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| verifiedrevid = 405929411 |
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| verifiedrevid = 477867469 |
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| Name = Usnic acid |
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| ImageFile = Usnic acid.svg |
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| Name = Usnic acid |
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| ImageFile = Usnic acid.svg |
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<!-- | ImageSize = 200px --> |
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| ImageName = Chemical structure of usnic acid |
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| ImageName = Chemical structure of usnic acid |
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| IUPACName = 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bh)<br />-dibenzofurandione |
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| IUPACName = 2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3(2''H'',9b''H'')-dione |
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| OtherNames = {{bulletedlist|Usneine|Usninic acid|Usniacin}} |
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| OtherNames = usneine, usninic acid, usniacin |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 125-46-2<ref name="AshAsh2004">{{cite book |
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| CASNo = 125-46-2 |
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|author1=Michael Ash |
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| CASNo_Comment = ] |
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|author2=Irene Ash |
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| CASNo1_Ref = {{cascite|correct|CAS}} |
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|title=Handbook of preservatives |
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| CASNo1 = 7562-61-0 |
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|url=http://books.google.com/books?id=XZ2QB7bu5LwC&pg=PA670 |
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| CASNo1_Comment = (''R'')-(+) |
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|accessdate=5 August 2010 |
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| CASNo2_Ref = {{cascite|correct|CAS}} |
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|year=2004 |
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| CASNo2 = 6159-66-6 |
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|publisher=Synapse Info Resources |
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| CASNo2_Comment = (''S'')-(–) |
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|isbn=9781890595661 |
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|page=5856}}</ref> |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 242022 |
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| ChEMBL = 242022 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| SMILES = CC1=C(C(=C2C(=C1O)C3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O |
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| PubChem = 5646 |
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| ChEBI = 38319 |
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| SMILES = CC1=C(C(=C2C(=C1O)C3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O |
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| ChemSpiderID = 5444 |
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| PubChem = 5646 |
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| InChI = 1/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| InChIKey = CUCUKLJLRRAKFN-UHFFFAOYAS |
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| ChemSpiderID = 5444 |
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| StdInChI = 1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| StdInChIKey = CUCUKLJLRRAKFN-UHFFFAOYSA-N |
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| UNII = 0W584PFJ77 |
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}} |
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| UNII1_Ref = {{fdacite|correct|FDA}} |
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| Section2 = {{Chembox Properties |
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| UNII1 = 663456969I |
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| Formula = C<sub>18</sub>H<sub>16</sub>O<sub>7</sub> |
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| UNII1_Comment = (''R'')-(+) |
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| MolarMass = 344.315 g/mol |
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| UNII2_Ref = {{fdacite|correct|FDA}} |
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| Density = |
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| UNII2 = 5HYW08F205 |
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| MeltingPt = 204°C |
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| UNII2_Comment = (''S'')-(–) |
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| BoilingPt = |
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| InChI = 1/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3 |
