{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,15]],"date-time":"2026-05-15T02:56:30Z","timestamp":1778813790522,"version":"3.51.4"},"reference-count":31,"publisher":"MDPI AG","issue":"1","license":[{"start":{"date-parts":[[2022,1,14]],"date-time":"2022-01-14T00:00:00Z","timestamp":1642118400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["_"],"award-info":[{"award-number":["_"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100002347","name":"Federal Ministry of Education and Research","doi-asserted-by":"publisher","award":["_"],"award-info":[{"award-number":["_"]}],"id":[{"id":"10.13039\/501100002347","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100009139","name":"German Center for Infection Research","doi-asserted-by":"publisher","award":["_"],"award-info":[{"award-number":["_"]}],"id":[{"id":"10.13039\/100009139","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Marine myxobacteria present a virtually unexploited reservoir for the discovery of natural products with diverse biological functions and novel chemical scaffolds. We report here the isolation and structure elucidation of eight new deoxyenhygrolides (1\u20138) from the marine myxobacterium Plesiocystis pacifica DSM 14875T. The herein described deoxyenhygrolides C\u2013J (1\u20138) feature a butenolide core with an ethyl residue at C-3 of the \u03b3-lactone in contrast to the previously described derivatives, deoxyenhygrolides A and B, which feature an isobutyl residue at this position. The butenolide core is 2,4-substituted with a benzyl (1, 2 and 7), benzoyl (3 and 4) or benzyl alcohol (5, 6 and 8) moiety in the 2-position and a benzylidene (1\u20136) or benzylic hemiketal (7 and 8) in the 4-position. The description of these new deoxyenhygrolide derivatives, alongside genomic in silico investigation regarding putative biosynthetic genes, provides some new puzzle pieces on how this natural product class might be formed by marine myxobacteria.<\/jats:p>","DOI":"10.3390\/md20010072","type":"journal-article","created":{"date-parts":[[2022,1,16]],"date-time":"2022-01-16T20:45:21Z","timestamp":1642365921000},"page":"72","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["New Deoxyenhygrolides from Plesiocystis pacifica Provide Insights into Butenolide Core Biosynthesis"],"prefix":"10.3390","volume":"20","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-3420-9286","authenticated-orcid":false,"given":"Joachim J.","family":"Hug","sequence":"first","affiliation":[{"name":"Helmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbr\u00fccken, Germany"},{"name":"German Center for Infection Research (DZIF), Partner Site Hannover-Braunschweig, 38124 Braunschweig, Germany"},{"name":"Helmholtz International Labs, Department of Microbial Natural Products, Saarland University, Campus E8 1, 66123 Saarbr\u00fccken, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6274-4265","authenticated-orcid":false,"given":"Louise","family":"Kjaerulff","sequence":"additional","affiliation":[{"name":"Helmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbr\u00fccken, Germany"},{"name":"German Center for Infection Research (DZIF), Partner Site Hannover-Braunschweig, 38124 Braunschweig, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ronald","family":"Garcia","sequence":"additional","affiliation":[{"name":"Helmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbr\u00fccken, Germany"},{"name":"German Center for Infection Research (DZIF), Partner Site Hannover-Braunschweig, 38124 Braunschweig, Germany"},{"name":"Helmholtz International Labs, Department of Microbial Natural Products, Saarland University, Campus E8 1, 66123 Saarbr\u00fccken, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Rolf","family":"M\u00fcller","sequence":"additional","affiliation":[{"name":"Helmholtz-Institute for Pharmaceutical Research Saarland (HIPS), Helmholtz Centre for Infection Research (HZI), Saarland University, Campus E8 1, 66123 Saarbr\u00fccken, Germany"},{"name":"German Center for Infection Research (DZIF), Partner Site Hannover-Braunschweig, 38124 Braunschweig, Germany"},{"name":"Helmholtz International Labs, Department of Microbial Natural Products, Saarland University, Campus E8 1, 66123 Saarbr\u00fccken, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,1,14]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"770","DOI":"10.1021\/acs.jnatprod.9b01285","article-title":"Natural Products as Sources of New Drugs over the Nearly Four Decades from 01\/1981 to 09\/2019","volume":"83","author":"Newman","year":"2020","journal-title":"J. Nat. Prod."