title: Cinerin C: a macrophyllin-type bicyclo[3.2.1]octane neolignan from Pleurothyrium cinereum (Lauraceae).
abstract: The structure of naturally-occurring cinerin C [systematic name: (7S,8R,3'R,4'S,5'R)-Δ(8')-4'-hydroxy-5,5',3'-trimethoxy-3,4-methylenedioxy-2',3',4',5'-tetrahydro-2'-oxo-7.3',8.5'-neolignan], isolated from the ethanol extract of leaves of Pleurothyrium cinereum (Lauraceae), has previously been established by NMR and HRMS spectroscopy, and its absolute configuration established by circular dichroism measurements. For the first time, its crystal structure has now been established by single-crystal X-ray analysis, as the monohydrate, C(22)H(26)O(7)·H(2)O. The bicyclooctane moiety comprises fused cyclopentane and cyclohexenone rings which are almost coplanar. An intermolecular O-H···O hydrogen bond links the 4'-OH and 5'-OCH(3) groups along the c axis.
authors.affiliation: Laboratorio de Bioorgánica, Departamento de Química, Facultad de Ciencias Básicas, Universidad Militar Nueva Granada, Colombia.
authors.forename: Ericsson D
authors.initials: ED
authors.lastname: Coy-Barrera
authors.forename: Luis E
authors.initials: LE
authors.lastname: Cuca-Suárez
authors.forename: Michael
authors.initials: M
authors.lastname: Sefkow
authors.forename: Uwe
authors.initials: U
authors.lastname: Schilde
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry* / Q000302:isolation & purification; D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D019770:Lauraceae / Q000737:chemistry*; D017705:Lignans / Q000737:chemistry* / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D018515:Plant Leaves / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001643:Bridged Bicyclo Compounds; D017705:Lignans; C550761:cinerin C