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| InChIKey = CUCUKLJLRRAKFN-UHFFFAOYAS |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C18H16O7/c1-6-14(22)12(8(3)20)16-13(15(6)23)18(4)10(25-16)5-9(21)11(7(2)19)17(18)24/h5,11,22-23H,1-4H3 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = CUCUKLJLRRAKFN-UHFFFAOYSA-N |
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}} |
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}} |
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| Section2 = {{Chembox Properties |
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| C=18 | H=16 | O=7 |
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| Density = |
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| MeltingPtC = 204 |
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| BoilingPt = |
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|Solubility = <0.001 g/L (25°C)<ref name="Merck">{{Cite book |title=The Merck index: an encyclopedia of chemicals, drugs, and biologicals |date=2001 |publisher=Merck |year=2001 |isbn=978-0-911910-13-1 |editor-last=O'Neil |editor-first=Maryadele J. |edition=13th |location=Whitehouse Station, NJ |page=1762 |language=English |editor-last2=Merck Sharp and Dohme Research Laboratories}}</ref> |
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|Solvent1 = acetone |
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|Solubility1 = 0.077 g/L<ref name="Merck"/> |
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|Solvent2 = ethyl acetate |
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|Solubility2 = 0.088 g/L<ref name="Merck"/> |
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|Solvent3 = furfural |
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|Solubility3 = 0.732 g/L<ref name="Merck"/> |
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|Solvent4 = furfuryl alcohol |
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|Solubility4 = 0.121 g/L<ref name="Merck"/> |
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}} |
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'''Usnic acid''' is a naturally occurring ] derivative found in several ] species with the formula C<sub>18</sub>H<sub>16</sub>O<sub>7</sub>. It was first isolated by German scientist W. Knop in 1844<ref>{{cite journal | last1 = Knop | first1 = W | year = 1844 | title = Chemisch-physiologische Untersuchung uber die Flechten | url = https://zenodo.org/record/1426980| journal = Annalen der Chemie und Pharmacie| volume = 49 | issue = 2| pages = 103–124 | doi=10.1002/jlac.18440490202}}</ref> and first synthesized between 1933 and 1937 by Curd and Robertson.<ref>{{cite journal | last1 = Robertson | first1 = A. | last2 = Curd | first2 = F. H. | year = 1933 | title = 277. Usnic acid. Part III. Usnetol, usnetic acid, and pyrousnic acid| journal = Journal of the Chemical Society (Resumed)| page = 1173 | doi = 10.1039/jr9330001173 }}</ref> Usnic acid was identified in many genera of lichens including '']'', '']'', '']'', '']'', '']'', '']'', '']'' and '']''. Although it is generally believed that usnic acid is exclusively restricted to lichens, in a few unconfirmed isolated cases the compound was found in ] tea and non-lichenized ].<ref name="CocchiettoSkert2002">{{cite journal|last1=Cocchietto|first1=Moreno|last2=Skert|first2=Nicola|last3=Nimis|first3=Pier|last4=Sava|first4=Gianni|title=A review on usnic acid, an interesting natural compound|journal=Naturwissenschaften|volume=89|issue=4|year=2002|pages=137–146|issn=0028-1042|doi=10.1007/s00114-002-0305-3|pmid=12061397|bibcode=2002NW.....89..137C|s2cid=11481018}}</ref><ref name="Blanc1996">{{cite journal|last1=Blanc|first1=Philippe J.|title=Characterization of the tea fungus metabolites|journal=Biotechnology Letters|volume=18|issue=2|year=1996|pages=139–142|issn=0141-5492|doi=10.1007/BF00128667|s2cid=34822312}}</ref> |
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'''Usnic acid''' is a naturally occurring ] derivative found in several ] species. It was first isolated by German scientist W. Knop in 1844<ref>Knop W. (1844) Chemisch-physiologische Untersuchung uber die Flechten. ''Justus Lieb. Ann. Chern'' 49: 103-124. |
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</ref> and first synthesized between 1933-1937 by Curd and Robertson.<ref>A. Robertson and F. H. Curd. ''J. Chem. Soc.'' 1173 (1933)</ref> Usnic acid was identified in many genera of lichens including '']'', '']'', '']'', '']'', '']'', '']'' and '']''. Although it is generally believed that usnic acid is exclusively restricted to lichens, in a few unconfirmed isolated cases the compound was found in ] tea and non-lichenized ]. |
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At normal conditions, usnic acid is a bitter, yellow, solid substance.<ref name="AshAsh2004"/> It is known to occur in nature in both the d- and l-forms as well as a racemic mixture. |
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At normal conditions, usnic acid is a bitter, yellow, solid substance.<ref name="AshAsh2004">{{cite book |
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| author1 =Michael Ash |
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| author2 =Irene Ash |
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| title =Handbook of preservatives |
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| url =https://books.google.com/books?id=XZ2QB7bu5LwC&pg=PA670 |
