gardenia-yellow and trans-sodium-crocetinate

Gardenia fruit pomace (GFP) is a byproduct during the Gardenia oil production and rich in Gardenia yellow pigment (GY) in which the major functional components are crocetin and crocetin derivatives (CDs). The application of GFP was still limited. In this research, the stabilities of CDs during thermal and lighting treatment were studied, food systems with GY or GFP were simulated to evaluate the effects of cooking methods on CDs. Seven CDs were identified and determined in GY and GFP by UPLC-QToF-MS and HPLC. The stability results showed that CDs were sensitive to heat and light, the great loss of total CDs and detachment of aglycon were observed during thermal treatment. Light-driven degradation reactions of CDs fitted the first-order model. Different cooking methods (boiling, baking, steaming) had distinct impacts on the CDs contents in the simulated food system with GY and GFP, steaming should be an appropriate method for cooking.

Topics: Carotenoids; Chromatography, High Pressure Liquid; Cooking; Fruit; Gardenia; Pigmentation; Plant Extracts; Vitamin A

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

Gardenia yellow is globally the most valuable spice and food color. It is generally a mixture of water-soluble carotenoid glycosyl esters which consist of crocetin bis(gentiobiosyl) ester as the main component. Crocetin is a natural carotenoid dicarboxylic acid that may be a candidate drug for pharmaceutical development, however, it is either present in trace amounts or is absent in natural gardenia yellow products. We here propose that crocetin produced by alkaline hydrolysis can be used to qualitatively evaluate gardenia yellow products using an ultra high performance liquid chromatographic assay. A useful and efficient isolation technique for isolating high-purity crocetin from gardenia yellow using high-speed countercurrent chromatography is described. High-speed countercurrent chromatographic fractionation followed by an ultra high performance liquid chromatographic assay showed that trans-crocetin is easily converted to about 15% cis-crocetin (85% trans-crocetin). Crocetin in gardenia yellow was quantitatively evaluated. Our approach is based on the hydrolysis process for converting crocetin glycosyl esters to crocetin before evaluation and isolation using the ultra high performance liquid chromatographic and high-speed countercurrent chromatographic methods. The combination of hydrolysis and chromatographic methods allows evaluation of the purity and quantity of crocetin in gardenia yellow.

Topics: Carotenoids; Chromatography, High Pressure Liquid; Countercurrent Distribution; Evaluation Studies as Topic; Gardenia; Hydrolysis; Molecular Structure; Plant Extracts; Sodium Hydroxide; Vitamin A

A novel crocetin glycosyl ester, neocrocin A (2), was isolated from gardenia yellow. The structure of 2 was elucidated as that of an all-trans-crocetin beta-D-gentiobiosyl beta-D-glucopyranosyl-(1-->6)-D-2-deoxy-glucopyranos-2-yl diester based on chemical and spectral data. The findings provide evidence that the binding system of crocetin glycosides is not limited to the anomeric position.

Topics: Anticarcinogenic Agents; Antioxidants; Binding Sites; Carbohydrates; Carotenoids; Gardenia; Glycosides; Magnetic Resonance Spectroscopy; Molecular Structure; Plant Extracts; Stereoisomerism; Vitamin A

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