title: One-Step Semisynthesis of a Segetane Diterpenoid from a Jatrophane Precursor via a Diels-Alder Reaction.
abstract: A novel segetane diterpenoid (1) and four jatrophane diterpenoids (2-5) were isolated from an acetone extract of Euphorbia peplus. Due to quantity limitations, we prepared 1 via a Diels-Alder reaction, an approach motivated by this compound's biosynthetic pathway and successfully performed X-ray analysis of 1. Furthermore, in an in vitro activity test, 1 exhibited moderate anti-inflammatory activity, whereas both its precursor (2) and the relevant intermediate (2a, IC50 = 1.56 μM) exhibited significant anti-inflammatory activity.
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , 132 Lanhei Road, Kunming 650201, P. R. China.
authors.forename: Luo-Sheng
authors.initials: LS
authors.lastname: Wan
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , 132 Lanhei Road, Kunming 650201, P. R. China.
authors.forename: Li-Dong
authors.initials: LD
authors.lastname: Shao
authors.affiliation: Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States.
authors.forename: Liangbing
authors.initials: L
authors.lastname: Fu
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , 132 Lanhei Road, Kunming 650201, P. R. China.|University of Chinese Academy of Sciences , Beijing 100049, P. R. China.
authors.forename: Jun
authors.initials: J
authors.lastname: Xu
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , 132 Lanhei Road, Kunming 650201, P. R. China.|University of Chinese Academy of Sciences , Beijing 100049, P. R. China.
authors.forename: Guo-Lei
authors.initials: GL
authors.lastname: Zhu
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , 132 Lanhei Road, Kunming 650201, P. R. China.
authors.forename: Xing-Rong
authors.initials: XR
authors.lastname: Peng
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , 132 Lanhei Road, Kunming 650201, P. R. China.
authors.forename: Xiao-Nian
authors.initials: XN
authors.lastname: Li
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , 132 Lanhei Road, Kunming 650201, P. R. China.
authors.forename: Yan
authors.initials: Y
authors.lastname: Li
authors.affiliation: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences , 132 Lanhei Road, Kunming 650201, P. R. China.|University of Chinese Academy of Sciences , Beijing 100049, P. R. China.
authors.forename: Ming-Hua
authors.initials: MH
authors.lastname: Qiu
mesh_terms: D000818:Animals; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D028481:Euphorbia / Q000737:chemistry*; D008070:Lipopolysaccharides / Q000494:pharmacology; D008264:Macrophages / Q000187:drug effects; D051379:Mice; D008968:Molecular Conformation; D015394:Molecular Structure; D009569:Nitric Oxide / Q000096:biosynthesis; D019906:Nuclear Magnetic Resonance, Biomolecular
chemical_list: D004224:Diterpenes; D008070:Lipopolysaccharides; C530345:jatrophane; D009569:Nitric Oxide