Periandradulcins A, B and C: phosphodiesterase inhibitors from Periandra dulcis Mart.
During the course of our screening of bioactive natural products, three new saponins named periandradulcins A (1), B (2) and C (3) were isolated as phosphodiesterase (PDE, EC 3.1.4.17) inhibitors from 80% MeOH extract of the roots of Periandra dulcis Mart. (Leguminosae) by a combination of column chromatography and reversed- and normal-phase high-performance liquid chromatography (HPLC). On the basis of 1H-, 13C- and two-dimensional nuclear magnetic resonance (NMR) spectral data and chemical evidence, their chemical structures were characterized as 3-O-beta-[alpha-L-rhamnopyranosyl(1----2)-beta-D-xylopyranosyl(1----2)-b eta-D- glucuronopyranosyl]-30-hydroxyl-25-formylolean-18-ene-22 beta-O-syringate, 3-O-beta-[alpha-L-rhamnopyranosyl(1----2)-beta-D- xylopyranosyl(1----2)-beta-D-glucuronopyranosyl]-22 beta-hydroxyl-25- formylolean-12-ene and 3-O-beta-[alpha-L-rhamnopyranosyl(1----2)-beta-D- glucopyranosyl(1----2)-beta-D-glucuronopyranosyl]-22 beta-hydroxyl-25-formylolean-18-ene, respectively. The concentrations of periandradulcins A, B and C required to give 50% inhibition (IC50 values) of PDE from bovine heart, were 0.033, 7.6 and 7.7 microM, respectively. Compound 1 was the most potent among the known PDE inhibitors; it inhibited PDE-I (IC50:0.0022 microM) twenty and forty times more effectively than PDE-II and -III, respectively.
Ikeda
Y
Y
Research Division, Green Cross Corp., Osaka, Japan.
Sugiura
M
M
Fukaya
C
C
Yokoyama
K
K
Hashimoto
Y
Y
Kawanishi
K
K
Moriyasu
M
M
D002240:Carbohydrate Sequence; D007887:Fabaceae / Q000032:analysis*; D008969:Molecular Sequence Data; D009828:Oleanolic Acid / Q000031:analogs & derivatives*; D010726:Phosphodiesterase Inhibitors / Q000737:chemistry / Q000302:isolation & purification*; D010946:Plants, Medicinal; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
D010726:Phosphodiesterase Inhibitors; D012503:Saponins; C069839:periandradulcin A; C069840:periandradulcin B; C069842:periandradulcin C; D009828:Oleanolic Acid