1. Malyngamide X: the first (7R)-lyngbic acid that connects to a new tripeptide backbone from the Thai sea hare Bursatella leachii.
- Author
-
Suntornchashwej S, Suwanborirux K, Koga K, and Isobe M
- Subjects
- Amides, Animals, Antimalarials chemistry, Antimalarials pharmacology, Antineoplastic Agents chemistry, Antineoplastic Agents pharmacology, Antitubercular Agents chemistry, Antitubercular Agents pharmacology, Carboxylic Acids chemistry, Carboxylic Acids pharmacology, Cell Line, Tumor, Cell Survival drug effects, Humans, Microbial Sensitivity Tests, Molecular Structure, Mycobacterium tuberculosis drug effects, Parasitic Sensitivity Tests, Plasmodium falciparum drug effects, Pyrrolidinones, Stereoisomerism, Thailand, Antimalarials isolation & purification, Antineoplastic Agents isolation & purification, Antitubercular Agents isolation & purification, Carboxylic Acids isolation & purification, Gastropoda chemistry, Oligopeptides chemistry
- Abstract
Malyngamide X (1), the first (7R)-lyngbic acid connected to a new tripeptide backbone, was isolated from the Thai sea hare Bursatella leachii. The gross structure of 1 was established on the basis of 1D and 2D NMR and mass spectroscopic data. Combination of the NMR spectroscopic experiments with alpha-methoxy-alpha-(trifluoromethyl)phenylacetic acid esters, 2,2,2-trifluoro-1-(9-anthryl)ethanol chiral solvating agent, and molecular mechanics of 1 and the synthetic molecular fragments allowed us to determine the absolute stereochemistry of all six stereogenic centers without hydrolytic degradation of the compound. Compound 1 displayed moderate cytotoxic, antitubercular, and antimalarial properties.
- Published
- 2007
- Full Text
- View/download PDF