Long-term stability in biomass and production of terpene indole alkaloids by hairy root culture of Rauvolfia serpentina and cost approximation to endorse commercial realism.

The effect of 6 years of cultivation and use of table-sugar (TS) on the biomass/terpene alkaloid productivities and rol gene expression were studied in a hairy root (HR) clone of Rauvolfia serpentina. The media cost could be reduced >94 % by replacing sucrose (SUC) with TS—an unexplored avenue for HR cultivation. The overall productivities increased over long-term cultivation with sugar proving superior to SUC for biomass (24.

Novel chemical constituents with anti-inflammatory activity from the leaves of Sesbania aculeata.

From the hexane and ethyl acetate extracts of the leaves of Sesbania aculeata, three novel chemical compounds were isolated and fully characterized as compound 1, (ceramide type); compound 2, (cerebroside type) and compound 3 as a triterpene acid 3-O-α-L-rhamnopyranoside along with nine known compounds (Tricontanol, Lauric acid, Palmitic acid, Heptadecanoyl-1-tridecanoic acid, β-sitosterol, stigmasterol, poriferasterol glucoside, ononitol and pinitol). The anti-inflammatory potential of all three compounds were evaluated using in vitro target based anti-inflammatory activity in LPS-stimulated macrophages. TNF-α is one of the mediators of various chronic inflammatory disorders and treatment of hexane leaf extract (HL), Ethyl acetate leaf extract (EAL) and compounds 1, 2 and 3 at a dose of 10 μg/mL showed significant (P<0.

A validated HPLC-PDA method for identification and quantification of two bioactive alkaloids, ephedrine and cryptolepine, in different Sida species.

A simple, rapid, accurate and reproducible reverse-phase HPLC method has been developed for the identification and quantification of two alkaloids ephedrine and cryptolepine in different extracts of Sida species using photodiode array detection. Baseline separation of the two alkaloids was achieved on a Waters RP-18 X-terra column (250 × 4.6 mm, 5 µm) using a solvent system consisting of a mixture of water containing 0.

The potential health benefit of polyisoprenylated benzophenones from Garcinia and related genera: ethnobotanical and therapeutic importance.

The diversity present in biological activities and the medicinal significance of natural products provide a renewed interest in the use of natural compounds and, more importantly, their role as a basis for drug development. Advancements in the field of natural product chemistry provide valuable information on Garcinia fruits which revealed the presence of biologically important secondary metabolites named as polyisoprenylated benzophenones (PIBs). They are mainly present in the genus Garcinia (Guttiferae) which occupies a prominent position in the history of natural products.

QSAR, docking and in vitro studies for anti-inflammatory activity of cleomiscosin A methyl ether derivatives.

A series of five (6a-8b) novel polyhalogenated derivatives and an interesting ester (9a) derivative have been synthesized from cleomiscosin A methyl ether. All the six derivatives were subjected to in silico QSAR modeling and docking studies and later the predicted results were confirmed through in vitro experiments. QSAR modeling results showed that compounds 6a and 9a possessed anti-inflammatory activity comparable or even higher than diclofenac sodium.

(1S,5R,7R,30S)-14-De-oxy-isogarcinol.

The title compound, C(38)H(50)O(5) {systematic name: 10-(3-hy-droxy-benzo-yl)-2,2,7,7-tetra-methyl-3,6,8-tris-(3-methyl-but-2-en-yl)-3,4,4a,5,6,7-hexa-hydro-4a,8-methano-2H-cyclo-octa-[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.

In silico exploration of anti-inflammatory activity of natural coumarinolignoids.

Natural coumarinolignoids isolated from the seeds of Cleome viscosa consist of a racemic mixture of cleomiscosins A, B and C. To screen out potential lead, anti-inflammatory activity of the isolated compounds was evaluated through molecular docking and QSAR studies by using reported in vivo activity of Swiss albino mice. Based on docking binding affinity, a possible mechanism of action has been hypothesized which constitute toll-like receptors (TLR-4), cluster of differentiation molecules (CDs), iNOS, COX-2 and STAT-6 proteins.

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.

