Lignan

Octane

Stereochemistry

Organic chemistry

Chemistry

Planta Medica

Six new lignans, 1–6, along with six known compounds were obtained from the flower buds of Magnolia liliflora Desr. The new lignans were elucidated as (1S*,2R*,5S*,6S*)-2-(3,5-dimethoxyphenyl)-6-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (1), (1R*,2R*,5R*,6S*)-2-(3,5-dimethoxyphenyl)-6-(3,4-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (2), (1R*, 2R*,5R*,6S*)-2,6-bis (3,5-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (3), (1R*,2S*,5R*,6R*)-2-(3,4-methylenedioxyphenyl)-6-(3,5-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane (4), (7′S*,8R*,8′R*)-3,5′-dimethoxy-3′,4,9′-trihydroxy-7′, 9-epoxy-8,8′-lignan (5), and (7′R*,8′S*)-3,3′,4,5′-tetramethoxy-7-en-7′,9-epoxy-8,8′-lignan (6), by the analysis of 1D and 2D-NMR as well as HRESIMS data. The capacity of compound 1 to protect against damages to the DNA of rat lymphocyte cells induced by UV irradiation was assessed by the comet assay. It showed stronger antigenotoxicity than ascorbic acid from 6 × 10−3 mmol · L−1 to 6 × 10−6 mmol · L−1.

Lignans from the Flower Buds ofMagnolia lilifloraDesr.