NCBI Taxonomy: 1006121
Tetrastigma hemsleyanum (ncbi_taxid: 1006121)
found 18 associated metabolites at species taxonomy rank level.
Ancestor: Tetrastigma
Child Taxonomies: none taxonomy data.
Indole
Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. The participation of the nitrogen lone electron pair in the aromatic ring means that indole is not a base, and it does not behave like a simple amine. Indole is a microbial metabolite and it can be produced by bacteria as a degradation product of the amino acid tryptophan. It occurs naturally in human feces and has an intense fecal smell. At very low concentrations, however, indole has a flowery smell and is a constituent of many flower scents (such as orange blossoms) and perfumes. As a volatile organic compound, indole has been identified as a fecal biomarker of Clostridium difficile infection (PMID: 30986230). Natural jasmine oil, used in the perfume industry, contains around 2.5\\\\\% of indole. Indole also occurs in coal tar. Indole has been found to be produced in a number of bacterial genera including Alcaligenes, Aspergillus, Escherichia, and Pseudomonas (PMID: 23194589, 2310183, 9680309). Indole plays a role in bacterial biofilm formation, bacterial motility, bacterial virulence, plasmid stability, and antibiotic resistance. It also functions as an intercellular signalling molecule (PMID: 26115989). Recently, it was determined that the bacterial membrane-bound histidine sensor kinase (HK) known as CpxA acts as a bacterial indole sensor to facilitate signalling (PMID: 31164470). It has been found that decreased indole concentrations in the gut promote bacterial pathogenesis, while increased levels of indole in the gut decrease bacterial virulence gene expression (PMID: 31164470). As a result, enteric pathogens sense a gradient of indole concentrations in the gut to migrate to different niches and successfully establish an infection. Constituent of several flower oils, especies of Jasminum and Citrus subspecies (Oleaceae) production of bacterial dec. of proteins. Flavouring ingredientand is also present in crispbread, Swiss cheese, Camembert cheese, wine, cocoa, black and green tea, rum, roasted filbert, rice bran, clary sage, raw shrimp and other foodstuffs Indole. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=120-72-9 (retrieved 2024-07-16) (CAS RN: 120-72-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Indole is an endogenous metabolite. Indole is an endogenous metabolite.
3-Indolepropionic acid
3-Indolepropionic acid is shown to be a powerful antioxidant and has potential in the treatment for Alzheimer’s disease.
Indole-3-propionic acid
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.
1-O-Caffeoylquinic acid
1-O-Caffeoylquinic acid is found in coffee and coffee products. 1-O-Caffeoylquinic acid is a constituent of coffee 1-Caffeoylquinic acid is an effective NF-κB inhibitor, shows significant binding affinity to the RH domain of p105 with Ki of 0.002 μM and binding energy of 1.50 Kcal/mol[1]. 1-Caffeoylquinic acid has anti-oxidative stress ability[2]. 1-Caffeoylquinic acid inhibits PD-1/PD-L1 interact[3]. 1-Caffeoylquinic acid is an effective NF-κB inhibitor, shows significant binding affinity to the RH domain of p105 with Ki of 0.002 μM and binding energy of 1.50 Kcal/mol[1]. 1-Caffeoylquinic acid has anti-oxidative stress ability[2]. 1-Caffeoylquinic acid inhibits PD-1/PD-L1 interact[3].
indol
Indole is an endogenous metabolite. Indole is an endogenous metabolite.