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Epitheaflagallin 3-O-gallate

$576

  • Brand : BIOFRON

  • Catalogue Number : BD-D0040

  • Specification : HPLC≥98%

  • CAS number : 102067-92-5

  • Formula : C27H20O13

  • Molecular Weight : 552.444

  • PUBCHEM ID : 467319

  • Volume : 5mg

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Catalogue Number

BD-D0040

Analysis Method

HPLC,NMR,MS

Specification

HPLC≥98%

Storage

-20℃

Molecular Weight

552.444

Appearance

Powder

Botanical Source

Black Tea

Structure Type

Category

Standards;Natural Pytochemical;API

SMILES

C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=O)C(=C4C(=C3)C=C(C(=C4O)O)O)O)OC(=O)C5=CC(=C(C(=C5)O)O)O

Synonyms

epitheaflagallin-3-O-gallate

IUPAC Name

[(2R,3R)-5,7-dihydroxy-2-(2,3,4,5-tetrahydroxy-6-oxobenzo[7]annulen-8-yl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate

Applications

Epitheaflagallin 3-O-gallate is a minor polyphenol in black tea. Epitheaflagallin 3-O-gallate exhibits versatile physiological functions in vivo and in vitro, including antioxidative activity, pancreatic lipase inhibition, Streptococcus sorbinusglycosyltransferase inhibition, and an inhibiting effect on the activity of matrix metalloprotease-1 and -3 and their synthesis by human gingival fibroblasts[1].

Density

Solubility

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

Flash Point

Boiling Point

Melting Point

InChl

InChI=1S/C27H20O13/c28-12-6-14(29)13-8-20(40-27(38)11-4-15(30)22(34)16(31)5-11)26(39-19(13)7-12)10-1-9-2-18(33)24(36)25(37)21(9)23(35)17(32)3-10/h1-7,20,26,28-31,33-34,36-37H,8H2,(H,32,35)/t20-,26-/m1/s1

InChl Key

CMGRMMSVGCHWOK-FQRUVTKNSA-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#:102067-92-5) 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

29131612

Abstract

Epitheaflagallin (ETFG) and epitheaflagallin 3-O-gallate (ETFGg) are minor polyphenols in black tea extract that are enzymatically synthesized from epigallocatechin (EGC) and epigallocatechin gallate (EGCg), respectively, in green tea extract via laccase oxidation in the presence of gallic acid. The constituents of laccase-treated green tea extract in the presence of gallic acid are thus quite different from those of nonlaccase-treated green tea extract: EGC and EGCg are present in lower concentrations, and ETFG and ETFGg are present in higher concentrations. Additionally, laccase-treated green tea extract contains further polymerized catechin derivatives, comparable with naturally fermented teas such as oolong tea and black tea. We found that ETFGg and laccase-treated green tea extracts exhibit versatile physiological functions in vivo and in vitro, including antioxidative activity, pancreatic lipase inhibition, Streptococcus sorbinus glycosyltransferase inhibition, and an inhibiting effect on the activity of matrix metalloprotease-1 and -3 and their synthesis by human gingival fibroblasts. We confirmed that these inhibitory effects of ETFGg in vitro match well with the results obtained by docking simulations of the compounds with their target enzymes or noncatalytic protein. Thus, ETFGg and laccase-treated green tea extracts containing ETFGg are promising functional food materials with potential antiobesity and antiperiodontal disease activities.

KEYWORDS

n 3-O-gallate (ETFGg); glycosyltransferase inhibition; laccase-treated green tea extract; matrix metalloprotease inhibition; pancreatic lipase inhibition; theaflavin 3-O-gallate (TFA 3-O-gallate)

Title

Functional Characterization of Epitheaflagallin 3-O-GallateGenerated in Laccase-Treated Green Tea Extracts in the Presence of Gallic Acid.

Author

Itoh N, Kurokawa J, Isogai Y, Ogasawara M1, Matsunaga T1, Okubo T2, Katsube Y3.

Publish date

2017 Dec 6

PMID

26672458

Abstract

Epitheaflagallin 3-O-gallate (ETFGg) is a minor polyphenol found in black tea extract, which has good physiological functions. It is synthesized from epigallocatechin gallate (EGCg) with gallic acid via laccase oxidation. Various basidiomycetes and fungi were screened to find a suitable laccase for the production of ETFGg. A basidiomycete, Hericium coralloides NBRC 7716, produced an appropriate extracellular laccase. The purified laccase produced twice the level of ETFGg compared with commercially available laccase from Trametes sp. The enzyme, termed Lcc2, is a monomeric protein with an apparent molecular mass of 67.2 kDa. The N-terminal amino acid sequence of Lcc2 is quite different from laccase isolated from the fruiting bodies of Hericium. Lcc2 showed similar substrate specificity to known laccases and could oxidize various phenolic substrates, including pyrogallol, gallic acid, and 2,6-dimethoxyphenol. The full-length lcc2 gene was obtained by PCR using degenerate primers, which were designed based on the N-terminal amino acid sequence of Lcc2 and conserved copper-binding sites of laccases, and 5′-, and 3′-RACE PCR with mRNA. The Lcc2 gene showed homology with Lentinula edodes laccase (sharing 77% amino acid identity with Lcc6). We successfully produced extracellular Lcc2 using a heterologous expression system with Saccharomyces cerevisiae. Moreover, it was confirmed that the recombinant laccase generates similar levels of ETFGg as the native enzyme.

Copyright © 2015 Elsevier Inc. All rights reserved.

KEYWORDS

Enzymatic synthesis; Epitheaflagallin 3-O-gallate (ETFGg); Hericium coralloides NBRC 7716; Laccase lcc2

Title

Characterization and cloning of laccase gene from Hericium coralloides NBRC 7716 suitable for production of epitheaflagallin 3-O-gallate.

Author

Itoh N1, Takagi S2, Miki A2, Kurokawa J2.

Publish date

2016 Jan