491-71-4

Usage

Uses

Used in Pharmaceutical Industry:
Chrysoeriol is used as a pharmaceutical agent for its selective inhibition of the formation of a carcinogenic estrogen metabolite in MCF-7 breast cancer cells. This property makes it a promising candidate for the development of anticancer treatments and prevention strategies.
Used in Cancer Research:
In the field of cancer research, Chrysoeriol is utilized for its potential role in inhibiting the formation of carcinogenic estrogen metabolites. This application aids in understanding the underlying mechanisms of cancer development and progression, as well as in the identification of novel therapeutic targets.
Used in Drug Development:
Chrysoeriol's ability to selectively inhibit the formation of carcinogenic estrogen metabolites makes it a valuable compound in the development of new drugs for cancer treatment. Its unique properties can be harnessed to create more effective and targeted therapies for various types of cancer.
Used in Nutraceutical Industry:
Due to its potential health benefits, Chrysoeriol can be used as an ingredient in the nutraceutical industry. It can be incorporated into dietary supplements and functional foods to provide consumers with added health benefits, such as cancer prevention and overall wellness support.

InChI:InChI=1/C16H12O6/c1-21-14-4-8(2-3-10(14)18)13-7-12(20)16-11(19)5-9(17)6-15(16)22-13/h2-7,17-19H,1H3

Upstream product

• 876472-69-4 2-[4-(benzyloxy)-3-methoxyphenyl]-5,7-dihydroxy-4H-chromen-4-one 
• 446-71-9 (+/-)-homoeriodictyol 
• 62346-14-9 7,4′-dihydroxy-5,3′-dimethoxyflavone 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 123656-61-1 crotonoylthermopsoside 
• 89759-25-1 chrysoeriol 6-C-anti-α-D-glucopyranoside 
• 19993-32-9 chrysoeriol 7-O-glucoside 
• 2426-87-1 3-methoxy-4-(phenylmethoxy)benzaldehyde 
• 1486-53-9 4-(benzyloxy)-3-methoxybenzoic acid 
• 1592-47-8 4-(benzyloxy)-3-methoxybenzoic anhydride 
• 121-33-5 vanillin 
• 1215845-89-8 5,7,4'-trihydroxy-3'-methoxyflavone-4'-O-β-D-(2''-O-acetyl)glucopyranoside 
• 1290638-51-5 1-(2-hydroxy-4,6-bis(methoxymethoxy)phenyl)-3-(3-methoxy-4-(methoxymethoxy)phenyl)prop-2-en-1-one 
• 480-66-0 2,4,6-trihydroxyacetophenone 

Downstream Products

• 3162-24-1 7-acetoxy-2-(4-acetoxy-3-methoxy-phenyl)-5-hydroxy-chromen-4-one 
• 3162-04-7 chrysoeriol tri-O-acetate 
• 29741-07-9 5,4'-dihydroxy-3'-methoxyflavone-7-O-β-galacturonide 
• 76735-58-5 6-prenylchrysoeriol 
• 76735-57-4 canniflavone-2 

Relevant academic research and scientific papers

Structural determination of abutilins A and B, new flavonoids from Abutilon pakistanicum, by 1D and 2D NMR spectroscopy

Two new flavonoids, abutilin A and B, were isolated from the chloroform soluble fraction of Abutilon pakistanicum and their structures assigned from 1H and 13C NMR spectra, DEPT and by 2D COSY, HMQC and HMBC experiments. Ferulic acid (3), (E)-cinnamic acid (4), 5-hydroxy-4′,6,7,8- tetramethoxyflavone (5), kaempferol (6), luteolin (7) and luteolin 7-O-β-D-glucopyranoside (8) have also been reported from this species. Copyright

The fungal leaf endophyte Paraconiothyrium variabile specifically metabolizes the host-plant metabolome for its own benefit

Fungal endophytes live inside plant tissues and some have been found to provide benefits to their host. Nevertheless, their ecological impact is not adequately understood. Considering the fact that endophytes are continuously interacting with their hosts, it is conceivable that both partners have substantial influence on each other's metabolic processes. In this context, we have investigated the action of the endophytic fungus Paraconiothyrium variabile, isolated from the leaves of Cephalotaxus harringtonia, on the secondary metabolome of the host-plant. The alteration of the leaf compounds by the fungus was monitored through metabolomic approaches followed by structural characterization of the altered products. Out of more than a thousand molecules present in the crude extract of the plant leaf, we have observed a specific biotransformation of glycosylated flavonoids by the endophyte. In all cases it led to the production of the corresponding aglycone via deglycosylation. The deglycosylated flavonoids turned out to display significant beneficial effects on the hyphal growth of germinated spores. Our finding, along with the known allelopathic role of flavonoids, illustrates the chemical cooperation underlying the mutualistic relationship between the plant and the endophyte.

Anti‐melanogenic properties of velutin and its analogs?

Velutin, one of the flavones contained in natural plants, has various beneficial activities, such as skin whitening, as well as anti‐inflammatory, anti‐allergic, antioxidant, and antimicrobial activities. However, the relationship between the structure of velutin and its anti‐melanogenesis activity is not yet investigated. In this study, we obtained 12 velutin derivatives substituted at C5, C7, C3′, and C4′ of the flavone backbone with hydrogen, hydroxyl, and methoxy functionalities by chemical synthesis, to perform SAR analysis of velutin structural analogues. The SAR study revealed that the substitution of functional groups at C5, C7, C3′, and C4′ of the flavone backbone affects biological activities related to melanin synthesis. The coexistence of hydroxyl and methoxy at the C5 and C7 position is essential for inhibiting tyrosinase activity. However, 1,2‐diol compounds substituted at C3′ and C4′ of flavone backbone induce apoptosis of melanoma cells. Further, substitution at C3′ and C4′ with methoxy or hydrogen is essential for inhibiting melanogenesis. Thus, this study would be helpful for the development of natural‐derived functional materials to regulate melanin synthesis.

