Inhibitory effects of isorhamnetin-3-O-beta-D-glucoside from Salicornia herbacea on rat lens aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues.

The inhibitory effects of compounds from Salicornia herbacea (Chenopodiaceae) on rat lens aldose reductase (RLAR) and sorbitol accumulation in streptozotocin-induced diabetic rat tissues were investigated. The various fractions from the MeOH extract of S. herbacea were tested for their effects on RLAR in vitro. Among them, the EtOAc fraction was found to exhibit a potent RLAR inhibition (IC(50)=0.75 microg/ml), from which an active principle as a potent AR inhibitor was isolated and its chemical structure was elucidated as isorhamnetin-3-O-beta-D-glucoside (1) by spectral analysis. Compound 1 exhibited a potent RLAR inhibition in vitro, its IC(50) being 1.4 microM. Compound 1, when administered orally at 25 mg/kg in streptozotocin (STZ)-induced diabetic rats, caused not only a significant inhibition of serum glucose concentration but also sorbitol accumulation in the lenses, red blood cells (RBC), and sciatic nerves. These results indicate that compound 1 from S. herbacea is a leading compound for further study as a new drug for the prevention and/or treatment of diabetes and its complications.

Lignans from Acanthopanax chiisanensis having an inhibitory activity on prostaglandin E2 production.

The chloroform and the ethyl acetate fractions from the roots of Acanthopanax chiisanensis exhibited the significant inhibition of TPA-induced prostaglandin E(2) (PGE(2)) production in rat peritoneal macrophages. Five lignans were isolated from the chloroform fraction and their structures were elucidated as l-sesamin, helioxanthin, savinin, taiwanin C, and 3-(3,4-dimethoxybenzyl)-2-(3,4-methylenedioxybenzyl)butyrolactone. Among the lignans tested, taiwanin C showed the most potent inhibitory activity (IC(50) = 0.12 microM) on PGE(2) production with the relative order of potency, taiwanin C >> 3-(3,4-dimethoxybenzyl)-2-(3,4-methylenedioxybenzyl)butyrolactone > savinin = helioxanthin. l-Sesamin showed no inhibitory activity at 30 microM.

Anti-diabetic activities of fucosterol from Pelvetia siliquosa.

Fucosterol isolated from Pelvetia siliquosa was tested for its anti-diabetic activity in vivo. Fucosterol, when administered orally at 30 mg/kg in streptozotocin-induced diabetic rats, was caused a significant decrease in serum glucose concentrations, and exhibited an inhibition of sorbitol accumulations in the lenses. Fucosterol, when administered orally at 300 mg/kg in epinephrine-induced diabetic rats, was also caused an inhibition of blood glucose level and glycogen degradation. These results demonstrated that fucosterol is a main anti-diabetic principle from the marine algae P. siliquosa.

Constituents of the halophyte Salicornia herbacea.

Four compounds were isolated from Salicornia herbacea by repeated column chromatography. Their structures were identified as beta-sitosterol (1), stigmasterol (2), uracil (3), and isorhamnetin-3-O-beta-D-glucopyranoside (4) by spectral analysis and comparison with the published data.

A benzenoid from the stem of Acanthopanax senticosus.

Seven compounds were isolated from the stem of Acanthopanax senticosus by repeated column chromatography. Their structures were elucidated as isovanillin (1), (-)-sesamin (2), isofraxidin (3), (+)-syringaresinol (4), 5-hydroxymethylfurfural (5), eleutheroside B (6), and eleutheroside E (7) by spectral analysis. Among them, isovanillin (1) was isolated for the first time from the family Araliaceae.

Antiinflammatory activity of hyperin from Acanthopanax chiisanensis roots.

The chloroform and the ethyl acetate fractions from the roots of Acanthopanax chiisanensis exhibited a significant inhibition of prostaglandin E2 (PGE2) production in rat peritoneal macrophages stimulated by the protein kinase C activator, 12-O-tetradecanoylphorbol 13-acetate (TPA). Hyperin was isolated as an active principle from the ethyl acetate fraction. It suppressed not only PGE2 production but also nitric oxide (NO) production in vitro in a concentration dependent manner, their IC50, being 24.3 and 32.9 microM, respectively. Hyperin also caused a significant inhibition of increase in acetic acid-induced vascular permeability in mice in vivo.

Modulation of the activity of pro-inflammatory enzymes, COX-2 and iNOS, by chrysin derivatives.

Chrysin, a natural flavone compound found in plants, has anti-inflammatory activity that has been previously explained in part by the suppression of promoter activities of pro-inflammatory enzymes, cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS). Here we present evidence that several chrysin derivatives modulate the activities, as well as the expression, of COX-2 and iNOS enzymes. Nitrate production triggered by lipopolysaccharide (LPS) was suppressed by treatment of cultured Raw264.7 cells (mice macrophage/monocyte) with chrysin, 5-hydroxy-7-methoxyflavone (Ch-2), and 5,7-diacetylflavone (Ch-4). Interestingly, COX-2 enzyme was strongly inhibited by Ch-4 (IC(50)=2.7 microM) but not by other derivatives. Furthermore, the inhibition of COX enzyme by Ch-4 was selective for COX-2 over COX-1. Three-dimensional modeling showed that Ch-4 fits well into the binding pocket of COX-2. The modeling suggested that a hydrogen bond exists between the oxygen of the ketone group at the 7-position of Ch-4 and the hydroxyl group of Tyr355. Docking Ch-4 into the V523I mutant of COX-2 indicated that Ile523 of COX-1 might contribute to the selectivity of COX-2 over COX-1. Ch-4 showed no effect on iNOS activity. Chrysin and Ch-2 weakly inhibited iNOS enzyme activity in the hemoglobin assay, but the underlying mechanisms of inhibition of iNOS by chrysin are not understood.

