- Physical stability of the blue pigments formed from geniposide of gardenia fruits: Effects of ph, temperature, and light
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Fruits of Gardenia jasminoides contain geniposide which can be transformed to blue pigments by a simple modification. Colorless geniposide obtained from gardenia, fruits by charcoal and silica gel column chromatographies was hydrolyzed with β-glucosidase to yield genipin. The resulting genipin was transformed to blue pigments by reaction with amino acids (glycine, lysine, or phenylalanine). The stability of the blue pigments against heat, light, and pH was studied to examine the blue dye for possible use as' a value-added food colorant. Thermal degradation reactions at temperatures of 60-90 °C were carried out at different pH levels within the range 5.0-9.0 (pH 5.0, acetate buffer; pH 7.0, phosphate buffer; and pH 9.0, CHES buffer). The blue pigments remained Stable after 10 h at temperatures of 60-90 °c, and in some cases, more new pigments formed. The pigments were more stable at alkaline pH than neutral and acidic pH. Similarly, the pigments were stable under light irradiance of 5000-20 000 lux. In this case, pH effect was not significant.
- Paik, Young-Sook,Lee, Chang-Min,Cho, Man-Ho,Hahn, Tae-Ryong
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- Iridoid glycosides from Gardeniae Fructus for treatment of ankle sprain
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The iridoid glycosides, genipin 1-O-β-d-isomaltoside (1) and genipin 1,10-di-O-β-d-glucopyranoside (2), together with six known iridoid glycosides, genipin 1-O-β-d-gentiobioside (3), geniposide (4), scandoside methyl ester (5), deacetylasperulosidic acid
- Chen, Quan Cheng,Zhang, Wei Yun,Youn, UiJoung,Kim, HongJin,Lee, IkSoo,Jung, Hyun-Ju,Na, MinKyun,Min, Byung-Sun,Bae, KiHwan
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- IRIDOIDS OF GARRYA ELLIPTICA AS PLANT GROWTH INHIBITORS
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Extracts from catkins of Garrya elliptica inhibit the growth of wheat embryos.The components responsible for this activity have been identified as the iridoids geniposide and geniposidic acid together with their aglucones.Key Word Index - Garrya elliptica; Garryaceae; iridoids; aglucones; genipin; geniposide; geniposide acid; plant growth inhibitors.
- Cameron, Donald W.,Feutrill, Geoffrey I.,Perlmutter, Patrick,Sasse, Jenneth M.
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- Two new iridoid glycosides from Gardeniae Fructus
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Two new iridoid glycosides, genipin 1,10-di-O-α-L-rhamnoside (1) and genipin 1,10-di-O-β-D-xylopyranoside (2), along with thirteen known compounds (3–15) were isolated from Gardeniae Fructus. Their structures were elucidated by physical data analyses such as NMR, UV, IR, HR-ESI-MS, as well as chemical hydrolysis. All compounds were tested for their tyrosinase inhibitory and antioxidant activities. At a concentration of 25 μM, compound 13 showed obvious mushroom tyrosinase inhibition activity with % inhibition value of 36.52 ± 1.98%, with kojic acid used as the positive control (46.09 ± 1.29%). At a concentration of 1 mM, compounds 8 and 9 exhibited considerable DPPH radical scavenging activities, with radical scavenging rates of 48.54 ± 0.47%, 58.59 ± 0.39%, respectively, with L-ascorbic acid used as the positive control (59.02 ± 0.77%).
