부산대학교 도서관

As a part of our continuing search for bioactive constituents from Korean medicinal plants, I investigated methanol extracts of the trunk of Abies holophylla and the twigs of Chaenomeles sinensis for cytotoxic constituents, since the above two plants showed considerable cytotoxicity against tested four human cancer cells in screening procedures. Through subsequent bioactivity-guided fractionation and isolation of the methanolic extracts of the two plants, 14 diterpenoids and 16 lignan derivatives from the trunk of A. holophylla, and 9 oxylipins, 11 lignan glycosides, and 5 biphenyl compounds from the twigs of C. sinensis were isolated. The structures of compounds from A. holophylla were identified as holophyllin A, B, and D – G (A-1 – A-6), 9,13β-epidioxy-8(14)-abieten-18-oic acid (A-7), 7-oxo-13β-hydroxyabiet-8(14)-en-18-oic acid (A-8), 7-oxo-13β-methoxyabiet-8(14)-en-18-oic acid (A-9), levopimaric acid endo-peroxide (A-10), 7α-hydroxydehydroabietic acid (A-11), (–)-8,11,13-abietatrien-7α-ol (A-12), 7α,18-dihydroxydehydroabietanol (A-13), abiesadine F (A-14), (7R,8S)-7,8-dihydro-3′-hydroxy-7-(4-hydroxy-3-methoxyphenyl)-8-hydroxymethyl-1′-benzofuranpropanol 4-O-β-D-glucopyranoside (A-22), 7R,8S-dihydrodehydrodiconiferyl alcohol 4-O-β-D-glucopyranoside (A-23), icariside E4 (A-24), juniperigiside (A-25), (–)-secoisolariciresinol (A-26), (2R,3R)-2β-(4′′-hydroxy-3′′-methoxybenzyl)-3α-(4′-hydroxy-3′-methoxybenzyl)-γ-butyrolactone 2-O-(β-D-glucopyranoside) (A-27), tanegool (A-28), lariciresinol 4-O-β-D-glucoside (A-29), and lariciresinol 4′-O-β-D-glucoside (A-30), using spectroscopic data including 1D and 2D NMR, MS, UV and IR, ECD calculation, and chemical reation. Structures of compounds from C. sienesis were determined to be chaenomic acid A – E (B-1 – B-5), pinellic acid (B-6), methyl (9S,10E,12S,13S)-9,12,13-trihydroxy-10-octadecenoate (B-7), corchorifatty acid F (B-8), methyl 9,12,13-trihydroxyoctadeca-10E,15Z-dienoate (B-9), chaenomiside A – F (B-10 – B-15), (7R,8S)-dihydrodehydrodiconiferyl alcohol 9-O-β-D-glucopyranoside (B-16), (7S,8R)-dihydrodehydrodiconiferyl alcohol 9-O-α-L-rhamnoside (B-17), (+)-9′-O-(β-D-glucopyranosyl)lyoniresinol (B-18), (–)-9′-O-(α-L-rhamnopyranosyl)lyoniresinol (B-19), aviculin (B-20), ε-cotonefuran (B-21), 2′-hydroxyaucuparin (B-22), 2′-methoxyaucuparin (B-23), aucuparin (B-24), and berbekorin (B-25), by NMR, MS, UV, IR, CD data analysis and hydrolysis. Among these isolates, compounds A-1 – A-6, A-15 – A-20, B-1 – B-5, and B-10 – B-15 were newly isolated from the nature.Cytotoxic activities of the isolated compounds (A-1 – A-30) from A. holophylla against A549, SK-OV-3, SK-MEL-2, and HCT15 human cancer cell lines were evaluated using the SRB assay in vitro. Compound A-12 exhibited moderate cytotoxic activity against all cells, A549, SK-OV-3, SK-MEL-2, and HCT116, (IC50 13.24, 16.28, 11.75, and 9.87 μM, respectively), and A-3, A-5 – A-11, A-13 and A-14 showed moderate cytotoxicity against several tested cell lines (IC50 14.74 – 29.58 μM). The other compounds were inactive (IC50 > 30 μM). Cytotoxic activities of the isolated compounds (B-1 – B-25) from C. sinensis were also evaluated using the SRB assay in vitro. All isolated compounds showed no cytotoxic activity against the four human cancer cell lines. (IC50 > 30 μM). This dissertation describes isolation, structural elucidation and cytotoxic activities of 55 compounds including 6 new diterpenoids, 12 new lignans, and 5 new oxylipins isolated from the trunk of A. holophylla and the twigs of C. sinensis. 11 of these compounds showed cytotoxicity against tested human cancer cell lines.