title: The hypoglycemic effect of (7R*,9aS*)-7-phenyl-octahydroquinolizin-2-one in mice.
abstract: (-)-Multiflorine (1), which was isolated from leguminous plants, produced a hypoglycemic effect when administered to mice with streptozotocin-induced diabetes. (-)-Multiflorine has an enaminone type conjugation on the A-ring, which is unusual in lupine alkaloids. Proceeding on the assumption that the A-B ring is responsible for the activity, several compounds bearing quinolizidin-2-one were synthesized and their hypoglycemic effects were examined. The hypoglycemic effect of (7R*,9aS*)-7-phenyl-octahydroquinolizin-2-one was approximately 4 times stronger than that of (-)-multiflorine measured by oral glucose tolerance test in normal mice. This result indicates that compounds possessing the quinolizidin-2-one ring system as the basic structure may be possible lead compounds for a new type of diabetes drug.
authors.affiliation: Institute of Medicinal Chemistry, Hoshi University, Tokyo, Japan. kubo@hoshi.ac.jp
authors.forename: H
authors.initials: H
authors.lastname: Kubo
authors.forename: J
authors.initials: J
authors.lastname: Kobayashi
authors.forename: K
authors.initials: K
authors.lastname: Higashiyama
authors.forename: J
authors.initials: J
authors.lastname: Kamei
authors.forename: Y
authors.initials: Y
authors.lastname: Fujii
authors.forename: S
authors.initials: S
authors.lastname: Ohmiya
mesh_terms: D000470:Alkaloids / Q000494:pharmacology*; D000818:Animals; D003921:Diabetes Mellitus, Experimental / Q000188:drug therapy; D007004:Hypoglycemic Agents / Q000494:pharmacology*; D008297:Male; D051379:Mice; D008813:Mice, Inbred ICR; D013237:Stereoisomerism; D013311:Streptozocin; D013329:Structure-Activity Relationship; D000093843:Quinolizidine Alkaloids
chemical_list: D000470:Alkaloids; D007004:Hypoglycemic Agents; D013311:Streptozocin; C417683:multiflorine; D000093843:Quinolizidine Alkaloids