- Shu, Penghua,Yu, Mengzhu,Zhu, Huiqing,Luo, Yuehui,Li, Yamin,Li, Nianci,Zhang, Hui,Zhang, Jialong,Liu, Guangwei,Wei, Xialan,Yi, Wenhan
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- An acid-stable β-glucosidase from Aspergillus aculeatus: Gene expression, biochemical characterization and molecular dynamics simulation
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β-Glucosidases hydrolyze terminal, non-reducing β-D-glucosyl residues and thereby release β-D-glucose. They have applications in the production of biofuels, beverages and pharmaceuticals. In this study, a β-glucosidase derived from Aspergillus aculeatus (BGLA) was expressed, characterized, and the molecular mechanism of its acid denaturation was comprehensively probed. BGLA exhibited maximal activity at pH 5.0–6.0. Its optimal temperature was 70 °C. Its enzyme activity was enhanced by Mg2+, Ca2+ and Ba2+, while Cu2+, Mn2+, Zn2+, Fe2+ and Fe3+ had a negative effect. BGLA showed activity on a broad range of substrates including salicin, cellobiose, arbutin, geniposide and polydatin. Finally, the acid-denaturation mechanism of BGLA was probed using molecular dynamics (MD) simulations. The results of simulation at pH 2.0 imply that the contact number, solvent accessible surface area and number of hydrogen bonds in BGLA decreased greatly. Moreover, the distance between the residues Asp280 and Glu509 that are part of the active site increased, which eventually destroyed the enzyme's catalytic activity. These MD results explain the molecular mechanism of acid denaturation of BGLA, which will greatly benefit the rational design of more acid-stable β-glucosidase variants in the future.
- Li, Yu,Hu, Xiaoyan,Sang, Jingcheng,Zhang, Ying,Zhang, Huitu,Lu, Fuping,Liu, Fufeng
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p. 462 - 469
(2018/08/03)
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- A PROCESS FOR PRODUCING GARDENIA BLUE PIGMENT FORM GENIPOSIDE
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A process for producing the gardenia blue pigment comprising treating geniposide with a glycosidase to obtain a hydrolysate, extracting the hydrolysate with a solvent and removing the solvent after the extraction to obtain a product comprising genipin, reacting the product comprising genipin with an amino acid and/or a salt thereof under an atmosphere of inert gas, and introducing oxygen after genipin is consumed to produce the gardenia blue pigment. The process is easy-to-workup and suitable for industry and the obtained gardenia blue pigment is bright and suitable for industrial application.
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Page/Page column 6
(2018/03/06)
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- BICYCLIC COMPOUND AND PHARMACEUTICAL COMPOSITION THEREOF FOR TREATING STROKE AND USE THEREOF
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The present disclosure relates to a bicyclic compound, a pharmaceutical composition thereof, and its novel use. More particularly, the present disclosure relates to the bicyclic compound according to Formula I or Formula II, the pharmaceutical composition for treating a stroke, and the use of the bicyclic compound treating the stroke.
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Paragraph 0095; 0096; 0097; 0098
(2017/11/06)
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- Enhancement of active compound, genipin, from Gardeniae Fructus using immobilized glycosyl hydrolase family 3 β-glucosidase from Lactobacillus antri
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Geniposide is an iridoid glycoside, which is abundant in Gardeniae Fructus. Despite the various pharmaceutical effects of geniposide on a human body, its hydrolysis into a smaller molecule, genipin, by β-glucosidase produced by bacteria in the intestines is particularly important to improve geniposide uptake into the body. Since geniposide is much more abundant in Gardeniae Fructus than its aglycone genipin, we herein transformed geniposide into genipin using purified recombinant β-glucosidase from Lactobacillus antri (rBGLa), which was expressed in Escherichia coli to enhance the genipin content. Purified rBGLa was characterized using p-nitrophenyl β-d-glucopyranoside, and the optimal temperature and pH for its β-glucosidase activity were found to be 45?°C and 6.0. When the enzyme was immobilized, rBGLa was active at higher temperatures than the free enzyme, and we confirmed that its stability upon changes in pH and temperature was highly improved. Using 0.5?μg/mL free rBGLa, single compound of 0.4?mM geniposide was efficiently converted into genipin within 2?h, and the immobilized rBGLa also successfully transformed geniposide in a hot-water extract of Gardeniae Fructus into the aglycone, which makes it applicable to the food and pharmaceutical industries.
