title: Ivorenolide A, an unprecedented immunosuppressive macrolide from Khaya ivorensis: structural elucidation and bioinspired total synthesis.
abstract: Ivorenolide A (1), a novel 18-membered macrolide featuring conjugated acetylenic bonds and five chiral centers, was isolated from Khaya ivorensis. The structure of 1 was fully determined by spectroscopic analysis, single-crystal X-ray diffraction, and bioinspired total synthesis. Both compound 1 and its synthetic enantiomer 2 showed potent and selective immunosuppressive activity.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. China.
authors.forename: Bo
authors.initials: B
authors.lastname: Zhang
authors.forename: Yao
authors.initials: Y
authors.lastname: Wang
authors.forename: Sheng-Ping
authors.initials: SP
authors.lastname: Yang
authors.forename: Yu
authors.initials: Y
authors.lastname: Zhou
authors.forename: Wen-Bin
authors.initials: WB
authors.lastname: Wu
authors.forename: Wei
authors.initials: W
authors.lastname: Tang
authors.forename: Jian-Ping
authors.initials: JP
authors.lastname: Zuo
authors.forename: Ying
authors.initials: Y
authors.lastname: Li
authors.forename: Jian-Min
authors.initials: JM
authors.lastname: Yue
mesh_terms: D000818:Animals; D001402:B-Lymphocytes / Q000187:drug effects / Q000276:immunology; D018360:Crystallography, X-Ray; D007166:Immunosuppressive Agents / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D018942:Macrolides / Q000737:chemistry* / Q000302:isolation & purification / Q000494:pharmacology; D029582:Meliaceae / Q000737:chemistry*; D051379:Mice; D008958:Models, Molecular; D013237:Stereoisomerism; D013601:T-Lymphocytes / Q000187:drug effects / Q000276:immunology
chemical_list: D007166:Immunosuppressive Agents; D018942:Macrolides; C581291:ivorenolide A