14E-23 |
Identification of the degradation products of Glucosamine by gas chromatography/mass spectrometry, liquid chromatography/mass spectrometry and nuclear magnetic resonance |
M. JUN1, Y. Shao2, and C. T. Ho1. (1) Dept. of Food Science, Rutgers, The State Univ. of New Jersey, 65 Dudley Rd., New Brunswick, NJ 08901-8520, (2) New Product Development, GlaxoSmithKline Consumer Healthcare, Parsippany, NJ 07054 Glucosamine, 2-amino-2-deoxyglucose, is widely distributed in various plant tissue and animal muscle. Glucosamine exhibits not only weak anti-inflammatory activity but also showed analgesic effect when combined with ibuprofen. Currently, glucosamine is marketed as nutritional supplement to enhance the repair and synthesis of connective tissue and cartilage. Stability evaluation provides information about how the quality of bulk drug or drug product changes under the influence of various factors, for example, temperature, humidity, pH, and light. This information helps for determination of recommended storage conditions and for establishment of shelf lives and retest periods. To support the studies on the stability of glucosamine pharmaceutical preparation or excipient, understanding of glucosamine stability is required, which initiated the studies on glucosamine degradation. The objective of this study was to isolate and determine the structures of non-volatile degradation products of glucosamine. Furthermore, the mechanisms of isolated degradation products were proposed. The stability of glucosamine mixture was investigated at 100°C in aqueous solution. The mixture was acetylated and purified with column chromatography with silica gel. The degradants were identified utilizing a variety of analytical techniques, such as gas chromatography/mass spectrometry, liquid chromatography/mass spectrometry, 1H,13C- nuclear magnetic resonance, as well as 1H-1H COSY. Six degradation products were identified from glucosamine degradation. Among the degradants, two were identified from glucosamine excipient. Major degradation products were pyrazine derivatives containing four carbons side chains attached to C-2 and C-5 of the ring, respectively. This forced-degradation study with glucosamine and glucosamine excipient has shown that glucosamine degraded under temperature. From the proposed mechanism, pyrazine seems to be produced by self-condensation of glucosamines with loss of 2 water molecules during thermal reaction. Further research on glucosamine degradation might be needed for better understanding of glucosamine stability.
Session 14E, Nutraceuticals & Functional Foods: General I
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