Suntornchashwej Suchada, Suwanborirux Khanit, Koga Kazushi, Isobe Minoru
Center for Bioactive Natural Products from Marine Organisms and Endophytic Fungi, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand.
Chem Asian J. 2007 Jan 8;2(1):114-22. doi: 10.1002/asia.200600219.
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.
马琳酰胺X（1）是首个与新型三肽主链相连的（7R）-灵菌酸，它是从泰国海兔伯氏鳃海蛞蝓中分离得到的。1的整体结构是根据一维和二维核磁共振以及质谱数据确定的。将核磁共振光谱实验与α-甲氧基-α-（三氟甲基）苯乙酸酯、2,2,2-三氟-1-（9-蒽基）乙醇手性溶剂化剂以及1和合成分子片段的分子力学相结合，使我们能够在不水解降解该化合物的情况下确定所有六个手性中心的绝对立体化学。化合物1表现出中等的细胞毒性、抗结核和抗疟特性。
