Occurrence of the α-Glucosidase Inhibitor 1,4-Dideoxy-1,4-imino-d-arabinitol and Related Iminopentitols in Marine Sponges

• Published in: Journal of natural products (Washington, D.C.) Vol. 70; no. 3; pp. 436 - 438
• Main Authors: Saludes, Jonel P, Lievens, Sarah C, Molinski, Tadeusz F
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01-03-2007; Glendale, AZ American Society of Pharmacognosy
• Subjects: Animals; Arabinose; Biological and medical sciences; General pharmacology; Glycoside Hydrolase Inhibitors; Imino Furanoses; Medical sciences; Molecular Structure; Pharmacognosy. Homeopathy. Health food; Pharmacology. Drug treatments; Porifera - chemistry; Sugar Alcohols - chemistry; Sugar Alcohols - isolation & purification; Sugar Alcohols - pharmacology; Western Australia; Xylitol - analogs & derivatives; Xylitol - chemistry; Xylitol - isolation & purification; Xylitol - pharmacology; Yeasts - enzymology; Australia; Western Australia; Oceania; HPLC chromatography; Extract; Pyrrolidine derivatives; Marine environment; Iminoalditol; Enzyme; Coupled method; Pharmacognosy; Enzyme inhibitor; Animal origin; Geometrical configuration; In vitro; Biological activity; α-Glucosidase; Porifera; Glycosidases; Hydrolases; Isolation; Sponge; Invertebrata; Detection; O-Glycosidases; Mass spectrometry; Diastereomer; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np060551o

The α-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 α-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.