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Article

Structure and Absolute Configuration of Phenanthro-perylene Quinone Pigments from the Deep-Sea Crinoid Hypalocrinus naresianus

1
Department of NMR-Based Structural Biology, Max Planck Institute for Biophysical Chemistry, Am Fassberg 11, 37077 Göttingen, Germany
2
Institute for Chemistry and Biology of the Marine Environment, University of Oldenburg, Carl-von-Ossietzky-Str. 9-11, 26129 Oldenburg, Germany
3
Nagoya University Museum, Nagoya University, Nagoya 464-8601, Japan
4
Department of Geobiology, Geoscience Centre, University of Göttingen, Goldschmidtstraße 3, 37077 Göttingen, Germany
*
Authors to whom correspondence should be addressed.
These authors contributed equally.
Academic Editors: Natalia P. Mishchenko and Elena A. Vasileva
Mar. Drugs 2021, 19(8), 445; https://doi.org/10.3390/md19080445
Received: 9 July 2021 / Revised: 23 July 2021 / Accepted: 28 July 2021 / Published: 3 August 2021
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 (25) was determined to be (P). For gymnochrome H (2) and monosulfated gymnochrome A (3), a (2′S,2″R) configuration was determined, whereas for monosulfated gymnochrome D (5) a (2′R,2″R), 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. View Full-Text
Keywords: crinoid; Hypalocrinus naresianus; phenanthroperylene quinones; gymnochromes; configuration determination crinoid; Hypalocrinus naresianus; phenanthroperylene quinones; gymnochromes; configuration determination
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MDPI and ACS Style

Vemulapalli, S.P.B.; Fuentes-Monteverde, J.C.; Karschin, N.; Oji, T.; Griesinger, C.; Wolkenstein, K. Structure and Absolute Configuration of Phenanthro-perylene Quinone Pigments from the Deep-Sea Crinoid Hypalocrinus naresianus. Mar. Drugs 2021, 19, 445. https://doi.org/10.3390/md19080445

AMA Style

Vemulapalli SPB, Fuentes-Monteverde JC, Karschin N, Oji T, Griesinger C, Wolkenstein K. Structure and Absolute Configuration of Phenanthro-perylene Quinone Pigments from the Deep-Sea Crinoid Hypalocrinus naresianus. Marine Drugs. 2021; 19(8):445. https://doi.org/10.3390/md19080445

Chicago/Turabian Style

Vemulapalli, Sahithya P.B., Juan C. Fuentes-Monteverde, Niels Karschin, Tatsuo Oji, Christian Griesinger, and Klaus Wolkenstein. 2021. "Structure and Absolute Configuration of Phenanthro-perylene Quinone Pigments from the Deep-Sea Crinoid Hypalocrinus naresianus" Marine Drugs 19, no. 8: 445. https://doi.org/10.3390/md19080445

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