{"doi":"10.1021/acs.jnatprod.3c00381","title":"Ravidomycin Analogs from <i>Streptomyces</i> sp. Exhibit Altered Antimicrobial and Cytotoxic Selectivity","abstract":"Six new ravidomycin analogs ( 1 – 4, 6, and 7 ) were isolated from Streptomyces sp. Am59 using UV- and LCMS-guided separation based on Global Natural Products Social (GNPS) molecular networking analysis. Furthermore, we isolated fucomycin V ( 9 ), which possesses the same chromophore as ravidomycin but features a d -fucopyranose instead of d -ravidosamine. This is the first report of 9 as a natural product. Four new analogs ( 10 – 13 ) of 9 were also isolated. The structures were elucidated by combined spectroscopic and computational methods. We also found an inconsistency with the published [α] D 25 of deacetylravidomycin, which is reported to have a (−) sign. Instead, we observed a (+) specific rotation for the reported absolute configuration of deacetylravidomycin (containing d -ravidosamine). We confirmed the positive sign by reisolating deacetylravidomycin from S. ravidus and by deacetylating ravidomycin. Finally, antibacterial, antifungal, and cytotoxicity activities were determined for the compounds. Compared to deacetylravidomycin, the compounds 4 – 6, 9, 11, and 12 exhibited greater antibacterial selectivity.","journal":"Journal of Natural Products","year":2023,"id":355759,"datarank":0.0,"base_score":0.0,"endowment":0.0,"self_citation_contribution":0.0,"citation_network_contribution":0.0,"self_endowment_contribution":0.0,"citer_contribution":0.0,"corpus_percentile":null,"corpus_rank":null,"citation_count":5,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.949,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2023-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":1104119,"name":"Sarah Maier","orcid":"0000-0002-3817-1476","position":1,"is_corresponding":false},{"id":1104120,"name":"Chengqian Zhang","orcid":"0000-0001-7829-0587","position":2,"is_corresponding":false},{"id":676354,"name":"Shelley A.H. Dixon","orcid":null,"position":3,"is_corresponding":false},{"id":4131,"name":"Douglas B. Rusch","orcid":"0000-0002-1066-2687","position":4,"is_corresponding":false},{"id":373811,"name":"Mônica Tallarico Pupo","orcid":"0000-0003-2705-0123","position":5,"is_corresponding":false},{"id":391152,"name":"Steven P. Angus","orcid":"0000-0002-7655-657X","position":6,"is_corresponding":false},{"id":832115,"name":"Joseph P. Gerdt","orcid":"0000-0002-0375-4110","position":7,"is_corresponding":false},{"id":1104118,"name":"Kyoung-Jin Park","orcid":"0000-0001-9373-1440","position":0,"is_corresponding":true}],"reference_count":49,"raw_metadata":null,"created_at":"2026-07-19T01:13:21.145955Z","pmid":"37531219","pmcid":null,"fwci":null,"citation_percentile":null,"influential_citations":0,"oa_status":null,"license":null,"views":0,"total_file_size_bytes":0,"version_count":0,"fair_f":null,"fair_a":null,"fair_i":null,"fair_r":null,"fair_zscore":null,"fair_rationale":null,"fair_model":null,"fair_agent_version":null,"fair_fulltext_source":null,"fair_has_llm":null,"fair_computed_at":null,"clinical_trials":[],"software_tools":[],"db_accessions":[],"linked_datasets":[],"topics":[]}