Ito Takuya, Nguyen Hien Minh, Win Nwet Nwet, Vo Hung Quoc, Nguyen Hoai Thi, Morita Hiroyuki
Institute of Natural Medicine, University of Toyama, 2630 Sugitani, Toyama, 930-0194, Japan.
Department of Chemistry, University of Yangon, Yangon, 11041, Myanmar.
J Nat Med. 2018 Jan;72(1):298-303. doi: 10.1007/s11418-017-1130-5. Epub 2017 Sep 22.
Sesquiterpenoid quinones with remarkable properties, such as anti-inflammatory, antibacterial, antiviral, antitumor, antiangiogenic, and differentiation-inducing activities, have reportedly been isolated from the marine sponge genera Dysidea, Spongia, and Dactylospongia. In our continuing search for bioactive compounds from marine sponges, three new sesquiterpenoid quinones, langcoquinones D-F (1-3), were isolated from the ethyl acetate extract of Spongia sp. collected from Vietnam. Their chemical structures were elucidated on the basis of extensive spectroscopic analyses. The newly isolated compounds 1-3 were assessed for their antibacterial activities against Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus, and Gram-negative bacteria, Klebsiella pneumoniae and Escherichia coli, as well as their cytotoxic activities against three human cancer cell lines (A549, lung cancer; MCF7, breast cancer; HeLa, cervical cancer) and a human normal cell line (WI-38 fibroblast). All compounds were inactive against the Gram-negative bacteria. Furthermore, langcoquinones E (2) and F (3) lacked antibacterial activities against the Gram-positive bacteria and cytotoxic activities against the tested cell lines. However, langcoquinone D (1) exhibited good antibacterial activities against Bacillus subtilis and Staphylococcus aureus, with MIC values of 12.5 and 25.0 µM, respectively. Furthermore, 1 exhibited significant cytotoxic activities against three human cancer cell lines (A549, lung cancer; MCF7, breast cancer; HeLa, cervical cancer) and a human normal cell line (WI-38 fibroblast).
据报道，已从海绵属、笛海绵属和指海绵属的海洋海绵中分离出具有显著特性的倍半萜醌，如抗炎、抗菌、抗病毒、抗肿瘤、抗血管生成和诱导分化活性。在我们持续从海洋海绵中寻找生物活性化合物的过程中，从越南采集的海绵属物种的乙酸乙酯提取物中分离出了三种新的倍半萜醌，即朗科醌D - F（1 - 3）。基于广泛的光谱分析阐明了它们的化学结构。对新分离出的化合物1 - 3进行了针对革兰氏阳性菌枯草芽孢杆菌和金黄色葡萄球菌以及革兰氏阴性菌肺炎克雷伯菌和大肠杆菌的抗菌活性评估，以及针对三种人类癌细胞系（A549，肺癌；MCF7，乳腺癌；HeLa，宫颈癌）和一种人类正常细胞系（WI - 38成纤维细胞）的细胞毒性活性评估。所有化合物对革兰氏阴性菌均无活性。此外，朗科醌E（2）和F（3）对革兰氏阳性菌缺乏抗菌活性，对测试的细胞系也缺乏细胞毒性活性。然而，朗科醌D（1）对枯草芽孢杆菌和金黄色葡萄球菌表现出良好的抗菌活性，MIC值分别为12.5和25.0 μM。此外，1对三种人类癌细胞系（A549，肺癌；MCF7，乳腺癌；HeLa，宫颈癌）和一种人类正常细胞系（WI - 38成纤维细胞）表现出显著的细胞毒性活性。
