{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,2]],"date-time":"2025-12-02T18:06:11Z","timestamp":1764698771747,"version":"build-2065373602"},"reference-count":44,"publisher":"Wiley","issue":"11","license":[{"start":{"date-parts":[[2020,3,13]],"date-time":"2020-03-13T00:00:00Z","timestamp":1584057600000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by-nc\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["SP718\/4-1"],"award-info":[{"award-number":["SP718\/4-1"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2020,6,2]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Mycenarubin\u2005C, a previously unknown red pyrroloquinoline alkaloid, was isolated from fruiting bodies of the mushroom <jats:italic>Mycena rosea<\/jats:italic> and its structure was elucidated mainly by NMR spectroscopy and mass spectrometry. Unlike mycenarubin\u2005A, the major pyrroloquinoline alkaloid in fruiting bodies of <jats:italic>M.\u2005rosea<\/jats:italic>, mycenarubin\u2005C, contains an eight\u2010membered ring with an additional C<jats:sub>1<\/jats:sub> unit that is hitherto unprecedented for pyrroloquinoline alkaloids known in nature. Incubation of mycenarubin\u2005A with an excess of formaldehyde revealed that mycenarubin\u2005C was generated nearly quantitatively from mycenarubin\u2005A. An investigation into the formaldehyde content of fresh fruiting bodies of <jats:italic>M.\u2005rosea<\/jats:italic> showed the presence of considerable amounts of formaldehyde, with values of 5\u2005\u03bcg per gram of fresh weight in fresh fruiting bodies. Although mycenarubin\u2005C did not show bioactivity against selected bacteria and fungi, formaldehyde inhibits the growth of the mycoparasite <jats:italic>Spinellus fusiger<\/jats:italic> at concentrations present in fruiting bodies of <jats:italic>M.\u2005rosea<\/jats:italic>. Therefore, formaldehyde might play an ecological role in the chemical defence of <jats:italic>M.\u2005rosea<\/jats:italic> against <jats:italic>S.\u2005fusiger<\/jats:italic>. In turn, <jats:italic>S.\u2005fusiger<\/jats:italic> produces gallic acid\u2014presumably to detoxify formaldehyde by reaction of this aldehyde with amino acids and gallic acid to Mannich adducts.<\/jats:p>","DOI":"10.1002\/cbic.201900733","type":"journal-article","created":{"date-parts":[[2020,1,23]],"date-time":"2020-01-23T15:10:10Z","timestamp":1579792210000},"page":"1613-1620","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":13,"title":["Formaldehyde as a Chemical Defence Agent of Fruiting Bodies of <i>Mycena rosea<\/i> and its Role in the Generation of the Alkaloid Mycenarubin\u2005C"],"prefix":"10.1002","volume":"21","author":[{"given":"Rieke","family":"Himstedt","sequence":"first","affiliation":[{"name":"Institut f\u00fcr Organische und Analytische Chemie Universit\u00e4t Bremen  Leobener Strasse 7 28359 Bremen Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Silke","family":"Wagner","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Organische und Analytische Chemie Universit\u00e4t Bremen  Leobener Strasse 7 28359 Bremen Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Robert J. R.","family":"Jaeger","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Organische und Analytische Chemie Universit\u00e4t Bremen  Leobener Strasse 7 28359 Bremen Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Mich\u00e8le\u2010Laure","family":"Lieunang Watat","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Organische und Analytische Chemie Universit\u00e4t Bremen  Leobener Strasse 7 28359 Bremen Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Jana","family":"Backenk\u00f6hler","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Organische und Analytische Chemie Universit\u00e4t Bremen  Leobener Strasse 7 28359 Bremen Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zeljka","family":"Rupcic","sequence":"additional","affiliation":[{"name":"Mikrobielle Wirkstoffe Helmholtz-Zentrum f\u00fcr Infektionsforschung  Inhoffenstrasse 7 38124 Braunschweig 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":"Mikrobielle Wirkstoffe Helmholtz-Zentrum f\u00fcr Infektionsforschung  Inhoffenstrasse 7 38124 Braunschweig Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2916-4319","authenticated-orcid":false,"given":"Peter","family":"Spiteller","sequence":"additional","affiliation":[{"name":"Institut f\u00fcr Organische und Analytische Chemie Universit\u00e4t Bremen  Leobener Strasse 7 28359 Bremen Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2020,3,13]]},"reference":[{"key":"e_1_2_7_1_1","first-page":"123","volume-title":"Mycena d'Europa","author":"Robich