Malyngamide X: The First (7R)‐Lyngbic Acid that Connects to a New Tripeptide Backbone from the Thai Sea Hare Bursatella leachii |
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| Authors: | Suchada Suntornchashwej Dr Khanit Suwanborirux Dr Kazushi Koga Minoru Isobe Prof?Dr |
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| Institution: | 1. Center for Bioactive Natural Products from Marine Organisms and Endophytic Fungi (BNPME), Faculty of Pharmaceutical Sciences, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand, Fax: (+66)?02‐254‐5195;2. Laboratory of Organic Chemistry, Bioagricultural Sciences, Nagoya University, Furocho, Chikusa, Nagoya 464‐8601, Japan, Fax: (+81)?52‐789‐4111;3. Institute of Advanced Research, Nagoya University, Furocho, Chikusa, Nagoya 464‐8601, Japan |
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| 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 α‐methoxy‐α‐(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. |
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| Keywords: | chiral resolution chiral solvating agent malyngamide X natural products sea hare |
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