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

Autor: Staples R; Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA., LaDuca RL; Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA., Roze LV; Plant Biology Laboratories, Department of Plant Biology, Michigan State University, 612 Wilson Road, Room 342, East Lansing, MI 48824, USA., Laivenieks M; Plant Biology Laboratories, Department of Plant Biology, Michigan State University, 612 Wilson Road, Room 342, East Lansing, MI 48824, USA., Linz JE; Department of Food Science and Human Nutrition, Michigan State University, East Lansing, MI 48824, USA., Beaudry R; Department of Horticulture, Michigan State University, East Lansing, MI 48824, USA., Fryday A; Plant Biology Laboratories, Department of Plant Biology, Michigan State University, 612 Wilson Road, Room 342, East Lansing, MI 48824, USA., Schilmiller AL; RTSF Mass Spectrometry and Metabolomics Core, Michigan State University, East Lansing, MI 48824, USA., Koptina AV; Division of Pharmacognosy, Department of Medicinal Chemistry, Uppsala University, Uppsala, 75123, Sweden., Smith B; Plant Biology Laboratories, Department of Plant Biology, Michigan State University, 612 Wilson Road, Room 342, East Lansing, MI 48824, USA., Trail F; Plant Biology Laboratories, Department of Plant Biology, Michigan State University, 612 Wilson Road, Room 342, East Lansing, MI 48824, USA.; Department of Plant, Soil and Microbial Sciences, Michigan State University, East Lansing, MI 48824, USA.
Jazyk: angličtina
Zdroj: Chemistry & biodiversity [Chem Biodivers] 2020 Jan; Vol. 17 (1), pp. e1900465. Date of Electronic Publication: 2020 Jan 10.
DOI: 10.1002/cbdv.201900465
Abstrakt: 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 (2-hydroxy-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.
(© 2019 Wiley-VHCA AG, Zurich, Switzerland.)
Databáze: MEDLINE
Externí odkaz: