70094-79-0

Upstream product

• 24512-63-8 geniposide 
• 67-48-1 choline chloride 
• 24512-63-8 geniposide 
• 1174680-01-3 genipin 1-O-β-D-isomaltoside 

Downstream Products

• 69977-52-2 1-methoxygenipin 
• 1246811-62-0 C₁₈H₂₀O₅S 
• 1246811-53-9 C₁₈H₂₀O₄S 
• 24512-63-8 geniposide 
• 206755-40-0 1-benzyloxygenipin 

Relevant academic research and scientific papers

Transformation of geniposide into genipin by immobilized β-glucosidase in a two-phase aqueous-organic system

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).

Two new iridoid glycosides from Gardeniae Fructus

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%).

A PROCESS FOR PRODUCING GARDENIA BLUE PIGMENT FORM GENIPOSIDE

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.

An acid-stable β-glucosidase from Aspergillus aculeatus: Gene expression, biochemical characterization and molecular dynamics simulation

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.

BICYCLIC COMPOUND AND PHARMACEUTICAL COMPOSITION THEREOF FOR TREATING STROKE AND USE THEREOF

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.

Enhancement of active compound, genipin, from Gardeniae Fructus using immobilized glycosyl hydrolase family 3 β-glucosidase from Lactobacillus antri

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.

A NEW PROCESS FOR PRODUCING GARDENIA BLUE PIGMENT

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.

NEW GARDENIA BLUE PIGMENT, PREPARATION AND USE THEREOF

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.

Preparation of a genipin blue from egg protein and genipin

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.

Iridoid glycosides from Gardeniae Fructus for treatment of ankle sprain

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