Department of Medicinal Chemistry, University of Florida, Gainesville, Florida 32610, USA.
J Nat Prod. 2010 Mar 26;73(3):463-6. doi: 10.1021/np900614n.
A new stereoisomer of malyngamide C, 8-epi-malyngamide C (1), and the known compound lyngbic acid [(4E,7S)-7-methoxytetradec-4-enoic acid] were isolated from a sample of Lyngbya majuscula collected near Bush Key, Dry Tortugas, Florida. The structure of 1 was determined by NMR and MS experiments. The absolute configuration of 1 was determined by selective Mitsunobu inversion of C-8 to give malyngamide C, as determined by NMR, MS, and comparison of specific rotation. Both 1 and malyngamide C were found to be cytotoxic to HT29 colon cancer cells (IC(50) 15.4 and 5.2 microM, respectively) and to inhibit bacterial quorum sensing in a reporter gene assay.
从佛罗里达州布什礁附近采集的大螺旋藻中分离得到一种新的马良酰胺 C 立体异构体，8-表马良酰胺 C（1），以及已知化合物林格比酸[（4E，7S）-7-甲氧基十四碳-4-烯酸]。通过 NMR 和 MS 实验确定了 1 的结构。通过对 C-8 的选择性 Mitsunobu 反转，确定了 1 的绝对构型，得到马良酰胺 C，这通过 NMR、MS 和比旋光度的比较来确定。1 和马良酰胺 C 均对 HT29 结肠癌细胞具有细胞毒性（IC50 分别为 15.4 和 5.2 μM），并在报告基因测定中抑制细菌群体感应。
