两种红树林植物海漆和海桑化学成分研究
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摘要
本论文对两种红树林植物海漆(Excoecaria agallocha L.)和海桑(Sonneratia caseolaris L.)的化学成分进行了系统研究。
采用常规的硅胶柱层析、制备薄层层析、凝胶Sephadex LH-20柱层析、MCI柱层析、反相硅胶柱层析、半制备型HPLC以及重结晶等手段,从海漆(Excoecaria agalloch L. )中分离得到40个化合物,从海桑(Sonneratia caseolaris L.)中分离得到30个化合物。利用各种现代波谱技术(IR、UV、ESI-MS、EI-MS、1D-NMR、2D-NMR等)及其化学物理性质,确定了海漆中32个化合物的结构,其中包括1个新的三萜天然产物以及15个首次从海漆中报道的化合物;确定了海桑中27个化合物的结构,其中包括1个新化合物和一个首次报道其碳谱数据的化合物。本文为首次报道海桑的化学成分研究。
对海漆和海桑粗提物及分离得到的部分化合物进行了抗肝癌细胞毒活性筛选,化合物S22表现出较强活性,其IC50为2.8μg/mL;海漆和海桑粗提物及其它部分单体化合物只表现出微弱活性;阳性对照丝裂霉素C的IC50为1.1μg/mL。
对分离得到的部分样品还进行了抗菌活性测试,各样品在测试浓度下对测试菌均未表现出明显的抗菌活性。
首次研究了海漆挥发性成分及其季节性变化。利用水蒸汽法提取了不同季节海漆的挥发性成分,通过GC-MS鉴定其化学组成,发现脂肪酸、二萜和倍半萜是海漆挥发性成分的主要组成,不同季节的挥发性成分差异较大。
This dissertation describes the isolation, structure elucidation, and bioactivity evaluation of chemical constituents isolated from the mangrove plants Excoecaria agallocha L. and Sonneratia caseolaris L.
Chemical investigation of Excoecaria agallocha L. afford 40 compounds by combination of column chromatography on silica gel, RP-18, and Sephadex LH-20, as well as preparative thin layer chromatography (PTLC), recrystallization, and semi-preparative HPLC. The structures of these compounds were elucidated by means of spectroscopic methods including IR, UV, ESI-MS, EI-MS, 1D-NMR and 2D-NMR. Thirty-two compounds were identified from Excoecaria agallocha L. that included one triterpenoid reported in nature for the first time and 15 compounds isolated from Excoecaria agallocha L. for the first time.
Chemical investigation of Sonneratia caseolaris L. obtained 30 compounds. Twenty-seven constituents including one new steroid were elucidated. Besides we reported the 13C-NMR data of one triterpenoid firstly. It was also the first report about the chemical constituents of Sonneratia caseolaris L.
The crude extracts of Excoecaria agallocha L. and Sonneratia caseolaris L. along with parts of isolated pure compounds were screened for anti-hepatoma cell cytotoxic activity. And compound S22 showed significant activity in vitro against SMMC-7721 human hepatoma cell whose IC50 was 2.8μg/mL. However the crude extracts of Excoecaria agallocha L. and Sonneratia caseolaris L., and part of other compounds only showed weak activity. The IC50 of positive controlled sample (mitomycin C) was 1.1μg/mL.
The antibacterial activities of some isolated compounds were studied. However the screened compounds showed little antibacterial activities against the tested bacterial strains.
Composition and seasonal variation of the volatile constituents from mangrove plant Excoecaria agallocha L. were investigated firstly by extracted through hydro-distillation and identified by means of capillary gas chromatography combined gas chromatography-mass spectrometry (GC-MS). GC-MS results indicated that fatty acids, diterpenoids and sesquiterpenoids were main components in volatile constituents of Excoecaria agallocha L. of different seasons and the volatile constituents displayed significant seasonal variation.
采用常规的硅胶柱层析、制备薄层层析、凝胶Sephadex LH-20柱层析、MCI柱层析、反相硅胶柱层析、半制备型HPLC以及重结晶等手段,从海漆(Excoecaria agalloch L. )中分离得到40个化合物,从海桑(Sonneratia caseolaris L.)中分离得到30个化合物。利用各种现代波谱技术(IR、UV、ESI-MS、EI-MS、1D-NMR、2D-NMR等)及其化学物理性质,确定了海漆中32个化合物的结构,其中包括1个新的三萜天然产物以及15个首次从海漆中报道的化合物;确定了海桑中27个化合物的结构,其中包括1个新化合物和一个首次报道其碳谱数据的化合物。本文为首次报道海桑的化学成分研究。
对海漆和海桑粗提物及分离得到的部分化合物进行了抗肝癌细胞毒活性筛选,化合物S22表现出较强活性,其IC50为2.8μg/mL;海漆和海桑粗提物及其它部分单体化合物只表现出微弱活性;阳性对照丝裂霉素C的IC50为1.1μg/mL。
对分离得到的部分样品还进行了抗菌活性测试,各样品在测试浓度下对测试菌均未表现出明显的抗菌活性。
首次研究了海漆挥发性成分及其季节性变化。利用水蒸汽法提取了不同季节海漆的挥发性成分,通过GC-MS鉴定其化学组成,发现脂肪酸、二萜和倍半萜是海漆挥发性成分的主要组成,不同季节的挥发性成分差异较大。
This dissertation describes the isolation, structure elucidation, and bioactivity evaluation of chemical constituents isolated from the mangrove plants Excoecaria agallocha L. and Sonneratia caseolaris L.
Chemical investigation of Excoecaria agallocha L. afford 40 compounds by combination of column chromatography on silica gel, RP-18, and Sephadex LH-20, as well as preparative thin layer chromatography (PTLC), recrystallization, and semi-preparative HPLC. The structures of these compounds were elucidated by means of spectroscopic methods including IR, UV, ESI-MS, EI-MS, 1D-NMR and 2D-NMR. Thirty-two compounds were identified from Excoecaria agallocha L. that included one triterpenoid reported in nature for the first time and 15 compounds isolated from Excoecaria agallocha L. for the first time.
Chemical investigation of Sonneratia caseolaris L. obtained 30 compounds. Twenty-seven constituents including one new steroid were elucidated. Besides we reported the 13C-NMR data of one triterpenoid firstly. It was also the first report about the chemical constituents of Sonneratia caseolaris L.
The crude extracts of Excoecaria agallocha L. and Sonneratia caseolaris L. along with parts of isolated pure compounds were screened for anti-hepatoma cell cytotoxic activity. And compound S22 showed significant activity in vitro against SMMC-7721 human hepatoma cell whose IC50 was 2.8μg/mL. However the crude extracts of Excoecaria agallocha L. and Sonneratia caseolaris L., and part of other compounds only showed weak activity. The IC50 of positive controlled sample (mitomycin C) was 1.1μg/mL.
The antibacterial activities of some isolated compounds were studied. However the screened compounds showed little antibacterial activities against the tested bacterial strains.
Composition and seasonal variation of the volatile constituents from mangrove plant Excoecaria agallocha L. were investigated firstly by extracted through hydro-distillation and identified by means of capillary gas chromatography combined gas chromatography-mass spectrometry (GC-MS). GC-MS results indicated that fatty acids, diterpenoids and sesquiterpenoids were main components in volatile constituents of Excoecaria agallocha L. of different seasons and the volatile constituents displayed significant seasonal variation.
引文
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