Oxyfunctionalization products of terpenoids with dimethyldioxirane and their biological activity.
Oxyfunctionalization of the bioactive terpenoids, ursolic acid acetate (1), oleanolic acid acetate (5), lupeol acetate (12), and kaurenic acid (17), with dimethyldioxirane (DMDO) was investigated. Treatment of the terpenoids with DMDO under mild conditions afforded a variety of oxidation and oxydegradation products to yield naturally occurring and/or novel compounds in one step. After chromatographic separation, the structures of the individual isolated products were determined using spectroscopic methods including several homonuclear (1H-1H) and heteronuclear (1H-13C) shift-correlated 2D-NMR techniques. The inhibitory activity of the terpenoid derivatives against alpha-glucosidase was investigated and compounds 1, 3, 7, and 9 were found to exhibit potent activity.
Ogawa
Shoujiro
S
Department of Chemistry, College of Humanities and Sciences, Nihon University, Nihon University, Sakurajosui, Tokyo, Japan.
Hosoi
Keiji
K
Ikeda
Noriaki
N
Makino
Mitsuko
M
Fujimoto
Yasuo
Y
Iida
Takashi
T
D000085:Acetates / Q000737:chemistry / Q000494:pharmacology; D004224:Diterpenes / Q000737:chemistry / Q000494:pharmacology; D004852:Epoxy Compounds / Q000737:chemistry / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D009828:Oleanolic Acid / Q000737:chemistry / Q000494:pharmacology; D010084:Oxidation-Reduction; D053978:Pentacyclic Triterpenes; D010946:Plants, Medicinal; D013729:Terpenes / Q000737:chemistry / Q000494:pharmacology*; D014315:Triterpenes / Q000737:chemistry / Q000494:pharmacology; D000520:alpha-Glucosidases / Q000378:metabolism*; D000097245:Ursolic Acid; D000094042:Lupanes
D000085:Acetates; D004224:Diterpenes; D004852:Epoxy Compounds; D009828:Oleanolic Acid; D053978:Pentacyclic Triterpenes; D013729:Terpenes; D014315:Triterpenes; D000520:alpha-Glucosidases; D000097245:Ursolic Acid; C051436:kaurenoic acid; C010480:lupeol; D000094042:Lupanes; C064455:dimethyldioxirane