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Superstolide A: a potent cytotoxic macrolide of a new type from the New Caledonian deep water marine sponge Neosiphonia superstes
- Source :
- Journal of the American Chemical Society. 116:6658-6663
- Publication Year :
- 1994
- Publisher :
- American Chemical Society (ACS), 1994.
-
Abstract
- A highly cytotoxic macrolide, superstolide A (1), has been isolated from the deep water marine sponge Neosiphonia superstes, collected off New Caledonia. The gross structure was determined by extensive 2D NMR experiments on the lactone 1 and on its opened-ring-derived methyl esters 2 and 3. The relative stereochemistries of the decaline moiety and of the C22-C26 fragment were determined by a combination of NMR data and acetonide analysis on 2. Absolute stereostructure of the decaline portion of 1 has been determined on the basis of GLC-modified Horeau's methodology applied to 4, whereas the results of the application of the modified Mosher's method to 1 and 3 allowed us to propose for the C22-C26 fragment the 22R, 23R, 24R, 25S, 26R configuration. We also propose the solution conformations of superstolide A (1) based on molecular dynamics and mechanics calculations using NMR-derived constraints.
- Subjects :
- chemistry.chemical_classification
ACTIVITE BIOLOGIQUE
biology
CYTOTOXIQUE
Chemistry
Stereochemistry
INVERTEBRE AQUATIQUE
General Chemistry
biology.organism_classification
Biochemistry
Nmr data
Catalysis
STRUCTURE CHIMIQUE
Deep water
Sponge
Colloid and Surface Chemistry
EPONGE
SUBSTANCE NATURELLE
Moiety
Two-dimensional nuclear magnetic resonance spectroscopy
SPONGIAIRE
Lactone
Neosiphonia
Subjects
Details
- ISSN :
- 15205126 and 00027863
- Volume :
- 116
- Database :
- OpenAIRE
- Journal :
- Journal of the American Chemical Society
- Accession number :
- edsair.doi.dedup.....c274fcd8baec2d97f5ab4ac049298a1b