Crocin and geniposide profiles and radical scavenging activity of gardenia fruits (Gardenia jasminoides Ellis) from different cultivars and at the various stages of maturation
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Gardenia jasminoides
Gardenia
Crocetin
Gardenia jasminoides
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Crocetin
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From the fruits of Gardenia jasminoides several carotenoids were isolated and identified. Crocetin (1) was characterized by UV/vis, cochromatography, and LC-MS. The following glycosyl esters of crocetin (1) were identified: crocin (crocetin di(β-gentiobiosyl) ester) (6) by UV/vis, 1H- and 13C-NMR, and FAB-MS and crocetin mono(β-gentiobiosyl) ester (4) by UV/vis, 1H-NMR, and LC-MS. There are strong indications for the presence of 13Z-crocin (9) (UV/vis, 1H-NMR, and LC-MS). From saffron (Crocus sativus L.), another glycosyl ester of crocetin (1) was isolated. It was identified as crocetin (β-gentiobiosyl) (β-neapolitanosyl) ester (7) by UV/vis, 1H-NMR, and MS. Keywords: Carotenoids; glycosyl esters; isolation; structure elucidation; Gardenia jasminoides; saffron; Crocus sativus
Crocetin
Gardenia jasminoides
Crocus
Gardenia
Iridaceae
Glucoside
Proton NMR
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Analysis of gardenia yellow in food products has been carried out by the detection of crocin and/or geniposide as indicator compounds. However, neither indicator compound was present in a few food products. As a new analytical strategy for gardenia yellow, we adopted crocetin, which is produced from colored components of gardenia yellow by alkaline hydrolysis, as an indicator compound. Crude extracts from food products were hydrolyzed in 0.1N NaOH for 30min at 50°C and the resultant hydrolyzates were analyzed by HPLC. Recoveries from jelly, candy and rice crackers through the whole analytical procedure were 85.6, 86.0 and 80.5%, respectively. When 20 food products labeled as containing gardenia yellow were analyzed, 11 of them had different chromatographic patterns from an authentic preparation and crocin was not detected at all in 5 samples. However, crocetin was found in every food product after alkaline hydrolysis, in the range of 0.1-13.4μg/g (as crocetin). Geniposide was found in only 3 food products.
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Gardenia jasminoides
Alkaline hydrolysis
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Crocina water soluble carotenoidis found in the fruits of gardenia (Gardenia jasminoides Ellis) and in the stigmas of saffron (Crocus sativus Linne). For crocin purification, gardenia fruits are extracted with 50% acetone, followed by ether washing, ion exchange, and separation by preparative HPLC. Purified crocin with purity of >99.6% has an antioxidative activity at concentrations up to 40 ppm. At 20 ppm the antioxidative activity of crocin is comparable to that of BHA. The antioxidant property of crocin as evaluated by the thiocyanate method was better than with the thiobarbituric acid method. The adduct between the linoleic acid radical and crocin was detected by LC-MS. When crocin reacted with oxygen in the presence of FeSO4, intermediates such as monohydroperoxides and dihydroperoxides of crocin were formed and detected by LC-MS. Keywords: Carotenoids; crocetin derivatives; antioxidant; thiocyanate method; TBA method; HPLC; MS
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Objective To study the chemical constituents in Gardenia jasminoides. Method The constituents were isolated by column chromatography on silica gel and ODS, and identified by NMR, MS spectroscopic methods. Result Nine compounds, imperatorin (1), isoimperatorin (2), crocetin (3), 5-hydroxy-7, 3', 4', 5'-tetrainethoxyflavone (4), 2-methyl-3, 5-dihydroxychromone (5), sudan III (6), geniposide (7), crocin (8), crocin-3 (9) were isolated and identified. Conclusion Compounds 1-6 were isolated from this plant for the first time.
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Crocetin
Gardenia
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To establish a method of quantitative analysis of multi-components, by single marker(QAMS)for simultaneously determining six ingredients in Gardenia jasminoides fruits.A multi-wavelength segmentation detection method was used. A methodological mode was found to analysis six ingredients in Gardenia jasminoides fruits by quantitative analysis of QAMS. Taken geniposide as reference to create RCF with gardenia acid, chlorogenic acid, crocin I, crocin II and crocin III.The good reproducibility and acceptable durability of method was validated between two HPLC systems and three columns. 20 batches of Gardenia jaminoides fruits was analysis, and the results showed good linear correlation compared to external standard method (r > 0. 999).QAMS can be used as quality evaluation method of multi-component Gardenia jaminoides fruits.
