Vulpinic acid

Vulpinic acid
Names
IUPAC name
Methyl (2E)-2-(5-hydroxy-3-oxo-4-phenylfuran-2-ylidene)-2-phenylacetate
Identifiers
3D model (JSmol)
ChEMBL
ECHA InfoCard 100.007.560
Properties
C19H14O5
Molar mass 322.32 g·mol−1
Hazards
Main hazards toxic
GHS pictograms
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Vulpinic acid is a naturally occurring methyl ester derivative of pulvinic acid found in several lichen species, as well as some non-lichenized fungi. It was first isolated in 1925.[1] It is bright yellow, and relatively toxic.

Occurrence in lichens

The lichen Letharia vulpina gets its bright yellow color from vulpinic acid.

Vulpinic acid was first isolated from lichens, and is a secondary metabolite of the fungal partner.[2] It is speculated that vulpinic acid's biological function is as a repellent for some herbivores. Humans have also exploited this toxicity by using lichens that contain high amounts of the chemical (such as Letharia vulpina) as poison for wolves and foxes.[3][4] The substance showed also some antibacterial activity against gram-positive bacteria and has even been shown to disrupt cell division in MRSA.[5][6] It was also found in Pulveroboletus ravenelii (Berk. & Curt.) Murrill.[7][8]

See also

References

  1. ↑ Mazza, Franc Paolo (1925). "Constitution and physical properties of vulpinic acid". Rend. Accad. Sci. Napoli. 31: 182–90.
  2. ↑ "Twelve Readings on the Lichen Thallus".
  3. ↑ Lawrey, James D. (1989). "Lichen Secondary Compounds: Evidence for a Correspondence between Antiherbivore and Antimicrobial Function". The Bryologist. The Bryologist, Vol. 92, No. 3. 92 (3): 326&ndash, 328. doi:10.2307/3243401. JSTOR 3243401.
  4. ↑ Galun, Margalith (1988). CRC handbook of lichenology. Boca Raton, Fla.: CRC Press. ISBN 0-8493-3583-3.
  5. ↑ 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.
  6. ↑ Shrestha, Gajendra; Thompson, Andrew; Robison, Richard; St. Clair, Larry L. (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): 413–418. doi:10.3109/13880209.2015.1038754.
  7. ↑ Gruber, Gertraud (2002). Isolierung und Strukturaufklär ung von chemotaxonomisch relevanten Sekundärmetabolit en aus höheren Pilzen, insbesondere aus der Ordnung der Boletales (PDF) (PhD). Ludwig Maximilian University of Munich.
  8. ↑ Gill, M.; Steglich, W. (1987). "Pigments of fungi (Macromycetes)". Prog Chem Org Nat Prod. 51: 1–297. doi:10.1007/978-3-7091-6971-1_1. ISBN 978-3-7091-6971-1.


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