A new polymorph of atranorin, a lichen paradepside

Liu, Yen‐Hsiang; Robbs, Steven L.; Fronczek, Frank R.; Watkins, Steven F.; Fischer, Nikolaus H.

doi:10.1107/s1600536802011856

Cited by 5 publications

(2 citation statements)

References 4 publications

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“…Unit cell measurements confirmed that these crystals were evernic acid. Unit cell of this compound is identical to that previously reported for atranorin by Liu et al . which accurately described the polymorph and compared this structure to the polymorph reported by Brassy et al .…”

Section: Resultssupporting

confidence: 77%

“…One polymorph with two phenyl groups forming 84(1)° was isolated from lichen Cladonia rangiformis Hoff . The second polymorph was identified after atranorin, purified from Cladonia prostrata , was recrystallized from ethyl acetate; the two phenolic rings in this atranorin polymorph form a dihedral angle of 60(3)° . It would be interesting to study whether atranorin and evernic acid polymorphs are produced in a species specific manner and to compare biological activities of polymorphs.…”

Section: Discussionmentioning

confidence: 99%

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Structure and Chemical Analysis of Major Specialized Metabolites Produced by the Lichen Evernia prunastri

Staples

LaDuca

Roze

et al. 2020

Chemistry & Biodiversity

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We performed comparative profiling of four specialized metabolites in the lichen Evernia prunastri, collected at three different geographic locations, California and Maine, USA, and Yoshkar Ola, Mari El, Russia. Among the compounds produced at high concentrations that were identified in all three specimens, evernic acid, usnic acid, lecanoric acid and chloroatranorin, evernic acid was the most abundant. Two depsidones, salazinic acid and physodic acid, were detected in the Yoshkar-Ola collection only. The crystalline structure of evernic acid (2hydroxy-4-[(2-hydroxy-4-methoxy-6-methylbenzoyl)oxy]-6-methylbenzoate) (hmb) revealed two crystallographically and conformationally distinct hmb anions, along with two monovalent sodium atoms. One hmb moiety contained an exotetradentate binding mode to sodium, whereas the other exhibited an exohexadentate binding mode to sodium. Embedded edge-sharing {Na 2 O 8 } n sodium-oxygen chains connected the hmb anions into the full three-dimensional crystal structure of the title compound. The crystal used for single-crystal X-ray diffraction exhibited non-merohedral twinning. The data suggest the importance of the acetyl-polymalonyl pathway products to processes of maintaining integrity of the lichen holobiont community.[a] Data for one replicate.

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Section: Resultssupporting

confidence: 77%

Section: Discussionmentioning

confidence: 99%