English
 
Help Privacy Policy Disclaimer
  Advanced SearchBrowse

Item

ITEM ACTIONSEXPORT
  Structure and absolute configuration of phenanthro-perylene quinone pigments from the deep-sea crinoid Hypalocrinus naresianus

Vemulapalli, S. P., Fuentes-Monteverde, J. C., Karschin, N., Oji, T., Griesinger, C., & Wolkenstein, K. (2021). Structure and absolute configuration of phenanthro-perylene quinone pigments from the deep-sea crinoid Hypalocrinus naresianus. Marine Drugs, 19(8): 445. doi:10.3390/md19080445.

Item is

Basic

show hide
Genre: Journal Article

Files

show Files

Locators

show

Creators

show
hide
 Creators:
Vemulapalli, S. P.1, Author              
Fuentes-Monteverde, J. C.1, Author              
Karschin, N., Author
Oji, T., Author
Griesinger, C.2, Author              
Wolkenstein, K., Author
Affiliations:
1Department of NMR Based Structural Biology, MPI for Biophysical Chemistry, Max Planck Society, ou_578567              
2Department of NMR Based Structural Biology, MPI for biophysical chemistry, Max Planck Society, ou_578567              

Content

show
hide
Free keywords: crinoid; Hypalocrinus naresianus; phenanthroperylene quinones; gymnochromes; configuration determination
 Abstract: 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 (2–5) 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.

Details

show
hide
Language(s): eng - English
 Dates: 2021-08-03
 Publication Status: Published online
 Pages: -
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.3390/md19080445
 Degree: -

Event

show

Legal Case

show

Project information

show

Source 1

show
hide
Title: Marine Drugs
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: -
Pages: - Volume / Issue: 19 (8) Sequence Number: 445 Start / End Page: - Identifier: -