title: Rearranged prenylated C6-C3 compounds and a highly oxygenated seco-prezizaane-type sesquiterpene from the stem bark of Illicium oligandrum.
abstract: Three new rearranged prenylated C(6)-C(3) compounds, named illioliganones A, B, and C (1-3), and a new highly oxygenated seco-prezizaane-type sesquiterpene, oligandriortholactone (7), together with three known prenylated C(6)-C(3) compounds (4-6) and a known sesquiterpene lactone (8), have been isolated from the stem bark of Illicium oligandrum. The structures of 1-3 and 7 were elucidated by spectroscopic methods including 1D and 2D NMR, HRMS, and CD experiments. The absolute configuration of the 11,12-diol moiety in 2 and 3 was determined on the basis of observing the induced circular dichroism after addition of Mo(2)(OAc)(4) in DMSO solution. The anti-inflammatory and cytotoxic activities of 1-8 were evaluated.
authors.affiliation: Key Laboratory of Bioactive Substance and Resources Utilization of Chinese Herbal Medicine, Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union Medical College, Beijing, People's Republic of China.
authors.forename: Wen-Zhao
authors.initials: WZ
authors.lastname: Tang
authors.forename: Shuang-Gang
authors.initials: SG
authors.lastname: Ma
authors.forename: Shi-Shan
authors.initials: SS
authors.lastname: Yu
authors.forename: Jing
authors.initials: J
authors.lastname: Qu
authors.forename: Yun-Bao
authors.initials: YB
authors.lastname: Liu
authors.forename: Jing
authors.initials: J
authors.lastname: Liu
mesh_terms: D000818:Animals; D000893:Anti-Inflammatory Agents / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D052117:Benzodioxoles; D004365:Drugs, Chinese Herbal / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology; D005966:Glucuronidase / Q000187:drug effects; D029523:Illicium / Q000737:chemistry*; D007783:Lactones / Q000737:chemistry; D015394:Molecular Structure; D009504:Neutrophils / Q000187:drug effects / Q000201:enzymology; D019906:Nuclear Magnetic Resonance, Biomolecular; D024301:Plant Bark / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D010972:Platelet Activating Factor / Q000494:pharmacology; D051381:Rats; D012717:Sesquiterpenes / Q000737:chemistry* / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: D000893:Anti-Inflammatory Agents; D052117:Benzodioxoles; D004365:Drugs, Chinese Herbal; D007783:Lactones; D010972:Platelet Activating Factor; D012717:Sesquiterpenes; C542042:illioliganone A; C542043:illioliganone B; C542044:illioliganone C; C542045:oligandriortholactone; D005966:Glucuronidase