gardenia-yellow and geniposide

In this work, a robust method for the separation of gardenia yellow and geniposide from gardenia fruit was developed based on a molecularly imprinted solid phase extraction (MISPE) procedure. First, hydrophilic molecularly imprinted microspheres (HMIMs) were prepared using gardenia yellow as the template via reversible addition fragmentation chain transfer (RAFT) precipitation polymerization. The resultant HMIMs demonstrated the multiresponsiveness to pH, temperature, and magnetism, achieving controllable uptake and release of gardenia yellow and easy recovery by external magnets. Meanwhile, the HMIMs possessed high adsorption capacity, fast binding kinetics, specific recognition, and reusability. Finally, a MISPE approach using HMIMs as adsorbent was developed for extraction of gardenia yellow and purification of geniposide after optimization of the adsorption and elution conditions. Thus, efficient separation of gardenia yellow and geniposide with relative purities of 99.77 ± 0.05% (94.04 ± 0.10% recovered) and 94.50 ± 0.62% (95.40 ± 0.86% recovered), respectively, was achieved.

Topics: Fruit; Gardenia; Iridoids; Microspheres; Plant Extracts

Herbal extracts have been extensively used worldwide for their application on memory improvement, especially among aged and memory-deficit populations. In the present study, the memory loss induced by human Abeta protein over-expression in fruitfly Alzheimer's disease (AD) model was rescued by multiple extracts from Gardenia jasminoides. Three extracts that rich with gardenia yellow, geniposide, and gardenoside components showed distinct rescue effect on memory loss. Further investigation on adding gardenoside into a formula of Ganoderma lucidum, Panax notoginseng and Panax ginseng (GPP) also support its therapeutic effects on memory improvement. Interestingly, the application of GPP and gardenoside did not alter the accumulation of Abeta proteins but suppressed the expression of immune-related genes in the brain. These results revealed the importance and relevancy of anti-inflammation process and the underlying mechanisms on rescuing memory deficits, suggesting the potential therapeutic use of the improved GPP formulation in improving cognition in defined population in the future.

Topics: Alzheimer Disease; Animals; Antimicrobial Cationic Peptides; Brain; Cognition; Disease Models, Animal; Drosophila; Drosophila Proteins; Gardenia; Gene Expression Regulation; Immunity, Innate; Iridoids; Plant Extracts; Polymerase Chain Reaction

A novel, rapid and simple analytical method was developed for the quantitative determination of crocin, crocetin and geniposide in soft drink, pastry and instant noodles. The solid samples were relatively homogenized into powders and fragments. The gardenia yellow colorants were successively extracted with methanol using ultrasound-assisted extraction. The analytes were quantitatively measured in the extracts by liquid chromatography coupled with electrospray ionization tandem mass spectrometry. High correlation coefficients (r(2)>0.995) of crocin, crocetin and geniposide were obtained within their linear ranges respectively (50-1000ng/mL, 50-1000ng/mL, 15-240ng/mL) by external standard method. The limits of detection (LODs) were 0.02μg/g for crocin, 0.01μg/g for crocetin and 0.002μg/g for geniposide. And the limits of quantitation (LOQs) were in the ranges of 0.05-0.45μg/g for crocin, and in the ranges of 0.042-0.32μg/g for crocetin, and in the ranges of 0.02-0.15μg/g for geniposide in soft drink, pastry and instant noodles samples. The average recoveries of crocin, crocetin and geniposide ranged from 81.3% to 117.6% in soft drink, pastry and instant noodles. The intra- and inter-day precisions were respectively in the range of 1.3-4.8% and 1.7-11.8% in soft drink, pastry and instant noodle. The developed methods were successfully validated and applied to the soft drink, pastry, and instant noodles collected from the located market in Beijing from China. Crocin, crocetin and geniposide were detected in the collected samples. The average concentrations ranged from 0.84 to 4.20mg/g for crocin, and from 0.62 to 3.11mg/g for crocetin, and from 0.18 to 0.79mg/g for gardenia in various food samples. The method can provide evidences for government to determine gardenia yellow pigments and geniposide in food.

