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

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Abstract:

The structure of naturally‐occurring cinerin C [systematic name: (7S,8R,3′R,4′S,5′R)‐Δ8′‐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 strucure has now been established by single‐crystal X‐ray analysis, as the monohydrate, C22H26O7·H2O. 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′‐OCH3 groups along the c axis.

Document Type: Research Article

DOI: https://doi.org/10.1107/S0108270112030946

Publication date: 2012-08-15

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