Detailed NMR, including 1,1-ADEQUATE, and anticancer studies of compounds from the echinoderm Colobometra perspinosa.

Marine Drugs
Anthony D WrightCatherine H Liptrot

Abstract

From the dichloromethane/methanol extract of the crinoid Colobometra perspinosa, collected south east of Richards Island (Bedara), Family Islands, Central Great Barrier Reef, Australia, 3-(1'-hydroxypropyl)-1,6,8-trihydroxy-9,10-anthraquinone [one of the two stereoisomers of rhodoptilometrin, (1)], 3-propyl-1,6,8-trihydroxy-9,10-anthraquinone (3), 2-[(phenylacetyl)amino]ethanesulfonic acid (4), and 4-hydroxybutanoic acid (5) were isolated. Comparison of (1)H- and (13)C-NMR data for rhodoptilometrin (1) with those reported in the literature showed significant differences for some resonances associated with rings A and C. In an attempt to provide accurately assigned (1)H- and (13)C-NMR data, as well as to confirm the structure of 1, a thorough NMR investigation of this compound was undertaken. Measurements included: concentration dependent (13)C, 1D selective NOE, HSQC, HMBC and 1,1-ADEQUATE. The NMR data for 4 and 5 are reported here for the first time, as is their occurrence from the marine environment. The in vitro anticancer activity of the original extract was found to be associated with 1, 3 and 5.

References

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Sep 1, 1987·Xenobiotica; the Fate of Foreign Compounds in Biological Systems·J P Cravedi, J Tulliez
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Jun 10, 2009·Journal of Natural Products·Dianne M TapiolasCherie A Motti

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Citations

Jan 7, 2014·Chemical & Pharmaceutical Bulletin·Zhao-Yuan WuKai-Mei Wang
Aug 18, 2010·Marine Drugs·Hedi Indra JanuarAnthony D Wright
Feb 26, 2011·Journal of Natural Products·Simon P B OvendenDianne M Tapiolas
Apr 26, 2011·Journal of Natural Products·Simon P B OvendenCherie A Motti
Mar 31, 2017·Natural Product Reports·Yunjiang FengRohan A Davis
Aug 24, 2018·Chemical & Pharmaceutical Bulletin·Le Thi VienChau Van Minh
Jan 3, 2019·Journal of Separation Science·Statis PataridisIvan Mikšík
Jan 22, 2011·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·D-P HäderR C Worrest
Dec 15, 2010·Natural Product Reports·John W BluntMichèle R Prinsep
Jan 4, 2021·Journal of Cancer Research and Clinical Oncology·Jiaen WeiZunnan Huang
Jun 3, 2021·Marine Drugs·Giulia GrecoCarmela Fimognari
Jan 1, 2019·Journal of Natural Products·Klaus WolkensteinChristian Griesinger
Dec 16, 2010·Journal of Natural Products·Simon P B OvendenCherie A Motti
Aug 28, 2021·Biomedicines·Rodion KhotimchenkoYuri Khotimchenko

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Datasets Mentioned

BETA
G212468

Methods Mentioned

BETA
NMR

Software Mentioned

Windows 2000

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