{"doi":"10.1021/acs.jnatprod.2c01048","title":"Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus <i>Sarocladium</i> sp.","abstract":"High Resolution Image Download MS PowerPoint Slide Macrocyclic alkaloids with a cyclopenta[b]fluorene ring system are a relatively young structural class of fungal metabolites, with the first members reported in 2013. Bioassay-guided fractionation of a Sarocladium sp. (fungal strain MSX6737) led to a series of both known and new members of this structural class ( 1 – 5 ), including the known embellicine A ( 1 ), three new embellicine analogues ( 2, 4, and 5 ), and a semisynthetic acetylated analogue ( 3 ). The structures were identified by examining both high-resolution electrospray ionization mass spectrometry data and one-dimensional and two-dimensional NMR spectra. The relative configurations of these molecules were established via 1 H– 1 H coupling constants and nuclear Overhauser effect spectroscopy, while comparisons of the experimental electronic circular dichroism (ECD) spectra with the time-dependent density functional theory ECD calculations were utilized to assign their absolute configurations, which were in good agreement with the literature. These alkaloids ( 1 – 5 ) showed cytotoxic activity against a human breast cancer cell line (MDA-MB-231) that ranged from 0.4 to 4.8 μM. Compounds 1 and 5 were also cytotoxic against human ovarian (OVCAR3) and melanoma (MDA-MB-435) cancer cell lines.","journal":"Journal of Natural Products","year":2023,"id":349214,"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":10,"citer_count":0,"citers_with_citation_signal":0,"citers_with_endowment":0,"datacite_reuse_total":0,"is_dataset":false,"is_dataset_confidence":0.9455,"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":267271,"name":"Laura Flores‐Bocanegra","orcid":"0000-0002-1393-7834","position":1,"is_corresponding":false},{"id":267273,"name":"Huzefa A. Raja","orcid":"0000-0002-0824-9463","position":2,"is_corresponding":false},{"id":337779,"name":"Joanna E. Burdette","orcid":"0000-0002-7271-6847","position":3,"is_corresponding":false},{"id":394944,"name":"Cedric J. Pearce","orcid":"0000-0002-0212-1127","position":4,"is_corresponding":false},{"id":267276,"name":"Nicholas H. Oberlies","orcid":"0000-0002-0354-8464","position":5,"is_corresponding":false},{"id":748487,"name":"Zeinab Y. Al Subeh","orcid":"0000-0001-9051-4969","position":0,"is_corresponding":true}],"reference_count":57,"raw_metadata":null,"created_at":"2026-07-19T01:12:14.919810Z","pmid":"36884371","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":[]}