红叶野桐茎中1个新的二萜苷类化合物

A new diterpenoid glucoside from Mallotus paxii

目的研究红叶野桐Mallotus paxii茎的化学成分。方法采用硅胶、大孔树脂、Sephadex LH-20、ODS等柱色谱以及半制备液相色谱等现代分离技术进行分离纯化,并运用HR-ESI-MS、NMR、CD等谱学技术鉴定化合物结构。通过测定化合物对脂多糖(lipopolysaccharide,LPS)诱导小鼠RAW264.7巨噬细胞释放炎症介质一氧化氮(NO)的抑制能力,评价化合物的抗炎作用;MTT法测定化合物的细胞毒性。结果从红叶野桐茎的醋酸乙酯部位中分离鉴定了7个二萜类化合物,分别为17-羟基闭花木-12,15-二烯-2-酮-3-O-β-D-吡喃葡萄糖苷(1)、对映-16α,17-二羟基-贝壳衫-3-酮(2)、阿贝苦酮(3)、对映-16β,17-二羟基阿替生烷-3-酮(4)、圆叶乌桕素A(5)、野梧桐新素E(6)和2α-hydroxy-19-deoxy-jesromotetrol(7)。体外抗炎活性研究表明,化合物3和5对脂多糖诱导的RAW264.7巨噬细胞中NO生成具有显著的抑制作用,其半数抑制浓度值分别为28.21、31.73μmol/L,且无明显细胞毒性。结论化合物1为1个新的二萜苷类化合物,命名为红叶野桐苷E。化合物1~5、7为首次从野桐属植物中分离得到,化合物6为首次从该植物中分离得到。化合物3和5具有潜在的抗炎活性。

Objective To isolate and identify the chemical constituents from Mallotus paxii.Methods The compounds were isolated and purified by column chromatography of silica gel,macroporous resin,Sephadex LH-20,ODS,and semi-preparative HPLC.The structures were elucidated via HR-ESI-MS,NMR and CD spectroscopic data interpretation.The inhibitory rates of the isolated compounds against inflammatory cytokine nitric oxide(NO)production in LPS-stimulated mouse RAW264.7 macrophages were used to evaluate the anti-inflammatory activities.The cell viability was examined by the MTT assay.Results Seven diterpenoid compounds were isolated from the ethyl acetate of M.paxii,and elucidated as 17-hydroxycleistantha-12,15-dien-2-one-3-O-β-D-glucopyranoside(1),ent-16α,17-dihydroxykauran-3-one(2),abbeokutone(3),ent-16β,17-dihydroxyatisan-3-one(4),triarotundin A(5),mallonicusin E(6),and 2α-hydroxy-19-deoxy-jesromotetrol(7).The results of the anti-inflammatory activity experiments in vitroshowed that compounds3and 5have markly inhibitory effect on NO in LPS induced RAW264.7 macrophages,with IC50values of 28.21 and 31.73μmol/L,respectively,and withoutobvious cytotoxicity.Conclusion Compound 1 was a new diterpenoid glucoside,named mallotenuifo E.Compounds 1-5,7were isolated from the genus Mallotus for the first time,and compound6wasfirst discovered from this plant.Compounds 3and 5showed potential anti-inflammatory activities.