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Gardenia
Chlorogenic Acid
Quantitative Analysis
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For many centuries, Gardenia (Gardenia jasminoides Ellis) was highly valued as a food homologous Chinese herbal medicine with various bioactive compounds, including crocin I and geniposide. However, the functional mechanism underlying the hypoglycemic effect of gardenia is absent in the literature. To evaluate the effect of gardenia and its different extracts on type 2 diabetes mellitus (T2DM) in in vivo and in vitro experiments, the dried gardenia powder was extracted using 60% ethanol and eluted at different ethanol concentrations to obtain the corresponding purified fragments. After that, the active chemical compositions of the different purified gardenia fragments were analyzed using HPLC. Then, the hypoglycemic effects of the different purified gardenia fragments were compared using in vitro and in vivo experiments. Finally, the different extracts were characterized using UPLC-ESI-QTOF-MS/MS and the mass spectrometric fragmentation pathway of the two main compounds, geniposide and crocin I, were identified. The experimental results indicated that the inhibitory effect of the 40% EGJ (crocin I) on the α-glucosidase was better than the 20% EGJ (geniposide) in vitro. However, the inhibitory effect of geniposide on T2DM was better than crocin I in the animal experiments. The different results in vivo and in vitro presumed potentially different mechanisms between crocin I and geniposide on T2DM. This research demonstrated that the mechanism of hypoglycemia in vivo from geniposide is not only one target of the α-glucosidase but provides the experimental background for crocin I and the geniposide deep processing and utilization.
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Gardenia fruit (fruit of Gardenia jasminoides Ellis) is used as a natural pigment resource and a Chinese traditional medicine. The white mesocarp turning orange or red that occurs during gardenia fruit maturation arises from the production and accumulation of the apocarotenoids, especially crocin-1, which is derived from carotenoid. Meanwhile, the major medical component geniposide is accumulated in gardenia fruit. To further our understanding of the synthetic and accumulation mechanism for crocin-1 and geniposide in gardenia fruit, the contents of crocin-1 and geniposide and the transcripts of phytoene synthase (GjPSY) profiles in gardenia fruits were examined at various stages of maturation. The concentration of crocin-1 and geniposide in gardenia fruit was determined by reversed-phase high-performance liquid chromatography (HPLC). The results showed that the concentration of crocetin-1 was increased during fruit development and the concentration of geniposide does not change significantly during maturing. The expression levels of GjPSY mRNA were examined by RT-PCR. It was revealed that GjPSY was constitutively expressed during fruit development, suggesting that the primary mechanism that controls crocin accumulation in G. jasminoides fruits during development is not correlated to the differential regulation of transcript levels of GjPSY gene.
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Crocin( Crocetin di-gentiobiose ester ) is the chemical constituent isolated from the Saffron, the dried trifid stigmaof the plant Crocus sativus L. and also from the fruits of Gardenia( Gardenia jasminoides Ellis ) It is found to be effective as anti- proliferative, anti-oxidant, learning and memory enhancer, brain neurodegenerative disorder, sperm cryoconservation, biosurfactant,alzheimer disorder .It has earned a universal acceptability as a phyotherapeutical drug because of its history of safe and zero sideeffects. This communication deals with the phytochemistry and applications of crocin in nutritional and therapeutic purposesandsignificance in the real worldin all aspects.
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Gardenia jasminoides
Gardenia
Safranal
Phytochemistry
Crocus
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Gardenia,dried from the ripe fruit of the Rubiaceous plant Gardenia Jasminoides Ellis,could be used widely.Crocin belong to natural pigments extracted from the gardenia fruit.Many studies found that crocin have a variety of pharmacology activities,such as neuro-protected effect,anti-tumor and so on.In recent years,lots of studies on pharmacology of crocin have been reported.This article summarizes the research progress of crocin on pharmacology and pharmacokinetics,in order to provide the basis for the development and clinical application of crocin.
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