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Orobol

$572

  • Brand : BIOFRON

  • Catalogue Number : BD-P0378

  • Specification : 98.0%(HPLC)

  • CAS number : 480-23-9

  • Formula : C15H10O6

  • Molecular Weight : 286.2

  • PUBCHEM ID : 5281801

  • Volume : 10mg

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Catalogue Number

BD-P0378

Analysis Method

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

286.2

Appearance

Yellow powder

Botanical Source

This product is isolated and purified from the herb of Wisteria sinensis

Structure Type

Category

SMILES

C1=CC(=C(C=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O)O

Synonyms

3-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one

IUPAC Name

Applications

Density

1.7±0.1 g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

239.5±25.0 °C

Boiling Point

616.1±55.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

IOYHCQBYQJQBSK-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:480-23-9) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

30365230

Abstract

This study was conducted to screen flavonoids for affecting expression of desaturases involved in omega-3 fatty acid synthesis and ceramide (CER) metabolism. To this end, cultured HepG2 hepatocytes, C2C12 myocytes, and 3T3-L1 adipocytes were treated with nontoxic concentrations of 12 selected flavonoids and expression of Δ4-, Δ5-, and Δ6-desaturases (DEGS1, FADS1, and FADS2, respectively) was determined. The flavonoids tested were more cytotoxic to HepG2 and 3T3-L1 than to C2C12 cells. In HepG2 cells, FADS1 was induced by quercetin and FADS2 expression was increased by daidzein, genistein, and pratensein treatment. DEGS1 was increased by apigenin, luteolin, orobol, and quercetin administration. In differentiated C2C12 cells, substances had no inducing effect or even lowered target gene expression. Pratensein induced both FADS1 and FADS2 in differentiated 3T3-L1 cells and DEGS1 was increased by treatment with apigenin, genistein, luteolin, orobol, and quercetin. In conclusion, pratensein may be an interesting test compound for further studies in vitro and in vivo on omega-3 synthesis since it induces its rate-limiting enzyme FADS2. Apigenin, luteolin, orobol, and quercetin induced DEGS1 and thereby possibly synthesis of proapoptotic CER in malignant HepG2 cells and 3T3-L1. In contrast, in benign C2C12 cells, they did not elevate mRNA steady state levels of DEGS1. That may partly explain the higher resistance of C2C12 cells against flavonoids compared to the other cell lines. By affecting tumor cells and nontumor cells differently, these flavonoids may be promising substances for further research regarding anticancer properties. © 2018 BioFactors, 44(5):485-495, 2018.

KEYWORDS

Flavonoids, omega-3, ceramide, desaturases, cultured cells.

Title

Flavonoids as putative modulators of Δ4-, Δ5-, and Δ6-desaturases: Studies in cultured hepatocytes, myocytes, and adipocytes

Author

Gianna Kuhn 1, Kathrin Pallauf 1, Carsten Schulz 2 3, Gerald Rimbach 1

Publish date

2018 Sep;

PMID

30011063

Abstract

Tyrosinase is a type 3 copper oxygenase that catalyzes a phenol moiety into ortho-diphenol, and subsequently to ortho-quinone. Diverse tyrosinases have been observed across the kingdom including Animalia, Bacteria, Plantae, and Fungi. Among the tyrosinases, bacterial, and mushroom tyrosinases have been extensively exploited to prepare melanin, ortho-hydroxy-polyphenols, or novel plant secondary metabolites during the past decade. And their use as a biocatalyst to prepare various functional biocompounds have drawn great attention worldwide. Herein, we tailored a bacterial tyrosinase from Bacillus megaterium (BmTy) using circular permutation (CP) engineering technique which is a novel enzyme engineering technique to covalently link original N and C termini and create new termini on the middle of its polypeptide. To construct a smart rationally-designed CP library, we introduced 18 new termini at the edge of each nine loops that link 伪-helical secondary structure in BmTy. Among the small library, seven functional CP variants were successfully identified and they represented dramatic change in their enzyme characteristics including kinetic properties and substrate specificity. Especially, cp48, 102, and 245 showed dramatically decreased tyrosine hydroxylase activity, behaving like a catechol oxidase. Exploiting the dramatic increased polyphenol oxidation activity of cp48, orobol (3′-hydroxy-genistein) was quantitatively synthesized with 1.48 g/L, which was a 6-fold higher yield of truncated wild-type. We examined their kinetic characters through structural speculation, and suggest a strategy to solubilize the insoluble artificial variants effectively.

KEYWORDS

circular permutation; orobol; polyphenol oxidase; protein engineering; tyrosinase.

Title

Circular permutation of a bacterial tyrosinase enables efficient polyphenol-specific oxidation and quantitative preparation of orobol

Author

Pyung-Gang Lee 1 2, Sang-Hyuk Lee 1 2, Eun Young Hong 1 2, Stefan Lutz 3, Byung-Gee Kim 1 2 4 5

Publish date

2019 Jan;

PMID

29737209

Abstract

Hepatitis C virus (HCV) is recognized as a major causative agent of chronic hepatitis, cirrhosis, and hepatocellular carcinoma. Despite rapid progress in the development of direct-acting antivirals (DAA) against HCV infection in recent years, cost-effective antiviral drugs with more affordable prices still need to be developed. In this study, we screened a library of natural compounds to identify natural HCV inhibitors. The library of the pure compounds extracted from Chinese herbs deposited in the chemical bank of National Research Institute of Chinese Medicine (NRICM), Taiwan was screened in the cell culture-derived HCV (HCVcc) system. We identified the flavone or flavan-based compounds amentoflavone, 7,4[Formula: see text]-dihydroxyflavanone, and orobol with the inhibition of viral entry, replication, and translation of the HCV life cycle. Amentoflavone and orobol also showed inhibitory effects on resistant-associated variants to the NS5A inhibitor daclatasvir. The results of this study have the potential to benefit patients who are intolerant to the adverse effect of pegylated interferon or who harbor resistant strains refractory to treatment by current direct-acting antiviral agents.

KEYWORDS

Amentoflavone; Daclatasvir; HCV; Orobol; Resistance-Associated Variant.

Title

Inhibitory Effects of Amentoflavone and Orobol on Daclatasvir-Induced Resistance-Associated Variants of Hepatitis C Virus

Author

Wei-Ping Lee 1 2, Keng-Li Lan 3 4, Shi-Xian Liao 5, Yi-Hsiang Huang 5 6 7, Ming-Chih Hou 5 6, Keng-Hsin Lan 5 6 8

Publish date

2018