Divaricatic acid

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Divaricatic acid
Divaricatic acid.svg
Names
IUPAC name
2-Hydroxy-4-(2-hydroxy-4-methoxy-6-propylbenzoyl)oxy-6-propylbenzoic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C21H24O7/c1-4-6-12-9-15(11-16(22)18(12)20(24)25)28-21(26)19-13(7-5-2)8-14(27-3)10-17(19)23/h8-11,22-23H,4-7H2,1-3H3,(H,24,25)
    Key: FSRDIJIAQPSMMR-UHFFFAOYSA-N
  • CCCC1=C(C(=CC(=C1)OC)O)C(=O)OC2=CC(=C(C(=C2)O)C(=O)O)CCC
Properties
C21H24O7
Molar mass 388.416 g·mol−1
AppearanceColorless crystalline needles
Melting point 129 °C (264 °F; 402 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Divaricatic acid is a chemical compound with the molecular formula C21H24O7. It is found in a variety of lichens, including some in the genera Evernia , [1] Lepraria , [2] and Ramalina . [3] It is classified as a depside.

Divaricatic acid forms colorless crystalline needles with a melting point of 129 °C. [4]

Divaricatic acid has antibacterial properties against some Gram positive bacteria, such as Bacillus subtilis , Staphylococcus epidermidis , Streptococcus mutans , and Enterococcus faecium . [5] Since it also has activity against methicillin-resistant Staphylococcus aureus (MRSA) with a potency equivalent to that of vancomycin, it has been suggested as a potential treatment for MRSA. [5] It also has molluscicidal activity against Biomphalaria glabrata (ram's horn snail) and antiparasitic activity against cercariae of Schistosoma mansoni (blood fluke). [6]

References

  1. ↑ Asahina, Yasuhiko; Hirakata, Teruo (1932). "Lichen substances. XV. Divaricatic acid". Berichte der Deutschen Chemischen Gesellschaft [Abteilung] B: Abhandlungen. 65B: 1665–1668. doi:10.1002/cber.19320651007.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  2. ↑ Lendemer, James C. (2011). "A taxonomic revision of the North American species of Lepraria s.l. That produce divaricatic acid, with notes on the type species of the genus L. Incana". Mycologia. 103 (6): 1216–1229. doi:10.3852/11-032. PMID   21642343.
  3. ↑ Moreira, Antônio; Braz-Filho, Raimundo; Mussi-Dias, Vicente; Vieira, Ivo (2015). "Chemistry and Biological Activity of Ramalina Lichenized Fungi". Molecules. 20 (5): 8952–8987. doi: 10.3390/molecules20058952 . PMC   6272487 . PMID   25996207.
  4. ↑ Hesse, O. (1897). "On lichen materials". Ber. Dtsch. Chem. Ges. 30: 357–366. doi:10.1002/cber.18970300172.
  5. 1 2 Oh, Jong Min; Kim, Yi Jeong; Gang, Hyo-Seung; Han, Jin; Ha, Hyung-Ho; Kim, Hoon (2018). "Antimicrobial Activity of Divaricatic Acid Isolated from the Lichen Evernia mesomorpha against Methicillin-Resistant Staphylococcus aureus". Molecules. 23 (12): 3068. doi: 10.3390/molecules23123068 . PMC   6320781 . PMID   30477128.
  6. ↑ Silva, H.A.M.F.; Siqueira, W.N.; Sá, J.L.F.; Silva, L.R.S; Martins, M.C.B.; Aires, A.L.; Amâncio, F.F.; Pereira, E.C.; Albuquerque, M.C.P.A; Melo, A.M.M.A.; Silva, N.H. (2018). "Laboratory assessment of divaricatic acid against Biomphalaria glabrata and Schistosoma mansoni cercariae". Acta Tropica. 178: 97–102. doi:10.1016/j.actatropica.2017.09.019. PMID   29097241.
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