Chemotaxonomic significance of lignans from Serissa japonica (Thunb.) Thunb

Sixteen known lignans were isolated from the 95% alcohol extract of the whole plant of Serissa japonica (Thunb.) Thunb., including nine furofurans (1-9), three tetrahydrofurans (10-12) and four arylnaphthalenes (13-16). In the present report, compounds (+)-epipinoresinol (1), (+)-1-hydroxy-6-epipinoresinol 4,4 ''-di-O-methyl ether (3), (-)-pinoresinol (4), (+)-8-hydroxypinoresinol (6), pseuderesinol (7), (+)-1-hydroxysyringaresinol (8), (-)-(7'S,8S,8'R)-4,4'-dihydroxy-3,3',5,5'-tetramethoxy-7',9-epoxylignan-9'-ol-7-one (10), wikstrone (11), 7'-(+)-oxomatairesinol (12), (+)-cycloolivil (13), (+)-isolariciresinol (14), 5-methoxy-(+)-isolariciresinol (15) and cyclolignans (16) were reported from the Serissa genus for the first time, and compounds (+)-lirioresinol A (2) and (-)-lirioresinol B (5) were firstly isolated from the plant. Their structures were elucidated on the basis of extensive spectroscopic and chemical analyses. Moreover, the chemotaxonomic significance of the isolated compounds is discussed.