title: Synergistic Contribution of Tiglate and Cinnamate to Cytotoxicity of Ipomoeassin F.
abstract: An efficient synthetic route for ipomoeassin F and its tiglate-modified analogues was developed. The route features late-stage conformation-controlled highly regioselective esterification of the glucose diol in the disaccharide core. The results from the NCI-60 cell line screens of ipomoeassin F were reported for the first time. Moreover, two new C-3-cinnamoyl-Glcp analogues (2 and 3) were prepared. Their in-house cytotoxicity data convey an important message that both identity and positioning of the two α,β-unsaturated esters are crucial. They are not interchangeable.
authors.affiliation: Department of Chemistry and Biochemistry, J. William Fulbright College of Arts & Science, University of Arkansas , Fayetteville, Arkansas 72701, United States.
authors.forename: Guanghui
authors.initials: G
authors.lastname: Zong
authors.affiliation: Department of Chemistry and Biochemistry, J. William Fulbright College of Arts & Science, University of Arkansas , Fayetteville, Arkansas 72701, United States.
authors.forename: Lucas
authors.initials: L
authors.lastname: Whisenhunt
authors.affiliation: Department of Chemistry and Biochemistry, J. William Fulbright College of Arts & Science, University of Arkansas , Fayetteville, Arkansas 72701, United States.
authors.forename: Zhijian
authors.initials: Z
authors.lastname: Hu
authors.affiliation: Department of Chemistry and Biochemistry, J. William Fulbright College of Arts & Science, University of Arkansas , Fayetteville, Arkansas 72701, United States.
authors.forename: Wei Q
authors.identifier: 0000-0001-5453-1753
authors.initials: WQ
authors.lastname: Shi
mesh_terms: D045744:Cell Line, Tumor; D002934:Cinnamates / Q000737:chemistry*; D003437:Crotonates / Q000737:chemistry*; D004354:Drug Screening Assays, Antitumor; D004357:Drug Synergism; D006001:Glycoconjugates / Q000494:pharmacology*; D045782:Hemiterpenes; D006801:Humans; D013057:Spectrum Analysis / Q000379:methods
chemical_list: D002934:Cinnamates; D003437:Crotonates; D006001:Glycoconjugates; D045782:Hemiterpenes; C523857:ipomoeassin F; C029010:cinnamic acid; C009489:tiglic acid