{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,11,1]],"date-time":"2025-11-01T17:20:20Z","timestamp":1762017620248,"version":"build-2065373602"},"reference-count":46,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2020,1,10]],"date-time":"2020-01-10T00:00:00Z","timestamp":1578614400000},"content-version":"vor","delay-in-days":9,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry &amp; Biodiversity"],"published-print":{"date-parts":[[2020,1]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>We performed comparative profiling of four specialized metabolites in the lichen <jats:italic>Evernia prunastri<\/jats:italic>, 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\u2010Ola collection only. The crystalline structure of evernic acid (2\u2010hydroxy\u20104\u2010[(2\u2010hydroxy\u20104\u2010methoxy\u20106\u2010methylbenzoyl)oxy]\u20106\u2010methylbenzoate) (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\u2010sharing {Na<jats:sub>2<\/jats:sub>O<jats:sub>8<\/jats:sub>}<jats:sub><jats:italic>n<\/jats:italic><\/jats:sub> sodium\u2010oxygen chains connected the hmb anions into the full three\u2010dimensional crystal structure of the title compound. The crystal used for single\u2010crystal X\u2010ray diffraction exhibited non\u2010merohedral twinning. The data suggest the importance of the acetyl\u2010polymalonyl pathway products to processes of maintaining integrity of the lichen holobiont community.<\/jats:p>","DOI":"10.1002\/cbdv.201900465","type":"journal-article","created":{"date-parts":[[2019,11,8]],"date-time":"2019-11-08T03:10:57Z","timestamp":1573182657000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Structure and Chemical Analysis of Major Specialized Metabolites Produced by the Lichen <i>Evernia prunastri<\/i>"],"prefix":"10.1002","volume":"17","author":[{"given":"Richard","family":"Staples","sequence":"first","affiliation":[{"name":"Department of Chemistry Michigan State University  East Lansing MI 48824 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Robert L.","family":"LaDuca","sequence":"additional","affiliation":[{"name":"Department of Chemistry Michigan State University  East Lansing MI 48824 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0184-0805","authenticated-orcid":false,"given":"Ludmila V.","family":"Roze","sequence":"additional","affiliation":[{"name":"Plant Biology Laboratories, Department of Plant Biology Michigan State University  612 Wilson Road, Room 342 East Lansing MI 48824 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Maris","family":"Laivenieks","sequence":"additional","affiliation":[{"name":"Plant Biology Laboratories, Department of Plant Biology Michigan State University  612 Wilson Road, Room 342 East Lansing MI 48824 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"John E.","family":"Linz","sequence":"additional","affiliation":[{"name":"Department of Food Science and Human Nutrition Michigan State University  East Lansing MI 48824 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Randolph","family":"Beaudry","sequence":"additional","affiliation":[{"name":"Department of Horticulture Michigan State University  East Lansing MI 48824 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Alan","family":"Fryday","sequence":"additional","affiliation":[{"name":"Plant Biology Laboratories, Department of Plant Biology Michigan State University  612 Wilson Road, Room 342 East Lansing MI 48824 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Anthony L.","family":"Schilmiller","sequence":"additional","affiliation":[{"name":"RTSF Mass Spectrometry and Metabolomics Core Michigan State University  East Lansing MI 48824 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Anna V.","family":"Koptina","sequence":"additional","affiliation":[{"name":"Division of Pharmacognosy, Department of Medicinal Chemistry Uppsala University  Uppsala 75123 Sweden"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Benjamin","family":"Smith","sequence":"additional","affiliation":[{"name":"Plant Biology Laboratories, Department of Plant Biology Michigan State University  612 Wilson Road, Room 342 East Lansing MI 48824 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Frances","family":"Trail","sequence":"additional","affiliation":[{"name":"Plant Biology Laboratories, Department of Plant Biology Michigan State University  612 Wilson Road, Room 342 East Lansing MI 48824 USA"},{"name":"Department of Plant, Soil and Microbial Sciences Michigan State University  East Lansing MI 48824 USA"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,1,10]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1038\/ismej.2014.138"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.5582\/ddt.8.84"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1639\/0007-2745(2003)106[0080:LFIEAB]2.0.CO;2"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1371\/journal.pone.0120768"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1126\/science.aaf8287"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/B606983P"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13199-014-0278-y"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2016.00180"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1038\/nchembio.1897"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.2307\/3243401"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1017\/S0024282992000574"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1055\/s-0042-105571"},{"key":"e_1_2_8_13_1","doi-asserted-by":"crossref","unstructured":"K.\u2005A. 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