Cytotoxic benzil and coumestan derivatives from Tephrosia calophylla.

A benzil, calophione A, 1-(6'-Hydroxy-1',3'-benzodioxol-5'-yl)-2-(6''-hydroxy-2''-isopropenyl-2'',3''-dihydro-benzofuran-5''-yl)-ethane-1,2-dione and three coumestan derivatives, tephcalostan B, C and D were isolated from the roots of Tephrosia calophylla. Their structures were deduced from spectroscopic data, including 2D NMR (1)H-(1)H COSY and (13)C-(1)H COSY experiments. Compounds were evaluated for cytotoxicity against RAW (mouse macrophage cells) and HT-29 (colon cancer cells) cancer cell lines and antiprotozoal activity against various parasitic protozoa. Calophione A exhibited significant cytotoxicity with IC(50) of 5.00 (RAW) and 2.90microM (HT-29), respectively.

Hepatoprotective activity of Macrothelypteris torresiana (Gaudich.) aerial parts against CCl4-induced hepatotoxicity in rodents and analysis of polyphenolic compounds by HPTLC.

Macrothelypteris torresiana is a fern species belonging to family Thelypteridaceae. The present study was conducted to evaluate hepatoprotective potential of ethanol extract from M. torresiana aerial parts (EEMTAP) and detect the polyphenolic compounds present in the extract using high performance thin layer chromatography (HPTLC). Hepatoprotective potential of EEMTAP were tested at doses of 300 and 600 mg/kg, per os (p.o.), on Wistar albino rats. The extract and silymarin treated animal groups showed significant decrease in activities of different biochemical parameters like serum glutamic oxaloacetic transaminase (SGOT), serum glutamate-pyruvate transaminase (SGPT), alkaline phosphatase (ALP), which were elevated by carbon tetrachloride (CCl4) intoxication. The levels of total bilirubin and total protein alongwith the liver weight were also restored to normalcy by EEMTAP and silymarin treatment. After CCl4 administration the level of hepatic antioxidant enzymes such as Glutathione (GSH) and Catalase (CAT) were decreased whereas the level of hepatic lipid peroxidation (LPO) was elevated. The level of these hepatic antioxidant enzymes were also brought to normalcy by EEMTAP and silymarin treatment. Histological studies supported the biochemical findings and treatment with EEMTAP at doses 300 and 600 mg/kg, p.o. was found to be effective in restoring CCl4-induced hepatotoxicity in rats. A simple HPTLC analysis was conducted for the detection of polyphenolic compounds in EEMTAP, and the result revealed the presence of caffeic acid as phenolic acid and quercetin as flavonoid. The proposed HPTLC method is simple, concise and provides a good resolution of caffeic acid and quercetin from other constituents present in EEMTAP.

Mono and dimeric naphthalene derivatives from the roots of Diospyros assimilis.

Three 2-naphthaldehydes, including the novel 4-hydroxy-3,5-dimethoxy-2-naphthaldehyde, the simple naphthoquinone plumbagin and the dimeric naphthoquinones diospyrin and 8'-hydroxyisodiospyrin have been isolated from the roots of Diospyrosassimilis and their structures established by spectroscopic analysis.

Antitermitic quinones from Diospyros sylvatica.

Six quinones were isolated from the chloroform extract of the roots of Diospyros sylvatica and identified as 2-methyl-anthraquinone, plumbagin, diosindigo, diospyrin, isodiospyrin and microphyllone. The effect of the root extract on the orientation and survival of the subterranean termite, Odontotermes obesus was tested. In addition, four of these quinones were tested on the survival of the subterranean termite. In a direct-choice experiment, exposure to an extract-treated filter disc had a significantly repellent effect over the solvent-treated filter disc. The no-choice experiment revealed the toxic property of the extract as well as the tested quinones and showed high mortality of the O. obesus workers after 48 h on forced exposure. The major termiticidal components identified were plumbagin, isodiospyrin and microphyllone while diospyrin was not toxic to termites at the concentration tested. All the quinones are reported for the first time from D. sylvatica.

Rare prenylated isoflavones from Tephrosia calophylla.

