UMR 5557 CNRS-UCBL - Ecologie Microbienne, Equipes 6/1/5, CESN, ISPB, 8 Avenue Rockefeller, F69373 Lyon cedex, France.
Food Chem Toxicol. 2011 Dec;49(12):3328-35. doi: 10.1016/j.fct.2011.08.026. Epub 2011 Sep 6.
In our continual course toward the valorization of traditionally used endemic flora through the analysis of its chemobiodiversity, the phytochemical analysis of aerial parts of Marrubium deserti de Noé was undertaken. Dichloromethane and methanol extracts led to the isolation of terpenoid derivatives among which two were new labdane diterpenes named marrulibacetal A and desertine, respectively. Six of them were known compounds (a mixture of the isomers cyllenin A and 15-epi-cyllenin A, marrubiin, marrulactone, marrulibacetal and β-stigmasterol) and seven known phenolic compounds were also isolated: apigenin and several 7-O-substituted derivatives (apigenin-7-O-β-neohesperidoside, apigenin-7-O-glucoside, terniflorin and apigenin-7-O-glucuronide) together with two phenylethanoid glucosides (acteoside and forsythoside B). The structures and relative configurations of the new compounds were elucidated by MS and a series of 1D and 2D NMR analyses. Some pure compounds have been evaluated for their antioxidant activities through different methods: DPPH and ABTS assays as well as CUPRAC assay. Genotoxic and antigenotoxic activities of extracts and pure compounds were also evaluated in vitro on Escherichia coli PQ37 cells by the SOS Chromotest. Some of the isolated compounds like phenylethanoid derivatives showed stronger antioxidant capacity than trolox and were also able to significantly inhibit β-galactosidase induction caused by the mutagen agent nitrofurantoin.
在我们通过分析其化学生物多样性来不断提高传统药用植物价值的过程中,我们对 Marrubium deserti de Noé 的地上部分进行了植物化学成分分析。二氯甲烷和甲醇提取物导致了萜类衍生物的分离,其中两种是新的拉伯烷二萜,分别命名为 marrulibacetal A 和 desertine。其中六种为已知化合物(异构体 cyllenin A 和 15-epi-cyllenin A 的混合物、marrubin、marrulactone、marrulibacetal 和 β-豆甾醇),还分离出了七种已知的酚类化合物:芹菜素和几种 7-O-取代衍生物(芹糖基 neohesperidoside、芹糖苷、terniflorin 和芹糖苷-7-O-葡萄糖醛酸苷)以及两种苯乙醇苷(acteoside 和forsythoside B)。新化合物的结构和相对构型通过 MS 和一系列 1D 和 2D NMR 分析阐明。通过不同方法评估了一些纯化合物的抗氧化活性:DPPH 和 ABTS 测定以及 CUPRAC 测定。还通过 SOS 显色试验在大肠杆菌 PQ37 细胞中体外评估了提取物和纯化合物的遗传毒性和抗原毒性。一些分离出的化合物,如苯乙醇苷衍生物,具有比 trolox 更强的抗氧化能力,并且能够显著抑制诱变剂硝基呋喃妥因引起的β-半乳糖苷酶诱导。