Tong Lin, Zhang Yi, Liu Ai-Hong, Yao Li-Gong, Guo Yue-Wei, Mao Shui-Chun, Wang Bin
a School of Pharmacy , Nanchang University , Nanchang 330006 , China.
b Center of Analysis and Testing , Nanchang University , Nanchang 330047 , China.
J Asian Nat Prod Res. 2017 Jun;19(6):572-580. doi: 10.1080/10286020.2017.1317753. Epub 2017 Apr 27.
Two pairs of rare naturally occurring racemic lipids, (±)-4,7-dihydroxy-4-methyl-2,5-heptanedione (1), and (±)-7-butoxy-4-hydroxy-4-methyl-2,5-heptanedione (2) were isolated from the red alga Chondria crassicaulis Harv. The structures of the racemic mixtures of 1 and 2 were elucidated by detailed spectroscopic techniques, including 1D and 2D NMR (H and C NMR, H-H COSY, HSQC, and HMBC) as well as mass spectrometry and optical rotation experiments, and by comparison with data for related known analogs. This is the first report of naturally occurring 4-hydroxy-4-methyl-2,5-heptanedione derivatives. Antifungal, PTP1B inhibitory, and receptor tyrosine kinase inhibitory activities of these two compounds were investigated. The results showed that compounds 1 and 2 exhibited good selective inhibition against RET tyrosine kinase activity with IC values of 9.56 and 8.93 μM, respectively. Compound 1 also displayed moderate antifungal activity against Cryptococcus neoformans (32609), showing a MIC value of 32 μg/ml.
从红藻粗枝软骨藻（Chondria crassicaulis Harv.）中分离出两对罕见的天然外消旋脂质，即（±）-4,7-二羟基-4-甲基-2,5-庚二酮（1）和（±）-7-丁氧基-4-羟基-4-甲基-2,5-庚二酮（2）。通过详细的光谱技术，包括一维和二维核磁共振（氢谱和碳谱、氢-氢化学位移相关谱、异核单量子相干谱和异核多键相关谱）以及质谱和旋光实验，并与相关已知类似物的数据进行比较，阐明了1和2的外消旋混合物的结构。这是关于天然存在的4-羟基-4-甲基-2,5-庚二酮衍生物的首次报道。研究了这两种化合物的抗真菌、蛋白酪氨酸磷酸酶1B（PTP1B）抑制和受体酪氨酸激酶抑制活性。结果表明，化合物1和2对RET酪氨酸激酶活性表现出良好的选择性抑制，IC值分别为9.56和8.93 μM。化合物1对新型隐球菌（32609）也表现出中等程度的抗真菌活性，最低抑菌浓度（MIC）值为32 μg/ml。
