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Paper | Special issue | Vol 97, No. 1, 2018, pp.314-332
Published online, 16th May, 2018
DOI: 10.3987/COM-18-S(T)21
Synthesis of Salacinol-d4 as an Internal Standard for Mass-Spectrometric Quantitation of Salacinol, a Potent α-Glucosidase Inhibitor Found in a Traditional Ayurvedic Medicine “Salacia

Genzoh Tanabe,* Sanami Teramae, Yousuke Kunikata, Shinsuke Marumoto, Shuhei Okugawa, Fumihiro Ishikawa, Weija Xie, Toshio Morikawa, and Osamu Muraoka

*Faculty of Pharmacy, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502, Japan

Abstract

Accurate quantitative analysis of trace principles in extracts of biologically active natural medicines relies on the use of reliable internal standards (ISs), which, in the case of liquid chromatography–mass spectrometry (LC-MS) analysis, commonly correspond to isotope-labeled stable analogues of the analytes. Herein, we describe the synthesis of salacinol-1,1,5,5-C-d4 (7), an isotope-labeled stable analogue of salacinol (1), which, in turn, is a potent α-glycosidase inhibitor isolated from Salacia (a traditional Ayurvedic medicine), and show that the isotopic purity of the labeled standard is satisfactory for LC-MS analysis.