{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,13]],"date-time":"2026-06-13T12:29:45Z","timestamp":1781353785860,"version":"3.54.1"},"reference-count":29,"publisher":"Wiley","issue":"4","license":[{"start":{"date-parts":[[2022,1,31]],"date-time":"2022-01-31T00:00:00Z","timestamp":1643587200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"funder":[{"DOI":"10.13039\/100000002","name":"National Institutes of Health","doi-asserted-by":"publisher","award":["P01CA125066"],"award-info":[{"award-number":["P01CA125066"]}],"id":[{"id":"10.13039\/100000002","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Archiv der Pharmazie"],"published-print":{"date-parts":[[2022,4]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Microbial strains isolated from extreme and understudied environments, such as caves, are still poorly investigated for the production of bioactive secondary metabolites. Investigation of the ethyl acetate extract from the growth medium produced by the soil\u2010derived fungus <jats:italic>Aspergillus<\/jats:italic> sp. SDC28, isolated from a Brazilian cave, yielded two anthraquinones: versicolorin C (<jats:bold>1<\/jats:bold>) and versiconol (<jats:bold>2<\/jats:bold>). The complete assignment of nuclear magnetic resonance and mass spectroscopic data of <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold> was performed for the first time. Moreover, the yet unreported absolute configuration of both compounds was unambiguously established by analysis of experimental and theoretical electronic circular dichroism data. Vibrational circular dichroism was also applied to confirm the absolute stereochemistry of <jats:bold>2<\/jats:bold>. Compounds <jats:bold>1<\/jats:bold> and <jats:bold>2<\/jats:bold> showed cytotoxic activity against human ovarian cancer cells (OVCAR3).<\/jats:p>","DOI":"10.1002\/ardp.202100441","type":"journal-article","created":{"date-parts":[[2022,1,31]],"date-time":"2022-01-31T12:27:03Z","timestamp":1643632023000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":10,"title":["Absolute configuration of cytotoxic anthraquinones from a Brazilian cave soil\u2010derived fungus, <i>Aspergillus<\/i> sp. SDC28"],"prefix":"10.1002","volume":"355","author":[{"given":"Juliana R.","family":"Gubiani","sequence":"first","affiliation":[{"name":"Instituto de Qu\u00edmica de S\u00e3o Carlos Universidade de S\u00e3o Paulo S\u00e3o Carlos Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Darlon I.","family":"Bernardi","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica de S\u00e3o Carlos Universidade de S\u00e3o Paulo S\u00e3o Carlos Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Caio C. P.","family":"De Paula","sequence":"additional","affiliation":[{"name":"Departamento de Ecologia e Biologia Evolutiva Universidade Federal de S\u00e3o Carlos S\u00e3o Carlos Brazil"},{"name":"Biology Centre CAS Institute of Hydrobiology \u010cesk\u00e9 Bud\u011bjovice Czech Republic"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mirna H. R.","family":"Seleghim","sequence":"additional","affiliation":[{"name":"Departamento de Ecologia e Biologia Evolutiva Universidade Federal de S\u00e3o Carlos S\u00e3o Carlos Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Antonio G.","family":"Ferreira","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Universidade Federal de S\u00e3o Carlos S\u00e3o Carlos Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrea N. L.","family":"Batista","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica Universidade Federal Fluminense Niter\u00f3i Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-0267-2631","authenticated-orcid":false,"suffix":"Jr.","given":"Jo\u00e3o M.","family":"Batista\u00a0","sequence":"additional","affiliation":[{"name":"Instituto de Ci\u00eancia e Tecnologia Universidade Federal de S\u00e3o Paulo S\u00e3o Jos\u00e9 dos Campos Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Lucianne F. P.","family":"Oliveira","sequence":"additional","affiliation":[{"name":"Departamento de Ci\u00eancias Exatas, Escola Superior de Agricultura Luiz de Queiroz Universidade de S\u00e3o Paulo Piracicaba Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Simone P.","family":"Lira","sequence":"additional","affiliation":[{"name":"Departamento de Ci\u00eancias Exatas, Escola Superior de Agricultura Luiz de Queiroz Universidade de S\u00e3o Paulo Piracicaba Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Joanna E.","family":"Burdette","sequence":"additional","affiliation":[{"name":"Pharmaceutical Sciences, College of Pharmacy University of Illinois Ashland Oregon USA"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0118-2523","authenticated-orcid":false,"given":"Roberto G. S.","family":"Berlinck","sequence":"additional","affiliation":[{"name":"Instituto