Occurrence of the alpha-glucosidase inhibitor 1,4-Dideoxy-1,4-imino-D-arabinitol and related iminopentitols in marine sponges.
The alpha-glucosidase inhibitor 1,4-dideoxy-1,4-imino-D-arabinitol (1) was isolated from two marine sponges collected in Western Australia and shown by LC-MS to be responsible for the alpha-glycosidase inhibitory activity in different sponge extracts collected over a wide geographic area. The configuration of 1 was determined by application of Marfey's method. The two most inhibitory extracts contained only 1, while the less inhibitory extracts contained 1,4-dideoxy-1,4-imino-D-xylitol (2) or the putative diastereomeric imino pentitols 3 and 4. The least active or inactive extracts showed no detectable imino pentitols. While both 1 and 2 are known from plants, this is the first report on the isolation and detection of 1 and 2 in marine invertebrates.
Saludes
Jonel P
JP
Department of Chemistry, University of California-Davis, One Shields Avenue, Davis, CA 95616, USA.
Lievens
Sarah C
SC
Molinski
Tadeusz F
TF
D000818:Animals; D001089:Arabinose; D065089:Glycoside Hydrolase Inhibitors; D050113:Imino Furanoses; D015394:Molecular Structure; D011161:Porifera / Q000737:chemistry*; D013402:Sugar Alcohols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D014904:Western Australia; D014993:Xylitol / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D015003:Yeasts / Q000201:enzymology
C519149:1,4-dideoxy-1,4-imino-D-xylitol; D065089:Glycoside Hydrolase Inhibitors; D050113:Imino Furanoses; D013402:Sugar Alcohols; C058137:1,4-dideoxy-1,4-iminoarabinitol; D001089:Arabinose; D014993:Xylitol