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Latest revision as of 08:17, 17 November 2024 edit undoGraeme Bartlett (talk | contribs)Administrators249,654 edits added Category:Fungal pigments using HotCat |
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{{short description|Chemical compound}} |
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| verifiedrevid = 385704022 |
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| Name = Vulpinic acid |
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| Name = Vulpinic acid |
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| ImageFileL1 = Vulpinic acid.png |
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| ImageFileL1 = Vulpinic acid Structural Formula V1.svg |
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| ImageSizeL1 = 125px |
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| ImageSizeL1 = 125px |
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| ImageFileR1 = Vulpinic acid.jpg |
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| ImageFileR1 = Vulpinic acid - 3D - Ball-and-stick Model.png |
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| ImageSizeR1 = 125px |
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| ImageSizeR1 = 125px |
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| ImageNameL1 = Chemical structure of vulpinic acid |
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| ImageNameL1 = Chemical structure of vulpinic acid |
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| IUPACName = Methyl (2''E'')-2-(5-hydroxy-3-oxo-4-phenylfuran-2-ylidene)-2-phenylacetate |
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| PIN = Methyl (''E'')-(5-hydroxy-3-oxo-4-phenylfuran-2(3''H'')-ylidene)phenylacetate |
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| OtherNames = |
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| OtherNames = |
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| Section1 = {{Chembox Identifiers |
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| Section1 = {{Chembox Identifiers |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = 521-52-8 |
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| PubChem = 3033539 |
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| CASNo = 521-52-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 13N7RF6M84 |
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| PubChem = 54690323 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 463212 |
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| SMILES = COC(=O)/C(=C/1\C(=O)C(=C(O1)O)C2=CC=CC=C2)/C3=CC=CC=C3 |
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| SMILES = COC(=O)/C(=C/1\C(=O)C(=C(O1)O)C2=CC=CC=C2)/C3=CC=CC=C3 |
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|Section3={{Chembox Hazards |
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| GHSPictograms = {{GHS skull and crossbones}} |
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| MainHazards = toxic |
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'''Vulpinic acid''' is a ] first found in and important in the ] underlying the biology of ].<ref name="Spribille et al. 2016"/> It is a simple ] derivative of its parent compound, ], and a close relative of ], both of which derive from ]s such as ] via ]. The roles of vulpinic acid are not fully established, but may include properties that make it an ] for ]s. The compound is relatively toxic to mammals. |
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'''Vulpinic acid''' is a naturally occurring ] derivative found in several ] species, as well as some non-lichenized fungi. It was first isolated in 1925.<ref>{{cite journal | author = Mazza, Franc Paolo | title = Constitution and physical properties of vulpinic acid | journal = Rend. Accad. Sci. Napoli | year = 1925 | volume = 31 | pages = 182–90}}</ref> It is bright yellow, and relatively toxic. |
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==Chemical description== |
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==Occurrence in Lichen== |
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Vulpinic acid was first isolated from lichens in 1925.<ref name="Mazza 1925"/>{{primary source inline|date=January 2020}} As an isolated, purified substance, it is bright yellow in color.<ref name="Brodo et al. 2001"/> |
