486-62-4

Usage

Uses

Used in Animal Feed Industry:
Ononin is used as a plant estrogen for enhancing the growth and reproductive performance of animals in the animal feed industry. As a potent estrogen, it can improve the overall health and well-being of animals, leading to better productivity and efficiency in the livestock sector.
Used in Pharmaceutical Industry:
Ononin is used as a pharmaceutical compound for its potential estrogenic effects. It can be utilized in the development of drugs targeting hormone-related conditions, such as menopause, osteoporosis, and certain types of cancer. Its estrogenic properties make it a valuable candidate for research and development in the pharmaceutical industry.
Used in Research and Development:
Ononin is used as a research compound for studying the effects of plant estrogens on various biological processes. Its unique structure and potent estrogenic activity make it an interesting subject for scientific investigations, which can lead to a better understanding of the role of plant estrogens in human and animal health.

InChI:InChI=1/C22H22O9/c1-28-12-4-2-11(3-5-12)15-10-29-16-8-13(6-7-14(16)18(15)24)30-22-21(27)20(26)19(25)17(9-23)31-22/h2-8,10,17,19-23,25-27H,9H2,1H3/t17-,19-,20+,21-,22-/m1/s1

Upstream product

• 42868-84-8 formononetin tetra-O-acetyl-β-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide 
• 485-72-3 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 492-61-5 β-D-glucose 
• 133-89-1 UDP-glucose 
• 2280-44-6 D-Glucose 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 485-72-3 7-Hydroxy-3-(4-methoxy-phenyl)-chromen-4-on 
• 2280-44-6 D-Glucose 
• 13293-49-7 3-(4-methoxyphenyl)-4-oxo-4H-chromene-7-yl acetate 
• 113960-55-7 bufalin-3-(β-D-glucoside) 

Relevant academic research and scientific papers

An improved phase transfer catalyzed synthetic method for ononin and rothindin

An improved and mild glycosylation reaction was developed and used for the synthesis of ononin and rothindin, two naturally occurring isoflavone glycosides by a modified phase transfer catalyzed process.

Two trifunctional leloir glycosyltransferases as biocatalysts for natural products glycodiversification

Two promiscuous Bacillus licheniformis glycosyltransferases, YdhE and YojK, exhibited prominent stereospecific but nonregiospecific glycosylation activity of 20 different classes of 59 structurally different natural and non-natural products. Both enzymes transferred various sugars at three nucleophilic groups (OH, NH2, SH) of diverse compounds to produce O-, N-, and S-glycosides. The enzymes also displayed a catalytic reversibility potential for a one-pot transglycosylation, thus bestowing a cost-effective application in biosynthesis of glycodiversified natural products in drug discovery.

A flavonoid glucoside preparation method (by machine translation)

The invention belongs to the technical field of drug synthesis, relates to a flavonoid glucoside preparation method. Specifically, the preparation method of the present invention the flavonoid aglycon, honey, solvent and at least one of a catalytic amount of a product of said flavonoid glucoside mixed in the reaction container, sealing the reaction vessel and the heating, cooling to room temperature after the completion of reaction, can complete the conversion of the glucoside to the aglycon. The preparation obtained by the method of the glucoside of high conversion rate, in the absence of the strong acid, heavy metal salt and a phase transfer catalyst such as the premise of, only by adding honey and as the target product of the glucoside can be completed in a short time the whole reaction process, low cost, high efficiency, simple operation, environment-friendly. (by machine translation)

Regio- and Stereospecific O-Glycosylation of Phenolic Compounds Catalyzed by a Fungal Glycosyltransferase from Mucor hiemalis

Glycosylated small molecules are often bioactive and obtained mainly via microbial biotransformation especially by fungi. However, no responsible glycosylation gene/enzyme has yet been uncovered in a filamentous fungus. We report here the first identification of a phenolic glycosyltransferase MhGT1 from Mucor hiemalis. The substrate promiscuity of the new phenolic O-glycosyltransferase was explored by using phenols from Traditional Chinese Medicinal herbs as substrates. MhGT1 exhibited robust capabilities for the regio- and stereospecific O-glycosylation of 72 structurally diverse drug-like scaffolds and sterols with uridine diphosphate (UDP) glucose as a sugar donor. Unprecedentedly, MhGT1 showed higher regiospecificities and activities for prenylated phenols than for their non-prenylated analogues. Computational modelling of MhGT1 uncovered a truncated N-terminal domain of the enzyme consisting of hydrophobic and charged amino acid residues which contributed to the broad substrate scope and regiospecificity towards prenylated compounds. Our findings expand the ways to obtain new glycosyltransferases and also effectively apply the enzymatic approach to obtain glycosylated compounds in drug discovery. (Figure presented.).

TEMPO-Mediated Regiospecific Oxidation of Glucosides to Glucuronides

A TEMPO/hypochlorite/bromide oxidant has been used for the conversion of aryl and steroidal glucosides to the corresponding glucuronide conjugates in good (48-74%) yield. An isoflavone glucoside failed to undergo this transformation.

The phase transfer catalysed synthesis of isoflavone-O-glucosides

Daidzin 1, genistin 2, ononin 3 and sissotrin 4 are the major products of the phase transfer catalysed reaction between the isoflavone aglycones daidzein, genistein, formononetin and biochanin A, respectively, and 1-bromo-2,3,4,6-tetra-O-acetyl-α-glucopyranose. Complete proton and carbon NMR assignments are presented for compounds 1-4.