“3-Indolepropionic acid”的意思、由来-开放百科全书

IPA is an even more potent scavenger of hydroxyl radicals than melatonin, the most potent scavenger of hydroxyl radicals that is synthesized by human enzymes. Similar to melatonin but unlike other antioxidants, it scavenges radicals without subsequently generating reactive and pro-oxidant intermediate compounds.^[4] In 2017, elevated concentrations of IPA in human blood plasma were found to be correlated with a lower risk of type 2 diabetes and higher consumption of fiber-rich foods.^[5]^[6]

Biosynthesis in humans and cellular effects

Metabolism

IPA can be converted in the liver or kidneys to 3-indoleacrylic acid, which is subsequently conjugated with glycine, forming indolylacryloyl glycine.^[7]

History

The neuroprotective, antioxidant, and anti-amyloid properties of IPA were first reported by a group of investigators in July 1999, led by Dr Pappolla and Dr. Poeggeler at the University of South Alabama.^[8]^[9]^[10]

See also

References

1. ^{{cite journal | vauthors = Galligan JJ | title = Beneficial actions of microbiota-derived tryptophan metabolites | journal = Neurogastroenterology & Motility | volume = 30 | issue = 2 | pages = e13283| date = February 2018 | pmid = 29341448 | doi = 10.1111/nmo.13283 | url = }}
2. ^¹{{cite journal | vauthors = Bendheim PE, Poeggeler B, Neria E, Ziv V, Pappolla MA, Chain DG | title = Development of indole-3-propionic acid (OXIGON) for Alzheimer's disease | journal = J. Mol. Neurosci. | volume = 19 | issue = 1–2 | pages = 213–217 | date = October 2002 | pmid = 12212784 | doi = 10.1007/s12031-002-0036-0| quote = The accumulation of amyloid-beta and concomitant oxidative stress are major pathogenic events in Alzheimer's disease. Indole-3-propionic acid (IPA, OXIGON) is a potent anti-oxidant devoid of pro-oxidant activity. IPA has been demonstrated to be an inhibitor of beta-amyloid fibril formation and to be a potent neuroprotectant against a variety of oxidotoxins. This review will summarize the known properties of IPA and outline the rationale behind its selection as a potential disease-modifying therapy for Alzheimer's disease.}}
3. ^¹{{cite journal | vauthors = Attwood G, Li D, Pacheco D, Tavendale M | title = Production of indolic compounds by rumen bacteria isolated from grazing ruminants | journal = J. Appl. Microbiol. | volume = 100 | issue = 6 | pages = 1261–1271 | date = June 2006 | pmid = 16696673 | doi = 10.1111/j.1365-2672.2006.02896.x | url = }}
4. ^{{cite journal | vauthors = Reiter RJ, Guerrero JM, Garcia JJ, Acuña-Castroviejo D | title = Reactive oxygen intermediates, molecular damage, and aging. Relation to melatonin | journal = Ann. N. Y. Acad. Sci. | volume = 854 | issue = | pages = 410–424 | date = November 1998 | pmid = 9928448 | doi = 10.1111/j.1749-6632.1998.tb09920.x| url = }}