- Kim, Young Soo,Lee, Chung-Jo,Ma, Jin Yeul
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- A NEW PROCESS FOR PRODUCING GARDENIA BLUE PIGMENT
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A process for producing the gardenia blue pigment is provided. The process is easy to operate and suitable for industry and the obtained gardenia blue pigment is bright and suitable for industrial application.
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Paragraph 0035
(2017/09/23)
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- NEW GARDENIA BLUE PIGMENT, PREPARATION AND USE THEREOF
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A gardenia blue pigment is derived from a reaction of genipin with an amino acid. It is brighter than commercial gardenia blue pigment and suitable for industrial application. A process for producing the gardenia blue pigment and the use thereof in food and beverage industries are also provided.
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Page/Page column 9
(2017/10/13)
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- Preparation of a genipin blue from egg protein and genipin
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Genipin blue is a pigment prepared from the reaction of genipin with amino acid. We describe herein a new method used to prepare genipin blue, watersoluble blue pigments, through the reaction of hen egg protein with genipin. The effects of reaction time, reaction temperature, the pH value of the solution and the mass ratio of the reactants on the preparation are studied. One part of genipin reacted with eight parts of hen egg protein (w/w) in water (pH value of reaction system 7.5) at 60°C for 96 h and gave blue pigments with the maximum colour value of 146.2. The blue pigments showed identical absorption activity in UV spectroscopy (λmax=584 nm) to that of gardenia blue pigments, which were prepared from the reaction of genipin with amino acid.
- Yang, Dan,Zhou, Min,Wei, Wanxing,Zhu, Honglin,Fan, Xiwang
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scheme or table
p. 765 - 769
(2012/10/18)
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- Transformation of geniposide into genipin by immobilized β-glucosidase in a two-phase aqueous-organic system
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Genipin is the bioactive compound of geniposide and a natural cross-linking agent. In order to improve the preparation process of genipin, the hydrolysis of geniposide to genipin by immobilized β-glucosidase in an aqueous-organic two-phase system was studied. β-Glucosidase was immobilized by the crosslinking-embedding method using sodium alginate as the carrier. The optimum reaction temperature, pH value and time were 55 °C, 4.5 and 2.5 h, respectively. To reduce genipin hydrolysis and byproduct production the reaction was carried out in an aqueous-organic two-phase system comprising ethyl acetate and sodium acetate buffer. The product was analyzed by HPLC, UV, IR, and NMR. The yield of genipin was 47.81% and its purity was over 98% (HPLC).
- Yang, Yi-Shun,Zhang, Tong,Yu, Shai-Cheng,Ding, Yue,Zhang, Li-Ying,Qiu, Chen,Jin, Duo
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experimental part
p. 4295 - 4304
(2011/07/30)
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- Enzymatic Synthesis of Novel Phosphatidylgenipin, and Its Enhanced Cytotoxity
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A new phosphatidyl derivative, 1,2-dipalmitoyl-3-sn-phosphatidylgenipin (DPP-genipin), was found to be synthesized by the transfer reaction of a dipalmitoylphosphatidyl residue from 1,2-dipalmitoyl-3-sn-phosphatidylcholine to genipin by phospholipase D (P
- Takami, Masaaki,Suzuki, Yukio
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p. 1897 - 1898
(2007/10/02)
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- THE PRACTICAL METHOD FOR THE PREPARATION OF IRIDOID AGLYCONS FROM THEIR GLYCOSIDES
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The liberation of iridoid aglycons from their glycosides is achieved by the successive treatment with sodium metaperiodate, sodium borohydride, and hydrochloric acid in one pot operation.This simple and efficient method has advantages over the enzymatic hydrolysis from the preparative point of view.
- Tanaka, Masahide,Kigawa, Masaharu,Mitsuhashi, Hiroshi,Wakamatsu, Takeshi
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p. 1451 - 1454
(2007/10/02)
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