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"726","DOI":"10.1038\/s41570-021-00313-1","article-title":"Towards the sustainable discovery and development of new antibiotics","volume":"5","author":"Miethke","year":"2021","journal-title":"Nat. Rev. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"362","DOI":"10.1039\/D0NP00089B","article-title":"Marine natural products","volume":"38","author":"Carroll","year":"2021","journal-title":"Nat. Prod. Rep."},{"key":"ref_4","doi-asserted-by":"crossref","unstructured":"Jungblut, S., Liebich, V., and Bode-Dalby, M. (2020). Secondary Metabolites of Marine Microbes: From Natural Products Chemistry to Chemical Ecology. YOUMARES 9\u2014The Oceans: Our Research, Our Future, Proceedings of the 2018 Conference for YOUng MArine RESearcher, 11.09.2018\u201314.09.2018, Carl von Ossietzky University of Oldenburg, Oldenburg, Germany, Springer Open.","DOI":"10.1007\/978-3-030-20389-4"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1039\/D0OB01677B","article-title":"Recent highlights of biosynthetic studies on marine natural products","volume":"19","author":"Jautzus","year":"2021","journal-title":"Org. Biomol. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1039\/C6NP00106H","article-title":"Natural products from myxobacteria: Novel metabolites and bioactivities","volume":"34","author":"Herrmann","year":"2017","journal-title":"Nat. Prod. Rep."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Garcia, R., La Clair, J.J., and M\u00fcller, R. (2018). Future Directions of Marine Myxobacterial Natural Product Discovery Inferred from Metagenomics. Mar. Drugs, 16.","DOI":"10.3390\/md16090303"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"189","DOI":"10.1099\/ijs.0.02418-0","article-title":"Plesiocystis pacifica gen. nov., sp. nov., a marine myxobacterium that contains dihydrogenated menaquinone, isolated from the pacific coasts of Japan","volume":"53","author":"Iizuka","year":"2003","journal-title":"Int. J. Syst. Evol. Microbiol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"969","DOI":"10.3762\/bjoc.12.96","article-title":"Marine-derived myxobacteria of the suborder Nannocystineae: An underexplored source of structurally intriguing and biologically active metabolites","volume":"12","author":"Hufendiek","year":"2016","journal-title":"Beilstein J. Org. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"5571","DOI":"10.1128\/AEM.00224-08","article-title":"PCR detection of type I polyketide synthase genes in myxobacteria","volume":"74","author":"Komaki","year":"2008","journal-title":"Appl. Environ. Microbiol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"16600","DOI":"10.1038\/s41598-018-34954-y","article-title":"Analysis of the Genome and Metabolome of Marine Myxobacteria Reveals High Potential for Biosynthesis of Novel Specialized Metabolites","volume":"8","author":"Alanjary","year":"2018","journal-title":"Sci. Rep."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"385","DOI":"10.1038\/ja.2006.55","article-title":"Miuraenamides A and B, novel antimicrobial cyclic depsipeptides from a new slightly halophilic myxobacterium: Taxonomy, production, and biological properties","volume":"59","author":"Iizuka","year":"2006","journal-title":"J. Antibiot."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"126","DOI":"10.1002\/asia.200700233","article-title":"Miuraenamides: Antimicrobial cyclic depsipeptides isolated from a rare and slightly halophilic myxobacterium","volume":"3","author":"Ojika","year":"2008","journal-title":"Chem. Asian J."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"153","DOI":"10.7164\/antibiotics.54.153","article-title":"Haliangicin, a novel antifungal metabolite produced by a marine myxobacterium. 2. Isolation and structural elucidation","volume":"54","author":"Fudou","year":"2001","journal-title":"J. Antibiot."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"149","DOI":"10.7164\/antibiotics.54.149","article-title":"Haliangicin, a novel antifungal metabolite produced by a marine myxobacterium. 1. Fermentation and biological characteristics","volume":"54","author":"Fudou","year":"2001","journal-title":"J. Antibiot."