5. ^{{cite journal | vauthors = de Mello VD, Paananen J, Lindström J, Lankinen MA, Shi L, Kuusisto J, Pihlajamäki J, Auriola S, Lehtonen M, Rolandsson O, Bergdahl IA, Nordin E, Ilanne-Parikka P, Keinänen-Kiukaanniemi S, Landberg R, Eriksson JG, Tuomilehto J, Hanhineva K, Uusitupa M | title = Indolepropionic acid and novel lipid metabolites are associated with a lower risk of type 2 diabetes in the Finnish Diabetes Prevention Study | journal = Scientific Reports | volume = 7 | issue = | pages = 46337 | date = April 2017 | pmid = 28397877 | pmc = 5387722 | doi = 10.1038/srep46337 | url = }}
6. ^{{cite journal | vauthors = Tuomainen M, Lindström J, Lehtonen M, Auriola S, Pihlajamäki J, Peltonen M, Tuomilehto J, Uusitupa M, de Mello VD, Hanhineva K | title = Associations of serum indolepropionic acid, a gut microbiota metabolite, with type 2 diabetes and low-grade inflammation in high-risk individuals | journal = Nutrition & Diabetes | volume = 8 | issue = 1 | pages = 35 | date = May 2018 | pmid = 29795366 | pmc = 5968030 | doi = 10.1038/s41387-018-0046-9 | url = }}
7. ^{{cite journal | vauthors = Keszthelyi D, Troost FJ, Masclee AA | title = Understanding the role of tryptophan and serotonin metabolism in gastrointestinal function | journal = Neurogastroenterology & Motility | volume = 21 | issue = 12 | pages = 1239–49 | date = December 2009 | pmid = 19650771 | doi = 10.1111/j.1365-2982.2009.01370.x | quote = Indolylpropionic acid can be further converted in the liver or kidney into indolyl acrylic acid (IAcrA) and conjugated with glycine to produce indolylacryloyl glycine (IAcrGly). ... Also, indolyl propionic acid has been shown to be a powerful antioxidant, and is currently being investigated as a possible treatment for Alzheimers disease.⁴⁰}}
8. ^{{cite journal | vauthors = Poeggeler B, Sambamurti K, Siedlak SL, Perry G, Smith MA, Pappolla MA | title = A novel endogenous indole protects rodent mitochondria and extends rotifer lifespan | journal = PLOS One | volume = 5 | issue = 4 | pages = e10206 | date = April 2010 | pmid = 20421998 | pmc = 2858081 | doi = 10.1371/journal.pone.0010206 | url = }}
9. ^{{cite journal | vauthors = Karbownik M, Reiter RJ, Garcia JJ, Cabrera J, Burkhardt S, Osuna C, Lewiński A | title = Indole-3-propionic acid, a melatonin-related molecule, protects hepatic microsomal membranes from iron-induced oxidative damage: relevance to cancer reduction | journal = Journal of Cellular Biochemistry | volume = 81 | issue = 3 | pages = 507–13 | date = 2001 | pmid = 11255233 | doi = 10.1002/1097-4644(20010601)81:3<507::AID-JCB1064>3.0.CO;2-M| url = }}
10. ^{{cite journal | vauthors = Reiter RJ, Tan DX, Osuna C, Gitto E | title = Actions of melatonin in the reduction of oxidative stress. A review | journal = Journal of Biomedical Science | volume = 7 | issue = 6 | pages = 444–58 | date = 2000 | pmid = 11060493 | doi = 10.1159/000025480 | url = }}
11. ^{{cite journal | vauthors = Behr C, Kamp H, Fabian E, Krennrich G, Mellert W, Peter E, Strauss V, Walk T, Rietjens IMCM, van Ravenzwaay B | title = Gut microbiome-related metabolic changes in plasma of antibiotic-treated rats | journal = Archives of Toxicology | volume = 91 | issue = 10 | pages = 3439–3454 | date = October 2017 | pmid = 28337503 | doi = 10.1007/s00204-017-1949-2 | url = }}

