Medicinal foodstuffs. XXV. Hepatoprotective principle and structures of ionone glucoside, phenethyl glycoside, and flavonol oligoglycosides from young seedpods of garden peas, Pisum sativum L.

A new ionone glucoside, pisumionoside, a phenethyl glycoside, sayaendoside, and two acylated flavonol oligoglycosides, pisumflavonosides I and II, were isolated from the young seedpods of garden peas, Pisum sativum L., together with quercetin and kaempferol 3-O-(6-O-trans-p-coumaroyl)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosyl (1-->2)-beta-D-glucopyranosides and quercetin and kaempferol 3-sophorotriosides. The structures of pisumionoside, sayaendoside, and pisumflavonosides I and II were determined on the basis of chemical and physicochemical evidence, respectively. Quercetin 3-sophorotrioside, a principle component, was found to show protective effects on liver injury induced by D-galactosamine and lipopolysaccharide and by carbon tetrachloride in mice.

Hepatoprotective constituents from zedoariae rhizoma: absolute stereostructures of three new carabrane-type sesquiterpenes, curcumenolactones A, B, and C.

New carabrane-type sesquiterpene lactones, curcumenolactones A, B, and C, were isolated from the 80% aqueous acetone extract of Zedoariae Rhizoma (Zingiberaceae), together with 41 sesquiterpenes and two diarylheptanoids. The absolute stereostructures of curcumenolactones A, B, and C were determined on the basis of physicochemical evidence, which included nuclear Overhauser effect (NOE) and circular dichroic (CD) spectroscopic analyses. Curcumenone, a principal carabrane-type sesquiterpene from Zedoariae Rhizoma, was found to show potent protective effect on D-galactosamine/lipopolysaccharide-induced acute liver injury in mice. In addition, curcumenolactones A and B and the other constituents showed protective effect on D-galactosamine-induced cytotoxicity in primary cultured rat hepatocytes.

Hepatoprotective and nitric oxide production inhibitory activities of coumarin and polyacetylene constituents from the roots of Angelica furcijuga.

The methanolic extract from the roots of Angelica furcijuga KITAGAWA was found to exhibit protective effects on liver injury induced by D-galactosamine (D-GalN) and lipopolysaccharide (LPS). From the methanolic extract, seventeen coumarins, two phenylpropanoids, and two polyacetylenes were isolated and examined their in vitro and in vivo hepatoprotective effects and inhibitory activity of NO production in macrophages. A acylated khellactone, isoepoxypteryxin, showed protective activity against D-GalN-induced cytotoxicity in primary cultured rat hepatocytes. On the other hand, six acylated khellactones (hyuganins A, B, C, and D, anomalin, isopteryxin) and two polyacetylenes [(-)-falcarinol and falcarindiol] strongly inhibited NO production induced by LPS in cultured mouse peritoneal macrophages, and also other acylated khellactones (isoepoxypteryxin, pteryxin, and suksdorfin) and a coumarin glycosides (praeroside II) were found to show the activity. By comparison of the inhibitory activities for acylated khellactones with those for other coumarins, acyl groups were found to be essential to exerting potent activity.

Hepatoprotective, superoxide scavenging, and antioxidative activities of aromatic constituents from the bark of Betula platyphylla var. japonica.

The 50% aqueous methanolic extract from the bark of Betula platyphylla SUKATCHEV var. japonica (MIQ). HARA was found to show potent inhibitory activity on the liver-injury induced by CCl4 or D-galactosamine (D-GalN)/lipopolysaccharide as well as O2- scavenging and antioxidative activities. From the 50% aqueous methanolic extract, two new diarylheptanoids named betulaplatosides Ia (1) and Ib (2) and a new arylbutanoid named betulaplatoside II (3) were isolated together with seventeen known aromatic constituents. 1, 2, and two known diarylheptanoids [(5S)-5-hydroxy-1,7-bis-(4-hydroxyphenyl)-3-heptanone 5-O-beta-D-apiofurano-syl-(1-->6)-beta-D-glucopyranoside (6) and aceroside VIII (7)] showed protective activity against D-GalN-induced cytotoxicity in primary cultured rat hepatocytes. Furthermore, several aromatic constituents exhibited potent O2- scavenging and antioxidative activities.

[Bioactive constituents of Chinese natural medicines. III. Absolute stereostructures of new dihydroflavonols, hovenitins I, II, and III, isolated from hoveniae semen seu fructus, the seed and fruit of Hovenia dulcis THUNB. (Rhamnaceae): inhibitory effect on alcohol-induced muscular relaxation and hepatoprotective activity].

The methanol-soluble fraction from a Chinese natural medicine Hoveniae Semen Seu Fructus, the seed and fruit of Hovenia dulcis THUNB. (Rhamnaceae) was found to show an inhibitory effect on the alcohol-induced muscular relaxation and a protective activity on the D-galactosamine/lipopolysaccharide or carbon tetrachloride-induced liver injury. Through bioassay-guided separation using a traction performance test, three new dihydrofravonols named hovenitins I, II, and III were isolated from Hoveniae Semen Seu Fructus together with four known flavonoids, (+)-ampelopsin, laricetrin, myricetin, and (+)-gallocatechin. The absolute stereostructures of hovenitins I, II, and III were determined on the basis of chemical and physicochemical evidence to be (2R, 3R)-5,7,4',5'-tetrahydroxy-3'-methoxydihydroflavonol, (2R,3S)-5,7,4',5'-tetrahydroxy-3'-methoxy-dihydroflavonol, and (2R, 3S)-5,7,3',4',5'-pentahydroxydihydro-flavonol, respectively. Hovenitin I and (+)-ampelopsin, both of which were principal ingredients of the active fractions from this natural medicine, were found to show an inhibitory activity on the ethanol-induced muscle relaxation in rats. In addition, hovenitin I showed a protective activity on the liver injury induced by D-galactosamine/lipopolysaccharide or carbon tetrachloride in mice.

Substituted (omega-aminoalkoxy) stilbene derivatives as a new class of anticonvulsants.

A series of substituted (omega- aminoalkoxy )stilbene derivatives has been synthesized and screened for anticonvulsant activity. The effect of structural modification of these molecules on the activities has been systematically examined. Potent anticonvulsant activity was displayed by 2-[4-(4-methyl-1 piperazinyl)butoxy]stilbene (20) and some 2-[4-(3-alkoxy-1-piperidino)butoxy]stilbene derivatives (21, 37, 38, and 40), as determined by maximal electroshock seizure (MES) and pentylenetetrazol-induced convulsion tests in mice. Compound 21 exhibited more potent anti-MES activity than diphenylhydantoin and carbamazepine in further pharmacological tests in rats, and its therapeutic index was superior to those of two antiepileptic drugs.