Bioactive constituents from the green alga Caulerpa racemosa.
Bioactive constituents from the green alga Caulerpa racemosa.
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DOI：
10.1016/j.bmc.2014.11.031
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发表时间：
2015
影响因子：
3.5
通讯作者：
Peng-fei Yang;Ding-Quan Liu;Tongjun Liang;Jia Li;Hai-Yan Zhang;Ai-hong Liu;Yue‐Wei Guo;Shui-Chun Mao-S
中科院分区：
文献类型：
--
作者：
Peng-fei Yang;Ding-Quan Liu;Tongjun Liang;Jia Li;Hai-Yan Zhang;Ai-hong Liu;Yue‐Wei Guo;Shui-Chun Mao-S
从绿色拟蕨藻（Caulerparacemosa）中分离得到3个二萜类化合物，包括一对差向异构体外消旋丁烯酸内酯A和B（1和2），4′，5 ′-脱氢二网丝藻A（3），α-生育酚烷氧基（8），（23 E）-3β-羟基-豆甾-5，23-二烯-28-酮（11），以及12个已知化合物。通过对光谱数据的详细分析，并与相关已知化合物的数据进行比较，阐明了新化合物的结构。差向异构体（1和2）是两种不常见的带有β-甲基-γ-取代丁烯基的二萜类内酯，3和8分别代表了第一个天然存在的带有补血酸酯基和3，5-二甲基苯氧基官能团的天然产物。在体外评价分离的化合物对PTP 1B和相关PTPs（TCPTP、CDC 25 B、LAR、SHP-1和SHP-2）的酶抑制活性。化合物3、5、6和9 - 14具有不同程度的PTP 1B抑制活性，IC 50值在2.30 ~ 50.02 μM之间。其中化合物3、9和11对PTP 1B的抑制活性最强，IC 50值分别为2.30、3.85和3.80 μM。更重要的是，有效的PTP 1B同源物3，9和11也显示出对高度同源的TCPTP和其他PTP的高选择性。此外，研究了分离物对Aβ25-35诱导的SH-SY 5 Y细胞损伤的神经保护作用。化合物10、11和14对Aβ25-35诱导的SH-SY 5 Y细胞损伤表现出显著的神经保护作用，在10 μM时细胞活力增加11.31-15.98%。此外，测试了分离的化合物对人癌细胞系A-549和HL-60的细胞毒活性。
Three diterpenoids, including a pair of epimers, racemobutenolids A and B (1and2), and 4′,5′-dehydrodiodictyonema A (3), an α-tocopheroid, α-tocoxylenoxy (8), and an 28-oxostigmastane steroid, (23E)-3β-hydroxy-stigmasta-5,23-dien-28-one (11), together with 12 known compounds, were isolated from the green alga Caulerparacemosa. The structures of the new compounds were elucidated by detailed analysis of spectroscopic data, and by comparison with data for related known compounds. The epimers (1and2) are two unusual diterpenoid lactones bearing a β-methyl-γ-substituted butenolide moiety, and3and8represent the first naturally occurring natural products with a hematinic acid ester group and 3,5-dimethylphenoxy functionality, respectively. The enzyme inhibitory activities of the isolated compounds were evaluated in vitro against PTP1B and related PTPs (TCPTP, CDC25B, LAR, SHP-1, and SHP-2). Compounds3,5,6, and9–14exhibited different levels of PTP1B inhibitory activities with IC50values ranging from 2.30 to 50.02 μM. Of these compounds,3,9, and11showed the most potent inhibitory activities towards PTP1B with IC50values of 2.30, 3.85, and 3.80 μM, respectively. More importantly, the potent PTP1B inhibitors3,9, and11also displayed high selectivity over the highly homologous TCPTP and other PTPs. Also, the neuroprotective effects of the isolates against Aβ25-35-induced cell damage in SH-SY5Y cells were investigated. Compounds10,11, and14exhibited significant neuroprotective effects against Aβ25-35-induced SH-SY5Y cell damage with 11.31–15.98% increases in cell viability at 10 μM. In addition, the cytotoxic activities of the isolated compounds were tested against the human cancer cell lines A-549 and HL-60.