title: Pleurospiroketals A-E, perhydrobenzannulated 5,5-spiroketal sesquiterpenes from the edible mushroom Pleurotus cornucopiae.
abstract: Five novel perhydrobenzannulated 5,5-spiroketal sesquiterpenes, namely, pleurospiroketals A-E (1-5), were isolated from the culture of the edible mushroom Pleurotus cornucopiae. Pleurospiroketals D (4) and E (5) were obtained as an isomeric mixture with a ratio of 5:4. Their structures were established by NMR, X-ray single-crystal diffraction, and CD data analysis. Pleurospiroketals A-E (1-5) are sesquiterpenoids with a unique benzannulated 5,5-spiroketal skeleton. Compounds 1-3 showed inhibitory activity against nitric oxide production in lipopolysaccharide-activated macrophages with IC(50) values of 6.8, 12.6, and 20.8 μM, respectively.
authors.affiliation: State Key Laboratory of Mycology, Institute of Microbiology, Chinese Academy of Sciences, No.9 Beiertiao, Zhongguancun, Haidian District, Beijing 100190, People's Republic of China.
authors.forename: Shao-juan
authors.initials: SJ
authors.lastname: Wang
authors.forename: Li
authors.initials: L
authors.lastname: Bao
authors.forename: Jun-jie
authors.initials: JJ
authors.lastname: Han
authors.forename: Quan-xin
authors.initials: QX
authors.lastname: Wang
authors.forename: Xiao-li
authors.initials: XL
authors.lastname: Yang
authors.forename: Hua-an
authors.initials: HA
authors.lastname: Wen
authors.forename: Liang-dong
authors.initials: LD
authors.lastname: Guo
authors.forename: Shao-jie
authors.initials: SJ
authors.lastname: Li
authors.forename: Feng
authors.initials: F
authors.lastname: Zhao
authors.forename: Hong-wei
authors.initials: HW
authors.lastname: Liu
mesh_terms: D000818:Animals; D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; 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; D020076:Pleurotus / Q000737:chemistry*; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013237:Stereoisomerism
chemical_list: D005663:Furans; D008070:Lipopolysaccharides; D012717:Sesquiterpenes; D013141:Spiro Compounds; C579262:pleurospiroketal A; C520774:spiroketal; D009569:Nitric Oxide