State Key Laboratory for Conservation and Utilization of Subtropical Agro-bioresources/Guangdong Key Laboratory for Innovative Development and Utilization of Forest Plant Germplasm, College of Forestry and Landscape Architecture, South China Agricultural University, Guangzhou 510642, China.
Guangdong Eco-Engineering Polytechnic, Guangzhou 510520, China.
Molecules. 2023 Feb 24;28(5):2119. doi: 10.3390/molecules28052119.
Four new germacrane sesquiterpene dilactones, 2-hydroxyl-11,13-dihydrodeoxymikanolide (), 3-hydroxyl-11,13-dihydrodeoxymikanolide (), 1,3-dihydroxy-4,9-germacradiene-12,8:15,6-diolide (), and (11,13-dihydrodeoxymikanolide-13-yl)-adenine (), together with five known ones (-) were isolated from the aerial parts of . Their structures were elucidated on the basis of extensive spectroscopic analysis. Compound is featured with an adenine moiety in the molecule, which is the first nitrogen-containing sesquiterpenoid so far isolated from this plant species. These compounds were evaluated for their in vitro antibacterial activity against four Gram-(+) bacteria of (), methicillin-resistant (), () and (), and three Gram-(-) bacteria of (), (), and (). Compounds and - were found to show strong in vitro antibacterial activity toward all the tested bacteria with the MIC values ranging from 1.56 to 12.5 µg/mL. Notably, compounds and showed significant antibacterial activity against the drug-resistant bacterium of with MIC value 6.25 µg/mL, which was close to reference compound vancomycin (MIC 3.125 µg/mL). Compounds and - were further revealed to show in vitro cytotoxic activity toward human tumor A549, HepG2, MCF-7, and HeLa cell lines, with IC values ranging from 8.97 to 27.39 μM. No antibacterial and cytotoxic activity were displayed for the other compounds. The present research provided new data to support that is rich in structurally diverse bioactive compounds worthy of further development for pharmaceutical applications and for crop protection in agricultural fields.
从 的地上部分分离得到了四个新的倍半萜二内酯,分别为 2-羟基-11,13-去氧去甲米坎醇内酯 ()、3-羟基-11,13-去氧去甲米坎醇内酯 ()、1,3-二羟基-4,9-吉马烷-12,8:15,6-二醇内酯 () 和 (-11,13-去氧去甲米坎醇内酯-13-基)-腺嘌呤 (),此外还有五个已知的化合物 (-)。根据广泛的光谱分析,确定了它们的结构。化合物 具有分子中的腺嘌呤部分,这是迄今为止从该植物种中分离得到的第一个含氮倍半萜。评估了这些化合物对四种革兰氏阳性菌()、耐甲氧西林的 ()、 ()和 (),以及三种革兰氏阴性菌()、 ()和 ()的体外抗菌活性。化合物 和 - 对所有测试的细菌均显示出较强的体外抗菌活性,MIC 值范围为 1.56-12.5 µg/mL。值得注意的是,化合物 和 对耐药菌 的抗菌活性显著,MIC 值为 6.25 µg/mL,接近参考化合物万古霉素(MIC 3.125 µg/mL)。进一步发现化合物 和 - 对人肿瘤 A549、HepG2、MCF-7 和 HeLa 细胞系具有体外细胞毒性活性,IC 值范围为 8.97-27.39 μM。其他化合物则没有显示出抗菌和细胞毒性活性。本研究提供了新的数据支持,表明 富含结构多样的生物活性化合物,值得进一步开发用于药物应用和农业领域的作物保护。