{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,22]],"date-time":"2026-10-22T09:26:23Z","timestamp":1792661183640,"version":"4.5.0"},"reference-count":22,"publisher":"American Chemical Society (ACS)","issue":"15","license":[{"start":{"date-parts":[[2016,7,25]],"date-time":"2016-07-25T00:00:00Z","timestamp":1469404800000},"content-version":"vor","delay-in-days":10,"URL":"https:\/\/pubs.acs.org\/page\/policy\/authorchoice_termsofuse.html"}],"funder":[{"DOI":"10.13039\/501100000923","name":"Australian Research Council","doi-asserted-by":"publisher","award":["DP120100183"],"award-info":[{"award-number":["DP120100183"]}],"id":[{"id":"10.13039\/501100000923","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001794","name":"University of Queensland","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100001794","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100014711","name":"Institute for Molecular Bioscience, University of Queensland","doi-asserted-by":"crossref","id":[{"id":"10.13039\/501100014711","id-type":"DOI","asserted-by":"crossref"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2016,8,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>The commercial antibiotics tetracycline (3), minocycline (4), chlortetracycline (5), oxytetracycline (6), and doxycycline (7) were biotransformed by a marine-derived fungus Paecilomyces sp. to yield seco-cyclines A\u2013H (9\u201314, 18 and 19) and hemi-cyclines A\u2013E (20\u201324). Structures were assigned by detailed spectroscopic analysis, and in the case of 10 X-ray crystallography. Parallel mechanisms account for substrate-product specificity, where 3\u20135 yield seco-cyclines and 6 and 7 yield hemi-cyclines. The susceptibility of 3\u20137 to fungal biotransformation is indicative of an unexpected potential for tetracycline \u201cdegradation\u201d (i.e., antibiotic resistance) in fungal genomes. Significantly, the fungal-derived tetracycline-like viridicatumtoxins are resistant to fungal biotransformation, providing chemical insights that could inform the development of new tetracycline antibiotics resistant to enzymatic degradation.<\/jats:p>","DOI":"10.1021\/acs.joc.6b01272","type":"journal-article","created":{"date-parts":[[2016,7,15]],"date-time":"2016-07-15T16:29:14Z","timestamp":1468600154000},"page":"6186-6194","source":"Crossref","is-referenced-by-count":41,"title":["Fungal Biotransformation\nof Tetracycline Antibiotics"],"prefix":"10.1021","volume":"81","author":[{"given":"Zhuo","family":"Shang","sequence":"first","affiliation":[{"name":"The University of Queensland , , , ,","place":["St. Lucia, QLD, Australia, 4072"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Angela A.","family":"Salim","sequence":"additional","affiliation":[{"name":"The University of Queensland , , , ,","place":["St. Lucia, QLD, Australia, 4072"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zeinab","family":"Khalil","sequence":"additional","affiliation":[{"name":"The University of Queensland , , , ,","place":["St. Lucia, QLD, Australia, 4072"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Paul V.","family":"Bernhardt","sequence":"additional","affiliation":[{"name":"The University of Queensland , , , ,","place":["St. Lucia, QLD, Australia, 4072"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Robert J.","family":"Capon","sequence":"additional","affiliation":[{"name":"The University of Queensland , , , ,","place":["St. Lucia, QLD, Australia, 4072"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2016,7,15]]},"reference":[{"key":"2026090314120979600_cit1","doi-asserted-by":"publisher","first-page":"12501","DOI":"10.1021\/acs.joc.5b02367","volume":"80","author":"Shang","year":"2015","journal-title":"J. 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