Homonojirimycin analogues and their glucosides from Lobelia sessilifolia and Adenophora spp. (Campanulaceae)

• Published in: Carbohydrate research Vol. 323; no. 1/4; pp. 73 - 80
• Main Authors: Ikeda, K, Takahashi, M, Nishida, M, Miyauchi, M, Kizu, H, Kameda, Y, Arisawa, M, Watson, AA, Nash, RJ, Fleet, GWJ, Asano, N
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier 12.01.2000
• Subjects: 1-Deoxynojirimycin - analogs & derivatives; Alkaloids - chemistry; Alkaloids - isolation & purification; Alkaloids - pharmacology; Animals; Asteraceae - chemistry; Biochemistry & Molecular Biology; Cattle; Chemistry; Chemistry, Applied; Chemistry, Organic; Glucosides - chemistry; Glycoside Hydrolases - antagonists & inhibitors; Imino Pyranoses; Inhibitory Concentration 50; Intestines - enzymology; Kidney - enzymology; Life Sciences & Biomedicine; Liver - enzymology; Magnetic Resonance Spectroscopy; Male; Physical Sciences; Piperidines - chemistry; Plant Extracts - chemistry; Plant Proteins - chemistry; Rats; Rats, Wistar; Science & Technology; Lobelia sessilifolia; INHIBITION; Adenophorae radix; PIG-KIDNEY TREHALASE; alpha-galactosidase inhibitor; 5-deoxyadenophorine-1-O-beta-D-glucoside; alpha-glucosidase inhibitor; Campanulaceae; ISOMERS; alpha-homonojirimycin derivative; 5-deoxyadenophorine
• ISSN: 0008-6215; 1873-426X

2,6-Dideoxy-7-O-(beta-D-glucopyranosyl) 2,6-imino-D-glycero-L-gulo-heptitol (7-O-beta-D-glucopyranosyl-alpha-homonojirimycin, 1) was isolated from the 50% methanol extract of the whole plant of Lobelia sessilifolia (Campanulaceae), which was found to potently inhibit rice alpha-glucosidase. Adenophorae radix, roots of Adenophora spp. (Campanulaceae), yielded new homonojirimycin derivatives, adenophorine (2), 1-deoxyadenophorine (3), 5-deoxyadenophorine (4), 1-C-(5-amino-5-deoxy-beta-D-galactopyranosyl)butane (beta-1-C-butyl-deoxygalactonojirimycin, 5), and the 1-O-beta-D-glucosides of 2 (6) and 4 (7), in addition to the recently discovered alpha-1-C-ethylfagomine (8) and the known 1-deoxymannojirimycin (9) and 2R,5R-bis(hydroxymethyl)-3R,4R-dihydroxypyrrolidine (DMDP, 10). Compound 4 is a potent inhibitor of coffee bean alpha-galactosidase (IC50 = 6.4 micromolar) and a reasonably good inhibitor of bovine liver beta-galactosidase (IC50 = 34 micromolar). Compound 5 is a very specific and potent inhibitor of coffee bean alpha-galactosidase (IC50 = 0.71 micromolar). The glucosides 1 and 7 were potent inhibitors of various alpha-glucosidases, with IC50 values ranging from 1 to 0.1 micromolar. Furthermore, 1 potently inhibited porcine kidney trehalase (IC50 = 0.013 micromolar) but failed to inhibit alpha-galactosidase, whereas 7 was a potent inhibitor of alpha-galactosidase (IC50 = 1.7 micromolar) without trehalase inhibitory activity.