词条	3-Indolepropionic acid
释义	Biosynthesis in humans and cellular effects Metabolism History Research See also References {{Use dmy dates\|date=June 2018}}{{Update\|reason=recently published information on this compound from this^[1] review\|date=June 2018}}{{Infobox drug \| Watchedfields = \| Verifiedfields = \| verifiedrevid = 685380927 \| drug_name = 3-indolepropionic acid \| IUPAC_name = 3-(1H-Indol-3-yl)propanoic acid \| image = 3-Indolepropionic acid skeletal.svg \| width = \| alt = \| image2 = \| width2 = \| alt2 = \| caption = \| tradename =Oxigon^[2] \| legal_US = Unscheduled \| legal_US_comment = \| legal_UN = unscheduled \| legal_UN_comment = \| legal_status = \| routes_of_administration = \| bioavailability = \| protein_bound = \| metabolism = \| metabolites = \| onset = \| elimination_half-life = \| duration_of_action = \| excretion = \| CAS_number_Ref = {{cascite\|correct\|CAS}} \| DrugBank_Ref = {{drugbankcite\|correct\|drugbank}} \| KEGG_Ref = {{keggcite\|correct\|kegg}} \| ChemSpiderID_Ref = {{chemspidercite\|correct\|chemspider}} \| ChEBI_Ref = {{ebicite\|correct\|EBI}} \| CAS_number = 830-96-6 \| CAS_supplemental = \| ATC_prefix = none \| ATC_suffix = \| ATC_supplemental = \| PubChem = 3744 \| IUPHAR_ligand = 4709 \| DrugBank = \| ChemSpiderID = 3613 \| UNII = JF49U1Q7KN \| KEGG = \| ChEBI = 43580 \| ChEMBL = \| NIAID_ChemDB = \| synonyms = Conjugate acid: {{bull}}{{nowrap\|1H-Indole-3-propanoic acid}} {{bull}}{{nowrap\|Indole-3-propionic acid}} Conjugate base: {{bull}}{{nowrap\|Indole-3-propionate}} \| C=11 \| H=11 \| N=1 \| O=2 \| molecular_weight = 189.21054 g/mol \| SMILES = C1=CC=C2C(=C1)C(=CN2)CCC(=O)O \| StdInChI = 1S/C11H11NO2/c13-11(14)6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6H2,(H,13,14) \| StdInChI_comment = \| StdInChIKey = GOLXRNDWAUTYKT-UHFFFAOYSA-N \| density = \| melting_point = 134 \| melting_high = 135 \| melting_notes = \| boiling_point = \| boiling_notes = \| solubility = \| specific_rotation = \| sec_combustion = }}3-Indolepropionic acid (IPA), or indole-3-propionic acid, is a potent neuroprotective antioxidant, plant auxin, and natural product in humans that is being studied for therapeutic use in Alzheimer's disease.^[2] It is endogenously produced by human microbiota and has only been detected in vivo when the species Clostridium sporogenes is present in the gastrointestinal tract.^[3] {{As of\|April 2016}}, C. sporogenes, which uses tryptophan to synthesize indole and subsequently IPA, is the only species of bacteria known to synthesize IPA in vivo at levels which are subsequently detectable in the blood plasma of the host.^[3] IPA is an even more potent scavenger of hydroxyl radicals than melatonin, the most potent scavenger of hydroxyl radicals that is synthesized by human enzymes. Similar to melatonin but unlike other antioxidants, it scavenges radicals without subsequently generating reactive and pro-oxidant intermediate compounds.^[4] In 2017, elevated concentrations of IPA in human blood plasma were found to be correlated with a lower risk of type 2 diabetes and higher consumption of fiber-rich foods.^[5]^[6] Biosynthesis in humans and cellular effects {{Tryptophan metabolism by human microbiota\|align=left}}{{clear}} Metabolism IPA can be converted in the liver or kidneys to 3-indoleacrylic acid, which is subsequently conjugated with glycine, forming indolylacryloyl glycine.^[7] History The neuroprotective, antioxidant, and anti-amyloid properties of IPA were first reported by a group of investigators in July 1999, led by Dr Pappolla and Dr. Poeggeler at the University of South Alabama.^[8]^[9]^[10] See also Indolepropionamide References 1. ^{{cite journal \| vauthors = Galligan JJ \| title = Beneficial actions of microbiota-derived tryptophan metabolites \| journal = Neurogastroenterology & Motility \| volume = 30 \| issue = 2 \| pages = e13283\| date = February 2018 \| pmid = 29341448 \| doi = 10.1111/nmo.13283 \| url = }} 2. ^¹{{cite journal \| vauthors = Bendheim PE, Poeggeler B, Neria E, Ziv V, Pappolla MA, Chain DG \| title = Development of indole-3-propionic acid (OXIGON) for Alzheimer's disease \| journal = J. Mol. Neurosci. \| volume = 19 \| issue = 1–2 \| pages = 213–217 \| date = October 2002 \| pmid = 12212784 \| doi = 10.1007/s12031-002-0036-0\| quote = The accumulation of amyloid-beta and concomitant oxidative stress are major pathogenic events in Alzheimer's disease. Indole-3-propionic acid (IPA, OXIGON) is a potent anti-oxidant devoid of pro-oxidant activity. IPA has been demonstrated to be an inhibitor of beta-amyloid fibril formation and to be a potent neuroprotectant against a variety of oxidotoxins. This review will summarize the known properties of IPA and outline the rationale behind its selection as a potential disease-modifying therapy for Alzheimer's disease.