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Phenolic Compounds from the Lichen Lobaria orientalis.

Dung M T Nguyen, Lien M T Do1,2, Vy T Nguyen

  • 1Department of Chemistry, Faculty of Science, Chulalongkorn University , Phayathai Road, Patumwan Bangkok 10330, Thailand.

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|February 10, 2017
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Researchers identified new compounds, lobarientalones and lobariethers, from the lichen Lobaria orientalis. This study also determined the absolute configuration of a key stereogenic center using electronic circular dichroism (ECD) spectroscopy.

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Area of Science:

  • Natural Product Chemistry
  • Lichenology
  • Organic Chemistry

Background:

  • Lichens are a source of diverse secondary metabolites.
  • Lobaria species are known to produce depsidones and diphenyl ethers.
  • Stereochemical assignment of lichen metabolites is crucial for understanding their biological activity.

Purpose of the Study:

  • To isolate and characterize new chemical constituents from Lobaria orientalis.
  • To determine the absolute configuration of the stereogenic acetal center in isolated compounds.
  • To propose a biosynthetic pathway for the identified metabolites.

Main Methods:

  • Extraction and isolation of compounds using ethyl acetate (EtOAc) solvent.
  • Structure elucidation using spectroscopic data, including electronic circular dichroism (ECD).
  • Comparison with analogous compounds for stereochemical determination.

Main Results:

  • Isolation of two new β-orcinol depsidones, lobarientalones A and B (1, 2).
  • Isolation of five new diphenyl ethers, lobariethers A-E (3-7).
  • First-time determination of the (1S) absolute configuration of the stereogenic acetal center via ECD spectroscopy.

Conclusions:

  • The chemical investigation of Lobaria orientalis yielded novel depsidones and diphenyl ethers.
  • Electronic circular dichroism (ECD) spectroscopy is a reliable method for assigning absolute configuration in these compounds.
  • A plausible biosynthetic route for the isolated compounds (1-8) was proposed based on co-occurrence.