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{{short description|Chemical compound}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 385704022
| Name = Vulpinic acid | Name = Vulpinic acid
| ImageFileL1 = Vulpinic acid.png | ImageFileL1 = Vulpinic acid Structural Formula V1.svg
| ImageSizeL1 = 125px | ImageSizeL1 = 125px
| ImageFileR1 = Vulpinic acid.jpg | ImageFileR1 = Vulpinic acid - 3D - Ball-and-stick Model.png
| ImageSizeR1 = 125px | ImageSizeR1 = 125px
| ImageNameL1 = Chemical structure of vulpinic acid | ImageNameL1 = Chemical structure of vulpinic acid
| IUPACName = Methyl (2''E'')-2-(5-hydroxy-3-oxo-4-phenylfuran-2-ylidene)-2-phenylacetate | PIN = Methyl (''E'')-(5-hydroxy-3-oxo-4-phenylfuran-2(3''H'')-ylidene)phenylacetate
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo = 521-52-8
| PubChem = 3033539 | CASNo = 521-52-8
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 13N7RF6M84
| PubChem = 54690323
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 463212
| SMILES = COC(=O)/C(=C/1\C(=O)C(=C(O1)O)C2=CC=CC=C2)/C3=CC=CC=C3 | SMILES = COC(=O)/C(=C/1\C(=O)C(=C(O1)O)C2=CC=CC=C2)/C3=CC=CC=C3
}} }}
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| BoilingPt = | BoilingPt =
}} }}
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS skull and crossbones}}
| MainHazards = toxic
| FlashPt =
| AutoignitionPt = }}
}} }}


'''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.
'''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.


==Chemical description==
⚫ ==Occurrence in Lichen==
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"/>


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}}
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&ndash;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>

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"/>

⚫ ==Occurrence in lichens ==
]'', whose bright color is due in part to vulpinic acid.{{citation needed|date=January 2020}}]]

] 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"/>

==Bioactivities==
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"/>

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"/>

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>

==See also==
* ]


==References== ==References==
{{Reflist|refs=
{{reflist}}


<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>
⚫ ]
⚫ ]
⚫ ]


<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>


<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>
{{organic-compound-stub}}


<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>
]

<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>

<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>

<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>

<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>

<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>

}}

⚫ ]
⚫ ]
]
⚫ ]
]

Latest revision as of 08:17, 17 November 2024

Chemical compound
Vulpinic acid
Chemical structure of vulpinic acid
Chemical structure of vulpinic acid
Names
Preferred IUPAC name Methyl (E)-(5-hydroxy-3-oxo-4-phenylfuran-2(3H)-ylidene)phenylacetate
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.007.560 Edit this at Wikidata
PubChem CID
UNII
SMILES
  • COC(=O)/C(=C/1\C(=O)C(=C(O1)O)C2=CC=CC=C2)/C3=CC=CC=C3
Properties
Chemical formula C19H14O5
Molar mass 322.316 g·mol
Hazards
Occupational safety and health (OHS/OSH):
Main hazards toxic
GHS labelling:
Pictograms GHS06: Toxic
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Vulpinic acid is a natural product first found in and important in the symbiosis underlying the biology of lichens. It is a simple methyl ester derivative of its parent compound, pulvinic acid, and a close relative of pulvinone, both of which derive from aromatic amino acids such as phenylalanine via secondary metabolism. The roles of vulpinic acid are not fully established, but may include properties that make it an antifeedant for herbivores. The compound is relatively toxic to mammals.

Chemical description

Vulpinic acid was first isolated from lichens in 1925. As an isolated, purified substance, it is bright yellow in color.

Vulpinic acid is derived biosynthetically by esterification from pulvinic acid; pulvinate itself derives from the aromatic amino acids phenylalanine and tyrosine, via dimerization and oxidative ring-cleavage of arylpyruvic acids, a process that also produces the related pulvinones.

There have been several chemical syntheses reported for vulpinic acid. In one, butenolides were efficiently functionalized by Suzuki cross-coupling reactions via the corresponding enol triflates.

Occurrence in lichens

The lichen Letharia vulpina, whose bright color is due in part to vulpinic acid.

Pulvinic acid is found in several lichen species, as well as some non-lichenized fungi. It is a secondary metabolite of the fungal partner in the lichen symbiosis. It was found in the bolete fungus Pulveroboletus ravenelii. In 2016, a new group of basidiomycetes distinct from the well known lichen fungal partner was implicated in producing vulpinic acid.

