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A Cartilage Derived Novel Compound DDP
(2,6-dimethyldifuro-8-pyrone): Isolation, Purification, and Identification
HARPAL K. GAHUNIA, ALAN LOUGH, REINHOLD VIETH, and KENNETH P.H. PRITZKER
ABSTRACT. Methods. Fully encapsulated, bovine metacarpophalangeal joints (n = 350, age < 2 years) were used as the source for AC. DDP was isolated and purified by reverse phase high pressure liquid chromatography, and its elution was monitored using a fluorescence detector at excitation l = 306 nm, and emission l = 395 nm. The liquid phase of DDP was characterized by mass spectrometry and nuclear magnetic resonance spectroscopy. DDP solution (5.7 µg/µl) was crystallized in 100% deuterated methanol and the DDP crystal was characterized by single crystal x-ray diffraction. Results. From bulk preparations, 12 µg (58 nmol) per gram dried AC of the novel compound was isolated and purified. Analytical techniques to identify this AC-specific compound, 2,6-dimethyldifuro-8-pyrone, corroborate and confirm its molecular structure and atomic connectivity in both liquid and solid phase. DDP is a symmetrical aromatic compound with molecular weight 204, molecular formula C11H8O4, and a molar extinction coefficient 4700 M-1 at maximal UV absorption (l = 306 nm). Conclusion. 2,6-dimethyldifuro-8-pyrone (DDP) is a novel cartilage-specific compound that could have potential application as a unique biochemical marker in joint diseases involving articular cartilage degradation. (J Rheumatol 2002;29:147-53) Key Indexing Terms:
ARTICULAR CARTILAGE
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