| Summary: | Two new water-soluble phenanthroperylene quinones, gymnochrome H (<b>2</b>) and monosulfated gymnochrome A (<b>3</b>), as well as the known compounds gymnochrome A (<b>4</b>) and monosulfated gymnochrome D (<b>5</b>) were isolated from the deep-sea crinoid <i>Hypalocrinus naresianus</i>, which had been collected in the deep sea of Japan. The structures of the compounds were elucidated by spectroscopic analysis including HRMS, 1D <sup>1</sup>H and <sup>13</sup>C NMR, and 2D NMR. The absolute configuration was determined by ECD spectroscopy, analysis of <i>J</i>-couplings and ROE contacts, and DFT calculations. The configuration of the axial chirality of all isolated phenanthroperylene quinones (<b>2</b>–<b>5</b>) was determined to be (<i>P</i>). For gymnochrome H (<b>2</b>) and monosulfated gymnochrome A (<b>3</b>), a (2′<i>S</i>,2″<i>R</i>) configuration was determined, whereas for monosulfated gymnochrome D (<b>5</b>) a (2′<i>R</i>,2″<i>R</i>), configuration was determined. Acetylated quinones are unusual among natural products from an echinoderm and gymnochrome H (<b>2</b>) together with the recently reported gymnochrome G (<b>1</b>) represent the first isolated acetylated phenanthroperylene quinones.
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