| 词条 | Ellagic acid |
| 释义 |
| Watchedfields = changed | verifiedrevid = 477313805 | Name = Ellagic acid | ImageFile = Ellagic acid.svg | ImageSize = 220 | ImageAlt = Skeletal formula of ellagic acid | ImageFile1 = Ellagic acid 3D spacefill.png | ImageAlt1 = Space-filling model of the ellagic acid molecule | IUPACName = 2,3,7,8-Tetrahydroxy-chromeno[5,4,3-cde]chromene-5,10-dione | OtherNames = 4,4′,5,5′,6,6′-Hexahydroxydiphenic acid 2,6,2′,6′-dilactone |Section1={{Chembox Identifiers | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 4445149 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 19YRN3ZS9P | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C10788 | InChI = 1/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H | InChIKey = AFSDNFLWKVMVRB-UHFFFAOYAQ | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 6246 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = AFSDNFLWKVMVRB-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 476-66-4 | PubChem = 5281855 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB08468 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 4775 | SMILES = O=C1Oc3c2c4c1cc(O)c(O)c4OC(=O)c2cc(O)c3O }} |Section2={{Chembox Properties | Formula = C14H6O8 | MolarMass = 302.197 g/mol | Density = 1.67 g/cm3 | MeltingPt = | BoilingPt = }} Ellagic acid is a natural phenol antioxidant found in numerous fruits and vegetables. The antiproliferative and antioxidant properties of ellagic acid have prompted research into its potential health benefits. Ellagic acid is the dilactone of hexahydroxydiphenic acid. NameThe name comes from the French term acide ellagique, from the word galle spelled backwards[1] because it can be obtained from noix de galle (galls), and to distinguish it from acide gallique (gallic acid). MetabolismBiosynthesisPlants produce ellagic acid from hydrolysis of tannins such as ellagitannin and geraniin.[2]{{rp|208}} BiodegradationUrolithins are microflora human metabolites of dietary ellagic acid derivatives[3]HistoryEllagic acid was first discovered by chemist Henri Braconnot in 1831.[4]{{rp|20}} Maximilian Nierenstein prepared this substance from algarobilla, dividivi, oak bark, pomegranate, myrabolams, and valonea in 1905.[4]{{rp|20}} He also suggested its formation from galloyl-glycine by Penicillium in 1915.[5] Löwe was the first person to synthesize ellagic acid by heating gallic acid with arsenic acid or silver oxide.[4]{{rp|20}} [6] Natural occurrencesEllagic acid is found in oak species such as the North American white oak (Quercus alba) and European red oak (Quercus robur).[7] The macrophyte Myriophyllum spicatum produces ellagic acid.[8] Ellagic acid can be found in the medicinal mushroom Phellinus linteus.[9] In foodThe highest levels of ellagic acid are found in walnuts, pecans, cranberries, raspberries, strawberries, and grapes, as well as distilled beverages.[10] It is also found in peaches[11] and pomegranates.[12] Medicinal claims and researchEllagic acid has antiproliferative and antioxidant properties in a number of in vitro and small-animal models.[13][14] The antiproliferative properties of ellagic acid may be due to its ability to directly inhibit the DNA binding of certain carcinogens, including nitrosamines[15][16] and polycyclic aromatic hydrocarbons.[17] As with other polyphenol antioxidants, ellagic acid has a chemoprotective effect in cellular models by reducing oxidative stress.