lignans and elenoside

The dioxo-lignans of the arylnaphthalene-type named justicidone (2) and elenodione (3) were obtained from elenoside (1) through a short and efficient semisynthetic process. Justicidone (2), one of its synthetic precursors, 4-(benzo[d][1,3]dioxol-5-yl)-5,6,8-trimethoxy-3a,4-dihydronaphtho[2,3-c]furan-1(3H)-one (9), and the aglycone of elenoside (5) showed cytotoxic activity towards the HL-60 cell line (IC50 = 7.25 miroM, 5.41 microM and 2.06 miroM, respectively).

Topics: Acanthaceae; Antineoplastic Agents, Phytogenic; Cell Line, Tumor; Humans; Lignans; Molecular Structure; Quinones

To study the effects of elenoside, an arylnaph-thalene lignan from Justicia hyssopifolia, on gastro-intestinal motility in vivo and in vitro in rats.. Routine in vivo experimental assessments were catharsis index, water percentage of boluses, intestinal transit, and codeine antagonism. The groups included were vehicle control (propylene glycol-ethanol-plant oil-tween 80), elenoside (i.p. 25 and 50 mg/kg), cisapride (i.p. 10 mg/kg), and codeine phosphate (intragastric route, 50 mg/kg). In vitro approaches used isolated rat intestinal tissues (duodenum, jejunum, and ileum). The effects of elenoside at concentrations of 3.2 x 10(-4), 6.4 x 10(-4) and 1.2 x 10(-3) mol/L, and cisapride at 10(-6) mol/L were investigated.. Elenoside in vivo produced an increase in the catharsis index and water percentage of boluses and in the percentage of distance traveled by a suspension of activated charcoal. Codeine phosphate antagonized the effect of 25 mg/kg of elenoside. In vitro, elenoside in duodenum, jejunum and ileum produced an initial decrease in the contraction force followed by an increase. Elenoside resulted in decreased intestinal frequency in duodenum, jejunum, and ileum. The in vitro and in vivo effects of elenoside were similar to those produced by cisapride.. Elenoside is a lignan with an action similar to that of purgative and prokinetics drugs. Elenoside, could be an alternative to cisapride in treatment of gastrointestinal diseases as well as a preventive therapy for the undesirable gastrointestinal effects produced by opioids used for mild to moderate pain.

Topics: Acanthaceae; Animals; Codeine; Gastrointestinal Motility; In Vitro Techniques; Lignans; Male; Rats; Rats, Sprague-Dawley; Water

Elenoside is a cytotoxic arylnapthalene lignan (NSC 644013-W/1) derived from Justicia hyssopifolia (Family: Acanthaceae). The neuropharmacological activity of this lignan, a beta-D-glucoside was studied. The LD50 (24 h) of elenoside in mice is 305 +/- 7 mg/kg by i.p. route. In the present study elenoside was given to rats at doses of 25 and 50 mg/kg, and its effects on locomotor activity (Varimex test), muscular relaxant activity, open-field test and with chlorpromazine, 10 mg/kg was compared. On Varimex test, spontaneous activity was reduced. Elenoside produced a reduction in the permanence time on muscular relaxant activity (traction test). On open-field test, ambulation and rearing were reduced compared with the control group and an increase in boluses of dose-dependent rate was obtained. Thus it can be concluded that elenoside has central sedative effects and possible application in anxiety conditions.

Topics: Acanthaceae; Animals; Antidepressive Agents; Central Nervous System; Dose-Response Relationship, Drug; Injections, Intraperitoneal; Lethal Dose 50; Lignans; Male; Mice; Motor Activity; Phytotherapy; Plant Extracts; Plant Leaves; Rats; Rats, Sprague-Dawley

This paper deals with the effects of elenoside, (3-hidroxymethyl-1-methoxy-5,6-methylene-dioxy-4-(3,4-methylenedioxyphenyl)-2-naftoic acid lactone-beta-D-glucoside) an arylnaphthalene lignan with broad spectrum cytotoxicity in a human tumor cell line panel, isolated from Justicia hyssopifolia (Acanthaceae) grown in the Canary Islands (Spain), on isolated cardiac auricle of rabbits, urinary excretion of rats, and on isolated rat ileum. These effects, using a vehicle (propylene glycol-ethanol-plant oil-Tween 80 (40:10:50:2) as a standard, are presented. Elenoside at concentrations of 3.2x10(-4), 6.4 x 10(-4), and 1.2 x 10(-3) M produced an increase in the contraction force of auricles in a concentration-dependent way. At doses of 25 and 50 mg/kg, an antidiuretic effect and a decrease in sodium excretion were observed. Elenoside at concentrations of 3.2 x 10(-4), 6.4 x 10(-4) and 1.2 x 10(-3) M produced an increase in the contraction force of ileum in a concentration-dependent manner. Elenoside produced the concentration dependent inhibition of 86Rb uptake. These results indicate that elenoside has digitalis-like activity similar to mammalian lignans. Moreover, this lignan has an irritant effect on the gastrointestinal tract.

Topics: Acanthaceae; Animals; Dose-Response Relationship, Drug; Erythrocytes; Heart Rate; Humans; Ileum; In Vitro Techniques; Lignans; Male; Plant Extracts; Plant Leaves; Rabbits; Rats; Rats, Sprague-Dawley; Urination

Acute toxicity (24 h) and general behavior in mice of a lignan from Justicia hyssopifolia, a beta-D-glucoside (elenoside), was studied, and the cytotoxic activity was performed. Elenoside (arylnaphthalene lignan) in mice showed a moderate toxicity order (305 mg/kg) and central depressive properties at doses of 25, 50, and 100 mg/kg. It also displayed cytotoxic activity in a range of concentration of 10(-5)-10(-4) M when studied in the human tumor cell line panel of the US National Cancer Institute (NCI). The results indicated that elenoside has central depressant effects, and the cytotoxic activity of elenoside suggests that this compound and its genin derivatives merit further investigation as antitumoral drugs.

Topics: Animals; Antineoplastic Agents, Phytogenic; Behavior, Animal; Drug Screening Assays, Antitumor; Humans; Lethal Dose 50; Lignans; Male; Mice; Plants, Medicinal; Tumor Cells, Cultured

Cytotoxicity, acute toxicity, and general pharmacological effects in mice of an arylnaphthalene lignan isolated from Jisticia hyssopifolia were studied. Elenoside was cytotoxic to human cancer cell lines in a range of concentrations from 10(-5) to 10(-4)M. It has an LD(50), ip in mice, of 305 mg/kg and central depressive properties at doses of 25, 50, and 100 mg/kg. Thus, elenoside appears to be a sedative with broad spectrum cytotoxicity.

Topics: Animals; Antidepressive Agents; Antineoplastic Agents, Phytogenic; Humans; Lethal Dose 50; Lignans; Magnoliopsida; Male; Mice; Tumor Cells, Cultured