Synthesis of methyl epijasmonate and cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one

A novel and efficient synthesis of both (±)-methyl epijasmonate and (±)-cis-3-(2-oxopropyl)-2-(pent-2Z-enyl)-cyclopentan-1-one is described. The key step to establish the cis-stereochemistry on the 5-membered ring is an ionic Diels–Alder reaction, which is high yielding and highly regioselective. Subsequent key steps include oxidative cleavage of the six-membered ring, Wittig coupling and for the synthesis of epijasmonate, the haloform reaction.     

Ultrasound-Assisted Extraction of Carotenoids from Carrot Pomace and Their Optimization through Response Surface Methodology

Ultrasound-assisted extraction (UAE) was used to extract carotenoids from the carrot pomace. To investigate the effect of independent variables on the UAE, the response surface methodology (RSM) with central-composite design (CCD) was employed. The study was conducted with three independent variables including extraction time (min), temperature (°C), and ethanol concentration (%). The results showed that the optimal conditions for UAE were achieved with an extraction time of 17 min, temperature of 32 °C, and ethanol concentration of 51% of total carotenoids (31.82 ± 0.55); extraction time of 16 min, temperature of 29 °C, and ethanol concentration of 59% for a combination of β-carotene (14.89 ± 0.40), lutein (5.77 ± 0.19), and lycopene (2.65 ± 0.12). The non-significant (p > 0.05) correlation under optimal extraction conditions between predicted and experimental values suggested that UAE is the more productive process than conventional techniques for the extraction of carotenoids from the carrot pomace.     

Investigations on Anticancer Potentials by DNA Binding and Cytotoxicity Studies for Newly Synthesized and Characterized Imidazolidine and Thiazolidine-Based Isatin Derivatives

Imidazolidine and thiazolidine-based isatin derivatives (IST-01–04) were synthesized, characterized, and tested for their interactions with ds-DNA. Theoretical and experimental findings showed good compatibility and indicated compound–DNA binding by mixed mode of interactions. The evaluated binding parameters, i.e., binding constant (K_b), free energy change (ΔG), and binding site sizes (n), inferred comparatively greater and more spontaneous binding interactions of IST-02 and then IST-04 with the DNA, among all compounds tested under physiological pH and temperature (7.4, 37 °C). The cytotoxic activity of all compounds was assessed against HeLa (cervical carcinoma), MCF-7 (breast carcinoma), and HuH-7 (liver carcinoma), as well as normal HEK-293 (human embryonic kidney) cell lines. Among all compounds, IST-02 and 04 were found to be cytotoxic against HuH-7 cell lines with percentage cell toxicity of 75% and 66%, respectively, at 500 ng/µL dosage. Moreover, HEK-293 cells exhibit tolerance to the increasing drug concentration, suggesting these two compounds are less cytotoxic against normal cell lines compared to cancer cell lines. Hence, both DNA binding and cytotoxicity studies proved imidazolidine (IST-02) and thiazolidine (IST-04)-based isatin derivatives as potent anticancer drug candidates among which imidazolidine (IST-02) is comparatively the more promising.     

Kinetics of catalytic oxidation of aqueous sodium sulfite

A gas-lift bubble column was used to investigate the kinetics of the reaction between oxygen and aqueous solutions of sodium sulfite in the presence of cobalt sulfate catalyst. Reaction orders have been determined for the sulfite, catalyst, and oxygen under high and low oxygen partial-pressure conditions. Parts of this paper were presented at the Second International Conference on Chemistry in Industry, Saudi     

Herbicidal activity of flavonoids of mango leaves against Parthenium hysterophorus L

This study was undertaken to investigate the herbicidal activity of mango (Mangifera indica L.) leaves against parthenium weed (Parthenium hysterophorus L.). The aqueous leaf extract at 15% concentration (on fresh weight basis) significantly reduced germination, shoot length and the shoot and root biomasses of parthenium seedlings. In a leaf residue incorporation pot trial, 2% residue incorporation treatment significantly suppressed the root and shoot biomasses of parthenium, while a 5% residue treatment completely stopped the growth of the weed. Five flavonoids, namely (-)-epicatechin-3-O-β-glucopyranoside (1), 5-hydroxy-3-(4-hydroxyphenyl)pyrano[3,2-g]chromene-4(8H)-one (2), 6-(p-hydroxybenzyl)taxifolin-7-O-β-D-glucoside (tricuspid) (3), quercetin-3-O-α-glucopyranosyl-(1 → 2)-β-D-glucopyranoside (4) and (-)-epicatechin(2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H chromene-3,5,7-triol (5) were isolated from mango leaves. In a laboratory bioassay, 50 ppm solution of compounds 3 and 4 caused yellowing of the parthenium seedlings. A 250 ppm solution of compound 4 also significantly reduced germination and the root and shoot lengths of parthenium seedlings. This study concludes that compound 4 exhibits herbicidal activity against parthenium weed.     

Antifungal activity of flavonoids isolated from mango (Mangifera indica L.) leaves

Five flavonoids, namely (-)-epicatechin-3-O-β-glucopyranoside (1), 5-hydroxy-3-(4-hydroxylphenyl)pyrano[3,2-g]chromene-4(8H)-one (2), 6-(p-hydroxybenzyl)taxifolin-7-O-β-D-glucoside (tricuspid) (3), quercetin-3-O-α-glucopyranosyl-(1 → 2)-β-D-glucopyranoside (4) and (-)-epicatechin(2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol (5), were isolated from the leaves of mango (Mangifera indica L.). Antifungal activity of these compounds was evaluated against five fungal species, namely Alternaria alternata (Fr.) Keissler, Aspergillus fumigatus Fresenius, Aspergillus niger van Tieghem, Macrophomina phaseolina (Tassi) Goid. and Penicillium citrii. Six concentrations, namely 100, 300, 500, 700, 900 and 1000 ppm of each of the five flavonoids were employed by means of the poisoned medium technique. All concentrations of the five test flavonoids significantly suppressed fungal growth. However, the specificity of different test compounds was evident against different fungal species. In general, antifungal activity of the flavonoids was gradually increased by increasing their concentrations. The highest concentration (of 1000 ppm) of compounds 1-5 reduced the growth of different target fungal species by 63-97%, 56-96%, 76-99%, 76-98% and 82-96%, respectively.     

Bioassays guided fractionation of Coronopus didymus for its antifungal activity against Sclerotium rolfsii

Sclerotium rolfsii Sacc. is a pathogen of about 500 plant species. In a laboratory screening bioassay, methanolic extracts of 15?mg?mL?1 concentrations of different parts of Coronopus didymus (L.) Sm. (Brassicaceae) namely leaf, stem, inflorescence and root reduced the biomass of S. rolfsii by 67%, 26%, 40% and 58%, respectively. Methanolic root extract was successively fractionated with n-hexane, chloroform, ethyl acetate and n-butanol. All the concentrations (3.125-200?mg?mL?1) of ethyl acetate fraction completely inhibited the target fungal growth. Two compounds A and B were separated from this fraction by Thin Layer Chromatography (TLC). TLC fraction A was found highly effective against S. rolfsii with MIC value 15.62?μg?mL?1 as compared to MIC value 7.81?μg?mL?1 of the commercial fungicide mencozeb. This compound may be used for the synthesis of natural product based fungicide for the control of S. rolfsii.