[10] Ellagic acid has been marketed as a dietary supplement with a range of claimed benefits against cancer, heart disease, and other medical problems. Ellagic acid has been identified by the U.S. Food and Drug Administration as a "fake cancer 'cure'".[18] A number of U.S.-based sellers of dietary supplements have received Warning Letters from the Food and Drug Administration for promoting ellagic acid with claims that violate the Federal Food, Drug, and Cosmetic Act.[19][20] Urolithins, such as urolithin A, are microflora human metabolites of dietary ellagic acid derivatives that are under study as anti-cancer agents.[21] Claims that ellagic acid can treat or prevent cancer in humans have not been proven.[22] See also
References1. ^ellagique in the Dictionnaire de la langue française of Émile Littré. 2. ^{{cite book|author=David S. Seigler|title=Plant Secondary Metabolism|url=https://books.google.com/books?id=hmYbjbGU-EgC|date=31 December 1998|publisher=Springer Science & Business Media|isbn=978-0-412-01981-4}} 3. ^{{Cite journal|pmid=16506809|year=2006|last1=Larrosa|first1=M|last2=González-Sarrías|first2=A|last3=García-Conesa|first3=MT|last4=Tomás-Barberán|first4=FA|last5=Espín|first5=JC|title=Urolithins, ellagic acid-derived metabolites produced by human colonic microflora, exhibit estrogenic and antiestrogenic activities|volume=54|issue=5|pages=1611–20|doi=10.1021/jf0527403|journal=Journal of Agricultural and Food Chemistry}} 4. ^1 2 {{Cite book|url=https://archive.org/details/synthetictannins032496mbp|title=Synthetic Tannins|isbn=9781406773019|author1=Grasser|first1=Georg|date=1922|others=F. G. A. Enna.}} 5. ^{{Cite journal|pmid=16742368|year=1915|last1=Nierenstein|first1=M|title=The Formation of Ellagic Acid from Galloyl-Glycine by Penicillium|volume=9|issue=2|pages=240–4|pmc=1258574|journal=The Biochemical Journal|doi=10.1042/bj0090240}} 6. ^Löwe, Zeitschrift für Chemie, 1868, 4, 603 7. ^{{cite journal|doi=10.1016/S0021-9673(00)00624-5|title=Analysis of oak tannins by liquid chromatography-electrospray ionisation mass spectrometry|year=2000|last1=Mämmelä|first1=Pirjo|last2=Savolainen|first2=Heikki|last3=Lindroos|first3=Lasse|last4=Kangas|first4=Juhani|last5=Vartiainen|first5=Terttu|journal=Journal of Chromatography A|volume=891|pages=75–83|pmid=10999626|issue=1}} 8. ^{{Cite journal|doi=10.1016/S0043-1354(00)00039-7|title=Myriophyllum spicatum-released allelopathic polyphenols inhibiting growth of blue-green algae Microcystis aeruginosa|year=2000|last1=Nakai|first1=S|journal=Water Research|volume=34|issue=11|pages=3026–3032}} 9. ^{{cite journal |vauthors=Lee YS, Kang YH, Jung JY, Lee S, Ohuchi K, Shin KH, Kang IJ, Park JH, Shin HK, Lim SS |title=Protein glycation inhibitors from the fruiting body of Phellinus linteus |journal=Biol. Pharm. Bull. |volume=31 |issue=10 |pages=1968–72 |year=2008 |pmid=18827365 |doi=10.1248/bpb.31.1968 }} 10. ^1 {{cite journal | doi = 10.1111/j.1745-4514.2005.00031.x |author1=D. A. Vattem |author2=K. Shetty | title = Biological Function of Ellagic Acid: A Review | journal = Journal of Food Biochemistry | year = 2005 | volume = 29 | issue = 3 | pages = 234–266}} 11. ^Postharvest sensory and phenolic characterization of ‘Elegant Lady’ and ‘Carson’ peaches. Rodrigo Infante, Loreto Contador, Pía Rubio, Danilo Aros and Álvaro Peña-Neira, Chilean Journal of Agricultural Research, 71(3), July–September 2011, pages 445-451 (article) 12. ^{{cite journal|last1=Usta|first1=C|last2=Ozdemir|first2=S|last3=Schiariti|first3=M|last4=Puddu|first4=PE|title=The pharmacological use of ellagic acid-rich pomegranate fruit.