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| access-date =5 August 2010 |
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| year =2004 |
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| publisher =Synapse Info Resources |
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| isbn =978-1-890595-66-1 |
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| page =5856}}</ref> It is known to occur in nature in both the d- and l-forms as well as a ] mixture. Salts of usnic acid are called usnates (e.g. ]). |
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==Biological role in lichens== |
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==Biological role in lichens== |
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Usnic acid is a secondary metabolite in lichens whose role has not been completely elucidated. It is believed that usnic acid protects the lichen from adverse effects of sunlight exposure and deters grazing animals with its bitter taste. |
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Usnic acid is a secondary metabolite in lichens whose role has not been completely elucidated. It is believed that usnic acid protects the lichen from adverse effects of sunlight exposure and deters grazing animals with its bitter taste. |
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==Biosynthesis== |
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==Uses and properties== |
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Usnic acid is a ] biosynthesized via methylphloroacetophenone as an intermediate.<ref>{{Cite journal | doi = 10.1248/cpb.17.2054 | pmid = 5353559 | title = Biosynthesis of Natural Products. VI. Biosynthesis of Usnic Acid in Lichens. (1). A General Scheme of Biosynthesis of Usnic Acid | journal = Chemical & Pharmaceutical Bulletin | volume = 17 | issue = 10 | pages = 2054–2060 | year = 1969 | last1 = Taguchi | first1 = Heihachiro | last2 = Sankawa | first2 = Ushio | last3 = Shibata | first3 = Shoji | doi-access = free }} |
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</ref> |
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]{{clear-left}} |
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==Safety== |
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Lichen extracts containing usnic acid have been utilized in medicine, perfumery, cosmetics, and ecology. |
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Usnic acid and its salts are idiosyncratically associated with severe ] and ].<ref>{{cite journal | doi = 10.1111/j.1440-1746.2008.05310.x | pmid = 18318821 | title = Hepatotoxic slimming aids and other herbal hepatotoxins | journal = Journal of Gastroenterology and Hepatology | volume = 23 | issue = 3 | pages = 366–373 | year = 2008 | last1 = Chitturi | first1 = Shivakumar | last2 = Farrell | first2 = Geoffrey C. | s2cid = 23840983 }} |
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</ref><ref>{{cite journal |
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| vauthors = Yellapu RK, Mittal V, Grewal P, Fiel M, Schiano T |
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| title = Acute liver failure caused by 'fat burners' and dietary supplements: a case report and literature review |
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| journal = Canadian Journal of Gastroenterology| volume = 25 |
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| issue = 3 |
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| pages = 157–60 |
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| year = 2011 |
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| pmid = 21499580 |
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| pmc = 3076034 |
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| doi = 10.1155/2011/174978 |
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| doi-access = free |
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}}</ref> Daily oral intake of 300–1350 mg over a period of weeks has led to severe hepatotoxicity in a number of persons.<ref>{{cite journal | last1 = Hsu | first1 = LM | last2 = Huang | first2 = YS | last3 = Chang | first3 = FY | last4 = Lee | first4 = SD | date = Jul 2005 | title = 'Fat burner' herb, usnic acid, induced acute hepatitis in a family | journal = Journal of Gastroenterology and Hepatology| volume = 20 | issue = 7| pages = 1138–9 | doi=10.1111/j.1440-1746.2005.03855.x| pmid = 15955234 | s2cid = 6717430 }}</ref><ref>{{cite journal | doi = 10.4065/81.4.541 | pmid = 16610575 | title = Severe Hepatotoxicity Associated with Use of a Dietary Supplement Containing Usnic Acid | journal = Mayo Clinic Proceedings | volume = 81 | issue = 4 | pages = 541–544 | year = 2006 | last1 = Sanchez | first1 = William | last2 = Maple | first2 = John T. | last3 = Burgart | first3 = Lawrence J. | last4 = Kamath | first4 = Patrick S. | doi-access = }}</ref> |