Topics: Beijing; Carbonated Beverages; Carotenoids; Chromatography, High Pressure Liquid; Coloring Agents; Food Analysis; Gardenia; Iridoids; Plant Extracts; Spectrometry, Mass, Electrospray Ionization; Tandem Mass Spectrometry; Vitamin A

A novel method for the selective extraction of gardenia yellow and geniposide from Gardenia Jasminoides, based on a mechanochemical method is described. Without the need of complex separation techniques, gardenia yellow compliant with the national standard could be extracted in a simple fashion. The optimal ball-milling conditions determined were as follows: 30% g/g. active carbon milling at 200 rpm in a planetary mill for 5 min. The extraction conditions of the milled mixtures were as follows: the milled mixtures were extracted with water (liquid-solid ratio 10:1) at 20 °C for 5 min with yields 85% of total geniposide, followed by extraction with 80% ethanol solution (liquid-solid ratio 5:1) and 1% g/g. Tween 20 at 75 °C for 5 min to yield 1.45% ± 0.108% g/g of gardenia yellow. The mechanism of this selective extraction was demonstrated to follow a microstructure change of activated carbon, which occurred during milling and lead to alteration of the corresponding desorption capacities. Compared with traditional extraction methods, this novel extraction technique greatly simplifies the separation process, and proves to be advantageous in terms of low organic solvent consumption, easy operation, rapid process and high efficiency.

Topics: Biomechanical Phenomena; Chemical Phenomena; Chemistry Techniques, Analytical; Gardenia; Iridoids; Plant Extracts

Fructus gardeniae has long been used by traditional Chinese medical practitioners for its anti-inflammatory, anti-oxidant, anti-tumor and anti-hyperlipidemic characteristics. Here we describe our finding that F. gardeniae greatly reduces anti-enterovirus 71 (EV71) activity, resulting in significant decreases in EV71 virus yields, EV71 infections, and internal ribosome entry site activity. We also found that geniposide, a primary F. gardeniae component, inhibited both EV71 replication and viral IRES activity. Our data suggest the presence of a mechanism that blocks viral protein translation. According to our findings, F. gardeniae and geniposide deserve a closer look as potential chemopreventive agents against EV71 infections.

Topics: Antiviral Agents; Cell Line, Tumor; Drugs, Chinese Herbal; Enterovirus A, Human; Enterovirus Infections; Gardenia; Humans; Iridoids; Medicine, Chinese Traditional; Microbial Sensitivity Tests; Molecular Sequence Data; Protein Biosynthesis; Ribosomes; RNA, Viral; Virus Replication

In present study, the performance and separation characteristics of nine macroporous resins for the enrichment and purification of gardenia yellow from Gardenia jasminoides var. radicans Makino have been evaluated. The adsorption and desorption properties of crude gardenia yellow solution on macroporous resins including HPD722, HPD100, HPD100A, HPD400, HPD400A, D101, AB-8, XAD-16, and NKA-9 have been compared. Then, HPD722 was chosen to purify gardenia yellow because of its strong adsorption and desorption abilities as well as high selectivity. Column packed with HPD722 resin was used to perform dynamic adsorption and desorption tests to optimize the separation process of gardenia yellow. The optimal conditions were as follows: The crude gardenia yellow solution with concentration of 15 mg/mL was loaded in column packed with HPD722 resin at the flow rate of 1.0 mL/min, and the adsorbate-laden column was washed with 800 mL water, 600 mL 15% ethanol water solution respectively at the speed of 2.5 mL/min, then desorbed with 200 mL 80% ethanol water solution at the speed of 3.5 mL/min. The colority of the product obtained were up to 300. The method developed in this study provides a new approach for scale-up separation and purification of gardenia yellow from G. jasminoides var. radicans Makino.

