149-91-7Relevant articles and documents
6″-Galloylpicein and other phenolic compounds from Arctostaphylos uva-ursi
Olennikov,Chekhirova
, p. 1 - 7 (2013)
Phenolic compounds from leafy shoots of A. uva-ursi (Ericaceae) were studied. The new phenolic glycoside 6″-galloylpicein and 40 known compounds were isolated. Roots of A. uva-ursi afforded 16 compounds. A C-glycoside of bergenin was found for the first time in the family Ericaceae. The dominant components of A. uva-ursi leaves according to HPLC were arbutin, (+)-catechin, and corilagin; of stems, picein and (+)-gallocatechingallate; of roots, (-)-epicatechin, (-)-epicatechingallate, and (+)-catechin.
Chemical transformation of oolongtheanin 3′-O-gallate in aqueous solution under heating conditions
Ochiai, Yuto,Ogawa, Kazuki,Sawada, Yoshiharu,Yanase, Emiko
, (2021)
To understand the stability of oolongtheanin 3′-O-gallate (1), present in oolong tea leaves, its chemical transformation in aqueous solution was investigated under heating conditions. Four compounds were obtained from 1, which were isolated and their chem
Hydrolyzable tannins from the fruits of Terminalia chebula Retz and their α-glucosidase inhibitory activities
Lee, Dong Young,Kim, Hyun Woo,Yang, Heejung,Sung, Sang Hyun
, p. 109 - 116 (2017)
Nine hydrolyzable tannins, including three previously unknown and six artifacts, were isolated, together with thirty-nine known ones, from the fruits of Terminalia chebula Retz. (Combretaceae). They were identified as 1,2,3-tri-O-galloyl-6-O-cinnamoyl-β-D
Purification and characterization of tannase and tannase gene from Enterobacter sp.
Sharma, Kanti Prakash,John
, p. 240 - 244 (2011)
Tannase of Enterobacter sp. was purified and characterized at molecular level. It was found to be 90 kDa in molecular weight. The purified enzyme showed maximum activity at 40 °C. The enzyme was also found to be active in acidic range of pH. The nucleotide and amino acid sequence of tannase exhibited resemblance with the other reported tannase sequences of bacteria, fungi and plants. Probably, this is the first report of tannase gene in Enterobacter sp. The investigation suggests that the purified enzyme can be useful to synthesize molecules of pharmaceutical interest. In addition to above, the enzyme tannase and the organism itself can also be employed to protect grazing animals and environment against the toxic effects caused by tannins in them.
Polyphenols in Ammania auriculata: Structures, antioxidative activity and cytotoxicity
Nawwar,Youb,El-Raey,Zaghloul,Hashem,Mostafa,Eldahshan,Werner,Becker,Haertel,Lindequist,Linscheid
, p. 860 - 864 (2014)
Chemical and biological investigations of the extract of Ammania auriculata (Lytheraceae) resulted in the identification of eight polyphenols (1 - 8) for the first time from this plant, including the gallotannin, 2,3,6-tri-O-galloyl-(α,β)-4Csu
MYRICATIN, A GALLOYL FLAVANONOL SULFATE AND PRODELPHINIDIN GALLATES FROM MYRICA RUBRA
Nonaka, Gen-Ichiro,Muta, Makiko,Nishioka, Itsuo
, p. 237 - 242 (1983)
An investigation of the bark of Myrica rubra has led to the isolation and characterization of myricatin (a galloyl flavanonol sulfate) and four new galloyl prodelphinidin dimers, together with gallic acid, (+/-)-gallocatechin and 3-O-galloyl-(-)-epicatechin.Evidence for the structures of these compounds was obtained from analyses of 1H AND 13C NMR spectra, and from hydrolytic studies.Key Word - Myrica rubra; Myricaceae; myricatin; galloyl flavanonol sulfate; prodelphinidin gallates; tannins.
Anthocyanin stability and recovery: Implications for the analysis of clinical and experimental samples
Woodward, Gary,Kroon, Paul,Cassidy, Aedin,Kay, Colin
, p. 5271 - 5278 (2009)
The proportion of ingested anthocyanins to reach the systemic circulation is reported to be a small percentage of their ingested dose. This may be due to physiochemical degradation in vivo or following routine sample treatment. Therefore, this study aimed
Hydrolyzed tannins from Geranium pusillum
Kobakhidze,Alaniya
, p. 262 - 264 (2003)
The polyphenolic compound 1-O-galloyl-3,6-hexahydroxybiphenyl-D- galactopyranoside (pusilagin) was isolated from the aerial part. The tannin structure was established using acid hydrolysis and IR, PMR, and 13C NMR spectral methods.
