Trehalamine, (3a^,4i?,55',65,6a5')-2-amino-4-(hydroxymethyl)-3a,5,6,6a-tetrahydro-4//-cyclopent[J]oxazole-4,5,6-triol (1) and D-glucose were obtained by acid hydrolysis of trehazolin (3), a trehalase inhibitor produced by actinomycetes. More vigorous hydrolytic treatment of trehazolin afforded an aminocyclitol, ( 1 R,2S,3R,4S,5R)-5-amino-l -(hydroxymethyl)cyclopentane-1 ,2,3,4-tetraol (2). Trehalamine, the aglycon of trehazolin, was also found in the culture broths of two trehazolin producing strains, Micromonospora sp. SANK62390 and Amycolatopsis sp. SANK60791. These trehazolin related compounds trehalamine (1) and 2 were poor inhibitors of trehalase (1; IC501.8 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 10~5m) and sweet almond /?-glucosidase (2; IC50 5.6 x 10"6m) than trehazolin.In the previous paper, we reported the isolation and characterization of trehazolin (3), an inhibitor of trehalase produced by Micromonospora sp. SANK623901}. Trehazolin showed a specific and potent inhibitory activity against trehalase and was shown to have a glucosyl moiety and a unique aglycon part in its structure. Since the aglycon portion of trehazolin seems to account for the trehalase inhibitory activity, it will be informative to assess the enzyme inhibitory properties of the aglycon to understand the nature of the activity of trehazolin. Furthermore, in respect to the microbial biosynthesis of the unique metabolite, it is of interest if the aglycon itself is present in the broths of the trehazolin producing microorganisms. Therefore, we attempted to characterize the aglycon and related compounds by hydrolysis of trehazolin and further to discover them from culture broths of trehazolin producers.On the first attempt of acidic hydrolysis of trehazolin at 100°C, the sole product was a 5-membered Fig. 1. The structures of trehalamine (1), 2, and trehazolin (3).