Topics: Adsorption; Carotenoids; Chromatography, Affinity; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Ethanol; Gardenia; Iridoids; Laboratory Chemicals; Plant Extracts; Spectrophotometry, Ultraviolet; Water

Gardenia yellow powders A, B and C, containing geniposide at 0.284%, 0.938% and 2.783%, respectively, were administered orally to male and female SD rats as 3% feed admixtures for 13-weeks to evaluate any potential toxicity. Mean geniposide intake values were 5.72, 18.9 and 56.3mg/kg/day in groups receiving these feed admixtures, respectively. All animals survived the duration of the study. The following findings were evident in the gardenia yellow C group: chromatouria, slightly increased plasma total bilirubin, blackish brown discoloration of the kidneys and liver, brown pigments in the proximal tubular epithelium of the kidneys. Slightly increased plasma total bilirubin was considered to be due to interference of metabolite of geniposide with the system of measurement and not to be a toxic effect since there were no related changes in histopathology of the liver or in any blood chemistry parameters. Other findings were limited to pigmentations or discolorations attributable to metabolites of geniposide. No treatment-related effects were evident on body weight, food consumption, ophthalmology, hematology or organ weights in any group. Therefore, it was concluded that 3-month ingestion of the gardenia yellow powder containing geniposide at 2.783% (approximately 60 mg/kg/day as geniposide intake) does not cause any severe toxic effects.

Topics: Administration, Oral; Animals; Blood Chemical Analysis; Body Weight; Eating; Female; Food Coloring Agents; Gardenia; Histocytochemistry; Iridoids; Male; Plant Extracts; Pyrans; Rats; Rats, Sprague-Dawley; Statistics, Nonparametric; Survival Analysis

Gardenia fruit (Gardenia jasminoides ELLIS) is widely used as a natural food colorant and as a traditional Chinese medicine for treatment of hepatic and inflammatory diseases. "Gardenia yellow" is a natural food colorant which is extracted by ethanol from gardenia fruit. The purpose of this study was to evaluate the genotoxicity of gardenia yellow. Genotoxicity of gardenia yellow and its components, crocetin, gentiobiose (a component of crocin), geniposide and genipin (formed by hydrolysis of geniposide), was studied by Ames test, rec-assay, and sister chromatid exchange (SCE) using V79 cells. Gardenia yellow and its components were found not to be mutagenic in the Salmonella reverse mutation assay. Gardenia yellow and genipin caused damage of DNA in rec-assay. Gardenia yellow induced a significant dose-dependent increase of SCE frequency (8.6 times at 1000 microg/ml as the value for the solvent control). Only genipin induced SCEs significantly among the components of gardenia yellow. Moreover, genipin induced a significant increase of tetraploids at all doses tested (95% at 8 microg/ml). Gardenia yellow preparation was analyzed by capillary electrophoresis (CE), and geniposide was detected. However, genipin was not observed. In conclusion, we have shown that genipin possesses genotoxicity. Furthermore, there were unidentified genotoxicants in gardenia yellow.

Topics: Bacillus subtilis; Carotenoids; Coloring Agents; Disaccharides; DNA Damage; Electrophoresis, Capillary; Food Coloring Agents; Gardenia; Iridoid Glycosides; Iridoids; Mutagenicity Tests; Plant Extracts; Pyrans; Sister Chromatid Exchange; Vitamin A

Acute toxicity by gardenia yellow color was studied in rats. Oral administration of the colorant at doses of 800 mg/kg up to 5000 mg/kg caused diarrhea and increases in serum alanine aminotransferase and aspartate aminotransferase activities in a dose-dependent manner. After 24 h of oral treatment with 2000 mg/kg of the colorant, liver showed partially hemorrhagic changes and the intestinal tract, especially the duodenum, appeared blue. The toxicity induced by the colorant was stronger by oral administration than by intraperitoneal administration. The content of geniposide, an iridoid compound, was estimated to be 28% of the colorant, and this iridoid accounted for almost all the hepatotoxic activity of the colorant.

Topics: Administration, Oral; Alanine Transaminase; Animals; Aspartate Aminotransferases; Coloring Agents; Diarrhea; Gardenia; Injections, Intraperitoneal; Iridoids; Liver; Male; Plant Extracts; Pyrans; Rats; Rats, Inbred Strains