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(-)-Gallocatechin

$224

  • Brand : BIOFRON

  • Catalogue Number : BD-P0863

  • Specification : 98.0%(HPLC&TLC)

  • CAS number : 3371-27-5

  • Formula : C15H14O7

  • Molecular Weight : 306.27

  • PUBCHEM ID : 9882981

  • Volume : 25mg

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Catalogue Number

BD-P0863

Analysis Method

Specification

98.0%(HPLC&TLC)

Storage

-20℃

Molecular Weight

306.27

Appearance

White powder

Botanical Source

This product is isolated and purified from the wood of Acacia catechu (L.F.) Willd.

Structure Type

Category

SMILES

C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)O

Synonyms

(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,5,7-chromanetriol/(2S,3R)-2-(3,4,5-Trihydroxyphenyl)chromane-3,5,7-triol/2H-1-Benzopyran-3,5,7-triol, 3,4-dihydro-2-(3,4,5-trihydroxyphenyl)-, (2S,3R)-/(2S,3R)-2-(3,4,5-Trihydroxyphenyl)-3,4-dihydro-1(2H)-benzopyran-3,5,7-triol/(2S,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol/(2S,3R)-2-(3,4,5-Trihydroxyphenyl)chroman-3,5,7-triol/(-)-Gallocatechin/Gallocatechol

IUPAC Name

Applications

Biol Pharm Bull. 2015;38(2):325-30. Biotransformation of (-)-epigallocatechin and (-)-gallocatechin by intestinal bacteria involved in isoflavone metabolism.[Pubmed: 25747993]Four isoflavone-metabolizing bacteria were tested for their abilities to degrade (-)-epigallocatechin (EGC) and its isomer (-)-Gallocatechin (GC). METHODS AND RESULTS:Biotransformation of both EGC and GC was observed with Adlercreutzia equolifaciens JCM 14793, Asaccharobacter celatus JCM 14811, and Slackia equolifaciens JCM 16059, but not Slackia isoflavoniconvertens JCM 16137. With respect to the degradation of EGC, strain JCM 14793 only catalyzed 4'-dehydroxylation to produce 4'-dehydroxylated EGC (7). Strain JCM 14811 mainly produced 7, along with a slight formation of the C ring-cleaving product 1-(3,4,5-trihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol (1). Strain JCM 16059 catalyzed only C ring cleavage to form 1. Interestingly, the presence of hydrogen promoted the bioconversion of EGC by these bacteria. In addition, strain JCM 14811 revealed the ability to catalyze 4'-dehydroxylation of 1 to yield 1-(3,5-dihydroxyphenyl)-3-(2,4,6-trihydroxyphenyl)propan-2-ol (2) in the presence of hydrogen. In the case of GC, strain JCM 14793 mainly produced C ring-cleaving product (1) with only a very small amount of 4'-dehydroxylated GC (8), while Strain JCM 14811 only catalyzed 4'-dehydroxylation to form 8. Strain JCM 16059 formed 1. The bioconversion of GC by the three strains was stimulated by hydrogen. Strain JCM 14793 showed the ability to convert 1 into 2 in the presence of hydrogen as did strain JCM 14811. Furthermore, strains JCM 14793 and JCM 14811 were found to have the ability to catalyze p-dehydroxylation of the pyrogallol moiety in the EGC metabolites 4-hydroxy-5-(3,4,5-trihydroxyphenyl)valeric acid (3) and 5-(3,4,5-trihydroxyphenyl)-γ-valerolactone (4), and this ability was enhanced by the presence of hydrogen.