Chemical re-examination of the roots of T. calophylla led to the isolation of four isoflavones, namely 2',4',5-trihydroxy-6,7-(2",2"-dimethylchromene)-8-gamma,gamma-dimethylallylisoflavone (1a, auriculatin), 2',5-dihydroxy-6,7-(2",2"-dimethylchromene)-4'-gamma,gamma-dimethylallyloxyisoflavone (2a, isoauriculatin), 3',4',5-trihydroxy-6,7-(2",2"-dimethylchromene)-8-gamma,gamma-dimethylallylisoflavone (1b, auriculasin), and 3',5-dihydroxy-6,7-(2",2"-dimethylchromene)-4'-gamma,gamma-dimethylallyl-oxyisoflavone (2b, isoauriculasin). Auriculasin and isoauriculasin are reported for the first time with full NMR assignments. All metabolites were fully characterized by 1D and 2D NMR techniques including COSY, HSQC, HMBC experiments, mass spectra and in part on the basis of X-ray diffraction. Accurate 'invariom' refinements with aspherical scattering factors were carried out for 1a, 1b and 2a.

Hepatoprotective activity of Macrothelypteris torresiana (Gaudich.) aerial parts against CCl4-induced hepatotoxicity in rodents and analysis of polyphenolic compounds by HPTLC / 药物分析学报

Macrothelypteris torresiana is a fern species belonging to the family Thelypteridaceae. The present study was conducted to evaluate hepatoprotective potential of ethanol extract from M. torresiana aerial parts (EEMTAP) and detect the polyphenolic compounds present in the extract using high performance thin layerchromatography (HPTLC). Hepatoprotective potential of EEMTAP were tested at doses of 300 and 600 mg/kg, per os (p.o.), on Wistar albino rats. The extract and silymarin treated animal groups showed significant decrease in activities ofdifferent biochemical parameters like serum glutamic oxaloacetic transaminase(SGOT), serum glutamate-pyruvate transaminase (SGPT), and alkaline phosphatase (ALP), which were elevated by carbon tetrachloride (CCl4) intoxication. The levels of total bilirubin and total protein along with the liver weight were also restoredto normalcy by EEMTAP and silymarin treatment. After CCl4 administration, the levels of hepatic antioxidant enzymes such as glutathione (GSH) and catalase (CAT) were decreased whereas the level of hepatic lipid peroxidation (LPO) was elevated. The levels of these hepatic antioxidant enzymes were also brought to normalcy by EEMTAP and silymarin treatment. Histological studies supported the biochemical findings, and treatment with EEMTAP at doses of 300 and 600 mg/kg, p.o. was found to be effective in restoring CCl4-induced hepatotoxicity in rats. A simple HPTLC analysis was conducted for the detection of polyphenolic compounds in EEMTAP, and the result revealed the presence of caffeic acid as phenolic acid and quercetin as flavonoid. The proposed HPTLC method is simple and concise and provides a good resolution of caffeic acid and quercetin from other constituents present in EEMTAP.

A phenethyl bromo ester from Citharexylum fruticosum.

A new compound, (2S)-p-hydroxyphenethyl 2-bromo-2-methyldodeconate (1) and 7,3'-dimethoxy-5,4'-dihydroxy flavone, together with lupeol and stigmasterol were isolated from the stem bark of Citharexylum fruticosum (Verbenaceae). The structures of the compounds were established on the basis of the interpretation of NMR (1H, 13C, COSY and HMBC) spectra, as well as low and high-resolution mass spectrometric data. In this paper, we report on the structure elucidation of 1.

Phenolic glucosides from Flacourtia indica.

A new phenolic glucoside, (rel)-2-(4',6' -dibenzoyl-beta-glucopyranosyloxy)-7-(1alpha-hydroxy-2alpha-ethoxy-6alpha-acetyloxy-3-oxocyclohex-4-enoyl)-benzyl alcohol (Flacourticin) (1) and the known, 2-(4',6'-dibenzoyl-beta-glucopyranosyl)-5-hydroxy benzyl alcohol (4'-benzoylpoliothrysoside) (2) together with the new, (2E)-heptyl-3-(3,4-dihydroxyphenyl) acrylate (3), (+)-catechin (4) and sitosterol-beta-D-glucoside were isolated from Flacourtia indica. Their structures were assigned on the basis of 1D, 2D-NMR and as well by analysis of the LC-ESIMS data. The isolated compounds (1-4) were evaluated for alpha,alpha-diphenyl-beta-picrylhydrazyl (DPPH) radical scavenging activity, and 3 was found to be two-fold less potent, with an IC50 = 12.01 microg/mL, compared to the positive control, Rutin, (IC50 = 5.83 microg/mL).