iridoids and trans-sodium-crocetinate

Discovering novel compounds with higher activities is a key aim of natural products research. Gardenia jasminoides Ellis is a herb with anti-inflammatory properties. Iridoid glycosides (mainly geniposide) and crocetin derivatives (crocins) are the two major active constituents in this herb and are considered its active ingredients. However, which components are responsible for the anti-inflammatory properties of gardenia have remained to be investigated.. Here, we prepared total iridoid glycocides (TIG) and total crocins (TC) from G. jasminoides Ellis, determined their main chemical constituents, and performed animal studies to evaluate their anti-adjuvant arthritis activities, thus, proposing a reasonable mechenism to explain the anti-inflammatory activities of the active components in this herbal remedy.. TIG and TC were prepared by using HPD-100 macroporous resin, and characterized by UHPLC-DAD-MS and UV-Vis spectrophotometer. Then, freund's complete adjuvant-injected rats underwent drug treatments with TIG (160 mg/kg) and TC (160 mg/kg) for 14 days, and their ankle diameters were measured. Moreover, X-ray radiographs of the adjuvant injected hind paws were evaluated. Finally, histopathological examinations of the ankle joints, spleens and thymus were carried out to evaluate inflammatory reactions, and immunohistochemical measurements were conducted to evaluate TNF-α and TGF-β1 expression in the ankle joint of the rats.. The chemical composition determination of the current study showed that TIG was mainly composed of geniposide and TC was a fraction predominantly with crocin-1, crocin-2 and crocin-3. Calculation of results showed that TIG and TC contained 58.2% total iridoid glycosides and 54.7% total crocins, respectively. Our study suggested TIG and TC treatments markedly decreased paw swelling and ankle diameters of AA rats (both p < 0.05). The radiological analysis showed that administration of TIG and TC ameliorated bone destruction, and reduced the radiological bone destruction scores (TIG p < 0.05, TC p>0.05). Moreover, data from histological assessment demonstrated considerable mitigation of inflammation in the joints (both p < 0.01), spleen and thymus of AA rats treated with TIG and TC. TNF-α and TGF-β1 protein expression according to immunohistochemistry staining also supported the anti-arthritis activities of TIG and TC (TNF-α: TIG p < 0.01 and TC p < 0.05, TGF-β1: TIG p < 0.01 and TC p>0.05).. In the current study, fractionation of gardenia prior to further in vivo investigation has for the first time provided reasonable explanation for the anti-inflammatory activity of this herbal remedy. Our study showed that both TIG and TC from gardenia have anti-inflammatory properties. Overall, these experimental findings suggest that gardenia could be regarded as a potential therapeutic target for arthritis. However, as geniposide has a higher content than crocins in this herbal drug, TIG (mainly geniposide) seems to be primarily responsible for the anti-inflammatory properties of gardenia. Taken together, this maiden attempt demonstrated that TIG (mainly geniposide) is more important in evaluating the anti-inflammatory activity of G. jasminoides Ellis.

Topics: Animals; Anti-Inflammatory Agents, Non-Steroidal; Arthritis, Experimental; Carotenoids; Chromatography, High Pressure Liquid; Drug Evaluation, Preclinical; Freund's Adjuvant; Gardenia; Iridoid Glycosides; Iridoids; Male; Rats, Sprague-Dawley; Transforming Growth Factor beta1; Tumor Necrosis Factor-alpha; Vitamin A

To investigate the effect of different initial processing methods on the quality of Gardenia and determine the best cooking time in gardenia processing through the determination of index components content. The contents of geniposide, crocetin Ⅰ and total iridoid glycosides in Gardenia were determined before storage, six months after storage and one year after storage. During storage, the contents of geniposide, crocetin Ⅰ and total iridoid glycosides in directly dried Gardenia were 1.68%, 0.45% and 6.45% respectively. The contents of geniposide, crocetin Ⅰ and total iridoid glycosides in Gardenia with different steaming time were 1.34%-0.5%, 0.28%-0.06% and 6.09%-1.59% respectively. The contents of geniposide, crocetin Ⅰ and total iridoid glycosides in Gardenia with different boiling time (adding alum)were 1.42%-0.41%, 0.35%-0.07% and 6.40%-1.65% respectively. The direct drying of Gardenia samples could not achieve the function of killing enzyme and protecting glycosides. The enzymes from degradation of the index components were basically destroyed after steaming time of 13 min or boiling (adding alum) time of 8 min, achieving the function of killing enzyme and protecting glycosides.

