{"doi":"10.1016/j.jlr.2024.100632","title":"Novel odd-chain cyclopropane fatty acids: detection in a mammalian lipidome and uptake by hepatosplanchnic tissues","abstract":"Microbe-produced molecules (xenometabolites) found in foods or produced by gut microbiota are increasingly implicated in microbe-microbe and microbe-host communication. Xenolipids, in particular, are a class of metabolites for which the full catalog remains to be elaborated in mammalian systems. We and others have observed that cis-3,4-methylene-heptanoylcarnitine is a lipid derivative that is one of the most abundant medium-chain acylcarnitines in human blood, hypothesized to be a product of incomplete β-oxidation of one or more \"odd-chain\" long-chain cyclopropane fatty acids (CpFAs). We deduced two possible candidates, cis-11,12-methylene-pentadecanoic acid (cis-11,12-MPD) and cis-13,14-methylene-heptadecanoic acid (cis-13,14-MHD). Authentic standards were synthesized: cis-11-pentadecenoic acid and cis-13-heptadecenoic acid were generated (using Jones reagent) from cis-11-pentadecene-1-ol and cis-13-heptadecene-1-ol, respectively, and these were converted to CpFAs via a reaction involving diiodomethane. Using these standards in mass spectrometry analyses, we determined the presence/absence of cis-11,12-MPD and cis-13,14-MHD in archived piglet biospecimens. Both CpFAs were detected in rectal contents of sow and soy-fed piglets. Archived mass spectra were analyzed post hoc from a second independent study that used tissue-specific catheterization to monitor net metabolite flux in growing pigs. This confirmed the presence of both CpFAs in plasma and revealed a significant net uptake of the odd-chain CpFAs across the splanchnic tissue bed and liver. The results confirm that the novel xenolipids cis-11,12-MPD and cis-13,14-MHD can be components of the mammalian lipidome and are viable candidate precursors of cis-3,4-methylene-heptanoylcarnitine produced from partial β-oxidation in liver or other tissues.","journal":"Journal of Lipid Research","year":2024,"id":458238,"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":0.9496,"is_data_producer":false,"deposit_databanks":null,"is_oa":true,"file_count":0,"downloads":0,"has_version_chain":false,"published_date":"2024-01-01","fair_score":null,"fair_percentile":null,"algorithm_id":"datarank_citation_only_1hop_v6","ranking_scope":"data_only","authors":[{"id":276177,"name":"Kelly E. Mercer","orcid":null,"position":1,"is_corresponding":false},{"id":488292,"name":"Renny S. Lan","orcid":"0000-0001-8346-043X","position":2,"is_corresponding":false},{"id":273747,"name":"Laxmi Yeruva","orcid":"0000-0003-4289-9109","position":3,"is_corresponding":false},{"id":482673,"name":"Gabriëlla A. M. Ten Have","orcid":"0000-0003-2617-1193","position":4,"is_corresponding":false},{"id":470291,"name":"Nicolaas E.P. Deutz","orcid":"0000-0001-5845-6447","position":5,"is_corresponding":false},{"id":273738,"name":"Brian D. Piccolo","orcid":"0000-0002-1789-4587","position":6,"is_corresponding":false},{"id":1284114,"name":"Jean Debédat","orcid":"0000-0002-8377-5965","position":7,"is_corresponding":false},{"id":273742,"name":"Lindsay Pack","orcid":"0009-0005-1277-602X","position":8,"is_corresponding":false},{"id":273743,"name":"Sean H. Adams","orcid":"0000-0002-9515-2319","position":9,"is_corresponding":false},{"id":792009,"name":"Hany F. Sobhi","orcid":"0000-0002-7389-4936","position":0,"is_corresponding":true}],"reference_count":62,"raw_metadata":null,"created_at":"2026-07-19T02:03:46.117860Z","pmid":"39182606","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":[]}