Solvent-free enzymatic synthesis of 1,2-dipalmitoylgalloylglycerol: Characterization and optimization of reaction condition
Zhang, Siyu,Hyatt, Joseph R.,Akoh, Casimir C.
, (2021)
A novel diacylglycerol-based galloyl structured lipid, 1,2-dipalmitoylgalloylglycerol (DPGG), was synthesized using the enzymatic transesterification of propyl gallate (PG) and tripalmitin under solvent-free condition. An immobilized and commercially available food-grade Candida antarctica lipase B, Lipozyme 435, was used as the biocatalyst. The reaction variables that affect the yield of DPGG were optimized using a 33 full factorial design. At 70 °C, DPGG was obtained at a yield of 33.0 ± 2.0% with PG conversion at 44.8 ± 1.8% when the following condition was used: 25 substrate molar ratio of tripalmitin to PG, 120 h reaction time, and 25% enzyme load relative to the total substrate weight. The structure of reaction product was elucidated using Fourier-transform infrared spectroscopy (FT-IR), electrospray ionization high-resolution accurate-mass tandem mass spectrometry (ESI-HRAM-MS/MS), and 1D and 2D nuclear magnetic resonance spectroscopy (NMR). The effects of different lipases and galloyl donors/acceptors on the transesterification were also investigated.
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Nierenstein
, p. 630 (1910)
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Enzymatic synthesis of gallic acid from tannic acid with an inducible hydrolase of Enterobacter spp
Sharma, Kanti Prakash,John,Goswami, Pawas,Soni, Manish
, p. 177 - 184 (2017)
Gallic acid acts as a precursor molecule to synthesize various tannin molecules. These are plant polyphenols and were proved to be good anti-oxidant, anti-cancerous, anti-inflammatory, anti-microbial compounds. In order to fully exploit prominent biological activities of specific tannins and to develop tannin-based new medicines, it is necessary to obtain their pure preparations with an aim of high yield and specificity. In the present study, gallic acid is synthesized by the hydrolysis of tannic acid using a microbial based transformation process. The microorganism was isolated and identified. The ability of the isolated microorganism to covert tannic acid into gallic acid was determined by HPLC and enzyme production.Highlights The present investigation signifies the role of Enterobacter spp. in various processes: ?To synthesize gallic acid (a precursor for food oxidant such as propyl gallate) and a bacteriostatic antibiotic (trimethoprim). ?To protect the environment from tannery’s discharge through the process of biodegradation. ?To reduce the toxicity of tannins in animal feed.
SCYLLO-QUERCITOL GALLATES AND HEXAHYDROXYDIPHENOATES FROM QUERCUS STENOPHYLLA
Nishimura, Hiroaki,Nonaka, Gen-Ichiro,Nishioka, Itsuo
, p. 2599 - 2604 (1986)
Key Word Index - Quercus stenophylla; Fagaceae; scyllo-quercitol; gallotannin; ellagitannin; gallic acid; hexahydroxydiphenic acid.A series of gallotannins and ellagitannins based on a scyllo-quercitol core have been isolated from the bark of Quercus stenophylla.On the basis of chemical and spectroscopic evidence, the structures of the gallotannins have been established as 2-O-, 1,2-di-O-, 1,2,3-tri-O-, 1,2,3,4-tetra-O- and 1,2,3,4,5-penta-O-galloyl-scyllo-quercitols, and the ellagitannins as 1,5-di-O-galloyl-2,3-(S)-hexahydroxydiphenoyl-scyllo-quercitol and 1,4-(or 4,5)-di-O-galloyl-2,3-(S)-hexahydroxydiphenoyl-scyllo-quercitol.
