Epicatechin Gallate
Formula: C22H18O10 (442.09)
Chinese Name: (-)-表儿茶素没食子酸酯, 表儿茶素没食子酸酯, 表儿茶精没食子酸酯
BioDeep ID: BioDeep_00000017213
( View LC/MS Profile)
SMILES: C1(O)C=C2O[C@H](C3C=C(O)C(O)=CC=3)[C@H](OC(C3C=C(O)C(O)=C(O)C=3)=O)CC2=C(O)C=1
Found 37 Sample Hits
m/z | Adducts | Species | Organ | Scanning | Sample | |
---|---|---|---|---|---|---|
407.0794 | [M+H-2H2O]+PPM:8 |
Plant | Root | MALDI (DHB) |
MPIMM_035_QE_P_PO_6pm - MPIMM_035_QE_P_PO_6pmResolution: 30μm, 165x170
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407.0738 | [M+H-2H2O]+PPM:5.7 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_91_1 - Grape DatabaseResolution: 50μm, 120x114
Grape berries fruit, condition: Ripe |
|
425.0844 | [M+H-H2O]+PPM:5.4 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_91_1 - Grape DatabaseResolution: 50μm, 120x114
Grape berries fruit, condition: Ripe |
|
442.0826 | [M]+PPM:15.5 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_91_1 - Grape DatabaseResolution: 50μm, 120x114
Grape berries fruit, condition: Ripe |
|
443.095 | [M+H]+PPM:5.1 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_91_1 - Grape DatabaseResolution: 50μm, 120x114
Grape berries fruit, condition: Ripe |
|
465.0769 | [M+Na]+PPM:5 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_91_1 - Grape DatabaseResolution: 50μm, 120x114
Grape berries fruit, condition: Ripe |
|
407.0738 | [M+H-2H2O]+PPM:5.7 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_164_1 - Grape DatabaseResolution: 17μm, 136x122
Grape berries fruit, condition: Late |
|
425.0844 | [M+H-H2O]+PPM:5.4 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_164_1 - Grape DatabaseResolution: 17μm, 136x122
Grape berries fruit, condition: Late |
|
442.0826 | [M]+PPM:15.5 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_164_1 - Grape DatabaseResolution: 17μm, 136x122
Grape berries fruit, condition: Late |
|
465.0768 | [M+Na]+PPM:5.2 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_164_1 - Grape DatabaseResolution: 17μm, 136x122
Grape berries fruit, condition: Late |
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407.0738 | [M+H-2H2O]+PPM:5.7 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_163_1 - Grape DatabaseResolution: 17μm, 132x115
Grape berries fruit, condition: Late |
|
425.0844 | [M+H-H2O]+PPM:5.4 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_163_1 - Grape DatabaseResolution: 17μm, 132x115
Grape berries fruit, condition: Late |
|
442.0827 | [M]+PPM:15.3 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_163_1 - Grape DatabaseResolution: 17μm, 132x115
Grape berries fruit, condition: Late |
|
443.095 | [M+H]+PPM:5.1 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_163_1 - Grape DatabaseResolution: 17μm, 132x115
Grape berries fruit, condition: Late |
|
465.0768 | [M+Na]+PPM:5.2 |
Vitis vinifera | Fruit | MALDI (DHB) |
grape_dhb_163_1 - Grape DatabaseResolution: 17μm, 132x115
Grape berries fruit, condition: Late |
|
407.0728 | [M+H-2H2O]+PPM:8.2 |
Mus musculus | Lung | MALDI (DHB) |
image3 - MTBLS2075Resolution: 40μm, 146x190
Fig. 4 MALDI-MSI data of mouse lung tissue after administration with D9-choline and U13C-DPPC–containing Poractant alfa surfactant (labels administered 12 h prior to tissue collection). Ion images of (A) m/z 796.6856 ([U13C-DPPC+Na]+), (B) m/z 756.5154 [PC32:0+Na]+), and (C) m/z 765.6079 ([D9-PC32:0+Na]+). D: Overlay image of [U13C-PC32:0+Na]+ (red) and [D9-PC32:0+Na]+ (green). Part-per-million (ppm) mass errors are indicated in parentheses. All images were visualized using total-ion-current normalization and using hotspot removal (high quantile = 99%). DPPC = PC16:0/16:0. MSI, mass spectrometry imaging; PC, phosphatidylcholine; U13C-DPPC, universally 13C-labeled dipalmitoyl PC. |
