Isolation of trehalamine, the aglycon of trehazolin, from microbial broths and characterization of trehazolin related compounds.
Trehalamine, (3aR,4R,5S,6S,6aS)-2-amino-4-(hydroxymethyl)-3a,5,6,6a- tetrahydro-4H-cyclo-pent[d]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, (1R,2S,3R,4S,5R)-5-amino-1- (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. SANK 62390 and Amycolatopsis sp. SANK 60791. 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.
Ando
O
O
Fermentation Research Laboratories, Sankyo Co., Ltd., Tokyo, Japan.
Nakajima
M
M
Hamano
K
K
Itoi
K
K
Takahashi
S
S
Takamatsu
Y
Y
Sato
A
A
Enokita
R
R
Okazaki
T
T
Haruyama
H
H
D039903:Actinobacteria / Q000145:classification / Q000378:metabolism; D000818:Animals; D012831:Bombyx; D004187:Disaccharides / Q000378:metabolism*; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D006868:Hydrolysis; D008847:Micromonospora / Q000145:classification / Q000378:metabolism; D015394:Molecular Structure; D009754:Nuts; D010080:Oxazoles / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D051381:Rats
D004187:Disaccharides; D010080:Oxazoles; C071816:trehazolin; C082789:trehalamine; D006026:Glycoside Hydrolases