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"1363","DOI":"10.1002\/cbic.201300268","article-title":"Salimyxins and enhygrolides: Antibiotic, sponge-related metabolites from the obligate marine myxobacterium Enhygromyxa salina","volume":"14","author":"Felder","year":"2013","journal-title":"ChemBioChem"},{"key":"ref_17","doi-asserted-by":"crossref","unstructured":"Tomura, T., Nagashima, S., Yamazaki, S., Iizuka, T., Fudou, R., and Ojika, M. (2017). An Unusual Diterpene-Enhygromic Acid and Deoxyenhygrolides from a Marine Myxobacterium, Enhygromyxa sp.. Mar. Drugs, 15.","DOI":"10.3390\/md15040109"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"803","DOI":"10.1038\/s41467-018-03184-1","article-title":"Correlating chemical diversity with taxonomic distance for discovery of natural products in myxobacteria","volume":"9","author":"Hoffmann","year":"2018","journal-title":"Nat. Commun."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2451","DOI":"10.1038\/nprot.2007.354","article-title":"Mosher ester analysis for the determination of absolute configuration of stereogenic (chiral) carbinol carbons","volume":"2","author":"Hoye","year":"2007","journal-title":"Nat. Protoc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"761","DOI":"10.1016\/0040-4039(93)89005-B","article-title":"Nostoclide I and II, extracellular metabolites from a symbiotic cyanobacterium, Nostoc sp., from the lichen Peltigera canina","volume":"34","author":"Yang","year":"1993","journal-title":"Tetrahedron Lett."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"4035","DOI":"10.1021\/jo00170a032","article-title":"Structure of the antibiotic cyanobacterin, a chlorine-containing .gamma.-lactone from the freshwater cyanobacterium Scytonema hofmanni","volume":"48","author":"Pignatello","year":"1983","journal-title":"J. Org. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"725","DOI":"10.1038\/ja.2014.55","article-title":"Angiolactone, a new Butyrolactone isolated from the terrestrial myxobacterium, Angiococcus sp.","volume":"67","author":"Raju","year":"2014","journal-title":"J. Antibiot."},{"key":"ref_23","doi-asserted-by":"crossref","unstructured":"Gagunashvili, A.N., and Andr\u00e9sson, \u00d3.S. (2018). Distinctive characters of Nostoc genomes in cyanolichens. BMC Genom., 19.","DOI":"10.1186\/s12864-018-4743-5"},{"key":"ref_24","doi-asserted-by":"crossref","unstructured":"D\u2019Agostino, P.M., Seel, C.J., Gulder, T., and Gulder, T. (2021). (Bio-)Synthesis of the Aquatic Phytotoxin Cyanobacterin\u2014A Paradigm for Furanolide Core Structure Assembly. ChemRxiv.","DOI":"10.26434\/chemrxiv.14625774"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"14648","DOI":"10.1021\/ja906752u","article-title":"An Enzymatic Cyclopentyl[b]indole Formation Involved in Scytonemin Biosynthesis","volume":"131","author":"Balskus","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"15260","DOI":"10.1021\/ja807192u","article-title":"Investigating the initial steps in the biosynthesis of cyanobacterial sunscreen scytonemin","volume":"130","author":"Balskus","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_27","unstructured":"Linington, R.G. (2021, December 22). npatlas\u2014The Natural Products Atlas. Available online: https:\/\/www.npatlas.org."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1824","DOI":"10.1021\/acscentsci.9b00806","article-title":"The natural products atlas: An open access knowledge base for microbial natural products discovery","volume":"5","author":"Jacob","year":"2019","journal-title":"ACS Cent. Sci."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"1647","DOI":"10.1093\/bioinformatics\/bts199","article-title":"Geneious Basic: An integrated and extendable desktop software platform for the organization and analysis of sequence data","volume":"28","author":"Kearse","year":"2012","journal-title":"Bioinformatics"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"D279","DOI":"10.1093\/nar\/gkv1344","article-title":"The Pfam protein families database: Towards a more sustainable future","volume":"44","author":"Finn","year":"2016","journal-title":"Nucleic Acids Res."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"845","DOI":"10.1038\/nprot.2015.053","article-title":"The Phyre2 web portal for protein modeling, prediction and analysis","volume":"10","author":"Kelley","year":"2015","journal-title":"Nat. Protoc."}],"container-title":["Marine Drugs"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1660-3397\/20\/1\/72\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,13]],"date-time":"2025-10-13T13:27:21Z","timestamp":1760362041000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1660-3397\/20\/1\/72"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,1,14]]},"references-count":31,"journal-issue":{"issue":"1","published-online":{"date-parts":[[2022,1]]}},"alternative-id":["md20010072"],"URL":"https:\/\/doi.org\/10.3390\/md20010072","relation":{},"ISSN":["1660-3397"],"issn-type":[{"value":"1660-3397","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,1,14]]}}}