Polyacetylene and phenolic constituents from the roots of <i>Codonopsis javanica</i>

Abstract

Chemical investigation of the roots of <i>Codonopsis javanica</i> resulted in isolation of 12 compounds, including one new polyacetylene, codojavanyol (<b>1</b>), one new phenolic glycoside, codobenzyloside (<b>7</b>), and 10 known compounds, (2<i>E</i>,8<i>E</i>)-9-(tetrahydro-2<i>H</i>-pyran-2-yl)nona-2,8-diene-4,6-diyl-1-ol (<b>2</b>), lobetyol (<b>3</b>), lobetyolin (<b>4</b>), lobetyolinin (<b>5</b>), cordifolioidyne B (<b>6</b>), benzyl-<i>α</i>-L-arabinopyranosyl (1-6)-<i>β</i>-D-glucopyranoside (<b>8</b>), (<i>Z</i>)-8-<i>β</i>-D-glucopyranosyloxycinnamic acid (<b>9</b>), syringin (<b>10</b>), syringaresinol (<b>11</b>), and tryptophan (<b>12</b>). Their structures were elucidated by 1 D and 2 D NMR and MS spectroscopic analyses in comparison with the data reported in the literature. The stereochemistry of the C-2' position of <b>1</b> was identified based on time-dependent density functional theory (TDDFT) electronic circular dichroism (ECD) calculation. Among the isolates, compounds <b>3-5</b> were shown to have weak cytotoxicity toward three human carcinoma cell lines, including lung (A549), liver (HepG2), and breast (MCF7), with the induction of 41.4 to 55.6% cell death at the concentration of 100 µM.