Constituents from the non-polar fraction of Artemisia apiacea.

Five compounds of terpenoids and coumarins were isolated from the non-polar fraction of Artemisia apiacea by open column chromatography. Their structures were elucidated as alpha-amyrin (1), beta-amyrin (2), beta-sitosterol (3), 5,6,7-trimethoxycoumarin (4) and 6-methoxy-7,8-methylenedioxycoumarin (5) by chemical and spectroscopic analysis. This is the first report of the isolation of alpha-amyrin, beta-amyrin, 5,6,7-trimethoxycoumarin and 6-methoxy-7,8-methylenedioxycoumarin from this plant.

Anti-tumor activities of decursinol angelate and decursin from Angelica gigas.

The in vivo anti-tumor activities of decursinol angelate (1) and decursin (2) isolated from the roots of Angelica gigas were investigated. These two compounds, when administered consecutively for 9 days at 50 and 100 mg/kg i.p. in mice, caused a significant increase in the life span and a significant decrease in the tumor weight and volume of mice inoculated with Sarcoma-180 tumor cells. These results suggest that decursinol angelate (1) and decursin (2) from A. gigas have anti-tumor activities.

Anti-oxidant activities of the extracts from the herbs of Artemisia apiacea.

The anti-oxidant activities of the various fractions from the herbs of Artemisia apiacea were investigated. The n-hexane and n-butanol fractions were found to cause significant free radical scavenging effects on DPPH, their scavenging potencies as indicated in IC(50) values, being 230.1 and 183.7 microg/ml, respectively. The n-butanol fraction exhibited a significant decrease in serum transaminase activities elevated by hepatic damage induced by CCl(4)-intoxication in rats. All fractions tested exhibited a lipid peroxidation causing a significant decrease in MDA production in TBA-reactant assay. The n-butanol fraction was the strongest in the increase in the anti-oxidant enzymes such as hepatic cytosolic superoxide dismutase (SOD), catalase and glutathione peroxidase (GSH-px) activities in CCl(4)-intoxicated rats. These results suggest that the herbs of A. apiacea possess not only the anti-oxidant, but also the activities in CCl(4)-intoxicated rats. Especially, the n-butanol extract was found to cause significant increases in the rat liver cytosolic SOD, catalase, GSH-px activities as well as a significant decrease in the MDA production.

In vivo anti-oxidant activities of tectochrysin.

The anti-oxidant activities of tectochrysin, a major compound of propolis, were investigated. Tectochrysin exhibited a significant decrease in serum transaminase activities elevated by hepatic damage induced by CCl4-intoxication in rats. Tectochrysin tested exhibited a lipid peroxidation causing a significant decrease in MDA production in TBA-reactant assay. Tectochrysin was strong in the increase in the anti-oxidant enzymes such as hepatic cytosolic superoxide dismutase, catalase and glutathione peroxidase activities in CCl4-intoxicated rats. These results suggest that tectochrysin possess not only the anti-oxidant, but also the activities in CCl4-intoxicated rats. Especially, tectochrysin was found to cause significant increases in the rat liver cytosolic SOD, catalase, GSH-px activities as well as a significant decrease in the MDA production.

High-performance liquid chromatographic analysis of chrysin derivatives on a Nova-Pak C18 column.

A high-performance liquid chromatographic method has been developed for the separation and quantification of chrysin and synthetic chrysin derivatives (12 chrysin alkyl and 7 chrysin acyl derivatives). The chromatography was performed using a Nova-Pak C18 column. A RP-HPLC was performed by using a binary mixture (MeOH-10 mM H3PO4) as a mobile phase, and the column temperature was maintained at room temperature. A flow rate was 1.0 ml/min, and the effluent was monitored at a wavelenth of 280 nm. The retention times for chrysin acyl and alkyl derivatives were within 10 minutes and 20 minutes, respectively. The absolute recovery of samples were all over 96%. The detection limits were 0.1-18 ng at S/N = 3 ratio.

Sessiline, a new nitrogenous compound from the fruits of Acanthopanax sessiliflorus.

A new nitrogenous compound, named sessiline [5-(5-oxo-pyrrolidin-2-yloxymethyl)-furan-2-carbaldehyde (1)], was isolated from the fruits of Acanthopanax sessiliflorus, together with (-)-sesamin, scoparone, protocatechuic acid, ursolic acid, hyperin and 5-hydroxymethylfurfural by CC. The structures of these compounds were elucidated by physico-chemical and spectral analysis.

Phytochemical constituents from the fruits of Acanthopanax sessiliflorus.

Six compounds were isolated from the fruits of Acanthopanax sessiliflorus. Their structures were elucidated as (-)-sesamin, scoparone, protocatechuic acid, ursolic acid, hyperin and 5-hydroxymethylfurfural by physicochemical and spectroscopic analysis. Among them, scoparone, ursolic acid and 5-hydroxymethylfurfural were isolated for the first time from Acanthopanax species.

Phytochemical constituents from the herba of Artemisia apiacea.

Four compounds of a coumarin, a steroid and two flavonoids were isolated from the herba of Artemisia apiacea by open column chromatography. Their structures were elucidated as artemicapin C, apigenin, daucosterol and cacticin by chemical and spectroscopic analysis. This is the first report of the isolation of these compounds from this plant.

Arteminin, a new coumarin from Artemisia apiacea.

The isolation of 6,7-dimethoxycoumarin (1), 6-methoxy-7,8-methylenedioxycoumarin (2), 5,6-dimethoxy-7,8-methylenedioxycoumarin (3), 6-hydroxy-7,8-methylenedioxycoumarin (4) and 5-hydroxy-6,8-dimethoxycoumarin (arteminin) (5) is reported.