title: Isolation, stereochemical study, and cytotoxic activity of isobenzofuran derivatives from a marine Streptomyces sp.
abstract: A new 1,3-dihydroisobenzofuran derivative (), together with its epimer (), was isolated from marine Streptomyces sp. W007. The structure of the two compounds was established by extensive spectroscopic analysis and comparison with reported data. The absolute configurations of and were determined by a combination of experimental and computational means, including J-coupling analysis and nuclear Overhauser effect spectroscopy (NOESY) spectra, nuclear magnetic resonance (NMR) calculations, electronic circular dichroism (ECD), and optical rotation (OR) calculations. Compound had no cytotoxicity against human lung adenocarcinoma cell line A549, while compound exhibited weak activity, suggesting that the biological activity depends on the configuration of a single chirality center.
authors.affiliation: School of Pharmaceutical Sciences, Binzhou Medical University, Yantai, China.
authors.forename: Shu-Min
authors.initials: SM
authors.lastname: Zhang
authors.forename: Hong-Yu
authors.initials: HY
authors.lastname: Zhang
authors.forename: Sheng-Xiang
authors.initials: SX
authors.lastname: Yang
authors.forename: Cheng-Lei
authors.initials: CL
authors.lastname: Qu
authors.forename: Ze-Ping
authors.initials: ZP
authors.lastname: Xie
authors.forename: Gennaro
authors.initials: G
authors.lastname: Pescitelli
mesh_terms: D059001:Aquatic Organisms / Q000737:chemistry*; D001572:Benzofurans / Q000737:chemistry* / Q000302:isolation & purification / Q000633:toxicity*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects*; D002942:Circular Dichroism; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011789:Quantum Theory; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry*
chemical_list: D001572:Benzofurans
keywords: TDDFT calculations; absolute structure elucidation; conformational analysis; marine actinomycete