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Vulpinic acid is derived ] by ]ification from ];<ref>{{cite book | author = Crout, D.H.G. | date = 2012 | title = Carbocyclic Chemistry | volume = One | editor = Lloyd, D. | chapter = The Biosynthesis of Carbocyclic Compounds | pages = 63–198, esp. 147 | publisher = Springer Science & Business Media | isbn = 9781468482706 | url = https://www.google.com/search?hl=en&q=9781468482706 | access-date = January 3, 2020 }}</ref> ] itself derives from the aromatic amino acids ] and ], via ] and oxidative ring-cleavage of aryl]s, a process that also produces the related ]s.<ref name="Gill_Steglich">{{cite book | date = 1987 | volume = 51 | pages = 1–297 | pmid = 3315906 | doi = 10.1007/978-3-7091-6971-1_1 | isbn = 978-3-7091-7456-2 | last1 = Gill | first1 = M. | last2 = Steglich | first2 = W. | title = Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products | chapter = Pigments of Fungi (Macromycetes) }}{{Page range too broad|date=January 2020}}</ref>{{Page range too broad|date=January 2020}} |
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Together with ] and ], vulpinic acid is secondary metabolite of the fungi. It is speculated that the substances are used as repellent for some herbivores.<ref>{{cite journal | first = James D. | last = Lawrey | journal = The Bryologist | volume = 92 | issue = 3 | year = 1989 | pages = 326–328 |url = http://www.jstor.org/stable/3243401 | title = Lichen Secondary Compounds: Evidence for a Correspondence between Antiherbivore and Antimicrobial Function | doi = 10.2307/3243401 | publisher = The Bryologist, Vol. 92, No. 3}}</ref> The substance showed also some activity against gram-positive bacteria. <ref>{{cite journal |doi = 10.1017/S0024282992000574 |title = The Influence of pH and Lichen Metabolites (Vulpinic Acid and (+) Usnic Acid) on the Growth of the Lichen Photobiont Trebouxia Irregularis |year = 1998 |author = Bačkor, M. |journal = The Lichenologist |volume = 30 |pages = 577 |last2 = Hudá |first2 = J. |last3 = Repčák |first3 = M. |last4 = Ziegler§ |first4 = W. |last5 = Bačkorová |first5 = M.}}</ref> |
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There have been several ] reported for vulpinic acid. In one, ]s were efficiently functionalized by ] reactions via the corresponding ] ]s{{explanation needed|date=December 2020}}.<ref name="Ahmed & Langer2004"/> |
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==Occurrence in lichens == |
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]'', whose bright color is due in part to vulpinic acid.{{citation needed|date=January 2020}}]] |
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] is found in several ] species, as well as some non-lichenized fungi.<ref name="Mazza 1925"/>{{better source needed|date=January 2020}} It is a ] of the fungal partner in the lichen symbiosis.{{citation needed|date=January 2020}} It was found in the ] fungus '']''.<ref name="Duncan et al. 2003"/><ref name="Gill_Steglich"/> In 2016, a new group of ]s distinct from the well known lichen fungal partner was implicated in producing vulpinic acid.<ref name="Spribille et al. 2016"/> |
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==Bioactivities== |
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Vulpinic acid is relatively toxic to meat-eating mammals as well as insects and molluscs. However, it is not toxic to rabbits and mice. One ] of vulpinic acid may be as a repellent that lichens have evolved to deter grazing by ]s.<ref name="Nash 1996"/> Lichens may also exploit the ]-blocking properties of the molecule, protecting the underlying ]s.<ref name="Legouin et al. 2017"/> For example, vulpinic acid is thought to function as a blue light screen in '']''.<ref name="Phinney et al. 2018"/> It had been shown previously to protect ] in ] against ]-induced damage.<ref name="Varol et al. 2016"/> |
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Humans have exploited its mammalian toxicity, using lichens containing high amounts of the chemical (e.g., ''Letharia vulpina'') to poison wolves in Scandinavia, sometimes adding it to baits containing reindeer blood and glass.<ref name="Brodo et al. 2001"/> |
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Vulpinic acid has some ] activity against ], and has been shown to disrupt ] in ].<ref>{{cite journal | vauthors = Bačkor M, Hudá J, Repčák M, Ziegler W, Bačkorová M |doi = 10.1017/S0024282992000574 |title = The Influence of pH and Lichen Metabolites (Vulpinic Acid and (+)-Usnic Acid) on the Growth of the Lichen Photobiont ''Trebouxia irregularis'' |year = 1998 |journal = The Lichenologist |volume = 30 |pages = 577–582 |issue = 6}}</ref><ref>{{cite journal | vauthors = Shrestha G, Thompson A, Robison R, St Clair LL | title = ''Letharia vulpina'', a vulpinic acid containing lichen, targets cell membrane and cell division processes in methicillin-resistant ''Staphylococcus aureus'' | journal = Pharmaceutical Biology | volume = 54 | issue = 3 | pages = 413–8 | date = 28 April 2015 | pmid = 25919857 | doi = 10.3109/13880209.2015.1038754 | s2cid = 37962126 | url = https://www.researchgate.net/publication/275585357 }}</ref> |