de Qu\u00edmica de S\u00e3o Carlos Universidade de S\u00e3o Paulo S\u00e3o Carlos Brazil"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2022,1,31]]},"reference":[{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1590\/0001-3765201920180583"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.4311\/2016MB0100"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1080\/01490450152467750"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.5038\/1827-806X.42.3.10"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.5038\/1827-806X.38.1.8"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.3389\/fmicb.2018.01407"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.5038\/1827-806X.42.1.9"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.5038\/1827-806X.39.1.2"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.5038\/1827-806X.47.2.2148"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.5038\/1827-806X.46.3.2105"},{"key":"e_1_2_8_12_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bcab.2018.07.031"},{"key":"e_1_2_8_13_1","first-page":"1","volume":"63","author":"Costa Souza P. N.","year":"2020","journal-title":"Braz. Arch. Biol. Technol."},{"key":"e_1_2_8_14_1","volume-title":"New and Future Developments in Microbial Biotechnology and Bioengineering\u2014Aspergillus System Properties and Applications","author":"Gupta V. K.","year":"2016"},{"key":"e_1_2_8_15_1","doi-asserted-by":"publisher","DOI":"10.3390\/jof2020013"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jnatprod.1c00098"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.3390\/md17050283"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1246\/bcsj.48.2648"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1016\/0006-2952(71)90493-X"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.bioorg.2005.09.002"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1134\/S0026261717020114"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1039\/p19790000451"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.7164\/antibiotics.48.191"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1007\/s12272-010-0207-4"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.phytol.2018.06.009"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1039\/p19790000460"},{"issue":"10","key":"e_1_2_8_27_1","first-page":"2469","volume":"137","author":"Yabe K.","year":"1991","journal-title":"Microbiology"},{"key":"e_1_2_8_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/acschembio.9b00380"},{"key":"e_1_2_8_29_1","doi-asserted-by":"publisher","DOI":"10.1080\/00021369.1969.10859290"},{"key":"e_1_2_8_30_1","unstructured":"M. J.Frisch G. W.Trucks H. B.Schlegel G. E.Scuseria M. A.Robb J. R.Cheeseman G.Scalmani V.Barone B.Mennucci G. A.Petersson H.Nakatsuji M.Caricato X.Li H. P.Hratchian A. F.Izmaylov J.Bloino G.Zheng J. L.Sonnenberg M.Hada M.Ehara K.Toyota R.Fukuda J.Hasegawa M.Ishida T.Nakajima Y.Honda O.Kitao H.Nakai T.Vreven J. A.Montgomery J. E.Peralta F.Ogliaro M.Bearpark J. J.Heyd E.Brothers K. N.Kudin V. N.Staroverov R.Kobayashi J.Normand K.Raghavachari A.Rendell J. C.Burant S. S.Iyengar J.Tomasi M.Cossi N.Rega N. J.Millam M.Klene J. E.Knox J. B.Cross V.Bakken C.Adamo J.Jaramillo R.Gomperts R. E.Stratmann O.Yazyev A. J.Austin R.Cammi C.Pomelli J. W.Ochterski R. L.Martin K.Morokuma V. G.Zakrzewski G. A.Voth P.Salvador J. J.Dannenberg S.Dapprich A. D.Daniels \u00d6.Farkas J. B.Foresman J. V.Ortiz J.Cioslowski D. J.Fox Gaussian 09 Revision A.02 Gaussian Wallingford CT2009."}],"container-title":["Archiv der Pharmazie"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ardp.202100441","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/full-xml\/10.1002\/ardp.202100441","content-type":"application\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/ardp.202100441","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,8,25]],"date-time":"2023-08-25T10:35:28Z","timestamp":1692959728000},"score":1,"resource":{"primary":{"URL":"https:\/\/onlinelibrary.wiley.com\/doi\/10.1002\/ardp.202100441"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,1,31]]},"references-count":29,"journal-issue":{"issue":"4","published-print":{"date-parts":[[2022,4]]}},"alternative-id":["10.1002\/ardp.202100441"],"URL":"https:\/\/doi.org\/10.1002\/ardp.202100441","archive":["Portico"],"relation":{},"ISSN":["0365-6233","1521-4184"],"issn-type":[{"value":"0365-6233","type":"print"},{"value":"1521-4184","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,1,31]]},"assertion":[{"value":"2021-11-09","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-01-07","order":1,"name":"accepted","label":"Accepted","group":{"name":"publication_history","label":"Publication History"}},{"value":"2022-01-31","order":2,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"2100441"}}