Pancreatic Lipase-Inhibiting Triterpenoid Saponins from Fruits of Acanthopanax senticosus

Abstract

A increasing number of people are suffering from obesity, which is often associated with the development of type II diabetes, coronary heart diseases, hyperlipidemia, hypertension, and metabolic syndrome.1,2) It is well known that pancreatic lipase plays an important role in lipid digestion. The inhibition of pancreatic lipase reduces the efficiency of dietary fat absorption in the small intestine and thereby promotes modest long-term reduction in body weight. 3)Acanthopanax senticosus (RUPR. et MAXIM.) HARMS. is a shrub, belonging to the family Araliaceae, which is commonly distributed in the northeast of Asia. Different parts of the plant have been widely used as traditional Chinese medicines for the treatment of a variety of human diseases, such as ischemic heart diseases, neurasthenia, hypertension, arthritis, and tumors.4) Recently, we have reported fifteen triterpenoid saponins from the leaves of A. senticosus, among which ciwujianoside C 1 , tauroside H 1 , 3-O-a-L-rhamnopyranosyl-(1→2)-a -L-arabinopyranosyl mesembryanthemoidigenic acid, acanthopanaxoside C, sessiloside, and chiisanoside exhibited pancreatic lipase inhibitory activity in vitro.5) The occurrence of triterpenoid saponins has also been demonstrated in a previous chemical investigation of the fruits of A. senticosus.6) As our continuous investigation on bioactive triterpenoid saponins 5,7-9) and our current interest in the natural lipase inhibitors, 5,9,10) we initiated a chemical investigation of the fruits of A. senticosus. The total saponin fraction exhibited inhibitory activity on pancreatic lipase with the IC 50 value of 3.63 mg/ml. Further isolation of this fraction resulted in the isolation of sixteen triterpenoid saponins (1-16), including a new compound, acanthopanaxoside E (1). The biological activities of 1-16 against pancreatic lipase were examined. Silphioside F (2), 11) copteroside B (3), Results and DiscussionThe air-dried fruits of A. senticosus were extracted with 70% EtOH. The 70% EtOH extract was suspended in H 2 O and then partitioned successively with EtOAc and n-BuOH. The n-BuOH soluble fraction was subjected to a Diaion HP-20 column, followed by washing with H 2 O and 50% MeOH to remove phenolic compounds, and then with MeOH to result in a crude saponin fraction, which inhibited pancreatic lipase (IC 50 value: 3.63 mg/ml). Further isolation of this fraction by combination of silica gel column chromatography (CC), ODS CC and preparative HPLC afforded sixteen triterpenoid saponins, including a new compound, acanthopanaxoside E (1). The known saponins were identified as silphioside F (2), China. Received February 7, 2007; accepted April 19, 2007; published

Experimental addition of Eleutherococcus senticosus and probiotic to the canine diet

“…Other authors detected a similar decrease of LDL cholesterol (P<0.001) whereas total cholesterol and triglyceride were not changed in blood serum of postmenopausal women supplemented with leaf extract for 6 months [10]. Although an inhibitory activity towards pancreatic lipase showed E. senticosus compounds [42], more detailed studies are needed to establish the exact mechanism of hypolipaemic action. Hepatoprotective effects are ascribed to certain E. senticosus components (e.g.…”

Two New Guaiane-Type Sesquiterpene Glycosides from the Fruits of Daucus carota L.

“…The mixture was kept at 60°C for 1.5 h. After the reaction mixture was dried in vacuo, the residue was trimethylsilylated with 1-trimethylsilylimidazole (0.1 ml) for 2 h. The mixture was partitioned between n-hexane and H 2 O (0.3 ml each) and then the n-hexane extract was analyzed by GC-MS under the following conditions: capillary column, EQUITY TM -1 (30 mϫ0.25 mmϫ0.25 mm, Supelco); column temperature, 230°C; injection temperature, 250°C; carrier N 2 gas; detection in EI mode, ionization potential, 70 eV; ion-source temperature, 280°C. 16,19) D-Glucose in 1 was confirmed by comparison of the retention times of its derivatives with those of standard Dglucose and L-glucose derivatives prepared in a similar way which showed retention times of 11.25 and 10.79 min, respectively. Sugar in 2 (1.0 mg) was also identified by the same method.…”

“…The previous research on chemical constituents of D. carota has carried out the presence of sesquiterpenes, [6][7][8] chromones, 9) flavonoids, 10,11) coumarins 6,12) and anthocyanins. 13,14) As a part of our ongoing investigation on bioactive constituents, [15][16][17][18] we initiated a phytochemical investigation on the fruits of D. carota L., which resulted in the isolation of two new guaiane-type sesquiterpene glycosides, 11-O-acetyl-torilolone 8-O-b-D-glucopyranoside (1) and 1b-hydroxytorilolone 11-O-b-D-glucopyranoside (2). In this paper, we report the isolation and structure elucidation of them.…”

Efeito hipolipidêmico do suco de camu-camu em ratos

“…A possível explicação para esse resultado é a ação dos flavonoides sobre a inibição da lipase pancreática, que impede a absorção de lipídeos em nível intestinal, acarretando maior excreção de gordura nas fezes 33 .…”