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Latest revision as of 19:01, 9 November 2024 edit undoSoumyapatra13 (talk | contribs)486 edits →Medical propertiesTag: 2017 wikitext editor |
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|ImageFile=NDGA.png |
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| verifiedrevid = 304291433 |
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|IUPACName=4,4'-(2,3-dimethylbutane-1,4-diyl)dibenzene-1,2-diol |
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| ImageFile=NDGA.png |
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|OtherNames= |
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|Section1= {{Chembox Identifiers |
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| IUPACName=4,4'-(2,3-Dimethylbutane-1,4-diyl)dibenzene-1,2-diol |
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| CASNo=500-38-9 |
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| OtherNames= |
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| PubChem=4534 |
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|Section1={{Chembox Identifiers |
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| SMILES=Oc2ccc(CC(C)C(C)Cc1ccc(O)c(O)c1)cc2O |
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| IUPHAR_ligand = 4265 |
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| MeSHName=Nordihydroguaiaretic+acid |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo=500-38-9 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 7BO8G1BYQU |
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| PubChem=4534 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 7625 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 52 |
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| SMILES=Oc2ccc(CC(C)C(C)Cc1ccc(O)c(O)c1)cc2O |
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| MeSHName=Nordihydroguaiaretic+acid |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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|C=18|H=22|O=4 |
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| C=18 | H=22 | O=4 |
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| MolarMass=302.365 |
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|Section3= {{Chembox Hazards |
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'''Nordihydroguaiaretic acid''' ('''NDGA''') is a classic ], a phenylpropane dimer linked by a bond between positions C8 and C8′, as opposed to a ]. It is a natural compound found in the ] (''Larrea tridentata''). |
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'''Nordihydroguaiaretic acid''' ('''NDGA''') is a potent ] compound found in the long-lived ]. It is believed that NDGA reduces cell damage by ], so under the ] of aging, could be responsible for the bush's long life. A 1986 study <ref>Richie JP Jr, Mills BJ, Lang CA. "Dietary nordihydroguaiaretic acid increases the life span of the mosquito." ''Proc Soc Exp Biol Med.'' 1986 Oct;183(1):81-5</ref> involved feeding female ]s NDGA to test the effect on their ]. While the usual mosquito life span was 29 days, the NDGA-fed mosquitos lived an average of 45 days—an increase of 50 percent. Nordihydroguaiaretic acid is also published as lengthening the lifespan of mice |
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== Medical properties == |
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The plant has been used to treat a variety of illnesses including ], ], ], ], ] and ], ] and ] but its use is controversial. It was widely used during the 1950s as a food preservative and to preserve natural fibers but was later banned after reports of toxicity during the early 1960s. Recently, it has been used as a nutritional supplement, however renal and hepatotoxicity are reported for chronic use of creosote bush and NDGA. <ref>Adapted from Arteaga S, Andrade-Cetto A, Cardenas R. "Larrea tridentata (Creosote bush), an abundant plant of Mexican and US-American deserts and its metabolite nordihydroguaiaretic acid." ''J Ethnopharmacol.'' 2005 Apr 26;98(3):231-9</ref> |
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As a lignan, it is a member of one of the major classes of ]s. While it is commonly asserted that the biological properties of lignans per sé are void, and that only the ]s ] and ], produced from lignans by intestinal bacteria have interesting biological properties,<ref>{{cite journal |last1=Clavel |first1=Thomas |last2=Henderson |first2=Gemma |last3=Alpert |first3=Carl-Alfred |last4=Philippe |first4=Catherine |last5=Rigottier-Gois |first5=Lionel |last6=Doré |first6=Joël |last7=Blaut |first7=Michael |title=Intestinal Bacterial Communities That Produce Active Estrogen-Like Compounds Enterodiol and Enterolactone in Humans |journal=Applied and Environmental Microbiology |date=October 2005 |volume=71 |issue=10 |pages=6077–6085 |doi=10.1128/aem.71.10.6077-6085.2005 |pmid=16204524 |pmc=1265965 |bibcode=2005ApEnM..71.6077C }}</ref> nordihydroguaiaretic acid has antioxidant and anti-inflammatory properties in vitro or in animal models.<ref>{{cite journal |last1=Wang |first1=Liang |last2=Li |first2=Lin |last3=Quan |first3=Mo-Yuan |last4=Wang |first4=Dong |last5=Jia |first5=Zhen |last6=Li |first6=Zhen-Fei |last7=Li |first7=Bin |last8=Guo |first8=Li |last9=Tan |first9=Guo-Jun |title=Nordihydroguaiaretic acid can suppress progression of experimental autoimmune encephalomyelitis |journal=IUBMB Life |date=May 2018 |volume=70 |issue=5 |pages=432–436 |doi=10.1002/iub.1739 |pmid=29637686 |s2cid=5010565 |doi-access=free }}</ref> It is a redox-type inhibitor of ].<ref>{{cite journal |last1=Gilbert |first1=Nathaniel C. |last2=Gerstmeier |first2=Jana |last3=Schexnaydre |first3=Erin E. |last4=Börner |first4=Friedemann |last5=Garscha |first5=Ulrike |last6=Neau |first6=David B. |last7=Werz |first7=Oliver |last8=Newcomer |first8=Marcia E. |title=Structural and mechanistic insights into 5-lipoxygenase inhibition by natural products |journal=Nature Chemical Biology |date=July 2020 |volume=16 |issue=7 |pages=783–790 |doi=10.1038/s41589-020-0544-7 |pmid=32393899 |pmc=7747934 }}</ref> |
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A 1986 study involved feeding female ]s NDGA to test the effect on their average lifespan. While the usual mosquito life span was 29 days, the NDGA-fed mosquitos lived an average of 45 days—an increase of 50 percent.<ref>{{Cite journal |
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==References== |
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| last1 = Richie Jr | first1 = J. P. |
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<references/> |
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| last2 = Mills | first2 = B. J. |
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| last3 = Lang | first3 = C. A. |
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| title = Dietary nordihydroguaiaretic acid increases the life span of the mosquito |
