopy

Abstract

A new alkaloid, pellacalyxin was isolated from the leaves of Pellacalyx saccardianus of Rhizophoraceae family. Pellacalyxin was analyzed using nuclear Overhauser spectroscopy (NOESY) nuclear magnetic resonance (NMR) technique to determine the absolute configuration. The analysis of absolute configuration of pellacalyxin was supported by X-ray crystallography. 1H-1H NOESY NMR spectroscopy exhibited that pellacalyxin possesses two chiral centers (3S) and (6R).

References

Kong, L.-Y., Wang, P. 2013. Determination Of The Absolute Configuration Of Natural Products. Chinese Journal of Natural Medicine. 11(3): 193-198.

Ding, S., Jia, L., Durandin, A., Crean, C., Kolbanovskiy, A., Shafirovich, V., Broyde, S., Geacintov, N. E. 2009. Absolute Configurations of Spiroiminodihydantoin and Allantoin Stereoisomers: Comparison of Computed and Measured Electronic Circular Dichroism Spectra. Chemical Research in Toxicology. 22(6):1189-1193.

Ariens, E. J. 1986. Stereochemistry: A Source Of Problems In Medicinal Chemistry. Medicinal Research Reviews. 6(4): 451-466.

Li, X.-C., Ferreira, D., Ding, Y. 2010. Determination of Absolute Configuration of Natural Products: Theoretical Calculation of Electronic Circular Dichroism as a Tool. Current Organic Chemistry. 14(16): 1678-1697.

Abed, S. A. 2015. Structural Elucidation and Bioactivity Evaluation of Phytochemicals from Pellacalyx saccardianus Scortech and Gynotrochesaxillaris Blume. Doctor of Philosophy Thesis. Universiti Teknologi Malaysia; Malaysia.

Abed, S. A. and Sirat, H. M. 2015. COX-2 Inhibitors from the Leaves of Pellacalyx saccardianus Scortech (Rhizophoraceae) Phytochemistry Letters, in press.

Rahmani, B. M., Kiew, R., Lajis, H. N., Othman, R., Toia, R. F. 1985. A. Contribution to the Phytochemical Survey of Peninsular Malaysia. Pertanika. 8(3): 347-357.

Wade, L. G.. 1999. Organic Chemistry. 4thed. New Jersey: Prentice-Hall.

Wilk, A., Grajkowski, A., Bull, T. E., Dixon, A. M., Daro´n I. Freedberg, D. I., Beaucage, S. L. 2002. Direct Assignment of the Absolute Configuration of a Distinct Class of Deoxyribonucleoside Cyclic N-Acylphosphoramidites at Phosphorus by M-GOESY Nuclear Magnetic Resonance Spectroscopy.Journal of the American Chemical Society. 124(7): 1180.

Downloads

Published

2016-03-09

How to Cite

DETERMINATION OF THE ABSOLUTE CONFIGURATION OF NEW PIPERIDIN-4-ONE DERIVATIVE FROM Pellacalyx saccardianus BY NOESY SPECTROSCOPY. (2016). Jurnal Teknologi, 78(3-2). https://doi.org/10.11113/jt.v78.7806