G.","year":"2003"},{"key":"e_1_2_7_2_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200600826"},{"key":"e_1_2_7_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/b407299p"},{"key":"e_1_2_7_4_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4039(01)80439-1"},{"key":"e_1_2_7_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/np50076a038"},{"key":"e_1_2_7_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00376a096"},{"key":"e_1_2_7_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo00303a043"},{"key":"e_1_2_7_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00058a003"},{"key":"e_1_2_7_9_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.200700739"},{"key":"e_1_2_7_10_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201800235"},{"key":"e_1_2_7_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/np070179s"},{"key":"e_1_2_7_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.5b00942"},{"key":"e_1_2_7_13_1","first-page":"46","volume-title":"Frontiers of Flavour Science","author":"Talou T.","year":"2000"},{"key":"e_1_2_7_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100248a015"},{"key":"e_1_2_7_15_1","doi-asserted-by":"publisher","DOI":"10.1002\/ejoc.201800417"},{"key":"e_1_2_7_16_1","unstructured":"J.\u2005W. Munch D.\u2005J. Munch S.\u2005D. Winslow S.\u2005C. Wendelken B.\u2005V. Pepich Method\u2005556 Determination of Carbonyl Compounds in Drinking Water by Pentafluorobenzylhydroxylamine Derivatization and Capillary Gas Chromatography with Electron Capture Detection United States Environmental Protection Agency Cincinnati 1998 pp.\u20051\u201337."},{"key":"e_1_2_7_17_1","doi-asserted-by":"publisher","DOI":"10.1080\/02652030400013326"},{"key":"e_1_2_7_18_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.talanta.2004.07.037"},{"key":"e_1_2_7_19_1","doi-asserted-by":"publisher","DOI":"10.1080\/02652030903081929"},{"key":"e_1_2_7_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf00100a015"},{"key":"e_1_2_7_21_1","doi-asserted-by":"publisher","DOI":"10.1271\/bbb1961.44.1391"},{"key":"e_1_2_7_22_1","doi-asserted-by":"publisher","DOI":"10.1006\/fstl.1997.0248"},{"key":"e_1_2_7_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.fgb.2012.09.001"},{"key":"e_1_2_7_24_1","doi-asserted-by":"publisher","DOI":"10.3109\/10408419409113545"},{"key":"e_1_2_7_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0079-6468(08)70107-3"},{"key":"e_1_2_7_26_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.200800292"},{"key":"e_1_2_7_27_1","doi-asserted-by":"publisher","DOI":"10.1039\/C4NP00166D"},{"volume-title":"Pilze auf Pilzfruchtk\u00f6rpern","year":"1991","author":"Helfer W.","key":"e_1_2_7_28_1"},{"key":"e_1_2_7_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/jf00035a014"},{"key":"e_1_2_7_30_1","doi-asserted-by":"publisher","DOI":"10.1021\/np960040"},{"key":"e_1_2_7_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.8278"},{"key":"e_1_2_7_32_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.foodchem.2005.09.089"},{"key":"e_1_2_7_33_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo971176v"},{"key":"e_1_2_7_34_1","doi-asserted-by":"publisher","DOI":"10.1002\/hlca.19580410703"},{"key":"e_1_2_7_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2013.07.027"},{"key":"e_1_2_7_36_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bjp.2016.08.008"},{"key":"e_1_2_7_37_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.7b00764"},{"key":"e_1_2_7_38_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.steroids.2018.03.007"},{"key":"e_1_2_7_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytochem.2019.01.008"},{"key":"e_1_2_7_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/es00008a009"},{"key":"e_1_2_7_41_1","unstructured":"German Norm for Calibration: DIN 3840251A."},{"key":"e_1_2_7_42_1","doi-asserted-by":"publisher","DOI":"10.1021\/es00094a002"},{"key":"e_1_2_7_43_1","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1002\/9783527624508","volume-title":"Qualit\u00e4tssicherung in der Analytischen Chemie","author":"Funk W.","year":"2005"},{"key":"e_1_2_7_44_1","doi-asserted-by":"publisher","DOI":"10.5642\/aliso.20082601.08"}],"container-title":["ChemBioChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcbic.201900733","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbic.201900733","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/cbic.201900733","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbic.201900733","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T09:18:22Z","timestamp":1760260702000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cbic.201900733"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,3,13]]},"references-count":44,"journal-issue":{"issue":"11","published-print":{"date-parts":[[2020,6,2]]}},"alternative-id":["10.1002\/cbic.201900733"],"URL":"https:\/\/doi.org\/10.1002\/cbic.201900733","archive":["Portico"],"relation":{},"ISSN":["1439-4227","1439-7633"],"issn-type":[{"type":"print","value":"1439-4227"},{"type":"electronic","value":"1439-7633"}],"subject":[],"published":{"date-parts":[[2020,3,13]]},"assertion":[{"value":"2019-12-04","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2020-03-13","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}