A novel adduct of ECG fused to piceid and four new dimeric stilbene glycosides from: Polygonum cuspidatum
Yang, Ya-Nan,Li, Fu-Shuang,Liu, Fu,Feng, Zi-Ming,Jiang, Jian-Shuang,Zhang, Pei-Cheng
, p. 60741 - 60748 (2016)
Polyflavanostilbene B (1), an unusual adduct of epicatechin-3-O-gallate fused to piceid through a carbon-carbon bond, four new dimeric stilbene glycosides (2-5), three new stilbene glucosides (6-8), one new flavan glucoside (9), and six known compounds were isolated from the rhizome of Polygonum cuspidatum. The structures of these compounds were elucidated using spectroscopic data, including electronic circular dichroism (ECD) and Rh2(OCOCF3)4-induced CD spectra. All of the compounds were screened for their inhibitory activity against α-glucosidase using acarbose as a positive control (IC50 = 385 μM), and strong inhibitory activity against α-glucosidase was observed for compound 8 (IC50 = 3.04 μM).
Anti-inflammatory isocoumarins from the bark of Fraxinus chinensis subsp. rhynchophylla
Lee, Beom Zoo,Kim, Chan-Sik,Jeong, Soon-Kyu,Lee, Sulhae,Lee, Ik Soo,Hong, KwangWon
, p. 4380 - 4387 (2021)
A new isocoumarin (1) named fraxicoumarin was isolated from the bark of Fraxinus chinensis subsp. rhynchophylla along with three known compounds (2–4). The structure of the new compound was established by extensive spectroscopic studies and chemical evidence. The anti-inflammatory effects of the isolated compounds (1–4) on lipopolysaccharide (LPS)-induced RAW 264.7 macrophage cells were evaluated in?vitro. Of the compounds tested, compounds 1 and 3 inhibited LPS-induced nitric oxide (NO) production in RAW 264.7 cells. Consistent with these findings, they also suppressed LPS-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) at the protein level in RAW 264.7 cells.
Diarylheptanoid sulfates and related compounds from myrica rubra bark
Yoshimura, Morio,Yamakami, Saori,Amakura, Yoshiaki,Yoshida, Takashi
, p. 1798 - 1802 (2012)
Three new diarylheptanoids, myricanol 11-sulfate (1), juglanin B 11-sulfate (2), and myricanone 5-O-(6′-O-galloyl)glucoside (3), were isolated from the bark of Myrica rubra. Compounds 1 and 2 were characterized as diarylheptanoid sulfates on the basis of spectroscopic analyses. The antioxidative activities of the fractionated extracts and isolated compounds were estimated by the oxygen radical absorbance capacity (ORAC) and superoxide dismutase (SOD)-like activity assays. The major isolate, myricitrin (4), displayed a high ORAC value and moderate SOD-like activity (13 198 μmol TE (Trolox equivalent)/g and IC50 127.5 μg/mL, respectively), which might explain the potent antioxidative activity of this material.
New ellagitannin and galloyl esters of phenolic glycosides from sapwood of Quercus mongolica var. crispula (Japanese oak)
Omar, Mohamed,Matsuo, Yosuke,Maeda, Hajime,Saito, Yoshinori,Tanaka, Takashi
, p. 486 - 490 (2013)
Two novel glycosides, 4,5-dimethoxy-3-hydroxyphenol 1-O-β-(6′-O- galloyl)-glucopyranoside (1) and (+)-2α-O-galloyl lyoniresinol 3α-O-β-D-xylopyranoside (2), as well as a novel ellagitannin named epiquisqualin B (3), were isolated from sapwood of Quercus mongolica var. crispula along with 19 known phenolic compounds. The structures of the novel compounds were elucidated on the basis of chemical and spectroscopic investigation. Compound 2 is the first example of a lignan galloyl ester, and 3 is the oxidation product of vescalagin, which is the major ellagitannin of this plant.
Tamarixellagic acid, an ellagitannin from the galls of Tamarix aphylla
Nawwar,Hussein,Buddrus,Linscheid
, p. 1349 - 1354 (1994)
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ISOLATION OF NORBERGENIN FROM SAXIFRAGA STOLONIFERA
Taneyama, Masatoshi,Yoshida, Seiichi,Kobayashi, Michio,Hasegawa, Masao
, p. 1053 - 1054 (1983)
Key Word Index - Saxifraga stolonifera; Saxifragaceae; desmethylbergenin; norbergenin; bergenin; tri-O-methyl-norbergenin. Norbergenin, a C-glucoside, was isolated from Saxifraga stolonifera and its structure assigned as 2β-D-glucopyranosylgallic acid δ-lactone.