|
425.0835 | [M+H-H2O]+PPM:7.5 |
Mus musculus | Lung | MALDI (DHB) |
image3 - MTBLS2075Resolution: 40μm, 146x190
Fig. 4 MALDI-MSI data of mouse lung tissue after administration with D9-choline and U13C-DPPC–containing Poractant alfa surfactant (labels administered 12 h prior to tissue collection). Ion images of (A) m/z 796.6856 ([U13C-DPPC+Na]+), (B) m/z 756.5154 [PC32:0+Na]+), and (C) m/z 765.6079 ([D9-PC32:0+Na]+). D: Overlay image of [U13C-PC32:0+Na]+ (red) and [D9-PC32:0+Na]+ (green). Part-per-million (ppm) mass errors are indicated in parentheses. All images were visualized using total-ion-current normalization and using hotspot removal (high quantile = 99%). DPPC = PC16:0/16:0. MSI, mass spectrometry imaging; PC, phosphatidylcholine; U13C-DPPC, universally 13C-labeled dipalmitoyl PC. |
|
407.0728 | [M+H-2H2O]+PPM:8.2 |
Mus musculus | Lung | MALDI (DHB) |
image4 - MTBLS2075Resolution: 40μm, 162x156
Fig 6c
Fig. 6 MALDI-MSI of U13C-PC16:0/16:0 acyl chain remodeling. A: Averaged MALDI mass spectrum from lung tissue collected from mice euthanized 12 h after administration of D9-choline and U13C-DPPC–containing Poractant alfa surfactant. The ion at m/z 828.6321 is assigned as the [M+Na]+ ion of 13C24-PC16:0_20:4 formed by acyl remodeling of U13C-PC16:0/16:0. The “NL” value refers to the intensity of the base peak in the full range MS1 spectrum. B: MS/MS spectrum of precursor ions at m/z 828.5 ± 0.5 with fragment ions originating from [13C24-PC16:0_20:4+Na]+ annotated. Part-per-million (ppm) mass errors are provided in parentheses. C, D: MALDI-MSI data of [U13C-DPPC+Na]+ (blue), [PC36:4+Na]+ (green) and [13C24-PC16:0_20:4+Na]+ (red) in lung tissue collected from mice (C) 12 h and (D) 18 h after label administration. All images were visualized using total-ion-current normalization and hotspot removal (high quantile = 99%). MS/MS, tandem mass spectrometry; MSI, mass spectrometry imaging; PC, phosphatidylcholine; U13C-DPPC, universally 13C-labeled dipalmitoyl PC. |
|
425.0834 | [M+H-H2O]+PPM:7.8 |
Mus musculus | Lung | MALDI (DHB) |
image4 - MTBLS2075Resolution: 40μm, 162x156
Fig 6c
Fig. 6 MALDI-MSI of U13C-PC16:0/16:0 acyl chain remodeling. A: Averaged MALDI mass spectrum from lung tissue collected from mice euthanized 12 h after administration of D9-choline and U13C-DPPC–containing Poractant alfa surfactant. The ion at m/z 828.6321 is assigned as the [M+Na]+ ion of 13C24-PC16:0_20:4 formed by acyl remodeling of U13C-PC16:0/16:0. The “NL” value refers to the intensity of the base peak in the full range MS1 spectrum. B: MS/MS spectrum of precursor ions at m/z 828.5 ± 0.5 with fragment ions originating from [13C24-PC16:0_20:4+Na]+ annotated. Part-per-million (ppm) mass errors are provided in parentheses. C, D: MALDI-MSI data of [U13C-DPPC+Na]+ (blue), [PC36:4+Na]+ (green) and [13C24-PC16:0_20:4+Na]+ (red) in lung tissue collected from mice (C) 12 h and (D) 18 h after label administration. All images were visualized using total-ion-current normalization and hotspot removal (high quantile = 99%). MS/MS, tandem mass spectrometry; MSI, mass spectrometry imaging; PC, phosphatidylcholine; U13C-DPPC, universally 13C-labeled dipalmitoyl PC. |
|
407.0733 | [M+H-2H2O]+PPM:7 |
Mus musculus | Lung | MALDI (DHB) |
image5 - MTBLS2075Resolution: 40μm, 163x183
Supplementary Figure S8. MALDI-MSI data of mouse lung tissue administered with D9-choline and
U 13C-DPPC–containing Poractant alfa surfactant (labels administered 18 h prior to sacrifice). Ion
images of (a) m/z 796.6856 ([U13C-DPPC+Na]+), (b) m/z 756.5154 [PC32:0+Na]+ and (c) m/z 765.6079
([D9-PC32:0+Na]+). (d) Overlay image of [U13C-DPPC+Na]+ (red) and [D9-PC32:0+Na]+ (green).
