Ranjeet Kaur

Synthesis and in vitro anticancer activity of brevifoliol derivatives substantiated by in silico approach

Five novel derivatives 1a, 1b, 1c, 2 and 3 of brevifoliol were synthesized. The structures of all the synthesized derivatives were established on the basis of IR, 1H NMR, 13C NMR and mass spectral data. All the five derivatives were tested for in vitro cytotoxicity against four human cancer cell lines. The result showed that compound 1a, 1b and 1c exhibited significant inhibition of cell growth. The mechanism of action of novel glucosidated derivatives have been explored by in silico molecular docking for anticancer activity against human lung, prostate and cervix cancer cell lines. Based on reported experimental activities on human cancer cell lines, specific molecular targets (e.g. microtubule in case of human lung cancer cell line A-549; indoleamine 2,3-dioxygenase in case of prostate cancer cell lines PC-3 and DU-145 and uridine phosphorylase 1 in case of Hela cell line) have been selected for docking studies and successfully validated for anticancer activity of brevifoliol derivatives.

High-performance liquid chromatographic method for identification and quantification of three potent liver protective coumarinolignoids-cleomiscosin A, cleomiscosin B and cleomiscosin C-in extracts of Cleome viscosa.

A simple, rapid, accurate and reproducible reverse-phase HPLC method has been developed for simultaneous identification and quantification of three coumarinolignoids, cleomiscosin A (Cliv A), cleomiscosin B (Cliv B) and cleomiscosin C (Cliv C) in different extracts of the seeds of Cleome viscosa using photodiode array detection at 326 nm. Cliv A, B and C were separated on a Waters symmetry C(18) column (250 x 4.6 mm, 5 microm) using the solvent system consisting of a mixture of acetonitrile : methanol (1:2 v/v) and water : acetic acid (99.5:0.5 v/v) as a mobile phase in a gradient elution mode. The calibration curves were linear in the concentration ranges 15-200, 10-80 and 15-180 microg/mL for Cliv A, Cliv B and Cliv C, respectively. The limits of detection and quantification for Cliv A, Cliv B and Cliv C were 15 and 20 microg/mL, 10 and 15 microg/mL and 15 and 20 microg/mL, respectively. The intra-day and inter-day precisions were 2.08 and 0.93% for Cliv A , 1.22 and 0.39% for Cliv B and 1.29 and 0.23 for Cliv C respectively. The developed HPLC method was used to identify and quantify Cliv A, Cliv B and Cliv C in different extracts of seed of Cleome viscosa.

High-performance liquid chromatography and LC-ESI-MS method for the identification and quantification of two biologically active isomeric coumarinolignoids cleomiscosin A and cleomiscosin B in different extracts of Cleome viscosa.

A rapid, sensitive and simple reverse-phase high-performance liquid chromatographic-electrospray ionization-mass spectrometry method for simultaneous determination of cleomiscosin A and cleomiscosin B has been developed and validated. The isomeric coumarinolignoids cleomiscosin A (1) and cleomiscosin B (2) were separated on a Waters symmetry C(18) column with a solvent system composed of acetonitrile-methanol (1:2) and acetic acid-water (0.5:99.5) in a gradient elution mode. The absorption at 326 nm was chosen as the measuring wavelength in which resolution and baseline separation of compounds 1 and 2 could be obtained. The identity of the two isomeric compounds 1 and 2 in the samples were determined on a triple quadrupole mass spectrometer with ESI interface operating in the positive mode. Calibration curves were linear (r(2) > 0.993) over the concentration range 20-200 microg/mL for cleomiscosin A and 10-200 microg/mL for cleomiscosin B with acceptable accuracy and precision, respectively. The intra-day and inter-day precision were 1.13 and 0.82% for cleomiscosin A and 1.78 and 1.28% for cleomiscosin B, respectively. The validated method was successfully applied for the analysis of the above two compounds in different extracts of Cleome viscosa.

(1S,5R,7R,30S)-14-De­oxy­isogarcinol

The title compound, C38H50O5 {systematic name: 10-(3-hydroxybenzoyl)-2,2,7,7-tetramethyl-3,6,8-tris(3-methylbut-2-enyl)-3,4,4a,5,6,7-hexahydro-4a,8-methano-2H-cycloocta[b]pyran-9,11(8H)-dione}, is a polyisoprenylated benzophenone, isolated for the first time from the fruits of Garcinia indica during our investigation of bioactive compounds from this plant and their large-scale extraction. The relative configuration of the title compound was chosen based on comparison of its spectroscopic and optical rotation data with that of the isomorphous and isostructural compound isogarcinol, whose absolute configuration is known. The crystal packing features O—H⋯O hydrogen bonds. A Cambridge Structural Database analysis revealed that the crystal structure reported here is isomorphous and isostructural with that of isogarcinol.

Identification and quantification of two antihepatotoxic coumarinolignoids cleomiscosin A and cleomiscosin B in the seeds of Cleome viscosa using liquid chromatography–tandem mass spectrometry

A sensitive liquid chromatography/electrospray ionization tandem mass spectrometric (LC/ESI-MS/MS) method was developed for the identification and quantification of two antihepatotoxic coumarinolignoids cleomiscosin A and cleomiscosin B in different extracts of the seeds of Cleome viscosa. The separation of cleomiscosin A and cleomiscosin B was achieved on an RP(18) column using a solvent system consisting of a mixture of acetonitrile-methanol (1:2, v/v) and acetonitrile-water-formic acid (5:95:0.3, v/v) as a mobile phase in a gradient elution mode. A multiple-reaction monitoring (MRM) method was developed for quantification of cleomiscosin A and cleomiscosin B in the seed extracts of Cleome viscosa. On the basis of signal-to-noise ratio of 3, the limit of detection in MRM mode for cleomiscosin A and cleomiscosin B were 1.0 and 4.0 ng/mL respectively. The method was validated in terms of linearity, accuracy and precision for 6 days. The method developed was found to be useful for identification and quantification of cleomiscosin A and cleomiscosin B in the different extracts of the seeds of Cleome viscosa.