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Sodium usnate was one ingredient in a product called "Lipokinetix" that was claimed to induce weight loss via an increase in metabolic rate. Lipokinetix has been the topic of an FDA warning in the USA<ref>{{cite web|title=Safety Alerts for Human Medical Products > Lipokinetix|url=https://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm172824.htm|work=MedWatch: The FDA Safety Information and Adverse Event Reporting Program|publisher=U.S. Food and Drug Administration|access-date=5 December 2012|date=November 20, 2001|quote=FDA has received multiple reports of persons who developed liver injury or liver failure while using Lipokinetix. The product contains norephedrine (also known as phenylpropanolamine or PPA), caffeine, yohimbine, diiodothyronine, and sodium usniate.}}</ref> due to potential hepatotoxicity, although it is unclear yet if any toxicity would be attributable to the aforementioned salt. Lipokinetix also contained ] (PPA), ], ] and ]. |
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Usnic acid possess a wide range of interesting biological properties. It is a potent antibiotic effective against gram positive bacteria, including '']'', '']'', '']'', and '']'', as well as some pathogenic ]. It also exhibits antiviral, antiprotozoal, antimitotic, anti-inflammatory and analgesic activity. Other characteristics, like ultraviolet absorption, preserving properties, antigrowth, antiherbivore and anti-insect properties, have also been demonstrated. |
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==Pharmacology== |
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Usnic acid has been included as an ingredient in creams, powders, toothpastes, mouthwash, deodorants, hair shampoos and sunscreen products. In some of these preparations, usnic acid is employed as an active principle, in others as a preservative. |
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Usnic acid has been found to have ] in both frog and earthworm nerve junction models in preliminary research.<ref>Harris N. J. (1961), Honors Thesis, Clark University, Worcester, Massachusetts</ref> |
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==Analytics== |
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Usnic acid and its salt form, sodium usniate, have been marketed in the US as an ingredient in food supplements for use in weight reduction, although unsupported by solid scientific proof. These supplements, if taken according to label instructions, can supply daily oral doses of 10–1350 mg for adults. Daily oral intake of 300–1350 mg over a period of weeks has led to severe hepatotoxicity in a number of persons.<ref>Hsu LM, Huang YS, Chang FY, Lee SD. 'Fat burner' herb, usnic acid, induced acute hepatitis in a family. J Gastroenterol Hepatol. 2005 Jul;20(7):1138-9.</ref><ref>Sanchez W, Maple JT, Burgart LJ, Kamath PS. Severe hepatotoxicity associated with use of a dietary supplement containing usnic acid. Mayo Clin Proc. 2006 Apr;81(4):541-4.</ref> |
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It is possible to determine the content of usnic acid in ] ] using reversed-polarity ] or ] analysis.<ref>{{cite journal | doi = 10.1002/1522-2683(200108)22:13<2755::AID-ELPS2755>3.0.CO;2-6 | title = Reversed-polarity capillary zone electrophoretic analysis of usnic acid | journal = Electrophoresis | volume = 22 | issue = 13 | pages = 2755–2757 | year = 2001 | last1 = Kreft | first1 = Samo | last2 = Štrukelj | first2 = Borut | pmid = 11545403 | s2cid = 24341350 }} |
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Usnea was one ingredient in a product called Lipokinetix, promoted to induce weight loss via increase in metabolic rate. Lipokinetix has been the topic of an FDA warning in the USA,<ref>http://www.cfsan.fda.gov/~dms/ds-lipo.html</ref> due to potential hepatotoxicity, although it is unclear yet if any toxicity would be attributable to the Usnea. Lipokinetix also contained PPA, caffeine, yohimbine and diiodothyronine. There is reason to believe that usnic acid, in high concentrations, could possess some toxicity. The National Toxicology Program is currently evaluating the issue. |
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</ref> |
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==Pharmacolgy== |
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Usnic acid has been found to have adrenergic activity in both frog and earthworm nerve junction models in preliminary research.<ref>Harris N. J.(1961), Honors Thesis, Clark University, Worcester, Massachusetts</ref> |
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==References== |
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==References== |
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==External links== |
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==External links== |
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* , ''New York Times'', March 4, 2003 |
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* http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=search&db=pcsubstance&term=usnic%20acid |
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* http://bioweb.ucr.edu/ChemMine/view.php?TYPE=1&i_id=996789 |
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* http://ntp.niehs.nih.gov/index.cfm?objectid=E87D09E6-BDB5-82F8-FF11A36F2EEA025F |
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* http://query.nytimes.com/gst/fullpage.html?res=9802E2DD163FF937A35750C0A9659C8B63 |
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{{DEFAULTSORT:Usnic Acid}} |
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{{DEFAULTSORT:Usnic Acid}} |
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