Parts per million (ppm) mass errors are indicated in parentheses. All images were visualised using totalion-current normalisation and using hotspot removal (high quantile = 99%). DPPC = PC16:0/16:0. |
|
425.0837 | [M+H-H2O]+PPM:7.1 |
Mus musculus | Lung | MALDI (DHB) |
image5 - MTBLS2075Resolution: 40μm, 163x183
Supplementary Figure S8. MALDI-MSI data of mouse lung tissue administered with D9-choline and
U 13C-DPPC–containing Poractant alfa surfactant (labels administered 18 h prior to sacrifice). Ion
images of (a) m/z 796.6856 ([U13C-DPPC+Na]+), (b) m/z 756.5154 [PC32:0+Na]+ and (c) m/z 765.6079
([D9-PC32:0+Na]+). (d) Overlay image of [U13C-DPPC+Na]+ (red) and [D9-PC32:0+Na]+ (green).
Parts per million (ppm) mass errors are indicated in parentheses. All images were visualised using totalion-current normalisation and using hotspot removal (high quantile = 99%). DPPC = PC16:0/16:0. |
|
407.0789 | [M+H-2H2O]+PPM:6.8 |
Posidonia oceanica | root | MALDI (CHCA) |
20190614_MS1_A19r-20 - MTBLS1746Resolution: 17μm, 262x276
Seagrasses are one of the most efficient natural sinks of carbon dioxide (CO2) on Earth. Despite covering less than 0.1% of coastal regions, they have the capacity to bury up to 10% of marine organic matter and can bury the same amount of carbon 35 times faster than tropical rainforests. On land, the soil’s ability to sequestrate carbon is intimately linked to microbial metabolism. Despite the growing attention to the link between plant production, microbial communities, and the carbon cycle in terrestrial ecosystems, these processes remain enigmatic in the sea. Here, we show that seagrasses excrete organic sugars, namely in the form of sucrose, into their rhizospheres. Surprisingly, the microbial communities living underneath meadows do not fully use this sugar stock in their metabolism. Instead, sucrose piles up in the sediments to mM concentrations underneath multiple types of seagrass meadows. Sediment incubation experiments show that microbial communities living underneath a meadow use sucrose at low metabolic rates. Our metagenomic analyses revealed that the distinct community of microorganisms occurring underneath meadows is limited in their ability to degrade simple sugars, which allows these compounds to persist in the environment over relatively long periods of time. Our findings reveal how seagrasses form blue carbon stocks despite the relatively small area they occupy. Unfortunately, anthropogenic disturbances are threatening the long-term persistence of seagrass meadows. Given that these sediments contain a large stock of sugars that heterotopic bacteria can degrade, it is even more important to protect these ecosystems from degradation. |
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407.0786 | [M+H-2H2O]+PPM:6 |
Posidonia oceanica | root | MALDI (CHCA) |
20190822_MS1_A19r-19 - MTBLS1746Resolution: 17μm, 303x309
Seagrasses are among the most efficient sinks of carbon dioxide on Earth. While carbon sequestration in terrestrial plants is linked to the microorganisms living in their soils, the interactions of seagrasses with their rhizospheres are poorly understood. Here, we show that the seagrass, Posidonia oceanica excretes sugars, mainly sucrose, into its rhizosphere. These sugars accumulate to µM concentrations—nearly 80 times higher than previously observed in marine environments. This finding is unexpected as sugars are readily consumed by microorganisms. Our experiments indicated that under low oxygen conditions, phenolic compounds from P. oceanica inhibited microbial consumption of sucrose. Analyses of the rhizosphere community revealed that many microbes had the genes for degrading sucrose but these were only expressed by a few taxa that also expressed genes for degrading phenolics. Given that we observed high sucrose concentrations underneath three other species of marine plants, we predict that the presence of plant-produced phenolics under low oxygen conditions allows the accumulation of labile molecules across aquatic rhizospheres. |
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407.0794 | [M+H-2H2O]+PPM:8 |
Posidonia oceanica | root | MALDI (CHCA) |
20190613_MS1_A19r-18 - MTBLS1746Resolution: 17μm, 246x264
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407.0793 | [M+H-2H2O]+PPM:7.8 |
Posidonia oceanica | root | MALDI (CHCA) |
20190828_MS1_A19r-22 - MTBLS1746Resolution: 17μm, 292x279
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442.0893 | [M]+PPM:0.3 |
Posidonia oceanica | root | MALDI (CHCA) |
20190828_MS1_A19r-22 - MTBLS1746Resolution: 17μm, 292x279
|
|
407.078 | [M+H-2H2O]+PPM:4.6 |
Posidonia oceanica | root | MALDI (CHCA) |
MS1_20180404_PO_1200 - MTBLS1746Resolution: 17μm, 193x208
|
|
425.0861 | [M+H-H2O]+PPM:1.4 |
Posidonia oceanica | root | MALDI (CHCA) |
MS1_20180404_PO_1200 - MTBLS1746Resolution: 17μm, 193x208
|
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442.1133 | [M-H2O+NH4]+PPM:0.1 |
