Malyngamide X: the first (7R)-lyngbic acid that connects to a new tripeptide backbone from the Thai sea hare Bursatella leachii.
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.
Suntornchashwej
Suchada
S
Center for Bioactive Natural Products from Marine Organisms and Endophytic Fungi, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand.
Suwanborirux
Khanit
K
Koga
Kazushi
K
Isobe
Minoru
M
D000577:Amides; D000818:Animals; D000962:Antimalarials / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D000995:Antitubercular Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002264:Carboxylic Acids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D049851:Gastropoda / Q000737:chemistry*; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects; D009842:Oligopeptides / Q000737:chemistry*; D021261:Parasitic Sensitivity Tests; D010963:Plasmodium falciparum / Q000187:drug effects; D011760:Pyrrolidinones; D013237:Stereoisomerism; D013785:Thailand
D000577:Amides; D000962:Antimalarials; D000970:Antineoplastic Agents; D000995:Antitubercular Agents; D002264:Carboxylic Acids; D009842:Oligopeptides; D011760:Pyrrolidinones; C519814:malyngamide X