Sinuhirtone A, An Uncommon 17,19-Dinorxeniaphyllanoid, and Nine Related New Terpenoids from the Hainan Soft Coral <i>Sinularia hirta</i>

oleh: Zi-Hui Chen, Si-Qi Lu, Guan-Ying Han, Xu-Wen Li, Yue-Wei Guo

Format: Article
Diterbitkan: MDPI AG 2022-04-01

Deskripsi

Chemical investigation of the Hainan soft coral <i>Sinularia hirta</i> resulted in the isolation and identification of a library of sixteen structurally diverse terpenoids, including a dinorditerpenoid with an uncommon 17,19-dinorxeniaphyllane skeleton, namely sinuhirtone A (<b>7</b>), six new xeniaphyllane-type diterpenoids (<b>1</b>–<b>6</b>), one new norxeniaphyllanoid (<b>8</b>), two new norcaryophyllene-type sesquiterpenoids (<b>9</b> and <b>10</b>), together with six known related compounds (<b>11</b>–<b>16</b>). Compounds <b>1</b>–<b>3</b> are three new furanone-containing xeniaphyllane-type diterpenoids. The structures of the new compounds, including their absolute configurations, were determined by extensive spectroscopic analysis and a series of quantum chemical calculations, including quantum mechanical-nuclear magnetic resonance (QM–NMR), time-dependent density functional theory–electronic circular dichroism (TDDFT–ECD), and optical rotatory dispersion (ORD) methods. A plausible biosynthetic connection between new compounds <b>1</b>–<b>9</b> was also proposed. New compounds <b>2</b>–<b>4</b>, <b>7</b>, and <b>8</b> were evaluated for in vitro cytotoxicity against four cancer cell lines.