University of Illinois Urbana-Champaign

Biologically active compounds from a clam and a tunicate

Fregeau, Nancy Louise

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Description

Title
Biologically active compounds from a clam and a tunicate
Author(s)
Fregeau, Nancy Louise
Issue Date
1992
Doctoral Committee Chair(s)
Rinehart, Kenneth L., Jr.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
  • Chemistry, Organic
  • Chemistry, Pharmaceutical
Language
eng
Abstract
  • Part I. Isolation and characterization of sphingosine analogs from the clam Spisula polynyma. Extracts of the Stimpson surf clam, Spisula polynyma, were found to cause a distinct alteration of the morphology of L1210 murine leukemia cells in which the compounds develop sharp points, usually located opposite to each other. The compounds responsible for this activity, spisulamines 285, 299 and 313 were isolated and characterized along with sphingosine and several of its analogs. The spisulamines were determined to be sphingoid-type bases. Specifically, spisulamine 285 is $(2S\sp{\*},3R\sp{\*})$-2-amino-3-octadecanol, while the other spisulamines are higher homologs. These compounds were also found to be cytotoxic to L1210 cells.
  • Part II. Ecteinascidins-antitumor compounds from the tunicate Ecteinascidia turbinata. Ecteinascidins 729, 743, 745, 756, 759A, 759B, and 770 have been isolated from the colonial tunicate Ecteinascidia turbinata. All of these compounds were cytotoxic and ecteinascidin 729 showed potent in vivo antitumor activity. The structures of these compounds were determined by extensive spectroscopic studies to be tris(tetrahydroisoquinolines) which were related to the saframycin class of antitumor antibiotics. The large number of quaternary carbons and heteroatoms required the use of long range $\sp1$H-$\sp1$H and $\sp1$H-$\sp{13}$C NMR techniques, particularly heteronuclear multiple-bond correlation. Fast atom bombardment mass spectrometry (FABMS) was also very useful in determining these structures, especially moving belt liquid chromatography/FABMS, tandem FABMS/MS and high resolution negative ion FABMS.
Type of Resource
text
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http://hdl.handle.net/2142/20793
Copyright and License Information
Copyright 1992 Fregeau, Nancy Louise

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