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From the mycelial extracts of a 70\u2005L scale fermentation of this strain we additionally isolated nine new macrolides (<jats:bold>1<\/jats:bold>\u2013<jats:bold>9<\/jats:bold>) by RP\u2010HPLC. The planar structures were elucidated by NMR spectroscopy complemented by HR\u2010ESIMS. The relative configurations were assigned by <jats:italic>J<\/jats:italic>\u2010based configuration analyses and confirmed by Kishi\u2032s Universal Database. Subsequently, the absolute configurations were assigned by Mosher\u2032s method using the shift analysis of a tetra\u2010MTPA derivative. For rickiol\u2005A\u2005(<jats:bold>1<\/jats:bold>) and E\u2005(<jats:bold>5<\/jats:bold>) we observed transesterification of 20\u2010membered ring structures to 22\u2010membered isomers rickiol\u2005A2\u2005(<jats:bold>6<\/jats:bold>) and E2\u2005(<jats:bold>7<\/jats:bold>), and to 24\u2010membered isomers rickiol\u2005A3\u2005(<jats:bold>8<\/jats:bold>) and rickiol\u2005E3\u2005(<jats:bold>9<\/jats:bold>), respectively. Cytotoxic effects and moderate antibiotic activity against Gram\u2010positive bacteria were observed for <jats:bold>1<\/jats:bold>\u2013<jats:bold>8<\/jats:bold> and <jats:bold>1<\/jats:bold>\u2013<jats:bold>6<\/jats:bold> and <jats:bold>8<\/jats:bold>, respectively. The total synthesis of rickiol\u2005E3\u2005(<jats:bold>9<\/jats:bold>) established easier access to these compounds.<\/jats:p>","DOI":"10.1002\/chem.201704928","type":"journal-article","created":{"date-parts":[[2017,11,23]],"date-time":"2017-11-23T08:33:12Z","timestamp":1511425992000},"page":"2200-2213","source":"Crossref","is-referenced-by-count":30,"title":["The Rickiols: 20\u2010, 22\u2010, and 24\u2010membered Macrolides from the Ascomycete <i>Hypoxylon rickii<\/i>"],"prefix":"10.1002","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5234-8525","authenticated-orcid":false,"given":"Frank","family":"Surup","sequence":"first","affiliation":[{"name":"Microbial Drugs Helmholtz Centre for Infection Research GmbH (HZI)  Inhoffenstra\u00dfe 7 38124 Braunschweig Germany"},{"name":"Partner site Hannover-Braunschweig German Centre for Infection Research Association (DZIF)  Inhoffenstra\u00dfe 7 38124 Braunschweig Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0443-9091","authenticated-orcid":false,"given":"Eric","family":"Kuhnert","sequence":"additional","affiliation":[{"name":"Microbial Drugs Helmholtz Centre for Infection Research GmbH (HZI)  Inhoffenstra\u00dfe 7 38124 Braunschweig Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Andreas","family":"B\u00f6hm","sequence":"additional","affiliation":[{"name":"Institute for Organic Chemistry Leibniz Universit\u00e4t Hannover  Schneiderberg 1B 30167 Hannover Germany"},{"name":"Drug Research (BMWZ) Leibniz Universit\u00e4t Hannover  Schneiderberg 1B 30167 Hannover Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tim","family":"Pendzialek","sequence":"additional","affiliation":[{"name":"Institute for Organic Chemistry Leibniz Universit\u00e4t Hannover  Schneiderberg 1B 30167 Hannover Germany"},{"name":"Drug Research (BMWZ) Leibniz Universit\u00e4t Hannover  Schneiderberg 1B 30167 Hannover Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Danny","family":"Solga","sequence":"additional","affiliation":[{"name":"Institute for Organic Chemistry Leibniz Universit\u00e4t Hannover  Schneiderberg 1B 30167 Hannover Germany"},{"name":"Drug Research (BMWZ) Leibniz Universit\u00e4t Hannover  Schneiderberg 1B 30167 Hannover Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Vincent","family":"Wiebach","sequence":"additional","affiliation":[{"name":"Microbial Drugs Helmholtz Centre for Infection Research GmbH (HZI)  Inhoffenstra\u00dfe 7 38124 Braunschweig Germany"},{"name":"Institut f\u00fcr Chemie Technische Universit\u00e4t Berlin  M\u00fcller-Breslau-Stra\u00dfe 10 10623 Berlin Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Hauke","family":"Engler","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Organic Chemistry Cologne University  Greinstra\u00dfe 4 50939 Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0470-7428","authenticated-orcid":false,"given":"Albrecht","family":"Berkessel","sequence":"additional","affiliation":[{"name":"Department of Chemistry, Organic Chemistry Cologne University  Greinstra\u00dfe 4 50939 Cologne Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7284-8671","authenticated-orcid":false,"given":"Marc","family":"Stadler","sequence":"additional","affiliation":[{"name":"Microbial Drugs Helmholtz Centre for Infection Research GmbH (HZI)  Inhoffenstra\u00dfe 7 38124 Braunschweig Germany"},{"name":"Partner site Hannover-Braunschweig German Centre for Infection Research Association (DZIF)  Inhoffenstra\u00dfe 7 38124 Braunschweig Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4858-3957","authenticated-orcid":false,"given":"Markus","family":"Kalesse","sequence":"additional","affiliation":[{"name":"Institute for Organic Chemistry Leibniz Universit\u00e4t Hannover  Schneiderberg 1B 30167 Hannover Germany"},{"name":"Drug Research (BMWZ) Leibniz Universit\u00e4t Hannover  Schneiderberg 1B 30167 Hannover Germany"},{"name":"Medicinal Chemistry Helmholtz Centre for Infection Research GmbH (HZI)  Inhoffenstra\u00dfe 7 38124 Braunschweig Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2018,1,19]]},"reference":[{"key":"e_1_2_7_1_1","first-page":"1","volume-title":"Macrolide Antibiotics\u2014Chemistry, Biology, and Practice","author":"Shiomi K.","year":"2002"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00253-009-2326-8"},{"key":"e_1_2_7_3_1","unstructured":"L. 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