The first cyclic phenolic acid glycoside dimer and new alpha-tetralone and triterpenoid glucosides from Gentiana loureirii.

Further chemical investigation of the whole plants of Gentiana loureirii led to the isolation and characterization of three new compounds, cyclic 4-O-beta-D-glucopyranosylcaffeic acid dimer (1), a new alpha-tetralone, 4-hydroxy-6-methyl-alpha-tetralone 4-O-beta-D-glucopyranoside (2), and 3beta,30-dihydroxy-12-ursen-28-oic acid 28-O-beta-D-glucopyranosyl ester (3), along with five known compounds. To the best of our knowledge, compound 1 is the first cyclic phenolic acid glycoside dimer.

Simultaneous determination of three diarylheptanoids and an alpha-tetralone derivative in the green walnut husks (Juglans regia L.) by high-performance liquid chromatography with photodiode array detector.

By optimizing extraction, separation and analytical conditions, a reliable and accurate high-performance liquid chromatographic (HPLC) method coupled with photodiode array detector (DAD) at room temperature is developed for simultaneous determination of three diarylheptanoids (juglanin A, juglanin B, rhoiptelol) and an alpha-tetralone derivative (regiolone) in methanol extracts from the green walnut husks (Juglans regia L.) The sample pretreatment process involved the reflux extraction using methanol as the extract with a ratio of liquor to sample of 15 mL/g. The separation was achieved on a SinoChrom ODS-AP C(18) column with gradient elution using acetonitrile and 2% (v/v) acetic acid in water. The intra-day and inter-day precision (RSD%) for the analytes ranged from 1.08 to 1.51 and 0.60 to 1.13, respectively. The average recoveries obtained were from 88.4% to 96.2% for the analytes with RSDs below 3.13%. The correlation coefficients of the calibration curve exceeded 0.999. The detection limits were 0.51, 0.25, 0.32 and 0.35 ng at a signal-to-noise ratio of 3, respectively. Quantitative analyses of the samples from different grown sites and in obtained different months showed that the contents of the analytes varied significantly. The method was then successfully applied for the detection and isolation of a new diarylheptanoid derivative in the green walnut husks (J. regia L.). The structure of the new compound was elucidated by various spectroscopic methods including 2D NMR techniques (COSY, HMQC, HMBC), HR-ESI-MS and X-ray single-crystal diffraction analysis.

Capillary zone electrophoresis for separation and analysis of four diarylheptanoids and an alpha-tetralone derivative in the green walnut husks (Juglans regia L.).

A fast capillary zone electrophoresis (CZE) method for the simultaneous determination of four cyclic diarylheptanoids (rhoiptelol, RH; juglanin A, JA; juglanin B, JB; juglanin C, JC) and an alpha-tetralone derivative (sclerone, SC) in the extract of the green walnut husks (Juglans regia L.) was developed. The optimized buffer was composed of 25 mM sodium tetraborate at pH 10.3. The applied voltage was 20 kV and the capillary temperature was kept constant at 20 degrees C. The detection wavelength was set at 220 nm using a photodiode array detection. The effects of several CE parameters, including pH value, buffer concentration, applied voltage and separation temperature on the separation were investigated systematically. Regression equations showed good linear relationships (correlation coefficients: 0.9996-0.9999) between the peak area of each compound (RH, JA, JB, JC and SC) and its concentration accordingly. The relative standard deviations (R.S.D.) of the migration time and peak area were less than 0.57 and 3.44% (intra-day), and 0.97 and 3.71% (inter-day), respectively. The contents of the five active compounds in the green walnut husks (J. regia L.) from different origins were determined with satisfactory repeatability and recovery.

Quantitative determination of bioactive 4-hydroxy-α-tetralone, tetralone-4-O-ß-D-glucopyranoside and ellagic acid in Ammannia baccifera (Linn.) by reversed-phase high-performance liquid chromatography.

Ammannia baccifera is an important component of various Chinese herbal formulations for which a rapid, simple, sensitive, gradient and reproducible reversed-phase high-performance liquid chromatographic method has been developed for the quantitative estimation of its bioactive constituents, 4-hydroxy-α-tetralone (4H), tetralone-4-O-ß-D-glucopyranoside (T4) and ellagic acid (EA). The chromatographic separation of samples was performed on a Chromatopak Peerless C18 (250 × 4.6 mm i.d., 5 µm) column by gradient elution with 0.1% trifluoroacetic acid in water and methanol at a flow rate of 0.6 mL/min, a column temperature at 25°C and ultraviolet detection at λ 254 nm. The limit of detection (LOD) and limit of quantification (LOQ) were 1.51 and 5.06 µg/mL for EA, 0.70 and 2.33 µg/mL for T4 and 0.22 and 0.73 µg/mL for 4H, respectively. Good results were achieved with respect to linearity (r(2) > 0.999), repeatability (relative standard deviation ≤ 1.73%) and recovery (99.06-100.76%). The method was validated for linearity, accuracy, repeatability, LOQ and LOD. The method is simple, accurate and precise and was successfully applied to the analysis of these three analytes in five different leaf and root samples of A. baccifera; the method may be recommended for routine quality control analysis of various Chinese herbal formulations containing A. baccifera.

Effects of walnut husk washing waters and their phenolic constituents on horticultural species.

INTRODUCTION: The reuse of wastewaters for agricultural purposes is a common practice in many countries and is increasingly recommended by organizations that promote sustainable development. Yet, it is restricted by the potential negative impact of these materials on soil and crops. The aim of this study was therefore to evaluate the environmental impact of walnut husk washing waters (WHWW) and their organic fractions, in order to conceive their agricultural exploitation. DISCUSSION: Phytotoxicity tests and morphological investigations on representative plant species of horticultural interest indicated that WHWW and their organic fractions can elicit a concentration-dependent stimulating effect on the growth of radish, lettuce cv. cavolo Napoli with effects up to 165 %. An opposite inhibitory effect up to 70 % was observed on spinach and lettuce cv. Gentilina. Proapoptotic effects were observed by acridine orange/ethidium bromide assay in the species inhibited by WHWW treatment. High-performance liquid chromatography-mass spectrometry analysis of the WHWW revealed the presence of a main component which was extracted selectively in organic solvents and purified by preparative chromatography. Complete spectral analysis allowed identification as 4,8-dihydroxy-1-tetralone, commonly known as regiolone. Regiolone exhibited the same concentration-dependent activity on root elongation with a stimulation in the case of radish up to 135 % with respect to control. These results open perspectives in the exploitation of WHWW and the main phenolic constituent readily available by a straightforward isolation procedure as a natural fertilizer for specific crops.

Secondary metabolites from the red mould rice of Monascus purpureus BCRC 38113.

One new tetralone, monaspurpurone (1), was isolated from the EtOH extract of a yellow mutant of the fungus Monascus purpureus BCRC 38113 (Eurotiaceae) grown on rice, along with five known compounds, ß-sitosteryl palmitate (2), ergosterol (3), ankaflavin (4), monascin (5) and p-nitrophenol (6). They were characterised on the basis of spectral analysis and comparison with literature data. All the isolates were also evaluated for the scavenging properties towards the DPPH in TLC autographic and spectroscopic assays.