To clarify the degradation pathway of acrinol by light, isolation and identification of acrinol degradation products (ANDP) were attempted. A novel acrinol degradation product, ANDP-8, one of the ANDPs, was isolated by extraction with methanol from cloths dampened with acrinol solution, and purified by column chromatography on Diaion HP-10 and Sephadex LH-20. The structural elucidation of ANDP-8 was examined by infrared, 1 H-NMR, 13 C-NMR and electron impact ionization (EI)-mass spectra studies. From the spectroscopic data, the structure of ANDP-8 was determined to be 2-ethoxyl-6, 9-acridinediamine-5, 8-dione, that was found to be a novel degradation product of acrinol by light. Antimicrobial activities of ANDP-8 against Gram-positive bacteria were 10 to 100-fold higher than those of acrinol. ANDP-8 was also active against yeast and fungi. Nevertheless, acrinol did not show growth inhibition even at a concentration of 100 g/ml.
To clarify the degradation pathway of chlorhexidine by a microbe, Pseudomonas sp. Strain No. A-3, the isolation and identification of microbial chlorhexidine degradation products were attempted. Two aromatic degradation products of chlorhexidine, named chlorhexidine aromatic degradation product (CHADP)-4 and CHADP-6, were isolated by column chromatography using Diaion HP-10, and purified by column chromatography using Diaion HP-20SS and Sephadex LH-20. The chemical structures of both compounds were examined by infrared, 1 H NMR, 13 C NMR and fast atom bombardment (FAB) mass spectra studies. Based on the spectroscopic data, CHADP-4 (molecular weight 335) and CHADP-6 (molecular weight 377) were found to be direct degradation products of chlorhexidine and were thought to be cleavage partners of p-chlorophenylurea (CHADP-5) and p-chloraniline (p-CA), respectively. Antimicrobial activity of CHADP-6 are similar to that of chlorhexidine, but antimicrobial activity of CHADP-4 decreased to 1/5-1/10 that of chlorhexidine.
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