title: Erythrolic acids A-E, meroterpenoids from a marine-derived Erythrobacter sp.
abstract: Erythrolic acids A-E (1-5) are five unusual meroterpenoids isolated from the bacterium Erythrobacter sp. derived from a marine sediment sample collected in Galveston, TX. The structures were elucidated by means of detailed spectroscopic analysis and chemical derivatization. The erythrolic acids contain a 4-hydroxybenzoic acid appended with a modified terpene side chain. The side-chain modifications include oxidation of a terminal methyl substituent and in the case of 1-4 addition of a two-carbon unit to give terpene side chains of unusual length: C22 for 1 and 2, C17 for 3, and C12 for 4. The relative and absolute configurations of the meroterpenoids were determined by coupling constant, NOE, and Mosher's analysis. In vitro cytotoxicity toward a number of nonsmall cell lung cancer (NSCLC) cell lines revealed only modest activity for erythrolic acid D (4) (2.5 μM against HCC44). The discovery of these unusual diterpenes, along with the previously reported erythrazoles, demonstrates the natural product potential of a previously unstudied group of bacteria for drug discovery. The unusual nature of the terpene side chain, we believe, involves an oxidation of a terminal methyl group to a carboxylic acid and subsequent Claisen condensation with acetyl-CoA.
authors.affiliation: Department of Biochemistry, Division of Chemistry, University of Texas Southwestern Medical Center, 5323 Harry Hines Boulevard, Dallas, Texas 75390-9038, USA.
authors.forename: Youcai
authors.initials: Y
authors.lastname: Hu
authors.forename: Aaron G
authors.initials: AG
authors.lastname: Legako
authors.forename: Ana Paula D M
authors.initials: AP
authors.lastname: Espindola
authors.forename: John B
authors.initials: JB
authors.lastname: MacMillan
mesh_terms: D002289:Carcinoma, Non-Small-Cell Lung / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D015394:Molecular Structure; D010226:Parabens / Q000737:chemistry*; D042301:Sphingomonadaceae / Q000737:chemistry*; D013729:Terpenes / Q000737:chemistry*
chemical_list: D010226:Parabens; D013729:Terpenes; C038193:4-hydroxybenzoic acid