Cinerin C: a macrophyllin-type bicyclo[3.2.1]octane neolignan from Pleurothyrium cinereum (Lauraceae).

Ericsson D Coy-Barrera, Luis E Cuca-Suárez, Michael Sefkow, Uwe Schilde

Laboratorio de Bioorgánica, Departamento de Química, Facultad de Ciencias Básicas, Universidad Militar Nueva Granada, Colombia.

Acta crystallographica. Section C, Crystal structure communications 2012 Aug

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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.

Citation

Ericsson D Coy-Barrera, Luis E Cuca-Suárez, Michael Sefkow, Uwe Schilde. Cinerin C: a macrophyllin-type bicyclo[3.2.1]octane neolignan from Pleurothyrium cinereum (Lauraceae). Acta crystallographica. Section C, Crystal structure communications. 2012 Aug;68(Pt 8):o320-2