ISOLATION ON TREHALAMINE, THE AGLYCON OF TREHAZOLIN, FROM MICROBIAL BROTHS AND CHARACTERIZATION OF TREHAZOLIN RELATED-COMPOUNDS

Trehalamine, ,6a-tetrahydro-4H-cyclo-pentd!oxazole-4,5,6-triol (1) an d D-glucose were obtained by acid hydrolysis of trehazolin (3), a treh alase inhibitor produced by actinomycetes. More vigorous hydrolytic tr eatment of trehazolin afforded an aminocyclitol, mino-1-(hydroxymethyl )cyclopentane-1,2,3,4-tetraol (2). Trehalamine, the aglycon of trehazo lin, was also found in the culture broths of two trehazolin producing strains, Micromonospora sp. SANK 62390 and Amycolatopsis sp. SANK 6079 1. These trehazolin related compounds trehalamine (1) and 2 were poor inhibitors of trehalase (1; IC50 1.8 x 10(-4) m, 2; > 5.0 x 10(-4) m). On the other hand they inhibited more potently rat intestinal sucrase (1; IC50 6.8 x 10(-5) m) and sweet almond beta-glucosidase (2; IC50 5 .6 x 10(-6) m) than trehazolin.