Tannins of tamaricaceous plants. III. New dimeric hydrolyzable tannins from Reaumuria hirtella
Yoshida,Ahmed,Okuda
, p. 672 - 679 (1993)
Four new dimeric hydrolyzable tannins, hirtellins C, D, E and F, besides previously reported hirtellins A and B, have been isolated from the leaf extract of Reaumuria hirtella Jaub. et Sp. (Tamaricaceae). Macrocyclic structures, 1 and 12, having both dehydrodigalloyl (DHDG) and isodehydrodigalloyl (isoDHDG) groups as the connecting units between monomers, were respectively assigned for hirtellin C and F, based on chemical methods, two-dimensional nuclear magnetic resonance measurement and other spectroscopic analyses. Hirtellin D (7) was characterized as an isomer of hirtellin F (12). Hirtellin E (15), having a dehydrotrigalloyl (hellinoyl) group, was characterized as an analog of hirtellin B.
Barth
, p. 1484 Anm. (1875)
Analysis of phenolic compounds in health care products by low-pressure liquid-chromatography with monolithic column and chemiluminescent detection
Ballesta-Claver,Valencia,Capitan-Vallvey
, p. 44 - 53 (2011)
This paper presents a new application for monolithic columns with low-pressure chromatographic separation using an flow injection analysis configuration with chemiluminescent detection for the determination of a mixture of phenolic compounds: phloroglucinol, 2,4-dihydroxybenzoic acid, salicylic acid, methyl paraben and n-propyl gallate. The procedure consists of the separation of these compounds on a reverse-phase ultra-short monolithic column with pH 3.0 acetate buffer and 5% acetonitrile as carrier phase. The detection is based on a chemiluminescence measurement coming from Ce(IV) - Rhodamine 6G chemistry with the incorporation of two different chemiluminescent chemical conditions in the chromatographic setup in order to enhance the sensitivity for the different phenolic compounds. All separation and detection variables were optimized to propose a determination method. The analysis is performed in 280 s, with the sampling frequency being some 13 h-1. The calibration function is a double reciprocal function obtaining good results within two orders of magnitude. The limits of detection were 8.8 × 10-8 M (phloroglucinol), 2.7 × 10-8 M (2,4-dihydroxybenzoic acid); 2.3 × 10-8 M (salicylic acid); 5.2 × 10-8 M (methyl paraben) and 4.1 × 10-6 M (n-propyl gallate), and the relative standard deviations at a medium level of the linear range were 4.4% (phloroglucinol), 2.8% (2,4-dihydroxybenzoic acid), 5.2% (salicylic acid), 3.6% (methyl paraben) and 6.8% (n-propyl gallate). The method was applied and validated satisfactorily for the determination of these compounds in healthcare products, comparing the results against an HPLC reference method. Copyright
Fatty acid synthase inhibitors from Geum japonicum Thunb. var. chinense
Liu, Hongwei,Li, Jiankuan,Zhao, Wenhua,Bao, Li,Song, Xiaohong,Xia, Ying,Wang, Xue,Zhang, Chao,Wang, Xiaozhu,Yao, Xinsheng,Li, Ming
, p. 402 - 410 (2009)
Bioassay-guided fractionation of the MeOH extract of Geum japonicum THUNB. var. chinense using the fatty acid synthase inhibition assay led to the isolation of a new dimeric ellagitannin, gemin G (1), together with six known compounds, gemin A (2), casuar
Study on in Vitro Preparation and Taste Properties of N-Ethyl-2-Pyrrolidinone-Substituted Flavan-3-Ols
Han, Zisheng,Ho, Chi-Tang,Jiang, Zongde,Lai, Guoping,Qin, Chunyin,Wan, Xiaochun,Wen, Mingchun,Zhai, Xiaoting,Zhang, Hui,Zhang, Liang
, (2022/04/07)
N-ethyl-2-pyrrolidinone-substituted flavan-3-ols (EPSFs) were prepared by an in vitro model reaction, and the taste thresholds of EPSFs and their dose-over-threshold factors in large-leaf yellow tea (LYT) were investigated. The effects of initial reactant