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Flazin

$1,056

  • Brand : BIOFRON

  • Catalogue Number : BN-O0979

  • Specification : 98%(HPLC)

  • CAS number : 100041-05-2

  • Formula : C17H12N2O4

  • Molecular Weight : 308.29

  • PUBCHEM ID : 5377686

  • Volume : 5mg

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Catalogue Number

BN-O0979

Analysis Method

HPLC,NMR,MS

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

308.29

Appearance

Yellow powder

Botanical Source

Structure Type

Category

Standards;Natural Pytochemical;API

SMILES

C1=CC=C2C(=C1)C3=CC(=NC(=C3N2)C4=CC=C(O4)CO)C(=O)O

Synonyms

Flazine/3-carboxylperlolyrine/Flazin/9H-Pyrido[3,4-b]indole-3-carboxylic acid,1-[5-(hydroxymethyl)-2-furanyl]

IUPAC Name

1-[5-(hydroxymethyl)furan-2-yl]-9H-pyrido[3,4-b]indole-3-carboxylic acid

Density

1.513g/cm3

Solubility

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

Flash Point

351.2ºC

Boiling Point

657.1ºC at 760mmHg

Melting Point

InChl

InChI=1S/C20H25N2O/c1-3-12-10-22(2)18-9-15-13-6-4-5-7-17(13)21-20(15)19(22)8-14(12)16(18)11-23/h3-7,14,16,18-19,21,23H,8-11H2,1-2H3/q+1

InChl Key

USBWYUYKHHILLZ-UHFFFAOYSA-N

WGK Germany

RID/ADR

HS Code Reference

2933990000

Personal Projective Equipment

Correct Usage

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

Meta Tag

provides coniferyl ferulate(CAS#:100041-05-2) 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

31668063

Abstract

Flazin is a β-carboline-derived alkaloid found in Japanese fermented foods. Here, the potential of flazin as an antioxidant food was studied with particular reference to its effect on the Kelch-like ECH-associated protein 1 (Keap1)-nuclear factor erythroid 2-related factor 2 (Nrf2) system in human hepatocytes (C3A). Flazin and flazin analogues including the decarboxylated derivative perlolyrine were chemically synthesized and compared with each other and with chlorogenic acid and curcumin. Among these compounds, flazin showed the lowest cytotoxicity (IC50 < 500 μM) and the highest capacity to activate the Keap1-Nrf2 system. It provided the largest (>3-fold of the control) cytoprotection ability against a pro-oxidant, although its radical absorbance capacity was relatively low. Flazin increased the expressions of Nrf2-dependent phase II enzyme genes and their products (NQO1, GSTP, and GSH proteins). The strong cytoprotection ability of flazin associated with low log P (0-3) is shared by sulforaphane and 3,5-dihydroxy-4-methoxybenzyl alcohol, suggesting the potential value of flazin and flazin-rich foods for the prevention of oxidation-related health disorders.

KEYWORDS

Keap1; Nrf2; ORAC; flazin; hepatocyte; phase II enzyme.

Title

Flazin as a Promising Nrf2 Pathway Activator

Author

Hirotoshi Fuda 1, Satoshi Miyanaga 1, Takayuki Furukawa 1, Satomi Umetsu 1, Sae Joko 1, Yuning Roan 1, Hirotaka Suzuki 1, Shu-Ping Hui 1, Mitsugu Watanabe 2, Hitoshi Chiba 3

Publish date

2019 Nov 20

PMID

27181598

Abstract

This is the first report on the ability of soy sauce to effectively reduce the serum uric acid levels and xanthine oxidase (XOD) activities of hyperuricemic rats. Soy sauce was partitioned sequentially into ethyl acetate and water fractions. The ethyl acetate fraction with strong XOD inhibition effect was purified further. On the basis of xanthine oxidase inhibitory (XOI) activity-guided purification, nine compounds including 3,4-dihydroxy ethyl cinnamate, diisobutyl terephthalate, harman, daidzein, flazin, catechol, thymine, genistein, and uracil were obtained. It was the first time that 3,4-dihydroxy ethyl cinnamate and diisobutyl terephthalate had been identified from soy sauce. Flazin with hydroxymethyl furan ketone group at C-1 and carboxyl at C-3 exhibited the strongest XOI activity (IC50 = 0.51 ± 0.05 mM). According to fluorescence quenching and molecular docking experiments, flazin could enter into the catalytic center of XOD to interact with Lys1045, Gln1194, and Arg912 mainly by hydrophobic forces and hydrogen bonds. Flazin, catechol, and genistein not only were potent XOD inhibitors but also held certain antioxidant activities. According to ADME (absorption, distribution, metabolism, and excretion) simulation in silico, flazin had good oral bioavailability in vivo.

KEYWORDS

flazin; hyperuricemia; soy sauce; xanthine oxidase; xanthine oxidase inhibitory activity.

Title

Effect of Soy Sauce on Serum Uric Acid Levels in Hyperuricemic Rats and Identification of Flazin as a Potent Xanthine Oxidase Inhibitor

Author

Huipin Li 1 2, Mouming Zhao 1 2 3, Guowan Su 1 2, Lianzhu Lin 1 2, Yong Wang 4

Publish date

2016 Jun 15

PMID

3369932

Title

beta-Carbolines From Japanese Sake and Soy Sauce: Synthesis and Biological Activity of Flazin and Yellow Substance YS (Perlolyrine)

Author

W P Gessner, A Brossi, M E Bembenek, C W Abell

Publish date

1988 Feb;


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