Detailed NMR, Including 1,1-ADEQUATE, and Anticancer Studies of Compounds from the Echinoderm Colobometra perspinosa

  title={Detailed NMR, Including 1,1-ADEQUATE, and Anticancer Studies of Compounds from the Echinoderm Colobometra perspinosa},
  author={Anthony David Wright and Jonathan L. Nielson and Dianne M. Tapiolas and Cherie A. Motti and Simon P. B. Ovenden and Philip S. Kearns and Catherine H. Liptrot},
  journal={Marine Drugs},
  pages={565 - 575}
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 1H- and 13C-NMR data for rhodoptilometrin… 

Figures and Tables from this paper

Cytotoxic effects of the anthraquinone derivatives 1′-deoxyrhodoptilometrin and (S)-(−)-rhodoptilometrin isolated from the marine echinoderm Comanthus sp.
It is suggested that the anthraquinone derivative 1′-deoxyrhodoptilometrin (SE11) may be an interesting lead structure for the development of new anticancer drugs.
Cytotoxic Cembranes from Indonesian Specimens of the Soft Coral Nephthea sp
Methanol extracts of two specimens of the soft coral Nephthea sp. collected from the Seribu Islands, Indonesia, were active in an anticancer bioassay. One new (1) and four known diterpenes (2–5)
Hypalocrinins, Taurine-Conjugated Anthraquinone and Biaryl Pigments from the Deep Sea Crinoid Hypalocrinus naresianus.
Five new water-soluble amido- and aminoanthraquinone pigments, hypalocrinins A-E, are the first naturally occurring anthraquinones and anthraquone biaryls conjugated with taurine.
Four new anthraquinones from a soil actinomycete Streptomyces sp. WS-13394 and their bioactivities
Four new alkylated anthraquinone analogues were isolated from the soil actinomycete Streptomyces sp.
Antifouling phenyl ethers and other compounds from the invertebrates and their symbiotic fungi collected from the South China Sea
The study of structure–activity relationship (SAR) revealed that the introduction of acetoxy groups and bromine atoms to phenyl ether derivatives could significantly improve their antifouling activities.
Comosusols A-D and comosone A: cytotoxic compounds from the brown alga Sporochnus comosus.
Bioassay-guided fractionation of extracts of the brown alga Sporochnus comosus led to the isolation of five new compounds, comosUSols A-D (3-6) and comosone A (7), which were elucidated using standard one- and two-dimensional NMR techniques, as well as comparison with literature values.
Marine Anthraquinones: Pharmacological and Toxicological Issues
The aim of this review is to critically describe the anticancer potential of anthraquinones derived from marine sources and their genotoxic and mutagenic potential.
Anti-inflammatory Anthraquinones from the Crinoid Himerometra magnipinna
In the in vitro anti-inflammatory effects test, compound 2 was found to significantly inhibit the accumulation of the pro-inflammatory iNOS protein of the LPS-stimulated RAW264.7 macrophage cells.


Antiplasmodial and cytotoxic metabolites from the Maltese sponge Agelas oroides.
Biological activity assessment of all isolates indicate 5 to have moderate antiplasmodial activity, as well as being cytotoxic, and 2 to be moderately cytot toxic towards several cancer cell lines.
Eusynstyelamides A, B, and C, nNOS inhibitors, from the ascidian Eusynstyela latericius.
Eusynstyelamides A-C (1-3) were isolated from the Great Barrier Reef ascidian Eusyn Styela latericius, together with the known metabolites homarine and trigonelline, and the structures were elucidated by interpretation of their spectroscopic data.
Inhibition of heme detoxification processes underlies the antimalarial activity of terpene isonitrile compounds from marine sponges.
These studies suggest that the active isonitrile compounds, like the quinoline antimalarials, exert their antiplasmodial activity by preventing FP detoxification.
Pigments of marine animals. VI. Anthraquinoid pigments of the crinoids Ptilometra australis Wilton and Tropiometra afra Hartlaub
The crinoid Ptilometra australis Wilton yields to organic solvents a complex mixture of pigments from which the three principal components have been separated by chromatography on magnesium
Anthraquinone pigments from the crinoid Comanthus bennetti
Taurine conjugates as metabolites of arylacetic acids in the ferret.
The role of taurine as an alternative to glycine in the metabolic conjugation of arylacetic acids is discussed and their characterization and properties were studied.
Broad spectrum effects of secondary metabolites from the red alga delisea pulchra in antifouling assays
Activity of the D. pulchra metabolites was comparable to that of the heavy metals and biocides currently used in antifouling paints, however, no single compound was most active in all tests and some meta...
Application of the 1, n -ADEQUATE Experiment in the Assignment of Highly Substituted Aromatic Compounds
This communication describes the application of the 1, n-ADEQUATE experiment to differentiate between the two possible products ( 4 and 5) of an acylation reaction of starting material 3. The
Chemical Defense Against Different Marine Herbivores: Are Amphipods Insect Equivalents?
The ability of amphipods to circumvent the chemical defenses of Dictyota, and the fact that the two species of algae most readily consumed by amphipODs were the twospecies least readily consumedBy fish, suggest that predation and herbivory by fishes may be major factors selecting for amphipod that can live on, and eat, seaweeds that are unpalatable to fishes.
Urinary metabolites of dodecylcyclohexane in Salmo gairdneri: evidence of aromatization and taurine conjugation in trout.
  • J. Cravedi, J. Tulliez
  • Chemistry, Biology
    Xenobiotica; the fate of foreign compounds in biological systems
  • 1987
The urinary metabolites of 3H-dodecylcyclohexane were investigated in rainbow trout, Salmo gairdneri R. after a single intragastric dose and more than 30% of the urinary 3H was present as phenylacetic and cyclohexylacetics acids conjugated with taurine.