New Flavonoids from Artemisia frigida

New flavonoids were isolated from the aerial part of Artemisia frigida Willd. (Asteraceae). Their structures were elucidated using UV, IR, and NMR spectroscopy and mass spectrometry as chrysoeriol-7-O-(2′′-Oacetyl)-β-D-glucopyranoside (2′′-O-acetylthermop

Influence of Substrate Binding Residues on the Substrate Scope and Regioselectivity of a Plant O-Methyltransferase against Flavonoids

Methylation of free hydroxyl groups is an important modification for flavonoids. It not only greatly increases absorption and oral bioavailability of flavonoids, but also brings new biological activities. Flavonoid methylation is usually achieved by a specific group of plant O-methyltransferases (OMTs) which typically exhibit high substrate specificity. Here we investigated the effect of several residues in the binding pocket of the Clarkia breweri isoeugenol OMT on the substrate scope and regioselectivity against flavonoids. The mutation T133M, identified as reported in our previous publication, increased the activity of the enzyme against several flavonoids, namely eriodictyol, naringenin, luteolin, quercetin and even the isoflavonoid genistein, while a reduced set of amino acids at positions 322 and 326 affected both, the activity and the regioselectivity of the methyltranferase. On the basis of this work, methylated flavonoids that are rare in nature were produced in high purity.

Characterization of a Flavonoid 3’/5’/7-O-Methyltransferase from Citrus reticulata and Evaluation of the in Vitro Cytotoxicity of Its Methylated Products

O-methylation of flavonoids is an important modification reaction that occurs in plants. O-methylation contributes to the structural diversity of flavonoids, which have several biological and pharmacological functions. In this study, an O-methyltransferase gene (CrOMT2) was isolated from the fruit peel of Citrus reticulata, which encoding a multifunctional O-methyltransferase and could effectively catalyze the methylation of 3’-, 5’-, and 7-OH of flavonoids with vicinal hydroxyl substitutions. Substrate preference assays indicated that this recombinant enzyme favored polymethoxylated flavones (PMF)-type substrates in vitro, thereby providing biochemical evidence for the potential role of the enzyme in plants. Additionally, the cytotoxicity of the methylated products from the enzymatic catalytic reaction was evaluated in vitro using human gastric cell lines SGC-7901 and BGC-823. The results showed that the in vitro cytotoxicity of the flavonoids with the unsaturated C2-C3 bond was increased after being methylated at position 3’. These combined results provide biochemical insight regarding CrOMT2 in vitro and indicate the in vitro cytotoxicity of the products methylated by its catalytic reaction.

New Flavone Glycosides from Astragalus tanae Endemic to Georgia

The new flavone glycosides tanoside I and II in addition to three known flavonoids and daucosterol were isolated from the Georgian endemic species Astragalus tanae Sosn. Their structures were elucidated as chrysoeriol-7-O-β-D-glucopyranosyl-4′ -O-α-L-rham

Compounding method for chrysoeriol

The invention provides a compounding method for chrysoeriol, solving the problems of operation complexity and low yield in the prior art. The compounding method includes mixing anhydrous phloroglucinol with 3-methoxy-4-hydroxy-benzoyl ethyl acetate and dimethyl sulfoxide, heating and stirring the mixture, stopping heating to remove vacuum after complete vacuum reaction, cooling the mixture to roomtemperature, adding water, and performing stirring and filtering to obtain a crude chrysoeriol solid; subjecting the crude chrysoeriol solid to recrystallization by ethyl alcohol, and performing decoloration, concentration, recrystallization, filtration and drying to obtain the refined chrysoeriol. The compounding method has the advantages of simple and convenient procedure, simplicity in post-treatment, high yield of the whole process and applicability to large-scale industrial production.

Enzymatic production of oroxylin A and hispidulin using a liverwort flavone 6-O-methyltransferase

Oroxylin A and hispidulin, compounds which are abundant in both Scutellaria and liverwort species, are important lead compounds for the treatment of ischemic cerebrovascular disease. Their enzymatic synthesis requires an O-methyltransferase able to interact with the related flavonoid's 6-OH group, but such an enzyme has yet to be identified in plants. Here, the gene encoding an O-methyltransferase (designated PaF6OMT) was isolated from the liverwort species Plagiochasma?appendiculatum. A test of alternative substrates revealed that its strongest preferences were baicalein and scutellarein, which were converted into, respectively, oroxylin A and hispidulin. Allowed a sufficient reaction time, the conversion rate of these two substrates was, respectively, 90% and 100%. PaF6OMT offers an enzymatic route to the synthesis of oroxylin A and hispidulin.

A new synthesis for acacetin, chrysoeriol, diosmetin, tricin and other hydroxylated flavones by modified Baker-Venkataraman transformation

Baker-Venkataraman (BV) rearrangement is the method of choice for the synthesis of flavones. The major limitation of BV is that it requires extensive protections and deprotections of hydroxyl groups which make the process lengthy and cumbersome. In the present study, a three step efficient method has been developed using simple protecting groups and easily available starting materials. New syntheses for acacetin, chrysoeriol, diosmetin, tricin and other hydroxylated flavones are described.