High-performance liquid chromatography and LC-ESI-MS method for identification and quantification of two isomeric polyisoprenylated benzophenones isoxanthochymol and camboginol in different extracts of Garcinia species.

A rapid, sensitive and simple reverse-phase high-performance liquid chromatography-electrospray ionization mass spectrometric method has been developed for the identification and quantification of two isomeric polyisoprenylated benzophenones, isoxanthochymol and camboginol, in the extracts of the stem bark, seeds and seed pericarps of Garcinia indica and in the fruit rinds of Garcinia cambogia. The separation of isoxanthochymol and camboginol was achieved on a Perkin Elmer RP(8) column (10 x 2.1 mm with 5.

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.

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.

Expression of tropane alkaloids in the hairy root culture of Atropa acuminata substantiated by DART mass spectrometric technique.

Agrobacterium rhizogenes-mediated 'hairy root' cultures were established in Atropa acuminata. The chemical profiling of the hairy roots was carried out by a new mass spectrometric technique, direct analysis in real time (DART). The intact hairy roots were directly analyzed by holding them in the gap between the DART ion source and mass spectrometer.

Analysis of hairy root culture of Rauvolfia serpentina using direct analysis in real time mass spectrometric technique.

The applicability of a new mass spectrometric technique, DART (direct analysis in real time) has been studied in the analysis of the hairy root culture of Rauvolfia serpentina. The intact hairy roots were analyzed by holding them in the gap between the DART source and the mass spectrometer for measurements. Two nitrogen-containing compounds, vomilenine and reserpine, were characterized from the analysis of the hairy roots almost instantaneously.

Cytotoxic activities of xanthochymol and isoxanthochymol substantiated by LC-MS/MS.

The methanol extract of the fruit rinds of Garcinia indica showed potent cytotoxic activity against three human cancer cell lines, colon (COLO-320-DM), breast (MCF-7) and liver (WRL-68), as determined by the MTT assay. Fractionation of the methanol extract into hexane-, chloroform- and ethyl acetate-soluble fractions and evaluation of cytotoxic activity of each of the fractions revealed that the ethyl acetate fraction was the most effective as compared to the two other fractions. Two polyisoprenylated benzophenones, xanthochymol and isoxanthochymol, were isolated from the ethyl acetate fraction.

Syntheses and cytotoxicities of the analogues of the taxoid brevifoliol.

Seven novel brevifoliol analogues have been synthesized by coupling brevifoliol and 2-monosubstituted-4-phenyl-1,3-oxazolidine carboxylic acid after removal of the protecting group with acid treatment. Brevifoliol and its synthesized analogues were tested for their cytotoxic activities against four different human cancer cell lines, oral (KB), breast (MCF-7), colon (CaCO2) and liver (HepG-2) as determined by MTT assay. The C-13 oxidized brevifoliol retained significant activity.

Analysis of cell cultures of Taxus wallichiana using direct analysis in real-time mass spectrometric technique.

The applicability of a new mass spectrometric technique, DART (direct analysis in real time) has been studied in the analysis of the calli of Taxus wallichiana. The intact callus samples were directly analyzed by holding them in the gap between the DART source and mass spectrometer for measurements. Five C-14 oxygenated taxoids were characterized from the analysis of the calli of the Taxus wallichiana almost instantaneously.

High-performance liquid chromatographic method for identification and quantification of two isomeric coumarinolignoids-cleomiscosin A and cleomiscosin B-in extracts of Cleome viscosa.

A simple, accurate and reproducible reverse-phase HPLC method has been developed for identification and quantification of two isomeric coumarinolignoids, cleomiscosin A and B in different extracts of the seeds of Cleome viscosa using photodiode array detection at 326 nm. Cleomiscosin A and B were separated on a Waters symmetry C(18) column (250 x 4.6 mm with 5.

Liquid chromatography-tandem mass spectrometry method for identification and quantification of two biologically active polyisoprenylated benzophenones, isoxanthochymol and camboginol, in Garcinia species.