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| journal = Proceedings of the Society for Experimental Biology and Medicine |
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| volume = 183 |
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| issue = 1 |
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| pages = 81–85 |
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| year = 1986 |
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| pmid = 3749035 |
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| doi=10.3181/00379727-183-42389 |
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| s2cid = 45324341 |
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}}</ref> A 2008 study reported that nordihydroguaiaretic acid lengthened the lifespan of male mice, but not of female mice.<ref>{{Cite journal |
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| last1 = Strong | first1 = R. |
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| last2 = Miller | first2 = R. A. |
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| last3 = Astle | first3 = C. M. |
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| last4 = Floyd | first4 = R. A. |
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| last5 = Flurkey | first5 = K. |
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| last6 = Hensley | first6 = K. L. |
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| last7 = Javors | first7 = M. A. |
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| last8 = Leeuwenburgh | first8 = C. |
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| last9 = Nelson | first9 = J. F. |
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| doi = 10.1111/j.1474-9726.2008.00414.x |
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| last10 = Ongini | first10 = E. |
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| last11 = Nadon | first11 = N. L. |
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| last12 = Warner | first12 = H. R. |
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| last13 = Harrison | first13 = D. E. |
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| title = Nordihydroguaiaretic acid and aspirin increase lifespan of genetically heterogeneous male mice |
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| journal = Aging Cell |
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| volume = 7 |
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| issue = 5 |
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| pages = 641–650 |
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| year = 2008 |
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| pmid = 18631321 |
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| pmc = 2695675 |
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}}</ref> |
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The creosote plant has been used in herbal medicine, but its use is controversial. It was widely used during the 1950s as a food preservative and to preserve natural fibers, but was later banned after reports of toxicity during the early 1960s. Recently, it has been used as a nutritional supplement; however, ] ] and ] are reported for chronic use of creosote bush and NDGA.<ref>{{Cite journal |
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] |
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| last1 = Arteaga | first1 = S. |
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] |
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| last2 = Andrade-Cetto | first2 = A. |
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| last3 = Cárdenas | first3 = R. |
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| doi = 10.1016/j.jep.2005.02.002 |
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| title = Larrea tridentata (Creosote bush), an abundant plant of Mexican and US-American deserts and its metabolite nordihydroguaiaretic acid |
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| journal = Journal of Ethnopharmacology |
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| volume = 98 |
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| issue = 3 |
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| pages = 231–239 |
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| year = 2005 |
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| pmid = 15814253 |
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| pmc = |
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}}</ref><ref>{{cite journal |last1=Sahu |first1=Saura C. |last2=Ruggles |first2=Dennis I. |last3=O’Donnell |first3=Michael W. |title=Prooxidant activity and toxicity of nordihydroguaiaretic acid in clone-9 rat hepatocyte cultures |journal=Food and Chemical Toxicology |date=October 2006 |volume=44 |issue=10 |pages=1751–1757 |doi=10.1016/j.fct.2006.05.016 |pmid=16839654 |url=https://zenodo.org/record/1258937 }}</ref><ref>{{Cite journal |
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| pmid = 12457882 |
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| year = 2002 |
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| last1 = Lambert |
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| first1 = J. D. |
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| title = Nordihydroguaiaretic acid: Hepatotoxicity and detoxification in the mouse |
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| journal = Toxicon |
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| volume = 40 |
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| issue = 12 |
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| pages = 1701–8 |
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| last2 = Zhao |
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| first2 = D |
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| last3 = Meyers |
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| first3 = R. O. |
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| last4 = Kuester |
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| first4 = R. K. |
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| last5 = Timmermann |
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| first5 = B. N. |
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| last6 = Dorr |
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| first6 = R. T. |
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| doi=10.1016/s0041-0101(02)00203-9 |
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| bibcode = 2002Txcn...40.1701L |
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}}</ref> |
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== See also == |
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* ], an antineoplastic drug used to treat skin growths caused by sun exposure. |
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== References== |
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{{reflist}} |
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