Bioactivities

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 biological function of vulpinic acid may be as a repellent that lichens have evolved to deter grazing by herbivores. Lichens may also exploit the ultraviolet-blocking properties of the molecule, protecting the underlying photobionts. For example, vulpinic acid is thought to function as a blue light screen in Letharia vulpina. It had been shown previously to protect human skin cells in tissue culture against ultraviolet B-induced damage.

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.

Vulpinic acid has some antibacterial activity against gram-positive bacteria, and has been shown to disrupt cell division in MRSA.

See also

References

  1. ^ Spribille T, Tuovinen V, Resl P, Vanderpool D, Wolinski H, Aime MC, et al. (2016). "Basidiomycete yeasts in the cortex of ascomycete macrolichens". Science. 353 (6298): 488–492. Bibcode:2016Sci...353..488S. doi:10.1126/science.aaf8287. PMC 5793994. PMID 27445309.
  2. ^ Mazza, Franc Paolo (1925). "Constitution and physical properties of vulpinic acid". Rendiconto dell'Accademia delle Scienze Napoli. 31: 182–190.
  3. ^ Brodo, Irwin M.; Sharnoff, Sylvia Duran; Sharnoff, Stephen (2001). Lichens of North America. Yale University Press. p. 83. ISBN 978-0300082494.
  4. Crout, D.H.G. (2012). "The Biosynthesis of Carbocyclic Compounds". In Lloyd, D. (ed.). Carbocyclic Chemistry. Vol. One. Springer Science & Business Media. pp. 63–198, esp. 147. ISBN 9781468482706. Retrieved January 3, 2020.
  5. ^ Gill, M.; Steglich, W. (1987). "Pigments of Fungi (Macromycetes)". Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products. Vol. 51. pp. 1–297. doi:10.1007/978-3-7091-6971-1_1. ISBN 978-3-7091-7456-2. PMID 3315906.
  6. Ahmed, Zafar; Langer, Peter (2004). "Suzuki cross-coupling reactions of γ-alkylidenebutenolides: application to the synthesis of vulpinic acid". Journal of Organic Chemistry. 69 (11): 3753–3757. doi:10.1021/jo049780a. PMID 15153005.
  7. Duncan, Christine J.G.; Cuendet, Muriel; Fronczek, Frank R.; Pezzuto, John M.; Mehta, Rajendra G.; Hamann, Mark T.; Ross, Samir A. (2003). "Chemical and biological investigation of the fungus Pulveroboletus ravenelii". Journal of Natural Products. 66 (1): 103–107. doi:10.1021/np0203990. PMC 4969011. PMID 12542354.
  8. Nash, Thomas H. (1996). Lichen Biology. Cambridge University Press. p. 179. ISBN 978-0-521-45974-7.
  9. Legouin, Béatrice; Lohézic-Le Dévéhat, Françoise; Ferron, Solenn; Rouaud, Isabelle; Le Pogam, Pierre; Cornevin, Laurence; Bertrand, Michel; Boustie, Joël (2017). "Specialized metabolites of the lichen Vulpicida pinastri act as photoprotective agents". Molecules. 22 (7): 1162. doi:10.3390/molecules22071162. PMC 6152234. PMID 28704942.
  10. Phinney, Nathan H.; Gauslaa, Yngvar; Solhaug, Knut Asbjørn (2018). "Why chartreuse? The pigment vulpinic acid screens blue light in the lichen Letharia vulpina". Planta. 249 (3): 709–718. doi:10.1007/s00425-018-3034-3. PMID 30374913. S2CID 53102713.
  11. Varol, Mehmet; Türk, Ayşen; Candan, Mehmet; Tay, Turgay; Koparal, Ayşe Tansu (2016). "Photoprotective activity of vulpinic and gyrophoric acids toward ultraviolet B-induced damage in human keratinocytes". Phytotherapy Research. 30 (1): 9–15. doi:10.1002/ptr.5493. PMID 26463741. S2CID 206430748.
  12. Bačkor M, Hudá J, Repčák M, Ziegler W, Bačkorová M (1998). "The Influence of pH and Lichen Metabolites (Vulpinic Acid and (+)-Usnic Acid) on the Growth of the Lichen Photobiont Trebouxia irregularis". The Lichenologist. 30 (6): 577–582. doi:10.1017/S0024282992000574.
  13. Shrestha G, Thompson A, Robison R, St Clair LL (28 April 2015). "Letharia vulpina, a vulpinic acid containing lichen, targets cell membrane and cell division processes in methicillin-resistant Staphylococcus aureus". Pharmaceutical Biology. 54 (3): 413–8. doi:10.3109/13880209.2015.1038754. PMID 25919857. S2CID 37962126.
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