Detailed NMR, Including 1,1-ADEQUATE, and Anticancer Studies of Compounds from the Echinoderm Colobometra perspinosa
| Autor: | Anthony D. Wright, Dianne M. Tapiolas, Simon P. B. Ovenden, Cherie A. Motti, Jonathan L. Nielson, Catherine H. Liptrot, Philip S Kearns |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2009 |
| Předmět: |
Magnetic Resonance Spectroscopy
Stereochemistry Pharmaceutical Science Anthraquinones anticancer Article Structure-Activity Relationship chemistry.chemical_compound Cell Line Tumor Drug Discovery Animals Humans Pharmacology Toxicology and Pharmaceutics (miscellaneous) lcsh:QH301-705.5 Dichloromethane biology Australia marine natural products Gamma hydroxybutyrate 1 1-ADEQUATE biology.organism_classification Great barrier reef NMR echinoderm chemistry Echinoderm lcsh:Biology (General) Ethanesulfonic acid Methanol Drug Screening Assays Antitumor Colobometra perspinosa Heteronuclear single quantum coherence spectroscopy Echinodermata |
| Zdroj: | Marine Drugs, Vol 7, Iss 4, Pp 565-575 (2009) Marine Drugs Volume 7 Issue 4 Pages: 565-575 |
| ISSN: | 1660-3397 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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