Indole-3-propionic acid
Formula: C11H11NO2 (189.079)
Chinese Name: 3-吲哚丙酸(IPA), 3-吲哚丙酸
BioDeep ID: BioDeep_00000018442
( View LC/MS Profile)
SMILES: C1=CC=C2C(=C1)C(=CN2)CCC(=O)O
Found 11 Sample Hits
m/z | Adducts | Species | Organ | Scanning | Sample | |
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189.1058 | [M-H2O+NH4]+PPM:18.9 |
Marker Pen | NA | DESI (None) |
3ul_0.8Mpa_RAW_20241016-PAPER PNMK - MEMI_testResolution: 30μm, 315x42
By writing the four English letters “PNMK” on white paper with a marker pen, and then scanning with a DESI ion source to obtain the scanning result. The signal of the chemical substances on the marker pen used appears on the channel with an m/z value of |
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207.1146 | [M+NH4]+PPM:8.7 |
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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207.116 | [M+NH4]+PPM:15.5 |
Posidonia oceanica | root | MALDI (CHCA) |
20190613_MS1_A19r-18 - MTBLS1746Resolution: 17μm, 246x264
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172.0762 | [M+H-H2O]+PPM:3 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_4 - MTBLS385Resolution: 17μm, 82x80
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189.0774 | [M]+PPM:5.4 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_4 - MTBLS385Resolution: 17μm, 82x80
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189.1027 | [M-H2O+NH4]+PPM:2.5 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_4 - MTBLS385Resolution: 17μm, 82x80
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207.1133 | [M+NH4]+PPM:2.4 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_4 - MTBLS385Resolution: 17μm, 82x80
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190.0845 | [M+H]+PPM:9.2 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_2 - MTBLS385Resolution: 17μm, 95x101
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190.0844 | [M+H]+PPM:9.7 |
Homo sapiens | esophagus | DESI () |
LNTO29_16_3 - MTBLS385Resolution: 17μm, 108x107
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190.0848 | [M+H]+PPM:7.6 |
Homo sapiens | esophagus | DESI () |
LNTO22_1_7 - MTBLS385Resolution: 75μm, 69x54
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190.0844 | [M+H]+PPM:9.7 |
Homo sapiens | esophagus | DESI () |
LNTO29_18_2 - MTBLS385Resolution: 75μm, 62x68
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Indole-3-propionic acid (IPA, indole-3-propionate, or indole propionic acid), is a reductive product of tryptophan formed by bacteria in the gastrointestinal tract of mammals and birds (PMID:29168502). It is endogenously produced by human microbiota and has only been detected in vivo (PMID:19234110). While many microbial metabolites produced in the gut are toxic or act as uremic toxins (when they are reabsorbed through the gut epithelia), indole-3-propionic acid is a very beneficial microbial metabolite (PMID:30914514, 30862081, 29238104). In limited studies, urinary IPA correlates positively with disease and it remains unclear if this represents host bacteria responding to pathology via the production of IPA, or intestinal permeability changes leading to higher absorption and excretion of IPA, or inflammatory changes within kidneys leading to high excretion of IPA (PMID:32132996). Indole-3-propionic acid is a remarkably strong antioxidant (PMID:10721080). It is an even more potent scavenger of hydroxyl radicals than melatonin, the most potent scavenger of hydroxyl radicals synthesized by the human body. Similar to melatonin but unlike other antioxidants, indole-3-propionic acid scavenges radicals without subsequently generating reactive and pro-oxidant intermediate compounds (PMID:9928448, 10419516). Indole-3-propionic acid has been shown to prevent oxidative stress and the death of primary neurons and neuroblastoma cells exposed to the amyloid beta-protein in the form of amyloid fibrils, one of the most prominent neuropathologic features of Alzheimers disease. 3-Indolepropionic acid also shows a strong level of neuroprotection in two other paradigms of oxidative stress. (PMID 10419516) More recently it has been found that higher indole-3-propionic acid levels in serum/plasma are associated with a reduced likelihood of type 2 diabetes and with higher levels of consumption of fibre-rich foods (PMID:28397877). Studies have shown that serum levels of indole-3-propionic acid are positively correlated with dietary fibre intake and negatively correlated with C-reactive protein levels (PMID:29795366). Indole-3-propionic acid is a marker for the presence of Clostridium sporogenes in the gut. Higher levels are associated with higher levels of Clostridium sporogenes (PMID:7378938). In addition to its useful physiological role in mammals, indole-3-propionic acid is a plant hormone with functions similar to indole-3-acetic acid (or IAA), the major plant auxin. Recent studies have shed some light on additional mechanisms of action of IPA. In the intestine, IPA could serve as a ligand to an adopted orphan nuclear receptor, Pregnane X receptor (PXR) and act as an anti-inflammatory agent (PMID:25065623). This property has allowed investigators to develop more potent analogs targeting PXR (PMID:32153125). Other tissues may also be targeted by IPA in a similar manner (PMID:31211619). Indole-3-propionate (IPA), a deamination product of tryptophan formed by symbiotic bacteria in the gastrointestinal tract of mammals and birds. 3-Indolepropionic acid has been shown to prevent oxidative stress and death of primary neurons and neuroblastoma cells exposed to the amyloid beta-protein in the form of amyloid fibrils, one of the most prominent neuropathologic features of Alzheimers disease. 3-Indolepropionic acid also shows a strong level of neuroprotection in two other paradigms of oxidative stress. (PMID: 10419516) [HMDB]. 1H-Indole-3-propanoic acid is found in common pea. 3-Indolepropionic acid is shown to be a powerful antioxidant and has potential in the treatment for Alzheimer’s disease.