Sesquiterpenoids and lignans from the fruits of Illicium simonsii Maxim

Abstract Twenty-two known compounds were isolated from the 95% alcohol extract of the fruits of Illicium simonsii Maxim , including seven sesquiterpenoids ( 16 – 22 ) and fifteen lignans ( 1 – 15 ). In the present research, compounds 3 ((7 S ,8 R ,8′ S )-3,3′-dimethoxy-4,4′,9-trihydroxy-7,9′-epoxylignan-7′-one), 4 ((−)-(7′ S ,8 S ,8′ R )-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one), 5 ((+)-8-hydroxypinoresinol), 6 ((+)-8-hydroxymedioresinol), 8 ((2 R ,3 R )-2 β -(4″-hydroxy-3″-methoxybenzyl)-3 α -(4′-hydroxy-3′-methoxybenzyl)- γ -butyrolactone 2- O -( β -D-glucopyranoside), 12 ((+)-8-methoxyisolariciresinol), 13 ( α -conidendrin), 14 (boehmenan) and 15 (7 R ,8 R ,7′ E -7′,8′-didehydro-4,7,9,9′- tetrahydroxy-3-methoxy-8- O -4′-neolignan) were reported from the Illicium genus for the first time, and compounds 1 (simulanol), 7 ((+)-secoisolariciresinol monoglucoside), 10 ((+)-9- O - β -D-glucopyranosyl lyoniresinol), 11 ((+)-isolariciresinol), 18 (neoanisatin), 19 (veranisatin A), 20 (4,5-d 2 -8′-oxo-dihydrophaseic acid) and 22 (Oligandrumin A) were firstly isolated from the plant. Their structures were elucidated on the basis of NMR spectroscopic and mass spectrometric data. Moreover, the chemotaxonomic significance of the isolated compounds is discussed.