}} 3. ^¹{{cite journal \| vauthors = Attwood G, Li D, Pacheco D, Tavendale M \| title = Production of indolic compounds by rumen bacteria isolated from grazing ruminants \| journal = J. Appl. Microbiol. \| volume = 100 \| issue = 6 \| pages = 1261–1271 \| date = June 2006 \| pmid = 16696673 \| doi = 10.1111/j.1365-2672.2006.02896.x \| url = }} 4. ^{{cite journal \| vauthors = Reiter RJ, Guerrero JM, Garcia JJ, Acuña-Castroviejo D \| title = Reactive oxygen intermediates, molecular damage, and aging. Relation to melatonin \| journal = Ann. N. Y. Acad. Sci. \| volume = 854 \| issue = \| pages = 410–424 \| date = November 1998 \| pmid = 9928448 \| doi = 10.1111/j.1749-6632.1998.tb09920.x\| url = }} 5. ^{{cite journal \| vauthors = de Mello VD, Paananen J, Lindström J, Lankinen MA, Shi L, Kuusisto J, Pihlajamäki J, Auriola S, Lehtonen M, Rolandsson O, Bergdahl IA, Nordin E, Ilanne-Parikka P, Keinänen-Kiukaanniemi S, Landberg R, Eriksson JG, Tuomilehto J, Hanhineva K, Uusitupa M \| title = Indolepropionic acid and novel lipid metabolites are associated with a lower risk of type 2 diabetes in the Finnish Diabetes Prevention Study \| journal = Scientific Reports \| volume = 7 \| issue = \| pages = 46337 \| date = April 2017 \| pmid = 28397877 \| pmc = 5387722 \| doi = 10.1038/srep46337 \| url = }} 6. ^{{cite journal \| vauthors = Tuomainen M, Lindström J, Lehtonen M, Auriola S, Pihlajamäki J, Peltonen M, Tuomilehto J, Uusitupa M, de Mello VD, Hanhineva K \| title = Associations of serum indolepropionic acid, a gut microbiota metabolite, with type 2 diabetes and low-grade inflammation in high-risk individuals \| journal = Nutrition & Diabetes \| volume = 8 \| issue = 1 \| pages = 35 \| date = May 2018 \| pmid = 29795366 \| pmc = 5968030 \| doi = 10.1038/s41387-018-0046-9 \| url = }} 7. ^{{cite journal \| vauthors = Keszthelyi D, Troost FJ, Masclee AA \| title = Understanding the role of tryptophan and serotonin metabolism in gastrointestinal function \| journal = Neurogastroenterology & Motility \| volume = 21 \| issue = 12 \| pages = 1239–49 \| date = December 2009 \| pmid = 19650771 \| doi = 10.1111/j.1365-2982.2009.01370.x \| quote = Indolylpropionic acid can be further converted in the liver or kidney into indolyl acrylic acid (IAcrA) and conjugated with glycine to produce indolylacryloyl glycine (IAcrGly). ... Also, indolyl propionic acid has been shown to be a powerful antioxidant, and is currently being investigated as a possible treatment for Alzheimers disease.⁴⁰}} 8. ^{{cite journal \| vauthors = Poeggeler B, Sambamurti K, Siedlak SL, Perry G, Smith MA, Pappolla MA \| title = A novel endogenous indole protects rodent mitochondria and extends rotifer lifespan \| journal = PLOS One \| volume = 5 \| issue = 4 \| pages = e10206 \| date = April 2010 \| pmid = 20421998 \| pmc = 2858081 \| doi = 10.1371/journal.pone.0010206 \| url = }} 9. ^{{cite journal \| vauthors = Karbownik M, Reiter RJ, Garcia JJ, Cabrera J, Burkhardt S, Osuna C, Lewiński A \| title = Indole-3-propionic acid, a melatonin-related molecule, protects hepatic microsomal membranes from iron-induced oxidative damage: relevance to cancer reduction \| journal = Journal of Cellular Biochemistry \| volume = 81 \| issue = 3 \| pages = 507–13 \| date = 2001 \| pmid = 11255233 \| doi = 10.1002/1097-4644(20010601)81:3<507::AID-JCB1064>3.0.CO;2-M\| url = }} 10. ^{{cite journal \| vauthors = Reiter RJ, Tan DX, Osuna C, Gitto E \| title = Actions of melatonin in the reduction of oxidative stress. A review \| journal = Journal of Biomedical Science \| volume = 7 \| issue = 6 \| pages = 444–58 \| date = 2000 \| pmid = 11060493 \| doi = 10.1159/000025480 \| url = }} 11. ^{{cite journal \| vauthors = Behr C, Kamp H, Fabian E, Krennrich G, Mellert W, Peter E, Strauss V, Walk T, Rietjens IMCM, van Ravenzwaay B \| title = Gut microbiome-related metabolic changes in plasma of antibiotic-treated rats \| journal = Archives of Toxicology \| volume = 91 \| issue = 10 \| pages = 3439–3454 \| date = October 2017 \| pmid = 28337503 \| doi = 10.1007/s00204-017-1949-2 \| url = }} {{DEFAULTSORT:Indolepropionic acid, 3-}} 5 : Antioxidants\|Indoles\|Propionic acids\|Auxins\|Biomolecules
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