Four New Cytotoxic Tetrahydrofuranoid Lignans fromSinopodophyllum emodi

Abstract

Four new tetrahydrofuranoid lignans, (-)-tanegool-7'-methyl ether ( 1), (+)-7'-methoxylariciresinol (2), sinolignan C (3), and epipinoresinol-4,4'-di- O- β- D-glucopyranoside (4), were isolated from the roots and rhizomes of SINOPODOPHYLLUM EMODI together with one known lignan (5). Their structures and stereochemistry were elucidated on the basis of spectroscopic and mass spectrometric evidence. The isolation of compounds 1- 5 represents the first report of tetrahydrofuran lignans from the genus SINOPODOPHYLLUM. The cytotoxic activities of all isolated compounds were evaluated against HeLa and KB cell lines, and compound 1 showed the most potent cytotoxicity with IC₅₀ values of 9.7 µM and 4.7 µM, respectively.

New Lignans and Iridoid Glycosides from Dipsacus asper Wall

“…Moreover, the downfield shift of C-7' (δ C : 88.9 ppm) and upfield shifts of H-9α (δ H : 3.19 ppm) and H-9β (δ H : 3.51 ppm) due to shielding by the phenyl ring at C-7 in 3 , which also supported that the phenyl ring at C-7 in 3 possessed the β-orientation, and H-7 and H-7' were threo -configuration [ 9 , 11 , 12 , 13 ]. In addition, the specific rotation of 3 was consistent with the report of vitexkarinol [ 14 ], but opposite to that of epi -pinoresionl-4, 4'-di- O -β- d -glucopyranoside [ 15 ]. On the basis of the above evidences, compound 3 was determined as (+)-(7 S , 8 S , 7' R , 8' S )-prinsepiol, and named dipsalignan B.…”

Evaluation of Antiulcer and Cytotoxic Potential of the Leaf, Flower, and Fruit Extracts of Calotropis procera and Isolation of a New Lignan Glycoside

“…The oxygenated quaternary carbons of the aromatic rings appeared at δ C 149.3, 147.7, 145.9, and 145.7 indicating the presence of one methoxy and three hydroxy groups at the rings. One of the methoxy groups was attached to the methine carbon of the lignan skeleton [ 26 ]. This was confirmed through the HMBC correlations of δ H 3.83 (7′-OCH 3 ) to δ C 85.9 (lignan C-7′), while the signal of methoxy group at δ H 3.84 (3-OCH 3 ) showed correlations with δ C 149.3 (C-3).…”

Bioactive Compounds from the Roots of Asiasarum heterotropoides

“…The 21 known compounds 2 – 22 were identified as (+)-7'-methoxylariciresinol ( 2 ) [18],(–)-tanegool-7'-methyl ether ( 3 ) [18], aristolactam I ( 4 ) [19], 7-methoxyaristololactam IV ( 5 ) [20,21], aristolochic acid IVa ( 6 ) [22], (7 α ,7' β ,8 α ,8' α )-3,4-methylenedioxy-3',4'-dihydroxy-7,9':7',9-diepoxy-lignane ( 7 ) [23], (–)-asarinin ( 8 ) [24], (+)-xanthoxylol ( 9 ) [25], (–)-epipinoresinol ( 10 ) [25],(–)-sesamin ( 11 ) [26], (–)-piperitol ( 12 ) [27,28], (1 R ,2 S ,5 R ,6 R )-5'- O -methylpluviatilol ( 13 ) [29], (2 S )-naringenin ( 14 ) [30], (2 S )-naringenin-5- O - β - d -glucopyranoside ( 15 ) [31], (2 S )-naringenin-7- O - β - d -glucopyranoside ( 16 ) [32], (+)-asarinol D ( 17 ) [33], (±)-asarinol A ( 18 ) [34], isovanillic acid ( 19 ) [35], 4-hydroxybenzoic acid ( 20 ) [36], trans - p -feruloyl- β - d -glucopyranoside ( 21 ) [37], and ( R )-5-(2,3-dihydroxypropyl)-1,3-benzodioxole ( 22 ) [38]. Thirteen of these compounds ( 2 , 3 , 7 , 10 , 12 – 17 , 19 , 21 , and 22 ) were isolated from A. heterotropoides for the first time in this study.…”