Topics: Carotenoids; Chemistry, Pharmaceutical; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Gardenia; Iridoid Glycosides; Iridoids; Phytochemicals; 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

To compare the contents of the main chemical compositions in Gardenia jasminoids before and after being roasted with ginger juice.. Four diterpenoid pigments constituents (C-1, C-2, C-3, crocetin) were determined simultaneously by UPLC on an Agilent Poroshell 120 EC-C18 column at 35 degrees C with the methanol-0.5% formic acid anhydrous in gradient elution as the mobile phrase. The detection wavelength was set at 440 nm and the flow rate was 0.4 mL x min(-1). Two iridoids constituents (G-1, G-2) were determined simultaneously by HPLC on an Agilent TC-C18(2) column at 35 degrees C with acetonitrile-0.5% formic acid anhydrous (18:82) as the mobile phrase. The detection wavelength was set at 238 nm and the flow rate was 1.0 mL x min(-1).. After being processed with ginger juice, the contents of the diterpenoid pigments constituents decreased slightly and the contents of the iridoids constituents increased slightly.. The contents of the main chemical compositions in G. jasminoids roasted with ginger juice increased slightly with some regularity, but there were no significant differences.

Topics: Carotenoids; Chemistry, Pharmaceutical; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Gardenia; Iridoids; Pharmacology; Vitamin A; Zingiber officinale

To develop a HPLC- ELSD method for determination the contents of geniposide, crocin and crocetin in different processing products of Fructus Gardeniae.. The separation was performed in the HyperClone ODS C18 column (250 mm x 4. 6 mm, 5 microm) with linear gradient elution using methanol-water and 0.05% phosphoric acid in water, the flowing rate was 0.8 mL/min, the column temperature was 30 degrees C, and the ELSD parameter was as follow: 70 degrees C as atomization temperature and 2.0 L/min as the gas flowing rate.. The contents of geniposide and crocin in raw, yellowish, carbocoal and scorched Fructus Gardeniae decreased with the deepening of processing degree. However, the content of crocetin in carbocoal and scorched Fructus Gardeniae increased comparing with the raw one.. This is a simple and credible quality control method, and can be used for the quality control and comprehensive evaluation for different processed products of Fructus Gardeniae.

Topics: Carotenoids; Chromatography, High Pressure Liquid; Drugs, Chinese Herbal; Fruit; Gardenia; Iridoids; Quality Control; Reproducibility of Results; Technology, Pharmaceutical; Vitamin A

Crocetin esters present in saffron (Crocus sativus L.) stigmas and in Gardenia jasminoides Ellis fruit are the compounds responsible for their color. Of the fifteen crocetin esters identified in this study, five new compounds were tentatively identified: trans and cis isomers of crocetin (beta-D-triglucoside)-(beta-D-gentibiosyl) ester, trans and cis isomers of crocetin (beta-D-neapolitanose)-(beta-D-glucosyl) ester, and cis crocetin (beta-D-neapolitanose)-(beta-D-gentibiosyl) ester. The most relevant differences between both species were a low content of the trans crocetin (beta-D-glucosyl)-(beta-D-gentibiosyl) ester, the absence of trans crocetin di-(beta-D-glucosyl) ester in gardenia, and its higher content of trans crocetin (beta-D-gentibiosyl) ester and cis crocetin di-(beta-D-gentibiosyl) ester. With the same chromatographic method it was possible to identify, in a single run, ten glycosidic compounds in saffron extracts with a UV/vis pattern similar to that of picrocrocin; among them, 5-hydroxy-7,7-dimethyl-4,5,6,7-tetrahydro-3H-isobenzofuranone 5-O-beta-D-gentibioside and 4-hydroxymethyl-3,5,5-trimethyl-cyclohexen-2-one 4-O-beta-D-gentibioside were tentatively identified for the first time in saffron. Of these ten glycosides, only the O-beta-D-gentibiosyl ester of 2-methyl-6-oxo-2,4-hepta-2,4-dienoic acid was found in gardenia samples, but it was possible to identify the iridoid glycoside, geniposide.

Topics: Carotenoids; Chromatography, Liquid; Crocus; Cyclohexenes; Esters; Flowers; Fruit; Gardenia; Glucosides; Glycosides; Iridoids; Pyrans; Spectrometry, Mass, Electrospray Ionization; Terpenes; 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