Lobaric acid

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Lobaric acid
Lobaric acid.svg
Names
IUPAC name
3-Hydroxy-9-methoxy-6-oxo-7-pentanoyl-1-pentylbenzo[b][1,4]benzodioxepine-2-carboxylic acid
Other names
Lobraric acid; stereocaulic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C25H28O8/c1-4-6-8-9-15-21(24(28)29)18(27)13-20-23(15)32-19-12-14(31-3)11-16(17(26)10-7-5-2)22(19)25(30)33-20/h11-13,27H,4-10H2,1-3H3,(H,28,29)
    Key: JHEWMLHQNRHTQX-UHFFFAOYSA-N
  • CCCCCC1=C(C(=CC2=C1OC3=CC(=CC(=C3C(=O)O2)C(=O)CCCC)OC)O)C(=O)O
Properties
C25H28O8
Molar mass 456.491 g·mol−1
Melting point 196–198 °C (385–388 °F; 469–471 K) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Lobaric acid is a chemical compound with the molecular formula C25H28O8. It has been found in the Antarctic lichen Stereocaulon alpinum [2] and a variety of other lichens. It is a member of the depsidone class of compounds.

The first total synthesis of lobaric acid was reported in 2018 by researchers at the Korea Polar Research Institute and Hanyang University. The synthesis was accomplished in 14 total steps, starting with 4-bromophthalic anhydride. Key steps included an Ullmann aryl ether coupling reaction to connect the two main aromatic rings, followed by a seven-membered lactonization reaction to form the final structure. The synthetic route also allowed access to several derivatives of lobaric acid, including methyllobarin, lobarin, and lobarstin, which showed significant protein tyrosine phosphatase 1B (PTP1B) inhibitory activities. [3]

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References

  1. Morita, Hiroshi; Tsuchiya, Tomoe; Kishibe, Koji; Noya, Sayaka; Shiro, Motoo; Hirasawa, Yusuke (2009). "Antimitotic activity of lobaric acid and a new benzofuran, sakisacaulon a from Stereocaulon sasakii". Bioorganic & Medicinal Chemistry Letters. 19 (13): 3679–3681. doi:10.1016/j.bmcl.2009.03.170. PMID   19481447.
  2. Tian, Yuan; Li, Yan-Ling; Zhao, Feng-Chun (2017). "Secondary Metabolites from Polar Organisms". Marine Drugs. 15 (3): 28. doi: 10.3390/md15030028 . PMC   5367009 . PMID   28241505.
  3. Kim, Tai Kyoung; Kim, Joung Eun; Youn, Ui Joung; Han, Se Jong; Kim, Il-Chan; Cho, Cheon-Gyu; Yim, Joung Han (2018). "Total Syntheses of Lobaric Acid and Its Derivatives from the Antarctic Lichen Stereocaulon alpinum". Journal of Natural Products. 81 (6): 1460–1467. doi:10.1021/acs.jnatprod.8b00227. PMID   29878768.