Antineoplastic Agents. 510. Isolation and structure of dolastatin 19 from the Gulf of California sea hare Dolabella auricularia.
The Gulf of California shell-less mollusc Dolabella auricularia has been found to contain a new 14-membered macrocyclic lactone linked to a 2,4-di-O-methyl-l-alpha-rhamnopyranoside, designated dolastatin 19 (1). The new cancer cell growth inhibitor (1, 8.33 x 10(-8)% yield) was obtained by bioassay (P388 lymphocytic leukemia and human cancer cell lines) directed isolation, accompanied by debromoaplysiatoxin (9.17 x 10(-7)% yield) and anhydrodebromoaplysiatoxin (2.0 x 10(-7)% yield). The structures were determined on the basis of analyses of high-resolution mass spectra and high-field NMR data. All the relative stereochemistry for the chiral centers was designated by utilizing NMR techniques.
Pettit
George R
GR
Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, Tempe, Arizona 85287-2404, USA. bpettit@asu.edu
Xu
Jun-Ping
JP
Doubek
Dennis L
DL
Chapuis
Jean-Charles
JC
Schmidt
Jean M
JM
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001048:Aplysia / Q000737:chemistry*; D002140:California; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007941:Leukemia P388; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D012210:Rhamnose / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; C492301:dolastatin 19; D012210:Rhamnose