{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,4]],"date-time":"2026-02-04T19:02:45Z","timestamp":1770231765783,"version":"3.49.0"},"reference-count":45,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2021,8,3]],"date-time":"2021-08-03T00:00:00Z","timestamp":1627948800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001659","name":"Deutsche Forschungsgemeinschaft","doi-asserted-by":"publisher","award":["WO 1491\/4-1 and WO 1491\/4-2"],"award-info":[{"award-number":["WO 1491\/4-1 and WO 1491\/4-2"]}],"id":[{"id":"10.13039\/501100001659","id-type":"DOI","asserted-by":"publisher"}]},{"name":"Deutsche Forschungsgemeinschaft-CAPES Collaborative Research Initiative","award":["project 418729698"],"award-info":[{"award-number":["project 418729698"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Marine Drugs"],"abstract":"<jats:p>Two new water-soluble phenanthroperylene quinones, gymnochrome H (2) and monosulfated gymnochrome A (3), as well as the known compounds gymnochrome A (4) and monosulfated gymnochrome D (5) were isolated from the deep-sea crinoid Hypalocrinus naresianus, which had been collected in the deep sea of Japan. The structures of the compounds were elucidated by spectroscopic analysis including HRMS, 1D 1H and 13C NMR, and 2D NMR. The absolute configuration was determined by ECD spectroscopy, analysis of J-couplings and ROE contacts, and DFT calculations. The configuration of the axial chirality of all isolated phenanthroperylene quinones (2\u20135) was determined to be (P). For gymnochrome H (2) and monosulfated gymnochrome A (3), a (2\u2032S,2\u2033R) configuration was determined, whereas for monosulfated gymnochrome D (5) a (2\u2032R,2\u2033R), configuration was determined. Acetylated quinones are unusual among natural products from an echinoderm and gymnochrome H (2) together with the recently reported gymnochrome G (1) represent the first isolated acetylated phenanthroperylene quinones.<\/jats:p>","DOI":"10.3390\/md19080445","type":"journal-article","created":{"date-parts":[[2021,8,4]],"date-time":"2021-08-04T02:16:07Z","timestamp":1628043367000},"page":"445","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["Structure and Absolute Configuration of Phenanthro-perylene Quinone Pigments from the Deep-Sea Crinoid Hypalocrinus naresianus"],"prefix":"10.3390","volume":"19","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7773-7527","authenticated-orcid":false,"given":"Sahithya Phani Babu","family":"Vemulapalli","sequence":"first","affiliation":[{"name":"Department of NMR-Based Structural Biology, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 G\u00f6ttingen, Germany"},{"name":"Institute for Chemistry and Biology of the Marine Environment, University of Oldenburg, Carl-von-Ossietzky-Str. 9-11, 26129 Oldenburg, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3239-3868","authenticated-orcid":false,"given":"Juan Carlos","family":"Fuentes-Monteverde","sequence":"additional","affiliation":[{"name":"Department of NMR-Based Structural Biology, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 G\u00f6ttingen, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Niels","family":"Karschin","sequence":"additional","affiliation":[{"name":"Department of NMR-Based Structural Biology, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 G\u00f6ttingen, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tatsuo","family":"Oji","sequence":"additional","affiliation":[{"name":"Nagoya University Museum, Nagoya University, Nagoya 464-8601, Japan"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Christian","family":"Griesinger","sequence":"additional","affiliation":[{"name":"Department of NMR-Based Structural Biology, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 G\u00f6ttingen, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-0944-6247","authenticated-orcid":false,"given":"Klaus","family":"Wolkenstein","sequence":"additional","affiliation":[{"name":"Department of NMR-Based Structural Biology, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 G\u00f6ttingen, Germany"},{"name":"Department of Geobiology, Geoscience Centre, University of G\u00f6ttingen, Goldschmidtstra\u00dfe 3, 37077 G\u00f6ttingen, Germany"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2021,8,3]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1021\/acs.jnatprod.8b00803","article-title":"Hypalocrinins, taurine conjugated anthraquinone and biaryl pigments from the deep sea crinoid","volume":"82","author":"Wolkenstein","year":"2019","journal-title":"Hypalocrinus Naresianus J. 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