Posidonia oceanica | root | MALDI (CHCA) |
MS1_20180404_PO_1200 - MTBLS1746Resolution: 17μm, 193x208
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465.0791 | [M+Na]+PPM:0.2 |
Posidonia oceanica | root | MALDI (CHCA) |
MS1_20180404_PO_1200 - MTBLS1746Resolution: 17μm, 193x208
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407.0807 | [M+H-2H2O]+PPM:11.2 |
Mus musculus | Liver | MALDI (CHCA) |
Salmonella_final_pos_recal - MTBLS2671Resolution: 17μm, 691x430
A more complete and holistic view on host–microbe interactions is needed to understand the physiological and cellular barriers that affect the efficacy of drug treatments and allow the discovery and development of new therapeutics. Here, we developed a multimodal imaging approach combining histopathology with mass spectrometry imaging (MSI) and same section imaging mass cytometry (IMC) to study the effects of Salmonella Typhimurium infection in the liver of a mouse model using the S. Typhimurium strains SL3261 and SL1344. This approach enables correlation of tissue morphology and specific cell phenotypes with molecular images of tissue metabolism. IMC revealed a marked increase in immune cell markers and localization in immune aggregates in infected tissues. A correlative computational method (network analysis) was deployed to find metabolic features associated with infection and revealed metabolic clusters of acetyl carnitines, as well as phosphatidylcholine and phosphatidylethanolamine plasmalogen species, which could be associated with pro-inflammatory immune cell types. By developing an IMC marker for the detection of Salmonella LPS, we were further able to identify and characterize those cell types which contained S. Typhimurium.
[dataset] Nicole Strittmatter. Holistic Characterization of a Salmonella Typhimurium Infection Model Using Integrated Molecular Imaging, metabolights_dataset, V1; 2022. https://www.ebi.ac.uk/metabolights/MTBLS2671. |
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425.0802 | [M+H-H2O]+PPM:15.3 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
80TopL, 50TopR, 70BottomL, 60BottomR-profile - MTBLS415Resolution: 17μm, 137x136
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
|
460.1238 | [M+NH4]+PPM: |
Mytilus edulis | mantle | MALDI (DHB) |
20190201_MS38_Crassostrea_Mantle_350-1500_DHB_pos_A28_10um_270x210 - MTBLS2960Resolution: 10μm, 270x210
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460.123 | [M+NH4]+PPM:1.8 |
Mytilus edulis | gill | MALDI (DHB) |
20190202_MS38_Crassostrea_Gill_350-1500_DHB_pos_A25_11um_305x210 - MTBLS2960Resolution: 11μm, 305x210
single cell layer |
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460.1231 | [M+NH4]+PPM:1.6 |
Mytilus edulis | mantle | MALDI (DHB) |
20190216_MS38_Mytilus_mantle_350-1500_DHB_pos_A26_10um_275x210 - MTBLS2960Resolution: 10μm, 275x210
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425.0873 | [M+H-H2O]+PPM:1.4 |
Homo sapiens | colorectal adenocarcinoma | DESI () |
520TopL, 490TopR, 510BottomL, 500BottomR-profile - MTBLS415Resolution: 17μm, 147x131
The human colorectal adenocarcinoma sample was excised during a surgical operation performed at the Imperial College Healthcare NHS Trust. The sample and procedures were carried out in accordance with ethical approval (14/EE/0024). |
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442.0907 | [M]+PPM:2.8 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_8 - MTBLS385Resolution: 75μm, 69x61
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(-)-epicatechin-3-O-gallate is a gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida. It has a role as a metabolite, an EC 3.2.1.1 (alpha-amylase) inhibitor and an EC 3.2.1.20 (alpha-glucosidase) inhibitor. It is a catechin, a gallate ester and a polyphenol. It is functionally related to a (-)-epicatechin and a gallic acid. (-)-Epicatechin gallate is a natural product found in Scurrula atropurpurea, Acacia omalophylla, and other organisms with data available. Isolated from tea and numerous other plant subspecies inc. rhubarb and grapes. Epicatechin 3-gallate is found in many foods, some of which are cucumber, muskmelon, black raspberry, and cashew nut. A gallate ester obtained by formal condensation of the carboxy group of gallic acid with the (3R)-hydroxy group of epicatechin. A natural product found in Parapiptadenia rigida. (-)-Epicatechin 3-O-gallate is found in almond. (-)-Epicatechin 3-O-gallate is isolated from tea and numerous other plant species including rhubarb and grapes. D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors D020011 - Protective Agents > D000975 - Antioxidants D000970 - Antineoplastic Agents (-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM. (-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM. (-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM. (-)-Epicatechin gallate (Epicatechin gallate) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 7.5 μM.