|journal=International Journal of Food Sciences and Nutrition|date=November 2013|volume=64|issue=7|pages=907–13|doi=10.3109/09637486.2013.798268|pmid=23700985}} 13. ^{{cite journal |author=Seeram NP |title=In vitro antiproliferative, apoptotic and antioxidant activities of punicalagin, ellagic acid and a total pomegranate tannin extract are enhanced in combination with other polyphenols as found in pomegranate juice |journal=J. Nutr. Biochem. |volume=16 |issue=6 |pages=360–7 |date=June 2005 |pmid=15936648 |doi=10.1016/j.jnutbio.2005.01.006 |url= |name-list-format=vanc|author2=Adams LS |author3=Henning SM |display-authors=3 |last4=Niu |first4=Y |last5=Zhang |first5=Y |last6=Nair |first6=M |last7=Heber |first7=D}} 14. ^{{cite journal |vauthors=Narayanan BA, Geoffroy O, Willingham MC, Re GG, Nixon DW |title=p53/p21(WAF1/CIP1) expression and its possible role in G1 arrest and apoptosis in ellagic acid treated cancer cells |journal=Cancer Lett. |volume=136 |issue=2 |pages=215–21 |date=March 1999 |pmid=10355751 |url=http://linkinghub.elsevier.com/retrieve/pii/S0304-3835(98)00323-1 |doi=10.1016/S0304-3835(98)00323-1}} 15. ^{{cite journal |author1=Madal, Shivappurkar |author2=Galati, Stoner |last-author-amp=yes | title = Inhibition of N-nitrosobenzymethylamine metabolism and DNA binding in cultured rat esophagus by ellagic acid | journal = Carcinogenesis | year = 1988 | volume = 9 | pages = 1313–1316 | doi = 10.1093/carcin/9.7.1313 | pmid = 3383347 | issue = 7}} 16. ^{{cite journal | author = Mandal and Stoner | title = Inhibition of N-nitrosobenzymethylamine-induced esophageal tumorigenesis in rats by ellagic acid | journal = Carcinogenesis | year = 1990 | volume = 11 | pages = 55–61 | doi = 10.1093/carcin/11.1.55 | pmid = 2295128 | last2 = Stoner | first2 = GD | issue = 1}} 17. ^{{cite journal |author1=Teel, Babcock |author2=Dixit, Stoner |last-author-amp=yes | title = Ellagic acid toxicity and interaction with benzo[a]pyrene and benzo[a]pyrene 7,8-dihydrodiol in human bronchial epithelial cells | journal = Cell Biol. Toxicol. | year = 1986 | volume = 2 | pages = 53–62 | doi = 10.1007/BF00117707 | pmid = 3267445 | issue = 1}} 18. ^187 Fake Cancer 'Cures' Consumers Should Avoid, from the U.S. Food and Drug Administration. Accessed June 17, 2008. [https://web.archive.org/web/20170502034227/https://www.fda.gov/drugs/guidancecomplianceregulatoryinformation/enforcementactivitiesbyfda/ucm171057.htm Archived] by the Wayback Machine on May 2, 2017. 19. ^Warning Letter sent to Millennium Health by the United States Food and Drug Administration, dated May 21, 2008. 20. ^Warning Letter sent to Kenton Campbell at Prime Health Direct, Ltd. by the United States Food and Drug Administration dated July 2, 2007. 21. ^Davis CD, Milner JA. [https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2743755/ Gastrointestinal microflora, food components and colon cancer prevention]. J Nutr Biochem. 2009 Oct;20(10):743-52. {{doi|10.1016/j.jnutbio.2009.06.001}}. {{PMID|19716282}} 22. ^{{cite web |url=http://www.cancer.org/treatment/treatmentsandsideeffects/complementaryandalternativemedicine/dietandnutrition/ellagic-acid |publisher=American Cancer Society |date=November 2008 |title=Ellagic acid |accessdate=1 August 2014}} External links
3 : Ellagitannins|Health fraud|Pomegranate ellagitannins |
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