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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 due to potential hepatotoxicity, although it is unclear yet if any toxicity would be attributable
1232:
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
656:
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.
142:
581:. It was first isolated by German scientist W. Knop in 1844 and first synthesized between 1933 and 1937 by Curd and Robertson. Usnic acid was identified in many genera of lichens including
1180:
Sanchez, William; Maple, John T.; Burgart, Lawrence J.; Kamath, Patrick S. (2006). "Severe
Hepatotoxicity Associated with Use of a Dietary Supplement Containing Usnic Acid".
629:. Although it is generally believed that usnic acid is exclusively restricted to lichens, in a few unconfirmed isolated cases the compound was found in
539:
640:
At normal conditions, usnic acid is a bitter, yellow, solid substance. It is known to occur in nature in both the d- and l-forms as well as a
373:
1215:
1004:"Biosynthesis of Natural Products. VI. Biosynthesis of Usnic Acid in Lichens. (1). A General Scheme of Biosynthesis of Usnic Acid"
1267:
866:
Cocchietto, Moreno; Skert, Nicola; Nimis, Pier; Sava, Gianni (2002). "A review on usnic acid, an interesting natural compound".
745:
979:
782:
1299:
1137:
Hsu, LM; Huang, YS; Chang, FY; Lee, SD (Jul 2005). "'Fat burner' herb, usnic acid, induced acute hepatitis in a family".
693:. Daily oral intake of 300–1350 mg over a period of weeks has led to severe hepatotoxicity in a number of persons.
534:
798:
338:
546:
1254:
Kreft, Samo; Štrukelj, Borut (2001). "Reversed-polarity capillary zone electrophoretic analysis of usnic acid".
347:
InChI=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
1043:
Chitturi, Shivakumar; Farrell, Geoffrey C. (2008). "Hepatotoxic slimming aids and other herbal hepatotoxins".
357:
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
843:
Robertson, A.; Curd, F. H. (1933). "277. Usnic acid. Part III. Usnetol, usnetic acid, and pyrousnic acid".
625:
257:
220:
1088:"Acute liver failure caused by 'fat burners' and dietary supplements: a case report and literature review"
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773:
O'Neil, Maryadele J.; Merck Sharp and Dohme
Research Laboratories, eds. (2001).
722:
686:
517:
1244:
Harris N. J. (1961), Honors Thesis, Clark
University, Worcester, Massachusetts
887:
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946:
925:
Blanc, Philippe J. (1996). "Characterization of the tea fungus metabolites".
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in both frog and earthworm nerve junction models in preliminary research.
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10.1002/1522-2683(200108)22:13<2755::AID-ELPS2755>3.0.CO;2-6
1220:
MedWatch: The FDA Safety
Information and Adverse Event Reporting Program
1020:
1003:
938:
666:
501:
487:
473:
459:
424:
193:
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Usnic acid and its salts are idiosyncratically associated with severe
1193:
775:
The Merck index: an encyclopedia of chemicals, drugs, and biologicals
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813:
516:
Except where otherwise noted, data are given for materials in their
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630:
607:
601:
589:
491:
141:
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463:
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biosynthesized via methylphloroacetophenone as an intermediate.
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566:
173:
777:(13th ed.). Whitehouse Station, NJ: Merck. p. 1762.
583:
153:
131:
1002:
Taguchi, Heihachiro; Sankawa, Ushio; Shibata, Shoji (1969).
307:
1216:"Safety Alerts for Human Medical Products > Lipokinetix"
1086:
Yellapu RK, Mittal V, Grewal P, Fiel M, Schiano T (2011).
40:
2,6-Diacetyl-7,9-dihydroxy-8,9b-dimethyldibenzofuran-1,3(2
1179:
733:
It is possible to determine the content of usnic acid in
381:
CC1=C(C(=C2C(=C1O)C3(C(=CC(=O)C(C3=O)C(=O)C)O2)C)C(=O)C)O
865:
814:"Chemisch-physiologische Untersuchung uber die Flechten"
1085:
697:
to the aforementioned salt. Lipokinetix also contained
1222:. U.S. Food and Drug Administration. November 20, 2001
644:
mixture. Salts of usnic acid are called usnates (e.g.
1001:
967:
859:
1311:
1136:
245:
1042:
112:
100:
89:
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1139:Journal of Gastroenterology and Hepatology
1045:Journal of Gastroenterology and Hepatology
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845:Journal of the Chemical Society (Resumed)
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1300:Seeking to Fight Fat, She Lost Her Liver
974:. Synapse Info Resources. p. 5856.