A sensitive liquid chromatography/electrospray ionization tandem mass spectrometrical (LC/ESI-MS/MS) method was developed for simultaneous identification and quantification of two polyisoprenylated benzophenones, isoxanthochymol and camboginol, in the extracts of the fruit rinds, stem bark, seed and leaves of Garcinia indica and in the fruit rinds of Garcinia cambogia. The separation of isoxanthochymol and camboginol was achieved on an RP-8 column using the solvent system consisting of a mixture of acetonitrile-water (80:20) and methanol-acetic acid (99.0:1.

High-performance liquid chromatography and LC-ESI-MS method for the identification and quantification of two biologically active polyisoprenylated benzophenones xanthochymol and isoxanthochymol in different parts of Garcinia indica.

A reverse-phase high-performance liquid chromatographic method was developed for qualitative and quantitative analysis of xanthochymol (1), and isoxanthochymol (2) in the fruit rinds, leaves and seed pericarps of Garcinia indica with confirmation using PDA detection and electrospray ionization MS. Absorption at 276 nm was chosen as the measuring wavelength at which resolution and baseline separation of compounds (1) and (2) could be obtained. The identity of the above two isomeric compounds (1) and (2) in the samples was unambiguously determined by their respective quasi-molecular ion [M - H]- in ESI-MS.

A rapid liquid chromatography-tandem mass spectrometry method for quantification of a biologically active molecule camboginol in the extract of Garcinia cambogia.

A liquid chromatography-tandem mass spectrometry (LC-MS/MS) method for the determination of camboginol in the extract of fruit rinds of Garcinia cambogia has been developed. Separation was achieved isocratically on an RP C(18) column using a solvent system consisting of a mixture of acetonitrile-water (9:1) and methanol-acetic acid (99.5:0.

Identification and quantification of two biologically active polyisoprenylated benzophenones xanthochymol and isoxanthochymol in Garcinia species using liquid chromatography-tandem mass spectrometry.

A sensitive liquid chromatography/electrospray ionization tandem mass spectrometrical (LC/ESI-MS/MS) method was developed for the identification and quantification of two polyisoprenylated benzophenones xanthochymol and isoxanthochymol in the extracts of the fruit rinds, stem bark, seed pericarps and leaves of Garcinia indica and in the fruit rinds of Garcinia cambogia. The separation of xanthochymol and isoxanthochymol was achieved on a RP-18 column using the solvent system consisting of a mixture of acetonitrile-water (9:1) and methanol-acetic acid (99.5:0.

Taxoid from the needles of the Himalayan yew Taxus wallichiana with cytotoxic and immunomodulatory activities.

The needles of Taxus wallichiana gave a taxoid 1-hydroxy- 2-deacetoxy-5-decinnamoyl-taxinine j, whose structure has been established by spectroscopic data and confirmed by X-ray crystallography. The taxoid possesses significant cytotoxic and immunomodulatory activity.

Synthesis of a novel plant growth promoter from gallic acid.

Gallic acid has been modified to naphthophenone derivatives with esterified fatty acid side chain. Compound 12, an ethyl crotonate ester of naphthophenone derivative has shown potent auxin like growth promoter activity. This is the first example of naphthophenone derivatives with plant growth promoting activity.

Betuligenol derivative with growth inhibition and antifeedant activity.

The title chiral amine, 3-(4-methoxyphenyl)-1-methylpropylamine 5 has been synthesized from naturally abundant betuligenol 1 in three steps and also in good yield. Furthermore, the versatile intermediate 3 could be manipulated for the preparation of chiral disulphide 7. The amine derivative 5 prepared from (-)-betuligenol showed significant growth inhibition and antifeedant activity.

Absolute configuration and anticancer activity of taxiresinol and related lignans of Taxus wallichiana.

Absolute configuration of taxiresinol 1, a lignan from the heartwood of Taxus wallichiana has been determined as 8R, 8'R, and 7'R with the help of chemical correlation method and X-ray crystallography. The anticancer activity of taxiresinol 1 and other two lignans 2, 3 were also studied. Taxiresinol 1 showed notable anticancer activity in the in vitro bioassays against colon, liver, ovarian and breast cancer cell lines.