title: Relative and absolute configuration of vatiparol (1 mg): a novel anti-inflammatory polyphenol.
abstract: Bioactive natural products offer multiple opportunities for the discovery of novel chemical entities with potential pharmaceutical, nutraceutical and agrochemical applications. Many new organic compounds with novel scaffolds are isolated in small quantities and established methods often fail to determine the structure and bioactivity of such novel natural products. To meet this challenge, we present here a new methodology combining RDC (residual dipolar coupling)-based NMR spectroscopy in microtubes, with a motif-inspired biological assessment strategy. Using only one milligram (ca. 1.5 μmol) of sample, the new protocol established the bioactivity as well as the relative and absolute configuration of vatiparol obtained from Vatica parvifolia. Vatiparol is unique in its unprecedented carbon skeleton and selective inhibitory effect on the expression of monocyte chemo-attractant protein-1 (MCP-1, also known as CCL2). The plausible biosynthetic pathway of vatiparol is briefly discussed. The approach introduced here promises to be widely applicable to the determination of the structure and bioactivity of structurally unknown organic samples available in very limited amounts.
authors.affiliation: Institute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, School of Lifesciences, Nanjing University, Nanjing 210093, China.
authors.forename: Hui Ming
authors.initials: HM
authors.lastname: Ge
authors.forename: Han
authors.initials: H
authors.lastname: Sun
authors.forename: Nan
authors.initials: N
authors.lastname: Jiang
authors.forename: Yan Hua
authors.initials: YH
authors.lastname: Qin
authors.forename: Huan
authors.initials: H
authors.lastname: Dou
authors.forename: Tong
authors.initials: T
authors.lastname: Yan
authors.forename: Ya Yi
authors.initials: YY
authors.lastname: Hou
authors.forename: Christian
authors.initials: C
authors.lastname: Griesinger
authors.forename: Ren Xiang
authors.initials: RX
authors.lastname: Tan
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000494:pharmacology*; D001688:Biological Products / Q000737:chemistry* / Q000494:pharmacology*; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy / Q000379:methods; D008956:Models, Chemical; D059808:Polyphenols / Q000737:chemistry* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D000893:Anti-Inflammatory Agents; D001688:Biological Products; D006576:Heterocyclic Compounds, 4 or More Rings; D059808:Polyphenols; C573200:vatiparol