Hawaiienols A–D, Highly Oxygenated <i>p</i>‑Terphenyls
from an Insect-Associated Fungus, <i>Paraconiothyrium hawaiiense</i>
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Abstract
Four new highly oxygenated <i>p</i>-terphenyls, hawaiienols
A–D (<b>1</b>–<b>4</b>), have been isolated
from cultures of <i>Paraconiothyrium hawaiiense</i>, a fungus
associated with the <i>Septobasidium</i>-infected insect <i>Diaspidiotus</i> sp.; their structures were elucidated primarily
by NMR experiments. The absolute configurations of <b>1</b> and <b>2</b>–<b>4</b> were assigned by single-crystal X-ray
diffraction analysis using Cu Kα radiation and via electronic
circular dichroism calculations, respectively. Compound <b>1</b> incorporated the first naturally occurring 4,7-dioxatricyclo[3.2.1.0<sup>3,6</sup>]octane unit in its <i>p</i>-terphenyl skeleton
and showed cytotoxicity toward six human tumor cell lines