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318:
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1008:Chemical & Pharmaceutical Bulletin
746:high performance liquid chromatography
442:204 °C (399 °F; 477 K)
214:
924:
350:Key: CUCUKLJLRRAKFN-UHFFFAOYSA-N
181:
161:
1092:Canadian Journal of Gastroenterology
811:
757:
676:Proposed biosynthesis for usnic acid
360:Key: CUCUKLJLRRAKFN-UHFFFAOYAS
236:
13:
721:Usnic acid has been found to have
14:
1361:
1293:
1151:10.1111/j.1440-1746.2005.03855.x
1057:10.1111/j.1440-1746.2008.05310.x
818:Annalen der Chemie und Pharmacie
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968:Michael Ash; Irene Ash (2004).
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520:(at 25 °C , 100 kPa).
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742:capillary zone electrophoresis
414:
402:
1:
797:: CS1 maint: date and year (
751:
728:
565:derivative found in several
7:
10:
1366:
652:Biological role in lichens
569:species with the formula C
971:Handbook of preservatives
888:10.1007/s00114-002-0305-3
680:
561:is a naturally occurring
514:
389:
369:
334:
73:
53:
35:
30:
21:
830:10.1002/jlac.18440490202
740:using reversed-polarity
1182:Mayo Clinic Proceedings
633:tea and non-lichenized
677:
927:Biotechnology Letters
675:
454:<0.001 g/L (25°C)
853:10.1039/jr9330001173
1105:10.1155/2011/174978
1021:10.1248/cpb.17.2054
880:2002NW.....89..137C
868:Naturwissenschaften
723:adrenergic activity
711:3,5-diiodothyronine
449:Solubility in water
432: g·mol
18:
939:10.1007/BF00128667
678:
547:Infobox references
16:
1262:(13): 2755–2757.
1014:(10): 2054–2060.
981:978-1-890595-66-1
784:978-0-911910-13-1
555:Chemical compound
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303:CompTox Dashboard
143:Interactive image
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1335:Acetyl compounds
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812:Knop, W (1844).
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665:Usnic acid is a
537:
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506:furfuryl alcohol
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699:norephedrine
695:
684:
664:
661:Biosynthesis
655:
639:
624:
618:
612:
606:
600:
596:Hypotrachyna
594:
588:
582:
563:dibenzofuran
558:
557:
290:
278:
183:ChEMBL242022
118:
106:
74:Identifiers
62:Usninic acid
54:Other names
45:
41:
1345:Resorcinols
1340:Polyketides
1320:Polyphenols
635:ascomycetes
390:Properties
221:100.004.310
163:CHEBI:38319
17:Usnic acid
1314:Categories
1226:5 December
752:References
748:analysis.
667:polyketide
559:Usnic acid
510:0.121 g/L
502:Solubility
496:0.732 g/L
488:Solubility
482:0.088 g/L
474:Solubility
468:0.077 g/L
460:Solubility
425:Molar mass
286:5HYW08F205
274:663456969I
267:0W584PFJ77
194:ChemSpider
130:3D model (
81:CAS Number
37:IUPAC name
947:0141-5492
896:0028-1042
793:cite book
729:Analytics
707:yohimbine
626:Alectoria
114:6159-66-6
102:7562-61-0
1284:24341350
1276:11545403
1233:usniate.
1202:16610575
1159:15955234
1124:21499580
1073:23840983
1065:18318821
987:5 August
955:34822312
912:11481018
904:12061397
847:: 1173.
703:caffeine
631:kombucha
620:Parmelia
608:Ramalina
602:Lecanora
590:Cladonia
492:furfural
91:125-46-2
65:Usniacin
1167:6717430
1115:3076034
1030:5353559
876:Bibcode
738:extract
701:(PPA),
642:racemic
614:Evernia
540:what is
538: (
464:acetone
430:344.319
289: (
277: (
234:PubChem
117: (
105: (
96:racemic
59:Usneine
48:)-dione
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781:
735:lichen
681:Safety
567:lichen
535:verify
532:
374:SMILES
174:ChEMBL
94:
31:Names
1280:S2CID
1163:S2CID
1069:S2CID
951:S2CID
908:S2CID
584:Usnea
339:InChI
293:)-(–)
281:)-(+)
154:ChEBI
132:JSmol
121:)-(–)
109:)-(+)
1272:PMID
1228:2012
1198:PMID
1155:PMID
1120:PMID
1061:PMID
1026:PMID
989:2010
976:ISBN
943:ISSN
900:PMID
892:ISSN
799:link
779:ISBN
709:and
689:and
623:and
258:UNII
247:5646
203:5444
1264:doi
1190:doi
1147:doi
1110:PMC
1100:doi
1053:doi
1016:doi
935:doi
884:doi
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826:doi
744:or
648:).
504:in
490:in
476:in
462:in
308:EPA
237:CID
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