Density

1.7±0.1 g/cm3

Solubility

Methanol; Acetontrile; DMSO

Flash Point

368.5±31.5 °C

Boiling Point

685.6±55.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

XMOCLSLCDHWDHP-DOMZBBRYSA-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#:3371-27-5) 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

31910001

Abstract

Ginkgo biloba L. leaves are a flavonoid resource for the pharmaceutical industry. The flavonoid 3′-hydroxylase (F3’H) is a key enzyme in the flavonoid biosynthesis pathway. However, the role of F3’H in flavonoid biosynthesis and metabolism is unclear. In this study, we characterized and functionally analyzed the ginkgo F3’H gene GbF3’H1 that encodes a protein of 520 amino acids. Expression profiling showed that GbF3’H1 was highly expressed in the leaves of ginkgo in September. Subcellular localization showed that GbF3’H1 occurred predominately in the cytoplasm. Transgenic poplars overexpressing GbF3’H1 had more red pigmentation in leaves than did wild-type (WT) plants. Furthermore, the concentrations of epigallocatechin, gallocatechin, and catechin in the downstream products synthesized by flavonoids were significantly higher in the transgenic plants than in the WT plants. These results indicate that the overexpression of GbF3’H1 enhances flavonoid production in transgenic plants and provides new insights into flavonoid biosynthesis and metabolism.

KEYWORDS

flavonoid; gene function; metabolite; transgenic plant

Title

Overexpression of the GbF3'H1 Gene Enhanced the Epigallocatechin, Gallocatechin, and Catechin Contents in Transgenic Populus.

Author

Wu Y1,2, Wang T2, Xin Y1, Wang G1, Xu LA1.

Publish date

2020 Jan 29

PMID

31756664

Abstract

Structural investigations, based on density functional theory (DFT) calculations, are performed on tea catechins, including 4-aminobutyric acid (GABA), L-theanine (Thea), caffeine (CAF), theobromine (TB), theophylline (TP), catechin (C), epicatechin (EC), gallocatechin (GC), epigallocatechin (EGC), catechin gallate (CG), epicatechin gallate (ECG), gallocatechin gallate (GCG) and epigallocatechin gallate (EGCG). With an identified lowest energy conformer of investigated molecules, FTIR and FT-Raman spectra have been assigned according to DFT calculations in the way of B3LYP/6-31 + G (d, p). Normal spectra of these catechin powders are also measured by Raman spectrometers. There is a kind of everlasting correlation between experimental results and theoretical data. And our research has also obtained a clear evidence for reliable assignments of vibrational bands, bringing great feasibility to the rapid tea catechin detection.

Copyright © 2019 Elsevier B.V. All rights reserved.

KEYWORDS

Density functional theory; FT-IR; Raman spectra; Tea catechins

Title

Vibrational (FT-IR, Raman) analysis of tea catechins based on both theoretical calculations and experiments.

Author

Xia J1, Wang D2, Liang P3, Zhang4, Du X5, Ni D4, Yu Z6.

Publish date

2020 Jan;

PMID

31678671

Abstract

Epigallocatechin (EGC) was acylated with selected fatty acids, namely propionic acid [C3:0], caprylic acid [C8:0], lauric acid [C12:0], stearic acid [C18:0]) and docosahexaenoic acid (DHA)[C22:6n-3] in order to increase its lipophilicity. Monoesters were identified as the predominant products (~40%) followed by diesters (~33%), triesters (~9%) and trace amounts of tetra- and pentaesters. 1H NMR, 13C NMR and HPLC-DAD-MS were used to elucidate the acylation sites and structures of new EGC esters. According to the HPLC-MS analysis of the caprylate esters, EGC-4′-O-caprylate (27%), EGC-3′-O-caprylate or EGC-5′-O-caprylate (12%) and EGC-3′,5′-O-dicaprylate (16%) were the major compounds generated upon the acylation reaction of EGC. The acylation significantly increased the lipophilicity of EGC. In addition, EGC and its esters showed radical scavenging activities against DPPH radical and ABTS radical cation. Therefore, EGC esters could serve as potential sources of antioxidants for application in both hydrophilic and lipophilic media.

Copyright © 2019. Published by Elsevier Ltd.

KEYWORDS

Acylation; Antioxidant activities; Epigallocatechin (EGC); Fatty acids; Green tea catechins; Lipophilicity

Title

Epigallocatechin (EGC) esters as potential sources of antioxidants.

Author

Ambigaipalan P1, Oh WY1, Shahidi F2.

Publish date

2020 Mar 30;