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==See also== |
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* ] |
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==References== |
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==References== |
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{{Reflist|refs= |
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<ref name="Ahmed & Langer2004">{{cite journal |last1=Ahmed |first1=Zafar |last2=Langer |first2=Peter |title=Suzuki cross-coupling reactions of γ-alkylidenebutenolides: application to the synthesis of vulpinic acid |journal=Journal of Organic Chemistry |volume=69 |issue=11 |year=2004 |pages=3753–3757 |doi=10.1021/jo049780a|pmid=15153005 }}</ref> |
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<ref name="Brodo et al. 2001">{{cite book |first1=Irwin M. |last1=Brodo |first2=Sylvia Duran |last2=Sharnoff |first3=Stephen |last3=Sharnoff |title=Lichens of North America |year=2001 |publisher=Yale University Press |page=83 |isbn=978-0300082494}}</ref> |
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<ref name="Duncan et al. 2003">{{cite journal |last1=Duncan |first1=Christine J.G. |last2=Cuendet |first2=Muriel |last3=Fronczek |first3=Frank R. |last4=Pezzuto |first4=John M. |last5=Mehta |first5=Rajendra G. |last6=Hamann |first6=Mark T. |last7=Ross |first7=Samir A. |title=Chemical and biological investigation of the fungus ''Pulveroboletus ravenelii'' |journal=Journal of Natural Products |volume=66 |issue=1 |year=2003 |pages=103–107 |doi=10.1021/np0203990|pmid=12542354 |pmc=4969011 }}</ref> |
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<ref name="Legouin et al. 2017">{{cite journal |last1=Legouin |first1=Béatrice |last2=Lohézic-Le Dévéhat |first2=Françoise |last3=Ferron |first3=Solenn |last4=Rouaud |first4=Isabelle |last5=Le Pogam |first5=Pierre |last6=Cornevin |first6=Laurence |last7=Bertrand |first7=Michel |last8=Boustie |first8=Joël |title=Specialized metabolites of the lichen ''Vulpicida pinastri'' act as photoprotective agents |journal=Molecules |volume=22 |issue=7 |year=2017 |pages=1162 |doi=10.3390/molecules22071162 |pmid=28704942 |pmc=6152234|doi-access=free }}</ref> |
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<ref name="Mazza 1925">{{cite journal |last=Mazza |first=Franc Paolo |title=Constitution and physical properties of vulpinic acid |journal=Rendiconto dell'Accademia delle Scienze Napoli |year=1925 |volume=31 |pages=182–190}}</ref> |
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<ref name="Nash 1996">{{cite book |last1=Nash |first1=Thomas H. |title=Lichen Biology |url=https://books.google.com/books?id=P9y60ac0wbMC&pg=PA179 |year=1996 |publisher=Cambridge University Press |isbn=978-0-521-45974-7 |page=179}}</ref> |
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<ref name="Phinney et al. 2018">{{cite journal |last1=Phinney |first1=Nathan H. |last2=Gauslaa |first2=Yngvar |last3=Solhaug |first3=Knut Asbjørn |title=Why chartreuse? The pigment vulpinic acid screens blue light in the lichen ''Letharia vulpina'' |journal=Planta |volume=249 |issue=3 |year=2018 |pages=709–718 |doi=10.1007/s00425-018-3034-3|pmid=30374913 |s2cid=53102713 }}</ref> |
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<ref name="Spribille et al. 2016">{{cite journal |vauthors=Spribille T, Tuovinen V, Resl P, Vanderpool D, Wolinski H, Aime MC, Schneider K, Stabentheiner E, Toome-Heller M, Thor G, Mayrhofer H, Johannesson H, McCutcheon JP |display-authors=6 |title=Basidiomycete yeasts in the cortex of ascomycete macrolichens |journal=Science |volume=353 |issue=6298 |pages=488–492 |year=2016 |pmid=27445309 |pmc=5793994 |doi=10.1126/science.aaf8287 |bibcode=2016Sci...353..488S }}</ref> |
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<ref name="Varol et al. 2016">{{cite journal |last1=Varol |first1=Mehmet |last2=Türk |first2=Ayşen |last3=Candan |first3=Mehmet |last4=Tay |first4=Turgay |last5=Koparal |first5=Ayşe Tansu |title=Photoprotective activity of vulpinic and gyrophoric acids toward ultraviolet B-induced damage in human keratinocytes |journal=Phytotherapy Research |volume=30 |issue=1 |year=2016 |pages=9–15 |doi=10.1002/ptr.5493 |pmid=26463741|s2cid=206430748 }}</ref> |
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